Regular readers know that this newsletter has two permanent sections:

• Writings - where I usually write and / or refer to one or more original pieces that I published in the previous months, typically about venture or the startup ecosystem.

• Readings - about what I read and learnt about. My reading diet is tilted rather heavily in favour of books and podcast transcripts, and against articles / newsletters. This will naturally reflect in the reading list.

This is a long newsletter, though this particular edition is amongst the shorter ones I have sent out. Think of it as a monthly magazine from me (only the frequency may not be monthly!). I don’t know if you can read this entire newsletter (and peruse the links) in one sitting, and even if you do a second run (which I very much doubt), you will have to pick and choose what to focus on. A good way to read this newsletter is to certainly read my original writing(s) below, and then glance through the rest and pick 1-2-3 items that pique your interest. Anything more is a bonus!

Writings

I wrote a piece distilling the key learnings from my career.

The piece came about as a result of the talk I gave at Rubaru, Amazon India’s Finance Org’s career day. I was asked to speak about my career journey and transition to the VC world, as well as what I have seen as key hallmarks of successful careers. I later got this message (see image) from Sourav Das fm Amazon who thought of me, and coordinated the talk.

Subsequently, I shared notes of my talk internally within Blume and many found it interesting as well. I decided then to convert it into an article. I hope you find it useful!

My 5 career learnings, as shared in the piece.

1/ Try to be the only, find your intersection of two or more skills and own that combination.

2/ There’s a hidden role inside your role, figure out what it actually is.

3/ Play tennis, not badminton, the space you pick matters more than how well you play it, unless your obsession says otherwise.

4/ Put unreasonable effort into something that is important to you. “Don’t save anything for the swim back.”

5/ Find your obsession, the thing that’s work for everyone else and play for you, and don’t let go of it.

Readings

Books

1/ Sakina’s Kiss (2021) - Vivek Shanbhag, translated by Srinath Perur

Fiction, after a while. My second Vivek Shanbhagh; the first was the brilliant Ghachar Ghochar, which I read in 2023. This isn’t as good as that but still a fine read. Shanbhag has a masterful ability to bring in unease and discomfort into cozy domesticity. We saw that in Ghachar Ghochar and it continues here too. Plot: A family sees visits by unsavoury characters; meanwhile and connected to this is that their daughter goes AWOL. She returns eventually, but her absence provides the setting for exploring an uncomfortable backstory of the protagonist’s relative; and you know that the fissures her disappearance and return opens up will never ever be succesfully closed.

2/ How to Rule the World (2026) - Theo Baker

Two broad strands to this candid, vulnerable memoir of Theo Baker’s first two years as a Stanford undergrad. First is the story of his investigation as a student reporter into the Stanford President’s past research work which eventually led to the President retracting several papers, and stepping down. The second, and which runs parallel to the investigation is the detailing of how venture capitalists and talent scouts have captured Stanford, and the second order effects of this; there is of course genuine startup activity, but a lot of it is also startup / founder LARPing. Valuable sociological / anthropological guide to early ‘20s Stanford. The title comes from the name of a secret and select course that is offered on campus (v ‘Secret History’ types!) that Theo fails to get into.

3/ How to Take Smart Notes (2017) - Sonke Ahrens

This is a popular book in PKM circles. It looks at the note-taking practices of a German sociologist Niklas Luhmann (1927-98), who had a note-taking system called the slip-box or zettelkasten. In this system, he would read a paper / book and write out two types of notes, one a ‘literature or bibliographic note’ on details about the book / paper including a short gist, and the second, a brief ‘permanent note’ explaining his view of the paper or book in his own words, on an index card or two. Writing out the notes in his own words was important as writing it out drove better understanding of the topic, given he had to locate the topic in his context and frame of learning.

The bibliographic notes go into a separate bibliographic reference system or file, and the permanent notes to his ‘slip-box’ (of already existing index cards). These permanent notes (on index cards) would ideally link to what already exists (unless it is an entirely new topic) and would be placed beside that in the slip-box and / or cross-referenced to the existing notes. When adding notes on an existing topic, he would add further notes on why they are connected or contradict each other. Over time he would build clusters of notes on topics and at some point he would look at a cluster and decide it was sizable enough for him to publish something on it. Through this method of continuously adding and immediately cross-referencing notes he was able to be highly productive, and become a well-regarded sociologist.

A point to note, of course, is that Niklas Luhmann is not terribly well known, at least outside of Germany - now there’s no major theory that I know Niklas Luhmann is associated with despite prolific writing and publishing. So I do wonder sometimes about whether elaborate note-taking systems help in creating something truly impactful? On a related note, why aren’t these note-taking experts or productivity buffs, billionaires or multi-millionaires? Why are they still shilling for $ on youtube?! Anyway, rant over!

Irrespective of the above criticism, we can distil the key principles of his note-taking system / slip-box into the following generalisable rule set:

1/ When you find something interesting or useful, write this out in your own words briefly.

2/ You link this note to a relevant topic in your existing set of notes (’slip-box’). For example if you have read something interesting on investor returns and you already have an existing set of notes / card on IRR and its issues then add it to that cluster. While adding if you see a contradiction or reinforcement of what you already have, you could write about that too in your note. (Sometimes your note may be the first of a topic which is also fine). Niklas Luhmann says that because each new note added can connect to existing ones, the slip-box becomes more useful over time.

3/ Over time these clusters of notes on various topics build up, then at some point, you can use those notes on a specific topic to write out a paper or essay or book on the topic. That way, the author says, no one has to start with an empty page. This is one of the fundamental points made in the book; that there is a certain amount of what he calls pre-writing before the writing and that pre-writing is the act of writing out these permanent notes and cross referencing to each other in your slip-box.

The above is the gist of the book; Sonke Ahrens takes over 200 pages to explain this but the above is the essence.

If you liked this, and wanted to read more stuff in this vein, check out this piece by Ryan Holiday on his notecard system (inspired by Robert Greene of Mastery, 48 Laws of Power fame).

Podcasts

1/ Talk: How to Speak, by Patrick Winston – January 2018

Link. Transcript. AI Summary.

Strictly not a podcast but a talk by MIT professor Patrick Winston on how to speak and present better. This is I believe a popular talk at the university. I got it transcribed and fed it to Claude to get the summary and it made for useful reading. I loved his framing of “your ideas are like your children do not let them go out in rags”. Clothing / packaging the idea is important and to this end he introduces a few concepts and frameworks such as Winston’s Star (5Ss = Symbol, Slogan, Surprise, Salient Idea, Story) that he suggests to keep in mind when creating a presentation or a long piece of work. Then comes what he calls presentation heuristics such as cycling (revisiting the idea multiple times given distracted audiences), outlining the idea in advance, and enumerating the key points through the talk etc. Lots of useful concepts and tactical ideas (e.g., don’t present to a dark room, avoid laser pointers etc., with explanation) that will help anyone who offers talks regularly and / or wants to improve their presentation / talks.

2/ Gokul Rajaram on Colossus’ Invest Like the Best w Patrick O’Shaughnessy – January 2026

Link. AI Summary.

Gokul Rajaram’s podcasts are, as always, a pleasure, with so much to absorb from him. This one covers his learnings from overseeing product at Google, Facebook, Square, and DoorDash, and now in his role as an advisor and investor. It covers a bunch of interesting topics.

One of the most fascinating things is how he looks at product management as managing the interests of both customers and the business, and how he says outcomes are fundamentally about behavior: from non-customer to customer, and from customer to customer. Driving this is really the goal. See every feature in terms of what behavior it is trying to enable, and he says that if it’s not enabling one of these behaviors, then you should rethink whether the feature is needed.

Then there’s an interesting passage on how to communicate to the team, and he describes how this becomes important as the company scales. He describes the format for a weekly email that the founder can send, consisting of three sections: Top of Mind; Performance Update, which is really around the business as well as any product updates; and finally Miscellaneous, whether it’s on the team, any news, things like that.

Thirdly, he cycles through a bunch of topics. There is his perspective on ad businesses, given his experience running them at Facebook and later at DoorDash. He describes three types of ad businesses: first, first-party businesses like Facebook or Uber; then businesses like AppLovin, which drive outcomes for owned inventory; and finally products such as The Trade Desk, which control or are the exclusive provider for a large source of demand. There’s a fascinating insight in this section, with a bunch of very interesting points he makes on how increasing advertising will impact user engagement, and how this trade-off has to be handled carefully, including a hack to make sure you’re not overdoing it by creating a holdout group that never sees ads, so you understand the impact of showing ads.

There’s also a brief discussion on careers in the AI age, where he says roles are going to break into IC roles or manager roles, and that you will typically start seeing the span of control widen. He says the number one skill will be becoming a functional expert who can build and orchestrate an army of AI agents for that function. He also describes how we should assess candidates in today’s age: just as engineering gives coding assignments on a whiteboard, we should give them actual work projects. If it’s a corporate development person, ask them to figure out a company to acquire; if it’s a marketing person, ask them to get X number of people for a certain budget, and so on.

There is also a very interesting discussion around how he sees that people are confusing SaaS companies that are systems of record with SaaS companies that are utilities, and how the former have an intrinsic advantage. Sooner or later, he says, people will understand that they have unfairly devalued system-of-record companies such as Salesforce. He then describes how these companies are rapidly racing to build agents, even as AI-native companies are trying to bite out of the system-of-record companies.

Fascinating insights from an elite operator in the Valley, someone who has seen large companies and highly successful products get built out at scale, and who is now parlaying that skill set into becoming an advisor, investor, and mentor.

3/ Charles Hudson, Precursor Ventures, w Turner Novak – June 2026

Link.

A bit late to this excellent podcast episode; recommended for anyone operating in the preseed / seed market. Felt it was one of the more honest conversations about how seed / venture actually works right now, not how it’s supposed to work. Hard to easily distil / summarise as a lot of the value is often contextual rather than immediately actionable. Well worth the listen / read to understand how the US seed market evolved and what we are likely to see in India (as the structural forces that drove this in the US are present here as well; though a tad muted / smaller). A few notes I made while reading:

1/ Multi-stage funds beginning to dominate seed as well: From ~2010 to 2018, the prevailing founder consensus was that taking a seed check from a multi-stage fund is dangerous: if they don’t lead your A, it was signalling risk. The narrative flipped around 2018, driven by repeat founders who’d grown comfortable with the signalling risk. But the deeper point is structural: in a world where AUM is the dominant success metric, funds supersized to run a tip-to-tail multi-stage strategy, offering deployment as a service to their LPs, and thus built permanent seed products. This, Hudson says, is the single biggest structural change to seed in the past decade, and reduces the degrees of freedom for a pure seed found to operate (harder to get exclusivity on top tier founders).

2/ LP’s rational case for consolidation: deploying $100M through 10 seed managers at $10M each requires ~200 manager meetings to identify those 10, then 10 AGMs, 10 LPACs, 10 re-up decisions. Consolidating into two multi-stage firms offering tip-to-tail coverage is rational provided these have brand and access. This is a very rational decision led by LP capacity constraint and is leading to supersized multi-stage funds, and struggles for pure seed funds / emerging managers.

3/ Perma privates: The secondary market has matured to the point that the top 15 companies have near-public price discovery: any secondary buyer can quote you Databricks, Stripe etc. Hudson coins “perma privates” for companies like these: regular liquidity windows, transparent pricing, functionally no need to go public. The consequence for VC fundraising is that if your fund contains a name that trades actively in the secondary market, LPs can anchor to a price and a narrative. If you hold unknown early-stage companies, you’re asking LPs to hold an abstraction. This changes what actually gets rewarded in LP conversations, and it further concentrates attention on the top 25 names where there’s at least an active market.

4/ Series A valuations are strongly correlated with value: An LP who also invests in a large multi-stage fund ran the data and shared the finding with Hudson: for companies that ultimately succeeded, the price paid at seed shows no consistent pattern: some were very cheap, some very expensive. At Series A, there is a strong price-quality correlation. The good companies are uniformly expensive. By the A, enough is known about the business that quality gets bid up rationally. Implication for everyone: the information content of a high Series A price is real: expensive As have historically been the good ones.

5/ Stage names are losing meaning — and seed managers have been slow to update. Hudson began his career when stage names implied lanes: seed investors in seed, Coatue in Series B. Those lanes no longer exist. But his observation is that dedicated seed managers as a group have been slow to realize they can target their required cash-on-cash returns at later entry points. He invokes Keith Rabois’s Stripe investment at a $1B valuation; “nuts” at the time, now considered prescient. For companies that are genuinely working, getting onto the cap table even off-model is worth doing, both for the return profile and because it generates market intelligence not visible from the outside.

6/ Sitting out a bubble is as dangerous as joining one. You have to play the game on the field, not sitting in the stands. The sober managers who passed on 2021 froth got no LP credit for restraint. The corrective force most people assume exists — “bubble-chasers lose their LPs” didn’t transpire at all for the top funds. Hudson’s conclusion: if your goal is to remain a venture capitalist, the rational move during a speculative frenzy may be to participate even under deep personal skepticism, because LP attrition from missing a cycle is a harder problem than cleaning up from a mostly-wrong bubble bet with one right call in it. The managers who went deep and caught one Anthropic-scale winner (he references Menlo Ventures here) reset their entire firm narrative regardless of what else they did.

7/ The Principal investor program: Precursor gives new team members a fully discretionary 250–500K budget, writing 25–50K checks independently; no partner sign-off. The logic: requiring approval corrupts the signal, because the junior filters for what they can sell upward rather than what they actually believe. The budget generates ~10 genuine yes-decisions; check sizes escalate with each fund to test whether the person can win comparable cap table access with a larger, more competitive check. The only terminal states are partnership or an honest exit. Most platforms give juniors no check-writing until year five or six, then hand them $5M. This format is much much better.

4/ Elon Musk w Dwarkesh Patel and John Collison on Cheeky Pint – February 2026

Link. AI Summary.

Dwarkesh and John Collison interview Musk on why he thinks data centers should be built in space, and his take on the AI x hardware landscape. Really good insight into how availability of power as the key rate limiting factor on compute deployment influences / is behind Musk’s decision to evaluate data centers in space. All of this is fascinating, but to me the key ‘through-line’ of the podcast was the concept of the ‘limiting factor’ - it comes up multiple times. To read / hear this is to understand how Elon’s mind works. At every point he has a sense of what the limiting factor for progress is, and he identifies that lever and jumps on that.

For instance this is how he deconstructs nested limiting factors in compute: Compute is limited by power limited by regulation limited by gas turbines in turn limited by blades - says only 3 companies in the world make these gas turbine blades and are massively backlogged. Then there is his take on memory chips as bigger limiting factors over logic chips, or ASML over TSMC. The clarity is fascinating to see.

As Elon puts it: “Speed is important....I just repeatedly tackle the limiting factor. Whatever the limiting factor is on speed, I’m going to tackle that. If capital is the limiting factor, then I’ll solve for capital. If it’s not the limiting factor, I’ll solve for something else.

Another: “I actually allocate time according to where the limiting factor. Where are things problematic? Where are we pushing against? What is holding us back? I focus, at the risk of saying the words too many times, on the limiting factor.”

Founders should take note - at any point focus on the limiting factor. Keep moving from limiting factor to limiting factor. Reminder: it may not always be the most current urgent thing / emergency. That probably is being handled by a relevant team member. It could be something that will come up in future, like a 2nd factory that you have to align on now, or fundraising because it will constrain growth in future, or regulation or so on.

5/ Jeremy Giffon on Colossus’ Invest Like The Best w Patrick O’Shaughnessy – July 2026

Link. AI Summary.

I really enjoyed the last Jeremy Giffon x Invest Like The Best episode and did enjoy this one hugely too. Covers his thoughts on venture, private markets, and his take on tech du jour. What stood out to me:

a/ Venture funds take a long time to see results so what they are selling in the interim (to their LPs) is narrative. Storytelling ability is key.

b/ The most successful organisations of today are timeline-native (”they are constantly monitoring the timeline, and reflexive in that its actions then affect the timeline, which it then sort of reads and reacts to”. Interesting observation on how the new and successful set of recent politicians (Trump, Mamdani, AOC, from U.S., and likely even Modi) are highly reactive and reflexive to the timeline. “Ben Sasse, the former senator, has this great notion that Washington is now mostly people who want to be TikTok and YouTube stars, which is mostly what congressmen and senators want to be. The people who do well in politics now are just optimized for content. They’re basically content creators, because the polling is the timeline.” Really clever insight.

c/ “posting is the last great meritocracy”; irrespective of your stature or follower count, a great post can get you in front of the Interwebs.

d/ ‘Billionaire inflation’ is now underway; for a while they have been the priestly class, but increasingly they are now deferential to the ‘posters’. Jeremy: “Posters who are dictating what the timeline thinks of something is a really, really small group. If the original vision for who voted was white male landowners, maybe the version of people who matter for policy now are the good posters.” The billionaire class is now increasingly subservient to the posters. “I was at this thing a while ago and it was a bunch of billionaire investors and they were all fighting over who could sit next to Tyler Cowen because he’s the most interesting person there.”

e/ Allocation in the hottest private companies is the scarcest commodity today and anyone who controls access to this allocation is powerful and wealthy. “Elon, Zuckerberg, Dario, Sam — they can sort of make landed gentry by giving out allocations, because these allocations are these best examples of generational wealth. You get this allocation in SpaceX or in Waymo or whatever.... And then you get to go out and basically say — I’ve been given a deed; the king has given me 500 acres in his country, and Elon has given me $100 million to allocate in SpaceX — and then you get to go out and charge fees and make a bunch of money from it. Do you have allocation? 6/ How to write JDs (job descriptions) better: a good disqualifying statement is key - one that is open to interpretation and slightly provocative is key. It should say who it is not for, but the qualifying criteria should be open to interpretation e.g., “you’re an ideological minority at a top 10 school”.

Probably lots more I left out like ‘billion-dollar pdf’ etc. Highly recommended; wide-ranging podcast episode that covers tech, ideas, and culture. Doesn’t button hole itself into one category neatly like the best epsiodes do.

6/ Michael Pollan on How I Write w David Perell – June 2026

Link. Excerpts.

Michael Pollan is one of my favourite non-fiction writers, and hence this episode was a treat. Lots of extremely useful mental models and frameworks for writers or wanna be writers covered in the episode. In particular I loved how

• Pollan rewrites his previous days’ writing every morning before he starts writing. This, he says, puts him in the printer camp of writing (where everything emerges correctly line by line like a printer) vs the pixel camp (where the image pops up and then sharpens in resolution - this is getting the entire rough draft out, and then refining the whole thing)

• How Pollan’s early writings in gardening were inspired by the English and American gardening writers he read, who mostly wrote in first person letter-writing / epistolary mode, and that stayed with him and became his writing style - “an ‘over the back fence’ conversation, very familiar, talking directly to the reader.”

• Shares a riveting example of how he paid for a steer that was headed to slaughter, and this gave him a more involved view of the ranching to slaughtering process, including how the ranchers make decisions around livestock.

• The ‘laundry line’ metaphor for how he structures his writing / books. The line or string is the narrative arc + timeline, and the laundry are the specific topics you will dwell into. He puts it: “You need to space it out because if you clump it all together, it sags. Exposition is less appealing to the reader than the narrative. We constantly want to know what happens next. In this specific case, readers know the animal will be killed in a slaughterhouse and are curious about that process. This curiosity acts as your suspense principle. You can depart from your laundry line for a period to provide exposition—to explain the feed, why corn is used, what that means, and how it’s grown with fossil fuel, in contrast to grass grown with sunlight. However, you cannot stay away from your narrative for too long. You must cultivate a sense of when your reader will grow impatient. While you could go on forever with exposition, you always need to return to your narrative.”

• The importance of the introductions section in the non-fiction book: how the best you can do there is to set expectations about the book, what it will be and won’t.

• How to use conflict (between two protagonists, two camps) to create tension, and drive narrative. And David Perell’s framework about understanding a field / profession through the dominant civil wars / big arguments /different camps within it.

• Writing is thinking - the process of writing is generative helping you discover new things about the topic and new ways to approach it as you write. Pollan says” “Often, I have only a general outline of where I want to go, yet I discover new ideas and metaphors in the course of writing. ...Writing does something unique to your brain; it grants access to thoughts and connections you wouldn’t find just by walking, thinking, planning, or outlining.”

• Writing is hard, and it doesn’t get easier ever. Michael puts it well: “Unlike woodworking or playing an instrument, which can become second nature, writing remains challenging even after doing it professionally for 40 years. Every time you face that white screen, you wonder why it doesn’t come more easily....I still struggle every time I sit down to write, even playing games with myself about how much I need to produce before earning a snack.”

7/ Brian Chesky on Colossus’ Invest Like The Best w Patrick O’Shaughnessy – May 2026

Link. Excerpts.

Enjoyable podcast, with something for everyone. My favourite parts were Brian’s elaboration of 1) what he calls the 11-star experience, and how they strive to offer this at Airbnb, and how other brands can use this framework to enhance customer experience 2) how he has prioritised recruiting - the recruiter is the first and last call of the day, he even helps hire for his executives, and how he hires by building pipelines.

There is a lot else as well, including how his passion for bodybuilding gave him lessons for life as well (”If you can change your body, you can change your life”) and why he is very hands on early with his execs and only gradually lets go (because he doesn’t want them to develop the wrong muscle memory early on).

Articles

1/ What I’ve Learned From Selling 500,000 Books, by Tiago Forte – 15 Jun ‘26

Link.

Tiago Forte, productivity and note-taking guru, creator of the ‘second brain’ concept, writes about his learnings (and earnings) from book writing in a candid look at his book-writing career. Interesting for any would-be non-fiction writer, but also useful for anyone who finds these topics interesting. What stood out / my summary:

a/ It took 2y 4m for Tiago to break-even on the book’s expenses

b/ Interesting visualisation of non-fiction idea books as global reader-funded marketing campaigns. Very very few books make you money from selling copies. Instead what books do is give you deep attention from readers. And much of your expenses towards reaching them is subsidised by their purchase of your copies. Given that books are not directly income-generating assets so much as attention-capturing assets, it works best when you have a natural next step or follow-up product for the readers to explore, after you have got their attention. This follow-up product could be a consulting gig, a course, and so on...

c/ The best next product is whatever addresses the reader’s problems (that led them to read your book) in greater depth than your book did.

d/ (In my view) I think one mistake Tiago made was not exploring creating a Second Brain / Note-taking app. This could have been a natural next product.

2/ ‘Religion as Software’, by Tomas Pueyo – Jun-Jul ‘26

Link 1. Link 2. Link 3.

The most interesting product mechanics / growth writing today is Tomas Pueyo’s writing on seeing religions as products. (warning: paywalled). Very interesting comparison of how Islam / Christianity are designed for growth (as opposed to a Judaism for instance), and how that manifests itself in ‘product adoption’.

3/ Donald Knuth on work habits, problem solving, and happiness, by Shuvomoy Das Gupta – 13 Apr ‘20

Link.

Donald Knuth is the famous computer scientist who doesn’t use email (at least that is how he is registered in my head). Knuth’s deep work focus has always fascinated me, and I thus enjoyed this look by a computer scientist + mathematician Shuvomoy Das Gupta on Knuth’s ways of working. I really liked the following

• Knuth: “I schedule my activities in a somewhat peculiar way. Every day I look at the things that I’m ready to do, and choose the one that I like the least, the one that’s least fun — the task that I would most like to procrastinate from doing, but for which I have no good reason for procrastination.”

• Knuth’s take on keeping a high minimum, for he says “I think that the limiting thing — the thing that determines a person’s success in life — is not so much what they do best, but what they do worst....If you can do something really well but there are other things at which you’re failing, the latter will hold you back....A person’s success in life is determined by having a high minimum, not a high maximum”

• Interesting take on happiness, and why he feels the body is programmed to be unhappy / depressed a certain percentage of the time (led by chemical / hormonal factors he says).

4/ How China’s Venture Ecosystem Works, by Bohan Lou

Link.

Interesting piece on China’s venture ecosystem and how it differs from the US VC ecosystem - onerous terms (’ostensibly equity, in reality debt’) that force the company to list early as startups are committed to return a certain hurdle rate in a defined time period, the lack of an M&A market, heavy intermediation between startups and VCs by investment banks (termed as Financial Advisors), the heavy hand of the state in pushing funding in certain desired directions etc. India is a lot more closer to the U.S. position it seems.

Bye!

It is time to wrap this! As I shared earlier, you should think of this substack as akin to a monthly magazine - you don’t have to read it all in one sitting, and you don’t have to read all of it! Feedback, or your own ruminations are welcome. Please use the comments section to engage!

Regular readers know that this newsletter has two permanent sections:

• Writings - where I usually write and / or refer to one or more original pieces that I published in the previous months, typically about venture or the startup ecosystem.

• Readings - about what I read and learnt about. My reading diet is tilted rather heavily in favour of books and podcast transcripts, and against articles / newsletters. This will naturally reflect in the reading list.

This is a long newsletter - think of it as akin to a monthly magazine from me (only the frequency may not be monthly!). I don’t know if you can read this entire newsletter (and peruse the links) in one sitting, and even if you do a second run (which I very much doubt), you will have to pick and choose what to focus on. A good way to read this newsletter is to certainly read my original writing(s) below, and then glance through the rest and pick 1-2-3 items that pique your interest. Anything more is a bonus!

Writings

1/ I wrote a review of Akshay Jaitley’s book on Trilegal which he cofounded 25 years back. Utterly fascinating look back, and one that is extremely candid and honest, laying bare the challenges and iterations that Trilegal went through, including internal conflicts and divisions, to emerge as one of the leading law firms in India today.

2/ I recently made an appearance on economist Vidya Mahambare’s podcast ‘What Shapes Us’. The podcast covers how the 5Es as terms it – Endowment, Environment, Education, Effort, and Equality of Opportunity – shape our lives and careers. It is perhaps amongst the most transparent and candid public conversations that I have done (of a kind).

Link to the podcast / video below; for the complete transcript of the podcast click here.

Readings

Books

I was able to keep reading going, despite the challenges of the relocation and the disruptions caused by it. That said, fiction took a backseat this last two months unlike the first two months of the year when I was able to get in more fiction. The goal going forward is to reset the mix.

1/ Plain Tales from the Raj – Charles Allen

Slice of life stories capturing the diverse perspectives of British residents in India – administrators, soldiers, and their wives – during the latter half of the Raj (1900s to ’47). Interesting and enjoyable. Albeit many passages would be considered ‘politically incorrect’ today, but of course reflects the attitudes of that era.

2/ Runnin’ Down a Dream – Bill Gurley

I read it because Bill Gurley wrote it 🙂 At 51, and happily ensconced in venture capital, this is not the book I needed to read! But then, am not the target audience for the book as well. The book is titled after a Sep ’18 speech he gave at the MBA program at the University of Texas, listing five key principles for finding (and thriving in) a career you love. The speech / video went viral on the interwebs. The book is an expanded version of the speech – there are more stories and profiles, and there are six principles now. There is also a (brief) chapter on how he arrived at his career which was my favourite part of the book. If you are in the early part of your career, then this is a good read I would think; otherwise not. And even for the career starters, perhaps the speech is a better place to begin.

3/ Trilegal – Akshay Jaitly

A look back at Trilegal’s founding and its journey over the past 25 years. This is a great read for any lawyer but it is also useful for folks from other professional services firms such as consultants or even VCs / PEs. VCs and PEs of course have their own carry mechanism for reward-sharing, but there is still a lot here that they can borrow and learn from this book. Recommended.

Click here for my review of the book.

4/ Buildit – Albinder Singh Dhindsa

Overall, a disappointing read. For obvious reasons, it felt like he couldn’t be as candid as he could be about recent years, and the competitive landscape, and the turn of events which led to Zomato acquiring Blinkit, and then the subsequent pivot to 10-min delivery and then success. Perhaps he should have waited a few years to write the book! The first 100 pages where he depicts his personal journey to founding Grofers (which Zomato / Eternal acquired, and became Blinkit) is the best part of the book, including a long but highly readable and illuminating section on labour issues and labour psychology in Chapter 2014. Some additional segments which stood out were the pigeon-poop problem they encountered and the eventual surprising solution to it (pgs 84–87) and then a brief segment on how he personally had to deliver himself (while facing a labour mutiny) in 2014, in the early days of Grofers, which he describes as one of his toughest days to get through.

5/ Biting Off More Than I Can Chew – Rahul Akerkar

Rahul Akerkar created Indigo, a stand-alone fine dining restaurant, in Mumbai in 1999, which is widely seen as one of India’s most innovative (and successful) restaurants (shut down after 20 years). Indigo spawned a successful sub-brand Indigo Deli, which became a chain, and along the way Rahul lost control of his restaurant chain, due to poor financial management, and cost-overruns in an ambitious project called Tote on the Turf. The book is an enjoyable read, mixing personal memoir, his business journey through the various restaurant projects, and finally his favourite recipes, all in one package. I would think this was an expensive book to produce – given the colour photos, the illustrations, and the rich paper stock. That said it was a tad dissatisfying as I felt it fell short of being a great autobiography. Perhaps it is because Rahul couldn’t be truly honest about the business challenges; he says in an interview they had to chop off 100 or so pages for legal reasons. I felt Rahul missed an opportunity in using the book to look back at the core reasons why Indigo / DeGustibus (the overall entity) didn’t succeed financially and that would have been illuminating to future restaurateurs. Still a good read if you are into food / food culture in a big way.

Podcasts

1/ Vinod Khosla & Keith Rabois, Khosla Ventures, on Uncapped Podcast w Jack Altman – January 2026

Link. AI Summary. Transcript.

This podcast will mainly appeal to venture nerds, the kind who have listened to or read several podcasts by Vinod and Keith, and are excited about them coming together, and will consume this too. Like me!

A few points I found particularly interesting:

• How their Monday meetings start with portfolio discussions, and only later move on to investment committee discussions or pipeline discussions. That was fascinating.

• Their framework for evaluating founders. I thought that was interesting. A+ incomplete is the broad name I would put this under. It means you can be A+ on some dimensions, and it is okay to be less strong or incomplete on others. You are hoping they will learn faster and catch up on the areas where they are weaker, e.g., they could be technically massively brilliant (one of the top two or three in that field), and that they will catch up on business as well. Looking for a very rounded personality is likely to lead to passing on several good factors.

• How they looked at OpenAI and saw it as enormously talent-dense, comparable to Google or DeepMind, which led to their decision to back them.

• That they will not invest in human-in-the-loop or co-pilot AI companies. They want to do entirely agent-like AI companies. Overall, a fascinating episode.

Monday meetings: Critically, every Monday meeting begins with the current portfolio before any new opportunity is discussed — a deliberate signal that they are in the “build the company” business, not the “pick the company” business.

Venture assistants, not capitalists: Vinod says “In 40 years that I’ve done venture capital, I’ve not once called myself a venture capitalist or an investor. I always say I’m a venture assistant to entrepreneurs trying to build companies.”

What makes a great founder, and what they look for in founders Keith’s framework: he’s looking for founders who are top-one-basis-point on some dimension: smartest, most tenacious, best people-assessor, most strategic, or, alternatively, a rare Venn overlap of traits not commonly found together. Keith: “I’m trying to find out: is there a non-zero chance that this person can change a vertical over the world?”.

Keith cites Max Levchin (Reid Hoffman told him in December 2000: first-rate technologist and first-rate business mind — fewer than five people in Silicon Valley qualify) and Jack Dorsey (design + tech + strategy = three traits).

Vinod adds: learning rate and the ability to reject bad ideas matter as much as raw capability. He deliberately takes positions he doesn’t believe to test how a founder thinks. Vinod: “If a person listens to me all the time, I’ll almost never invest with them. I know they’re not critically examining.”

The conversation goes deep on how to surface non-obvious founder traits in a meeting. Keith doesn’t do structured biographical interviews (the “Doug Leone style”) — he prefers freeform meetings where passion and drive “just show up.”

Vinod’s interview philosophy: put people in situations they haven’t been in, because good storytellers may not be the best candidates. He has a public document on how to interview and a private one on how to interpret answers. Vinod stresses that “A+ incomplete” — exceptional on key dimensions, acknowledged gaps elsewhere — is the formulation he most values. Learning rate is the hardest to assess from a single meeting.

Vinod and Keith discuss what a founder cannot be deficient in: ethics, unambiguously. They note that highly disagreeable, intense founders often actually have the strongest moral compasses — their intensity is rooted in principle.

Investing in OpenAI: The OpenAI investment story is the centrepiece here. In 2018, KV made its largest-ever initial investment — twice the prior record — in OpenAI when it was a nonprofit with no product plan and no revenue plan. Vinod: “Outside Google and DeepMind, this was the only critical density of research-grade people that could possibly pull off AI. That was the investment hypothesis in a sentence.” Knowing Sam Altman over a sustained period (Vinod, David, and Keith all did) helped them see the lines clearly.

KV (Khosla Ventures) sent an apology letter to LPs at the time of investment — “we know it makes no sense but we’re doing it anyway” — and that letter is now part of their fundraising deck.

Investment themes at KV: The conversation turns to AI investment themes. KV has ~30 portfolio companies building AI workers across oncology, mental health therapy, chip design, structural engineering — “as many professions as there are, there’s that many opportunities.” A deliberate decision made ~3 years ago: avoid co-pilots (humans in the loop slow things down), back AI doing the work entirely.

KV and fintech: The discussion moves to KV’s fintech track record — a less-known strength: in every single fund, one fintech investment has returned the entire fund. Examples: Square, Stripe (second investor), Affirm, Avon, Upstart. Avon is flagged as the next potential iconic fintech: using AI to issue a home equity line of credit and consolidate credit cards in one hour (normally weeks).

2/ C Thi Nguyen on Dialectic w Jackson Dahl – January 2026

Link.

Lots of interesting ideas and concepts here in this podcast episode featuring philosopher C Thi Nguyen in convo w Jackson Dahl on the Dialectic podcast. The broad theme is that scoring systems, as seen in games, are fundamentally ways to guide our attention to what matters. But the same scoring systems that make games interesting e.g., in football, for instance, you have to score a goal without using your hands, can be dangerous if adopted wholesale in life.

The problem is that scoring systems in real life, which typically take the form of metrics, are designed to strip out subjectivity, judgement, and even agency from the players. All such scoring systems or metrics, however seemingly objective, are built on value judgments. Evaluating charities by efficiency of spend, for example, implicitly assumes that all charitable causes are fundamentally similar. But in certain domains, achieving spend efficiency may be structurally harder, due to missing baseline infrastructure or other contextual factors, and penalising those charities for that is a judgment call, not a neutral measure.

To me, the core takeaway was that when you encounter any incentive structure, or look at the underlying scoring system or metric, go deeper. Understand the value judgments and assumptions baked into its design.

3/ Susan Orlean on How I Write w David Perell – October 2025

Link.

Enjoyable read on how a master non-fiction writer goes about her craft.. I liked especially the part around how she uses index cards – as many as 700 of them for a book – which makes it possible to move them around and arrive at the book’s structure and narrative arc.

4/ Andrew Reed on Dialectic w Jackson Dahl – February 2026

Link. Excerpts I found interesting..

I first came across Andrew Reed from a post by Pat Grady where he described how Andrew keeps a ‘pristine calendar’ limited to the highest quality founders, and thus being able to carve time out for them. I was intrigued, especially given Andrew’s impressive track record (Figma, Vanta, Robinhood etc.) and tried to find more about Andrew but alas there was very little on him, including it seemed no podcast appearances. So when he finally broke his ‘podcast celibacy’ on Dialectic, I dived in. I enjoyed this one; it is an especially good podcast for us venture nerds, though less interesting if you are a founder.

Lots here that I found interesting including 1) why if you have to do DCF or too much quant analysis, it is probably not a good deal 2) why you’ll truly understand the business you have backed only after you invest and attend the first board meeting and 3) (hence) why the next round after you invest is the hardest. Recommended for venture investors.

5/ Chris Hohn on In Good Company w Nicolai Tangen – May 2025

Link. Transcript. AI Summary.

The Chris Hohn podcast with Nicolai Tangen of Norwegian sovereign investor NBIM was amongst the most interesting transcripts I have read of late (Pair it with the FT article on Chris Hohn).

Chris Hohn is a legendary investor, runs the most profitable hedge fund in the world, with a hyperconcentrated portfolio (15 cos across $77b AUM) selected for their pricing power (ability to price above inflation).

What I found interesting was their extremely constrained top of funnel (TOFU) of 200 companies that are quasi-monopolies or have limited competition / high barriers to entry. Nalanda in India has a similar constrained TOFU of 75-80 companies (filtered via ROCE, durability of revenue, ease of understanding, and governance). As w TCI / Chris Hohn’s investing strategy, they too try to hold for ever.

I dont think all great investors have such hyperconstrained TOFU but interesting to have these explicit filters.

6/ David Gelb on How I Write w David Perell – April 2026

Link. Excerpts I found interesting..

‘Jiro Dreams of Sushi’ is one of my favourite works of art. I have watched it several times, and each watching tells me something anew, about how to live a meaningful life, of purpose and striving, and how to do great work. I am perennially grateful to David Gelb for creating the documentary. Thus, to me this episode where David Perell interviews him held great allure. And I wasn’t disappointed. It is a really good one; while David Gelb operates in the visual medium, there is a lot of good writing that underpins a visual artifact. So if you are keen to improve your writing this is a good episode to learn from.

Broadly, David Gelb says great cinema or writing is about people. Even when it is about ideas, it is really about the people behind the ideas. People, he says care about people, and therefore he has always put character first. Importantly, he says at the core of every character is their origin story. More than how a chef does his work, it is really why he does his work that is important. He says: “Character and emotion are much more important than information. In Chef’s Table, you will not learn anything about how to cook. But you will learn about why they cook. That’s why the show has lasted because it’s about character journey. It’s not about facts.People care about people, and that’s what hooks you, and that’s what makes you remember things. We remember information because of the emotional context of it.”

A few of his other takes that stuck with me.

• Every scene should see a change in a character. “If nothing changes, the scene won’t work.”

• ‘False victory’ is an element that comes in a lot of great movies, like in Titanic where Rose and Leo are falling in love, and everything looks great, but the ship is sailing towards the iceberg.

• A great way to get feedback about a movie / documentary, especially on pacing, is to watch it with another person. You yourself will feel it if the pacing is slow.

Subscribe now

7/ Bill Gurley on The Tim Ferriss Show – December 2025

Link. Excerpts I found interesting..

Good intro to the themes covered in Bill Gurley’s book ‘Runnin’ Down a Dream’ (which I read and shaed my views on above), about how to find your way into a career that you love, and thrive in. The title of the book comes from the title of a speech that Bill Gurley gave at the McCombs School at the University of Texas covering similar themes. You should definitely read or watch that speech.

8/ Fred Wilson w Michael Mignano on the USV Youtube Channel – April 2026

Link. AI Summary.

Fred Wilson is a legend, and it is always illuminating to consume a podcast appearance or interview by him. This was a really good episode for not only do you get a lot of colour on Fred’s journey – from his entry into venture, to setting up USV – but you also get his perspectives on how he sees venture in the age of AI. The highlight, I thought was his pov on the three jobs that remain for humans in a venture fund following AI. The other jobs can all be automated away using AI. He says: “If I was starting a venture capital firm today from scratch there’s only three things that I would be focused on the humans in the firm doing: high-level thesis development… building relationships with the founders… and working with the founders after the fact. Everything else I think we can automate with AI.” Recommended for venture nerds.

9/ Rama Bijapurkar on Konversations with Kushal w Kushal Lodha – June 2026

Link. Transcript. AI Summary.

For regular Rama-watchers or readers, especially if you have read Lilliput Land, there is strictly nothing new here. That said, still an interesting one to listen to / read the transcript of, both for the macro perspectives and consumer insights:

Macro: 1/ Indians are “fueled by agency, but failed by structure”

2/ India doesnt have a large middle class – there is a sliver of India which has the ‘resilience’ as Rama says to absorb income drops. She describes 5 levels of population classified across income brackets: L1 to L5 in the order of affluence and resilience. The true resilient classes are L5 (~25m people with annual household spend of ₹~11L+) and L4 (~70m with annual spends of 5.5-7L. The next three classes L3 (annual household spends of ₹3.8 – ₹5.4L, ~200m large), L2 (annual household spend of ₹2.2 – ₹3.8L, ~430m, and the bottom-most L1 (~700m large with annual household spend of ₹1.1 – ₹2.2L) have very low levels of resilience and savings, and are one crisis or job-loss away from dropping down further into poverty.

3/ India is a large mass with slow acceleration; it morphs, not molts, i.e., doesn’t shed its skin.

Insights: 4/ There is a chaiwala at the Ahmedabad airport she says who charges ₹5 with sugar and ₹8 without (correctly reading that sugar-avoiders are more desperate and will pay a premium).

5/ Consumption data is “maternity (certainty) vs. Income data is “paternity” (opinion), because if you multiply stated incomes by the number of people said to earn them, per her you routinely exceed India’s GDP. She urges looking at consumption proxies — how many households have a car + PC + microwave (she says ~4%) vs. two-wheeler + colour TV + fridge (much larger).

10/ Eric Ries on Lenny Podcast w Lenny Rachitsky – May 2026

Link. AI Summary.

Interesting podcast not so much around startup operating mechanisms as much as how to ensure that your organization’s original mission orientation can endure, and how you need to set up specific mechanisms or apparatus as Eric Ries says to ensure this. Eric says that after a company lists there is pressure from investors to dilute the original mission and increase margins either by using cheaper ingredients by drifting away from certain ethical sourcing processes etc., or increasing prices etc. He suggests organizations recasting themselves as public benefit corporations (PBC); this should be done as early as possible he says. For instance Anthropic is a PBC. This, Eric says, will protect the founders from any challenges in the future as they can say that anyone who agreed to invest in this co signed up for the charter. He says bake mission orientation into the Charter itself and describes this as the best way to safeguard the company’s original mission and values. Through the podcast he gives interesting examples of such companies Cloudflare, Novo Nordisk etc.

Two interesting and related takeaways: 1/ Eric says commitments and apparatus beat intentions (the apparatus to produce the quarterly report ensures it comes out on time always, so similarly if you want to ensure 100% mission adherence you have to set up the apparatus like PBC to ensure it happens. And if an org is highly mission-aligned it will also be able to move fast (mission alignment is one reason Anthropic ships so fast, Lenny says). 2/ The other useful concept I took away was the culture bank framework: every action of yours should be a deposit in the culture bank where you take a costly action that defends your org’s values (e.g., H-E-B employee allowing customers to take goods away on credit during an ice storm when their POS system was down, instead of shutting the store). Never do the opposite, says Eric Ries, a withdrawal from the culture bank which is an easier albeit logical extractive action (e.g., taking prices of baby foods up during a shortage etc.)

Articles

1/ Reluctantly Influential: Inside Lenny Rachitsky’s Demandingly Chill Life – Nate Martins – April 2026

Link.

Fun read on Lenny Rachitsky, who has become an influential writer and podcaster covering topics around product management. I liked the article for the detail it provided on how he works, and the information it gave about how he prepares for a podcast / works on an article. The “how the sausage is made” view of that process was especially useful and interesting for me. While it also covered the broader story of his newsletter and podcast, and what life is like as a creator, but what really stood out was the part prep work around recording a new podcast and creating a new article.

2/ The Narrow Path – Lucas Vaz – April 2026

Link. AI Summary.

Amongst the most insightful articles I’ve read this year. All venture nerds will find it interesting for it takes potshots at one of the shibboleths of venture; which is that you need to have sizable ownership in a company and you should construct your portfolio such that you are able to get sizeable ownership. The author says that instead of focusing on ownership percentages, you should instead seek for position concentration, that is, have more of your funds in fewer companies. So if you have 20% of your portfolio in one company, even if it’s an expensive purchase and you do not have a sizeable position in the company (you may only have like 2-3% stake, but if it’s a category defining company then that 2-3% can be very meaningful), it is fine. Because you have invested 20% of the fund in the company this only needs to grow 5x from here to return the fund (presuming all others go to zero). Instead, if you had positions across 33 companies investing equally across them, then you typically have around 3% of the fund in each of the companies, then one of the companies should grow 33x to return the fund. His take is that ownership percentages in companies should be an output not an input to investment decisions. Instead of ‘fund size is your strategy’ it should be ‘your sourcing and winning edge is your strategy’, and you should be willing to go across stages if needed if your edge points to your being able to identify a winning company better.

3/ Pulak Prasad talk – ‘HS’ – Recd 27 Apr 2026

Link. AI Summary.

These are notes typed up by a junior investor who attended a Pulak Prasad talk. Pulak is one of the leading public market investors in the Indian market. Nothing particularly new for regular Pulak watchers or those who have read his book, but always worth hearing him restate his philosophy; the Q&A section is interesting.

The part I found most compelling was his stance on AI, and specifically his deliberate non-use of it.

Pulak’s approach is essentially the Robert Caro method: turn every page yourself. What makes this viable for Nalanda is their extremely tight top-of-funnel filter, which narrows the investable universe down to roughly 150 or so companies worth a deeper look, which then narrows further to 70–80 from which they actually buy. The learning is that if you structure your top of funnel / process tightly enough basis relevant proxies or filters (Nalanda uses ROCE as a strong filter) then you can get away without AI augmentation entirely. That was one big takeaway.

The second takeaway was perhaps the more important one: how deliberately Pulak has structured his entire investing philosophy around his own temperament and edge, with each element reinforcing the other. You can study Nalanda’s approach, even try to adopt it. But it can really only be executed by someone whose behaviour and disposition are naturally aligned with it. It is simple, but not easy.

4/ The Writer-Researcher’s Guide to Claude Code – Mario Gabriele – April 2026

Link. AI Summary.

I thought this was a fascinating article, and personally found it very useful. I suppose it would be useful for anyone who does a fair amount of researching and writing. In particular I found it fascinating to see the various tools and apps he spun up using Claude Code – such as ‘Delphi’ (and a few other agents) for research, ‘Cuneiform’ for reading, ‘Scribe’ for writing etc. Good piece to see how single-person (media) businesses can leverage AI. This will be useful for writers or those with an elaborate personal knowledge management system to see how they can leverage AI tools.

5/ What Makes Art Great? – Nabeel Qureshi

Link.

Nabeel Qureshi is consistently interesting as a writer, as he is here too, in this fascinating meditation on what makes for great art. He says great art is surprising, illustrating this through lines from Macbeth and The Whitsun Weddings, is intricately patterned (he calls it ‘echoes’), and has considerable depth. All of these are missing in the type of art churned out by LLMs he says and will be hard for AI to replicate. Ultimately he says great art is borne out and informed by our living experience, and this he says constitutes the hard and ultimate barrier that makes it difficult for AI to create great art.

6/ Why China got rich and India didn’t – David Oks – June 2026

Link.

Really good piece by David Oks on why China has grown richer and faster than India. I do agree with his thoughts (and remember a similar piece on South Korea v Kenya by Oliver Kim (https://www.global-developments.org/p/no-south-korea-was-not-poorer-than).

TLDR: 1/ China nuked its old social order and reorganised society around communist rule, and invested heavily in health + education. By 1980s when they liberalized its economy, it was “a socially modern country that just happened to be extremely poor”. There was labour / human capital that factories could leverage, unbounded by past constraints.

2/ India on the other hand had never invested as heavily in human capital nor shifted its social order. So we havent been able to take advantage of the 1991 liberalization as much as China took advantage of Deng’s easing of rules.

7/ Unreasonable Breakthroughs – Dan Gray – May 2026

Link.

Flagship Pioneering is the investor behind Moderna, who invented the leading COVID-19 vaccine. This is a good read profiling their distinct playbook as well as their founder Noubar Afeyan. The playbook reminds me a bit of Sutter Hill which too incubates companies (most famously Snowflake), but the scale at which Flagship operates, exclusively in biotech, is something to behold. They have a very structured playbook funneling ventures from ‘Explorations’ (~100 a year) to ‘Prototypes’ (8-10 each with a $1-1.5m budget) designed to maximize the learn to burn ratio, from which 6 to 8 become ‘Newcos’ which are launched. This playbook along with the ruthless focus on truth-seeking have led to a stellar portfolio outcome – 21% of ~150 portfolio companies are IPOs compared to overall industry benchmarks of 1%. Amazing. Will leave you with this wonderful quote by Noubar Afeyan, which distills their overall philosophy well: “We have to be willing to embrace unreasonable propositions and unreasonable people in order to make extraordinary findings. Because the notion that utterly reasonable people doing utterly reasonable things will produce massive breakthroughs, it doesn’t compute to me.”

8,9,10 / Three other articles I enjoyed reading

We’ve heard about podcasts’ impact on ‘dad books’ (thick history / biographies given as Father’s Day gifts). But here is Tim Ferriss talking about AI’s impact on self-help books, or what he calls prescriptive non-fiction. Illuminating.

Astute observer Anu Atluru describes the rise of Insider Media: content from VCs, startups, operators / observers. This is content by insiders for insiders she says, as distinguished by traditional coverage of tech by MSM, which is by outsiders for outsiders. Clever framing.

Terrific piece by ex-VC Pranav Hari on how the lack of sovereign models is creating a new and growing line item in our import bills, and contributing to the current account deficit. Combined with the likely drop in software services export this is likely to be a double whammy.

Subscribe now

Bye!

It is time to wrap this! As I shared earlier, you should think of this substack as akin to a monthly magazine - you don’t have to read it all in one sitting, and you don’t have to read all of it! Feedback, or your own ruminations are welcome. Please use the comments section to engage!

Regular readers know that this newsletter has two permanent sections:

• Writings - where I usually write and / or refer to one or more original pieces that I published in the previous months, typically about venture or the startup ecosystem.

• Readings - about what I read and learnt about. My reading diet is tilted rather heavily in favour of books and podcast transcripts, and against articles / newsletters. This will naturally reflect in the reading list.

This is a long newsletter - think of it as akin to a monthly magazine from me (only the frequency may not be monthly!). I don’t know if you can read this entire newsletter (and peruse the links) in one sitting, and even if you do a second run ( which I very much doubt), you will have to pick and choose what to focus on. A good way to read this newsletter is to certainly read my original writing(s) below, and then glance through the rest and pick 1-2-3 items that pique your interest. Anything more is a bonus!

Updates

Update #1: I am moving to Bangalore

Some of you know, and a few more of you have figured it out thanks to tweets like the one below or this article I wrote a while back, but it is finally time for me to depart from Delhi. After 11 years here, it is time for me to make the move to Bangalore.

This is likely the last newsletter I’m writing from my home in Noida, on the outskirts of Delhi. It’s the house I’ve lived in for the longest stretch of my life, eleven years now, and I’ll miss it dearly. One of the charms of living in this house has been the greenery in the society, as you can see here, somewhat. As the clock ticks down to our exit (in the coming weekend), I have been taking lots of walks and spending time at some of my favourite spots within the complex (yes!). Sigh.

Update #2: How AI is impacting my podcast consumption

The second update is about how AI tools, have changed the way I consume podcasts and articles now. As AI tools have improved, I’ve recently started summarising podcast transcripts via Claude and reading the summary. I tweeted about this shift here.

I’ve been thinking about whether it makes sense for me to use Claude Code to automate a workflow where say, every saturday, it would go through a certain number of podcasts, review the transcripts, and send me 5 to 10 snippets per podcast. It would be efficient for sure, but I am not sure it would be effective from the perspective of helping me absorb these insights, and internalise them. My fear of relying on an automation like this is that if it reduces the time I spend engaging with it and grappling with it, it will not stick in my long-term memory.

Here is Ezra Klein from the How I Write podcast w David Perell: “... I think that what you are doing (when reading) is spending time grappling with the text, making connections. It will only happen through that process of grappling. So, the idea that you could speed run that, the idea that it could just be summarized for you…Part of what is happening when you spend seven hours reading a book is you spend seven hours with your mind on this topic. The idea that O3 can summarize it for you, in addition to all this stuff you just will not have read, is it you didn’t have the engagement. It doesn’t impress itself upon you. It doesn’t change you. What knowledge is supposed to do is change you, and it changes you because you make connections to it.”

What I have been doing instead is to ruthlessly curate a short list of 10 or so podcasts and pick episodes from that which look interesting, and either a) download the transcript, and feed it into Claude to get a AI-generated summary or b) paste the link into my Podcast Summarizer app (yes, it was a Claude Code project) to get a slightly better but also slightly more expensive AI-generated summary. Here is what the Podcast Summarizer app looks like.

I don’t stick to just reading the summary either. While reading I pull out insights I found interesting, and then. I also ask Claude questions about the podcast to clarify relevant points. I find this interactive consumption / wrestling with the summary is better than just putting on headphones and listening while I’m on the go. This “lean-forward” style of consumption is what AI has enabled, and thus far, I feel it seems to lead to better absorption.

The final step is taking the insights I have extracted, and writing it out. I use a combination of dictating out my observations via Wispr Flow, and hand typing to create my highlights / learnings from the podcast that I can share ahead as well. Think of it as an AI Highlight or AILights as I call it. The process of grappling with it, going back and forth with the AI, and turning it into something I can share seems to make for better learning than just listening to the podcast or reading the transcript on Remarkable (my previous podcast consumption route).

To sum up, I don’t think AI has not necessarily increased the number of podcasts that I am able to consume, but it is helping me absorb these better. Still, I don’t think this is a settled position, so I’ll come back with further thoughts over the coming months on this topic.

My notes and thoughts (below) covering the podcasts and articles I consumed over the past month will reflect the above workflow. Let me know what you think of it.

Subscribe now

Writings

I wrote one piece recently. This was a short, subjective list of my recommended reads for founders; includes the usual suspects (e.g., ‘High Output Management’ by Andy Grove), but also one that might surprise you - Patagonia founder Yvon Chouinard’s’ ‘Let My People Go Surfing’.

Link: The Busy Founder’s Essential Reading List, or, 5 Books for Founders.

Readings

Podcasts

1/ Keith Rabois, Khosla Ventures, on Lenny’s Podcast – April 2026

Link. AI Summary.

Minute for minute, amongst the most insight-packed podcasts I’ve encountered of late. Lots here in this Lenny Podcast featuring Khosla Ventures’ Keith Rabois, but the following stood out and are worth noting.

1/ The first is his well-known Barrels vs Ammo framework. Keith points out that in an organization, what matters is not so much the headcount, but the number of people who can take an initiative from inception to success by themselves without intervention from the founder. He calls these people “barrels,” as distinct from headcount, which is “ammunition.” The number of barrels effectively determines the number of new initiatives a company can undertake he says.

PayPal, he says, had about 250+ people and he remembers having anywhere from 15 to 17 barrels, which he describes as an extraordinary count. When he recently spoke with Jack Altman, Jack said that at Lattice his prev startup, other than the founders, there were perhaps two barrels. That is more like the number that is typically seen he says.

2/ The second is about using reference checks effectively. Keith says he struggled to hire well at PayPal, and he found he had only a 50/50 success rate at interviews. He tried to improve the number of people he could bring onto his team by recruiting from within PayPal, and he had a better success rate there.

He realized the difference was that he was not very good at judging someone’s quality from a 30- to 45-minute interview. He could, however, get a better sense of someone over time and decide whether they were a good fit. Since PayPal only had a limited pool of people he could source from, he started looking outside and using reference checks to help evaluate someone’s quality.

He shares some interesting ideas on doing better reference checks.

– Tony Xu at Door Dash does as many as 20 ref checks on senior hires to get really accurate.

– David Sze at Greylock, an early investor in LinkedIn and Facebook, advises referencing a founder until you get a negative reference, at which point you know you have exhausted the reference pool.

– How you frame the questions you ask in a reference check matters. For example, when Max Rhodes of Faire was being referenced, many VCs asked, “Was Max a good employee?” The answer was not a simple “hell yes.” And several passes because of this to their regret later. However if they had asked, “Is Max capable of being a world-class entrepreneur?” the answer would have been “hell yes.” It is important to get the question framing right and to be very careful and intentional about what you want the person you are asking for information from.

* Two questions that generate a lot of insight while referencing per Keith: a) What would lead to this person being more successful? b) if something were not to work out, what would be the primary root cause?

3/ On a similar note, Keith shares one of his favorite interview questions for senior candidates: “If you were the CEO of the company, what would you have done differently?” He says this gives him feel for their strategic mindset and whether they can drive value creation? He then shares his killer follow-up: “Why didn’t you do anything about it then? Why weren’t you able to persuade the CEO to do it?”

Staying on the concept of hiring, he says to ask yourself a month after hiring the candidate, “Would I make the same decision again?” He says whatever the answer the 30-day feedback loop is faster and about as accurate as waiting a year or two, in most cases.

Third, Keith describes how, in companies that are doing well, he pushes the CEO to go even faster and get better. He also shares that a friend told him the most common trait of the best CEOs is a relentless application of force. He believes that is the CEO’s job,that is, pushing people when things are going well. This helps prevent the organization from becoming complacent and comfortable. Lenny agrees with this and sees it reflected in how Brian Chesky operated at Airbnb. Keith responds by saying that for companies in his portfolio that are not doing well, he shifts into a coaching and supporting role. He says in most cases the founder knows they are struggling, and being extremely critical or pushy would not help them solve problems at that point.

He says the single best signal of a great company is speed of execution. He has used that to guide his follow-on investments, like in Ramp, where a credit card product that would take nine months to launch elsewhere was launched in just three months.

4/ Keith asks founders he meets during pitches, “What are the accumulating advantages of your startup?” He believes a strong startup gets better over time and builds an unfair advantage. The first thing people think of is network effects, but there can be other accumulating advantages as well (e.g., brand, supplier relationships, etc.). What he really wants to understand is how the founders are thinking about this. At the stage where Keith invests, there may not yet be any advantages because it is still early. He wants to hear how the founder is thinking about it and how they articulate those ideas in their own mind.

5/ An interesting point Keith makes is that in two of the companies he’s involved with, the CMO is the biggest user of AI tokens. Both are large companies with lots of engineers, but the CMO is the one who consumes the most tokens. Keith says they are reveling in the freedom to get things going without relying on a large number of deputies to ship.

A few interesting anecdotes about Keith:

– He doesn’t use a desktop computer and relies on his iPad and iPhone. He says this reduces distractions, and gives more flexibility, and he credits Jack Dorsey with teaching him that.

– In his early days as a litigator (the first four years of his career). He said he often spent a lot of time writing the first paragraph of a brief. For example, if he had three weeks to write a brief, the first paragraph could take about a week. Once he had the first three sentences of the paragraph down, he could write about 30 pages in two days.

– When he makes an investment, he wants at least half of his peer group (this is the group of investors he competes with and knows well) to laugh at him that he is doing something crazy. That convinces him he is actually taking risks. He says most startups look like ugly babies, a phrase he credits Ed Catmull of Pixar with, and the true alpha is with these ugly babies he says.

2/ David Senra on Sourcery w Molly O’Shea – December 2025

Link. Transcript. AI Summary.

Nothing very new for David Senra fans. Good look at his views on the craft of podcasting, though if you have consumed his podcast with Jackson Dahl (Dialectic), then you can give this a skip. The following passage stood out:

“In the age of infinite leverage, being at the extreme of your art is really important. And I change that to being an extreme of your craft, because power laws all the way down. And if you, if, if all the people in the world say, hey, I’m going to learn from history’s greatest entrepreneurs, I want to be the default choice.

And if you are, I think I am the default choice, but if you are the default choice, you get all the rewards. So there’s a great example of this where there’s a skater named Tony Hawk, who’s by far the most famous. He’s by far the most famous skate skateboarder.

And I was listening to him on a podcast one time. And you know, he got paid to perform. He had his own skateboard company. He had all these deals he was endorsed by. And he said like something like 90% of his wealth came from the video game, Tony Hawk pro skater or whatever it’s called. And you know, it’s hundreds of millions of dollars flowed to him as a result of that. And it made me think, I was like, Oh, how much did the second, like most famous or second most well-known skateboarder making his video game. And the answer to that question is who the hell is the second most famous skateboarder? Now I’m sure in the world of skateboarding, you might know, but the general population, the answer is, I don’t know. That’s, it’s very important to be at the extreme of your craft. So I’m looking for any of these like little edges that I can keep doing and compound over a long period of time.”

3/ Matteo Franceschetti, Eight Sleep, on The Peel w Turner Novak – November 2025

Link. AI Summary.

Good episode on the origin story and product buildout journey for a hardware startup. If you are a hardware / wearables founder, you should give this a listen / read. Lots here you will find interesting, and take note of. One of the themes of the episode, and one which stood out to me was the challenges of building in Europe. The other notable point was about Matteo’s passion for racing at the highest level, and how he is able to do it despite his travel and the stress of building a high growth startup (his dietary routine was fascinating: one to two meals per day (under 500 calories before dinner), training every day burning 3,000–4,000 calories, 8% body fat, low resting heart rate, high HRV, daily ice baths, sauna 2–3 times a week, keto diet etc.)

4/ Karthik Reddy, Sameer Brij Verma, on Arkam Leaders Lab w Bala Srinivasa – March 2026

Link. Transcript. AI Summary.

Nothing new personally to me, perhaps given I know the personalities here well (though folks newer to the industry should find it interesting).

This passage featuring the false negative / false positive framework was the most interesting part of the episode for me. It is a good tactical guide, I thought. Karthik: “I call it like the false negative, false positive syndrome, right? So the first 20 minutes are to figure out whether you missed a false negative, right? So that’s your anti-portfolio. So that 20 minutes is very crucial. Very rarely do you need to revisit the intuition. What you revisit is the analysis. So don’t get the two wrong. So I have revisited deals. I had funded Purplle after meeting him three times over one and a half years, met Milkbasket three times over one year or so. The check finally came much later. But the intuition is intact from the first 20 minutes. What you’re testing is, I don’t know whether the market is large enough. I don’t know whether he can go raise another round. I don’t know whether this company will survive with just my money.”

5/ Ankit Nagori, Curefoods, on The Ken’s First Principles Podcast w Rohin Dharmakumar – March 2026

Link. AI Summary.

Interesting podcast; hree broad takeaways:

1/ How in India any platform will succeed to the extent it is able to scale quality supply sustainably. The example he gives is of ONDC, which was a light touch platform and hence did not focus on curating and ensuring supply. While the demand was there, the lack of supply meant that there was al limit to how much the platform could scale. He talks about how for Curefoods, ONDC never became more than 1% even though it was actually ideal for them to grow because of 0% commission etc. This was fascinating.

2/ On the low TAM for healthy food in India. After I read this, I know I am now skeptical about any startup that wants to build a venture fundable business in health food. I’m sure there is a scope to build a profitable business which can grow to a certain extent but it doesn’t look like, at least from what Ankit shared, that this can be a venture scale outcome. He shares his learnings: on how they wanted to make EatFit a ₹1,000cr brand but plateaud at 150 crores (he presumed 500k users would order 10 times a month, instead got 150k users ordering 4x a month). The EatFit Indiranagar store only saw significant footfalls on monday to thursday. He is quite bearish on the prospect of health food in India and he says people don’t really believe in healthy food; instead people want to eat tasty food even if it’s not super healthy.

3/ About his style of interviewing. He actually takes people on a walk while interviewing because the walk and talk with high stakes unsettles them a bit and perhaps creates a slight cognitive load / minor stress, which brings out authenticity. His favorite interview question is: “Talk to me about the time when you were firing on all cylinders and you were doing great work.” Then he asks why, and continues asking why (like the Toyota five whys), until he determines what led to success. Was it purely tailwinds or was there some extra immense effort put in by the person, or was there some unique insight and so on?

All in all a fascinating one. I’ve never met Ankit Nagori or read much on him, or listened to any podcast featuring him, so this was actually quite interesting. Oh and incidentally the video gaming book he refers to and struggles to name is ‘Tomorrow, and Tomorrow, and Tomorrow’ by Gabrielle Zevin.

6/ Dan Sundheim, D1, on Colossus ILTB w Patrick O’Shaugnessy – February 2026

Link. AI Summary.

My notes / excerpts from the summary.

1/ When Dan invested in Anthropic, he was warned that it could end up becoming the “Lyft to OpenAI’s Uber”. Dan’s investment was spurred by reading Dario Amodei’s essays. He compares Dario’s essays to Jeff Bezos’s 1997 shareholder letter, whose sheer clarity of thought was then the only early signal of Amazon’s greatness. Dario struck him the same way: exceptional communicator with extraordinary clarity about what he wanted to achieve.

2/ Dan looks at the LLM biz as a hybrid of Netflix and Spotify.

* Netflix analogy: you spend enormous capital upfront on a fixed asset (content/model), then sell it at very high incremental margins over a growing user base. First-movers build a flywheel: more revenue → more content → more revenue.

* Spotify analogy: the underlying product (music/models) is largely commoditized across providers. What creates differentiation and pricing power is personalization. The more a model knows about you, the stickier and more valuable it becomes, the same way Spotify’s tailored experience commands a premium over Apple Music despite identical music catalogues.

3/ Anthropic’s focus on coding and enterprise has played out better than OpenAI’s ‘do everything’ strategy. Dan: “”I rarely have seen any company succeed trying to go after multiple end markets at the same time.”

4/ Dan recounts telling OpenAI executives “You have to do ads” roughly 18 months before this recording. Silicon Valley culture is “allergic” to ads; executives felt it would “taint” a pure technology product. He points to Netflix, where Reed Hastings would have called the idea “out of your mind” 15 years ago, yet Netflix eventually launched an ad tier. Dan’s point: if you’re going to do it anyway, build the culture earlier.

5/ Hyperscalers (AWS, Azure, GCP) is trending towards becoming structurally inferior. 2 reasons: a) greater demand concentration w LLMs who are becoming a dominant customer cohort; whereas earlier they had fragmented demand b) Hyperscalers structured for CPU workload optimisation, and LLMs better at running GPU clusters, and in the long run will start insourcing compute (with better cash flow). He gives the example of Meta which insourced their compute. Similarly says Dan why would any sufficiently large, cash-generative LLM behave differently? Dan: “Every year AI is going to be a bigger percentage of the workloads at any hyperscaler… the majority of the workloads will probably be AI.”

6/ Dan asked an LLM directly: “Are you designing your own ERP system?” The answer was no; they were buying one. His conclusion: systems of record have at least a few years of protection. Vibe-coding an enterprise ERP is not imminent. Software companies that are genuine systems of record (ERP, CRM) have time, but they cannot sit still.

7/ Jeetu Patel, Cisco, on Lenny podcast – February 2026

Link. AI Summary.

Jeetu Patel is Cisco’s President and CPO. Three points that stuck with me from the podcast.

A/ “The story is why you build the product”

A board member told Jeetu when he took the CPO role at Cisco: “Always be the custodian of the message. Don’t delegate storytelling.”

His instinct was to question the need for him to take on the burden of direct messaging, but when he accepted and adopted this approach, he saw that the hidden benefit was forced simplification. If he couldn’t explain something clearly enough to tell it himself, there was zero chance 20,000 sellers could tell it to the market, or customers could internalize it.

He says that the story is not a marketing exercise done after the product is built — the story is in fact why you build the product.

Another reason for doing direct messaging is explained by the metaphor of packet loss that Jeetu borrows from Networking. Messages from leadership to the front line suffer ‘packet loss’ through each management layer. His goal: more direct communication to avoid signal degradation. He says: “Clarity of thought is what brings clarity of communication.”

The corollary risk he flags: the signal coming back from the front line is equally lossy. Leaders get very good at the ‘math of the business’ but lose the ‘soul of the business.’ [Jensen solved this through the T5T mail that he asks everyone in the co to send to him every week.]

B/ Jeetu’s contrarian take: “Criticize in public, praise in private”. Jeetu explicitly rejects the standard management doctrine of ‘praise in public, criticise in private’.

His version: be direct and critical in public (on the problem, not the person), and be explicitly supportive in private. Real problem-solving requires honest, direct debate in the open. In private he says “Don’t be stingy with words”. Instead tell people explicitly that you have their back, that you believe in them. Trust, built in private, is what makes public critique productive. Without that foundation, conflict is destructive.

C/ Jeetu’s six-part framework for building great companies

Jeetu shares there are six elements to building a great co. He frames it as descending in terms of importance: but all six must be present.

1. Timing: the most important factor, and the one you control least. Many great products have been built at the wrong time. He shares a useful thumbrule for distinguishing megatrends from hype cycles: if most people can understand what a technology does in its ultimate form without a PhD, it’s likely a megatrend. AI passes this test. Web3 didn’t — he never subscribed to it: “I couldn’t make heads or tails out of a use case.”

2. Market: large enough opportunity, and keeps expanding as you prosecute it in chunks.

3. Team: not people who like each other, but genuinely complementary. A great market with a mediocre team pulls the team up; a bad market with a great team drags them down. Market always wins.

4. Product: “the soul of a company.” What you deliver, and what problem you solve. He calls it “unethical to have a mediocre product sold in the market.”

5. Brand: once lost, nearly impossible to resurrect. Sybase is his example.

6. Distribution: “Just because you build it, they will not come.”

These are stack-ranked. Timing trumps market; market trumps team; team trumps product; product trumps brand; brand trumps distribution.

If there is one point a founder should take away from this is that the message’s intensity and clarity degrade by default. Your job as a leader is to fight that entropy, in your message, your communication, your team, and your timing calls.

8/ Sherwin Wu, OpenAI on Lenny’s Podcast – February 2026

Link. AI Summary.

Sherwin Wu is Head of Engineering for OpenAI’s API and Developer Platform. OpenAI has 800M weekly active users, ~10% of global population. In this podcast w Lenny, he gives a glimpse of how elite engineering teams are able to leverage AI and get significant work done.

He says that at OpenAI, 94% of engineers use Codex, the automated coding agent, and that 100% of pull requests / PRs are AI reviewed. He says Engineers using Codex are able to open 70% more PRs than non-Codex users and says productivity gap is widening between those who use Codex and those who don’t.

There is an interesting passage how the engineering role has moved from a team of engineers to one engineer managing 10-20 AI agents who are writing code and building products. Effectively even IC engineers are becoming equivalent to tech leads managing fleets of agents. He describes how the famous book Structure and Interpretation of Computer Programs, (the “wizard book”), which describes programmers as sorcerers who, through chants and invocations, cast spells that conjure new entities. . He says this is effectively what programming today is.

Sherwin describes that often when a coding agent fails, the root cause is typically something to do with the context. Either the context was insufficient; that is, the tribal knowledge that engineers had wasn’t captured or encoded into the context which the model can access. He says it isn’t as much about making prompts as detailed as possible as it is about encoding that knowledge into the context via markdown files, skills files, etc. and such structured documentation.

Interesting exchange on how with rising engineer productivity and the ability to spin out products, the choke points are moving to distribution, organizational process, and friction required to adopt behaviors to support product adoption and so on. Lenny suggests using LLMs themselves to peer around org walls.

Sherwin suggests non-tech organizations could adopt AI not via top-down recommendations but actually through people working on the ground who are not necessarily from tech but are proficient at leveraging nocode tools such as Excel macros or Appsheet etc.. He says these folks are best placed to figure out how to use and customise AI for the last mile in their roles, and thus should be constituted into some kind of ‘tiger team’ who can all work together. This tiger team should comprise people across different functions who can get to work together to create AI tools, etc., and improve the org’s capabilities around AI.

Compelling point by Sherwin on how in today’s AI world it can be dangerous to listen too much to your customers because customers are inherently backward-looking and will give you ideas that if you adopt could trap you into a local maxima. The example he cites is of vector stores and all other similar scaffolding, which was required at a certain time but as the models improved, the requirement for that scaffolding moved away. He describes how if you had actually built a business based on vector stores etc. you would have got trapped into a wrong business. Fundamentally adding human design structure to ML systems loses out to just raw compute improving the model themselves.

Sherwin describes how the best companies he sees today are kind of building products that are 80% of the way there with the present models. These work well but they’re not exceptional and then as the models improve these products are able to kind of leverage those model improvements and unlock new features which can wow customers.

He says that frontier models are improving along two axes: we’re likely to see longer and longer tasks, multi-hour tasks, and the other one he says is multimodal audio, which will leverage voice and talking, which is how people communicate in offices.

Overall this was a fascinating podcast for it gave me a glimpse into how frontier labs, who are the most advanced users of AI, are themselves leveraging AI and organizing themselves. The other useful takeaway was how businesses should use tiger teams to drive AI adoption.

9/ John Arnold on Colossus ILTB w Patrick O’Shaughnessy – March 2026

Link. AI Summary.

John Arnold is arguably the greatest energy trader of all time. He ran Centaurus Energy from 2002, compounded at extraordinary rates, and retired at 47. From his recent appearance on Patrick O’Shaughnessy podcast episode, I derived two broad takeaways.

1/ ‘The best seat in the house’

The central idea: elite performance isn’t just about skill. It’s about building ‘the best seat in the house: the position with the richest information flow, the most robust systems, the deepest perspective on the market. After Enron’s collapse, Arnold had a choice: join the trading desk absorbed by UBS, or start his own fund. He chose the latter. What followed was a flywheel: superior returns attracted more capital than he could absorb, so fees rose (eventually to 3-and-35). Those economics funded the best analysts, proprietary data, bespoke systems, and a culture that itself became a recruiting asset. Each advantage made the next one easier to build.

For a large part of his career, Arnold was the largest market maker in natural gas. That position gave him something more valuable than direct profitability: visibility into the positioning of every significant counterparty. By reverse-engineering why others were trading the way they were, he built a live model of market psychology. That was his real edge. With scale, they were able to effectively expand the surface area of this edge into finer and finer competitive advantages.

2/ The solar myth, and the geothermal as the most interesting energy sub-sector

Arnold offers a useful corrective on energy transition narratives. Yes, solar panel costs keep falling. But the panel is now a shrinking fraction of total delivered cost. Land, labor, transmission access, and cost of capital (up sharply since 2020) are all rising. The result: solar PPAs are roughly 50% more expensive today than at their 2020 lows, despite cheaper panels. A similar dynamic may now be playing out in batteries as lithium prices spike. The lesson: when a technology gets hyped, track which component is falling in cost. Often it’s not the binding constraint.

Advanced geothermal is Arnold’s pick for the most compelling energy investment opportunity right now. It’s true baseload (unlike solar and wind), environmentally clean, early on its cost curve, and can leverage existing oil and gas talent and infrastructure. The analogy he draws is to early shale: slow to prove out initially, then transformative once project finance became comfortable with the asset class.

10/ Ben Thompson, Stratechery on Cheeky Pint w John Collison – February 2026

Link. AI Summary.

My notes & thoughts from reading the summary:

1/ Ben quotes Zuckerberg’s underreported insight from an earnings call: “The largest and most successful agent in the world today is Facebook advertising.” Advertisers don’t manually target demographics anymore. They simply say “a customer is worth $10 to me” and Meta delivers one at exactly that price, keeping the spread as margin. It’s a pure outcome-based agent. Ben and John agree new, very large companies will be created in AI-powered e-commerce, particularly on the discovery/demand side. Ben’s most compelling vision: AI that anticipates the need (anticipatory ads), rather than responding to it. He illustrates with the 3D-printed router rack-mount story: an AI should be able to identify that he’ll need such a part before he does. Ben’s preferred ad model is Meta-style: build a deep user profile and surface relevant ads unconnected to the current query, just as Instagram ads for products you didn’t know you wanted.

2/ Ben distinguishes between “SaaS going to zero” (wrong) and “SaaS no longer being a growth story” (the real valuation problem). Systems of record (Workday, Stripe Billing) are safe. Nobody’s Claude Coding a replacement for those. The seat-based, growth-dependent valuation structure is the issue. John confirms Anthropic just installed Workday.

3/ AI creates a perfectly individualised content experience, which makes shared content paradoxically more valuable. If tens of thousands of people read the same piece, that common reference point has increasing social currency. He thinks “live” and “shared” experiences (sports, concerts, classroom discussions) will appreciate in value as everything else becomes individualised. This leads directly to sports: yes, sports teams become more valuable in an AI-abundant world, because everything live becomes more valuable.

Subscribe now

Articles

1/ We Have Learnt Nothing – Jerry Neumann, March 2026

Link.

Good, provocative, thought-provoking read. The percentage of new startups succeeding hasn’t risen despite the rise of a ‘science’ of entrepreneurship (lean startup, customer development, design thinking etc). Why is this so? Neumann purports that one of a few reasons is the Red Queen effect: ‘when new methods are widely adopted, no one gains a relative advantage, and success rates stay flat’, i.e., if all startups adopt the same theories then they are fundamentally converging on similar approaches, which in a competitive market fritters away any advantage pursuing the theory may have given originally.

2/ Developing Creative Identity – Michael Nielsen, March 2026

Link.

Long piece where Michael Nielsen explores how he developed confusion over his identity as he transitioned from an academic to a researcher writing a book on science. Was he a writer now or was he a scientist exploring a topic through the medium of writing? He explains how he resolved this identity conflict through a series of vignettes looking at different scientists and explorers – Darwin, Einstein, Stewart Brand etc., attacking a problem through the medium of writing. Finally he arrives at a resolution for himself that he is not a writer; rather writing is his secondary identity but his primary identity is that of a researcher and explorer.

This is one of those hard-to-classify pieces, covering a range of topics around writing and scientific discovery. The joy of the book is not so much in clear takeaways as much as the experience of reading it and seeing Michael Nielsen think aloud on a range of these topics: what good writing is, different kinds of writing, leveraging writing to think through a problem, identity conflicts etc. Recommended.

3/ How to Debug a Team That Isn’t Working: The Waterline Model – Molly Graham, Mar ‘26

Link.

Sometimes when things are not working out in a team, we jump at pointing fingers to a specific person or two who we feel are not performing. Instead, Molly Graham says there could be other issues that are more likely. She suggests using Roger Harrison’s Waterline Model to debug the root cause. First she says start at

1/ Structure layer: Look for goal / role clarity (Is everyone clear about what they are working towards, and what each one of them have to do to achieve it?)

…then, look at

2/ Dynamics: Are the enabling processes / cultural practices (and incentives) working smoothly to achieve goals and help each person execute effectively?

…then,

3/ Interpersonal layer: Is there any interpersonal conflict coming in the way? What is driving the interpersonal conflict? Sometimes it may be do with structure (two people tasked with same role, or unclear incentives etc.)

and finally,

4/ Individual layer: is there a person who is underperforming and so on, for various reasons (could be a skill or motivation issue) etc.

Start at the top at the Structural layer, and then work your way down ideally. Often what you think is a person not performing is a role clarity or incentive alignment issue. Snorkel before you scuba.

4/ Renaissance Woman – Carrie Golus, Winter 2018

Link.

Enjoyed reading this profile of my latest nerdcrush Ada Palmer, yes she of the Dwarkesh Podcast fame. The title Renaissance Woman is a nice pun, given Ada’s academic focus on the history of the Renaissance, and also given she is a sci-fi writer (three novels so far), and a musician.

5/ Why are India’s Youth Still Flocking to Civil Service Exams? – Sahaj Sankaran, January 2026

Link.

The article looks at the popularity of the civil services exam in India and explores what underpins it popularity, and what the unintended consequences of a long, arduous and highly competitive entrance exam. First, why it is popular: the obvious answer is that getting into the civil services confers job security and increased prospects, both from the high pay in a country with under $3k per capita income, and the ability to make more money via corruption. There is an additional premium beyond the corruption premium, and that is protection premium: an original concept by the author that entry into a government role makes you and your family members less amenable to arbitrary rules and whims of the powers that be, which is important in a country where the rule of law is weak, and the law is applied arbitrarily across income and caste spectrum.

Second, the unintended consequences are that a large number of students spend years preparing for this and the unsuccessful pay for it in terms of loss of income, poor mental health, etc. Nothing new in and of itself but the article looks at it through the lens of data, citing a well-known paper by Kunal Mangal, who looked at what a hiring freeze in government jobs in Tamil Nadu and the resulting increased competitiveness for the remaining jobs did to the careers of those who spend time preparing for that.

6/ Some Simple Economics of AGI – Christian Catalini et al, February 2026

Link.

Illuminating read. Taught me a lot on how to think about careers and their defensibility as we countdown to AGI.

The paper says that as the cost of automation falls (and will fall to zero or near zero with AGI), and more and more stuff gets automated including traditionally areas where human beings had a native advantage, the cost of verifying is rising. This is because the cost of verifying is bottlenecked by finite human time. Humans cannot verify faster just because agents can execute faster. The gap between these two curves is structurally widening. This gap is what the authors call the ‘Measurability Gap’. And it creates a growing zone of economic activity that is cheap to automate but expensive (or impossible) to verify.

Two dynamics make this worse over time.

– The ‘Missing Junior Loop’: When you automate entry-level work, you eliminate the apprenticeship loop. Fewer junior analysts today means fewer senior verifiers tomorrow. The ‘Missing Junior Loop’, as the paper calls it, compounds: you erode your own future capacity to verify.

– The ‘Codifier’s Curse’: when experts convert tacit knowledge into training data, they accelerate the automation of the very judgment they’re being paid for. Well-intentioned knowledge transfer becomes self-replacement.

How should individuals respond to this trend? What strategies protect them and make their careers defensible? The authors propose looking at this through a two-by-two matrix:

1. On the vertical axis is ease of automation

2. On the horizontal axis is ease of verification.

The bottom left box, where verification is easy and automation is easy, is likely to be automated away and anyone in this space should get out of it.

The bottom left is automation is easy but verification is hard. There, a human being should become what the authors call a ‘liability underwriter’, where their value is in verifying the output AI generates. As the verification bottleneck increases with AI productivity, their value is likely to grow over time though there will be fewer of them overall. Whoever remains will be able to generate huge value in verifying the output, for example a radiologist who verifies AI interpretations, and talks to customers to share the feedback.

The top left is where automation is hard but verification is easy. This is the realm of the ‘directors’ as the authors put it. A founder building something that has never existed before is operating in Knightian uncertainty. There is nothing to automate yet. The search space is essentially infinite: infinite possible strategies, infinite possible pivots, infinite possible interpretations of early signals. An AI agent pointed at this problem would a) struggle with the choice set, or b) perhaps optimize toward the wrong proxy. In the first case, the Director’s job is to constrain the search space — to say, we are not exploring that direction, we are exploring this one, for reasons hard to articulate but borne out of past experience, pattern recognition and intuition. With regards to the second – optimising for the wrong proxy, the director has to step in and correct this before it is too late, e.g., imagine telling an AI to maximize user engagement and it figures out that outrage works better than satisfaction. The metric goes up, but customers are pissed. The original intent is betrayed. This is called intent drift.

Then finally the top right, where both automation and verifiability are hard. A good example is early stage VC investing in deep tech, where fundamentally you are betting on people and there are ultra-long feedback loops before you know what you did is right or wrong. In such a context, value goes to the person who is able to generate social consensus about an investment, and others gravitate to supporting a founder because of the validation from the person who provides social consensus. This is what the authors call as a ‘meaning maker’, someone whose value is in curation, interpretation, narrative creation, and finally legitimising the object as worthy. Think Tyler Cowen tweeting about a writer or podcaster, or Vinod Khosla backing a founder. Their behaviour or backing is the signal that legitimises the object transferring valuable social currency from them to the subject. They are meaning makers, not because they have a formula or algorithm, nor even that they are right all of the time, but because ecosystem has learned, over time, to coordinate around their judgment.

TLDR: The bottom left box, consisting of roles where the task is measurable, the output is verifiable, and the feedback loop is short, gets automated fully. The other three are safe because they are, by definition, outside the reach of measurement. And AI, at its core, is a measurement and optimization machine. Where measurement fails, so does AI.

7/ Sam Altman May Control Our Future – Can He Be Trusted? – Ronan Farrow & Andrew Marantz, April 2026

Link (paywalled).

Enjoyable read on Sam Altman’s two-faced personality, and the conflicts around safety and privacy that led to the Anthopic team’s exit from OpenAI, and the events of October ‘23 where Altman was sacked and then reinstated.

8/ What’s the Matter with India? The judicial system as root of all evils. – Nicholas Decker, May 2025

Link.

Nicholas Decker, a PhD student at George Mason University, argues that judicial dysfunction (including the lack of judges, pendency of judgments, and consequent delays in judgment) is the main constraint on India’s growth. He describes how the ineffectiveness of courts, led by a very low judge population, and delays in judgement, lead to firms intentionally not growing in size so as to avoid future potential litigation such as that could arise from conflicts with managers; he describes how most firms in India are growth-limited by the number of male family members!. He also claims that as much this judicial dysfunction costs India 10% of its GDP, but he does not share the calculation for that figure.

Interesting post, but I am not sure he can rely on a single cause for India’s slower growth. Judicial dysfunction is certainly a factor, but there are other constraints as well. For example, land conversion from agricultural to non-agricultural use is a constraint too as Shruti Rajagopalan has argued. That said some of the hurdles in land conversation may also be due to judicial dysfunction, but seems primarily driven by poor laws, which are mostly the legislature’s fault rather than the judiciary’s.

9/ My Quest to Solve Bitcoin’s Great Mystery – John Carreyrou with Dylan Freedman, April 2026

Link (paywalled).

John Carreyrou, yes, the same journalist who reported on Theranos and led to its unravelling, explores if Bitcoin’s creator Satoshi Nakamoto is British cryptographer and entrepreneur Adam Back. On reading it, I did not get a feeling that there is decisive proof that Adam Back is in fact Satoshi Nakamoto. Carreyrou explores and lays out a lot of circumstantial evidence around why Adam Back could be Nakamoto, but it’s not conclusive. Evan Ratliff, who too has tried to unmask Satoshi’s identity, thinks that Carreryrou’s “approach is not much of an ‘investigation’, more like a gradual winnowing of facts to the ones you like”.

10/ How should Emerging Managers Approach Marketing? – Laurie Owen, April 2026

Link.

This is a really really good piece on how the emerging VC manager should think about content. Laurie Owen runs a firm that helps VC firms with content, and has been thinking deeply at the intersection of venture and content and it shows. Lots of actionable content here.

His main condition is that emerging managers should not rely on larger fund houses like Sequoia, A16, or Benchmark for marketing input or advice.

Instead, they should:

• Identify the types of founders they want to reach.

• Look at the content that will help those founders engage with them.

• Focus on owning one specific plank in that audience’s mind.

• Choose a format that makes it easy to create content that reinforces that plank and builds engagement.

It is marketing 101, but he illustrates these principles with lots of examples of successful emerging managers, including how these approaches shape their content marketing and help them get it right.

Bye!

It is time to wrap this! As I shared earlier, you should think of this substack as akin to a monthly magazine - you don’t have to read it all in one sitting, and you don’t have to read all of it! Feedback, or your own ruminations are welcome. Please use the comments section to engage!

Regular readers know that this newsletter has two permanent sections:

• Writings - where I usually write and / or refer to one or more original pieces that I published in the previous months, typically about venture or the startup ecosystem.

• Readings - about what I read and learnt about. My reading diet is tilted rather heavily in favour of books and podcast transcripts, and against articles / newsletters. This will naturally reflect in the reading list.

This is a long newsletter - think of it as akin to a monthly magazine from me (only the frequency may not be monthly!). I don’t know if you can read this entire newsletter (and peruse the links) in one sitting, and even if you do a second run ( which I very much doubt), you will have to pick and choose what to focus on. A good way to read this newsletter is to certainly read my original writing(s) below, and then glance through the rest and pick 1-2-3 items that pique your interest. Anything more is a bonus!

Writings

It has been a strange kind of two months on the writing front. I have been productive (of a kind) but I haven’t been productive on what I really should be. Let me explain. As some of you know, I am writing a book on the topic of product market fit in a serialized fashion and have released two chapters (of a total of five) already, but the third chapter, which is what I am on now, has been a bit slow going. On the other hand, I have been able to quickly spin out a few (shorter) pieces: hence productive in a sort of way.

One of the shorter pieces, well, now not that short, was a piece that was derived from the work I was doing on chapter three of the PMF book; it describes how founders should think about the early product they take to market to validate the solution they have in mind. I look at startups as falling in a three by three grid; on one side is the type of product, whether it is a Painkiller, Vitamin or something called a Toothpick in between, and on the other side is the market type, whether it is a competitive Red Ocean market, a less competitive Orange Ocean market, or a non competitive Blue Ocean market. Basis where a startup falls on that grid, they can determine how detailed a product they should build.

If you are a Painkiller in a Blue Ocean market, you can get away with a very basic product; but if it is a Vitamin in a Red Ocean, you will need to build a product that matches if not surpasses competition. In between cells need products that fall somewhere in the middle of the product depth continuum. So it is thus a framework around what kind of product to build. This ended up becoming a 6,000+ word piece.

Which of these 9 Product x Market Type Categories is your Startup in?

Continuing on this topic, I was able to get two PMF Convos done over the last couple of months; one with Shashank Mehta, the founder of The Whole Truth, and the second with Chirag Taneja of GoKwik. I thought they were really good. The newer convos are structured along the broad skeletal structure of the book - Pick, PPF (Product to Problem Fit), and MMF (Motion to Market Fit), and benefit from this structure.

PMF Convo #22 - Chirag Taneja, GoKwik

and

PMF Convo #21 – Shashank Mehta, The Whole Truth

The shorter pieces included one on what I saw as the state of podcasting and my reflections on podcast consumption circa early 2026. This one got some play because Tyler Cowen linked to it in his daily reads and it got a fair bit of traction.

Reflections of a Podcast Power User | January 2026

The other two were shorter year end wrap up pieces that I put together; one for The Generalist and the other one for Blume, both below.

Natural Stupidity, VCs Going Global, and Super-Young Founders (for Blume)

Agent-Powered Interactions, Second-Order Effects, and the Future of Work (for Generalist)

I have been telling myself that I need to hunker down and get going on the last section of chapter three, so that is what I will get to after this newsletter:)

Readings

Books

2026 is off to a decent start on the book reading front, especially on my goal of reading more fiction this year.

First up are the fiction reads.

1/ Everything’s Fine – Cecilia Rabess

Romance novel, of a kind. Entertaining, but also a little uncomfortable. A WASP finance guy of conservative leanings and a black progressive finance girl turned ‘journalist’ fall in love, and struggle to stay in love, in the background of Trump’s rise to power. If this was adapted to India, it would be the story of an upper caste Hindu finance boy who is pro Modi / BJP and a muslim journalist girl, in the background of Modi’s rise to power.

2/ Flesh – David Szalay

Powerful staccato prose depicting the life of a Hungarian man, from his teenage affair with an older woman, to his emigration to England, his rise led by his getting married to a rich (older?) woman, and his eventual downfall. This won the Booker Prize for ’25. Hence picked it up from the airport, and ended up reading it cover to cover in a few hours. The book enables speedreading, given the lean prose (Hemingwayesque, in a way) and rapid pacing. Very little interiority or prose describing his mental state or so. A lot of short passages that push the pace ahead. Also from the prose and the structure of the novel, it was hard to develop a liking for the character. I don’t think this is something that will make my Desert Island list:) That said it did leave an impression, of a kind.

Now the non-fiction pieces.

3/ Make Time – Jake Knapp & John Zeratsky

Good book on being able to use the limited time in our days to get more done; by the creators of the Google Design Sprint. They recommend that we focus our days around 1 ‘highlight’, a task that takes 60-90mins to do, and is something that is urgent, or gives you satisfaction, or joy, or all three. To ensure you are able to focus on your highlight, they give you a set of tactics to ‘laser’-focus on getting your highlight, to ‘energize’ yourself so you can stay locked-in on getting to the highlight, and finally ‘reflect’ at the end of the day on whether you got to the highlight successfully, and whether you laser / energize tactics worked, and if you need to add more such tactics. These 4 – highlight, laser, energize, reflect – constitute their time management or ‘make time’ system. So long as you are able to get the highlight done (it could be work or personal), and are able to string a series of highlights (if needed) to progress towards a long-term goal, and / or eventually make it a habit that you do automatically (like exercise), you should be satisfied. This is a practical and easily actionable time management book; and one that doesn’t put out unrealistic practices or a regimen that is tough to adhere to.

4/ Another Way – Dave Whorton with Bo Burlingham

Another Way is part autobiography and part story of a pivot by Dave Wharton, a tech VC who worked with KPCB at Kleiner Perkins and TPG Ventures, and then set up his own fund called Tugboat Ventures. Along the way, he had an epiphany around how the venture model he was practicing was akin to a slash and burn model, forcing companies to get big fast, engorged on capital, and eventually forcing the funded to list or exit when they were not ready to. He saw the merits of a slower-growing business that could stay private for as long as possible, without taking external capital, with its growth financed from its earnings. He calls these Evergreen companies, and the latter half of the book is a celebration of these Evergreen companies.

This pivot is captured in the book, along with his philosophy around Evergreen companies and various frameworks that he brings in such as the seven Ps, the nine innovation rules, etc. What I found really interesting in the book, given my interest in venture history, was his account of his KPCB days including how he was wooed by John Doerr, how he worked very closely with him, the stories of the late nineties dot com madness, including how he played his role in making Google happen for KPCB. That is only one chapter though. Overall, I thought it was an interesting read in parts; though for venture nerds I suppose the first section of the book is what is particularly interesting.

5/ Brick by Brick – Manish Vij

This is founder-turned-investor Manish Vij’s autobiography. Found it particularly interesting to read the chapter describing how his startup Letsbuy got early traction, and grew fast though unsustainedly, and looked it was on the verge of something big, but then got sold to Flipkart. He gives us a glimpse of what really happened, including the shenanigans that VCs played. That was really the highlight of the book to me, at least, given my interest in venture history. Overall, it is an easy, fun read, with Manish capturing his evolution as an operator and founder, his early attempts at entrepreneurship and failures, his success as a media entrepreneur, and then eventually finding his footing as an early-stage investor + venture builder in the Indian startup ecosystem with Smile Group, which is akin to a Sutter Hill for consumer digital businesses for India.

Podcasts

1/ Michael Lewis, on Acquired w Ben Gilbert & David Rosenthal

Link to the episode. Link to excerpts from the episode I found interesting.

Acquired zigs where others zag. Its signature podcasts, where they dive deep into the history and evolution of an iconic company, are long (3+ hrs), infrequent (just 6 episodes in 2025), and feature the two hosts talking to each other excitedly about a company. Their passion, and curiosity for the topic, along with clearly compelling content, has created a popular yet cult-y podcast brand. In this episode, celebrating a decade of Acquired, the hosts are interviewed by Michael Lewis. Interesting episode, and one that podcast aficionados, and podcast hosts will particularly enjoy (The segments scattered across the episode on how they prepare for the episode, and then how an episode comes together was of course fascinating!).

They describe how the podcast evolved, from more frequent shorter episodes covering tech M&As (hence the name Acquired) to the longer, less frequent company deep dives. Their strategy came together organically as they saw what was working, and learnt from the companies they were studying. In general, they learnt the power of durability and compounding across the companies they studied. Specifically, NFL and Hermes taught them the power of scarcity, and Berkshire taught them to focus on their circle of competence and ignore the ‘too hard’ pile (leading them to avoid outreaches from Hollywood). Interesting line on them becoming aware that they were better off ignoring any potential distractions and instead just focusing on the core product. “The opportunity cost is so high of spending a month not making an Acquired episode…The answer almost always is we should just make another episode.”

A couple of points made in the episode that surprised me was how much of an improvisational element there is in the recording – both do their own analysis of the company, and agree on a broad structure with each other, but do not share their findings with each other. The other was around how they select their sponsors (typically B2B Enterprise SaaS or AI companies), and also try to invest into them. Overall worth a listen (or read), especially if you are into Acquired and / or podcasts in general.

Ben: They go hand in hand. Cheap growth is covering the current thing. I’ve been toying with this idea of stored potential energy that great businesses have a stored potential energy that you can’t see in the current financials.

Michael: Great people have that too. They have these reserves that come out when they need them.

Ben: And they’re not presented in the obvious markers.

Michael: Yes. They aren’t sparkling there in front of your eyes anyway.

Ben: I think we’re trying to store up as much potential energy in Acquired as we can rather than anytime there’s a way to make it show up on the financial statements, like letting out the pressure and being like, yup, second show, yup, more ads, yup, dynamic ads from an ad network. You can say yes to all these things and you can sugar high the current profits, or you can try to figure out how to store up as much potential energy as you can. I think once you hit the point in life where money won’t make you any happier, then there’s actually not a point to letting any of that potential energy out. It just creates goodwill for everyone, most principally, selfishly yourself to keep it bottled.

2/ Jimmy Soni on Infinite Loops w Jim O’Shaughnessy

Link to the episode. Link to an AI summary of the podcast that I prompted.

Really interesting episode on book publishing featuring Jimmy Soni in convo w James O’Shaughnessy. Broadly, legacy publishing (by the likes of Penguin, Harper Collins) reflects the analog era – oriented towards distribution in bookstores, led by historical structural incentives and forcing functions (awards, reviews etc). Leads to a few interesting challenges

• Legacy publishers see authors as contractors who are lower on the totem pole to them, but many authors today have social media presence > publishers. Most authors dont realise that the power has flipped.

• Legacy publishers see the book cover as an aesthetic decision (designed w bookstores in mind); but it is not. It is an interface for a purchase decision in the digital sphere. It is the YT equivalent of the thumbnail.

• Legacy publishers are unable to give attention to most authors unless they are celebs….

Asks authors to become ‘problem authors’ pushing for data, A/B testing on books (interesting anecdote by Jimmy Soni of how A/B testing covers led to a cover that the test group loved but the editors hated), and pushing to write the story they cant shake of, not what the publishers want them to write.

3/ Everett Randle, Benchmark, on 20VC w Harry Stebbings

Link to the episode. Link to excerpts from the episode I found interesting.

I first came across Everett Randle through an article he wrote on Tiger Capital called Playing Different Games. He struck me as a differentiated thinker. Not surprising that he was at Founders Fund, though he left that soon for Kleiner Perkins, and recently joined Benchmark.

This was his first podcast appearance on joining Benchmark; clearly an interesting interview. It became a bit controversial because of one particular soundbite of Everett on how large mega-funds like GC and Lightspeed, are chasing investment velocity. I don’t think he was wrong, but it did get some traction on Twitter.

What I actually found more interesting, though, were the broader ideas in the podcast. A couple of points really stood out for me.

One was around AI and how we should think about it differently from SaaS. In SaaS, high margins tend to be desirable, whereas AI is structurally lower margin; that’s a feature, not a bug. Just like cloud businesses, which account for a large share of spend from customers (vs SaaS) and have a lower margin profile than classic SaaS. AI companies will likely look similar to Cloud in that they’ll accrue larger absolute revenue from customers, but with lower margins. That’s just the nature of the model. The takeaway for me was that we should stop forcing SaaS metaphors, frameworks, and metrics onto AI companies.

The other part I really enjoyed was his perspective on Founders Fund. He was only there for about two years, but clearly it left a strong imprint. One point that stood out was how he described Peter Thiel’s use of incentives and mechanisms to test your conviction e.g., encouraging people at the firm to invest as much of their own money into the company as possible, even enabling access to credit lines to do so. I found that fascinating. It’s a real conviction test: if you’re not willing to go all in yourself, why should your LPs take exposure? In that sense, it’s a very pure test of skin in the game.

All in all, a genuinely interesting episode—and well worth a listen. Venture nerds would love it.

Everett: With someone like Peter Thiel, Peter, I think so much of his cleverness and so much of his genius is actually in the way that he builds his firms, than his investments. So the way that he’s designed Founders Fund is that he creates all these incentive structures and mechanisms almost to constantly be testing your conviction. So there’s a program, for example, at Founders Fund where anyone that works on an investment, or if you’re leading an investment, you can personally invest alongside the firm in that investment, almost as if you’re angel investing.

And at first glance, it just looks like this amazing perk that you can have by being an investor at Founders Fund. But deeper down, it’s a conviction test. Because if you’re sponsoring some pro rata of a company that’s like doing okay, but not great, but the founder really wants you to do the pro rata to not blow up the round, but you’re not doing some of your portion of the individual side of that investment and your angel investment, Peter can go to you and say, do you not think this is better than having your money in the S&P? Why would we give our LPs this allocation in this round if you don’t even want to put your own money in this round? So there’s like 100 different things like that that exist in Founders Fund that aren’t explicit.

Harry Stebbings: I would hate for people to be scared and then say no to something because they didn’t have the cash that could be great. What do you think?

Everett: It’s super valid. I think, again, if you’re at Founders Fund, you’re full in and you’re all in. And so I think most of us that were young at Founders Fund at the time all had like debtlines, like unsecured debtlines that we were using to do these side kind of personal investments. And by the way, it’s turned out to be an unbelievable portfolio for myself personally, and it’s all worked out. And so I’m very glad that I had it. But I think that’s part of, you know, he throughout his entire career has really, again, designed his organization. So people are all in. He had like a bonus system for PayPal employees. If they lived within like a couple miles of the office, you’d give them more money. Like he just designs the orgs this way.

4/ Patrick O’Shaughnessy on The David Senra podcast

Link to the episode. Link to excerpts from the episode I found interesting.

This is a long podcast episode (at just over 2 hrs) featuring two elite podcast hosts David Senra and Patrick O’Shaughnessy in conversation. This episode is on David’s show, and David interviews Patrick who has been a key mentor to him. Patrick promoted David when he was yet to truly break out, and gave David the opportunity to bring his podcast, Founders, to the Colossus Network, where it has been ever since.

For those who already listen to them and are fans, this episode will be fun. For those who are not that familiar with them, it will still be interesting, but not as much fun. That’s because the takeaways, as such, are limited and are broadly around Patrick’s attitudes to talent and how he backs and supports people.

The most interesting part for me was the passage where Patrick talks about how goals are not as important to him as life principles. Patrick wrote an essay a while back called Growth Without Goals, where he argues that once you have goals, they become self-limiting, and once you achieve them, you are left with a new challenge of what next. Instead, he finds that having a principle, something you can structure your life around and live by, is far better.

Patrick references a talk by Bret Victor called Inventing on Principle. In that talk, Bret Victor says his core principle is to reduce feedback time to creation, and everything in his (Bret Victor’s) life has revolved around that. Patrick says that, very similarly, his own key principle is to identify interesting talent well before they become widely known, and then promote them and help make them famous. He does this not necessarily out of deep commercial interest; sometimes there is no immediate commercial interest at all. He does it because he genuinely loves doing it. That, to me, was really the core takeaway, or the essence, of the podcast. There is a bunch of other stuff as well, which I have excerpted below as well that I found interesting, but the above was the heart of it for me.

5/ Saam Motamedi, Greylock on Uncapped podcast w Jack Altman

Link to the episode. Link to excerpts from the episode I found interesting.

This podcast episode is like inside baseball for venture nerds. Saam Motamedi, a partner at Greylock, one of the oldest venture firms and possibly the first institutional fund, gives us a peep into the firm. There’s a great anecdote about how met with some of their emeritus partners, folks now in their 80s and 90s who were part of Greylock back in the 60s and 70s, and how they used to source deals then. One tactic: buying local newspapers across cities and scanning the classifieds for job postings, on the theory that aggressive hiring was a signal of a company growing fast. Greylock, in that sense, really is a storied old firm—one of the first institutional VC firms, not a family office.

In the episode, Sam also gets into how they actually work today. One concept I found particularly interesting was how they think about attribution for the success of a deal. They use a concept called causal impact, it could be someone who sourced, and / or someone who helped drive conviction internally, or who played a role in recruiting a key senior engineer and materially accelerated the company in some way.

He also talks about how performance is evaluated internally: ~18 criteria across five buckets, which gives you a sense of how structured (and multidimensional) their feedback systems are. On investing philosophy, he notes they’re open to taking execution risk but are very wary of market risk, and that a lot of their investing now happens at the incubation or inception stage. They do relatively little in the way of “pure” Series A investing backing fast-growing startups.

The last bit I really liked was his idea of planning for serendipity – a bit of an oxymoron, but a useful one. He intentionally makes sure he attends at least one event a week, because as you get more senior, your time gets pulled in many directions he says and you lose those chance run-ins that were critical to sourcing and network-building earlier in your career.

Overall, an interesting episode though probably most useful if you’re already deep in venture.

Saam: Actually, one thing that I’ve learned from Asheem (Chandna)… I actually think a number of people who’ve had longevity in venture do this, is making sure you have a lot of unscheduled time on your calendar. I try to keep one day a week completely unscheduled, and then I try to keep my mornings unscheduled until, like, eleven. Because once you have a portfolio and a team, at some point in the day, your day becomes entirely reactive. And so you have to be incredibly intentional about scheduling time to do long-term thinking, long-term work, and also to give yourself the energy to sprint. Because I think this job, a lot of being good at this job, in my opinion, is very quickly being able to detect when you need to go a hundred ten miles an hour. Yeah. And then getting to a hundred and ten miles an hour really fast. And if you do that every single day, you’re not truly at a hundred ten miles an hour.

It’s also really keeping the open day or the open mornings is so hard because there’s always, like, the, hey. I’m in town for these three days. Are you free? It’s like, well, yeah, I am. Yeah. But that was supposed to be a quiet time. A hundred percent. Yeah. And that, like, if you ask me, what have I gotten better at over the last nine years? Because in many ways, there are many more pulls on my time today than there were nine years ago. I think one of the things I’m unhappy with is I do think there’s a little bit less of it, and I worry about that. Because when I think about some of the early relationships I built, they really were so random in how they were built.

Right? Like, a good example is this week is AWS re:Invent. It’s my first year missing it because I have three boards this week. But there’s so many random events I went to at re:Invent where I met someone that four years later ended up being someone who we hired into the portfolio. I think I have less serendipity surface area today than I had in the past, but I try to very intentionally do things every week, every month to maintain some serendipity.

One is I try to go to at least an event every week. And then I also try to make sure I meet some founders every month who are completely out of network. And I don’t get caught in the like, oh, well, I have a good network now, and I’m just gonna meet people through very strong referrals, because then you become really insular. I think insularity is the death of this business. You have to maintain a beginner’s mind and keep the serendipity, as painful as it is to go to an event in San Francisco. I always meet founders, especially new founders, in person and disproportionately they’re in San Francisco. But I will say that there’s a little bit of, like, having a clear mind that is very useful because you could spend your entire day meeting founders. Of course. And you could feel good and go home and be like, I met twelve new companies today.

But the real question is, like, were you awake in the meetings? I mean, for me, when I finish a week where I just had, like, a zillion meetings all week, I don’t think that I come out of that week feeling like I crushed it. Like, I feel scrambled. And, you know, I think about, like, the last eighteen months, I’ve made four new investments that I’m really excited about. How many net new opportunities do you think I met in that eighteen-month period? I don’t know. I would suspect it’s on average three a week. I mean, if I compare that to myself three years ago, I was probably meeting twenty opportunities a week. Now, are there some opportunities I didn’t meet that I should have?

Almost for sure. Right? But, again, the question is, like, how do each of us equip ourselves to make a couple of really high quality investments every year? I like being in the city and then also being in our Menlo Park office and having more clarity around like, okay. It’s just quieter and you can think more. Yeah. And it’s like, who are the people who are gonna start companies in twenty-twenty-six? Yeah. That I should go make sure I build relationships with today? There have been a bunch of these, like, Charlie Munger clips going around recently. Obviously, it’s not the same thing as venture, but I do think a lot of what he says, like, you can probably apply some percentage of it where it’s like, you shouldn’t be chasing everything, there’s very few things that matter. Like, you should be thinking and studying a lot, not, like, talking all the time.

6/ Trader Joe’s on Acquired podcast w Ben Gilbert & David Rosenthal

Link to the episode. Link to excerpts from the episode I found interesting.

I’m a big strategy buff and find that topic endlessly interesting. My working definition of strategy, adapted from Roger Martin’s, is that strategy is a set of interconnected choices and intentional trade-offs that reinforce each other to give you a competitive advantage in the marketplace.

There’s no better exemplars of good strategy than Costco and Trader Joe’s. Both operate in retail, a low-margin business littered with corpses of companies that couldn’t get it right. Both are beloved brands. And both now have an Acquired episode on them. Acquired’s episode on Costco was one of my favorites. Now they’ve outdone themselves with this episode on Trader Joe’s, which might just be my favorite podcast episode of 2025. There’s so much to learn here, and honestly, so much to enjoy.

The hosts, David and Gilbert, take us through the history of Trader Joe’s from its origins as Pronto Supermarkets to its reinvention as Trader Joe’s, and then the sale to Theo Albrecht (owner of Aldi Nord), the founder Joe Coulombe’s exit, and eventually the transition to professional management. Through the journey we get a deep look at Trader Joe’s and the strategic choices they adopted, and executed on.

The founder, Joe Coulombe, is a fascinating character. In many ways, he comes across a sociologist or anthropologist who deeply understood U.S. consumer society, how it was changing, and structured Trader Joe’s to benefit from these waves of change. They describe how he came across two articles that influenced him. One in Scientific American about how the GI Bill led to many more Americans going to college, and another in the Wall Street Journal about the launch of Boeing’s 767 that would dramatically reduce the cost of travel to Europe. He saw a future with more college-educated, well-traveled Americans who wanted something different from the mainstream. Trader Joe’s was built for this “overeducated and underpaid American,” as he calls them, which is why early Trader Joe’s stores were often near college campuses.

There’s a lot to learn from how strategically Joe Coulombe thought about things. For example, the early focus on liquor at Pronto gave them an advantage that other grocery stores couldn’t easily replicate. There’s also their very disciplined approach to product selection. They have four rules around this. Products should be high value per cubic inch, have a high rate of consumption, be easy to handle logistically, and be something where Trader Joe’s can be outstanding on price or assortment, but ideally, both i.e., hard to find elsewhere, and is at an extremely attractive price.

They describe three phases of Trader Joe’s. The first is “Good Time Charlie,” from its origins to the early 1970s, with a strong focus on wine. From 1971 to 1977 is “Whole Earth Harry,” which emphasized health food. The final phase is “Mack the Knife” which is about reinventing Trader Joe’s for the tougher era of deregulation, with a strong focus on managing costs, essentially the Trader Joe’s we recognize today.

What I found particularly interesting, especially from a strategy lens, is the set of interconnected choices and intentional trade-offs that reinforce each other. For Trader Joe’s, this starts with a very low SKU count. This is around 4k today (In comparison, Walmart neighbourhood market stores are ~25k SKUs, and supercentres are 100k+) and, but in Joe Coulombe’s time, it was as low as ~1.5k. This allows huge depth in the limited SKUs they carry and the ability to negotiate hard with vendors. Importantly, they don’t abuse this dominance. They use it to get a great price and pass it on to customers. Margins aren’t as low as Costco’s, but they pay vendors on time, in fact on delivery, per the hosts, which delights vendors and makes them want to work with Trader Joe’s. In return, vendors often give them some of their best and most interesting products.

Another choice is their comfort with discontinuities. They’re fine carrying products that may not repeat consistently, odd-sized eggs, one-time imports, and so on. Unlike large retailers like Walmart that are built around continuity and massive SKU counts, Trader Joe’s is perfectly happy with customers discovering that something they bought earlier is no longer available.

Then there’s their approach to staff. They pay really well, typically 60% over market rates. This leads to enthusiastic staff and much lower turnover, which in turn reduces the need for constant training and creates a very different in-store experience. Their private label strategy is also extremely clever. They source innovative products, often with the help of strong vendor relationships, and combine this with distinctive branding and marketing. These different choices and tradeoffs reinforce each, and come together to create a tight biz model, one that has led to a beloved brand (something like In-n-Out Burger).

Overall, this is a fascinating episode with lots of great trivia. I really enjoyed this. I am a retail buff, and a strategy buff, and both these strands came together to make this a fascinating episode for me!

Ben: Amazing story of someone coming to visit Trader Joe’s saying, “Hey, I have a whole bunch of extra large eggs that I just can’t sell to the supermarket chains. Can you help me out?”

David: They only want large eggs.

Ben: Yeah. And Joe says, “Sure, what’s going on with them?” And he says, “Well, they only want large eggs. I’ll sell you these extra large eggs that are at least 12% bigger but for a lower price because I can’t seem to unload them.” And he’s like, “Why the deal?” And the supplier says, “Well, the large supermarket chains only want continuous items. And I’m actually not sure I can regularly produce enough of these extra large eggs.” The kind of disturbing part about this is it’s because it’s at the end of the chicken’s life that they produce these extra large eggs. So it’s kind of the last eggs they’ll lay. And unless I can promise a certain volume and certainty that I’ll be able to supply, there’s not a market for it.

David: The big supermarket industry just isn’t interested.

Ben: Trader Joe’s is like, “We’ve got the perfect consumer for you. They’re value conscious. Our message to them is sometimes we’ll have stuff, sometimes we won’t.” And so if you just want to sell those to me, I’m sure I can unload them on our customers; they’re going to love the deal. And then it’s actually not a big deal for me when I run out, because that’s not a part of our value proposition the way it is for the big supermarkets. So this begins what Joe calls intensive buying. If we have line of sight on something that we can uniquely sell, that we’re going to get a great deal on, that we know our customers are going to love, we should do all we can to go and suck up all the supply of that thing so we can get the lowest per unit price for our customers.

*

Ben: That’s amazing. And so he really comes up with this thing he calls the Four Tests, which is: one, we want to stock goods that are high value per cubic inch.

David: Yes, and it starts, of course, with liquor, as we talked about.

Ben: Yes, and then, of course, vitamins. And you walk into a Trader Joe’s today, you can almost feel that it’s stocked with things that are high value density, even though the goods aren’t expensive. The way it’s all jammed into the store, it feels dense.

David: Yes. And Trader Joe’s today average about, call it, 15,000-ish, maybe a little less, square feet per store. The average supermarket is like 50,000 square feet, and the average Walmart is like 150,000 square feet.

Ben: And back then, Trader Joe’s was like 4,000 square feet. I mean, these were tiny stores, so they needed high value density in them.

David: Or, I’m going to come back to that in a minute. He wanted them to be 4,000 square feet.

Ben: Two: high rate of consumption. You want customers coming back over and over again.

David: Vitamins.

Ben: Three: goods that are easily handled. So much of Trader Joe’s business stems out of this that they are unwilling to start doing things that are hard to handle, that are logistically difficult. And they kind of have this ethos of, if we can make it so people are willing to overlook the fact that we don’t have some stuff that’s hard to handle, then great. All the better business for us if we can keep customers coming back and we only have to deal with easily handleable goods. And then the fourth is probably the most important: something that Trader Joe’s can be outstanding in terms of price or assortment.

7/ Wes Kao on the Lenny Podcast w Lenny Rachitsky

Link to the episode. Link to excerpts from the episode I found interesting.

Wes Kao calls out some genuinely useful communication principles in this podcast with Lenny. I personally found the discussion on signposting interesting, especially her explicit endorsement of it. I remember having read earlier (and I’m struggling to recall where) that signposting was something to be avoided. So this was actually reassuring.

Beyond that, the “sales, then logistics” idea stood out: fundamentally, set context first before you slip into persuasion mode. And the one she calls the single most important principle in communication. Another useful principle was what she calls MOO or Most Obvious Objection. Anticipate the biggest or most obvious criticism to your proposal and prep for how to handle it. She comes back to this principle towards the end, that a lot of good communication advice boils down to spending a bit more time upfront to create clarity, which then saves time later. Overall, a useful episode with some solid frameworks, relevant for both the written or spoken word contexts.

Lenny Rachitsky: Sales, then logistics. What is that about?

Wes Kao: Yes. So a common mistake that I see is overestimating the amount of buy-in that you have from your audience. So that looks like jumping straight into talking about the logistics, the details of the how to do something, of the process. When in reality your audience has not yet decided if they even want to do the thing. So what I see operators do in response then is go even deeper into the logistics and the how, thinking that, “Oh, if I just explain this more than that person will want to do it.” When really a sales note is different than a logistics note. A sales note is meant to get people excited to do the thing you want them to do, and to agree to do it. And only then after they have bought in, does it make sense to share the logistics. So there’s an order of operations here.

Wes Kao: You can frame a conversation and sell a bit at the beginning very concisely. So I’m not talking about spending 15 minutes out of a 30 minute meeting selling, I’m talking about one to two minutes, even a couple sentences, and then transitioning into the main thing you want to talk about. So I’m a huge proponent of doing that and basically reminding people, why are we doing this? Why are we here today? Why does this matter? And then getting into the meat.

Wes Kao: Explaining why we’re doing this, why this benefits the business, what problem this is solving. Again, you can do a lot of this in a couple of sentences. And then I also like asking or stating what I need from the other person upfront. So saying, “Hey, we’re here today because two weeks ago we were reviewing the product flow and realized that there were a couple of parts that were kind of confusing. So I took a stab at fixing those areas, rewriting the microcopy, and I want to present them to you today, see if you agree with these changes, and then we’re going to roll them out. What I’m looking for from you is feedback on the changes and if you agree.” So like that was like 15 seconds, right? Super fast. And then now we’re all on the same page about why we’re here. And you can listen more intently knowing that I’m looking for a certain kind of feedback.

8/ Avnish Anand, Arindam Paul, Nikhil Vora, Rishabh Mariwala on Singularity One podcast

Link to the episode. Link to excerpts from the episode I found interesting.

Thought this was an interesting episode. A consumer operator turned investor (Avnish Anand), an operator (Arindam Paul) and two investors (Rishabh Mariwala, and Nikhil Vora) come together to discuss themes around consumer brands and the changing Indian consumer. Long episode, so I did an AI summary which I thought came out quite well; excerpts I found interesting from the same linked here.

Lots of interesting takeaways but what stood out to me was the a) low brand loyalty but high brand awareness contradiction that India is in right now, and b) how distribution concentration led by limited number of online platforms that are growing in share and power, both benefits brands in improving efficiency, but eventually also constraining EBITDA as the online retailers gain power.

Low brand loyalty, high brand awareness

Nikhil Vora: “On a macro landscape, brand loyalty is at an all-time low, brand awareness is at an all-time high, which is a great case for disruption to happen in almost every category….Let’s say if we for a year out here, and let’s assume that we’ve all been Kingfisher drinkers, I can almost guarantee that my daughter, if she drinks, when she drinks, I hope she doesn’t, she’ll not be a Kingfisher drinker, she’ll have moved to something else.”

*

What distribution concentration gives in efficiency, it will take away in EBITDA

(not sure who said it): “I don’t need to be 40% of Marico’s distribution to challenge Marico anymore. I need to be present in 15 distribution channels. So if I’ve cracked Zepto, Blinkit, Insta, Amazon, Flipkart, Reliance, Demart and so on, I’ve got 25% of my TG market in here.”

Arindam: “So whether it takes 5 years, 10 years, 15 years, 20 years, the moment 40, 45% of distribution is controlled by 10, 12 players, the profit pool that the retailers will have will increase compared to the profit pool that brands would have. … This has already happened in US. This has happened in China.”

9/ Rachel Lockett, Executive Coach, on the Lenny Rachitsky Podcast

Link to podcast. Link to excerpts from the podcast I found interesting.

Educative podcast, where Rachel Lockett, an executive coach shares powerful coaching and communication frameworks, including what she calls the two foundational coaching skills of active listening (across three levels, in the most advanced you go beyond words to understand body language and context), asking powerful questions (delivered via the GROW model: clarify the goal, examine current reality, explore options, and define the way forward). Her core argument is that leaders often advise where they should coach instead, and they miss out on the ability for the coachees to develop themselves. She rounds with a very powerful communication framework called Non-Violent Communication which is a framework used for conflict situations and resolving them. Here she suggests you should state observations, express feelings, articulate needs, and make a request. I thought this was an illuminating episode.

Rachel Lockett: I’ve also witnessed people who are still inspired and continually energetic and seem to have some secret well of some diesel battery, or I guess I should say a Tesla battery that helps them through really hard challenges, and they’re still having a good time. And so what I make of that is that when people are in their gifts and their strengths firmly, most of the time, they have more energy. We all have more energy when we’re operating from the things we naturally are good at and the things we innately love doing. So I try to help my leaders see that they can design their lives so they’re spending 80% of their time in their gifts. That seems really ambitious because you’re stuck within a context that requires a lot of you. Especially when you’re executive at a huge company.

…

Rachel Lockett: So one tool I like to give is for people to actually take two weeks and every night reflect on, what are the five things today that gave me the most energy? And what are the five things that depleted my energy the most? If you do that for two weeks and you look at patterns, you can tell, what are the natural gifts that I’m living in? And what are the things that I’m stuck doing that are exhausting?

10/ Pat Grady & Alfred Lin, Sequoia on Uncapped Pod w Jack Altman

Link to podcast. Link to excerpts from the podcast I found interesting.

Enjoyed this podcast episode, which was the first one Pat Grady and Alfred Lin did on becoming Stewards at Sequoia. Extremely interesting podcast for anyone in venture investing. I found the stats they shared on coverage and loss ratios interesting – it is not often that you get to see such data. The most interesting part to me was the discussion around how polarising voting records are likely better signals for investing than all negative or positive votes (likely because these polarising voting decisions led to more dramatic outcomes), the importance of the mid-funnel decisions (that is, what leads to a certain company being taken to the Investment Committee meeting, or not), and finally the 40 psychological traps they have identified as impeding good decision making.

We do a lot of introspection, post-mortems, post-parades on decisions that we got right or wrong. Just kind of looking at the outlier decisions one way or the other and saying, like, we’ve got this one really wrong. Why we got this one really right? Why what’s interesting about the ones that we get really wrong. Every single one of them, if you play the five wise game, like why, why, why, why, why every single one of them comes down to some psychological bias or emotional trap. Totally. None of them come down to an error in calculations.

Yeah. All of them come down to these background effects that were clouding your judgment. Yeah. And you know, we cataloged them, you know, we have a list of 40 of these things so that we can kind of like use the common vernacular and be able to be able to kind of get in front of them so that we can have a conversation before we make that mistake. Like, Hey, do you have separation of church and state here? What separation of church and state? Well, letting the thrill of the chase bleed over into your clinical decision-making. Yeah. Right. The thrill of the chase is a very passionate, emotional thing where you’re falling in love with the founder, but then you have to come back and put your emotions aside and clinically assess all the merits and risks and make a good decision. And so it’s pretty natural to co-mingle those two things, but that can lead you down the wrong path.

*

We realized a long time ago that the most important decision is actually not the final decision that happens on a Monday. The most important decision is the mid-funnel decision that determines what gets to a Monday. By the time it gets to a Monday, we’re pretty good at making the decision. Our biggest misses are the things that don’t even make it to a Monday. Because you looked, but you didn’t spend real time on something that deserved it. And so having better hygiene around those mid-funnel decisions, we used to just go back to back, meeting to meeting to meeting to meeting to meeting. Now, you can’t have a meeting if you don’t save time afterwards for a debrief so that we can have a concrete conversation about what did everybody think about this meeting? What are the pros and cons? What’s the thesis? Where do we go from here?

Other podcasts I enjoyed

Ikea – Acquired podcast

Link to episode. Self-recommending as Tyler Cowen puts it..

Founders podcast: Andre Agassi’s autobiography ‘Open’

Link to episode. As I tweeted about the episode: “Really powerful. One of the hardest episodes of Founders. Goes hard hard hard. About overcoming the ghosts in your mind. Interesting analogy between founders (esp solo founders) and tennis players around loneliness. Haven’t read the book, and makes me badly want to read it.”

Articles

1/ The Book on Publishing – Keith Gesson, Vanity Fair

Link to the piece.

A tweet by Christina Cacioppo, the founder of Vanta, led me to a page on her website where she lists her favourite books on Venture Capital (she worked at USV once). One of the books there was How a Book is Born. Strictly speaking, the book is about publishing. Christina argues that book publishing is analogous to the venture industry. Just as VCs hunt for the next hot startup, book publishers are hunting for the next big bestseller. Intrigued, I dug further to find that the book was a more elaborate version of a Vanity Fair article by the same author.

I downloaded the article, and it turns out to be about the pursuit by publishers of a book called The Art of Fielding, which became a big hit when it was released. The article is an enjoyable short read giving a glimpse of the process that goes into publishing a book, especially how a hot buzzy book is competed for by publishers. Here, I found the role of (book) agents in publishing particularly interesting. There is no perfect equivalent for them in our world; I suppose there are bankers in our industry, but they are actually looked down upon. Perhaps the right equivalent could be angel investors. So, angel investors in venture / startupland perhaps equal agents in publishing. I found it fascinating as to how agents actually have a particular editor in mind; they know that within a particular publishing house, there is this editor who will like this novel which is about baseball, similar to how an angel thinks this VC at this fund house will like this startup + founder. Overall a great read offering a fascinating glimpse into the publishing industry and its dynamics set around the bidding for a hot book, a la how a deal in startupland can be fought over.

2/ Robert Gottlieb, The Art of Editing No. 1 – interviewed by Larissa MacFarquhar, The Paris Review

Link to the piece. Link to excerpts from the piece I found interesting.

Another tweet, this I think by Eugene Wei (though I can’t locate it), led me to this piece. Robert Gottlieb and the authors he edits are interviewed for the Paris Review. Gottlieb, of course, is the well known editor of Robert Caro and many others; most famously captured in the documentary Turn Every Page, which portrays his relationship with Caro. This article covers how Gottlieb looks at editing, as well as how the authors he edits discuss his role. There are some similarities here between how the editor is akin to the VC and the writer to the founder (sorry if you think I am finding similarities where none are, amongst the book publishing industry and venture).

Lots of interesting stuff in this piece, such as how the title and the structure of the book can increase readability or suspense (see below), how he and Robert Caro fought over colons and semicolons, how much authors look up to the editor for approval, and so on. Most interesting to me was that the editor (or at least Gottlieb) really reads the book only after the writer completes it fully; this feels like a design flaw. If startups were to relook at the industry, they would perhaps move to more periodic reviews, maybe reviews every few months or after a quarter of the book is done. Maybe this is being done in some cases, I do not know. But this is one improvement I thought they could make: read it after maybe three chapters, or once 25% of the book is done, instead of waiting till the author finishes the whole book and then reading it.

Gottlieb: “…A lot of things one doesn’t usually think about can affect the reading experience. The way you structure the book, for example—whether you divide it into chapters or let it run uninterrupted, whether you give the chapters titles . . . Years ago I edited a wonderful novel that later became a successful movie, Lilith, by J. R. Salamanca. It was a powerful and affecting book, and the character who dominated it, who sparked it, was the character named Lilith, but she didn’t turn up at all in the first sixty or eighty pages. I don’t remember what the original title was, but I suggested to Jack that he change it to Lilith, because that way through all the opening pages of the book when Lilith hadn’t yet appeared, the reader would be expecting her. So just by changing the title one created a tension that wouldn’t have been there otherwise.”

3/ Learnings from Consumer AI × Fashion: Why Alle Didn’t Work – Prateek Agarwal

Link to the piece.

Really enjoyed this piece by Prateek Agarwal, the founder of fashion startup Alle reflecting over why his startup didn’t work. I wish more founders would write postmortems like this. There are lots of learnings here, especially for young founders and for those exploring similar business models.

That said, I have one small quibble with an otherwise very well-written piece, and it’s about Prateek’s definition of PMF. He believes he achieved PMF, and my view is that I don’t think Alle quite had PMF. Of course, PMF doesn’t have one single definition, and different folks define it differently. I’ve written about PMF extensively as many of you know, and here is Chapter I of my to be published book on PMF where I define that PMF is really about two fits: product–problem fit, and motion-to-market fit.

At the end of these two fits, the startup should have a scalable GTM motion enabling predictable, repeatable, unit-positive acquisition of customers with high retention (phew!) – essentially a repeatable playbook for acquiring paying customers, and on a profitable basis. It is a purist harder definition, but I like it for the fact that it brings both the product and the market aspects together.

I think Alle clearly had the first fit per my definition, but not the second. There was no repeatable, sustainable, profitable playbook for customer acquisition. In fact, the strong, almost flatline retention that Prateek talks about is actually a classic sign of product–problem fit, as I mention in my essay above.

Still, I don’t want to protest too much, because PMF has no one definition, and it is used often as a shorthand for product love. It does feel like Alle had product love and definitely a 10x / Delta4 product, but the fact that this was an infrequent-use product, didn’t lend itself to a compelling business model. One way to look at it is that this was a Vitamin product in a Blue Ocean market. And when you’re a vitamin product in a blue ocean, you need what I call an early lovable product. Something that is immensely loved. Of course that love needs to translate itself into a compelling biz model to monetize those users. And there, I think, lie the fundamental challenges, especially given the infrequent use case and the business model issues shared here..

4/ Joy Covey: The Deep Keel – Kevin Gee

Link to the piece.

Outstanding piece by investor and investment historian Kevin Gee; an evocative and touching portrait of Joy Covey, Amazon’s first CFO. Also a good look at the early days of Amazon.

5/ 10 years and counting…. – Deepak Jayaraman

Link to the piece.

Enjoyed this piece by my friend Deepak Jayaraman reflecting on 10 learnings over the past 10 years of going solo. DJ as he is called, was a management consultant turned headhunter, who quit to start his individual practice as an executive coach and advisor. Since then he has birthed a popular and long-running podcast in this space, as well as written a book; both titled Play to Potential covering the arena of leadership, coaching, careers.

From his piece, learnings #2 #4 and #6 stood out.

#2: What they discovered was that the depreciation curve of irrelevance was steeper than they anticipated. He expounded that when you belong to a platform like a McKinsey or EgonZehnder, the platform does the hard work of staying relevant and replenishing itself. Somebody in EgonZehnder London is probably working on the latest interview methodology that somebody in EgonZehnder Mumbai could use. Somebody in McKinsey New York is perhaps working on a Strategy framework that the consultants in India could use.

He went on to say that if I just focused on the “Operations” of my business without adequate attention to replenishing myself, I could be going down the curve [of] irrelevance faster than I could imagine. This impetus got me to start the “Play to Potential” podcast which, over time, has developed into the legs on which my platform stands (as things stand today).

#4: We have all heard the term – Leadership is lonely. There are no peers and everyone interacting with you has their own agenda to pursue. However, I have found that XYZ, the person is lonelier than XYZ, the CEO. The CEO, when he or she is looking for advice, can lean on a range of Advisors (Board Members, Strategy Consultants, Marketing Agencies, Lawyers et al) to have sparring partners for various facets of their business.

However, I find that these leaders are juggling various identities and have questions across these that they are often navigating themselves. Questions such as:

• I have had a successful run in the current role over the last few years? How should I think about my journey for the next 5 years?

• Should I be on this treadmill or slow down and spend more time with my children?

• I just made Partner and had a baby soon after. How should I prioritize across the various elements?

• I am the MD of a PE listed business. I have just signed up for a full Marathon. It keeps me healthy but am I overdoing it?

They often do not have some one who understands the full context of their lives across their various dimensions! That is the space where I have had an opportunity to engage with a few of them and it has been fulfilling to be of value as a trusted sounding board helping them play to potential across the various facets of their life!

#6: I have also come to realize that being content does not mean that one is not ambitious. It might just mean that one is patient about what is yet to come. I have discovered that people often applaud visible short term ambition that is restless but do not often notice and appreciate the version of ambition that is patient about the outcomes.

Over the last few years, I feel bringing in contentment has helped me sleep better at night and show up in a more meaningful way to the various people around me.

(Pair #6 above with potential energy mentioned in the 10 years of Acquired podcast!)

Other articles I enjoyed

Loving the annual letters trend that Dan Wang popularized. 2025 saw annual letters from Dan Wang (back after a year’s break during which he wrote Breakneck), Jason Crawford, Zhendong Wang, Samuel Albanie etc. Who did I miss?

I enjoyed this piece by Dharmesh Ba on the changing Indian consumer.

Ever since X / Twitter rejigged the algo to popularise X articles, been seeing a few go viral. This one ‘The Prison of Financial Mediocrity’ on the rise of punting / gambling (prediction markets, crypto, sports betting, stocks) was astute. Pair it with this piece by Alex Danco of A16Z and this by John Luttig of Founders Fund

Of course how can I leave out ‘Something Big is Happening’ and ‘The 2028 Global Intelligence Crisis’!

Bye!

It is time to wrap this! As I shared earlier, you should think of this substack as akin to a monthly magazine - you don’t have to read it all in one sitting, and you don’t have to read all of it! Feedback, or your own ruminations are welcome. Please use the comments to engage.

Regular readers know that this newsletter has two permanent sections:

• Writings - where I usually write and / or refer to one or more original pieces that I published in the previous months, typically about venture or the startup ecosystem. This time, there are no new writings. I am busy working on Chapter III of my PMF Playbook that I now hope to release in February of the coming year, and hence couldn’t take time out for any shorter pieces.

• Readings - about what I read and learnt about. My reading diet is tilted rather heavily in favour of books and podcast transcripts, and against articles / newsletters. This will naturally reflect in the reading list.

This is a long newsletter - think of it as akin to a monthly magazine from me (only the frequency may not be monthly!). I don’t know if you can read this entire newsletter (and peruse the links) in one sitting, and even if you do a second run ( which I very much doubt), you will have to pick and choose what to focus on. A good way to read this newsletter is to certainly read my original writing(s) below, and then glance through the rest and pick 1-2-3 items that pique your interest. Anything more is a bonus!

Readings > Podcasts

This year two VC-hosted podcasts, Uncapped by Jack Altman, and Dialectic by Jackson Dahl, entered my frequently read podcast ‘shortlist’. The former has a more conventional list of guests for a VC , i.e., other VCs. The latter is more eclectic. Both tell you that it is never too late to launch a podcast, and what really matters is clever curation of guests. I read a fair number of Turner Novak’s The Peel podcast, and Mario Gabriele’s The Generalist podcast as well, though both haven’t penetrated the ‘shortlist’. On new shows, Cheeky Pint by John Collison looks intriguing, and I will give it a go in the coming year. Re the other new podcast launch, David Senra, where David interviews guests (as opposed to his more famous Founders Podcast where he speaks aloud himself), well, that is on my list of to dos in the next few days. Sadly, two Indian podcasts I was intrigued by and planned to check out more in the coming year, both announced they are ending (Asymmetric and Everything is Everything).

My ‘shortlist’ / favourite list of podcasts consists:

VC / Investors: Invest Like The Best, 20VC, Uncapped, Venture Unlocked

Founders / Operators: Invest Like The Best, 20VC, Lenny’s Podcast

Investors / Operators: Dialectic

Biz: Founders, Acquired

AI / Misc: Dwarkesh Podcast

Misc: Conversations with Tyler, How I Write

India: Ideas of India

In addition to these, I get recommended interesting episodes of other podcasts from time to time, and I do try and consume as many of those recommended episodes as possible.

How I consume podcasts: Most of the above have transcripts, and I first open it in Safari Reader and then Export as PDF, and then save the PDF on my Remarkable, to read it over the weekend / flights. For the ones that don’t have a transcript like 20VC, or Uncapped, or any Youtube only show, I use Turboscribe to get a transcript and again do the Remarkable routine. Another transcription service you can try, which comes with a brief summary as well, is Munshi. A podcast summarising site that impressed me was Podchemy. Happy to hear recommendations of other summarising sites or tools.

Onto the podcast episodes I enjoyed the last couple of months.

The “Anaconda in the Chandelier”

Dan Wang, author of Breakneck, on the Colossus ILTB podcast w Patrick O’Shaughnessy.

Excellent one. I am glad I gave this a go. Dan Wang has been coming on a number of podcasts, following the launch of his book, Breakneck, which famously (by now) contrasts the lawyerly US society with China’s engineering-focused state. Of these appearances, the following three are recommended. One, his appearance on How I Write w David Perell, given it was focused around writing. Two, his appearance on Conversations with Tyler (notable for the to-and-fro in the early part), and, third this one, where Patrick O’Shaughnessy interviews him. After I read the transcript, I got a sense for why Patrick / Colossus ILTB is so good. The quality of questions, the probing is far higher than in others, and in response Dan lifts himself. There are a couple of memorable sections - one where he talks about his favourite cities in China (see below) and the other, where he uses James C Scott (Seeing Like a State)’s writing on South West China / Zomia as a departure point to explore why many Chinese are retreating from China. Also, I love some of his phrasing - the “Anaconda in the Chandelier” for Chinese censorship, “Chinese fire lit by the American spark” and “US sets the ladders in place, but China climbs the ladders” for how US firms invent the underlying technologies such as for Solar Photovoltaics, but it is Chinese firms which dominate the manufacturing.

Two really interesting excerpts from the podcast:

Patrick: “It reminds me of this idea that if you study Eastern portraiture versus Western, in the West, almost all of them are where your face is most of the canvas, whereas in the East, often the portraiture is a small person amidst the bigger landscape—and quite representative of the two different styles. “

*

Patrick: “If I were to take a month and travel around China—and maybe you could pick the four cities I would go visit—to learn the most and really see the bleeding-edge frontier of everything you just described…

Dan: Shanghai is my favorite city in China—maybe my favorite city in the world. It feels a lot like New York. Both have been port cities with an industrial past that has significantly moved away from them. … There’s a river that runs through both cities, and there’s a sense of hustle and ambition that one can see. It is really comfortable.

It’s a little bit like New York if the French managed significant parts of it and put in a lot of beautiful plane trees as well as cafés. I think it’s perhaps not the bleeding edge of technology as such, but I think Shanghai represents a bleeding edge of some element of consumption. You can just order food really easily in Shanghai. Most of the Uber-like Didi taxis that you would get into—almost all of them—are electric. There are parts of the city that are superbly well managed in terms of traffic flows. You can always tell how much time a red light is going to be on, and you can see this in the apps. There are all sorts of ways in which the city is very well managed. It has a subway system that doesn’t screech with that metallic noise like in New York City. As a place for consumption, Shanghai is really wonderful.

I would then hop on the high-speed rail from Shanghai to go to the city of Hefei in the province of Anhui, which is pretty close by. Hefei is probably, let’s say, two hours away by train from Shanghai. Historically, Hefei has been significantly poorer—it is much more mountainous. But now Hefei is the center of China’s electric vehicle industry, and several big EV makers are headquartered there or have operations there.

As a city, it has been growing pretty consistently. There are a lot of Chinese first-tier cities that have not been growing quite as fast anymore, but there are plenty of these second-tier cities that are growing really well. And then I think it is always worthwhile going to Shenzhen, which is in the south, pretty close to Hong Kong. I find Shenzhen probably the most boring city in China. It’s a lot of big office parks; a lot of it is meant for driving. The city layout has several big hubs connected by highways that are pretty distant from each other. Not that much interesting culture going on. People are there to hustle and to work. But it is the headquarters of companies like Huawei, Tencent, and DJI—many of China’s most innovative companies. You can find a lot of really interesting electronics there.

And you asked for four cities, so I guess the fourth one that I’ll offer is Chongqing, which is also in the southwest. Chongqing, I’ve learned, is really big among TikTok influencers. You can see a lot of these very futuristic structures carved essentially into cliffs. There are shimmering lights and this really well-known subway station that goes through the bottom of an apartment building on one side and then out the other. That creates really wonderful imagery.

It’s in the southwest, which is where my family is from. I like Southwesterners—they have, I think, the best sense of humor in China. People there tend to just sit over tea and chat. They have great food; it’s often very spicy, and it is also really dramatic. So what else could you want—great food, great people?”

“Focus is a luxury”

Thomas Laffont, Coatue, on the Uncapped podcast w Jack Altman

Enjoyable romp through a bunch of hot takes such as system of record is dead / not what it will be, how the hyperscalar oligopoly is being cracked open by Oracle and Coreweave; how he likens venture investing to a river, and while Sequoia and Benchmark have the choicest spots for fishermen to sit, he Coatue like to go up and down the river to fish opportunistically; how Coatue decides on an investment; why their top 10-15 top winners were all initial no’s; and finally this wonderful story on why you should put your everything into anything you do early on in your life. The lack of distractions at that point in time are your friend, for it allows you to focus on something, and do that well. Focus is a luxury, he says.

Thomas Laffont: “When I was at CAA, before you got to work on a desk, you had to work in the mailroom. That’s literally what it was. We would sort through mail, we would copy scripts. I’m so grateful to have had that job because when you’re starting out, I tell young people, focus is a luxury. Think about Jensen at NVIDIA today,... He can’t afford the luxury of just thinking about one thing. Generally, when you start in the workforce, you have the luxury of actually focusing on one thing. So I always tell people, that is a luxury, enjoy it.

The example that I use is during the holidays, we would send out a lot of gifts to our clients. We had a gift wrapping station. The way mostly it worked is an agent would put a gift in their app box and say, gift wrap it for me. So you would take the gift, you would go down, you’d wrap it as quickly as you could, and you’d bring it back to the agent. So I looked at it as an opportunity to differentiate myself. If I saw an agent a gift, I would take it and I’d be very meticulous on how I gift wrapped it. I started experimenting with different techniques. One that I really liked is actually putting cellophane around the paper. It just kind of gave it a really glossy feel. It looked really nice. So I went, I bought the film myself, and I would put it and I would make these really, it’s like Jiro Dreams of Sushi for gift wrapping. What ended up happening is that agents ended up seeing the nice gifts. I ended up being pulled out of my regular duties and I became the gift wrapping guy. What was nice is I no longer had to run around everywhere. I had my own little station, and for two weeks I was just responsible. As it turns out that when a desk opens, think of an agent who’s got 15 different trainees that he or she can pick from. It turns out that being known for having attention to detail and doing something well, it turns out that that served me really well. So I always think when I tell an analyst and they’re just starting, I’m like, you might only have one or two companies. Think of that model the way I was thinking about gift wrapping. Watch over every cell, every line, the formatting, what font you use. Every line has to have a purpose, because you might live in a world of 10,000 lines, but when you pitch the idea to Philippe, he’s got 17 other things he’s thinking about that moment. So your ability to crystallize that model in a way that’s simple, that shows that you understand what you’re talking about and that you can do it in 50 lines, not 10,000, is an incredible skill. A lot of how we mentor our analysts are derived from some of those principles.”

‘Fewer but better’(apologies to Dieter Rams)

Adit Abraham, Reducto AI on The Peel with Turner Novak

I thought this interview of Adit Abraham, the cofounder of Reducto, was very good. Reducto is a document parsing and information extraction software that underpins the efforts of the AI application layer companies like Legal AI app Legora uses them to ingest documents such as pdfs. What I found particularly interesting was how Tier 1 VCs woo elite founders, such as Chetan’s (of Benchmark) ‘low pressure’ dinner strategy, and then how their $75m Series B round closed in 48hrs. Clearly, in the upper tiers of founders / startups, the founders pick their Captable. Now, just as VCs chase hot founders, these hot founders chase top engineers. There is a fun story on how the Reducto founders wooed a top machine learning engineer who had done his PhD in the exact space that Reducto was building in, by flying to Indiana on a red eye, brushing in the airport toilet, and then rushing to Purdue campus for a 7-hr long meeting. What I found particularly interesting, was how their focus on trying to be great in a few use cases versus trying to be good in many, paid off. If SaaS is narrow ICP and broad usecases within (eventually), then in a way, AI is wide ICPs and narrow usecases.

Adit Abraham: “To start, all we said we would do is the very first thing that we decided to train our own model for, was we wanted best in class layout detection and understanding. And so, we spent a lot of time building that and just being incredible at layout understanding. And then from there, we decided we wanted to be incredible at table parsing and table detection. And so we spent a ton of time on that and these are broad horizontal problems. If you have great table detection, it ends up applying to a bunch of different industries and same with layout and the other things we did. But it was this iterative process of growing the scope, but for every individual stage, we made sure that we felt like we were incredible at what we were doing. And I know you mentioned this earlier of there were pretty good solutions available when we started, I think one of the closest comparable companies to Reducto when we first got started, along this idea of unstructured data for LLMs, had this thesis around you can upload any file to this platform. They had 35 different file types.

…

Adit Abraham: And a lot of our early customers were actually churned customers of theirs. And I talked to them, I was like, “What didn’t work?” Whether they needed us to support that many file types because there was no way we were going to do that on day one. And they were like, “No, actually, we only really have two to three types of files that really matter. This is the 80/20 or 95/5 in our case, and we just need those done incredibly well and we can’t spend all this time with okayish pipeline for things that we don’t even care about when the things that we do care about, don’t work.” And that was really important. It’s like, it was okay that we weren’t competing on number of file types. We were just competing on for the people that needed PDFs and images, great, Reducto, it’s a solution for you. And then gradually expand it from there.”

“Sucking supervision through a straw”

Andrej Karpathy on the Dwarkesh podcast.

This is the one which went viral for Karpathy saying AGI is at least 10 years away. Now, there is a lot here I didn’t understand, and I did have to use ChatGPT to understand some of the more technical stuff, but very useful to get his perspectives on why Reinforcement Learning is bad (well, better than everything else, but bad) because it rewards even bad approaches taken along the way to get to the right answer [Karpathy, ever the coiner of evocative phrases (such as ‘vibe coding’) describes RL memorably as akin to “sucking supervision through a straw”] , why wages in AI-impacted professions will rise (provided talent is non-fungible) as a result of bottlenecking (scarce human talent becomes even more valuable thanks to AI leverage and AI monitoring), and why the constant ‘march of 9s’ makes it hard to hit AI-led automation on anything mission critical. Recommended.

Dwarkesh: ” With radiologists, I’m totally speculating and I have no idea what the actual workflow of a radiologist involves. But one analogy that might be applicable is when Waymos were first being rolled out, there’d be a person sitting in the front seat, and you just had to have them there to make sure that if something went really wrong, they’re there to monitor. Even today, people are still watching to make sure things are going well. Robotaxi, which was just deployed, still has a person inside it.

Now we could be in a similar situation where if you automate 99% of a job, that last 1% the human has to do is incredibly valuable because it’s bottlenecking everything else. If it were the case with radiologists, where the person sitting in the front of Waymo has to be specially trained for years in order to provide the last 1%, their wages should go up tremendously because they’re the one thing bottlenecking wide deployment. Radiologists, I think their wages have gone up for similar reasons, if you’re the last bottleneck and you’re not fungible. A Waymo driver might be fungible with others. So you might see this thing where your wages go up until you get to 99% and then fall just like that when the last 1% is gone. And I wonder if we’re seeing similar things with radiology or salaries of call center workers or anything like that.”

Bowling alone, and Soulcycle as simulacrum

Eugene Wei on the Dialectic Podcast w Jackson Dahl

Loved this episode. Fascinating digressions across a bunch of topics - tech, community, social networks, AI, film-making etc. Eugene’s catholic interests and reading (a range of books across tech and culture are mentioned) come through strongly in the episode helped by Jackson’s questions. A core theme in this episode is how tech’s relentless focus on removing friction makes it easy to consume anything instantly and from the comfort of your house, but ends up reducing social interaction and leads to decay in community. This has long-term implications for discourse and democracy. As a result, we are seeing appeal for brands such as SoulCycle (and Crossfit a decade or so back) that provide community elements. Sports teams are of course the preeminent example of this; effectively they are minireligions / cults.

Eugene: “Putnam’s book Bowling Alone, I think I read that around 2000, came out prior to a lot of these things. But I would argue that since Bowling Alone came out, a bunch of things have further exacerbated the problems he was pointing to. One was the huge rise in cable news. I would say Fox News is probably the most disruptive. Then we had the Internet, the smartphone, and social media. Then social media got big, then we had the pandemic and remote work. I think each of those things further frayed the bonds of community in the West and reduced these communal meaning-making structures that we used to have.

It’s to the point now where I think it’s going to be a real challenge to figure out how to reassemble it. What you see people doing, I think, who are trying to seek some form of community, is that they just look for it in anything that they can find. I’ll never forget going to my first SoulCycle class. My friend took me up in Marin County. It had this strange, cultish feel. There were all these candles lit. It was dark. They were playing loud music. It was like some crazy interrogation. At some point, this woman next to me was crying.

I feel like this explains some of the cultish feel of America now. People are just seeking the simulacrum of community in anything. Businesses that do well try to play a little bit on this. Even in the crypto world, some of these DAOs and meme coins are a weird fusion of everything modern. It’s like this synthetic community bonded around hyper-speculation.

The class hierarchy in India’s judiciary

Prashant Reddy and Chitrakshi Jain on the Ideas of India podcast w Shruti Rajagopalan

A bit late to this really hard-hitting (and a tad depressing + infuriating) episode covering how High Court Judges in India have immense power over the careers of district judges, including the ability to force them into compulsory retirement (without recourse) and how that leads to a chilling effect at the District Judges level. Covers many examples of this, as well as the many indignities that a District Judge has to go through such as receiving the High Court judge at the railway station, eat in a separate dining room at the National Judicial Academy etc. I have really learnt a lot about the Indian legal / judicial system via @srajagopalan ‘s podcast episodes. I would certainly say that there is some serious repair work needed in our Legal / Judicial system, if we need to accelerate growth. While it is not the only reason, it is a rate-limiting factor for sure.

“RAJAGOPALAN: What is going on in our judicial system that the supreme court and high court operate as this other worldly judicial system and the way these opinions are written, some of which you’ve reproduced, they really look down upon the lower-tier judiciary as if these people are criminals and not qualified.

I don’t know if I’m reading a small select thing, but it seems extremely classist and biased and elitist. All my capture theories disappeared, which really disappointed me. I was like, “What is going on here that these guys are not sticking with each other?” What’s the institutional or structural reason?

REDDY: Yes. It is. There’s a very clear class hierarchy. I think part of it goes back to the British era where high courts were staffed by white men from Europe and the district courts, except for the district judge would be an ICS officer. The lower levels would be staffed, again, by the natives, so to speak.

That’s definitely one part of the story of why it’s so feudal. I was invited to the National Judicial Academy a long time ago to give some lecture. I was surprised that even in the dining area, there’s a separate dining hall for the high court judges—

RAJAGOPALAN: Of course, there is.

REDDY: —and a separate one for the district court judges. We see this playing out in different ways. We’ve heard some stories from retired high court judges, district court judges going to greet, receive high court judges at the railway station.

RAJAGOPALAN: Yes. They go to the railway station, they all stand with garlands. It’s all very strange.

REDDY: The hierarchy is very clear. The high court judge is like your Secretary Babu. The district court judge is your local MRO, Mandal Revenue Officer, or lower than that. “

Readings > Articles

On why VCs should not select for the power law

The Map is Not the Territory: Why Venture Capital Misunderstands the Power Law by Aki Kakko

Good piece by Aki Kakko on why VCs should not select for power law, but for resiliency, non-consensus (lower asset prices) and potential for uncapped upside. The power law, he says, is a system property of markets like venture, that have limited downside and unbounded upside. It is not a selection mechanism. You can only engineer the conditions for power law to emerge, not select companies that you think fit the power law.

This is one of three posts that Aki Kakko wrote on venture that I found interesting, and made me think. The other two were this one on how VCs are driven by the fear of looking stupid, and the last on how the venture model should shift from the present pitch-based model to one where the VCs use software to track the startup for investment.

How USV and Ribbit Capital created some of the most succesful venture outcomes of all time

The Allocator’s Notebook: USV Funds I-III, and The Allocator’s Notebook: Ribbit Capital I-III by Yavuzhan Yilancioglu

Ex-LP Yavuzhan Yilancioglu deep dives into the investment strategies underpinning the first three funds of USV and Ribbit Capital, and deconstructs fund performance including estimates of the performance metrics. This is true public service for venture nerds.

Act 2 and investing alpha

The Last Human Edge by Dom Cooke

Love the @joincolossus profiles of legendary investors (but often less-known, atleast to me); this one, by @domcooke was another of those. Good piece on how Henry Ellenbogen and his team have created a distinct public market (and late stage growth) investing style, backed by their frameworks around Act 1 and Act 2, to identify compounders, or highly durable businesses. Venture nerds will find it interesting for the focus on people, and for Henry going beyond mere DCF calculations, in evaluating late growth ventures.

On creating context and conditions for manufacturing’s ascendancy

China’s Age of Apprenticeship (2015 - 2025): The Decade The Rest of Us Can’t Skip by Alysha Lobo

“When I walk a line I smell hope and exhaustion. I smell the coolant and the varnish. I hear the operator calling for a new jig, the engineer scribbling a note about a stray burr. Those moments are invisible in policy briefings. They are the moments where tacit knowledge is born and where industrial competence grows.”

Good writing by Alysha Maria Lobo on the levers underpinning China’s manufacturing ascendance, and why there are no shortcuts to achieving this. This is also a good read for folks in India’s policy think tanks - this is a better snappier read than any of the stuff I have seen come from Indian policy think tanks on this topic (if you have then point me to it).

If you liked this do check out Alysha’s other posts (on her TechnicAly Speaking substack). In my last newsletter, I highlighted two essays by her on Indian Tier 2 cities Hubli, Belgaum, and their emergence as manufacturing / industrial minihubs. This interview of Alysha on Dharmesh Ba’s newsletter is a good one too.

A narrow ICP ≠ narrow TAM

Selling to Carol, by Jason Cohen

Exceptional piece of writing (one of the best I have come across on ICP or Ideal Customer Persona) on how targeting a narrow audience base will not limit your audience base at all.

YouTube content secrets

An Interview With a YouTube Writer Behind 500M+ Views from Human Invariant blog

Really interesting interview with a YouTube writer (from the Human Invariant blog, one of my recent discoveries). Lots of interesting factoids such as:

“There’s an argument that having early engagement from “superfans” in the first hour or two helps to improve your early metrics, and the theory is that this would get YouTube to push your content out to more people, because in the first hour you had people who were leaving a comment and “liking” the video. I can’t confidently say it has zero effect, but it’s minuscule in comparison to overall clickthrough rate (CTR) and retention. Overall my more general heuristic is that you don’t need to treat the launch of a new video as a “make or break” event where if you fumble things on day 1 things will be ruined forever. “

Incidentally, I had also recommended a piece by him in my last newsletter: Notes on Shadowing a Hospitalist.

Data centers, water consumption, power bills, and top soil loss

Inside the Data Centers That Train A.I. and Drain the Electrical Grid ​​by Stephen Witt

Enjoyable read, giving you a look at Data Centres, the engines / factories of the AI economy

“I asked the farmer if he had noticed any environmental effects from living next to the data centers. The impact on the water supply, he told me, was negligible. “Honestly, we probably use more water than they do,” he said. (Training a state-of-the-art A.I. requires less water than is used on a square mile of farmland in a year.)

Power is a different story: the farmer said that the local utility was set to hike rates for the third time in three years, with the most recent proposed hike being in the double digits. The biggest loss was the nutrient-rich topsoil, which his family had maintained with careful crop rotations. “Microsoft brought in an excavator and ripped it all out in a day!” he said, as if speaking of a lost heirloom. “Six to ten feet of it, all gone.”

Bye!

It is time to wrap this! As I shared earlier, you should think of this substack as akin to a monthly magazine - you don’t have to read it all in one sitting, and you don’t have to read all of it! Feedback, or your own ruminations are welcome. Please use the comments to engage.

This is also very likely my last newsletter for the year. I wish you all a very happy new year, and hope you are able to get some downtime in the coming few days.

On that note, signing off for the year!

Regular readers know that this newsletter has two permanent sections:

• Writings - where I usually write and / or refer to one or more original pieces that I published in the previous months, typically about venture or the startup ecosystem. This time, there are no new writings. I am busy working on Chapter III of my PMF Playbook that I hope to release towards the end of the year, and hence couldn’t take time out for any shorter pieces.

• Readings - about what I read and learnt about. My reading diet is tilted rather heavily in favour of books and podcast transcripts, and against articles / newsletters. This will naturally reflect in the reading list.

This is a long newsletter - think of it as akin to a monthly magazine from me (only the frequency may not be monthly!). I don’t know if you can read this entire newsletter (and peruse the links) in one sitting, and even if you do a second run ( which I very much doubt), you will have to pick and choose what to focus on. A good way to read this newsletter is to certainly read my original writing(s) below, and then glance through the rest and pick 1-2-3 items that pique your interest. Anything more is a bonus!

Readings > Podcasts

“If it on the business pages, then it is too late”

Richard Rainwater’s profile on Rainmakers podcast by Rame Adi. Link to podcast episodes with transcript: first episode and second.

Rainmakers, by host Rame Adi, is a new podcast that I have been impressed by. Think of it as the love child of David Senra’s Founders Podcast with Byrne Hobart’s The Diff. This is business history done well. If you love Founders Pod, then you will like this! I came across the podcast after I first heard about Richard Rainwater in a podcast of Graham Duncan, and then tried to find more about him online. Richard Rainwater was widely considered to be an astute investor, and also an equally impressive backer of investor / managers (Duncan references him in the podcast in the latter context). Rainwater is who is profiled in the first two episodes of the podcast. These are excellent, and well researched episodes. Recommended.

Rainwater: “My objective is to capitalize on major one time transformation in an industry or company….Most of the time, the critical information that enables me to identify these significant changes is found not on the business pages of the newspaper but on the front page. (In fact, if industry changes are highlighted on the business pages, it is usually too late for my kind of investing).”

…

Rame Adi: Rainwater’s network was the most important part of his investing success. He focused so much on being in deals and would notoriously be in hundreds of calls throughout the day seeing what ideas people had for him to pursue. He would also go out to New York all the time for the Basses when he started in the 70s and would travel throughout the country to meet with any manager or banker that can give him a lead on an idea. As his image in the financial community grew he did not need to travel but instead would have investors constantly call him or visit his office. He did not treat his office as some sort of secret place where he works on his investments, he was very open. Almost too open.

His secretaries would line up meetings throughout the day and empty conference rooms on his floor would be treated as a doctor’s office with multiple investors waiting per conference waiting to make their pitch to him. In the 80s and 90s there seemed to be no barrier into actually getting a meeting with Richard Rainwater. Many of the people that did deals with him when he went off on his own all got jobs by sending letters to his office. Ken Hersh describes this moment very clearly when he sent his own letter asking Rainwater for a job where Rainwater would cold call him back around a week later asking to meet with him. Having this open office of sorts allowed Rainwater to see deals of all kinds while meeting experts in various fields should he actually seek their expertise. Without this constant flow of information I don’t think Rainwater would have made a lot of the deals he ended up doing.

“You are advertising to a moving parade, not a standing army.”

David Senra on the Dialectic Podcast w Jackson Dahl

This is easily one of the top podcast episodes I read this year. So much to unpack here, like a suitcase that you were struggling to close after purchasing too many books during a trip. Weeks after I originally read it and posted about it, I revisited it for writing this post, and it still felt fresh. A lot of the episode’s resonance to me has to do with David Senra himself. He is fascinating to me, and I daresay a lot of us, because of how he has pared his life down to utter simplicity, built around what he truly enjoys doing. That is, read one or more great biographies of a figure, and talk about it for a (riveting) episode a week. The equation is 40 yrs of a working life, 40 hrs of reading about it, and 40mins of his episode, as he described it once.

The same week this episode dropped, there was a David Senra episode with Tim Ferriss as well. Though on the whole I preferred this one (Dialectic). Got a lot more insights here, I felt. Some of these insights:

– Senra is one of the biggest listeners of his podcast, including past episodes. It is the equivalent of athletes watching their game tape.

– “You are not advertising to a standing army. You are advertising to a moving parade” – David Ogilvy. Senra thinks we all don’t repeat enough. The audience is changing. People forget. Republish your old stuff, he says. Repetition doesn’t spoil the prayer.

– When you have an outlier thought, say it. Not everyone will like it, but the few who do will love it deeply.

– You need to sit with content longer. He says “I’m anti-redlining information fast or listening to podcasts on 3x speed. The point is you need to sit with it longer….You can rush through sex, but that’s not the point. Your goal when you’re going to make love is probably not, “Let’s see if I can get this over within two minutes.” That’s not the point.”

– Do a business based around an activity you like doing for its own sake; in Senra’s case it was reading. If you don’t then you will give it up when you get richer, or will get bored with it. If so, you lose the power of compounding that comes with sticking to it over a long period of time.

– Commitment is freedom: “I think most humans are very scared to commit to something. They want to maintain optionality….You’re not going to distract me, because I know that 99% of the people on the planet cannot focus on a single thing for a long period of time. That’s why 99% will never be great at what they do. It is very important for me to be really great at what I do, if not the best in the world at what I do. As someone who is very freedom-seeking, the most freeing thing is commitment. When you commit, the other stuff drops away and you’re free to run.”

Senra: “You see this with Peter Thiel. He goes and gives talks on the Antichrist and other stuff. What we want from him is to repeat *Zero to One* over and over again. If you only read one book on startups, it’s obviously the book.

There’s this desire… Humans crave novelty: “No, I created great ideas, so now I have to do something new.” No, you have to repeat it over and over again. I’m fascinated with people that do things for a long period of time. I’m not interested in the “start, scale, sell.” Go do that. I’ll just keep dominating for decades.

….

I contemplate what causes things to last and endure for a long period of time. There’s this great line in *Poor Charlie’s Almanack*. Charlie’s son says that he thought his dad thought durability was a first-rate virtue. That’s a fucking powerful idea. Durability is a first-rate virtue. In this modern environment, we fetishize growth at the expense of durability, which is a massive mistake.

If you analyze the people that last a long time—what has Buffett been talking about for 60 years? What has been important to Michael Dell for 40 years? I just did this crazy episode on Elon Musk. You wouldn’t expect it from him; you think he’s running seven companies, obsessed with technology. He repeats the same thing so much that the executives in the meeting can mouth the words before he says it.

So why are you jumping from idea to idea to idea? You have to identify a handful of timeless principles, repeat them, work on them, and make them the center of your work for decades. That’s how greatness is built.”

Excerpts from the podcast that I thought were particularly relevant linked here.

Are the Humanities less audacious in scope than before?

David Brooks on Conversations with Tyler

One of those really hard to categorise / summarise podcasts. In fact the best writing is one that is hard to summarise (think I heard that from Taleb). Brooks and Cowen cover a wide range of topics but the key themes are the decline of audacious works (novels, paintings, music) in the humanities today (tech is now the sphere where audacity is widely seen), the underweighting of emotions and passions as opposed to reasoning and rationality, the fraying of the civic fabric in USA in recent times and why he thinks this is the rupture phase and will be followed by a repair phase. A wide range of topics and one that is hard to pin down, in the best way possible. Highly recommended.

Brooks: Well, go to the 19th century, to the glory days. Charles Dickens literally changed the imagination of Britain by altering how people saw poverty. George Eliot literally changed the moral life of Britain, because as religion was fading, she presented another moral structure that people could sign on to. These novelists had these huge effects. …We now live in a moment of great public tumult, a moment when our interior lives are directly affected by the trauma of our public lives. If there’s a novel that’s capturing what it’s like to live in this era, I’m not aware of it. I think this would’ve been a great era for a Balzac, for a Tom Wolfe, for that kind of social realist novel. In my view, the audacity is not there. In this column, I don’t know what—

Cowen: Audacity is the scarce factor in your account?

Brooks: I think it’s a scarce factor. I don’t know what you would think of this, but I think back to when I was a teenager in the ’70s, and I look at the movies like Apocalypse Now, The Godfather—they seem big audacious. I listen to the rock songs I was listening to, “Free Bird,” “Stairway to Heaven,” “Bohemian Rhapsody” —they seem just more audacious.One of my heroes is an art critic named Kenneth Clark. He goes through the great high points of Western art. Those high points are defined by audacity. You look at the Renaissance—that was audacious. You look at the Russian novels—that was audacious. I think we’re just not at a moment where that kind of self-confidence—which is very hard to manufacture for one person; it takes a whole group—I just think we’re not at that moment.

Cowen: Building AI is audacious, right? Trump, whatever you think of him—he’s clearly audacious. You wouldn’t say the quality has left our culture, so why has it left the novel?

Brooks: I think it’s left the humanities. I think the humanities have been backfooted, in part because, again, internet, all that stuff, the obvious stuff. ….I think that big ambitiousness is less encouraged now for whatever reason.

Link to excerpts from the podcast episode I found particularly interesting.

The venture arrogance score

Josh Kopelman, First Round Capital, on Uncapped Podcast w Jack Altman

First Round Capital is one of the, if not the leading seed fund(s) in USA. Josh Kopelman who cofounded it just over two decades ago, makes an appearance on the Uncapped Podcast. There isn’t anything dramatically new here barring of course the venture arrogance score concept that Josh introduced. That, and a short passage on how they have a role of a non-investing partner, Brett Burson, who manages the firm, was interesting. They think of investing (or not investing) decisions as one of the key products that gets shipped by the fund, Brett’s role is to help improve decision-making as well as help create platforms and run initiatives that aid in the form being better able to serve the founders.

Josh: “ I’ve created something which I don’t think I’ve shared publicly. Let’s call it the venture arrogance score. All right. So you take a fund, say that fund is a $7 billion fund. Then you look and say, so you need two numbers to understand any fund’s business model. First is how large is the fund? 7 billion. The next is what percent of a company do you think they’ll own on exit? And so like, are they going to own 30% like they did 20 years ago? Or are they going to own 8% or 10%? And like today it’s trending to 10%.

So if you have a $7 billion fund and you’re going to own 10% of the companies that you’re in on average, you just figure out, okay, for each turn of the fund, that’s $70 billion, right? Like the founders need to create $70 billion worth of value in your basket for your 10% to be worth 7 billion. So if you want to, now, if you’re still aspiring for a 4x gross 3x net, which is sort of what like the venture long-term aspirational goal was, you’re now saying, okay, so for each turn of the fund, that’s $70 billion, so call that $280 billion. And here’s where the arrogance scale comes in.

Because say you raise that fund every three years, you know, that’s roughly $90 billion a year of exit value that you hope to extract out of the market. And how much is exiting total? Well, like the last decade was the best decade ever. Yeah. $1.9 trillion total of US venture. And that includes pharma and everything, like semiconductors. So that’s an average of $180 billion a year.

So it’s like, you need to catch half (50% of $180b = $90b). By the way, to my knowledge, there hasn’t been a venture fund that has ever repeatedly caught over 10%. So you’re saying that you and your fund in this hyper- competitive environment with 10,000 funds and 20,000 plus check writers, you are going to capture half of all venture value created every year for the three-year period in your fund just to generate that.

The venture arrogance is trying to figure out what percent of total value created by all founders anywhere in the United States you have to capture for your fund model to be successful.”

Link to excerpts from the podcast episode I found particularly interesting.

Don’t give a job offer to a great candidate on a friday!

Nakul Mandan, Audacious Ventures on the IO Podcast w Tyler Hogge and Sterling Snow

Good episode with specific actionable input on how to run a high quality hiring process by Nakul Mandan of Audacious which gives talent a seat at the high table. He says: recognise that if you are after a great candidate, there will be a lot of competition for them – you have to be continuously selling your co, and inspiring them emotionally, not just logically. There should be high clarity on the job role (use the Mission – Outcome – Competencies framework). Make sure you have a decent pipeline (at least 10 good candidates says Nakul), and have a sharp intentional vetting process. Finally remember to close with urgency, and never give an offer on a friday.

Nakul: “Once you are ready to make the offer, that last 72 hours is key. That’s when they are. So I’ll give you a tactical example. So if I like a candidate, even when we are recruiting at Audacious and I will never let a Friday happen where they’re going into the weekend, they don’t know where they exactly stand. Why? Because weekends is the time when a candidate is talking to their mentors, their plus ones, whoever matters to them in their decision. Or they’re just mulling it over, right? So if you’re letting the weekend happen when some other offer is on their mind or something else, then you’re wasting that time. And whoever wins the weekend, if you’re especially trying to close in closing mode, you should just be all over that weekend. The more time they’re spending on you, the less time they’re spending on something else. Now that’s a competitive, let’s say it’s a competitive situation. Then what you do is you get three of your own supporters, text the person, right? And respectfully text the person and keep the excitement high. So you don’t take two. But if it’s a competitive offer and there are three offers, whoever wins that time, no matter what the candidate says, whoever wins the mind share, whoever wins the weekend, wins the candidate.”

Link to excerpts from the podcast episode I found particularly interesting.

Other podcasts I enjoyed

Dwarkesh Patel on the Uncapped Pod with Jack Altman explains why AI is not particularly useful to him, nor anyone who needs the job to be 100% perfect. The fundamental issue he says why AI is not better than a human is that the human is continuously learning on the job while the AI’s learning is limited to a finite time frame (typically in session, and after that it loses context). AGI he says is still some time away, at least a decade.

Rajeev Samant on the Blume Podcast with host Karthik Reddy. I am biased of course, but I loved this episode. The alcohol category is one of the hardest ones to build / launch in India and in that respect what Rajeev Samant was able to do was nothing short of outstanding. He in fact had to write out the policy paper under which led to the issue of a license to manufacture wine. The entire story of how he left Oracle to come back to India and settle on wine making as his profession was a riveting read.

Joe Leimandt, the founder of Trilogy Software, came on Colossus’ Invest Like The Best podcast to talk about Alpha School, the AI-led reimagined school he has founded. Fascinating episode, and there is an accompanying article as well that covers similar ground. I shared this with a friend who has run and sold a K12 school and he seemed sceptical but there is lots of buzz about it on the interwebs, and overall I got the feeling that the hype seems somewhat legit. If you want to explore further check out this review of Alpha School.

Peter Lacaillade, SCS Financial on Colossus Invest Like The Best. Fascinating glimpse into how an elite GP looks at venture capital and other alternative asset management segments, such as Search Funds and Bootstrapped Growth Equity. I found the Search Fund segment fascinating. I see the Search Fund sector today as akin to how venture capital was in the ‘70s / 80s. The equivalents of Don Valentine and Sequoia for the Search Funds are emerging, and in the coming decade, I think it will occupy similar mindspace to what early stage venture is enjoying. Link to excerpts I found interesting.

I have really enjoyed reading the How I Write podcast transcripts. The ones featuring Jimmy Soni, who is writing a book on Kobe Bryant, and this one where Dan Wang talks about his book ‘Breakneck’ on USA v China, were both enjoyable. (Excerpts from the Dan Wang podcast episode transcript I found interesting here)

Readings > Articles

Why don’t all restaurants invest in training waitstaff?

Aligning Business Models to Markets by Kevin Kwok.

This is one of Kevin’s older pieces broadly around the theme of how industry structure shapes business model approaches. He illustrates this through two examples. The first is from the restaurant industry, where he describes restaurant conglomerate Union Square Hospitality Group (USHG), which practices a service-heavy approach, supporting it by investing heavily in service training. Kwok, asks why other restaurants don’t do it, and draws out that USHG can afford the higher than usual service costs as it can offer its staff the luxury of being able to move within the different restaurant brands in its portfolio, and thus try and ensure that they can retain the trained staff within their group. The reduced churn helps in lowering overall costs, and getting better human capital leading to improved service, and better business. The second example he cites is of the gaming industry where always-on internet connectivity has shaped the gaming business model first towards subscriptions / recurring payments, and then towards a freemium model where the game is free to play, and is monetised via in app purchases.

“Danny Meyer and the Union Square Hospitality Group are a good example of how we often discuss the first order cause of things, without understanding the structural systems shaping them. People reading Setting the Table often talk about being more customer focused. But they don’t understand that it’s not about trying harder. It’s about setting up a their business model to align with prioritizing customer service. And identifying spaces where that can happen. Similarly, I recently read a question by Jack Altman on advice. My personal view on advice is that most people suffer from the same first order mistake. They say what they did that worked. But they don’t elaborate on the underlying structural features of their situation that would need to be true for their advice to be applicable in a new situation. But we often see people say advice isn’t useful, because nobody is discussing these structural alignments. It’s like watching someone try to uproot a plant to the desert–without paying attention to what soil, sun, and watering conditions it thrived in. And then be shocked it died.”

Container theory

Container Theory: Behaviour is a Liquid, by Chris Sparks

Create supportive conditions that help you do more of what you want to do (laying out the morning running gear out at night) and less of what you want to avoid (remove sugar from the house). These conditions are containers that help shape our behaviour. Eventually as we do these desired actions more (or reduce undesired actions) these actions become part of our identity itself. Eventually we don’t need these enabling conditions or containers to express our identity. Being a runner or being metabolically healthy becomes core to our identity itself.

“… years of working closely with top performers shattered this myth. The compounding advantage isn’t discipline—it’s the intentional cultivation of conditions that support excellence.

This morning, I had a great workout. Last night, I laid out workout clothes and was accountable for meeting a friend at the gym who happens to take his workouts very seriously. It is probably a good idea to recreate those conditions.

The same principle applies to not-so-good outcomes. One night, while traveling, I raided the candy in the hotel minibar. Upon reflection, I didn’t eat a full dinner, and the candy was left dangerously close to the bed. I’ll experiment with hiding the snacks in the closet for my next stay.

When shaping your container, act as if you have free will. When you’re taking action, assume you don’t.

Make what I want to do more, easier to do. Make what I want to do less, harder to do.

Instead of pursuing goals directly as a first-order cause, I encourage goals to happen as a second-order infinite game. The results appear magical, but the process resembles gardening more than wizardry. A gardener doesn’t force the plant to grow—they cultivate ideal growing conditions and allow nature to take its course. “

In the age of AI, VCs should focus on access that can’t be automated

Are We Underestimating How AI Will Change Private Markets? by Donald Lee-Brown and Terran Mott

Good piece on how AI is influencing and impact private market investing. TLDR: When everybody has AI, and every analyst is using Harmonic and god knows what else to source on steroids, then alpha moves to ‘access that can’t be automated’, i.e., whatever cannot be parsed and analysed using AI tooling is the read advantage to have.

This example below of how Bloomberg democratised information, leading to the alpha then moving to being liked, is going to repeat in the early stage VC game too, e.g., If every analyst is going to ping a founder who puts ‘Stealth Mode’ or ‘Building something new’ on his / her Linkedin Profile, then the alpha now is to get the founder to call you before they even start up.

“…after Bloomberg democratized market information, trust mattered more. In a world where other advantages were vanishing, cultivating personal relationships was an enduring way to maintain access to clients. After Bloomberg, he explained that entertainment budgets “actually went up, because dealers realized [that] now I need that customer to want to call me, instead of the other way around. All of a sudden, I need them to call me. Technology definitely drove that … As we got into a Bloomberg-driven world where everybody had all the information, then you were trying to get an edge by spending money to get the client to like you, to trust you.”

…

“As more and more firms adopt these low-cost tools, the ability of these tools to reliably deliver opportunities will get increasingly diluted. At some threshold, their primary contribution will be noise. A founder who receives one or two cold inbounds personalized with AI may reply; a founder who receives hundreds of such messages predicated on the same leading indicators will almost certainly not. This pattern has already played out in enterprise sales and hiring. We think that adoption of automated, infinitely personalized sourcing tools in PE and VC over the next few years will lead to the same pattern. In turn, the ability of a firm or investor to create access that can’t be automated will become critical. Through this lens, firms that have already built this through a strong product or brand stand to increase their dominance.”

Status games

Palantir’s Weirdest Book Recommendation by Mario Gabriel

Good read on the weird book that Palantir includes in the incoming employee book bag – ‘Impro’ by theatre guru Keith Johnstone. Mario Gabriele reviews ‘Impro’ after wondering “Why would a vendor to the military ask its new recruits to study the ponderings of a former associate director of London’s Royal Court Theatre?” At the core of it, he says Impro helps you decode the status games being played in social & corporate settings, incredibly useful for a FDE to navigate the client’s organisation and get to the outcome.

“If there is one thing to take away from Impro, this is it: status transactions occur everywhere, all the time, and are unavoidable.

While teaching improvisational theater at the Royal Court, Johnstone found his actors struggling to speak naturally. He tried various techniques before landing on his “status transactions.” Actors in a scene were instructed to set their status a bit above or below their scene partner’s. Johnstone asked them to do so as minimally as possible. As he tells it, the impact was immediate: “The scenes became ‘authentic’ and actors seemed marvellously observant. Suddenly we understood that every inflection and movement implies a status, and that no action is due to chance, or really ‘motiveless.’ It was hysterically funny, but at the same time very alarming. All our secret maneuverings were exposed.”

If transactions are so omnipresent, why don’t we notice them more often? In Johnstone’s view, social etiquette “forbids” us from seeing these minor machinations, meaning that we only notice them when in direct conflict.

…

It is not possible to be “status-neutral.” In every interaction, you – and those around you – are either playing high or low status. The inflection of someone’s voice, the volume of their speech, the movement of their hands, and the stories they choose to tell about themselves – all contribute to the status they are playing.”

Good books are akin to “soda cans left in a hot car”

How I Read by Henrik Karlsson

I discovered Henrik Karlsson recently, via David Perell’s How I Write podcast, where Henrik made an appearance. I haven’t read a lot of Henrik’s work (my fave thus far is his piece on the childhoods of exceptional people) but I find it interesting enough to suggest you should check his blog Escaping Flatland out. His new piece on how he systematically searches for books to read is fascinating. He puts in a lot of work to locate the 300 or so books he starts, and the 50 he ends up finishing. This essay is about that. It ends with an arresting metaphor for good books. See below.

“Good books are compressed thoughts. They are like soda cans left in a hot car: when you open them, the content explodes from their container, spraying and spraying—pouring out much more than it seems reasonable a little can like that could possibly contain. In seven hours, I can read a book of thoughts that someone spent two years thinking. There are few ways of spending seven hours that can compete with that.”

Other articles I enjoyed

Radhika Agarwal, founder of a soon to launch skin health brand, has been writing a newsletter at the intersection of skin health and science called 1 am skincare club. I like her honesty, reflected in this piece about her struggles with acne, and her nerdiness as in this piece around popular acne treatment brand Accutane and why you should be very careful about taking it. This one where she reviews the recent WTF episode on Beauty was one I enjoyed deeply, given it saved me 3+ hrs of watching the episode, but also because it served up insights such as “Interestingly, I now see a lot of affluent urban Indians pushing for buying local – be it moving to Gully Labs or Comet for shoes, Mokobara for luggage, or Samsara for gin. We’re perhaps in a unique phase where ‘Made in India’ is becoming cool for western-exposed affluent Indians, but international is still aspirational for middle India.” Full disclosure: As an investor in her soon to launch startup, I have ‘skin in the game’ (sorry if you pun snobs think it too obvious!) and conflict, but this is an excellent newsletter to check out.

Notes on shadowing a hospitalist. Excellent article detailing observations from following a hospitalist (In India this would be an internist, it seems). This is from an anon blog, with lots of good posts such as this one on audience growth and content and this one on high income work. Hard to easily classify but one of several anon blogs like Applied Divinity Studies, Psmith’s reviews, and the not so anon Slate Star Codex / Astral Codex Ten that cover tech and tech-adjacent topics through a rationalist / tech thinking / silicon valley lens.

The World in Which We Live Now by Nassim Nicholas Taleb. A glimpse into how Taleb is thinking about the world. The observations about immigration are perceptive. The quote “Every Western political party that won office on an anti-immigration platform has ended its term with more immigrants than before.” is telling.

AI Will Not Make You Rich by Jerry Neumann. Provocative piece arguing that much of the value from AI will be spread thin across different industries, and will not be captured by startups. In this regard, the author compares AI and investing in it to the introduction of containers — where no firm was able to monetize the tech. This is contrasted with Information & Communication Tech where a lot of startups were able to capture value and monetize the IP.

The Jensen Huang Playbook by Mario Gabriele in The Generalist (paywalled). Fun read, though nothing new as such to Jensen watchers. And, again, a lot of the playbook is unique to Jensen / NVidia and is hard to replicate in another place. Still, I found it a good read, and Jensen Huang’s philosophy of focusing on the essence of the Industry (the core constraint point that sets everyone’s cadence) and going after zero-billion markets (nascent / early markets) stood out from this piece. Since this post by Mario Gabriele is paywalled, pointing folks to David Senra’s podcast on Jensen Huang (free to access incl transcript) which broadly covers these concepts. Excerpts I found interesting from David Senra’s are linked here.

Dom Cooke wrote a compelling profile of Thomas Peterffy, founder of $100b-valued Interactive Brokers, and also the world’s 23rd richest man. He built a handheld computing device (before the iPad) so his traders could have an information advantage on the trading pits. He also created his own options pricing model before Black-Scholes model. This profile appeared in Colossus Review, part of the Colossus podcast network. Colossus (across the podcasts, and the Review) is my most consumed media property, and crazily, much of it is free.

Other articles I enjoyed included this review of B2B sales guru John McMahon’s ‘The Qualified Sales Leader’ and Alysha Lobo’s writing in her TechnicAly Speaking substack, especially the two essays on Indian Tier 2 cities Hubli, Belgaum, and their emergence as manufacturing / industrial minihubs.

Bye!

It is time to wrap this! As I shared earlier, you should think of this substack as akin to a monthly magazine - you don’t have to read it all in one sitting, and you don’t have to read all of it!

That is all for now folks. Feedback, or your own ruminations, in the comments or at sp@sajithpai.com (Please don’t send pitches or CVs or anything work-related at my personal id; I won’t respond to them).

Regular readers know that this newsletter has two permanent sections:

• Writings - where I usually write and / or refer to one or more original pieces that I published in the previous months, typically about venture or the startup ecosystem.

• Readings - about what I read and learnt about. My reading diet is tilted rather heavily in favour of books and podcast transcripts, and against articles / newsletters. This will naturally reflect in the reading list.

This is a long newsletter - think of it as akin to a monthly magazine from me (only the frequency may not be monthly!). I don’t know if you can read this entire newsletter (and peruse the links) in one sitting, and even if you do a second run ( which I very much doubt), you will have to pick and choose what to focus on. A good way to read this newsletter is to certainly read my original writing(s) below, and then glance through the rest and pick 1-2-3 items that pique your interest. Anything more is a bonus!

Writings

I had a busy last month, finally releasing the first two chapters of a practical handbook for founders to iterate to Product Market Fit. The two chapters are collected here at this microsite.

Since then I have been taking it easy, relatively:) Still, here is what I published in the last three weeks since the last newsletter.

1/ PMF Convo #20 with Rajan Bajaj of slice

This was an old convo I had with Rajan over a couple of years ago. For various reasons we couldn’t publish it then, but finally decided now was the time (following a fun twitter exchange). In the convo, Rajan shares his perspective on PMF (he has a definition of PMF as product love or PPF = product to problem fit, a classic approach that many product-focused founders have), the metrics they use at slice, the journey and pivots etc. Link to the PMF Convo transcript.

2/ The PMF X-Ray Framework

The PMF X-Ray framework is a structured way to understand the choices and tradeoffs startups took along the route to achieving (or not achieving) PMF. Here is an introduction to the framework along with examples of the PMF X-Ray applied to Indian fintech unicorn Razorpay, and U.S. restaurant tech unicorn Owner.com. Link to the essay introducing the framework, though the formatting is better here in this Google Docs file.

Subscribe now

Readings

Books

1/ Affairs - Juliet Rosenfeld

A practicing (Freudian) psychoanalyst looks at five extramarital affairs and the pleasure and pain they evoke, analysing them through the prism of Freud's theories. I don't know how much of the theory is 'scientifically' validated but the portraits of these five affairs, and the impact it leaves behind on the protagonist as well as their partners is fascinating and horrifying all at once. Good read though.

2/ OTP Please! - Vandana Vasudevan

Business anthropology done right. The book, written by a friend, takes a look at the landscape of the gig economy, and covers the perspectives of the key actors such as the aggregators, sellers, buyers, and the gigworkers, humanizing them through severa stories and anecdotes. And that makes for a very rich and nuanced portrait of gigworker precarity, buyer privilege, and platform power.

3/ Supreme Whispers - Abhinav Chandrachud

American Professor George Gadbois Jr was a keen observer of the Indian Supreme Court, eventually publishing two books and several papers on the Supreme Court of India. This book by Abhinav Chandrachud is based on 116 interviews that Gadbois conducted with more than 66 judges of the Supreme Court of India through the 1980s. Reviewing the interview notes that Gadbois shared with him, Chandrachud reflects on these through the prism of key themes such as inter-judge rivalries, how nature of judicial dissent, how judges are selected, how politics has influenced that selection, and in one illuminating yet infuriating chapter covers the rise of the Special Leave Petition, a unique legal construct that Supreme Court itself has encouraged and which now takes up two days of their time, reducing time for reviewing cases.

Podcasts

1/ The Sushi documentary that is actually a philosophy lesson

David Senra on Jiro Ono on the Colossus Founders

'Jiro Dreams of Sushi' is one of my favourite movies. On the surface, it is about a food documentary about a 85-yr old sushi chef and his award-winning restaurant. But like all great art, it transcends itself. It is not a food documentary as much as a portrait of an artist and his continual search for perfection. Jiro's philosophy is something that inspires me and his life philosophy is something I keep in mind continually. So, I loved this episode where David Senra does his take on Jiro's Sushi restaurant, and what it teaches him about craft and striving for perfection. So many quotes that inspire me to be better at my craft, and deeply move me here.

Jiro: "Once you decide on your occupation, you must immerse yourself in your work. You have to fall in love with your work. You must dedicate your life to mastering your skill. That is the secret of success and is the key to being regarded honorably."

Jiro: "All I want to do is make better sushi. I do the same thing over and over, improving bit by bit. There is always a yearning to achieve more. I'll continue to climb, trying to reach the top, but no one knows where the top is. Even at my age, after decades of work, I do not think I have achieved perfection. But I feel ecstatic all day. I love making sushi. That is the spirit of the shokunin. I have never once hated this job. I fell in love with my work and gave my life to it. Even though I'm 85 years old, I don't feel like retiring. That's how I feel."

Senra: Another part of being a shokunin is you have to pass what you know on to the next generation. And in this case, it's through decades of apprenticeship. So it says, when you work for Jiro, who teaches you for free, but you have to endure 10 years of training. If you persevere for 10 years, you will acquire the skills to be recognized as a first-rate chef. When you first sit down as a customer at Jiro's, they give you a hot towel. Well, those towels are prepared by hand. So an apprentice must first be able to properly hand squeeze a towel. At first, the towels are so hot that they burn the apprentice's hand. And this part was fascinating. It is a very painful training, which is very Japanese. Until you can adequately squeeze a towel, they won't let you touch the fish. Then you learn to cut and prepare the fish. After about 10 years, they let you cook the eggs. And so one of the apprentices, they interview one of Jiro's apprentices and he talks about the fact that they were trying to teach him how to make egg sushi. And it was just iteration after iteration after iteration. They would just reject it over and over again. He says, "I made over 200. Every single one was rejected. When I finally did make a good one, Jiro said, 'Now, this is how it should be done.'"

Excerpts from the podcast episode I found interesting here. Too many though!

2/ The hierarchy of employee and customer needs

Chip Conley on the Lenny Rachitsky podcast

Chip Conley, ex hospitality founder, Airbnb operator (joined in his 50s), author, and now founder of the Modern Elder Academy, had an interesting episode with Lenny, covering ageism in tech, how to be a high productivity and well-accepted operator in your 40s and 50s in tech, the hierarchy of compensation -> recognition -> meaning as what the employee needs in their role, and detailing the philosophy behind the Modern Elder Academy. Good one for anyone in their 40s or 50s like me!

Chip: “So, you know, Maslow's hierarchy, basically five levels later in life, he had a six, seven and an eight level model, but you know, uh, at the base is your physical, uh, you know, the kind of physical water, food, air, and you move up to self actualization at the top.

So to use this model as a hierarchy of needs for employees, customers, and investors is what the peak model is about, the peak, my book. The employee model is really simple. It's money or compensation at the base. recognition in the middle and meaning at the top.

Now, there are some industries and some kinds of jobs in which money is 90% of the pyramid. So just because it's at the base doesn't mean it's not the dominant part of the pyramid. But the differentiation often is in recognition and meaning. In nonprofits, usually the money piece of it's rather thin and the recognition is this and meaning is huge. So understanding how do you create an organization?

And I gave a TED talk in 2010 about this topic as well. How do you measure the intangibles of meaning? And how do you create an environment where people feel a sense of meaning?

The customer pyramid, briefly, I'll just say that one, is meeting expectations is the base, meeting desires is in the middle, and then meeting unrecognized needs. And I think one of the things that we did at Airbnb about a year after I joined and when Jonathan Mildenhall was joining is we really tried to ask ourselves, are we in the home sharing business or are we in some kind of business that is even bigger and broader than that? And ultimately, we came up with the idea that we were in the belong anywhere business. Airbnb was not in home sharing. We were in belonging anywhere.

Once you have that down, that was sort of the unrecognized need at the top of the pyramid. Then that becomes an organizing principle for how do you teach your hosts to create a sense of belonging? How does our marketing and advertising play up the belonging piece, especially, and the everywhere piece?

Because hotels are not everywhere, but homes are. And so I would just say that, you know, this model, the idea of hierarchies is I think very helpful. And yeah, my book Peak has been out for 18 years, but I still have asked to give 20 or 30 speeches a year on it.

Lenny: Oh, man. This pyramid of comp recognition meaning is really interesting, especially these days, because with all this AI researcher poaching, there's all this talk of just like, will people just go work wherever they get the most money? Or is there a mission and meaning to the work they're doing that will keep them not taking a $100 million offer? And it seems to be happening in a lot of cases, which shows you the power of meaning.”

Excerpts from the episode I found interesting here.

3/ The six levels of wealth

Nick Maggiuli, author of The Wealth Ladder, on Infinite Loops podcast with Jim O’Shaughnessy

Nick Maggiuli categories U.S. households into six levels

Here are the six levels (data for US)

Why the wide ranges?

Nick: “I came up with this because I was like, hey, I realized that like small amounts of money don't really change people's lives as they gain wealth. Like once you have a million bucks, an extra 10,000 is not going to change your life at all. Like, you can do one nice thing with it, that's it. But your lifestyle is the same. To really change your lifestyle, you need like a logarithmic, a 10x jump to get there”

An interesting point Nick makes is about Level 4.

Nick: “But level four is what I call the no man's land of like wealth building. Because the things that get you into level four are very different than the things that get you out of level four and into level four five, right. Like you can have a good salary, save money, invest, etc, you'll get into level four, 1 to 10 million, right. … But to get to level 5, 10 million plus, I think it fundamentally takes a different path …. And that usually means creating your own business and selling it or starting a startup early where you get enough equity and then that startup sells for a ton of money, right?...So, you know, going from level four, that's like a good professional making 200k a year (income). Like, that's your typical, like, solid, you know, managerial profession. That's how you get to 1 to 10 million. But to get to level 5, you need an income of $724,000 a year. And it's very difficult to get there in corporate America unless you are a business owner and you have equity or have something that's paying you in addition to that, right?”

4/ How Revolut found a wedge into the market

Martin Mignot, Index Ventures, on the 20VC Podcast w Harry Stebbings

Glimpse into Index Ventures, a European-American fund that has seen some big wins of late (Wiz, Figma etc.) from the perch of Martin Mignot one of the partners. Useful for the venture nerd. This one passage on Revolut and how they found a wedge into a competitive market is a useful one for founders.

Martin: “But the reasons why I had a lot of conviction on Revolut was I came in with a prepared mind, meaning that I had been looking at the space for a little while, had looked at a company in the US called Simple.

And the main reason was people don't want to switch bank accounts. It's a pain. Why would you switch bank accounts? Oh, it's going to be on mobile. But like, well, my bank has a mobile app. Why do I care? And so I had met, you know, I looked at Simple. I had met Monzo as well, actually. And I was looking for a trigger, like what would convince people to switch bank accounts, which is such a pain.

And what I really loved with Revolut was a simple trigger with FX. They didn't sell people, oh, you're going to switch bank accounts. They sold, oh, you're traveling to Portugal for a stag weekend. You know, you're going to get fleeced by your bank. Why don't you get a Revolut card? And I thought that was such a clever insertion point. And then from that point, Nick's view was from the beginning was that he wanted to be the global money app for every product.

But the insertion point was, I thought was really effective. And that's how they managed to grow so quickly and organically for the longest time because they had this very clear value proposition that was a lot easier than saying, oh, you need to sign up with a new bank, which no one wants to do. I remember chatting to Antoine Lanel there and he was like, you know, we won in many respects because we offer snacks to start. So don't try and convince you for the main meal. Just have a little snack and come back for some more and more. And then suddenly you want the main meal.”

Excerpts from the podcast episode I found interesting.

5/ How Lightspeed Commerce increased pricing by 4x and found success!

Dax Dasilva, Lightspeed Commerce, on the PMF Show w Pablo Srugo

Enjoyed this podcast episode on how Lightspeed Commerce (not the fund but a Canadian retail SaaS co) found PMF. The problem or pick arose out of Dax Da Silva’s personal experience and hence was extremely sharp and rooted in a genuinely pressing usecase - the core audience was Mac Resellers, a community he intimately new. Product to Problem Fit or PPF was sharp and that eventually made PMF too easier. Good passage about how a conversation led him to understand that he was leaving a lot of value on the table, and led him to increase prices 4x, and that led to an unlock as well as created a generous margin profile that attracted resellers and helped him create a reseller-led motion, that powered the co to success.

Dax Dasilva: “Probably the most important part of this whole exercise was pricing. In those early days of Lightspeed, there was a couple of companies I really admired. Like there was not a lot of business software on the Mac, right? Like we were really creating a new category. There's an amazing CRM package that was for, like, more like an entrepreneur that was, like, on the road, and they were keeping their contacts and building their business. And we were different, right? Like that was a multi-user system, and so were we, but we were kind of like multi-user and running the whole operation. So, you know, they were charging $140. Okay, let's try to charge $170, you know, per user. And I showed this to my dad's business partner, one of my dad's colleagues that was interested in becoming a reseller of ours. And he was like, x4 (4 times). And I was like, x4. I'm like, where did you get that from? And he's like, first of all, if you try to buy a PC black plastic system out there, people are paying a ton of money. You're running the whole business. Don't look at what your competitor or what you think is somebody in your category is charging. You've got a x4. And he was thinking maybe it's a bit selfish for him because he was going to get.

Pablo Srugo: He's got to get margin. Yeah, yeah. Which is the lesson in itself because If you don't have that, then you don't have resellers, which is a whole other.

Dax Dasilva: And that's like the second part of the story. That, x4. When I flowed that through a three-year spreadsheet, and it showed. The ability for the company to actually fund more developers, more salespeople, we would not be here today if we didn't times four. There's just no way. That allowed us to build the software that ended up being adopted by all of those users on a large level. And if we had kept the software cheap and had the same number, of nothing would have added up. We would not have been able to expand and scale the company. So that was a huge, huge important lesson. But of course, you've got to have that product market fit where people need the solution. They can't run their business. They have to have it. And then that's where you have. The ability to do times four, because they're thinking, okay, I'm going to pay this, but I know a lot of other people are paying this too. I'm thinking of, like, as one of the Mac dealers at the time, they were taking a bet on my one-year-old company. They're like, okay, if everybody's paying five grand for this, and we're also paying an annual maintenance fee. Then this person has real money to build something real for my needs. And so it also gives them comfort that, okay, if I'm paying the guy only $170 or a few hundred bucks per user, there's a bit more risk for me. This guy's not gonna be able to pull it off, or he's not gonna be able to do, build out a team. So it taught me a lot about the value, right? The value that you deliver with your software. And then ultimately, when they became, you know, after seven years of bootstrapping, because that was our journey. A seven year of bootstrapping, we got to $10 million of annual revenue, which was all software. All of that was driven by 400 resellers around the world, making 25% on times four pricing.”

6/ Venture humility as venture strategy

Greg Rosen, Box Group, on Uncapped Podcast w Jack Altman

Really interesting podcast, especially for the venture nerd, in how you can create a venture firm around a strategy of widening the top funnel for as many great companies as you can. If venture is a strong power law business, then you don't want to miss those 1-2 generational companies a year. Hence you need to see all the (potentially) great ones, and play as many as possible. And if you are in one of those then your stake size really doesn’t matter. And hence Box Group optimises for access more than anything - that is, getting into as many of these companies that they think can be large outcomes. To do so, with a finite fund size, it eschews any stake considerations, follows a philosophy of partnering with larger funds but never leading deals, and tries to invest as fast and with as low overhead as possible. Clever strategy. In that regard, this is as much a strategy podcast as it is about a venture fund.

Rosen: “...if you look at the math formula of venture, the like seeing, picking, and winning a deal, and then equals enterprise value output… and everyone says venture has gotten harder. I don't know how to be 50% better at picking, let alone 2X, let alone 10X. I just think it's like a fool's errand to think that you're magically going to become better pickers. And so for us, we've said, okay, venture has gotten harder; we don't know how to be better pickers. Let's take winning aside. We are going to be really focused on seeing how do we see more in order to counteract how much more difficult it is.”

…

“Josh Kopelman came on your podcast and talked about the venture arrogance score. I would say this is our like venture humility score, which is we don't know how to have a basket of 20 companies in, you know, a fund or, you know, in a year and pick the most important ones given how competitive and hard it is. So for us, we're saying we need to do more. We need to see more. We see on average about 5,000 to 6,000 qualified or referred opportunities a year. And then we at BoxGroup end up making about 70 to 80 investments a year. And like, that's our humility is like, if I could at the extreme make one investment and I would know that that investment would be OpenAI, of course I would do that. I'd have the best performing venture fund of all time. We don't know. And so we take more shots on goal because it's much harder so that we can counteract how much more difficult and competitive venture has become.”

Excerpts from the podcast episode I found interesting here.

7/ Vibes investing for a vibe coding world

Peter Fenton, Benchmark, on the Uncapped Podcast w Jack Altman

SPW: Nothing terribly new, but interesting nonetheless for the venture nerd, on how Darwinism applies to venture (he describes venture as operating in a nutrient-rich world without any selection pressures!), and how Benchmark’s distinctive early stage picking has navigated well to the AI world - vibes investing for a vibe coding world. This passage on how they intentionally didn’t look at HeyGen’s data room before investing was quite funny!

Peter: “Benchmark is completely ephemeral, like the line up is completely ephemeral, no names on the door. It is designed to be destroyed from within and reborn, but the mechanism is the same. The adaptive mechanism is all those things we talk about, core design principles, shared identity, there's clarity across all the partners in exactly what we're doing, fast and inclusive decision making, the idea that each of us is an owner gives us a sense of autonomy, another core design principle.

And there's not quality control and overhead and processes, and there's no memos. When someone shows us a data room, we tend to laugh. I'm like, oh god, I have an example.

This may come back and haunt us, but we invested in a company called HeyGen. Joshua said at the end of the process, he's like, well, we're talking to a lot of other firms, and they've all gone into the data room, and we want to cross this threshold with you. We feel this is the full potential partnership for us, but you haven't gone to our data room yet.

And, you know, our LPs may not like me saying this, but I said, there's nothing good that can come from that. It's like, because I'm going to go in there and ask a bunch of questions that undermine the commitment you're getting from us, which is to say that you, Joshua, at HeyGen, with Wayne and your team, are building a generational company, and that I've seen what I've seen from how you've talked about the product roadmap, how we've brainstormed about where you're going to go with the next set of releases, and whether or not you're retaining a learning and distance training user that isn't the long-term goal for the business doesn't help me. And I think that value proposition is different to entrepreneurs, and it's somewhat, it's not a reiection of these other models.”

Excerpts from the podcast episode I found interesting here.

Other podcasts I enjoyed

Graham Duncan on the Village Global podcast w Ben Casnocha talks about reference calls / checks and how to do them well. I have the same view and now try to do as many blind refchecks in advance of an interview. Though I don’t know how he can pull off an hour long reference call but I guess his reputation helps I guess.

Military Historian Sarah Paine’s lectures, getting released on the Dwarkesh Podcast are riveting. The first of the six-part series that was released is on how Japan became a dominant power in the Far East defeating China (1890s and 1930s) and Russia (the famous 1904-05 war). The second, on Germany vs UK, and more broadly WW2, was published as I was writing this.

Historian Srinath Raghavan’s interview (not a podcast strictly) with Rohan Venkat in the context of his biography of Indira Gandhi has a good explanation of the structural forces in the Indian political and legal system that led to the Emergency. Illuminating read.

The latest episode of the Blume Podcast features Razorpay founders talking about their 0 to 1 journey. Really enjoyable listen (of course I am conflicted!) and notable that the host and guests all were IIT Roorkee alums. Link to podcast + transcript; excerpts I found interesting here.

Articles

1/ Reverse Demo or solving a customer problem in your product demo

The GTM Inflection Points That Powered Clay to a $1B+ Valuation by First Round Review

Salestech co Clay started as a horizontal productivity tool a la Airtable and meandered for a while but it was only when they decided to focus sharply on an “incredibly narrow wedge — data enrichment for cold email agencies” that they saw Product to Problem Fit and then eventually PMF happen. This is an illustration of the challenges SISP (Solution in Search of a Problem, a YC term) products face. They are hesitant to identify a clear problem + persona coupling to go after, thinking that they will reduce their TAM if they do so. But it is only when they get specific and narrow their usecase, that they see a tight Product to Problem Fit (or the first part of PMF) emerge, making eventual PMF easier. This article describes what happened after they decided to narrow their product offering, and how they hit on a GTM motion (initially PLG then enterprise) to grow revenues.

This passage on their reverse demos was interesting to read. More founders should use this.

“As Clay started chumming up more interest from agency owners, Anand and Nowoslawski were constantly hopping on the phone to show them the product — usually powering through at least eight of these calls a day. But this was no ordinary product demo. Here’s how Clay’s “reverse demo” flow worked:

“Let’s say you signed up for the waitlist. I would review the list in Clay every morning, and if you fit our ICP I would trigger an email that said, ‘Hey, book some time with me and come prepared for this conversation with a dataset you want enriched or a problem that you wanted solved in this 30-minute slot,’” says Anand.

If they showed up empty-handed, for the first five minutes of the call Anand and the potential customer would come up with a personalized use Case. Here’s where, if this was an ordinary demo flow, you might expect Anand to take over the steering wheel and walk them through the product and the key features with a canned script. But instead, Anand acted more like a GPS, with the customer’s hands still firmly planted on the wheel. If you’re learning how to drive a car, you don’t sit in the passenger seat while the instructor lectures you. You take the wheel while the instructor safely guides you. The customer would share their screen, Anand would give them a Clay signup link, and then use Zoom’s annotation features to guide them through which buttons to click to help solve the problem at hand.

Our goal with every reverse demo was simple: Solve the customer’s stated problem within 30 minutes — and try to blow their minds in the process.

This reverse demo structure worked for a few key reasons:

• Customers gained the confidence to come back. “Now they were equipped to do all sorts of other things in Clay. In the beginning, we had to do probably seven demos to convince someone to pay us $200-300 a month. But eventually, we got it down to one call or even none.”

• He got a UX masterclass. “I got to see up close what was wrong with the product because I was seeing exactly where new users were going wrong and I could pass that feedback along to Eric Engoron and other engineers to fix.”

• New ideas unlocked. “Occasionally someone would have an idea for a use case that we would immediately act on that would unlock the next stepping stone,” says Anand.

Instead of running a scripted demo, imagine the insane amount of feedback you get seeing how new users interact with your product. Imagine how 8 calls a day compound over 7 months.”

2/ Dan Wang on reading better

Breakneck: China's Quest to Engineer the Future by Dan Wang

Dan Wang, a technology analyst based in China, became popular for his long annual letters giving a peek into China. He recently published Breakneck, a book about China which is now well-known for comparing China’s engineering state with USA’s lawyerly society. The below is from a recent essay of his about the book, and the process of writing it. It is a fun read, and the following two passages stood out.

Dan Wang: “I became a better reader, too, over the course of bookwriting. I’ve learned to detect when writers attempt the difficult and when they succumb to laziness. There are parts of every book where writers cover a topic they have little interest in (out of some obligation), at which point I try to figure out how many pages I need to flip before getting to the parts they care about. I’ve learned to pay more attention to books in which authors say something in their acknowledgments. That doesn’t mean I like gushiness — rather, that tends to be a negative signal. A good acknowledgment is a sign that an author has put some care into their book.”

…

Dan Wang: “Working with the publishing industry has also made me more discerning about which books to read generally. Before I do anything to a book, I take a look to see if it’s from an academic press (like Yale or Oxford) or a trade press (like Norton or Penguin). It doesn’t determine anything. Rather, I am more alert to pitfalls. At a first approximation, academic books are written for the benefit of their authors, while trade books are written for the benefit of readers. There’s also a needle to be threaded between the former, whose failure mode is to deliver narrow arguments while bogged down with proving small points, and the latter, whose failure mode is to deliver small ideas in flamboyant prose, often packaged in bite-sized chapters. I look for books that manage to transcend the limitations of these categories.”

3/ When should you launch into a crowded market?

The untold story of Where is My Train's 100M users by Dharmesh Ba

India consumer observer Dharmesh Ba had a fascinating article about an app called Where Is My Train? (WIMT) That grew to 100m users and was acquired by Google in 2018 (its first product acquisition in India). WIMT is the canonical example of a made for India app that use ingenuity and engineering smarts to make it possible to track a train on the move without using the internet. How they did so is detailed in the article and makes it a must read.

I found the passage below instructive in terms of advising founders how to think about launching into a crowded market. It says you can launch into a crowded market if the products are not great and you believe that you have something special (and there is some validation from your beta users).

Dharmesh: “There were multiple train tracking apps before WIMT, why did you have to build another one?”

Nizam: “Everyone was subpar, actually. They were scraping NTES (National Train Enquiry System) data, scraping data from Indian Railways. They were just a shell holder of that same data. But at the end of the day, the problem is we need second-by-second updates of these trains, just like Uber. And that was not there with any of these apps.

The NTES is an official service provided by Indian Railways that offers real-time running information for trains across India. This includes updates on train schedules, live train status, estimated arrivals and departures at stations, delays, and train movements.

When you look at this public transport market itself, it looked like there was a lot of fragmentation and nobody was doing a great job at it. In India itself, there were 50-plus apps that show some demand in the market, but there is not a good app in that space. I have this philosophy: if an app in a category doesn't have a 4.6 or 4.7 rating with a huge number of downloads, that category is still not solved. You can go after it.”

4/ Social media is designed to make you forget time

How Social Media Shortens Your Life by Gurwinder Bhogal

Well-written post by Gurwinder on how social media is engineered for mindless scrolling. Lack of ‘UI right turns, and digital ‘curvilinear mazes’, like in casinos, he says, spur addictive scrolling leading you to lose track of time. Lots of interesting ideas and concepts explored in this piece through the lens of these themes; one concept that stood out was emplotment, i.e., how we construct information into stories to remember them better etc.

“Now here’s the issue: your social media feed resists emplotment because it’s the opposite of a story. It’s a chronological maze. It has no beginning, middle, or end, and each post is unrelated to the next, so that scrolling is like trying to read a book in a windstorm, the pages constantly flapping, abruptly switching the current scene with an unrelated one, so you can never connect the dots into a coherent and memorable narrative.

Thus, not only do you forget time while scrolling through posts, but you also forget the posts themselves. We have no problem recounting the plot of a good book we read or movie we saw last year, yet we can barely remember what we saw on social media yesterday.

For instance, when faced with a choice of experiences, choose the option that’s most likely to lead to a good story. Read books instead of scrolling social media feeds. Go on adventures instead of staying home. The more stories you experience, the richer your memory will be.”

5/ VC content as ‘power transfer technology’

I am joining A16Z by Alex Danco

Interesting hire by A16Z. Alex Danco wrote some interesting posts towards the latter part of the last decade but had gone AWOL post joining Shopify. He joins A16Z as Editor at Large, responsible for the written output of the firm. Some good ideas in this piece, most notably how VC content is ‘power transfer technology’ which helps founders draw on the VC’s power and legitimacy to create their own legitimacy. The other interesting idea is that there are two audiences for any content, a smaller primary audience that reads and interprets the writing and recasts or expresses it anew or simplifies it for the larger secondary audience, who may not ever read the original piece of writing but hear it from the primary audience. In that sense, the writing is jointly enabled by the writer + primary audience both.

“ ‘Power transfer technology’ is what the business of VC is. Why does a VC firm care about content? It can’t just be to advertise the firm; or promote their partners and their theses. Those are both consequences of success, but they can’t be the actual goal. The primary objective of a VC firm’s content, particularly their written output, should be to give founders power. The goal is to give them writing that transforms them into someone with more legitimacy, which is what power really is about.

…

I remember some days when I was a founder and no one would take me seriously, except for when I could produce a blog post from someone like Paul Graham or Semil Shah and speak to that idea. Something incredible would happen in those moments – people would actually listen to me, as if I’d suddenly become magic. Magic works because it is communication. The founder equipped with the VC’s writing should communicate something higher-signal than the founder alone. Ask, “what must be true of the content for this statement to become real?” and you’ve got a good guide for what kinds of things to write.

This relationship between VC and founder scales all the way up to real power-politics: the job of the VC firm is to be the “legitimacy bank” where founders (and other high-agency people) can go to take out legitimacy on credit, or make a legitimacy deposit. I find this to be a wonderful way to frame the founder-VC relationship because it does NOT imply the VCs are the “grownups” in some patronizing sense: it celebrates legitimacy as a thing that VCs and founders incept together, just like how blogging is thing that the writers and their primary readers incept together.

This is why VC blogs were such a good product in their heyday. As the “free tier” of the VC, it naturally frames the relationship as one where legitimacy is jointly incepted (by the writer and primary reader), not as one that’s benevolently bestowed.”

6/ How to pick your dream job

Face it: you're a crazy person by Adam Mastroianni

Fun essay on how you should try to unpack the daily routine in any job and then determine if this is really what you want to spend the next few or rest of your lives doing. For instance running a coffee store is really selling hot bean water; being a YouTube creator is releasing a video regularly, and formatting your life to enable the same, such as on days you are unwell too.

“I meet a lot of people who don’t like their jobs, and when I ask them what they’d rather do instead, about 75% say something like, “Oh, I dunno, I’d really love to run a little coffee shop.” If I’m feeling mischievous that day, I ask them one question: “Where would you get the coffee beans?”

If that’s a stumper, here are some followups:

• Which kind of coffee mug is best?

• How much does a La Marzocco espresso machine cost?

• Would you bake your blueberry muffins in-house or would you buy them from a third party?

• What software do you want to use for your point-of-sale system? What about for scheduling shifts?

• What do you do when your assistant manager calls you at 6am and says they can’t come into work because they have diarrhea?

The point of the Coffee Beans Procedure is this: if you can’t answer those questions, if you don’t even find them interesting, then you should not open a coffee shop, because this is how you will spend your days as a cafe owner. You will not be sitting droopy-lidded in an easy chair, sipping a latte and greeting your regulars as you page through Anna Karenina. You will be running a small business that sells hot bean water.”

To do well in any job you have to endure or even love the dreary aspects of the job. Someone who is exceptional in the job is someone who finds it easy to do the dreary part of the job well – for instance preparing the same dish twice a day every day for the next five or so years for a chef – because it matches a certain unique capability or ‘craziness’ that they possess. All of us have certain eccentricities / craziness, obsessions or unique capabilities in certain areas that help us do something easily or endure something that the other won’t. You need to match the unpacked tasks with what your crazies are, to find the job that you love, the one which is play for you but work for others.

Pair this essay with ‘The Mundanity of Excellence’ in which they found that elite swimmers were able to put in crazy long hours of practice (and thus outshine the others on competition day) because they rather enjoyed the tough practice sessions. They had the right kind of ‘crazies’ that would help them endure or even made it enjoyable to tolerate those punishing hours of practice.

7/ Kerala as a simulacra (copy of an original that doesn’t exist)

Param Sundari and the unbearable lightness of being Malayali (may be paywalled)

Journalist MK Nidheesh wrote a fascinating article on how the Hindi movie Param Sundari’s caricature of Kerala, and the resultant outrage from Kerala media / social media exposes two themes. One, he says it reveals the position that Kerala occupies in the Indian heartland - the easy exotic, all nuance flattened out for easier consumption. Second, he hints at the tension between the greater visibility of symbols of Kerala’s culture, and the simultaneous disconnect of non-Keralites and even the locals from the complexity and nuances of the language, as well as the messiness of life as it is lived in Kerala. He says Kerala seems to now exist in our minds, or we experience it rather as a series of social media tropes.

“Where did the filmmakers get their idea of Kerala, that they thought audiences would recognise? More importantly, why Kerala at all? They could have set their cross-cultural romance in any place metropolitan audiences treat as distant and picturesque. The choice suggests that Kerala occupies a peculiar position in today’s national imagination. Kerala is not simply exotic, but familiar enough to be instantly recognisable, yet distant enough to be flattened without consequence. In other words, Kerala can be consumed without being known. It is an irresistible quality to an industry like Bollywood that deals in shorthand.

But perhaps unknown even to the makers, what Param Sundari has done, unwittingly, is to crystallise a cultural anxiety that has been building for years: the sense that Malayali identity, once dense with historical weight and political consciousness, has been progressively hollowed out into a series of consumable gestures.

…

French theorist Jean Baudrillard is long dead; otherwise, he would have described this as simulacra: copies without originals, references that circle back only to other references. This is the paradox that defines contemporary Malayali existence now: unprecedented visibility coupled with ontological weightlessness.”

Other articles I enjoyed

The Man With the Hot Hand - Colossus. This piece on Ramtin Naimi of VC fund Abstract was a fun read. It is a companion post to the podcast which I covered in my last Interleavings (17 August ‘25). It is a good depiction of how to think intentionally about positioning your fund in the VC landscape.

Wispr Flow’s pivot from hardware to software and how it became one of Silicon Valley’s fave apps. AI trends observer and investor Deedy Das: “This is the one AI app I use everyday even more than ChatGPT.” This piece is from the PMF /evals newsletter written by Astha at Chargebee. I love the newsletter - it covers what it means to hit PMF in the AI era. Clever theme, covering examples of AI-native products that have succeeded and what helped them get to PMF and success.

Restaurant-tech startup Owner.com’s path to PMF in the First Round Review was an instructive read on listening deeply to customer’s and iterating ruthlessly to meet their needs. Some fascinating inputs into how to build for SMB - do not customise the product, and do note that many SMBs buy the product for emotional needs as much, to show the world that they use advanced tech products. I captured learnings from the essay in my PMF X-Ray of Owner.com.

This deep dive into soon to IPO startup Urban Company was a good read. The piece by public market investor Paavan Gami analyses its business model, and makes the case that it has pretty much tapped out its TAM. The article also shares some tweaks to its biz model such as setting up offline beauty salons to reduce travel time, and grab a larger share of more complex treatments which cannot be done at home.

Bye!

It is time to wrap this! As I shared earlier, you should think of this substack as akin to a monthly magazine - you don’t have to read it all in one sitting, and you don’t have to read all of it!

That is all for now folks. Feedback, or your own ruminations, in the comments or at sp@sajithpai.com (Please don’t send pitches or CVs or anything work-related at my personal id; I won’t respond to them).

Regular readers know that this newsletter has two permanent sections:

• Writings - where I usually write and / or refer to one or more original pieces that I published in the previous months, typically about venture or the startup ecosystem.

• Readings - about what I read and learnt about. My reading diet is tilted rather heavily in favour of books and podcast transcripts, and against articles / newsletters. This will naturally reflect in the reading list.

This is a long newsletter - think of it as akin to a monthly magazine from me (only the frequency may not be monthly!). I don’t know if you can read this entire newsletter (and peruse the links) in one sitting, and even if you do a second run ( which I very much doubt), you will have to pick and choose what to focus on. A good way to read this newsletter is to certainly read my original writing(s) below, and then glance through the rest and pick 1-2-3 items that pique your interest. Anything more is a bonus!

Writings

August saw me publish two long pieces, Understanding PMF (13k words), and The Pick (20k words), which respectively constitute Chapters 1 and 2 of my book on PMF. They are housed in this microsite.

Unlike the traditional book publishing route, where you get a 200-300 page printed book published by a Penguin or Harper Collins, I am publishing ut as an online series, with each chapter distributed freely on the interwebs whenever I finish one. At some point when I release the last chapter, I will collect all of the chapters and publish them as an ebook (and maybe a printed book) titled The PMF Playbook.

I have got some wonderful responses to the two chapters. Sharing some of them below.

This was the most intriguing one, where a founder fed my essay into an LLM along with his startup’s metrics to check where they are on the PMF path.

As a writer, you have to make peace with the fact that your work is going to be interpreted through AI. We are writing for AI more than humans. Many readers are mostly reading the summary generated by AI, especially when it is a long piece like mine.

That said there are some folks who read the essay word by word, having printed it out. Here is a pic I received from one such reader.

When I was spending those nights writing the chapters, i promised myself I would be satisfied so long as it helped at least 1 founder. Happy that milestone is crossed.

My third piece in August was a repurposing of a section in ‘The Pick’ (Chapter 2), on picking your cofounder. It was published as Solo founders are battling Silicon Valley’s biggest bias (3k words), and looks at the persistent bias that Valley VCs have against solo founders. It covers how solo founders can defray the obvious risks and disadvantages of not having a cofounder, and also details how you can pick a cofounder through organic or via founder matching platforms / incubators.

Readings

Podcasts

Yes, Podcasts under Readings because I read transcripts of podcasts, and not watch or listen:)

1/ How to strategically position a venture firm in a crowded landscape #1

Nakul Mandan, Audacious Ventures, on Venture Unlocked w Samir Kaji

I thought it was an excellent episode for us venture nerds. Any one who finds the craft of venture (or even strategy in general) will find this podcast interesting, given it covers how a GP Nakul Mandan, thought through design / strategic choices to position Audacious Ventures in the crowded seed landscape. One of those rare podcasts that will appeal / be useful to both ambitious young VCs obsessed with venture craft as well as senior VCs looking to start their own funds:)

Specifically, I really liked how they decided to use talent / recruiting as a key strategic lever, and how they effectuate (such an ugly word I know!) it by giving their head of talent, Samantha Price, a seat at the high table, and, not having bonuses for the talent team (they don't want recruiters to push candidates down founders' throats, and misalign incentives). The other point I liked was Nakul’s clarity around why he wants to pursue a platform / 'machine' approach as opposed to an artisanal approach. 

Recommended for a rare view into how an emerging GP crafts a strategy for his firm. White spaces are few and far between in venture today, so it is fascinating to see Audacious hit upon one. Venture has looong feedback loops so it will take time for us to know if their strategy was successful, but I felt it has the potential for success given the thought and craft given to it.

Nakul: “VCs, the large, the branded firms that we all admire, Lightspeed, Sequoia, all of these, became too large to service the seed stage entrepreneurs.  I've talked to a lot of seed stage managers on this, and we talked about the big firms. The reality of their business models are fundamentally different. When you're raising a billion, 2 billion, 5 billion, even $8 billion, at the end of the day,  your job is to put as much money in very clear consensus companies. Series A, Series B, Series C, Series D. If you do seed checks, it's typically for option value versus anything else. And one of the things that a lot of seed stage funds sell against is, well, if you work with big fund X and they put in a million dollars, 2 million out of a billion dollar fund, they're not going to pay attention. You're not going to get the senior partner. With us, you get the senior partner. I have one person. I do everything. I'm your first call.

So as crowded as the VC market is, the one gap in the VC market that I saw was that there's no gold standard VC or seed stage firm. Other than First Round Capital, there's no platform firm at seed. First Round has the brand cachet and rightly so of being the sequoia of seed. But after that, there's a steep drop in seed firms. …Chemistry, all of these want to start series A firms. So true GPs don't ever start seed firms. So the first gap I saw was that there's an opportunity to build a gold standard seed firm. Which people like me can do and I've been trained to do, but people like me don't do it.

The second gap I saw was, which is more fun, actually is, okay, if we do want to build a platform firm, what is it going to be our value proposition beyond advice? For me, as I thought a lot about it, it came down to where we can create the maximum impact is building an exceptional team around the founder. And I can go in a lot of depth around it. So our first employee after me was our talent partner alongside MZ, my investment partner. And half of our team today is recruiters. So we focus on two jobs at Audacious. Invest in force of nature founders, help them recruit an amazing team. Then we get out of the way.”

Link to excerpts from the podcast episode I found interesting.

2/ How to strategically position a venture firm in a crowded landscape #2

Ramtin Naimi, Abstract, on Colossus Invest Like The Best w Patrick O’Shaughnessy

Like the above episode, this one too is a great venture strategy case study. Easily one of the best podcast episodes I have encountered in recent times. There are two parts to the episode. The first is a long but utterly fascinating dip into his art collecting journey, his art collecting / investing philosophy, the mechanics and landscape of collecting, and the parallels with venture. This alone would have made it a good podcast. 

The next part, which covers the journey of Abstract, his venture investment firm, and their distinctive approach, combined with the first part, makes it a great episode. In the second part, what stood out was the strategy they adopted to carve a niche for themselves, 1) as an investment partner to multistage funds, figuring out the kind of founders they liked, and coinvesting with them. They slowly evolved out of that to become a fund that now leads, but that strategy got them established. 2) supporting founders on fundraising and becoming exceptional at it, so much that other coinvestors too defer this part - fundraising for the next round - to them. It is a good case study on how a venture fund figured out a clever strategy to win a successful position in the venture landscape (Audacious Ventures above is another good example of this). 

Ramtin: “The thesis in which I started Abstract was trying to identify which companies have the highest likelihood of becoming power law companies. And I identified power law by any companies that either had a private market cap or exited north of a 5 billion valuation.

What I'd realized over time was that if you eliminate Uber and Roblox from the equation—whose seed rounds were led by First Round Capital—it's close to impossible to identify power law companies in which the seed round was led by a seed-stage venture capital firm. This has changed in recent years, which is why our strategy has also evolved. But the thesis in which it was built off stayed constant.

And that multi-stage tier-1 VC firms are better at seed investing than seed funds are. And it's not to say that they'll outperform them because I don't think the portfolio construction model allows for that anymore at the scale of those funds. But I do believe that the power law companies of the future will be more likely to have seed financings led by multi-stage venture capital firms and seed-stage venture capital firms.

And in the early days, people didn't think multi-stage firms did much seed investing. But if you look at Sequoia, they led the seed round for Stripe, Airbnb, Dropbox and Nubank, and Andreessen led the first institutional rounds for Okta, Databricks and Slack, and Coatue led the seed round for Instacart and DoorDash, and Index led the seed round for Robinhood and Figma, and Lightspeed led the seed round for Snap and I think AppDynamics. And the list goes on and on.

What became obvious to me was that seed funds that claimed they had proprietary deal flow were mostly kidding themselves. They're a little delusional. And it's hard to believe that a seed firm that has two or three people have more coverage at early stage than a multi-stage fund that has 30 or 40 people.

And then it became very apparent to me that when a multi-stage fund and a seed fund tried to compete with one another, it was very hard for a seed-stage venture capital firm to compete with a multi-stage venture capital firm. Oftentimes multi-stage venture capital firms had brand weight the seed funds can't compete with, but more often than not it was the fact they're willing to offer valuation terms that a seed fund couldn't compete with. And I decided to build a seed-stage venture capital business initially aligning my interests with multi-stage funds as opposed to aligning my interest with seed funds.”

Link to excerpts from the podcast episode I found interesting.

3/ Too many aspiring founders are playing Silicon Valley status games

Edwin Chen, Surge AI, on 20VC Podcast w Harry Stebbings

SurgeAI is not talked about as much as ScaleAI (where Meta recently acquired a 49% stake, and hired its founder), but it seems like it is the better, bigger, bootstrapped version. They are at $1b revenue, all bootstrapped, and profitable, vs rival ScaleAI’s $870m rev with $1.6b funding (pre the Meta investment). They are well-regarded for their higher quality data, through better vetting and monitoring of its data labelling contractors.

In the podcast episode, Edwin talks about his philosophy of building - smaller high quality teams aligned to customer problems, being able to work at the insane pace that your customer wants, avoiding playing Silicon Valley status games like increasing engineering headcount or fundraising for the sake of it etc. The podcast also covers how he started SurgeAI - from the personal pain, and experience of having suffered from poor quality data, and the importance of the early customers in shaping your product.

SurgeAI is a textbook example of an ideal pick (of the problem space / startup idea) meeting all the three sub-criteria of a pick: why you / founder-market fit, why now / timing, and why this / large attackable market. Very rarely do you see someone who got all three right - Edwin had worked at places like Twitter, Meta and had seen the challenges of poor data and was able to build to address that, and benefited from the rise of GenAI, both timing and its emergence into a large market.

Edwin: “So I think one of the things that's always driven me crazy about Silicon Valley is that it really is just a status game for most people. People are just raising for the sake of raising. Their goal isn't to build some great product that solves an idea that they fundamentally believe in. Their goal really is to tell all their friends that they raised $10 million and they get a head buy on TechCrunch. I have a lot of friends who have worked at Google for 10 years. When you think about starting a company, they actually often tell me they don't even have a problem that they want to solve.

They're kind of just bored and they want to try something new. And at the same time, they can actually definitely pay their own salaries for a couple of months. But the first thing they tell me is, yeah, they're going to go out and raise some money. And so they might try talking to some users and they might try building an MVP. But the only reason they do that is just to check off some checkbox on a YC application. And then what happens is they will just constantly pivot around random ideas until they get something that happens to get a little bit of traction and that sounds impressive to VCs.

And so they spend all their time tweeting and tweeting hot takes and networking and going to all these VC dinners. And it's all just so they can get this highline about raising $10 million. I really think that people's first instinct should instead be to find some big idea that they fundamentally believe in that could change the world. And I don't really care why they believe in it. It could be because they have a lot of experience in the space. It could be because they talk to a bunch of users.

But it really has to be something that they believe in that they'd double down on for the next few years. Like if you think about startups, startups are all about big risks, right? You have to believe in something enough that you're going to take a risk building it. If all you're doing is jumping around from idea to idea every week until you land on something that gets you a thousand retweets, you're not taking any risks. You're just somebody looking to make a quick buck.”

Link to excerpts from the podcast episode I found interesting.

4/ Are Search funds the next big private asset class after venture capital?

Will Thorndike, on the Joy of Compounding podcast with Rick Buhrman, Paul Buser

Will Thorndike wrote the book ‘The Outsiders’ which was praised by Warren Buffett as an outstanding book about CEOs who excelled at capital allocation’, and was one of the pioneers of Search funds, where you raise a capital pool to acquire and operate a business (could even be small mom and pop stores) and reinvest those profits to buy more such businesses. Think of them as a ‘permanent vehicle for inorganic acquisitions’. This podcast has a lot of colour on these vehicles and the key personalities behind them like Stanford Professor Irv Grousbeck. I see some similarities between Search funds today and venture capital in the ‘80s (see below). They could be the next big asset class as a large number of boomers retire in the US / West, and look to someone to sell to.

“Rick: This reminds me of a lot of the ways in which I heard private equity and venture capital being talked about 15, 20 years ago—this sort of bygone era of cottage industry and really an asset class in the midst of formation. And, I mean, if we were going to take that point of view—that Search funds, in effect, are different enough to be described as a new asset class—why aren't more investors doing it? I mean, what are the barriers to entry? Because we've seen the data. Most investors chase performance, and secrets get out of a new area.”

Will: I think it's still growing. I think it's going to continue to grow. You are seeing an evolution in the asset class, and I think it's fair to use that term. In the last, again, 15 years, you've seen the rise of funds that are focused on investing in Search funds. That, I think, is a very natural reaction. The reality is, getting into search funds is a hard thing to do. You have to find your way into these networks, generally around business schools, and get access through them to graduating students. The people who typically raise Search funds are often right out of business school to within five years out of business school. They often come out of very specific networks in those schools. Certain professors—very specific professors—tend to teach the courses they tend to take. So it's not easy from a standing start to just step into that flow of transactions. So investing through funds is rational for an individual investor interested in accessing search or ETA; that's a rational thing to do. And the funds have grown.”

Link to excerpts from the podcast episode I found interesting.

5/ “Good writing is about triaging badly”

Alain de Botton on How I Write w David Perell

I really enjoyed this podcast episode where Alain de Botton, a hard to pigeonhole writer whose writing covers a gamut of topics from romance to philosophy, shares his views on writing. Covers topics such as his influences (Milan Kundera, Marcel Proust), to why good writing is borne of loneliness and suffering (see the passage below about Van Gogh and Irises; that gave me goosebumps), how the best writers triage badly, i.e., observe something that normal people ignore, and why (and how) he is writing 22 books at a time.

Alain de Botton: “Talk to anyone over 30, anyone over 40, definitely anyone over 50. You're going to find evidence of these incredible scars. It's from this that I think is born our receptivity to the arts. If you look at Van Gogh's Irises, the man was in pieces. The man was suffering like a religious saint. He was a very unhappy man. Poor thing, he was lonely, desperate, misunderstood, he ached for love. He was just so alone. 

Vincent van Gogh, one of the most famous people of the 19th century, was absolutely abject and desperate. When he looks at flowers, he's not just telling you about a flower. He's telling you about a flower seen through the lens of agony. When you look at beauty through the lens of agony, it becomes something slightly different; it becomes a life raft. The guy's not just painting a flower. He's painting a last reason to live, and in the end, he didn't make it. That's what lends the kind of poignancy. Some of the most beautiful things that humans have created have been born out of a kind of negotiation with something appalling.

…

Alain de Botton: It's almost as though there's some kind of triage system in our minds,

which has evolved over thousands of years, of what's important now. Our minds are very good at going, "This is what's important now," so I'm going to sacrifice other things. I'm not going to look at that.

This is what makes very old people or mad people or small children fascinating, but also maddening to talk to, is that they can't keep a coherent thread. If you say to a child, "What have you been doing in the garden?" they'll say, "I've been playing," and then they'll go, "Table." They forget because they see something else. They can't triage their thoughts.

Good art, a good artist, a good writer, is someone who's borrowing from the art of triaging badly. In other words, they are triaging not according to the standard sense of what's important, but according to a more diffuse, free-associative sense. They're going outside the normal bounds.

You mentioned David Foster Wallace. If you said, "David Foster Wallace, go on a cruise ship, what are you noticing?" he wouldn't go, "I'm noticing that the bar's here." He's alive to other resonances that are outside the normal purview, and that's what all writers do.

…

Alain de Botton: I wake up every morning, and I just think, right, what do I feel like writing about? I'm no longer thinking about books, weirdly. I'm thinking about pieces of prose that are around 800 words long, and I don't care what it's about. I just want it to feel like the thing that I most want to write that day.

I write in the early morning when I'm feeling like other people's agendas, etc., are not really on the horizon. So I'm coming from sleep. It's a protected personal space, and I just write what pleases me. Then I think I'll find a place for it; I'll find somewhere to slot it in because I've got about 22 books on the go now. I just think, oh, I'll put it there, or I'll put it there. One day it will belong somewhere. But it's written, as it were, from the heart.

I have totally given up the old way of working whereby I'm working on a book, and that means I just need to knit the next bit of the tapestry. I'm just going by feeling. I mean, sometimes, okay, I'm slightly exaggerating. Sometimes I have a sense of, like, it would be good to try and fill this bucket of thoughts around pictures. Okay, maybe drop them in that bucket. But on the whole, I'm trying to keep things fluid and feeling very authentic.”

Link to excerpts from the podcast episode I found interesting.

6/ Good non-fiction writing is first about clarity

Tamara Winter on the Dialectic podcast w Jackson Dahl

Charming podcast episode that is a celebration of ‘taste’, which is what Tamara Winter practices in her role as Commission Editor at Stripe Press. The episode covers a lot of good writing, and writers dwelling into topics such as what makes for good non-fiction (below), on how Jackson Dahl selects podcasts guests (“if I threw a dinner party with all the previous guests, would this person be a good add?”), how the sign of a great friendship is not that you can have long deep conversations as much as whether you can sit in silence for a long time. 

Jackson: “…What actually makes for good writing?

Tamara: I'll focus on the domain I know best: nonfiction. The best writing is first and foremost clear. To effectively communicate something, I have to know what you're saying. This often goes wrong when people read just enough to grok a particular writer's style and try to copy it. The writing becomes less interesting, or they use more complicated terms than necessary to explain something simple. The prose becomes overloaded because they think that's what makes for good writing. But the best writing, especially nonfiction, is fundamentally clear.

Second, a lot of the best writers have somebody in particular in mind, so they're not writing to the void. Sometimes that person is themselves. Brian Potter is a great example. When he's writing, he's answering a question that he has, and you get to come along for the ride. He's the kind of person who will spend days reading 500 sources just to answer the question. He doesn't sit down at a blank sheet of paper every Monday and ask, "What are we going to write about this week?" He just has these natural questions about the world.

Good writing doesn't over-explain. Stripe has a principle: speak up to the reader. You can trust that the person you're writing for doesn't need you to spell out the implications of every single argument. For one, that would make the piece too long. For another, you want to assume a certain competence on the part of your reader. If they are unfamiliar with something, they will just look it up and figure it out.”

Link to excerpts from the podcast episode I found interesting.

7/ What is AGI? Here is Dan Shipper’s definition.

Dan Shipper, Every, on the Lenny Rachitsky podcast

Every is an interesting organization. They started out as a content site, but have reinvented themselves as a curious content + tools co (Lex was spun out of Every) for the AI age. Dan Shipper, cofounder of Every. The other cofounder Nathan Baschez moved out to run the spin out Lex. Good podcast on how Every uses AI, why they have an AI Operations role, his definition of AGI, and why he likes Russian literature, and recommendations.

Dan Shipper: “With ChatGPT, you ask it a question and it returns a response and that's maybe slightly  better than a tab complete. And then now with Claude Opus 4 and Gemini and all that kind of stuff, also with deep research, it can go off and work for 20 or 30 minutes. So that leash is getting longer where you have to intervene.

I was thinking about this and it reminded me of Donald Winnicott, who was a child psychologist. He wrote this book called Playing & Reality, and his conceptualization for what it means to become an adult, what it means to go from being an infant to a child to an adult is when you're first born, you're effectively fused with usually your mother, your caregiver. There's no difference between you and her or you and whoever your caregiver is.

And growing up is this process of being gradually let down in certain moments where you can handle being let down. And raising a child is about knowing when they're ready to be let down a little bit and have to stand up on their own. So I think there's that same leash with human development. You get longer and longer periods of time where you can be on your own.

So we're still in the 20 to 30 minutes is maybe... I don't know, you probably can't leave a toddler alone for 20 or 30 minutes, but it's a little bit older than a toddler. With a toddler, you can be in the same room but not interacting with them every single second for 20 minutes sometimes. So it's around there. I think we have that similar leash with AGI. And so I think a good definition of AGI is when does it become economically profitable for people to run agents indefinitely?

So it just never turns off. It's a Claude Code that's always running, it's always doing something, you just never turn it off, and you don't need to because you know that it's worthwhile to keep it on. It's never waiting for you to be like, "Okay, next thing." It'll always respond to you when you're like, "Okay, next thing." But it's off just essentially living its life like a teenager and that is profitable for you. You'd rather have it do that than just wait for you to tell it what to do next. I think that's a good definition of AGI.”

Articles

1/ Fun read on how Compaq beat IBM to dominate the early PC market by Gareth Edwards.

2/ A review of popular ‘white collar’ PEDs (performance-enhancing drugs) such as Vyvanse and Strattera by Park McDougald. The author’s description of his Vyvanse high and low was riveting!

3/ Arjun Ramani, who was previously a reporter in India for The Economist, and now pursuing a PhD at MIT, wrote a fun wrap of what he learnt and experienced during his three or so years reporting in India. It is called Dispatches from India. Think of it as a nerdy cheatsheet to India. It also has some fun podcast, newsletter, and book recommendations that help you decode India.

4/ Tomas Pueyo writes the Uncharted Territories newsletter (long on my mind to subscribe and I may do so soon). I really like his pieces on how history influences geography (such as this piece on Moscow’s location), and in turn how geography shapes history. If you like Jared Diamond (Guns, Germs, and Steel) and Tim Marshall (Prisoners of Geography), you will love him.

5/ Lovely little pieces with lots of wonderful pics and illustrations on urbanist Devon Zuegel’s ambitious plans to create a new walkable town from scratch.

6/ Fascinating but also infuriating read on the entrance exam for jobs in Railways in India. Two horrifying factoids: 1) “During the most recent recruitment drive there were around 90,000 positions on offer and roughly 30m people went for them.” 2) People spend more than 5 years preparing for and taking the exam (which has no set dates).

Bye!

It is time to wrap this! As I shared earlier, you should think of this substack as akin to a monthly magazine - you don’t have to read it all in one sitting, and you don’t have to read all of it!

That is all for now folks. Feedback, or your own ruminations, in the comments or at sp@sajithpai.com (Please don’t send pitches or CVs or anything work-related at my personal id; I won’t be able to respond to them!).

In this chapter, I cover how to pick or select your startup idea / problem to go after. If the pick is done well, it can improve your chances of achieving Product Market Fit (PMF) disproportionately. Thus the importance of the pick. 

If you are an aspiring startup founder then you will find this chapter invaluable, for it gives you a framework to approach your startup ideation exercise. Bonus: there is a section on how to pick your cofounder(s) too. 

For those of you keen to get started, click on the link below.

PMF Playbook: Chapter II - The Pick

What is this PMF book?

Well, clearly you didn’t read open or read my last newsletter! Naughty, naughty! Ok, then a brief context setting para below.

I am writing a book on the topic of Product Market Fit (PMF hereafter), a topic I have been obsessed with for a while, and on which I have written a fair bit. Now, this book I am writing is not a book in the traditional sense of a 250-300 page printed book published by a Penguin or Harper Collins. Rather I am publishing it as an online series, with each chapter distributed freely on the interwebs whenever I finish one. At some point when I release the fifth and last chapter, I will collect all of the chapters and publish them as an ebook (and maybe a printed book) titled ‘The PMF Playbook’.

Given the book is regular sized (50-80k words), and there are only 5 chapters, expect each chapter to be long! This one, ‘Chapter II: The Pick’ is ~20k words! For the book structure, visit the book microsite at sajithpai.com/pmfplaybook

‘The Pick’ Chapter Summary

Let us quickly dive into the chapter highlights so you know what you are getting!

1/ The pick or the problem space you will work in is the single biggest early stage decision, for it sets the ‘constraints and boundaries’ of what you are going to be working on for the rest of the 2-10+ years. Also a founder has at best 3-4 picks in their career. So, take your time to get the pick right. The best founders don’t hesitate to invest a lot of time here.

2/ To get the pick right evaluate how they rank on these three criteria: 

• large attackable problem (reflecting the VC question ‘why this?’)

• inflection points / timing (VC query: ‘why now?’

• founder-problem fit (‘why you?’)

Make sure your pick hits at least two if not all three of the above criteria!

3/ To arrive at the pick, founders can take any of these four routes

1. Personal pain (e.g., Zomato, Uber)

2. Personal experience (Freshworks, Coinbase)

3. Prospecting or systematic exploration (MakeMyTrip, Vanta)

4. Opportunism (Ola, DealShare) 

Finally you can also arrive at a pick by pivoting from a different initial pick.

I got ChatGPT to create a graphic to represent the four routes to arriving at the pick.

4/ The process of arriving at the pick goes through two sequential phases:

• Problem discovery: where you expand the set of problems to pursue, through primary and secondary research, and hone in on a problem or two or three to pursue. 

• Problem validation: where you again conduct conversations with customers, and do desktop research if needed, to validate that the problems you have picked are meaningful to explore. At this stage you can start building a solution / MVP.

5/ Finally on picking cofounder(s): If you aren't able to find a cofounder organically, there are frameworks, playbooks, orgs to help in cofounder dating. But it is not the end of the world if you still don’t find one. There are ways to convince investors, and supporting mechanisms and ways to make solo founding work. If anything, the risks of a cofounder with whom you have a conflict is far more dangerous for the company than being a solo founder, so don’t rush into a cofounder partnership.

Subscribe now

You can read the chapter at PMF Playbook: Chapter II - The Pick

Bye!

Would love to hear from you on your thoughts, observations, criticism or praise here in the comments or at sp@sajithpai.com (Please don’t send pitches or CVs or anything work-related at this id; I won’t respond to them).

Now, readers, this is a special edition of the newsletter. We will dispense with regular programming to bring you something I have been working on for a long time.

Some of you may know I am writing a book on the topic of Product Market Fit (PMF hereafter). Now, it is not a book in the traditional sense of a 200-300 page printed book published by a Penguin or Harper Collins. Rather I am publishing it as an online series, with each chapter distributed freely on the interwebs whenever I finish one. At some point when I release the last chapter, I will collect all of the chapters and publish them as an ebook (and maybe a printed book) titled The PMF Playbook.

Here is Chapter I of the book, introducing my PMF framework and definition. Given there are only five chapters, and I see this as a regular sized book (50-80k words) you can expect each chapter to be long:) The first chapter is about 13.5k words long.

For those of you keen to get started right away, here is the link to Chapter I of the PMF Playbook below.

PMF Playbook: Chapter I - Understanding PMF

For those of you who want to know more about why I am writing this book, here goes.

Why we need the PMF Playbook

Product Market Fit (PMF) is arguably the most important milestone for an early-stage startup. ~90% of startups fail, and the single biggest reason for that is failure to achieve PMF. Additionally, achieving product-market fit (PMF here onwards) is a key qualification criteria for the Series A round, which sets the startup for eventual success. No wonder that Marc Andreessen, who popularised PMF  called getting to PMF ‘the only thing that matters’. Given this, it is a pity that PMF is one of the most misunderstood and misused terms in startup terminology, with varied definitions including touchy-feely ones like ‘PMF is like love (or porn), you’ll know it when you have it (see it)’.

The lack of common ground over a definition of PMF means that founders do not have a commonly understood framework for understanding it and working towards PMF. This matters. Today, when the venture financing market is $368b large globally, with over 90% of this Series A and beyond (typically post-PMF funding), the importance of hitting PMF (or not) cannot be overstated. Without PMF the startup fails, and this has ripple effects on how the downstream capital is deployed. It is inefficient for the venture industry to have such an important step in the startup’s journey remain fuzzy, left to each founder to feel their way around and determine for themselves. 

Hence this book. As an early stage venture capitalist, I have seen that the single biggest determinant of later-stage success is the early-stage startup achieving PMF. It is the highest leverage area I can impact and influence, and I focus on this as a key area of support for the startups I work with.. I have worked closely with over a dozen startups directly, helping them navigate the path to PMF, and have simultaneously tracked the journeys of over a hundred others, to arrive at a framework for founders to get their startups to PMF.

My PMF framework

In the simple framework that I lay out in the book, I tease apart PMF or product-market fit, into two stages or parts. The first stage, or part, is PPF or product to problem fit, and the second is MMF, or (go-to-market) motion to market fit. When you achieve PPF (product to problem fit) you have eliminated product risk to a large degree, that is, you have a working product that solves the problem and / or addresses the ‘job to be done’ of a clear customer persona. Once you have achieved PPF, you then need to work towards achieving MMF (GTM or go-to-market motion to market fit). Realising MMF helps you eliminate market risk largely, and helps you arrive at a working scalable playbook for efficiently acquiring more and more of your desired persona. Achieving PPF and then MMF, means you have hit PMF.

In this book, I will help you with a clear playbook and guidemap to help you, first walk towards PPF, and then MMF, illustrating best practices with multiple examples and case studies. I will quote stories from PMF journeys covering a wide range of startups, B2B and B2C, and some B2B2C, across sectors and across geographies such as US, India, China. Each PMF story is different, but at its heart, each PMF story is also similar. Through these case studies of different startup journeys, some successful and some not, I will draw out the key elements of the above PMF framework, setting out a universal definition for PMF, as well as laying out a systematic step-by-step plan to work to PMF.

Structure of the book

The playbook has five parts or chapters, of which this is the first. The chapters are:

• Chapter I: Understanding PMF (link to chapter) - why it matters, and a definition for PMF. I share that PMF is actually two fits, Product to Problem Fit or PPF, and Motion (as in GTM Motion) to Market Fit, or MMF. PMF = PPF + MMF.

• Chapter II:  The Pick (releasing on 8th August 2025) - how to pick or select your startup idea / problem to go after. I argue that if the pick is done well, it can improve your chances of achieving PMF disproportionately. This chapter covers how to get the pick right.

• Chapter III: Achieving PPF - PPF or Product-Problem Fit is the first part of PMF. This chapter gives you the different sub-stages in the process to PPF, and how to successfully iterate towards PPF

• Chapter IV: Achieving MMF - MMF or Motion-Market Fit is the second part of PMF. This chapter takes you through the iteration process to get you successfully to MMF, and thereby hit PMF.

• Chapter V: After PMF - What do you need to do after achieving PMF? A look at how to hold on to PMF, as well as the playbook for the post-PMF phase of the startup’s journey. 

Subscribe now

Who is this for?

Founders in the early days of their startup, aspiring founders, and ‘intrapreneurs’ launching a new unit / product in a larger company, will find this book most relevant, as they can use it as a systematic guide to work towards PMF, removing guesswork and fuzziness, out of the startup journey. PMF is easily the single biggest milestone in the early startup’s journey. Don’t leave it to chance.

Link to PMF Playbook: Chapter I - Understanding PMF

Bye

Would love to hear from you on your thoughts, observations, criticism or praise here in the comments or at sp@sajithpai.com (Please don’t send pitches or CVs or anything work-related at this id; I won’t respond to them).

Quick housekeeping announcements for the new subscribers. The newsletter has two permanent sections: Writings - where I usually write and / or refer to one or more original pieces that I published in the previous months, typically about venture or the startup ecosystem, and Readings - about what I read and learnt about. My reading diet is tilted rather heavily in favour of books and podcast transcripts, and against articles / newsletters. This will naturally reflect in the reading list.

This is a long newsletter - think of it as akin to a monthly magazine from me (only the frequency may not be monthly!). I don’t know if you can read this entire newsletter (and peruse the links) in one sitting, and even if you do a second run ( which I very much doubt), you will have to pick and choose what to focus on. A good way to read this newsletter is to certainly read my original writing(s) below, and then glance through the rest and pick 1-2-3 items that pique your interest. Anything more is a bonus!

Writings

My AMA on Accel India’s SeedToScale website

I did an AMA for the SeedToScale website (run by Accel India). They crowdsourced 7 questions re the themes in the Indus Valley Report 2025. I answer questions across topics such as what the moats in the age of AI are, if India will become a manufacturing power, our perspectives on QCom, on how founders without traction or growth can access capital.

The episode is here:

The transcript of the episode is on my website.

Here is one of the seven questions and my answer:

So question number seven, traction versus capital chicken egg. Many early stage consumer tech founders face this paradox. VCs want traction before investing, but traction often requires upfront capital. What’s your advice for founders facing this?

So the secret of venture is that there are two types of founders and there are two types of venture funding mechanisms that have evolved to cater to these. So if you’re a second time founder, you don’t need traction. You’ve proven yourself through previous company founding. You’ve done well. Or even if you haven’t done well, you’ve shown that you have the requisite experience.

So typically, VCs are happy to fund second time founders on paper plans alone. And there’s a lot of money that can kind of flow into these founders. But if you’re a first time founder, yes, you do need to show some traction.

And yeah, you’re right in saying that if you don’t get access to funds, how will you show traction? So there are two bits of advice I have for you. One is figure out what stage of VCs you’re talking to. If you are a first time founder, then try and take some money from friends and family or angel investors who are happy to kind of fund you.

For example, you’re working in a high growth startup and you can ask the founder of that high growth startup; if it’s a unicorn, then even better because they would have had some liquidity, some outcomes, and they’ll be able to kind of give you some starter capital. Through that starter capital, you can build the business to a certain stage, you can show growth, and then approach a VC who’s relevant for that stage, like a pre-seed VC or a seed VC. And then this is the capital that you get, which gets you to the next stage, you can approach a Series A VC.

So I would say stage your capital raising requirements. Don’t come to a series A VC if you’re a first time founder with a paper plan idea. Very, very unlikely that you’re going to get funded.

Second, let’s say that you have growth, you have traction, but VCs are passing on you saying that’s not enough. So what should you do? What you can do is to research out which VC has an interest or a thesis in your sector. Don’t approach every single VC. Go find out who those specific VCs are and build a relationship with them. Because they believe in your sector, in the problems that you’re attacking, and they have a thesis in that sector, they have a prepared mind, and they may be willing to take a risk. They may say that, hey, sure, we would have ideally liked this revenue, but, you know, willing to take the chance on you.

So you need one VC to say yes, right? So these are the two bits of advice I would tell you to solve the capital versus traction chicken egg problem.

The best VCs are long preloaded context windows for their founders

Short piece on how the best VCs continually update their knowledge of the company, the people, its challenges (effectively context about the company) so that founders reduce time to query on key decisions. Without the context, the founder has to spend a lot of time setting the context with the VC, thus taking time. The best VCs have the company context ready in their minds thus saving the founder time, and increasing the chances that founder will reach out to them over another VC.

Link to the piece. (Originally published in newsletter #32)

Readings

Books

I completed four books, and left more than a few unfinished. Some of these will be permanently unread but there are a few I will get back to completing. One reason is that I am not able to read in chunks due to lack of time. A lot of reading time is really on weekends. That means if I read 50-100 pages on weekends, then I have to wait till the next weekend for the next 50-100, and then the challenge is that I have lost context. My present reading style thus lends itself to shorter books that I can read over a weekend across 2-3 sittings (books 2-4 in the below list were all read over a day / weekend), or something I can read for 30-45 mins daily such as a book of short stories or a non-fiction book with short independent chapters, e.g., Burkeman’s book below. Janan Ganesh refers to this in a piece sharing reading advice: “Don’t read fewer than 50 pages in a sitting. The cost of pecking at a book here and there is a lost sense of its narrative wholeness. (“If you read a novel in more than two weeks, you don’t read the novel” — Philip Roth.)”

Here we go.

Meditations for Mortals - Oliver Burkeman

Those who have read Oliver Burkeman's previous book, the best-selling 'Four Thousand Weeks' will find a lot that is familiar. The key theme of 'Four Thousand Weeks' (so called because that is the average life span) is that life is short, and you can't do it all, and you need to choose a few and enjoy them. That advice is carried over here as well and informs many chapters of this book as well. In addition there is a related theme of how we try to create productivity systems and processes when all we need to do is just start doing stuff. Then there are a few practical tips, all around the theme of not trying to stufff your day with tasks, and not building your life around productivity systems such as working on creative pursuits 3-4 hrs a day tops, sticking to a dailyish schedule (not the Seinfeld Strategy of 'not breaking the chain'), treating your to read list like a river not a bucket, that is, dip in and out, and dont feel forced to read something; and so on. Overall a decent read, and will appeal especially to those who like to dip into productivity porn.

Link to my summary of the book.

Paper Belt on Fire - Michael Gibson

Not as well-written or as well-edited a book as I expected; one that could have been much tighter, though still relevant as a history of the Thiel Fellowship and the 1517 fund, the largest student-focused venture fund. As a venture nerd, I found the book interesting enough, with a glimpse into Peter Thiel's thinking and way of working as the highlight, but to those outside (especially those with no axe to grind re U.S. culture wars), it may not be as useful / interesting.

All In: Memoirs of the Freshworks Founder - Girish Mathrubootham w Pankaj Misha

Girish Mathrubootham, one of the central figures in the Indian startup sphere, thanks to his founding of Freshworks, as well as pioneering the key community initiative SaaSBoomi, shares his backstory, covering his childhood (mentions but doesnt dwell too much on his parents' divorce, which was rare for that era in India), his attempts at early entrepreneurship teaching Java, his growth at Zoho, and then the founding and scaling of Freshworks. It is a wonderful portrait, raw and honest on several fronts, but ultimately a tad unsatisfying. I think it is because the best businesse (auto)biographies have the qualities of what Girish preferred in SaaSBoomi talks - anecdotal, authentic, and actionable. While this autobiography is anecdotal, and authentic, it falls short of having any actionable insight. That perhaps is why I found it a tad bit unsatisfying. Still, full credit to Girish for authoring this, and being vulnerable. More and more Indian startup founders should author their memoirs. One I would certainly like to read is Sanjiv Bikchandani's.

Alpha Girls - Julian Guthrie

Julian Guthrie covers the story of four women VCs, and the challenges they face as they navigate their careers and straddle professional + personal lives. Very candid, and empathetic portrait. Venture nerds will enjoy this (lots of fun stories incl how the Facebook deal was done, the early days of Salesforce etc.) Must read for women investors, their bosses, and their husbands; for the picture that is painted from these portraits is not a pretty one. It says that the husbands and bosses / partners dont always support their ambitious women, and this makes it tough for women to juggle these multiple roles.

Articles

1/ Lenny Rachitsky: To write consistently, write only what you are curious about

Link to article.

Lenny: “…Initially, my heuristic was 80% writing about what I’m energized/curious/excited to write about and 20% writing about what people want me to write about. These days, it’s actually 100% what I’m curious about. I now never publish anything only because I know it’ll do well.

This is actually a very important lesson I’ve learned: In this line of work, individual (viral) posts come and go, but it’s all about how long you can stick with it. One viral post: easy. One post every week for five years: much less easy. You need to prioritize stamina over anything else. In other words, play ‘infinite games’.”

2/ Elliot Jaques’s time horizon – strata fit

Link to article.

Beginning to see Elliot Jaques pop up off and on, most recently on the Roelof Botha episode with Mario Gabiele / The Generalist (see above). Here is an excerpt from an old but good piece on the social scientist. (He passed away in 2003)

Art Kleiner: “But if everyone agreed on the value of jobs, what did that value depend upon? Dr. Jaques was stumped until, one morning, three shop stewards burst in to tell him they’d figured it out. The critical difference had to do with time. Factory floor operators were paid by the hour, junior officers by the week, managers by the month, and executives by the year. Within two years, Dr. Jaques had refined this insight to the concept of “time span” — the value of every job could be measured by the length of time it took to carry out its longest-running assignment. (He also called it a “by-when,” his name for the explicit or implicit deadline embedded in every task.) A maintenance operator on a factory floor might wrap up all tasks within a 24-hour period, but a purchasing manager might need up to three months to finalize a contract, and a marketing VP might take two years to plan and implement the introduction of a new soap. The longer the time span, the greater the amount of “felt-fair pay” that was appropriate to earn.

In the early 1980s, he codified his findings. The true fit between a person and a job, he has concluded, depends on the match between the “time span” of the job and the potential capabilities of the person.

At the heart of the Jaques work is this double helix of human capability in organizations. On one side of the helix are the “categories” (as Dr. Jaques calls them) of people’s ability to handle cognitive complexity. Each of us is born with a certain potential ability to handle complexity. By the time we come of age (at, say, 18), if we’ve matured to that potential, then we can handle assignments of three months, a year, two years, five years, or more. This “time horizon” is more or less hardwired into us (not just in our minds, but in our beings, Dr. Jaques would say). Some people start out higher than others. On the bright side, we all continue to mature all our lives, making occasional palpable leaps in our ability about every 15 years, as we cross a threshold into the next level of capability. (If you realize that you can suddenly handle tasks that seemed unfathomable before, you’ve probably made such a leap recently.)

Of course, we may not fulfill our potential; we may be blocked by (for example) a physical accident like a stroke, the kind of emotional baggage that leads to neurotic self-destruction, a decision simply not to strive for success, or sheer lack of opportunity to develop our skills — which is one reason hierarchies are so important for many people.

That brings us to the other side of the double helix. Just like the time horizons (for people), the time spans (for jobs) break naturally, according to Dr. Jaques, into eight levels, which he calls “strata.” The fit between time-horizon levels and strata determines how comfortable we will feel at various positions in a hierarchy.”

3/ Dwarkesh Patel asks what is to AI as the motor car was to petroleum

Link to article.

Dwarkesh has been trying to sensemake developments in AI through his eponymous podcast. In this article, he lists down all the open questions in his mind. I didn’t really understand all of the points (truth!) he raised. Still it was very useful to get a glimpse of his mind and what he sees as the big unsolved questions. Re his query on the industrial-use case of AI (what is the motorcar for AI’s fuel?), I am reminded of Tim Harford’s book ‘Fifty Things That Shaped the Modern Economy’ and the chapter on the dynamo. He writes how the old factories were all based around steam power and needed a central driveshaft to relay steam power. It was only when newer factories / layouts replacing the driveshaft with wires to individual workstations was enabled that electricity’s power could be used by every worker. Today perhaps it is the other way around. AI can be accessed by individuals easily but it perhaps need group or org adoption for its power to be fully realised.

Dwarkesh:

“What is the industrial-scale use case of AI? Between 1859 (when Drake first discovered oil in Pennsylvania), to 1908 (when Henry Ford invented the modern automobile), the main use for crude was as kerosene for lighting. What is the ultimate industrial-scale equivalent use case for AI?

*

How transformative would the AIs of today (March 2025) be even if AI progress stopped here? I’ve personally become more bearish about the economic value of current systems after using them to build miniapps for my podcast: I can’t give them feedback that improves their scope or performance over time, and they can’t deal with unanticipated messy details. But then again, the first personal computers of the 1980s weren’t especially useful either. They were mostly used by a few hobbyists. They had anemic memories and processing power, and there just wasn’t a global network of applications to make them useful yet. Another way to ask this question: imagine that you plopped down a steam engine in a hamlet from 1500. What would they do with it? Nothing! You need complementary technologies. There weren’t perfect steam engine shaped holes in these hamlets; similarly, there aren’t many LLM-shaped holes in today’s world.”

4/ Jake Knapp + John Zeratsky on the Founding Hypothesis

Link to article.

Jake Knapp who came up with the Design Sprint methodology, teams up with Jake Zeratsky to write how founders can lay out your pick or approach into a framework they call a founding hypothesis, which asks them to list out the problem they are going after, the likely customer, the approach, and finally their differentiation (see image below). It is a handy way to structure the startup idea, and forces clarity early on. The article also has a few more bells and whistles, including the process of running a ‘Foundation Sprint’ to structure the pick better and arrive at a common language and buy-in for all founders. Certainly worth a read, especially for early stage founders.

5/ Bob Moore, Crossbeam, on picking the space to play in

Link to article.

Third-time founder Bob Moore covers why his older ventures failed, and why the last one has a fighting chance of success, in this article. Has a detailed section on how he and his cofounder arrived at the startup idea looking at both their affinity for the space, as well as ability to win in the space.

“First, he had to whittle down his list of roughly 100 miscellaneous entries — which ran the gamut from B2B SaaS tools to an escape room franchise.

Too often, founders — especially those earlier in their careers — fail to take their own strengths into account when choosing an idea, merely chasing market trends or their own passions. When Moore started RJMetrics, he and Stein were fresh off a two-year stint in venture capital, hungry for a startup of their own. But when they quit their investor day jobs to get RJMetrics off the ground, they didn’t have a strategic game plan beyond wanting in on the heating-up analytics Market. “We went in as mercenaries. We wanted in on this startup game and big data was increasingly a thing. I knew how to write a damn good SQL query. But that was all we had,” says Moore.

Looking back on it now, Moore thinks one of the contributing factors to RJMetrics’ shorter shelf-life was that the founding duo lacked a sense of where the market was headed. “When we started RJMetrics, I didn’t have strong conviction. It may have been something that lit up my brain, but I didn’t even know the word ‘dashboard’ until after I started the company. We didn’t know business intelligence as a market — we didn’t even know who Gartner was,” he says.

Years into building RJMetrics, this absence of a long-term vision became glaring in the product strategy. “Because we weren’t steering with a solid strategy, we pursued all these product micro-optimizations and landed ourselves in a place where we created a company that creates some value for some people. Our growth was stuck on a local maximum. RJMetrics became designed by committee. We didn’t have a core conviction that a certain specific thing ought to exist because that’s where the market was going. That wasn’t there,” says Moore.

So when Moore was assessing ideas for his third startup, he knew he needed to be honest with himself about not only what he was excited to build, but what he was uniquely positioned to build well, given his chops as a multi-time SaaS founder. To do that, he devised a simple founder-market fit pre-screen — a mental matrix with two dimensions of interest and ability:

• Intellectual interest in the problem. How much fun would I have doing this? How much would it light up my Brain?

• Founder aptitude. What is it about my specific experience that makes me predisposed to being good at solving this problem?

“This helped Moore quickly rule out the oddball ideas and pipe dreams. “This exercise took my list of 100 down to 10 or 15 ideas,” he says. With the remaining handful of ideas that landed in the top right quadrant of his mental matrix, Moore wanted to get some outside opinions. But he chose to do things differently for the validation step: He bypassed the classic customer-driven discovery model and instead ran his remaining ideas past fellow founders.

Moore felt that founders could offer more nuanced perspectives — and widen any preconceived notions he might have had about each of these ideas. “Founders are special. They need to develop an extremely high level of empathy and understanding for the needs of people across multiple personas, and also understand a baseline grasp on how markets evolve over time and what makes for something that’s more durable and versatile,” he says.

With the founders, I wasn’t asking, ‘Would you buy this?’ But instead, ‘Would you start this company? And what are the things that you think you might bump into?’ “Rather than narrowing these ideas down into the scope of how a persona would use it, I was able to broaden my horizons of what they could become,” says Moore. “I wasn’t interested in having my next thing be anything other than an IPO-scale business — I wasn’t optimizing for a ‘build it for a few years and sell’ situation. I thought I had one more startup in me and I wanted to see how far I could take it.”

6 / The ultimate cold email / cold outbound handbook

Link to article.

This looong piece by @MattRedler on setting up a cold email / cold outbound strategy is excellent; easily amongst the best pieces of writing on this topic. It is also amongst the best examples of content marketing I have seen. Lots of detail on subtopics such as setting up adjacent domains, how many domains to buy, setting up SPF / DMARC / DKIM, warming your inboxes, who to send to, how to write emails etc., like here

“Most great cold emails do have the following elements in them, not necessarily in this order:

• Personalization

• Strong claim

• Evidence for that claim

• A clear next step

• Shorter than ~200 words

Include all of these in your email and you are, probably, Golden.

The most important piece to clarify here is “Personalization”: lots of people have the idea that this means opening your email with a line like, “Hey, I loved your post on LinkedIn last week!”

And while sometimes personalization might mean a cheesy line about LinkedIn, what’s important is that there is something in your email that makes it feel 1:1. People, more these days than ever, have their mental spam filter on when they get an email from a stranger. If there’s nothing in your email that indicates it’s personal and not a template sent to 1000s of people, you’re probably getting sent straight to trash and possibly marked as spam.”

Here are excerpts from the handbook / article I found interesting. Link.

7/ How consumer brand startups Arata, Fashor, Atomberg scale capital-efficiently

My colleague Rohit Kaul spoke to the founders of Arata, Fashor, and a founding team member at Atomberg – 3 companies across different points of scale to extract learnings.

Link to article.

Given my early stage focus, the lessons from Arata and Fashor resonated a bit more. Three that stood out to me – Arata founders on de-aggregating product performance by channel and aligning marketing comms per channel basis what is working, and how they use the Reason to Believe framework to create their performance ads, and Fashor’s founder on how they tease apart blended CAC to new user CAC and repeat user CAC and how that informs their customer acquisition strategy.

One of Arata’s most important discoveries was that product performance varies dramatically across channels. Bhasin explains, “My top products on quick commerce aren’t the same as on Amazon. Amazon’s top products aren’t my website’s top ones. There’s an overlap, but a visible top product difference across channels.”

This insight led them to analyze data more granularly and link it to custom messaging on different channels. Instead of pushing the same messaging across all platforms, they optimize marketing for each product’s best-performing channel.

“Say a shampoo is my top seller at the aggregate, business level but it may not be the top seller on quick commerce,” notes Bhasin. “But if your marketing spends and overall share of voice or brand voice, is targeted towards that shampoo, you won’t be able to optimize and make most of that specific channel.”

*

Their performance marketing is based on the Reasons to Believe framework.

“There’s a Reasons to Believe (RTB) sheet. What is the product? What is its USP? What are the ingredients? What are the benefits? How do the ingredients support those benefits and USP? What is the visual representation? What is the sensorial representation?”

Based on this RTB framework, Arata has developed a scientific approach to performance ads. “We’ve broken performance ads down to a science—what to appear in the first three seconds, in six seconds, eight seconds, all the way to 15 seconds,” explains Bhasin. Each segment serves a specific purpose: the first three seconds need a strong hook “to get the consumer to stay, stop scrolling, and watch the ad.”

“The core message will remain the same, but each platform needs specific adaptations,” Bhasin explains. “Amazon requires wide backgrounds, while Flipkart and Myntra allow strips calling out product benefits. The A-plus content (product page) remains similar across channels, just adapted for different specs and sizes.”

Once they know what’s working, they double down using the “double diamond strategy.” As Bhasin explains, “You find what’s working — which creative, which campaign, which tagline. Then you create two more underneath it and again test. So you continuously keep building on what’s working and keep shifting out what’s not working.”

*

Underpinning Fashor’s capital efficiency is a sophisticated approach to metrics tracking, focusing on data that directly informs profitability:

Segmented CAC: “We split our new customer CAC and repeat customer CAC on an everyday basis. You have to split. Don’t just look at blended CAC.”

This separation is critical for managing unit economics. “On repeat customers, you need to make a profit. You know your gross margin and variable costs… So you have to ensure your performance marketing cost generates a profit for you.”

New customer acquisition requires investment: “On new customers, initially there will be a burn, because new customer CAC is higher.”

The investment decision is strictly based on expected returns. “We accept the burn because we know over 40% of our customers repeat, and we know their frequency and lifetime value. As long as the LTV to CAC ratio is above 6x, we’re happy to invest in acquiring new customers.”

8 / Reducto’s Path to PMF

Link to article.

This is another of the Path to PMF series that First Round Review (an online site from storied seed fund First Round Capital) puts out. Each post takes the reader through the journey of a company and how they found PMF or Product Market Fit. I found this piece particularly interesting as it is a great example of how lukewarm reaction to their initial product (a long-term memory solution for language models) persuaded the founders to rethink their initial approach, and take up a new approach (making it easy to extract data in the right manner from PDFs), one which came from carefully listening to what their potential customers were asking. If you have read Mom’s Test or heard of the importance of problem validation, well, there is no better example. TLDR: It is either hell yes, or no.

“Hundreds of folks asked to be onboarded to the product, then called Remembrall (“Harry Potter” fanatics will notice a pattern with these company names), but early onboarding calls hinted that they were a bit too early to the space.

They had conversations with enthusiasts who would maybe try adding it to their AI application. “It was never the case where people were saying, ‘I’ve noticed that customers get angry at my product because X, Y, and Z and Remembrall can fix it.’ That was the first signal. The second signal was that people were maybe willing to pay $10-20 a month because they found the idea interesting. But no one’s product team needed it,” he says.

We set up demo calls with everyone who expressed interest and we asked what their use case was and what problems the product would solve for them. And we would very rarely get a real answer. It was more of a ‘This seems cool’ curiosity.”

…

“One of the most common feature requests for Remembrall was, ‘Hey, you’re managing my user’s chat history, can you manage the files that they’re uploading as well?” Abraham says. “We went into our projects expecting to help teams with fun ML problems, but very quickly learned that one of the biggest bottlenecks across most pipelines was actually well before retrieval or generation.”

So the co-founders built a very simple solution — they would upload the docs, parse them using an external parsing solution, and then chunk the information for you. “It’s embarrassing to look back on it now, it was a very ugly Streamlit app with a super simple document segmentation tool. It would do nothing other than split your documents into little boxes of content. I can’t stress this enough — it was literally a weekend project that we threw together,” says Abraham.

But they posted it on YC’s forum anyway, and the response was immediate and overwhelming. “We started getting replies, ‘This is better than what I’m getting from Textract. Is this a hosted API? Where’s the Stripe link?’ The pull was much stronger than everything else we had worked on,” he says.

…

Unlike the “seems cool!” enthusiasm for extended LLM memory, there was a distinct need and a massive pain point. “These companies are not trying to spend many hours of engineering time on PDF processing, but it’s the bottleneck that’s stopping them from building the things that actually matter. If we can be that ingestion team for our customers and take that problem off their plate, that’s clearly very valuable,” he says.

We had spent enough time exploring things that were not resonating. In comparison, it felt like we were getting punched in the face by this new idea — it was something people cared about an order of magnitude more.”

9/ Your ICP (Ideal Customer Persona) should be uncomfortably narrow

Link to article.

Good read with a lot of examples on how the likes of Vanta, Clay (see below), Webflow etc., all iterated towards their ideal customer persona or ICP; essentially the specific target persona the product is aimed at. The core mantra is that early on, your ICP should be uncomfortably narrow. As the article puts it: “It should be so narrow that when you describe what you’re building to friends and who it’s for, they think you’re slightly crazy for trying to do something so niche.” Subsequently as you hit product market fit and raise more funds, and you can widen the ICP aperture, and expand your feature set to cater to the wider ICP. But early on, keep it uncomfortably narrow!

“Clay is a tool for connecting APIs to your spreadsheets to enrich your data, and everyone wanted a piece of it. Recruiters told founder Kareem Amin how useful the product was for finding candidates. Salespeople wanted to use the platform for their inbound and outbound leads. Front-end engineers could use the spreadsheet as a low-code backend.

All this interest might sound great, but five years in, revenue was still hovering near zero. The warning signs were there when the initial spark died off quickly. “People would feel excited by the possibilities the product opened. But they weren’t always going back and using it the next day,” Amin told us. “So actually we had a lot of, ‘Wow, this is so powerful!’ and then no usage, or inconsistent usage.”

The Clay team accidentally cast too wide a net by building features every prospect wanted. As Amin explains it: “When you’re an early startup team, one of your strengths is that you’re malleable. A prospect can say, ‘Oh, could you guys do this?’ or ‘Are you guys this?’ And then you can become that, quite easily. What I’ve learned is that you have to know when to be malleable,” he says. “You can’t be changing the value prop or even the product itself from meeting to meeting. When you narrow the scope, it feels claustrophobic. Why are we doing something that’s smaller when we could be doing something bigger? Eventually, we realized that by narrowing down our scope, we were actually increasing our value.”

Finally, to escape the everything-to-everyone trap, Amin called a bold play: pick one specific ICP and go all in. They started with outbound sales teams.

“It wasn’t so much that I was 100% sure that outbound was the right call, although it was a faster starting point because all companies need it, versus typically only bigger companies needing inbound support, ” says Amin. “It was more that I realized we need to pick one thing at a time, test it out clearly and get feedback that we can react to quickly. That’s when we’d earn the right to execute on the more expansive parts of our mission.”

10 / The story of Founders Fund

Link to the story series page (paywalled).

Mario Gabriele’s quartet on Founders Fund (long enough to be a short book!) is utterly riveting. He covers its origin story, its distinctive philosophy, its polarising approach, and impact on the ecosystem, and how it is set up for selective but all in bets such as Palantir, Anduril, SpaceX, Ramp etc. There isn’t a fund like this, and perhaps never will be.

Podcasts

1/ Marc Andreessen doubts whether AI will disrupt early-stage VC

Link to podcast.

A little late to this podcast. Nothing special as such in the podcast, though this passage, on why he thinks early stage VC will not be significantly affected by AI, stood out. I quite agree. Early stage venture is all about identifying talent and picking people. It is also a place where in picking people you have to sometimes cast off past patterns / not be prisoners of patterns. My colleague Karthik said once: “Venture is a pattern-matching business, but the only stories worth telling are those built by exceptions”. Even if AI becomes the best pattern matcher, it will assign those weights and biases to past patterns. Yes, you can program it to reduce those weights and biases, and assign more importance to present context / state, but humans will still for a long while, be the best real-time weighers of state, context, and past patterns all together at once.

“Marc: What I’m about to say may just be wishful thinking on my part. I might be the last Japanese soldier on the remote island in 1948 by saying what I’m about to say. I’m going to attempt fate. But I’m going to say, look, so much of what we do on the early side in the first five years is really very deep evaluation of individual people, and then it’s working with those people in very deep partnership. And this is one of the reasons, by the way, that venture doesn’t scale well, particularly venture doesn’t scale well geographically. The geographic scale experiments tend not to work. And the reason is just because you end up having to be face to face with the people for a long time, both during the evaluation process, but also during the building process. Because in the first five years, these companies generally aren’t on autopilot. You actually work with them a lot to help make sure that they do the things that they’re going to need to succeed. There’s a part of this that is very, very deep. Interpersonal relationships, conversations, interactions, coaching, by the way. We learn from them, they learn from us. It’s a lot of back and forth. We don’t come in with all the answers, but we have one lens because we see a panorama. They have another lens because they’re in the specific details a lot more than we are. And so there’s tremendous interpersonal interaction that happens. Tyler Cowen talks about this, I think he calls it project picking.

Certainly talent scouting would be another version of this, which is basically like, if you look back over hundreds of years for any new area of human endeavor, you almost always have this thing where you have very idiosyncratic people who are trying to do something new. And then there’s some professional support layer of the people who fund them and support them for the music industry. That’s David Geffen finding all the early folk artists and turning them into rock stars. Or it’s David O. Selznick finding the early movie actors and turning them into movie stars. Or it’s the guys sitting in a cafe, a tavern in Maine 500 years ago, figuring out which whaling captains are going to be able to go get the whale there. You know, it’s Queen Isabella getting the pitch from Christopher Columbus in the royal chambers and saying, yeah, that sounds plausible. Why not? There’s this alchemy that has developed over time between the people who do the new thing and then the people who sort of enable, support and fund those people. Let’s just say, like, there’s no guarantee that this continues, but that’s like a 400, 500 year endeavor, honestly. Probably it’s thousands of years old. You probably had tribal chieftains 2,000 years ago, 3,000 years ago, sitting around a fire, and the young warrior would come up and say, I want to go take a hunting party into this other thing and I want to see if there’s better game over there. And the chief sitting around the fire trying to figure out whether to say yes or no. So there’s something very human about that. My guess would be that that continues. Having said that, if I meet the algorithm that can do that better than I can, I will instantly retire. We’ll see what happens.”

2/ Roelof Botha on the two trackers they send out every week at Sequoia

Link to podcast.

Good podcast, though for regular Sequoia-watchers, some of the content is a repeat of what they have heard / read. To me, as a VC here in India, what stands out is Sequoia’s obsession to enhance themselves in every aspect of venture craft, from access (by leveraging AI) to better picking by honing their decision-making through a) recognising cognitive biases + structuring their dealmaking process to factor these biases in, as well as b) combating these biases by using cognitive decision-aids such as their monday trackers etc.

Roelof: “We have an internal tracker here at Sequoia. We send it out every Monday as a reminder to be rational and level-headed as we look at late-stage private companies.

There’s about 690 public tech companies that we include in this basket. And we look at the current median multiple, enterprise value to revenue multiple, of this entire basket of companies. And right now, it’s sitting at the 60th percentile of the last two decades….in addition to that particular tracker, we have a sheet that we hand out that summarizes all the investments we’ve made to date in the current fund that we’re investing. And it’s a useful way to just reflect on what is the quality of the companies we’re assessing today. How does it measure up to the companies we’ve agreed to invest in?

And admittedly, there are mistakes in there and there’s some good decisions in there. But it’s a useful mechanism because humans are very good relative decision makers. Now, I’ve read some interesting behavioral economics research on this, where if I show you three different homes, and two of them are Spanish and one of them is Tudor, you’ll probably pick the nicer of the two Spanish homes just because you have a comparison.

If I showed you one Spanish and two Tudors, you might choose the nicer of the two Tudors. And so humans are just a little bit stuck in this relativism in how we make decisions. And so if you can widen the aperture of things that you put in that consideration set, I think it helps you make better decisions.

“Otherwise, you might just think about how good is this company relative to what else we’re looking at today or what else we’ve seen in the last month. You step back, you look at a wider set and it helps you really think about what quality means. Does this company have the potential to become a legendary company in the Sequoia language?”

More excerpts of what I found interesting here.

3/ Varun Mohan, Windsurf AI, on the changing role of the software engineer

Link to podcast.

Good read / listen for context-gathering around understanding how a AI-native high velocity startup founder thinks and executes (though I didn’t find anything dramatically new). His view on AI and coding in the light of GenAI’s rapid improvements in coding were interesting. Broadly 1/ Engineer’s role moving from coding to reviewing. 2/ Alpha in coding now moving to prioritisation / what to build (now what does this imply for PMs?!)

Varun: “One of the key pieces that we recognized was, with this new paradigm with AI, AI was probably going to write well over 90% of the software, in which case the role of a developer and what they’re doing in the IDE is maybe reviewing code. Maybe it’s actually a little bit different than what it was in the past.

…

The goal of AI has now changed a lot in that it is now modifying large chunks of code for you. And the job of a developer now is to actually review a lot of the code that the AI has generated.

…

I think when we think about what is an engineer actually doing, it probably falls into three buckets, right? What should I solve for? How should I solve it? And then solving it. I guess everyone who’s working in this space is probably increasingly convinced that solving it, which is just the pure, “I know how I’m going to do it” and just going and doing it, AI is going to handle vast majority, if not all of it.

In fact, it probably actually, with some of the work that we’ve done in terms of deeply understanding code bases, how should I solve it is also going to get closer and closer to getting done. If you deeply understand the environment inside an organization, if you deeply understand the code base, how you should solve it, given best practices when the company also gets solved.

So I think what engineering kind of goes to is actually what you wanted engineers to do in the first place, which is, what are the most important business problems that we do need to solve? What are the most important capabilities that we need our application, our product to have? And actually going and prioritizing those and actually going and making the right technical decisions to go out and doing it. And I think that’s where engineering is probably heading towards.”

4/ Robin Dunbar of Dunbar’s number fame, on the different relationship numbers that govern your life

Link to podcast.

Robin: “So you have these series of layers going out from you, which increased in size, but the quality of the relationship and the frequencies that you contact them gets smaller and smaller, smaller, lower and lower as you go further out. So these layers occur at very, very specific numbers. Core is really this 150 number, Dunbar’s number. But within that, there are a series of layers at 50, 15, 5 and the smallest one, 1.5.

And then beyond the 150 going out further, there are layers at 500, 1,500, the last possible one is 5,000 because 5,000 identifies the number of faces you can say whether you’ve seen them or not before. In other words, it’s the distinction between a complete stranger. I’ve never seen that face in my life and somebody you’ve seen but probably, for most of them, you don’t know much about. You don’t even know their name maybe.

But then the 1,500 layer within that, which actually turns out to be the typical size of tribes in hunter-gatherer societies. The distinction there is that you can put names to faces. As you come further in the 500 layers, the layer of acquaintances, many of the people you work with will be in that layer. In other words, you might go and have a beer with them after work. You might even spend a weekend away for some big work-related project with them, but you would never invite them back to your home for a big party.

Your 150 layer, well, that’s what I always call your bar mitzvah, weddings and funeral party. These are the people who will turn up out of obligation to you on that big once-in-a-lifetime event. You may not know they’re there in the third case, the funeral party, but believe me, they will be there. And then as you come in lower, so the relationships getting stronger and stronger.

The 15 layer is your sympathy group, people who you would feel extremely upset about if they die. That’s been known for a very long time. I didn’t discover that. And then inside that is this layer, five is the number’s layer, which is what we call the shoulder to cry on friends. And that layer turns out to be very important for you. It usually consists of two family members and two friends plus an another one per my design.

That number turns out to be the one that has the most influence on your general health and well-being. So the best predictor of your mental health and well-being, your physical health well-being, and even how long you’re going to live into the future from today is predicted by the number and quality of friendships you have in that layer. The five is an average. So if you only have three don’t panic yet, because introverts tend to prefer to have fewer people but have stronger friendships. As a result, extroverts tend to prefer slightly more people but have weaker friendships, those kind of effects. But on average, very much five. So as I’d like to say, if you really want to live forever, just make sure you’ve got five friends.”

Above diagram via Robin Dunbar, from his book ‘Friends’.

Patrick: And what about the 1.5. That seems like an odd number at the end of the cycle.

Robin: I always use to sort of come out with this joke when I was giving talks because I actually thought it was a joke, which was, well, just look at these series of circles and how very tight, the kind of fractal mathematical structure is. Each layer is three times the size of the layer inside it. And remember, these layers count cumulatively. So your 150 layer includes the 50 people in the layer inside. It’s not an addition. But just look at the regularity of these structuring, of these numbers, and surely, there’s a layer missing, if you project backwards.

Because you only knew about the five, we thought the five is the smallest number. If you project backwards, there’s a number missing and what is it? Well, it’s 1.5 and everybody would say, “How can you have 1.5 relationships?” The answer is obvious think about it. Half the population has one very, very close friend in that circle. And the other half of the population has two, what might the difference be? Well, the answer is gender. It’s obvious.

And the question is, why are women having two? And the answer is they have a platonic friend called the best friend forever. BFF. And that’s nearly always another woman, not 100%. 85% of women at any one time, have a best friend forever because the social psychologists who’ve explored this question have told us that constant reason that women always hear this because their romantic partner who statistically, obviously, is usually a male is completely useless at emotional-ish. You need somebody else who’s better qualified to deal with the emotional issues to sort of deal with that part of your life and the only person that falls into that little bracket as it were, is a girlfriend. The average is the male’s one and the women’s two that makes the 1.5 of that layer.

The layers are created by essentially the amount of time you spend doing stuff with different people. So obviously, the inner core layer, these layers in your social network have very specific frequencies of interaction you must have to keep the person in that layer. So the people in your five shoulder to cry on friends layer, you have to see at least once a week. That’s the minimum. The people in the 15, sympathy group layer next outside that you have to see at least once a month. If you see them less, those relationships decay inexorably.

It takes about 3 years for somebody to go from being a member of your 15 sympathy group to falling out of your 150 and joining the layer of acquaintances, which includes your favorite barista that you get your glass of coffee from every morning on the way to work and that kind of thing. So you have to invest time in relationships in proportion to essentially the emotional closeness. And it turns out that emotional closeness of a relationship is highly correlated with the time you invest in it.

Patrick: I’m so fascinated that I think in your research, you show 60% of people’s time they spend with maybe 40% with the closest five and another 20% with the next 10. Time it just strikes me is the resource. It’s the resource that we have to allocate thoughtfully and building those groups, time is the only way to do it, conversation and activity.

5/ David Senra on Jensen Huang’s whiteboard obsession

Link to podcast.

Enjoyed this episode by David Senra where he looks at Jensen Huang’s life through Tae Kim’s book ‘The Nvidia Way’. Lots of interesting snippets that give you a glimpse of how Jensen Huang thinks (a lot closer to Steve Jobs in a way) and acts. A good glimpse into high strategy, especially how to create the conditions and environment that sets you to win. Read ‘Three Teams, Two Seasons’ segment in the excerpts linked to below, to get a glimpse of this. Oh, and fun fact: Jensen Huang has a favourite brand of marker that is sold only in Taiwan.

David: “Their first product, right, is a flop and it’s called the NV1. And so Jensen is actually doing like this postmortem, and he realized they made several critical mistakes with the NV1. So I’m going to read a section from the book to you. Some of these critical mistakes with the NV1 start from positioning to product strategy. He says they had over-designed the card, stuffing it with features no one cared about. The market simply wanted the fastest graphics performance for the best games at a decent price and nothing else. The NV1 could simply not stack up against other cards that were more narrowly designed.

This is what Jensen said: “We learned it was better to do fewer things well than to do too many things. Nobody goes to the store to buy a Swiss Army knife. It is something that you get for Christmas.” Says—this is what James Dyson said: “People do not want all-purpose. They want high-tech specificity.”

*

David: “Some people like Bezos wants a six-page memo. Jobs wants a demo. Jensen wants the whiteboard. So the whiteboard represents both possibility and ephemerality. I can’t pronounce that word, I’m sorry. The belief that a successful idea, no matter how brilliant, must eventually be erased and a new one must take its place. One of the reasons Jensen likes to use the whiteboard as the primary form of communication in meetings is everybody must demonstrate their thought process in real time in front of an audience. With the whiteboard, there is no hiding. I lost count how many times in the book they’re talking about how central, like, how important whiteboarding is to running NVIDIA.

And actually, one of the things that Tay Kim was gracious to send me, he sent me this Wall Street Journal write-up, a review of the book written by this guy named Ben Cohen. Ben has some great writing here in terms of like what he learned from reading the book and the importance of the Whiteboard. It says, “Instead of cloistering himself in a private office, Jensen prefers to work from conference rooms. He does his best thinking at the whiteboard, which he uses so frequently that he has a favorite brand of marker that is only sold in Taiwan.” And so even when he’s traveling, they have to travel with this specific brand of marker, and they have to travel with whiteboards.”

Link to excerpts from the podcast I found interesting.

6/ Nabeel Qureshi on how the best talent brands are polarising

Link to the Lenny Rachitsky Podcast episode.

Good podcast episode spurred by his recent piece on his experience at Palantir – it covers his time at Palantir as a Forward Deployment Engineer, his new startup, and some interesting book recommendations; Impro, which is one of Palantir’s recommended reads, gets a mention, as does Shakespeare’s Henriad(!) and Anna Karenina!

From the podcast episode, I thought this comment by him on how the best (recruitment) brands are polarising, was interesting. The best recruitment brands per Nabeel, push away some people as much as they pull forward certain people.

Nabeel S. Qureshi: “There was also the question of, I think it might have been Thiel who mentioned this, but he thinks that a lot of the best recruiters in the world or the companies that attract talent, they put out this distinctive bat signal and it has to turn some people off. That’s the key of a good, bat signal.

So, I think in the present day, OpenAI and Anthropic, they’re both sucking up some of the best talent that you and I know. And I think one way they do that, and they are sincere in this, but they do really attract people who are almost messianic about the potential of artificial super intelligence and who really believe this is the only thing that matters and it is going to be the biggest thing in the world.

I think Palantir’s version of that was that they were quite focused on things like preserving the West. There was a slogan of Save the Shire, right? So, they were talking about military and defense and intelligence and the importance of that well before everybody else.”

7/ David Senra on Todd Graves’s Raising Cane’s, and focus

Link to Founders Podcast episode.

Todd Graves runs a fast-growing fast food chain with a limited menu focused around Chicken Fingers! David Senra mentions him as a living entrepreneur who he admires greatly. In this podcast episode, he covers why. I thought this passage (below) was particularly good.

“Charlie Munger has his great line, something to the effect that oftentimes in winning, the business system goes ridiculously far by minimizing or maximizing one or a few variables. And he used Costco as an example. And so the clip that I saw was Todd saying that he has this very simple menu, the same menu that he’s had since day one. He had all these people tell him, before he started the business in its early years, that, to this day, what you’re doing is not going to work.

Your menu is too simple. You need to follow the trends; you need to do what your competitors are doing. And he stubbornly believes in doing one thing and doing it the best you can. So he says, “I’ve always believed in doing one thing and doing it better than anybody else.”

If you do what you do well and consistently do it great, your customers will come back. And so, if I add different items to the menu, I wouldn’t be as quick in the drive-thru; if I overcomplicated things, my quality would go down, my speed would go down, and it wouldn’t be our concept. Adding different things and losing focus would make us less special. And so it’s not just that if I narrow the focus and perfect every single detail, I will create the greatest product in my category, but he also understands how everything he does relates to the entire system.

So this idea is like, if I have a simpler menu that makes my product better because I can really focus on it, right? But it means that people come through the drive-thru or into the store. And because they’re. You have four things.

You go into Raising Cane’s, right? You’re like, do you want three chicken fingers? Do you want four or do you want six? It makes you order faster.

And so why is that important? It may not make a difference when you have one or two stores if you save 15 or 30 seconds for each order. But it makes a hell of a difference, right, when you have 800 stores, like he does today. “

We see that

• Focus (limited SKUs) help you create a better product

• Limited SKUs / focus also helps the enabling support mechanisms or other interconnected mechanisms work better (like here fewer SKUs = faster ordering at the drive thru, and hence quicker turnaround)

The big Indian brands that exemplified this thus far have been DMart, Indigo (give me more examples, i collect these). This is also something that I frequently share with the founders I meet, but it is very very hard for me to get the message through:)

8/ Hunter Somerville, Stepstone, on How I Invest

Link to ‘How I Invest’ podcast episode.

This passage from Hunter Somerville of Stepstone, a leading fund of funds in the venture world, on how they track potential emerging managers was fascinating to me. This is exactly how a GP / fund would use Harmonic et al to track potential founders.

Hunter Somerville: When you see someone leave an established brand and start a new organization that has done all of that, sophisticated LPs that are active in venture move pretty quickly and those fund raises happen in very short time frames. Where I think emerging managers are in more jeopardy are when it’s someone that’s a mid level person that’s never run an organization that has a body of work that maybe they sourced but they didn’t cover, they didn’t sit on the board of, or operators that have never invested before, don’t have an investment track record, or have done very tiny angel checks that are just not indicative of their ability to execute as a lead or a number two in seed rounds going forward.

…

Hunter Somerville: You can’t fully anticipate spinouts. You can look at organizations and know where there’s dysfunction or where you think that it’s going to get worse, where you know economics aren’t being distributed appropriately or where there are people that are hanging on too long.

Hunter Somerville: We know those firms, we know where we think it will happen. And there we dig in even further on people’s bodies of work and track records in case it does happen. But as an organization within our venture group, we are tracking attribution and performance for every individual within the funds that we’re in. And the fortunate position we find ourselves in, we are in over 300 venture and growth managers to begin with.

Hunter Somerville: And that allows us to get the data on what each individual partner is doing, the roles they’ve served in sourcing and coverage, in value add post investment. And we compile all of that and go through it as a venture team on a quarterly basis where we look at the rising performers, who’s doing well within those organizations, who we may have not appreciated just from like a diligence effort when you’re spending time with the manager and who’s had really good follow on activity in the investments that they’ve made. And we start building narratives among our team, both as we assess that manager and as we consider whether there’s spin out potential from specific individuals within that manager. And that creates the prepared mind that I was talking about in case something does happen and becomes catalyzed and we then try to move pretty quickly.

Because not only would we like to be active in backing those groups, but we’re very happy to be an anchor and the first group to commit. We don’t need social proof. We don’t really care about that. And we want to be part of the journey with those managers from the very beginning and help them think through building a great organization and picking the right LP partners, which as I mentioned before, is a huge intrinsic risk if you don’t do it.

The episode is a good listen for any aspiring GP / fund manager. Link to excerpts from the podcast I found particularly interesting here.

9/ David Senra on Les Schwab, on the second order effect of incentives

Link to Founders Podcast episode.

Senra: Charlie says over and over again, never ever think about something else when you should be thinking about the power of incentives. Multiple times in Poor Charlie’s Almanack, you see ideas just like that. Incentives rule everything around you.

Never ever think about something else when you should be thinking about the power of incentives. The most important rule in management is get the incentives right.

…

Les Schwab: “This is how more on how we set up the corporation at the very beginning. Each store operates as a separate entity and each store operates as a separate business. The store employees share only in the profits of the store they work in.”

Senra: Let’s go back to the fact that incentives drive behavior. One benefit, one unexpected benefit of sharing profits with employees, less theft from within. Again, never ever think about something else when you should be thinking about the power of incentives. He’s talking about the fact that they will expand.

I think at this point, they have 163 stores and people would analyze this company like where are all your controls? And he’s like, “Well, we don’t have any controls.” Why? Because the incentives are controlling behavior. “We didn’t have many controls. So the thing that held it together was that we ran each store as a separate entity. As long as we made sure that every tyre was billed to them, as long as they made sure that every tyre they sold was billed to the customer, we would come out all right.

10/ Bill Shufelt, Athletic Brewing, on doing things that don’t scale

Link to The Logan Bartlett Podcast episode.

A bit late to this enjoyable episode where Bill Shufelt, hedge fund operator turned cofounder of non-alcoholic beer co, Athletic Brewing, speaks to Logan Bartlett. What I found interesting was how the rising use of wearables, and the increased awareness that comes with it of key markers in the body and how they react to sleep / drinking, creates a forcing function almost against liquor. That was one, and the other was interestingly around doing things that don’t scale in the early days, and how it compounds.

“Logan: As I reflect on like health trends have been moving in a good direction for a long time. And there’s probably. Some element of like the increased wearables. I’ve two on my hands right now. And it becoming self, I mean, listen, these things are such snitches. If you have like a drink the night before, it’s like they know, and they yell at you. And my bed yells at me. I get yelled at every direction. So I have to assume that was like one of the things as well.

Bill: I mean, the nice thing is like when I showed up in my physical this fall, like an annual physical, I was showing up with not only data from my watch and wearables, but like my pre Nuva scan. And like, I was like, this is all the factual information about what’s going on in my body. And like, That just didn’t exist 15 years ago.”

*

“Bill: I don’t know what the customer acquisition cost of spending 10 minutes talking to someone at a booth that I’ve driven six hours to be at is,

Logan: Probably high.

Bill: it’s not great, but like I can’t tell you how many events I’ve done and I’ve gone back to like three years later, like a trail half marathon that I haven’t been at since 2018 people have been like, I met you in 2018 and my fridge has been full of your beer ever since, or like, and in my head I’m like, that’s easily a thousand LTV customer. And um, so I think like you said, scalable before, and I’m a big fan of these like unscalable activities if we do enough of them over and over again, like those scalable activities all of a sudden you turn around and you’re like, Oh wow, we activated 3 – 500 events.”

Link to excerpts from the podcast I found particularly interesting here.

Some more podcasts I liked but haven’t extracted excerpts from

Howard Schultz, Starbucks, on the Acquired Podcast. Late to this terrific podcast episode featuring Howard Schultz, the founder of Starbucks talking through the early, and more recent, history of Starbucks, including the decisions around going Global, expanding the menu etc.

Victor Shih on the Dwarkesh Podcast. Victor Shih, China watcher at UC San Diego; gives a good rundown / view into the internal machinations underlying Chinese political structure, and how policy gets made.

Anton Howes, historian, on the Ideas of India podcast. Fascinating podcast episode, covering how salt taxes and policies around that by the East India Company led to the death of hundreds of thousands of Bengalis and also led to malnutrition and long-term economic malaise (fascinating to read about the great hedge of India, a customs barrier that covered the length of India from Punjab to Bengal to ensure salt wasn’t smuggled). I also did not anticipate that several European conflicts were really salt wars.

Chris Arnade, urban walker, on Conversations with Tyler. Particle-physicist turned Hedge Fund operator, turned walker of cities, Chris Arnade, walks cities, and blogs on them. Through these walks and in the subsequent essays he posts on his substack, he explores urban life, culture, sociology etc. This episode was really interesting.

Bye!

It is time to wrap this! As I shared earlier, you should think of this substack as akin to a monthly magazine - you don’t have to read it all in one sitting, and you don’t have to read all of it!

That is all for now folks. Feedback, or your own ruminations, in the comments or at sp@sajithpai.com (Please don’t send pitches or CVs or anything work-related at my personal id; I won’t respond to them).

Quick housekeeping announcements for the new subscribers. The newsletter has two permanent sections: Writings - where I usually write and / or refer to one or more original pieces that I published in the previous months, typically about venture or the startup ecosystem, and Readings - about what I read and learnt about. My reading diet is tilted rather heavily in favour of books and podcast transcripts, and against articles / newsletters. This will naturally reflect in the reading list.

This is a long newsletter - think of it as akin to a monthly magazine from me (only the frequency may not be monthly!). I don’t know if you can read this entire newsletter (and peruse the links) in one sitting, and even if you do a second run ( which I very much doubt), you will have to pick and choose what to focus on. A good way to read this newsletter is to certainly read my original writing(s) below, and then glance through the rest and pick 1-2-3 items that pique your interest. Anything more is a bonus!

Writings

The Four Ways to Starting Up

I wrote a new post after a while. This looks at the four different routes a founder can take to arrive at the startup idea. These are
- Prospecting (brainstorming different spaces)
- Personal Pain (solving your problem; you are the customer)
- Personal Experience (you arrive at it, basis your work / life journey)
and finally being
- Opportunistic.

In the post I also looked at the 100+ Indian unicorns created thus far to see what the most popular route is. Here is how the four routes stack up for India’s unicorns!

I have also included links to the supportings on how I arrived at the above estimate in my post.

Link to the piece. Do let me know what you thought of it.

This is in fact part of a longer piece I am working on around ‘the pick’, or the problem space that the founder choses to explore. The commonly used term is startup idea, but ‘the pick’ or problem space, is to my mind is what the founder should work towards.

Readings

Podcasts

Patio11 on the Complex Systems Podcast

Link to podcast episode.

Patrick McKenzie or Patio11 as he is known on twitter runs the Complex Systems podcast. This time he is interviewed. There is a fun passage in this on how he met and impressed his wife Ruriko by singing Beyonce’s ‘Single Ladies’ in front of 200 Japanese folks:)

This passage stood out in particular. Patio11:

“One word is we have the concept of ‘alpha’ in finance, and alpha - one Greek letter smuggles in a huge amount of understanding about how the world works. I would love to be able to describe someone's alpha above the LLM baseline in discussing a topic. Because there are a lot of human writers in the world who have no alpha above the LLM baseline.”

Good mental model (if I can call it that) for how to think about evaluating a person in the AI age. What is their alpha above the LLM baseline? What do they bring to their work a reasonably powerful AIgent can’t deliver?

Dwarkesh Patel AMA on the Dwarkesh Podcast

Link to podcast episode. Link to excerpts from Dwarkesh’s AMA I found interesting.

Dwarkesh Patel’s AMA episode (similar format to the Patio11 podcast episode above where the host is now the interviewee) is an enjoyable listen, covering AI (naturally), his fave history books (Robert Caro’s LBJ biographies), as well as how he selects podcast guests (would be enjoy the 1-2 weeks of research before he interviews them?)

Dwarkesh: “The main thing I took away from those (Robert Caro’s LBJ biographies) books is LBJ had this quote that he would tell his debate [students]. In his early 20s, he taught debate to these poor Mexican students in Texas. And he used to tell them, "If you do everything, you'll win." I think it's an underrated quote. So that's the main thing I took away. And you see it through his entire career, where there's a reasonable amount of effort which goes by 20/80. You do the 20 to get the 80% of the effect. And then if you go beyond that to get, "Oh, no. I'm not just gonna do 20%, I'm gonna just do the whole thing." And there's a level even beyond that, which is an unreasonable use of time. This is going to have no ultimate impact, and still try doing that.”

“If you do everything, you’ll win.” That line gives me goosebumps every time I read it. It is advice for writing or creating, and for life itself.

David Senra on Robert Kierlin, Fastenal on Founders Podcast

Link to podcast episode. Link to excerpts from Senra’s podcast episode I found interesting.

Like most of David Senra’s podcast episodes, this one too is chock full of insight and wisdom. I hadn't heard of Robert Kierlin or Fastenal before this episode. Senra looks at Fastenal through Kerlin’s biography ‘The Power of Fastenal People’. Fascinating episode. The key concept is around keeping a common goal, and organising your company around it - removing everything that distracts from the common goal, and setting incentives and culture to enable everyone to work towards that goal. As with all Senra episodes, he uses the themes in the biography he is covering as a springboard to jump to learnings across several other biographies as well, such as Mike Bloomberg’s biography, from where he comes with the terrific “Do not make the mistake of confusing your product for the device that delivers it.”

Senra: “The one he repeats most throughout the entire book, that your company should be organized and oriented around a commitment to a common goal, and this is their common goal, growth through customer service.

And so what is the uncommon pursuit of the common goal? Organizations succeed to the extent that all of their members pursue a common goal. This is one of those simple ideas that are so difficult to practice. The greatest danger to the success of the organization is that it starts developing unnecessary subgroups, and these subgroups start pursuing their own goals rather than the common goal of the organization. That is bureaucracies what he's describing

This is from Les Schwab's autobiography. “We have had over the years some people in the office that sometimes think that they are more important than the stores.” “The office serves only one purpose, and that is to serve the stores.

Sam Walton said it very similar, he says, "If you're not supporting the customers or supporting the people that support the customers, then we don't have a need for you in Walmart,” kept it very, very simple.”

Mark Daniel, Digital.xyz, on Infinite Loops w Jim O’Shaughnessy

Link to podcast episode. Link to excerpts from Mark Daniel’s podcast I found interesting.

I had never heard of Mark Daniel, founder of investment firm Digital, before this Infinite Loops podcast with Jim O’Shaugnessy. Some great quotes here. My biggest takeaway was around how people want complex and easy (the best pushup variant, the best translation of a foreign book) instead of simple and hard (just keep doing the simple variant regularly, just get started on the book with any translation) etc.

Mark Daniel: “Like marriage, health, building a business, building a great portfolio. All of those things are quite simple and quite hard. Whenever I find myself trying to over complicate something, it's usually because I know what the answer is. I don't want to accept what the answer is, because it's going to require me to sweat. It is always the guy who's out of shape who's asking about push-up variations in the gym. It's always the guy who can't do one push up, he's like, "But do I put my hands here? And then do I do a jumping push-up? Or do I do underhand?" It's like, "No. Just keep going until you can't anymore" and I think that that tends to be correct in every stream of your life that's worth developing. You just have to do the simple, hard thing 90% of the days each year and then do it for 10 years and then look up and see where you're at, and that tends to work out pretty well. That's really, honestly, the only thing that I've seen work out well. That's not luck driven. “

Kelly Granat, Lone Pine, on Invest Like The Best w Patrick O’Shaugnessy

Link to podcast episode. Link to excerpts from Kelly Granat’s podcast I found interesting.

Kelly Granat, co-CIO of Tiger cub Lone Pine, comes on the Colossus | Invest Like The Best podcast with Patrick O’Shaughnessy to give us a behind the scenes glimpse into how an elite public market investor works. Loved how she detailed

• the difference between how public market investing has changed from when her career began (use of credit card data and expert networks in analysis, the rising importance of third party data in impact on stock prices, the importance of macro etc.).

• how Lone Pine works - surprising amount of candour in detailing the processes. Found the 3-member data team particularly interesting - especially how they join investment meetings and even call out interesting trends and anomalies from the data they are crunching.

Kelly: “When I zoom out and think about starting as a summer intern in the summer of 2001 during business school and then returning full-time to the public markets in 2002, the industry was really different. One, there were a lot more fundamentally oriented, directional, duration-oriented investors who were doing deep research with three, four, five-year time horizons. There were many fewer leveraged pods, and certainly passive wasn't a thing yet.

In addition, when I think about organizational structure and how we did our jobs, most fundamental firms were pretty siloed. You could cover industrials, consumer, or financials, and you were doing that with a peer set of people outside your firm with whom you developed a network over time by sharing meetings and attending conferences. The level of conversation among peers was not as informed because people were operating in sector silos in terms of knowledge, coverage, expertise, and network. In addition, the tools we used to do our jobs were pretty different. You would meet with companies, read filings, attend conferences, and try to conduct proprietary research, but things like credit card data and expert networks—all of the tools we now use to supplement our fundamental research—didn't exist.

At the portfolio level, when I look back—and although I wasn't managing a portfolio at that point—I observed that the tools to consider portfolio construction and risk analytics really did not exist. As a fundamental investor, you were going bottom-up, building a single-stock portfolio and considering how stocks acted in concert through correlations and similar factors. The new behavior feels more like what we call setup dynamics—a function largely of the dissemination of a lot of third-party data. This creates setup dynamics around events, quarters, conferences, investor days, and how those events are previewed based on what third-party data suggests or on the cues provided by sales traders at banks regarding whisper numbers.”

Gili Raanan, Cyberstarts, on Invest Like The Best, w Patrick O’Shaugnessy

Link to podcast. Link to excerpts from the podcast I found interesting.

Cyberstarts is one of the most successful venture capital firms in the world. They do only cybersecurity software investments, and are based in Israel. Their first fund resulted in a 40x return(!) thanks to stakes in firms such as Wiz, Island Security, Fireblocks etc., and across five funds and $700m invested, the portfolio value is $45b, half of the valuations of private cybersecurity companies!

In the episode, Gili talks about the Cyberstarts fund philosophy, and the Sunrise program they use to figure out what problems the founders should go after. The Cyberstarts methodology works differently from traditional venture. Instead of backing teams with existing tech / product going after large markets (the typical way), they identify founders (typically from Israel’s elite cyberwarfare-focused Unit 8200) who spend time talking to CISOs (Chief Information Security Officers) to figure out problems they have and which they can solve for, and only then do they start building. This is the famed Sunrise program.

There has been some controversy about the Sunrise program given that many of the CISOs they interview get carry in Cyberstarts, and the carry can increase if you also purchase the products of Cyberstarts’ portfolio companies. Hmmm. News is that this payments program is now suspended. If we ignore the payments part, then the methodology of understand what the market wants before building is a useful one to keep in mind (compare with Jen Abel’s perspectives on market-first startups hitting PMF faster than product-first startups, though the latter have a far bigger upside).

The other interesting perspective was Gili’s framework of the four personas - the one with the pain, the one with the budget to pay for a solution for the pain, the one with the authority to approve it, and finally the one who will use the product. The more these four converge into one persona, the faster the chances of PMF and success for the startup. Really insightful.

Gili: “And then I learned a very important lesson about the four customer profiles. When you sell a product, you're going to face four personas. The person that has the pain point, the person who has the budget to pay for a solution to solve that, the person that has the authority to decide on the product or solution, and the fourth person is the one who would actually use the product. Now, as a startup, if those four personas map into a single person in real life, that's a mega hit.

And that was the case of Wiz. If those four personas are mapped into four real people, there's one real person that has the problem, one real person that has the budget, one real person that has the authority, and a fourth person that actually uses the product. Don't do that. Go and pivot.

And if you map into two people, that would be a very nice company. If you're mapped into three people, that's borderline. You may or may not want to pursue that. So for Wiz, it was a single person. It was the CISO. The CISO, the Chief Information Security Officer, had the problem and the authority to decide on a cloud security solution. They obviously had the budget and, most importantly, they had the AWS credentials that enabled them to deploy the product. So Wiz was able to do something very unique just because all those four Personas mapped into one real-life person.”

Nabeel Hyatt, Spark Capital, on 20VC w Harry Stebbings

Link to podcast. Link to excerpts from the podcast I found interesting.

Serious venture nerds will find bits and pieces of this episode featuring Nabeel Hyatt, GP at Spark Capital (Twitter, Antropic, Discord etc.) interesting, but on the whole, there is nothing exceptional here. Still what stood out:

• Nabeel’s framework about the three types or lenses of AI startups (adaptation, evolution, revolution)

• his observation about venture moving from the puzzles phase to the mystery phase (inspired by US intelligence operative Gregory Treverton’s maxim)

• Nabeel’s point about misalignment of incentives at the Principal / Junior GP level, where they are driven to deploy fast and get markups.

• A quote that stood out: ”It is hard to optimise for performance when your competitor is optimising for deployment.”

Nabeel: “Greg Treverton uses this phrase of puzzles versus mysteries, which is just like, puzzles are this thing that you can like, use that raw horsepower to solve, and mysteries are, you have to go on the journey. In many ways, like the B2B SaaS blow up of that era was all about like the industrialization of venture capital. It was all about figuring out all of the puzzles needed to hire 100 associates to do all of the work, to figure out exactly the right SaaS metrics, and then grind it all out. And no one has any idea what a model is even going to do in a week. So I don't know how that isn't a mystery. And so I think you have to build a firm with that set of talent.”

I would say the early stages of venture capital, the like real early stages of venture capital, if we're thinking about the beginning of Sequoia and so on, like that was all mysteries, man. Like that wasn't puzzles. And so I think the truth is it may sound incredibly old school, but it's going back to the way things were really done before. It is an artisanal business. There's a reason it's an artisanal business.”

Jen Abel, Jjellyfish, on the Lenny Rachitsky Podcast

Link to podcast. Excerpts from the podcast episode I found interesting here.

I thought this podcast episode where Jen Abel of GTM consulting firm Jjellyfish covers the nuances of founder-led sales was really good. Very very relevant for early stage B2B founders. One point that stood out for me was her pov on how going market-first (understanding the pain points of a market first and then building the product) can take you to PMF (product-market fit) faster vs going product-first, where your leverage the state of the art in tech to build a cool product, and search for a market large enough. That said going product-first offers a more unbounded upside (and downside). Very interesting, and the reason why the Sunrise programme (see the podcast episode on Gili Raanan of Cyberstarts referred to above) succeeds becomes apparent now.

“Jen Abel: Remember that amazing chart you drew where it talked about the length of time it took for product market fit. If you look at the top section where the time to product market fit is consolidated, and you go all the way down to the airtables and the figmas, which a long time to get to product market fit. If you think about the earlier ones, which were, it was like GitHub that had product market fit pretty quickly, then Vanta.

There's this thing in my head and I haven't fully validated it but I'm going to share it with you, which is did they start with the market problem first and then build the product? Because they knew who their market was right off the bat. Versus an airtable and a figma that I think started with a technical insight and then were trying to find their market.

Lenny: I think that's absolutely right. Vanta, the way they approached it, Christina, she was searching for a pain. She was obsessed with talking to everybody about a pain that they needed solved, and then she just built it in spreadsheets. So she started with the market very much so.

Jen: And I think product market fit when you start with the market first, it's accelerated. But I will say this, I think that it's also capped on the upside. Because you're starting with the market versus the airtable and the figma, which started with the technical insight and has uncapped upside. But one is certainly riskier than the other.

Starting with a product is a hell of a lot riskier. And this is where I come back to so many people will say, how did you get funding and not know who your market is? And it's like, because if they do find it, that's a really, really, really big win. Versus I think if you start with the market first, you could potentially get a good win but is it more capped?”

Brandon Sanderson, on the Tim Ferris Podcast

Link to podcast. Link to excerpts from the podcast I found interesting.

I haven’t read Brandon Sanderson, and very unlikely to but this was a fascinating chat all the same. What stayed with me

• the two types of (fantasy) fiction writers - gardeners who don’t have every plot element defined prior to writing, and architects, who do (originally suggested by George R R Martin)

• his view of plot as progress (mysteries are where plot progresses in terms of revealing of information); aspiring fiction writers should check out his course lectures

• pros / experienced writers throw out chapters a lot, while amateurs tend not to

• a fascinating passage / discussion on the value of his time, and how an hour spent signing copies makes him $250k and how he has had to set boundaries on things that take him away from writing, like talks.

Tim Ferriss: — because you end up placing so high a per hour value on your time, that every squandered minute is like having a pound of flesh taken and you can drive yourself insane.

Brandon Sanderson: Yeah. I wind in that because if I sign my name, that’s $250 because of the leatherbound. But I don’t want to spend my life signing my name, I want to write the books. But the most money I can earn per hour, I can sign 1,000 of those in an hour and that’s 250 each, which is just an unreal — if you think about that, that’s like — yeah. That’s —

Tim Ferriss: That’s bananas.

Brandon Sanderson: That is bananas. My normal writing time, I can put a different dollar amount. It depends on what I’m writing —

Tim Ferriss: Did you ever get pulled — because it happened to me with speaking engagements, different thing. But did you get pulled away from the creative work or the actual wordsmithing at any point or were you able to hold the line?

Brandon Sanderson: So I was able to hold the line, but barely. At one point, I started to get popular enough that people wanted me on a speaking tour, right? And so, I put a dollar amount on it. I’m like, “Well, at that point, a day of writing,” and it’d take me two days, “a day of writing is 25 grand.” So two days, 50 grand. And we put it up there. Instantly, like 10 inquiries. And I’m like, “I don’t want to do that.”

David Senra on 400 pages of Warren Buffett, Charlie Munger in their own words, in Founders Podcast

Link to podcast. Link to excerpts from the podcast I found interesting.

There were three ideas or concepts that stood out for me from this episode. The first was on designing an organization or career or an investing strategy that plays to your particular strengths and how you like to spend your time. He gives the examples of Michael Dell, and Warren Buffett. Figure out your strengths and stay around that. The next is on incentive design, and how not to reward short-term / profitability metrics - good illustration of how profitability incentives encourage managers to cut brand spends (the long-term important but not today’s essential) and how that impacts the long-term sustainability of the brand. Finally, there is a wonderful passage on how there are only one-two or perhaps one metric that matters - in the case of Coca-Cola all that mattered was whether daily servings would grow globally. If you believed it did, you knew you could continue holding or topping up your investment.

Senra: "In business we often find that the winning system goes almost ridiculously far in maximizing and or minimizing one or few variables." Sam Zell says the same thing. What they say about Sam is what Sam said about Jay Pritzker.

Jay Pritzker was his mentor when Sam was a very young man. I think he was still in his 20s when he met Pritzker. He said that Pritzker was the greatest financial mind of anybody he ever met. Sam would bring him a deal or they would talk about buying a business, and he'd say, "Okay, here's a list of eight things or seven things that we need to worry about." And Pritzker would respond, "Bullshit. That's the one thing. There's only one variable. And if you solve for that variable, the deal will work out."

They're talking about how if you went back in 1919, you could have bought a share of Coca-Cola for 40 bucks. And in between that time, it dropped by 50% multiple times. There was World War II, there were pandemics, there was the invention of the atomic bomb. And really the only important thing was how many servings of Coca-Cola were going to be served every day many years into the future. So you think about what is the most important factor. That's what Jay Pritzker taught Sam Zell. That's what Sam Zell taught other people.

And that's what they're saying here. Wars be damned. Economic or financial crisis be damned. If I'm buying the stock for the long term—and I forgot how long they may have been holding this, perhaps three decades—are they going to be serving more Coke on a daily basis in the future? All that mattered was by 1998 they were selling 1 billion servings a day. And Buffett makes the point here: "The person that can make people a little happier a billion times a day around the globe ought to make a few bucks doing it."

"If you developed a view on any other subject in any other way that forestalled you on acting on that which is most important, the specific narrow view about the future of the company, you would have missed a great ride."

Neil Mehta on Invest Like The Best w Patrick O’Shaugnessy

Link to podcast. Excerpts from the podcast I found interesting here.

This is the companion podcast episode for the article on Neil Mehta reviewed below. This is the better of the two, though much cover similar ground. Notable for Neil Mehta / Greenoaks’ focus on identifying the 10-15 best founders that matter, building products offering ‘jaw-dropping customer experiences’, and overpreparing for their meetings, and getting answers to the question: “Are your best days ahead of you or behind you?”.

This below quote on Korean ecom co Coupang’s founder Bom Kim’s ability to focus on the single most important at the startup at the time, was very interesting to read. I like to use the term Herbie for the single most important thing (SMIT) or chokepoint at a time in the startup’s or project’s life. I encountered the concept in a Mike Maples podcast, who got it via The Goal. In the book, The Goal by Eli Goldratt, Herbie was the fat kid setting the speed of the group trek. It was only by speeding Herbie that you could increase the speed of the group. Herbie is the rate limiting factor at that point in the startups’ life. Herbies change from time to time in a startup’s life - sometimes it is top of funnel, sometimes it is fundraising, sometimes it is retention. Getting to PMF and eventual success is nothing but the founder sequentially removing these SMITs / Herbies along the startup's journey.

“Neil: It starts with focus. Bom (Kim of Coupang) had this unique ability early on to identify what was the most important thing in the company and focus all his time on that, at the exclusion of everything else. It wouldn't be unusual if you looked at Bom's calendar on a Sunday night, everything the next week, Monday, Tuesday, Wednesday, Thursday, Friday, it would just be blocked out with one single thing he was trying to accomplish.

If it was negotiating cost of goods sold in the diapers division in mid-2014, there'd just be two weeks locked out to just do that for six hours a day, five days a week. And he would just assemble a team and go deep on that and let everything else burn if needed.

That kind of focus is just extremely unusual. People like to say they're focused. They don't really understand what focus means. Focus means saying no to everything else, everything else, at the cost of doing what the single most important thing is. There's two parts to that. It's the ability to prioritize what is most important. You have to practice it to be able to intuitively grok what is most valuable and most important.

And then the ability to maniacally do that at the cost of everything else is an intestinal fortitude that just not a lot of people have. “

Rahul Vohra, Superhuman, on the Lenny Rachitsky Podcast

Link to podcast. Link to excerpts from the podcast I found interesting.

Lots here to chew on in this podcast episode, though the highlight was Rahul’s algorithmic or iterative approach to work towards PMF or Product Market Fit. That said, strictly speaking, in my PMF framework, it is actually PPF or Product to Problem Fit he is iterating towards. The other interesting points were his framework on market widening vs solution deepening, and how startups move from one to the other at different times, how manual onboarding helped Superhuman, and how to set pricing for software (or any other product). Really good.

Rahul: “But to focus on the segment of the somewhat disappointed people, they kind of love your product, but something, and I would wager something small, is holding them back. So you then divide them into two camps, the camp for whom the main benefit of your product resonates and the camp for whom it doesn't. And what do I mean by that?

Well, you go back to the people who really love your product and you basically ask them why. What is it about my products that you really love? In the early days of Superhuman, it would have been speed and keyboard shortcuts and the overall design aesthetic as well as the time that we were saving you.

You then go back to the somewhat disappointed users. And in the superhuman example, I would simply ask, wait, do you like superhuman because of its speed or for something else? And if it's something else, well, and this is hard to do, but politely disregard those people and their feedback.

Because even if you built everything that they asked for, they're still pulling you in a different direction. And the thing that they like the most from your product isn't actually what the people who en masse love it the most for is. So you have then articulated the sub-segment of the sub-segment that it makes sense to pay attention to. “

Articles

‘Letters to a Young Investor #2’, by Kirsten Green, in The Generalist

Link to article.

The last of Kirsten Green’s ‘Letters to a Young Investor’ series in The Generalist. This one covers fund management and org building. The previous letter was reviewed in an previous piece of mine. That was on her investing frameworks.

I found it interesting that they have a head of research as well as a head of data.

Kirsten Green: “This approach has led us to thoughtfully add specialized roles in research, data, portfolio support, and operations. Our Head of Research, Jason, exemplifies the strategic value of dedicated expertise. Given the depth of our proactive efforts to uncover promising tailwinds and business evolutions, we determined it was worthwhile to have a dedicated function that interplays with the investing team's passions and deal flow. The research team ensures we consistently show up with a prepared mind, systematically covering the landscape to build conviction in our ultimate point of view or investment decisions.

This research function acts as both a complementary force and a counterbalance to the natural enthusiasms of investors. When an investor develops a thesis, research helps pressure-test assumptions, identify blind spots, and contextualize the opportunity within broader market shifts. This deliberate tension between passionate advocacy and rigorous scrutiny creates a more complete understanding that strengthens our decision-making. It also means we're rarely starting from scratch when evaluating opportunities – we've often been tracking emerging spaces well before specific deals materialize.

Similarly, our Head of Data, Luke – everyone at Forerunner needs basic data literacy, but Luke brings exponentially greater capabilities that create leverage across everything we do. He can analyze at a depth and context that transforms our decision-making, both in evaluating new investments and supporting portfolio companies through critical inflection points.”

I was reminded of Kelly Granat’s podcast (scroll above) where she describes how Lone Pine has a 3-member data team that supports the investment team, and validates their assumptions, and highlighting interesting patterns from the data they are seeing.

It is not a bad idea, and surprising that more investment teams in venture don’t have this, especially given the data that is beginning to become available via third party data sets, expert calls etc. In fact I am beginning to see expert calls being used in Series A investment evaluations in venture in India now.

‘The Visions of Neil Mehta’ by Jeremy Stern, in Colossus Review

Link to article.

Long read on Greenoaks’s Neil Mehta, who has been a fairly astute picker of high growth (some may call generational) startups such as Coupang, Wiz, Figma etc. Venture nerds will enjoy the colour and back story. That said, I found it a tad hagiographic though. Still a useful read.

Some quotes I particularly enjoyed.

Neil Mehta: “We’re only focused on two things in life: great business models and great founders. When you find them in the same situation at the same time, we go all in.”

Neil: “Each year, Greenoaks identifies about 10–15 people who might be like this, and to whom the firm could be a uniquely close partner. Before any meetings, they set about preparing. “I don’t mean go on the website and use the product a little bit,” Mehta said. “We’ll talk to their customers, examine exactly what competitors are doing, understand the product in a granular way, study the underlying technology and how it’s evolving. There’s a series of things we’re testing for, depending on the company. We can understand from the outside-in better than almost anybody else on Earth. There’s no need to explain the 101 or go through remedial background. For a founder, that makes a first meeting with us feel like a fourth or fifth.”

‘Paradigm Shifts’ by Dom Cooke, in Colossus Review

Link to article.

I loved this passage from the Colossus Review profile of Matt Huang and his crypto venture Paradigm. It captures the typical mindset of the elite VC, obsessed with missing out on the next big venture investment even as s/he quietly notes / celebrates the last success, for you are only as good as your next unicorn.

“At Sequoia, Huang found what he calls “the highest-standards place I’ve ever experienced.” When Facebook acquired WhatsApp for $19 billion on his second day, partners gathered briefly in the lobby. Champagne was poured but left untouched. Within five minutes, everyone had returned to work. Eleven-figure exits faded into the shadows of the firm’s legendary portfolio that includes trillion-dollar businesses like Apple, Google, and Nvidia. The culture demanded excellence in ways that elevated his already considerable ambition.”

‘CEO Explains How He Faked Results in $300 Million Meltdown’ by David Ramli et al, Bloomberg

Link to article (may be paywalled).

Riveting story of how the Indonesia aquaculture startup eFishery’s founder & CEO Gibran Huzaifa inflated his company’s revenues over a six year period, raising $300m+ but finally getting caught out. Its investors thought the revenues were $857m in the first nine months of 2024, but it was actually $172m. Huzaifa cooked the books successfully over a long period of time, but finally it became hard to maintain. That said, he doesn’t come across as a villainous figure as much as someone caught up in events that went out of control. All of us VCs have nightmares about scenarios like this. There is, truthfully, no way of knowing what happens inside a company, short of doing surprise audits, which corrodes the trust battery you have with founders. The best you can do is to avoid putting intense pressure on the founder to keep growing, and to let the founder know that it is not the end of the world if things don’t work out. While that isn’t what led to Huzaifa’s actions here, a key reason (though not the only one) for these frauds are spurred by the founder trying to keep the show going, lest they fall out of favour with investors.

Bye!

It is time to wrap this! As I shared earlier, you should think of this substack as akin to a monthly magazine - you don’t have to read it all in one sitting, and you don’t have to read all of it!

That is all for now folks. Feedback, or your own ruminations, in the comments or at sp@sajithpai.com (Please don’t send pitches or CVs or anything work-related at my personal id; I won’t respond to them at this id; instead please use sp@blume.vc for pitches and any official comms please).

Quick housekeeping announcements for the new subscribers. The newsletter has two permanent sections: Writings - where I usually write and / or refer to one or more original pieces that I published in the previous months, typically about venture or the startup ecosystem, and Readings - about what I read and learnt about. My reading diet is tilted rather heavily in favour of books and podcast transcripts, and against articles / newsletters. This will naturally reflect in the reading list.

This is a long newsletter - think of it as akin to a monthly magazine from me (only the frequency may not be monthly!). I don’t know if you can read this entire newsletter (and peruse the links) in one sitting, and even if you do a second run ( which I very much doubt), you will have to pick and choose what to focus on. A good way to read this newsletter is to certainly read my original writing(s) below, and then glance through the rest and pick 1-2-3 items that pique your interest. Anything more is a bonus!

Writings

1/ Context Collapse

The last issue of this Substack was published in late December. The 3 month gap is largely due to the fact that I (along with my colleagues) was busy with prep work for the 2025 edition of the Indus Valley report, which released late February. There is a fair amount of heavy lifting that happens in the first two months of the year, concentrated in the mid-January to mid-to-late February period, and that means that there isn’t much time for reading or writing stuff outside the scope of the report.

The Indus Valley report has become a much loved and celebrated fixture for the Indian startup ecosystem. Like last year and maybe even the year before, it was accompanied by memes, twitter threads, summaries, and increasingly videos remarking on the takeaways from the report, or just well commenting on the report.

Some of my fave tweets. Not all the tweets below are rah-rah as you will see.

Source: Twitter / X

Source: Twitter / X

Source: Twitter / X

Source: Twitter / X

Source: Twitter / X

Source: Twitter / X

As the last two tweets show, not everyone who tweets about the report is praising it. Some find it too simplistic, and some are puzzled by why a 188-page report with 250+ charts gets so much traffic and reaction on the interwebs, positive or otherwise.

Here I must confess that when we created the report in 2022, to serve as an Indian equivalent of the famed (and now discontinued) Mary Meeker report, I did not anticipate the sheer popularity of the Indus Valley Report, and the varied reactions to each annual issue. We created the report half as a marketing document to sell India and Blume to potential investors (Limited Partners), and half as a chronicle of the exciting Indian startup ecosystem for industry observers. The structure of the report (India and Indus Valley) reflects the dual purpose of the report.

Over the past four years, I have been struck by how much the intended audience has given way to an actual audience of Indus Valley citizens, significantly in Bangalore, largely male, and predominantly in the startup world, using the report to derive trends, ideas, patterns and use AI to parse the report and share their findings with the world on social media.

This year, the report jumped outside the tech bubble and found its way into policy circles, and political discussions. A BBC story with a provocative headline was likely the superspreader event (or spur?) leading to the report moving out of tech circles into the mainstream. Naturally BBC’s story sparked copycat articles in many mainstream publications, and soon, the report got picked by the Indian National Congress party, resulting in tweets from Congress party leaders Jairam Ramesh, Mallikarjun Kharge, Priyanka Gandhi Vadra etc. For the next few days my colleagues and I were a bit tense about the issue spiralling into a political circus. We hadn’t written the report as a critique of any party and we didn’t want the report to become political football. We consulted an ex-Minister, as well a crisis consultant, and even readied a press release in case the issue spiralled. Thankfully the issue died down, but the last two days of February were fairly tense days for me and a few of us at Blume.

What I found interesting was that none of this was picked up in the tech community - by now the Tech community was done with the report and they had moved on to other stuff, at least on twitter [Linkedin picked up the report a week after this:)]. In fact, even most of my colleagues didn't pick this up, for none of them follow any political leaders, and are quite apolitical. Those two days were quite surreal.

Around the time, this was raging, my colleague got a message on Whatsapp saying the report had gone ‘too viral’.

I found the comment amusing in that you can’t control or calibrate virality once it starts spreading. You can’t say “let me make it 66% or just enough viral”. There is no way to tamp down virality, though you can stoke it more if needed a bit through commentary (social boosts) and marketing spends.

The virality of the report post the BBC story, its coverage in mainstream media, and subsequent use in political commentary, is an example of what is termed as context collapse, defined as “where content intended for one audience can reach others, resulting in misinterpretation or negative reactions due to a lack of understanding of the original context” (Perplexity). The tone of writing, the charts, the candour were all designed to be helpful to Indus Valley / founders, but once it went outside this context / universe, it was seen as criticism or casual commentary.

Source: Twitter / X

It is what happens on twitter when a tweet meant for a smaller circle goes viral and reaches folks who are unfamiliar with the issue or nuance. Once this happens, then it is best to delete the tweet. But in our case we couldn’t delete a report, could we?

From context collapse to context capital.

2/ Context Capital

I thought the following passage from Victor Lazarte, Benchmark’s newest partner (on the Venture Unlocked podcast) was fascinating.

“So you're not going to come in and like, just have this crazy insight. So the way we add value is, like, every week you're doing, frankly, like, part of it is this boring work that other people could do. Like you're closing candidates, having conversations with this candidate, explaining to them, why the vision is amazing, why the entrepreneur is great. And you're doing all this work that, frankly, a lot of people could do.

But through that, you're getting a lot of context on the company. And then two or three times a year, the entrepreneur is going to make a very important decision, and he will need a thought partner.

The entrepreneur has two choices. Like, if either they're going to call you and discuss what's going on, or you'll have to call someone else and spend like a couple of hours explaining the context that the person needs to be able to help make the decision.”

And he's going to call you because you're the only one that has context, like you're the only outside person that has context on the company. So in a way, all this work that you do, week in, week out, is kind of like a tax that you pay for when the really important decision comes along”

“You're in this position that, hey, you're able to help the entrepreneur. You're able to be the thought partner that this entrepreneur needs when making that decision. And this compounds very strongly over time. It's like this two or three times a year, you make that decision marginally better.

Like over the 10-year journey that it takes to build a company, like your company is going to be a lot better, right? And your relationship with the entrepreneur will also compound in this way. It's like five years in.”

Victor’s assertion that VCs provide ready context to founders when they work with them closely over a long period, is an interesting parallel to context windows in querying LLMs (that is, the amount of text it can consider and process to arrive at an output). You can think of venture capitalists as providing long, preloaded, (almost) available context windows to their founders through their long interactions with the founder and the company. Reading this passage brought back memories of a past conversation.

A few months back I had to recuse myself from supporting company X due to a conflict with company Y. Company X and Y were both companies I had been supporting from the beginning, but I was more closely associated with company Y. Company Y was exploring something in X’s domain and that was the spur. When I reached out to the founder of Company X, to tell him I have to recuse myself from his co, he was a tad upset and said “I have shared so much with you, and all of Company X is in your head”. At that point I told him will never share anything outside with Company Y and he said but that is not the worry. I was puzzled when we terminated the convo. Now I have understood what he was trying to say. I was deleting all the carefully stored context we had preloaded as prompts in my brain, and was wiping the memory clean.

As seed / early stage investors, this is a real and rare privilege we have - that of holding this context in our heads so our founders can quickly check with us and get our thoughts / reactions. For other privileges read this piece on the seed investor as priest-jester. We need to continuously add to this context and hone it, and be effective stewards. Essentially, good venture is about providing sufficient context capital to our founders.

3/ Capital Thoughts

I recently completed 10 years in Delhi, India’s capital city. Well, strictly speaking, I have lived the last decade in Noida, a satellite city of Delhi, part of the Delhi National Capital Region (NCR), and tightly integrated with Delhi, and so this will do. Neither me, nor my wife, have roots or relations in Delhi or the wider region. So what am I doing here in Delhi?

Well, we moved here in 2015 (after 17 years in Bombay!) primarily for my work. This was to set up Bennett University (as part of The Times of India Group) which had received a license from the Uttar Pradesh government. The most optimal location for the university (keeping in mind variables such as cost of real estate, and proximity to Delhi) was Greater Noida, and thus distance from the university site as well as ready access to good schools for our daughters, meant Noida won over Delhi. So we found a house in one of the gated communities / apartment complexes along the expressway from Noida to Greater Noida and set up home. Coming from dense buzzy Bandra where we had lived much of our Mumbai life to the sprawl of Noida Expressway was a tad disorienting, not to mention the differences in culture, people etc. But we adjusted.

Subsequently after the university launched, following three years in Delhi, I shifted to Blume, but I continued to be based here in Noida / Delhi. Blume wanted to bulk up its presence here; at that time, we only had Arpit Agarwal here, and he was very happy to see the Delhi presence double. Subsequently we added more folks to the team, though gradually they have all left Delhi for Bangalore (including Arpit). I now find myself the sole investing member of the Blume team in Delhi:(

On this topic of relocations, I remember my parents shifting to Delhi in the mid-90s, my dad receiving his mandatory North India posting (he was working in a South Indian bank). They had lived in the South all their life and the shift was initially traumatic for them, though they eventually learnt to adjust (my mum even taking to the Salwar Kameez) both learning toota-foota or broken Hindi, and even enjoyed their stint. But the first year was tough, both struggling with the language, the weather, the expenses etc. In comparison my shift was a breeze. I was shifting to a large well-managed and well-staffed gated community. Then there were all the usual apps - Uber, Urban Company, Google Maps - which made adjusting to the city, and accessing it a breeze. And being economically advantaged (vs my parents) made it easier to pay up, and access better restaurants or services, for if you are willing to pay up, then Delhi is kind to you.

A digression. I remember coming back from B-school to Delhi in the late ‘90s, and surviving on a small allowance from my parents and having to use the crowded bus service to travel around. [If I found it tough, then think of what the women had to endure.] The year after I got my first job, and my in hand income shot up, and life became easier, for I could now use autos (this was pre Uber, pre metro days) and afford slightly better restaurants. At the time I was living in Mumbai which is a far more affordable city than Delhi (outside of rents) and easier to get around thanks to trains. At that income level, Mumbai beat Delhi hands down on every front. But gradually with each passing year, my incomes rose, and when I was visiting Delhi, I was able to use taxis and cars to get around and even better restaurants, and buy at better shops, and slowly Delhi opened up to me.

The higher your income level and the better the places you spend time at in Delhi, the more superior the Delhi experience / package is in contrast with other cities - you meet better-looking people (sorry, Mumbai!), you have better and more interesting conversations (which is largely centred around Finance in Bombay and Tech in Bangalore while Delhi is more eclectic - literature, politics, policy, law, and also business / dhandha), and you have access to better experiences while shopping or being served. Of course I am stereotyping it. And this is my perception.

I remember the time I felt I could move to Delhi. This was 2013 or ‘14. I was working in The Times of India Group and our Delhi guesthouse was in Greater Kailash 1 (GK1) near the M-block market, and one day while walking around the place, seeing the bustling market, the people, the density, etc., I felt it wasn’t too far off the mark to Mumbai. There was now a large modern metro network, and the city seemed interesting as a place to work. I did worry about the perception that the city had of being unsafe for women, given that I would be moving with my wife and young daughters.

It is true that the confluence of office, residences, and retail, along with the high density of population, makes Mumbai far safer than any other city in India (Ahmedabad is another). Delhi in contrast suffers from zoning (office and residential areas are distinct), and low density, which means it is not walk-friendly (and also means it is less safe for women). Over time with restrictions on zoning easing somewhat (or being violated!) and rising density, it meant that there were parts of Delhi which are walkable to an extent. Vast swathes of South, West, and Central Delhi were seen as fairly safe for women, though perception still lingered.

Another digression. This time a story from my early settling in days. I was shifting from Bandra, a tony locality in Mumbai, to Noida. The gated community I was shifting to was part of a developing sector, and the nearest Canara Bank was in a small town adjoining the new sector. When I told the clerk I wanted to shift, she looked at my passbook (this was 2015, remember!) and said seriously “Aap ko account Bandra se Bhangel karna hai?” Yes, Bhangel was the name of the town! I promised myself that if I ever write an autobiography, then ‘Bandra se Bhangel’ would be the name of the chapter covering my Delhi shift and transition!

The 2015 to 2018 years were likely the best years for us in Delhi. I was in Times where my schedule was freer, and the kids were also young. We explored Delhi thoroughly during this phase. In 2018, I joined Blume and life steadily got busier. The elder one got into high school, and that meant with tuitions and exam stress, gradually her schedule also made it difficult to take out time for impromptu trips. Then came COVID, and our Delhi explorations came to a hard stop. Since then I have had a strange kind of existence in Delhi, tantalisingly close to all the interesting events and places, but lack of time, and the difficulty of making all of our schedules work, and then the occasional seasons of COVID shutdowns and pollution making local travel and exploration tough.

PostCOVID, our Delhi office presence also gradually whittled down as colleagues moved on. We recruited three young women to be based in Delhi (one of whom was originally from Delhi), and all three shifted to our Bangalore office, the first chance they got. Specifically in venture / startupland, Bangalore is where the action is and I am not surprised at all. It is also the case that both in perception and very likely in reality, Bangalore is safer for women than Delhi. I have the privilege of being male and being able to sleep in an uber going back home at 10pm in Delhi. No woman can. She will be on a call or have the phone ready to make a call to someone - her mother, her sister, her boyfriend etc. I don’t know if the same holds true in Bangalore - less so is what I have heard.

Over the past few years, as Bangalore’s dominance increased in the startup ecosystem (more below), my travel to Bangalore steadily increased, and I find myself there at least 10 days a month (see below for why). Increasingly, due to travel, a crazy schedule, mostly virtual calls, and relocation of our office to Noida (previously in Delhi), I find myself travelling less and less within the city, and thus interacting less with Delhi / city. It is a pity, for there is so much the city has to offer, in terms of talks, shows, events, but it is hard for me to partake of the feast given my context. I feel sad in a way, but well, that is life!

Over the last six and a half years in venture investing in Delhi, I have seen two clear trends.

1. The gap with Bangalore for non-consumer / non-marketplace has widened. This is even more true when it comes to top-tier teams. Increasingly when operators from a Delhi / NCR based co want to start up, more of them shift to Bangalore and start up. This is especially true if you are younger and / or don't have kids or dependent parents. For consumer brands (D2C brands) and marketplaces, I haven’t seen a significant shift, and Delhi’s share has held and is strong.

2. There has been a significant exodus of Delhi VCs to Bangalore. This has accelerated in the last couple of years. This is true of Mumbai too. In Delhi / NCR’s case it is led by the fact that the top-tier founder gap with Bangalore has widened, and the fact that pollution has been a challenge over the past few years. The extreme weather in Delhi NCR does not help, and the comparative good weather in Bangalore is a draw. Many VCs with young kids, and without any roots in Delhi have made the shift to Bangalore.

So why am I holding on? Well, we will shift too, to Bangalore, once we become empty-nesters. We nearly made the shift in 2020 during COVID, but we finally decided not to because of the disruption that shifting schools would cause to the kids’ lives and friendships. Now that the younger daughter is entering Class XII, we will probably look to shift next year once she leaves for her university. It will be 11 years in Delhi then. While I love Delhi, and will continue to, I don't think I will miss Delhi. It is perhaps time to move on, though the shift is a year away at least.

Living and working in Delhi, and interacting with Delhi founders, and Delhi in general does steel you up a bit. You are a lot pushier; and mentally you have to be a bit more on guard here. There are lots of microaggressions / micronegotiations - sometimes with your cab driver, sometimes with the parking guy, or the security guy, etc. This post by Rohit Krishnan terming it as bilateral negotiations captures it well. He describes life in India but what he says is especially true of Delhi. But over time handling these microaggressions becomes natural. You never show weakness or softness ideally:) My colleague Arpit once mentioned that after two-three years in Bangalore, on his travels to Delhi he was much more discomfited by these microaggressions / micronegotiations than before. I do hope I never lose this comfort with discomfort:) Take me out of Delhi, but don't take the Delhi-ite out of me. Don’t make me too soft!

Readings

Books

I finished four books over the last three months, two of whose notes I am sharing below (The others, I am still digesting). There are two other books in the halfway or unfinished stage. The first is Karthik Muralidharan’s book ‘Accelerating India’s Development’. I hit pause on it, for after three months of continuous readings on macroeconomic issues, I felt I needed a break:) I will revisit it soon. The second is ‘The Gujaratis’ by Salil Tripathi. I am enjoying this, and taking it slow. It is my (somewhat inconsistent) bedtime read, just before I turn the lights off. I get through 3-4 chapters (they are small chapters) a week! Here are my notes on two of the four that got done.

Richer, Wiser, Happier by William Green

Enjoyable read taking a close look at the investing approaches of public market long-only investors such as Mohnish Pabrai, Joel Greenblatt, Howard Marks, Bill Miller, Nick & Zak of Nomad, Charlie Munger and a few lesser known (at least to me) ones such as Tom Gayner, Matthew McLennan, Laura Geritz, Joel Tillinghast etc.

Interesting how their philosophies converge around concentration, patience, truth-seeking etc. Much of this is well-known / found in writeups on other investors as well. Still what stood out to me is an approach for which I use the word subtraction (maybe a fancy word for focus!) - that is eschewing 'riskier' or 'fragile' investments to come up a shorter list of potential stocks that they track and enter when attractive.

Pulak's book also described Nalanda's investment approach as centred around Subtraction. They track 85 stocks (somehow stayed in my mind) which have passed all their filters, and track them for markets like this when the price becomes attractive enough to load up.

Link to my highlights / excerpts from the book, organised by various investor and investment characteristics.

Unreasonable Hospitality by Will Guidara

Enjoyable breezy read covering the inner workings of running an elite restaurant in New York City, its evolution and rise to top-tier status from its previously middling rank, through a philosophy of giving equal status to service alongside food, and especially through elevating service to outrageous over the top levels through an approach the author terms as ‘unreasonable hospitality’.

What stood out to me was the efforts that went into uplifting service standards at the hotel including their obsession with getting everything just right, such as continually adjusting the music and lighting at the restaurant, adjusting it to existing noise levels and sunlight levels respectively (pgs 120-27 capture this well).

Along the same lines, there is a fascinating depiction, possibly my fave part of the book, where they describe the efforts they went to get the food and service right, for the NYT critic’s visit, given the high stakes nature of the paper’s review. They designated one random table every night as the critics’ table and used that for the dress rehearsal. Every night. The effort paid off in lifting the service and cuisine levels resulting in four stars (which only five restaurants in NYC had received). Pgs 175-76 covering this critic’s table effort is a treat.

Link to my notes on the book.

Articles

1/ Making Markets in Time by Abraham Thomas

Link to article. Link to article excerpts I found interesting, as well as my review of the article.

Good read, especially to understand what is behind the rise of ginormous venture funds, or venture banks as they are called such as General Catalyst, Lightspeed, Sequoia, A16Z etc., and what drives their actions.

Abraham Thomas says

“It’s not enough to build a good business per se; you need to build a business that is fundable by downstream investors: in other words, that hits the (arbitrary, but consensus) milestones that downstream investors care about. In this framing, a VC’s core competence is knowing when a company is fundable, not just by themselves, but also by downstream investors. Consequently, 80% of the value-add offered by 80% of VCs is helping companies with downstream funding.

People poking fun at VCs for being consensus are missing the point. You need alignment on stages and on milestones in order to make the transitions work; and you need support from downstream investors to keep the journey going. Without it, the whole ecosystem comes crashing down, to nobody’s benefit.

In venture, contrarian / consensus and right/wrong are not orthogonal axes; being right in multi-stage venture is defined by follow-on rounds and markups — in other words, by becoming part of the consensus. Venture is the Keynesian beauty contest in its purest form.”

2/ Letter to a Young Investor #2: A Consumer Investing Masterclass, by Kirsten Green, Mario Gabriele

Link to article (paywalled). Link to article excerpts I found interesting.

Particularly useful reading if you are a consumertech / consumer brands investor. Kirsten Green is one of the foremost consumer investors out there (Dollar Shave Club, Faire, Oura etc). She says

“There are three frameworks I return to in order to pressure test this: The first is The Consumer Experience - Business Model Test: does the business model itself enhance the product experience, or is it just financial engineering? A great example is Spotify – its subscription model isn’t just about creating revenue predictability; it fundamentally improves the experience by removing ads and enabling offline listening. Compare that to many other subscription-based consumer companies, where the model is in place primarily to benefit the company, not the customer. Similarly, virality is only a durable advantage when it meaningfully strengthens the product. Venmo’s viral loop strengthened its product experience – the more friends that joined, the more useful it became – while some fintechs relied on acquisition incentives that didn’t actually make their product better. If the business model doesn’t make the experience better for the consumer, it’s a red flag.”

“You asked if I strive to ‘live in the future.’ I wouldn’t say that – I focus on understanding the present so clearly that the future becomes inevitable. The most significant changes don’t appear out of nowhere; they build on signals here today. I engage with what’s emerging in a way that’s deliberate rather than reactionary. I’m not constantly testing every new product, but I do immerse myself in new ideas that challenge assumptions or reveal something about where behavior is headed. It’s less about chasing novelty and more about seeing the throughlines that indicate lasting change.”

It is worth noting how similar the above quote (on understanding the present to see the future) is to Matt Cohler’s quote (cited in Ravi Gupta’s podcast above) as well as the one by Victor Lazarte in the Venture Unlocked podcast (see below).

3/ Venture Capital’s Space for Sheep by Trae Stephens

Link to article.

Trae Stephens, Founders Fund, says

“The average investor does not spend all day simply searching for the best new company; they spend all day searching for the best new company in socially approved technology “space.” Twenty years ago, that space was e-commerce, the “dot.com”-ing of brick-and-mortar stores. Fifteen years ago, “social-mobile-local.” Ten years ago, the “sharing economy.” Three years ago, gaming and crypto. Now, it’s artificial intelligence.”

How true. We see this with Quick Commerce right now in India too. The speed with which follow ons happened in Zepto a few months back and Slikk of late (multiple rounds in two months when nothing has fundamentally changed in the business), it is clear that QCom is now the place for ‘socially acceptable’ deployment of capital (a la AI in the west), solving a real (first-world) problem of capital deployment for certain growth investors.

4/ The Rise and Fall of the Hanseatic League by Agree Ahmed

Link to article.

This is such a well-researched portrait of a fascinating entity, the Hanseatic League (late 12th century to 15th century CE), when merchants and city states across the Baltic sea coast and Northern Europe came together for trade, and formed a coalition, to protect and advance its interests. It even acted like how a state acts, such as waging war to protect its interests, even though it was not one. The article is also a great minihistory of Northern Europe in the first half of the last millennium. Interestingly this was written by a founder (of Flowglad, a YC co). I wonder how he found the time!

5/ Innovation, Sea Snails, and the Blind Professor by Alex Telford

Link to article.

A good review of a very interesting book (Nature: An Economic History by Geerat Vermeij, who is a blind scientist) on seeing parallels between evolution and economics / innovation. I find it interesting to read about parallels / analogies between evolution and economics (such as Pulak Prasad’s book), and this article was particularly interesting in that light.

6/ Bollywood’s Fantasy of Control Is Failing Everyone by Takshi Mehta

Link to article.

Good wrap of how high ticket prices and hence reduced visits to theatres, for Hindi films, along with the high prices paid for movies by streaming sites in the COVID / postCOVID era has led to an industry where stars demand absurd prices, but movies struggle to recover their budgets.

7/ Meet the Man Who Can’t Stop Founding Budget Airlines by Roshan Fernandez

Link to article.

“In David Neeleman’s view, competing head-to-head with the industry giants is a losing game. Speaking at a Breeze flight-attendant training session in mid-February, Neeleman wrote two numbers on a whiteboard: 90% and 86%.

The first figure reflected the percentage of routes where Spirit overlaps with other airlines. “They are in bankruptcy,” he said. (Spirit exited chapter 11 bankruptcy protection this month).

The second was the percentage of nonstop routes where Breeze has no competition—a figure that has now ticked up to 87%. “You aren’t just doing what everybody else is doing,” he said in an interview.

The airline reported its first full quarter of operating profit at the end of 2024 and has been growing steadily, now serving 70 cities with more than 280 routes.”

8/ Tyler Cowen, The Man Who Wants to Know Everything by John Phipps

Link to article.

“Cowen calls himself “hyperlexic”. On a good day, he claims to read four or five books. Secretly, I timed him at 30 seconds per page reading a dense tract by Martin Luther. Later, I sat next to him while he went through an economics paper. He read it at the speed of someone checking that the pages were correctly ordered.”

9/ How to Build a Truly Useful AI Product by Chris Pedregal

Link to article. Link to article excerpts I found interesting.

Terrific article by Chris Pedregal, founder of Granola on how to build AI products. Very provocative intro –

“The traditional laws of startup physics — like solving the biggest pain points first or that supporting users gets cheaper at scale—don’t fully apply here. And if your intuitions were trained on regular startup physics, you’ll need to develop some new ones in AI.”

I don’t entirely agree with this but there is some truth that you shouldn’t rush to solve the biggest pain point now (if constantly-improving LLMs remove that pain point you spend a lot of time working on, well, that is a lot of effort gone) but instead focus on enhancing context (which improves the AI-generated output) and the experience (which is not necessarily AI). It is a bit like airlines (don't worry about the 747 or 320) but on what the customer can do with it to get their work done (reach their destination in comfort).

10/ The Prophet of Parking by M Nolan Gray

Link to article.

“Yet by the final accounting, (Prof Donald) Shoup has a strong claim on being the scholar who will have had the greatest impact on your day-to-day life, radically changing how we approach the unglamorous problem of how and where we park our cars—and, in turn, where we can live, how we move about, and the form our cities take.

Shoup exercised unparalleled message discipline. He published his first paper on the topic in 1978 and spent the next half-century writing on little else. Aware of the responsibility of his celebrity, Shoup studiously avoided taking a position on almost any other issue. When protesters and counter-protesters flooded UCLA’s campus in response to the Israel-Palestine conflict, I asked for his take. ‘I’m just wondering where they all parked,’ he replied.

Indeed, Shoup worked hard to make his ideas palatable across the political spectrum. Are you a conservative? People should pay for the services they consume. Are you a progressive? All this unnecessary driving can’t be good for the environment. Are you a libertarian? Clearly, the solution to scarcity is prices and markets. Are you a socialist? Let’s stop privatizing the public realm by turning it into a free parking lot. As a result, the typical shoupista gathering is an oasis of peaceful coexistence.”

Podcasts

1/ Chris Pedregal, founder + CEO at Granola on the Colossus’ Invest Like The Best podcast w Patrick O’Shaughnessy

Link to podcast. Link to podcast excerpts i found interesting.

Yes, the same Chris above, who wrote the terrific piece on how founders should think about building AI products. This podcast is in much the same vein though I found it somewhat less useful than his article!

What stood out to me from the podcast:

• Granola users take v different notes (more like states of mind / people-observations) than old-school note takers who cover facts / data from the convo

• How native AI users provide context (far more) than normie users. Interestingly, in his article he had written about how features enhancing context window (by being able to provide the LLM with more info) results in better AI-generated output and user satisfaction.

• Why AI wrapper / app creators should focus on high frequency use cases where output quality matters – those are safe from cannibalisation by LLMs

• How critical the decision to make Granola a mac app that listened to via the device (as opposed to a bot that joined the call) was, and how that has made the biggest difference

• We are still at the clunky UI stage for AI apps. In the early days of cars, a stick was used for moving the vehicle which was not as easily controllable as a steering wheel. It was also less safe. AI’s steering wheel era is yet to emerge, he says.

2/ Sean Ellis, Growth Consultant, on the Lenny Podcast

Link to podcast. Link to podcast excerpts i found interesting.

Sean Ellis is a marketer turned growth head who now consults (also wrote a book called ‘Hacking Growth’) companies on their growth challenges. He devised the now termed ‘Sean Ellis test’ for figuring out if you have product market fit, though in my view it is best used to determine if you have product to problem fit (the first phase of product market fit). This is a good conversation covering a bunch of topics including how to use the Sean Ellis Test, how to iterate on the score (improve time to value, make sure you are targeting the right customers etc), the importance of activation / onboarding etc. There is lots of good stuff here, especially if you are an early stage founder.

3/ Alok Goyal and Ritesh Banglani of Stellaris Venture Partners on the Neon Podcast w Siddharth Ahluwalia

Link to podcast. Link to podcast excerpts I found interesting.

Stellaris is an early stage venture firm in India, and they just raised their third fund of $300m. They spoke to Siddharth Ahluwalia on the Neon podcast about how the firm operates including their focus on ensuring 90% coverage of investments done in the market, why it is important to avoid or minimise adverse selection in venture, their decision-making process (i liked the concept of a ‘no-objection no’ as opposed to a firm ‘no’), as well as their process around proactive portfolio construction etc. Good podcast for venture nerds.

4/ Zal Billimoria, Refactor, on Venture Unlocked w Samir Kaji

Link to podcast. Link to podcast excerpts i found interesting.

Zal is the first Parsi I have encountered in VC but he is in the U.S.! (Parents moved to US midwest fm India). Zal is a solo VC (no team!) who raises a $50m fund every 3 yrs investing in deeptech. Fun episode for venture nerds who like to mull over portfolio construction math in their free time.

What stood out was how A16Z, Zal’s previous employer, incentivised better behaviour to founders via fines for coming later to founder meetings, as well as tracked founder NPS for individual partners, how Zal manages a one-person firm, how he thinks about portfolio construction etc.

This one point by Zal stood out to me as a significant one –

“…feel free to take as many pitches, even if they’re not in your categories of interest. If you’re just getting started and you’re building out your network, you’re building your reputation, you’re building your reps with founders. There’s nothing better than you having more cycles with founders so that you can actually base your gut instinct for when you actually find those special people. Take those pitch meetings extremely seriously. Be prepared, but understand that obviously 98% of them are probably not going to be fits, but you are building your own worldview as to what types of founders you want to work with. Because if you’re only meeting one or two new companies a week, you’re doing yourself a disservice because you’re not building your own kind of mental capacity for what’s possible and when that special founder comes around.”

5/ Ravi Gupta, Sequoia (prev Instacart, KKR) on the Colossus’ Invest Like The Best podcast w Patrick O’Shaughnessy

Link to podcast. Link to podcast excerpts i found interesting.

Podcast episode spurred by ‘AI or Die’, an article which Ravi wrote that went viral. Interesting podcast that captures how a tier1 Silicon Valley investor thinks about AI, and gives glimpses into the prevalent zeitgeist.

Two interesting points made by Ravi –

• A startup can today build distribution (with an AI product) much much faster than before, and it seems faster than an incumbent can innovate. It is the widest that gap has ever been.

• Ravi:“ If something’s an AI-first product, you probably shouldn’t care that much about the margins of it because it’s going to get so much cheaper to deliver that. Whereas if something’s not an AI-first product, you care a lot about the margins because that is the durable future.”

Three quotes from the podcast, shared by Ravi, that stood out

Matt Cohler, Benchmark: “Our job is not to see the future, it’s to see the present very clearly.”

Coach K, Duke: “I am not a world-class predictor, but I am a world-class reactor.” And he was referring to it as when college basketball changed from people that stay for four years to people that play for one and then go to the NBA. He was “I couldn’t have predicted that that’s the way the rules would go. I didn’t know. But you know what? Once that was the game on the field, I played it extremely well.”

Ravi: “…the Collisons, I don’t remember who said this, but they said they listen with predatory curiosity”.

6/ Tomasz Tunguz, Theory Ventures, on Venture Unlocked

Link to podcast. Link to podcast excerpts i found interesting.

Some interesting quotes from the podcast -

“We are looking for applications of AI in two categories. The first is AI does work that a human cannot do. primarily because of scale. The other category we’re looking for AI is where there are shortages in the labor market. You have three things, toil, really unappealing work, nobody wants to do it.”

“Samir: What in your mind makes a company truly defensible in the world of creating an AI app?

Tomasz: I think it’s workflows. It’s not the technology. And this parallels to the previous wave of SaaS. There’s nothing technically different from Salesforce and an upstart CRM. There’s not. They’re all just databases with web pages on top. And within the world of AI, I think there’s an opportunity to reinvent those workflows because now all of a sudden the work has changed, right? A salesperson can manage many more leads. A marketing person can produce much more content. A lawyer can review many more contracts. And so the workflows themselves have changed. So the defensibility comes from identifying which of those workflows have changed and building the software.…there’s about one and a half trillion dollars worth of software and infrastructure spend today. And if you think about how much a company spends on software, it’s about 5% of revenues on average. AI offers an opportunity to go after labor spend in a pretty meaningful way. And labor spend might be 30 to 40% or more of this company. So if you can grab, I mean, you think about this, the market’s at least eight times as large going with AI.”

7/ Shruti Rajagopalan on Ideas of India

Link to podcast. Link to podcast excerpts I found interesting.

Shruti Rajagopalan who hosts the Ideas of India podcast, did an annual retrospective highlighting the podcasts they did in 2024, with her reflections on it. I like this format which was begun by her celebrated fellow Mercatus podcast host Tyler (link for his retro).

What I found interesting

• Books that Shruti thinks are superuseful to unpack the Indian economy: Arvind Panagariya’s India: The Emerging Giant, Tirthankar Roy & Anand Swamy’s Law and the Economy in India: Before Independence and After, Vijay Kelkar & Ajay Shah’s In Service of the Republic, and Arun Shourie’s Governance

• Too many young PhDs writing too many RCT (Randomised Controlled Trial) papers and not enough big picture macro / development explorations. This is led by the present incentive architecture of getting your paper into the big 5/10 journals, she says.

• Under-researched topics in Economics today: Immigration / Migration within India (some of the internal state to state flows are bigger than many country flows she says), Trade, Air Pollution.

• She is rethinking how much education alone can impact lifetime earnings (especially those coming from disadvantaged backgrounds). Family background matters a lot (Jim Heckman’s research has been an influence)

8/ Ben Hunt, Epsilon Theory, on Capital Allocators Podcast

Link to podcast. Link to podcast excerpts I found interesting.

Ben Hunt (@epsilontheory on Twitter) is a Political Science PhD who transitioned into investing. Interesting thinker. The big theme in his work is on narrative crafting, such as how a government shapes the nation’s mood to go to war, or how a stock is positioned as an up and coming one via a narrative.

What I found interesting

• There are two kinds of stories / narratives in investing – one to explain why something happened, the other to upsell or sell something (related – see Kevin Kwok’s Narrative Distillation)

• Two questions to ask: ‘what is your best guess’ and ‘how sure are you’. Not enough focus on the second he says quoting his mentor Gary King. Remember reading (Stanley Druckenmiller perhaps) that picking alone is not enough, and you need to size your bets too. In that regard, how sure are you matters. That determines how big and deep you can go.

• Keynesian beauty contest. Interesting mental model that Ben refers to. To think of this in venture terms, where a seed investor invests in a firm over another because he thinks Series A firms will think it is attractive. Remember this came up in Abraham Thomas’ article too. It was in Ben Hunt’s podcast that I came across the concept / mental model first, and it now has a permanent place in my mental model armoury.

9/ Russell Napier interview in Swiss newspaper NZZ

Link to article. Link to my highlights.

Russell Napier is an independent macro analyst, and author. This was a very interesting interview – one that really is perspective shifting. He says we are entering an era of national capitalism, where the government will (akin to how China works) have a say in capital flows and where they are directed to. He says the monetary system is shifting to a new phase, where governments will inflate away debt. He recommends shifting away from debt and S&P500 and looking at equity that could benefit from the capex wave.

10/ Alan Taylor, Historian, on Conversations with Tyler

Link to podcast.

Thanks to the Conversations with Tyler retro, I learnt about and read the transcript for his podcast episode with historian Alan Taylor. Enjoyable one that. Alan Taylor knows his field (US Revolutionary War and 18-19th century North American history) really well, and that came through. There is a 2 page segment where he talks about how he is seeing dropping interest from students for history, primarily due to the declining prospects for employment – reduced tenure track roles, limited openings in Industry for historians in contrast with say Economics students etc.) Even as demand for academic history declines, we are seeing a huge demand for popular history, especially podcasts like ‘The Rest is History’ / Hardcore History etc. This Bloomberg piece captures the rise of the history podcast.

11/ Jake Saper, Emergence, on 20VC

Link to podcast. Link to podcast excerpts I found interesting.

I thought this Jake Saper convo w Harry Stebbings on the 20VC podcast was v good. Jake is a GP at Emergence Capital, who exclusively do B2B investing (Salesforce, Veeva, Zoom, Gusto etc) and have a crazy track record (1 out of 5 investments have become unicorns!).

2 interesting points stood out particularly

• One they have an arrangement where all the partners work on a potential transaction such as doing refchecks, diligence, and not just the deal team as is with most funds.

• Second, fun story about how he was made to run the gauntlet to win the right to invest in Assembled. As I have shared before, in top tier startups, the founder picks the VC s/he wants to work with, not the other way around.

12 / Victor Lazarte, Benchmark on Venture Unlocked w Samir Kaji

Link to podcast. Link to podcast excerpts I found interesting,

Short and sweet podcast featuring Benchmark’s newest Partner. Nothing terribly new on the co for venture nerds / Benchmark watchers. Two interesting passages though -

• I covered this in my writing above as well) The first was on how one of the most valuable ways VCs can help founders is gaining context on the co and holding the entire company, its business model, its strategy, team dynamics, evolution etc., in their heads so founders can quickly get their reaction to a decision instead of having to explain all the context and spend time. VC as a long and preloaded context window is an interesting spin.

• The second was around evaluating high growth AI companies, especially around durability of revenue. A good question to determine whether it is curiosity or real revenue is to ask if models get 10 times better, is this a better business or a worse business? Such a good question.

13/ Tyler Cowen on How I Write w David Perell

Link to podcast. Link to podcast excerpts i found interesting.

Tyler covers what kind of writing is AI-proof (writing that is more personal, memoirs, biographies where you are talking to people), how to use LLMs (provide waaay more context), and which LLMs to use for what (DeepSeek for evocative writing with higher hallucination risks, Gemini for legal etc.), the potential for AI to create books on the fly (like biographies), like how Demand Media / eHow would create pages on the fly (I think) to match google search queries.

14 / Avnish Bajaj, Z47, on the Neon podcast w Siddharth Ahluwalia

Link to podcast. Link to podcast excerpts i found interesting.

Good podcast for venture nerds, and especially those working in the Indian venture ecosystem. A glimpse into how a Tier 1 venture firm operates including the processes at work, and a peek into Avnish Bajaj’s brain. What I found interesting was the sheer number of frameworks and internal monikers that popped up - Glaring Error Bucket, 2P or 2nd pair of eyes, Pass With Conviction, Met Culture. Just like Stellaris (also covered in a Neon podcast above), Z47 too is a strong process-oriented firm with a strong focus on exhaustive coverage, i.e., making sure they don’t miss out on good / great founders.

15 / Dan Cable on Play to Potential Podcast w Deepak Jayaraman

Link to podcast. Link to podcast excerpts i found interesting.

Dan Cable is a professor of Organizational Behaviour at LBS. He has written a book called ‘Exceptional’ where he describes how we can use feedback and memories from people who have seen us in our past lives and avatar when we were exceptional or did something exceptional, to point to what actions we can undertake to become our best selves. This is a podcast in the leadership and psychology space, I enjoy listening to, but I don't often get to. If you like stuff like this, then do check out Deepak Jayaraman’s book ‘Play to Potential’ as well.

Dan Cable says

“I have learned a lot about how surprised people are when they get one of these highlights reels. And basically what that is, it is memories and stories from family, from friends, from colleagues, from mentors, it is people that have watched you over the years, even over the decades. And then they write a story that is their memory of a time you have done something exceptional, that is name of a book, that is why that book is called Exceptional, there are times when you have had an extraordinary impact and here is my memory of you doing that….that highlight reel starts to unveil ways of you becoming exceptional and I call them high leverage moves. It is just a way that you can do a little more in area and create a much bigger impact but you would not do it because you kind of downplay, you think anybody would do it. “

Bye!

It is time to wrap this! It is really really long, and perhaps the longest newsletter I have written. [One of my goals for the next few months, is to try and experiment with formats that lead to shorter and more frequent newsletters!] As I shared earlier, you should think of this substack as akin to a monthly magazine - you don’t have to read it all in one sitting, and you don’t have to read all of it!

That is all for now folks. Feedback, or your own ruminations, in the comments or at sp@sajithpai.com (Please don’t send pitches or CVs or anything work-related at my personal id; I won’t respond to them at this id; instead please use sp@blume.vc for pitches and any official comms please).

But before that a short take on the year it has been. Two common strands or themes to the year across all my identities (work, writing, family). First, it was the year that things didnt come to pass:) Second, it was the year of inputs, and investing in, and not the year of outputs or harvesting.

For instance, on the work front, I expected a portfolio closure or even two, but both survived the year, and may survive longer too. I haven’t got the decisive uprounds and wins I expected from my portfolio in 2024. If 2021 was the year when investors loved you even though your customers didn’t, then 2024 was the reverse. But the progress the companies made was impressive. There has also been incredible evolution on the founder front for a few, especially Classplus. Watch out for them. All of this makes me cautiously (after this year’s disappointment) optimistic for 2025.

There has been considerable evolution in my thinking as an investor as well. It is six years now as an investor, a new identity that I adopted when I joined Blume in 2018. It was a strange world, and I adopted myself the best I could. After six years of experimenting, sometimes succeeding, sometimes failing, and continuous learning, I am beginning to arrive at my style of investing, one that takes into account my strengths, and patterns of habit, while fitting into the house style. If you are familiar with Robert Kegan’s five stages of adult development framework, I have moved from the socialized to the self-authoring phase. Or if you prefer Graham Duncan’s five levels of the investing game, then I moved from the expert to the professional level.

On the writing front, there has been some progress towards the book on PMF (product-market fit). I hope to start releasing the first two parts of the book online this summer. Hopefully by 2026 summer, the entire book should be online. Because the book sucked up a lot of my writing energies, there weren’t enough articles, short or long-form from me this year. That trend won’t change I think sadly, but hopefully there will be enough to read in the multi-chapter parts I will release online summer onwards.

On to the recommendations, and my notes on them.

Books

I read 22 books this year, of which three were works of fiction. Now I have kept stats of what I have read over the past two decades; I average 23 books a year, about a quarter of which are fiction. Two goals I have set for myself a few years back is to read more fiction, and read older books. On both counts I failed this year. Far too works of fiction, and too many recent reads.

From the 22 books I read this year, I have listed about 10 here, which I particularly enjoyed or recommend.

The first five below are the ones I recommend highly, and then the next five round out the list. There is no particular order in each quintet.

1/ How Big Things Get Done (2023) – Bent Flyvbjerg & Dan Gardner

Bent Flyvbjerg is an expert on megaprojects and why most megaprojects are delayed and overbudget (only 0.5% of megaprojects are under budget and on time he says). In this book, he covers why most megaprojects ‘fail’ and how you can get them done in time and under budget. The mantra is ‘think slow, act fast’, i.e., take your time getting the plan right, and move furiously to execute. Good easy read with lots of interesting examples. Could have been much shorter though, as with all business books.

My summary of the book is here.

2/ Court on Trial (2023) – Aparna Chandra, Sital Kalantry, and William H.J. Hubbard

Compact and enjoyable book reviewing the (mis)functioning of the Indian Supreme Court, through data. Highly recommended. It is surprising it hasn’t created the kind of noise it deserves to, given the topic it deals with and conclusions it derives.

The book was fascinating and infuriating in equal measures. Fascinating, because to a legal layman like me, it opened up the world of the Indian Supreme Court, and the challenges the court faces (the large number of cases, the pendency / delays, the power of the senior advocates, the lack of diversity on the court etc.). Infuriating, seeing the Supreme Court riddled with challenges which it has brought upon itself. The book lays out the challenges the Indian Supreme Court is grappling with, not through anecdotes (though there are some of those in the book) but through data which is not easy to come by, and was painstakingly assembled.

Through this data, the authors come to conclusions such as the Court, in trying to be a ‘People’s Court’, takes on too many cases, and often unimportant ones at that. Most of these cases are of a kind known as SLPs (Special Leave Petition, a provision which was only meant to be used sparingly, but accounts for a bulk of the workload of the court). The court admits a sixth of the ~60k cases it is petitioned (far too much), with SLPs accounting for 88% of these, and passes judgement in ~1k of those. (In contrast, US Supreme Court admits 1% of the ~8k cases it is appealed). Because of the lack of time to deal with the ~10k cases it admits, the ~1k judgements it passes often do not cite legal precedent, give limited guidances to the lower courts, and thus often cannot be used for future judgements.

In different chapters, the authors cover different misfunctioning facets of the court including how the large number of SLPs lead to admission hearings on mondays and fridays, where the ‘elite senior’ advocates get facetime of 90 seconds per case, and charge anywhere from 1L to 15L per appearance. Many of these hearings are influenced by the signaling power (or ‘face value’) of the Senior Advocates. It looks at how the power shifted from judges to senior advocates and asks what can be done to redress that.

Subsequent chapters look at topics such as diversity, political influence, the power of the Chief Justice in determining which judge is assigned to which case, etc. All of these are analysed, and conclusions are drawn through the use of data. Despite all of the legal arcana, the book was an easy read, even for a legal layman like me. It is also a relatively slim read (around 200 pages). Recommended read.

3/ Write Useful Books (2021) – Rob Fitzpatrick

A short and highly readable guide to writing the non-fiction book that dispenses actionable advice, and helps readers achieve their outcomes (books like The Lean Startup, Building a Second Brain etc., which the authors calls ‘Problem-solvers’) as opposed to non-fiction works that are edutainment products such as Malcolm Gladwell or Steven Johnson’s books (which he calls ‘Pleasure-givers’).

Writing a ‘Problem-solver’ needs to be approached very differently, says the author, noting that much of the advice that is usually dispensed for non-fiction books is for ‘Pleasure-givers’. For one, you need to define the scope and the audience tightly enough that there is a strong promise (it is hence ‘Desirable’), it needs to deliver on the promise by offering a high degree of value (‘Effective’), the reader should not have to work very hard to extract that value (‘Engaging’) and finally it needs to be aesthetically designed and well-produced (‘Polished’). ‘Desirable’, ‘Effective’, ‘Engaging’ and ‘Polished’ add to the acronym DEEP, which is a handy way to remember the attributes of a successful ‘Problem-solver’.

Such a DEEP work, he says, will become a self-recommending title, because it is actionable and useful for anyone faced with the problem the book has solutions for. The author shares a lot of useful tips to create self-recommending titles, such as 1) a descriptive Table of Contents, with each chapter’s description being the benefit or value the reader gets from reading the chapter 2) front-loading the value – quickly getting to the meaty parts / main course instead of forcing the reader to consume a lot of starters or front matter 3) having ‘listening’ and ‘teaching conversation’ with prospective readers to validate the Table of Contents, and some key chapters 4) striving for high value per pages turned – reviewing the pages per value or benefits offered, and so on 5) Beta-testing the book with a select group of readers you recruit 6) a guide to self-publish and market the book 7) how to decide on the cover page, and so on. All in all, a useful read for anyone looking to write a ‘problem-solver’.

4/ Lilliput Land (2023) – Rama Bijapurkar

One of the best books I read this year. The book looks at India through the trifecta of its socio-economic-demographic structure, the Indian consumer’s behaviour, and finally the supply structure catering to demand. It says that despite the Indian consumer’s adaptability and their rising aspiration (behaviour), the growth of the economy is held back by a) high inequality and low disposable income for a vast majority of Indians (which is reflected in the socio-economic structure), and b) despite the clear demand for high value, affordable products, the inability of supply structures to cater to this demand (barring a few Indian company, a few Chinese and ecom companies).

The nature of India’s demand – large overall, but aggregated by the small spends of masses (hence the title ‘Lilliput Land’) – means that companies interested in catering to mass India, will need to create ‘Made for India’ products that reflect this reality, providing affordable value to consumers, taking advantage of their high digital awareness and rising aspirations.

5/ The Mom Test (2016) – Rob Fitzpatrick

This is the second book of Rob’s in my shortlist! This is the single best resource for conducting customer conversations better, especially during the problem validation phase of a startup (before you build the product). It is a short book, and the time of 3-4 hours invested in reading it is well worth it in terms of impact.

The name ‘Mom Test’ comes from asking questions in such a manner that even your mom can’t lie to you, because your mom will always think whatever you tell her is a great idea, and respond effusively. Hence your questions need to pass ‘the mom test’! The book encourages you to ask questions about your customers’ lives – “their problems, cares, constraints, and goals” and use these “concrete facts about our customer’s lives” to “take your own visionary leap to a solution”.

The book says that the later you mention your idea to the customer you are interviewing, and even better if you don’t mention your idea, the better the questions you will ask, and the more insights you will extract from the conversation. The book puts it well: “It boils down to this: you aren’t allowed to tell them what their problem is, and in return, they aren’t allowed to tell you what to build. They own the problem, you own the solution.”

My notes / highlights of the book is here.

6/ Accidental Empires (1992) – Robert X Cringely (Mark Stephens)

Fun, racy, spicy, ultra-gossipy read of the history of Silicon Valley, and the shenanigans of the computer pioneers (Bill Gates, Steve Jobs etc) from the 1970s-80s. That said, it goes beyond gossip and funny anecdotes to cover the shifting technological trends and business dynamics of the industry as well. There is also a deep dive into the culture of then startups Microsoft, Adobe, Apple, Lotus etc., as well as behemoth IBM (the best one). Its ability to mix and cover tech trends, business strategy, as well as bad boy behaviour, equally well made it an enjoyable and interesting read for me.

The book became notorious when it was first released in 1992 (apparently Microsoft tried to get it banned) because it mentioned stuff like Bill Gates not showering regularly, and drunk-bitching about IBM in a meeting with Lotus executives (which found its way to IBM). Should you read it? Well, if you have a deep interest in Silicon Valley history like I do, go for it. If you don’t, then strictly don’t bother, though if you do, you won’t be disappointed!

7/ The Rise of Asian Paints (2024) – Anupam Gupta

Well-written chronicle of the birth and rise of Asian Paints, as well as its ‘first among equals’ cofounder Champaklal Choksey. From what i could make out basis the book, Asian Paints’s growth is a classic compounding play, benefitting from the steady growth of the Indian economy as well as the ’70s FERA diktats that kneecapped its foreign-owned rivals.

It ran a tight operational ship and took a set of bold decisions, such as investing in R&D / product development by hiring chemistry experts, bringing in professionals to run key aspects of the

business (first family business to hire from IIMs in a big way, investing in tech (first non IT co to invest in a computer in early 70s), going direct to retailers bypassing distibutors, investing in brand marketing etc.

8/ Breaking the Mould (2023) – Raghuram Rajan & Rohit Lamba

A cautious, or even a mildly negative take on the Indian economy and the recent policy directions. In particular I enjoyed reading the authors’ take on why the PLI (production linked incentive) is an expensive mistake. Along with the analysis of recent policy missteps it also tries to lay out recommendations to set the economy on the right course.

9/ India is Broken (2023) – Ashoka Mody

Good breezy read on India’s economic history since 1947 with a deep dive and discussion of its economic failings. Skewers both the Congress and the BJP. Much like ‘Breaking the Mould’, recommended if you like to read books written from a macroeconomic perspective on India.

10/ Beyond Market Value (2019) – Annette Campbell-White

Interesting though ultimately a slightly disappointing read. It could have been so much more I felt this book, an autobiography by a venture capital investor and rare book collector. I was expecting an equal weightage to both topics, but sadly it is a bit weighted in favour of book collecting. As a female investment banker-turned venture investor, and as one of the few female VCs in her time, a detailed and comprehensive narrative of her career and investing experiences would have been fascinating to read. In fact we do get a few glimpses of this but they are too few and far between.There is far too much space given to books and book-collecting, and while there are some amusing anecdotes, sadly much of it is not as interesting as the venture part. Yes, your mileage may vary, depending on your interests. That said I have reasonable interest in both and yet, I felt the book collecting part overwhelmed the venture part, leading ultimately to a book that is not as intriguing as the cover and premise suggests. Still given the topic and the author’s candour, I felt this was worth an inclusion.

Podcasts

Podcasts are having their moment today, given the outsized role they had in the US 2024 Presidential election. It is impressive how some of the larger ones, such as the Joe Rogan Experience, have emerged as counterweights to mainstream media. While podcasts have hit the cultural zeitgeist and have broken into the mainstream, they have always had an outsized influence In our own little (well, no longer little) tech + startups + venture world.

A key reason for that is that podcasts are likely the least frictionless way for tacit information or tradecraft to be made more explicit in the tech world, given the opportunity costs of time for a founder or VC. Hence they offer the highest information bang for the time buck as far as the tech + startup world goes (see my old piece ‘Why Podcasts Matter’). Kinda like how biographies / autobiographies are to the world of non-fiction.

As I became aware of the advantage podcasts offered, I reformatted my information diet to prioritise podcasts, consuming it mostly in the form of transcripts (Apple Podcasts’ autogeneration of transcripts has been a gamechanger of late). I reduced my consumption of articles and newsletters, unsubscribing from most newsletters, or autoarchiving them, barring a handful of paid subscriptions (Lenny, Generalist, Newcomer etc.) I described it once to an acquaintance as the equivalent of an information keto diet, eschewing information carbs (articles, twitter) in favour of proteins (podcasts) and fats (books)!

Here is the list of podcasts I consumed and enjoyed, in 2024. Not all the podcasts are those released in 2024 (though most are).

1/ Acquired – Hermes

Link to podcast + transcript.

Excellent episode, where the hosts Ben Gilbert and David Rosenthal dig deep into the Hermes history as well as their manufacturing process, with lots of fun facts sprinkled across such as how they never openly reveal their highest-selling and most prestigious products, the Birkin and Kelly bags. Overall an excellent episode to listen to, and one of the many that have come on luxury brands such as on Ferrari, Rolex and Patek (these three in Colossus’ Business Breakdowns; the Rolex one in particular was v good). Common to all is that you cant just walk into a store and walk out with a purchase. Often the one you want will not be available or you will be told the ones in stores was reserved for a specific buyer. Purchase of choice products like the Birkin is subject to you building a track record or purchase history over time and spending lots of money on what you really don’t need before you get to buy what you want:)

2/ Turpentine VC – Sarah Tavel + Eric Vishria, Benchmark

Link to podcast. Link to transcript (organised by me).

Benchmark is such an interesting firm, given the strategic choices they made around the equal partnership, and working without any support (no analysts / associates, just an occasional Principal, and no platform team). In this episode, there are interesting discussions of the implications of these choices and tradeoffs. The bad is that this can mean insufficient coverage (not enough cold bodies to email) or support to founder, but the good is that it is a forcing function to focus on what is truly important, which is direct time to the founder on key inflection points, and build greater and better context about the business which informs future decisions. There is also an interesting section on how they think about future Partners and recruit them. Benchmark is a one of a kind firm. It is very unlikely there will be too many more like it, so it is unlikely any of their strategic choices will fit those of other firms, but it is fascinating to see the entire set of choices and tradeoffs, and how they make for a firm like them, and the implications of these choices.

3/ Colossus | Invest Like the Best – Gavin Baker, Atreides

Link to podcast + transcript. Excerpts from the podcast that I found interesting here.

This was an astounding episode. Gavin Baker is clearly amongst the most knowledgeable tech analyst and observers out there, and this episode is an excellent one to get his perspectives on the AI landscape.

The section on how the explains that GPU advances alone are not enough to understand the power of a data centre was riveting. What matters he says is MFU of the GPU, where MFU = model FLOPS utilization. He then teases apart MFU into MAMMF (maximum achievable matrix multiplication flops, or software on chipset efficiency) x SFU (system FLOPS efficiency, essentially networking, storage, and memory efficiency). His key thesis is that the networking tech and improvements havent kept pace with GPU improvements and are rate limiting GPU advances from being utilised. A large segment is his perspectives on AI, which I can’t say I understood it entirely, but it gives you a drone level view which is extremely useful. There is other interesting stuff as well such as the segment on how Elon, Jensen Huang, work – only on the most important problems, and like to hear bad news first. Jensen: “I have no fixed schedule. I have no standing meetings. I just find out what is the most important problem at the company, and I go, and I sit my desk out in that area, and I pull the best resources to work on that problem, and I love it.”

4 / Lenny’s Podcast – Eli Schwartz, SEO guru

Link to podcast + transcript.

Long episode at nearly 2 hours, but worth a watch for any founder / operator wrestling with SEO or content. Eli Schwartz is one of the foremost thinkers in the SEO space today, author of the book ‘Product-Led SEO’ and advisor to Zapier, Tinder, LinkedIn etc. He speaks to Lenny on a wide range of topics related to SEO.

2 key themes in the podcast that stood out to me:

• Eli covers how AI / LLMs will impact search / SEO. Effectively the top of the funnel will now be owned by Google and LLMs – so content like 20 best beach hotels in Southern Europe will now either get aggregated into AI Overviews (top hit on Google Search) or within LLMs with occasional citations, and your site will get pushed further downward. Hence the best SEO content will move midfunnel and have content that is helpful to drive conversions. This is how SEO should have been from the beginning but because it is hard to measure conversion, and harder with SEO, and relatively easier to show rankings impact, SEO got positioned as Top of Funnel.

• The other metapoint that Eli makes is around whether you need SEO at all. Not everyone has to do SEO he says. It is best used in contexts where the customer is aware of the problem, uses specific keywords or language to understand the problem or look for a solution, and this behaviour arises naturally in the user / customer journey of addressing the problem. User Journeys is a term which comes frequently in the podcast episode, and effectively Eli is saying that if searching for content is not helpful for the user in solving the problem / and not relevant for you in driving conversion, then you don’t need SEO. Too many companies default to doing SEO because yi have raised money and you need to spend on SEO. This is wrong he says. It is expensive when you add up all of the cost of creating the content and hiring the experts. You need to consider the ROI of the investment actively like you do with Paid Marketing, but not enough companies do that he says. In his perspective, most sales-led / top-down SaaS motions can eschew their investments in SEO. It is more relevant for PLG motions like Zapier, Notion etc.

5/ 20VC – Alain de Botton

Link to episode page. Link to my notes + highlights of the episode.

I thought this was an exceptional episode. Alain De Botton is an intriguing guest for a tech podcast, but I am glad Harry did it and was able to pull it off. I read Alain De Botton’s romantic novels when I was in my 20s and enjoyed them hugely. Later he evolved into a (pop) philosopher of a kind and I kind of lost touch with his writing. I am now tempted to dip into his philosophical writing given this episode. What stands out here is his insight into the psychology of parenting, the parent-child dynamics, and the psychology of the workplace. That one line (see first para in the ‘Advice to parents’ section in my notes page linked above) where he encourages you to praise or esteem your child for what they are vs for what they did, and you will thus give them psychological armour for adulthood, was the biggest takeaway of the episode for me.

6/ AI + I – Matt Cynamon, USV

Link to podcast and transcript. Link to my notes / highlights.

One of the more interesting podcast interviews I have consumed in the past months / year. Matt Cynamon the ‘Head of Library Sciences’ at Union Square Ventures comes on the AI + I podcast with Dan Shipper to talk about all the cool AI stuff they are cooking up at Union Square Ventures (USV). You may have seen the OH (overheard) on the USV Librarian account @usvlibrarian on Twitter. That was built by him. Over 70 mins he takes us through the GenAI stuff they are building at USV, detailing cool tools such as The Librarian (a querying too for all the 15k articles they have written at USV), OH or Overheard (Meeting Notes) and The Dream Machine (v trippy video tool to create AI images to sync with conversation topics).

Am sure some other VC funds have some of these built (Yohei Nakajima comes to mind), but USV is of course one of the giants of venture. Impressed with the suite of tools that USV has built out, and grateful that they and Matt have been more public about it. An interesting point that stood out to me from the episode was Matt’s posit that the cost of creating good storytelling is dropping, and that there is a ton of content getting created that is not getting captured and AI can help you capture and make that content in a ready to consumer format.

7/ Dwarkesh Podcast – Daniel Yergin

Link to podcast + transcript. Excerpts from the podcast that I found interesting here.

Daniel Yergin is an oil / energy expert and author of ‘The Prize’, which is an acclaimed history of oil (and as Dwarkesh says, a parallel history of the 20th century too). I haven’t read the book yet. It is there in my bookshelf somewhere waiting to be read. For now this podcast will do. This is a riveting episode with so many interesting threads and themes. Dwarkesh’s range is incredible – from AI to Oil to Geopolitics and History (do check out his episode with military historian Sarah Paine). He is also able to see parallels between different contexts, like w Kerosene and early AI models, which is fascinating.

For 50 years after oil was discovered its primary use was as Kerosene for lighting. When Edison invented the lightbulb there was a view that Rockefeller’s Standard Oil would go out of business. It was only when the motor car was invented and became popular that gasoline became the primary use of oil. (“In the 19th century gasoline was a waste product. It went for like three cents a gallon.”) Interesting to see if there are parallels w AI, asks Dwarkesh. He says “Currently what we’re using these models for is research and chat and whatever. That’s like the kerosene. What would the equivalent of billions of vehicles look like for AI?”

8/ Ideas of India – Karthik Muralidharan

Link to podcast + transcript.

Enjoyable and interesting episode where Shruti Rajagopalan interviews Karthik Muralidaran, author of the book ‘Accelerating India’s Development’, a prescriptive book where he writes on how specific interventions around improving the quality of expenditure in areas such as healthcare, education can yield dramatically improved outcomes. I am presently reading the book (it is a big one at 800+ pages!). The podcast episode gives you a sense of the contents though. The core message of the book is that too much rhetoric is devoted to what the government should do, while remarkable little is around how it should do it, and that matters because thinking about the how, and interventions around these can generate very high returns for the investment undertaken. I found the discussion on centralisation vs fiscal federalism in the context of India and US respectively utterly interesting. The other interesting theme was around government pay (high) and recruitment (too few) in India and how that limits state capacity. During the course of the podcast, Karthik Muralidharan shares this deeply thought-through ideas such as the Practicum and Empanelment, and interventions around local hiring, as well as hiring a second anganwadi worker etc. A good read / listen for those with an interest in public policy and statecraft, and India, or all of these.

9/ Turpentine VC – Chris Paik, Pace Capital

Link to podcast.

Surprisingly good podcast episode. I encountered Chris Paik first on a Invest Like the Best podcast which was interesting as well, and then again recently when his post ‘The End of Software’ went viral. He is an interesting thinker as you will see from the highlights of this episode. A few points which stood out –

• On Thrive Capital, his previous employer, he mentions how they were always ‘playing offence’, given they were based in NYC, and no one from the Valley had to visit NYC. You were default on a plane.

• Pace Capital’s unfair advantage lies in being early. That is the only way they can compete with the multistage funds. If there is a deck, it is too late, is their internal motto per Chris.

• Bullish on local inference, and applications take advantage of that. Apple has a huge advantage per his thesis. Buy Apple! as he says sometimes the obvious trade is the clever trade (like FAANG and Bitcoin)

• Minimum viable infrastructure is an interesting mental model. There is a minimum technology format or bandwidth needed for a media or software product, like text for twitter, 3G for uber / snapchat, 4G/5G/video for tiktok etc. It explains why Instagram succeeded Twitter, and Snapchat succeeded Instagram, and TikTok succeeded Snapchat. The flow is usually in one direction. The reason we havent had a new consumer co in the past decade is because bandwidth has topped out. Interesting theory and he proposes Livestreaming as a potential new format (suggests Whatnot as a likely winner). Some of this thinking also appears in the Invest Like The Best podcast I mentioned.

• Don’t miss out his cute parable of the Three Brothers and why local inference (and Apple) has a huge advantage).

10 / Lenny’s Podcast – Mike Maples, Jr.

Link to podcast + transcript. Excerpts from the podcast that I found interesting here.

I have always enjoyed Mike Maples’s podcasts. He is a differentiated thinker, and backed by a terrific track record. These days Mike has been on a podcast tour, as he is promoting his book Pattern Breakers, which is about the success patterns or themes underlying successful startups. The title comes from his quote that “The way a startup wins is they deny the premise of the rules and propose something completely different. They radically break the pattern and can’t be compared to anything which came before.” The book’s basically broken up into two parts, how to come up with an idea and then the actions you need to get right to move forward an idea. In this podcast with Lenny, he covers the key themes of the book. It is worth a listen / read. I particularly enjoyed this riff on how startups can storytell better, especially in the context of their fundraising pitch.

11/ Colossus | Invest Like the Best – Nick Kokonas, Tock + Alinea Restaurant Group

Link to podcast + transcript.

One of the best podcast episodes I ‘read’ this year. It is not new, but after it was referred in the 2023 Colossus annual wrap as one of their best episodes, i decided to give it a go. Any one who is a restaurateur (esp offering mid to high priced food) or in strategy will enjoy and learn from this podcast. One of my big learnings from it was on how to figure out your revenue sources (essentially all of the experience touchpoints that customers may be willing to pay, or pay differential prices for) and make that visible to your org. Time-based pricing, and having the courage to go all-out on that, then using advance bookings / getting your customers to pay you early, and leveraging the float to buy in advance at lower prices from your vendors, so as to price the menu lower, and be competitively advantaged, were other learnings as well.

12/ Lenny’s Podcast – Carole Robin, Stanford GSB, ‘Touchy Feely’

Link to podcast + transcript.

I really enjoyed this interview with Stanford Professor Carole Robin who teaches an ultrapopular course ‘Interpersonal Dynamics’ popularly known as ‘Touchy Feely’ with the objective of helping people build strong relationships, because as she says “people do business with people, not ideas or products”! The conversation covers topics such as why vulnerability is central to strong leadership (why should someone follow you?), how to progressively and safely be more vulnerable in a relationship, the three realities underpinning any interpersonal interaction, why feedback is never negative, and why feedback is central to every relationship, but advice can hinder relationships.

I found three concepts especially useful – first the part about anger being a secondary emotion covering up for fear or hurt, was a very interesting one. Second, on the leader’s job being to ensure that the best answer is found and not necessarily by him or her, and creating a culture and environment where everyone is empowered to come up with the best answer. Thirdly, and finally, that behind every behaviour is a choice, and there is a belief and underlying mental model underprinning that choice and behaviour. We need to unlock the belief / mental model driving the choices really.

13 / Colossus | Invest Like The Best – Lulu Meservey, Rostra

Link to podcast + transcript. Excerpts from the podcast that I found interesting here.

Lulu Cheng Meservey is the founder of Rostra, the ‘PR’ firm du jour, and the high priestess of the ‘go direct’ movement, where founders are encouraged to front the message about their co to the world, instead of relying on internal or external PR teams to front their point of view. I first came across Lulu on Twitter when Dwarkesh Patel thanked her for connecting him to Daniel Yergin (resulting in a wonderful podcast episode). Hmm, I said who is this? And then I read her site (rostra.co) and her message for why founders should go direct, and I was impressed. So when this episode with Patrick O’Shaughnessy was released, I knew I had to check it out.

The episode is a great introduction to Lulu’s and Rostra’s philosophy of going direct. She covers

• Why founders should go direct – no transmission loss in messaging, all the tools of going direct are there, many have good distribution reach through their social followers etc.

• What the key elements of going direct are – loved the line on communication being a vector and not a scalar, as in, it is important to have a communication direction or objective attached to each message

• Why founders should write a manifesto whilst going direct and the contents of the manifesto

• The specific publication matters less than the right journalist for sharing the message with. Individuals >> Institutions (similar to how founders sometimes select a great Partner a Tier2 fund over a so so Partner at a Tier1 fund)

• How a good PR firm can help you ‘read the room’ (more on this below)

• Crisis PR, and why CEOs should apologise less, and do wartime scenario exercises

14/ Lenny’s Podcast – Dalton Caldwell, YCombinator

Link to podcast + transcript.

Dalton Caldwell is an exfounder and YC Partner. His podcast is an enjoyable interesting one covering a lot of frameworks such as how to think about pivots and when to pivot (has anecotes of Retool, Brex, Segment pivots), tarpit ideas (which look good but ultimately are doomed to fail, like serendpitious meeting apps) and the importance of talking to customers, and driving customer validation for the idea / product. Every month he says the founder should review the previous month’s calendar and see if at least 20-30% of the time has been spent in in-person meetings with potential customers. There is also a fun anecdote of the ‘Collision Install’, where Patrick Collison of Stripe would do the installation himself, to ensure the onboarding happened:)

15/ Colossus | Business Breakdowns – Saurabh Mukherjea on Bajaj Finance

Link to podcast + transcript.

This episode on Bajaj Finance where Matt Reustle interviews Saurabh Mukherjea of Marcellus Investments is an exceptional one. Worth a listen / read even if you are not in fintech, if only to understand what an incredibly tight biz model Bajaj Finance has built. The market share numbers (Bajaj Finance accounts for a sixth of India’s non bank lending) and growth numbers (50% Profit After Tax CAGR over 16 years( are mind blowing, resulting in a $50b market cap and a 1,000x increase in share price over the past 16 years. Whoa!

They say there are 4 elements to a lending business – cost of capital, cost of acquiring customer, quality of underwriting, and ability to collect. You need to great at at least two of these and ok at the others (cant be bad) to run a profitable lending biz. Bajaj Finance is that rare lender, who is great at all four elements, from what I understand from the podcast.

The segment on the data advantage they have, was mind-blowing. I heard once that Bajaj Finance is Salesforce’s 2nd biggest account globally. I couldn’t believe it then, but now after reading about it here, I do, and can understand why.

***

Others I liked as well but couldn’t accommodate as this was getting too long (!): Tyler Cowen talking to children’s book author and John Donne biographer Katherine Rundell, Tim Ferriss with astute people reader Graham Duncan, McKinsey interviewing incoming Disney + Reliance JV CEO Uday Shankar, David Senra of Founders Podcast on retired investor Nick Sleep’s letters, Venture Unlocked with Ben Sun of Primary VC, Lenny’s Podcast with strategy guru Roger Martin, and storytelling expert Matthew Dicks.

And, if you liked my podcast recommendations then you may like glancing throught this shortlist of my fave podcasts.

Articles

Long-time readers would know that I have been deliberately reducing consumption of articles in favour of podcasts. It is a journey that I began a few years ago, and I have stuck to that path since. 2024 was no different.

The few articles that I read this year were either from newsletters I subscribe to (Generalist, Lenny, Newcomer etc), or recommended by a few trusted curators (Diff’s Long Reads, or Jan Chipchase’s newsletter for instance) or DM’d to me by people who know me well. Finally, I also end up reading those that attract a lot of attention on twitter (e.g., Founder Mode by Paul Graham). The content is overwhelmingly in the business / tech space largely, and within that the themes of Product Market Fit or PMF, and venture investing, stand out.

So, here is a list of my favourite articles of 2024.

1/ Mario Gabriele – various

Mario’s Generalist (paywalled) had a lot of extremely interesting and educative articles on the venture industry. His series ‘Letters to a Young Founder / Investor’ (Vinod Khosla, Reid Hoffman, Ho Nam are the letter writers), Modern Meditations (interviews such as with Chip War author Chriss Miller – see below) and ‘Investor Guide’ (where he speaks to expert investors, and curates their recommendations, along with his observations on various venture industry topics, such as raising your first fund, building soft power) in particular had a lot of interesting reads.

Letters to a Young Founder: Vinod Khosla – The Story of a 2500x Investment.

Investor Guide series has close to ten or so articles. I really liked ‘How to Raise Your First Fund’ and ‘How VCs Build Soft Power’.

In addition I also liked his interview of Chip War author, Chris Miller, part of his Modern Meditations series.

2/ Graham Duncan – various

Graham Duncan, who is easing off from his role at Eastrock( a multi-family office that identified investors and then backed them with funds; essentially a Limited Partner) is obsessed with understanding and assessing people, especially investors. I had come across him in Tim Ferris’s ‘Tribe of Mentors’ long back, but had forgotten the piece. His profile in Colossus Review (paywalled, I think) was what brought him back into my consciousness. Duncan’s obsession with people reading and talent assessment really came through strongly in that piece.

Since then I have been on a Graham Duncan trip, reading his pieces such as

‘What is going on here, with this human?’

Where he collects all his recommendations about candidate selection based on the hundreds of interviews and assessments he has done.

The Playing Field

Graham says there are five levels of the investing game, from apprentice to steward. He describes the various levels and gives us some glimpses of what it means to operate at each level. Utterly fascinating.

3/ Lenny Rachitsky – Time management techniques that actually work

Lenny’s substack is one of a few newsletters I subscribe to. I read almost half of his writings, typically every one of his PMF pieces, and then some. This duo of pieces was an interesting departure from his usual writings on product management and growth topics, but resonated with me given my obsessive interest in productivity pr0n.

Link to articles: Time management techniques that actually work Part 1, and Part 2.

Good collection of time management and productivity tips and hacks. The most useful of these might be calendaring instead of to-do lists, keeping a ‘waiting for’ list, scheduling deep work time, saying no more often, moving meetings to mails, and lastly, creating a limited set of items (3 typically) that you have to get done, and doing them first in the day as much as possible.

4/ Natalie Rothfels – Why no productivity hack will solve your overwhelm

In this piece, which is a response to Lenny’s above pieces on productivity / time management, and published on Lenny’s substack, the author Natalie Rothfels, an executive coach, describes how some of her clients struggled to manage time better / be more productive despite knowing all of the techniques that Lenny suggested. She suggests the framework or practice of Internal Family Systems (IFS), to overcome these conflicts. I first came across IFS Or Internal Family Systems in an article on how Clay achieved PMF, where the cofounder Kareem Amin described using the technique. IFS propounds there is a family of different selves (the perfectionist vs the pragmatist vs the slacker etc) within us who are not entirely aligned with each other. It is a technique to understand ourselves better and to drive better alignment amongst our different selves. Kinda like the movie Inside Out!

5/ Ranjan Roy – Technology and grieving

Ranjan Roy writes about the death of his young daughter Samaya due to a rare condition called FIRES. It is simultaneously the best and the most painful read I have had in a long while. I hope this helped him process the loss somewhat.

6/ Vaishnav Sunil – Liquid vs illiquid careers

Superb framing of careers as liquid vs illiquid. TL;DR = Liquid careers have high demand and ‘legibility’ that others can attest to your value or work, e.g., a McKinsey consultant, or an elite magic circle firm lawyer, while Illiquid careers are harder to parse for market value – a freelance marketing person who previously worked in an NGO in Africa and worked in a couple of startups before that in junior roles. Interesting, but unclear what his or her value and worth is.

Essentially, if you are in an illiquid career, you have potentially higher alpha than in a liquid career, but it can be hard for others to parse your value / worth, without someone burning their social capital to promote you, and / or without signals or artifacts that you can provide to sell you better (say a blog, or a github repo etc). As someone whose illiquid career became relatively more liquid thanks to a fortunate move to VC, the article struck a chord.

7/ Tanner Greer – The Silicon Valley Canon

This essay by Tanner Greer (@Scholars_Stage on twitter) contrasting the ‘book writers’ of Washington DC and their narrow erudition, with the ‘book readers’ of Silicon Valley and their broad eclectic explorations was a fun read. In particular the contrast and framing was excellent.

Bonus: The essay has a list of the Silicon Valley ‘vague tech canon’ (recommended by Patrick Collison et al). Lots of good reads there. That said, I have always felt that podcast interviews matter disproportionately in Silicon Valley / startup landscapes, as that is the lowest friction way for tech elite to broadcast their learnings / ideas.

8/ Dwarkesh Patel – Podcast progress update

This ‘progress update’ by Dwarkesh Patel detailing how he thinks / approaches his podcast was an interesting read. Dwarkesh publishes one of the most eclectic podcast series I have seen. Perhaps only Tyler Cowen comes close. Not surprising, for both are super-learners.

This passage on how he chooses guests was illuminating: “I choose guests not based on whether I want to spend two hours chatting with them, but whether I would learn a lot by spending two weeks preparing. It’s a high bar, and it’s often uncorrelated with how famous they are.” The podcast is effectively Dwarkesh’s forcing function for learning.

9/ Todd Jackson et al from First Round – Levels of PMF

Given my obsession with product market fit (PMF), I end up consuming a lot of content on that topic. This was probably the best read of all of the lot. First Round launched their framework, or rather a program, titled PMF Method, for B2B companies with a top-down motion to systematically work towards PMF. As part of the launch of the program, they published this essay which was a description of the content in the first session of the program – introducing the framework, describing the four levels of PMF, as well as related dimensions and levers.

Overall, I thought this framework and program was a very well-designed body of work. Post the launch of the PMF Method, I wrote a review of the framework where I shared my view that I thought the framework was perhaps the most important advance in PMF lore and craft since Eric Ries’ Lean Startup.

10/ James Hawkins – The Product Market Fit Game

Excellent article by Posthog cofounder James Hawkins on a step by step guide to hitting PMF. James visualises PMF akin to a game, with 5 levels and how to jump levels. More relevant for B2B / SaaS founders than B2C given James’ experience w Posthog. Minor quibbles aside, I felt this was a truly masterful resource for iterating to PMF. Every B2B / SaaS founder starting out or an aspiring B2B / SaaS founder should eyeball / read this.

11/ Jason Cohen – The Roadmap to Product Market Fit

Jason is the founder of unicorn co WP Engine. He is a prolific writer with consistently interesting posts on various aspects of building a B2B business. I really liked this post on a step by step guide to achieving PMF. There are some similarities with the previous recommendation (of James Hawkins’ PMF Game) but there is lots different and interesting here too, including a peep into how WP Engine wrestled with these steps.

12/ Rob Go – Revisiting the craft beer metaphor for the VC industry

Fun but clever post comparing VC to the evolution of the craft beer market. Loved the analogy of YC as hard seltzer and Indie VC as non-alco beer.

13/ Palash K – All risk is creative

Interesting comparison of indie film producer A24 to venture funds. Not sure if A16Z is the right comparison, but still a good, fun read.

14 / Nicola Twilley – How to Get Rich From Peeping Inside People’s Fridges

Loved this Wired magazine profile of emerging markets investor Tassos Stassopoulos whose firm Trinetra uses ethnographic research (at the core of it is peeking into people’s fridges) to determine evolving consumption trends. The article is in fact an excerpt from Nicola Twilley’s book Frostbite on the science + downstream impact of the growing cold chain industry.

15/ David Heinemeier Hansson – The reality of the Danish fairytale

Good post by tech guru David Heinemeier Hansson (@dhh) on Denmark and the integrated choices + intentional tradeoffs behind the Danish economy + society. Think of Denmark like a less populated European Japan.

Your recommendations?

What were your favourite reads or watches or listens this year? Comment here or email me your recommendations at sp@sajithpai.com

I wish each of you a very happy new year, and hope you are able to make substantial progress this year, towards your long term and short term goals.

Quick housekeeping announcements for the new subscribers. The newsletter has two permanent sections: Writings - where I usually write and / or refer to one or more original pieces that I published in the previous months, typically about venture or the startup ecosystem, and Readings - about what I read and learnt about. My reading diet is tilted rather heavily in favour of books and podcast transcripts, and against articles / newsletters. This will naturally reflect in the reading list.

This is a long newsletter - think of it as akin to a monthly magazine from me (only the frequency may not be monthly!). I don’t know if you can read this entire newsletter (and peruse the links) in one sitting, and even if you do a second run ( which I very much doubt), you will have to pick and choose what to focus on. A good way to read this newsletter is to certainly read my original writing(s) below, and then glance through the rest and pick 1-2-3 items that pique your interest. Anything more is a bonus!

Writings

1/ AI and Cold Emails

When I entered venture, I was made aware that this is a service business, and that founders are who we serve. I made a promise that I would respond to every 1:1 (cold) mail from a founder. After all it is her or his life's work, and a reply is the least I can do.

But 6 years on, I think it is nearing the point where I need to rethink my practice of replying to every cold email, as (some) founders run AI-generated automated campaigns (See example below). The number of these types of inbounds is rising.

Am sure I am not the only VC who is at the receiving end of these campaigns (Andrew Chen is too, as you can see below!). But the long-term consequences of these campaigns is that more and more VCs will increasingly shy off from replying to cold mails and respond only to referrals. Many VCs already respond only to referrals. These campaigns will push more of us, including folks like me who try to respond to most cold emails, into that group.

Source: Twitter / X

One interesting point made by Anna Gat in a recent podcast with Dwarkesh Patel (this time he was the guest) was how she categorises cold mail that specifically is written for her on the basis of the length. The shorter the mail the more likely the author has written it only to her. The longer the message the more likely it is AI-generated (or at least created for sending to more people) and the more likely that the author will be sending it to many other folks as well. Interesting.

On the topic of cold emails, this one from Sriram Krishnan is gold.

Finally, this is an excellent example of an effective cold email

Source: Twitter / X

2/ PMF = PPF + MMF

Achieving Product Market Fit or PMF, is the single most important objective in an early stage startup. I have written extensively about PMF and how founders should understand it, and work towards it. I view PMF as a 2-step process 1) PPF or product to problem fit 2) MMF or motion to market fit. My framework as well as the playbook to work towards it is shared in a piece I recently wrote: The Busy Founder’s Guide to PMF. It is a post adapted from a presentation I made on PMF to Antler India’s Residency program founders in Sep’24.

This link has the presentation (titled ‘PMF Primer’) on PMF that I made to the founders.

3/ PMF Convo #19: Romita Mazumdar, Foxtale

In my latest PMF Convo interview, I spoke to Romita Mazumdar, founder & CEO of beauty products co Foxtale. Romita is a VC analyst turned founder, who started Foxtale during the COVID-19 pandemic, speaking to 900+ women and 100+ brands to figure out the specific sub-problem she wanted to attack in the beauty space. Foxtale is one of the fastest-growing digital-first consumer brands and this convo gave me a perspective into the key drivers of that growth. Romita’s deep understanding of the space as a user, backed by hundreds of conversations, an open mind, and innovative approaches to marketing, come alive in the chat.

In my post (the transcript is linked to in the post) we cover the limited SKU strategy Foxtale follows, how she tracks early PMF, and susses out if the product needs backing, how she divides products into acquisitory and hero products, and why founders need to score high on one of self-belief, passion or obsession (or obstinacy!). This was an enlightening conversation. Romita is an impressive young founder and it is scarily impressive how much she has achieved.

Link to the highlights and transcript of the PMF Convo with Romita Mazumdar.

4/ My ‘greatest hits’

I create a new page on my personal site titled ‘Begin here’, listing 20+ popular pieces / writings that form a good introduction to my oeuvre. I did this in response to a young reader complaining that the site seemed "overwhelming" and he "didn't know where to start".

My pieces (for those unfamiliar with my oeuvre) cover the Indian startup scene, the Indian consumer stack (including the India123 framework), the venture industry, PMF & other inputs to founders, and other miscellany. I started writing in 2012. There were no readers or visitors to the site for years. Crossposting on LinkedIn, which I started doing in 2015, and later on Medium (though I have discontinued there) helped, though I continue to publish on the site as a backup. Now there are 200+ pieces on the site. It is a testment to being consistent, at least of a kind - my consistence has reduced from ~2 pieces a month for a long while and now down to likely one every 2 months, buyt I never stopped publishing!

I find it interesting that my first big hit on the rise of the Indo-Anglians (english speaking households in India) was my 90th article. There were some minor hits before but that 90th was my first viral hit (with a lot of criticism on the interwebs etc.,). Patience, young 'uns, patience!

Readings

Podcasts are in reading because I mostly read transcripts (versus listening). I know, I know!

Podcasts

Speaking of podcasts, I made an appearance on Infinite Loops podcast. Hosted by Jim O’Shaughnessy (this is Colossus’s Patrick O’Shaughnessy’s dad) it has an eclectic collection of guests reflecting Jim’s intensely curious mind.

In the podcast I unpack the Indian startup ecosystem and the Indian growth opportunity from the vantage point of an early stage investor. Anyone looking to invest in the India opportunity and understand India will find this useful!

Here is the link to the podcast episode + transcript. This page also has a list of my writings that struck a chord with Jim; it is a sort of ‘the best of Sajith Pai’ (like by ‘Begin here’ page linked above), and gives you a sense of the range of my writing.

A/ Matt Cynamon, USV, on AI + I with Dan Shipper

30 October 2024. Link to podcast and transcript. Link to my notes / highlights.

One of the more interesting podcast interviews I have consumed in the past months / year. Matt Cynamon the 'Head of Library Sciences' at Union Square Ventures comes on the AI + I podcast with Dan Shipper to talk about all the cool AI stuff they are cooking up at Union Square Ventures (USV).

You may have seen the OH (overheard) on the USV Librarian account @usvlibrarian on Twitter. That was built by him. Over 70 mins he takes us through the GenAI stuff they are building at USV, detailing cool tools such as

- The Librarian: all the 15k articles they have written at USV which can be queried) [14:30 - 23:00 mins of the podcast]

- Meeting Notes - OH [45:00mins onwards]

- The Dream Machine [1:03 onwards] - this is v trippy...AI-generated images to sync with conversation topics - loved the whales and cats imagery!

Am sure some other VC funds have some of these built (Yohei Nakajima comes to mind), but USV is of course one of the giants of venture. Impressed with the suite of tools that USV has built out, and grateful that they and Matt have been more public about it.

A couple of interesting points that emerged from the podcast episode

* Matt says that the cost of creating good storytelling is dropping. (AI is still not ready for releasing content without final review and polish and even some rewriting, but it gets you to 60-70% of the content very fast). Hence, he says that AI can help you tell stories about things you wouldn’t create stories about, like internal meetings. There is a ton of content getting created that is not getting captured and AI can help you capture and make that content in a ready to consumer format.

* Matt: “The market for purely AI-generated content is the size of your biggest group chat.”

My take on the above two points is that as creation gets democratized and the cost of creating drops, the importance of curation and distribution become more and more important. Having content that is uniquely about your opinion or taste, and looks like / reads like content that AI couldn’t have generated (or at least without distinct prompts) begins to matter.

Content could be meta-content like The Dream Machine that he demos in the episode - AI-generated images that emerge in real time to words spoken in a conversation - as content generation gets cheaper, new content formats could be meta ideas for content generation by GPTs, like a meta content idea for creating fake but seemingly real countries in the layout of wikipedia etc.

B/ Eli Schwartz, SEO guru, on the Lenny Rachitsky Podcast

19 September 2024. Link to podcast + transcript. Link to my notes / highlights.

Sajith: Loong episode at nearly 2 hours, but worth a watch for any founder / operator wrestling with SEO or content. Eli Schwartz is one of the foremost thinkers in the SEO space today, author of the book ‘Product-Led SEO’ and advisor to Zapier, Tinder, LinkedIn etc. He speaks to Lenny on a wide range of topics related to SEO.

2 key themes in the podcast that stood out to me:

1. He covers how AI / LLMs will impact search / SEO. Effectively the top of the funnel will now be owned by Google and LLMs - so content like 20 best beach hotels in Southern Europe will now either get aggregated into AI Overviews (top hit on Google Search) or within LLMs with occasional citations, and your site will get pushed further downward. Hence the best SEO content will move midfunnel and have content that is helpful to drive conversions. This is how SEO should have been from the beginning but because it is hard to measure conversion, and harder with SEO, and relatively easier to show rankings impact, SEO got positioned as Top of Funnel.

2. The other metapoint that Eli makes is around whether you need SEO at all. Not everyone has to do SEO he says. It is best used in contexts where the customer is aware of the problem, uses specific keywords or language to understand the problem or look for a solution, and this behaviour arises naturally in the user / customer journey of addressing the problem. User Journeys is a term which comes frequently in the podcast episode, and effectively Eli is saying that if searching for content is not helpful for the user in solving the problem / and not relevant for you in driving conversion, then you don’t need SEO. Too many companies default to doing SEO because yi have raised money and you need to spend on SEO. This is wrong he says. It is expensive when you add up all of the cost of creating the content and hiring the experts. You need to consider the ROI of the investment actively like you do with Paid Marketing, but not enough companies do that he says. In his perspective, most sales-led / top-down SaaS motions can eschew their investments in SEO. It is more relevant for PLG motions like Zapier, Notion etc.

C/ Nikita Bier, teen social app guru, on the Lenny Rachitsky podcast

25 August 2024. Link to episode + transcript page.

This is a particularly good episode for consumer social app founders. Nikita Bier is well-known for having created viral teen social apps such as TBD, Gas (acquired by Meta, and Discord, respectively). This episode is interesting for his insight on why why consumer social products (that are optimising for virality) should first build for teens / use that segment as a wedge (because sharing / experimentation with new apps drops sharply after your late teens). This was fascinating.

D/ Alain De Botton, on 20VC, w Harry Stebbings

18 November 2024. Link to episode page. Link to my notes + highlights of the episode.

I thought this was an exceptional episode. Alain De Botton is a very intriguing guest for a tech podcast, but I am glad Harry did it and was able to pull it off. I read Alain De Botton’s romantic novels when I was in my 20s and enjoyed them hugely. Later he evolved into a (pop) philosopher of a kind and I kind of lost touch with his writing. I am now tempted to dip into his philosophical writing given this episode. What stands out here is his insight into the psychology of parenting, the parent-child dynamics, and the psychology of the workplace. That one line (see first para in the ‘Advice to parents’ section) where he encourages you to praise or esteem your child for what they are vs for what they did, and you will give them psychological armour for adulthood, was the biggest takeaway of the episode for me.

E/ Parker Gilbert, Numeric, on the PMF Show w Pablo Srugo

31 October 2024. Link to episode + transcript page. Link to my notes + highlights of the episode.

I liked this episode (and the series too, given it is devoted to PMF or Product Market Fit) for the intentional, frugal way in which the founder built the startup following the speedy preseed / seed raise. He was laser-focused on getting to PMF and in that pursuit, kept the team small, didn’t sell annual subs (as he felt restricting it to montly subs, would give a faster signal of churn, and would make the team be more responsive) and made sure they charged from day one (as that gave them a clear idea of what value they were offering the customer). Lots to learn for any co, but especially B2B SaaS companies from this case study / episode.

Podcast recommendation: The Joe Walker Podcast

If you like the Dwarkesh Patel podcast but cant get enough of it, and are looking for something similar (deep intellectual convos), then i would like to point you to the Joe Walker Podcast by Joseph Walker.

The podcast guests are an eclectic bunch of thinkers - academics / scientists to politicians! (He interviewed Nobel winner Katelin Kariko well before the Nobel award.)

When I encountered it first, it was titled rather memorably as the Jolly Swagman podcast. Sadly it is now the rather plainly named Joe Walker podcast. But the content is very much in the same vein as before. Joe Walker conducts deep intellectually stimulating conversations (prefaced by some ferocious prepwork) with an eclectic bunch of thinkers - academics and scientists such as nobel laureates Katelin Kariko (this before her Nobel) and Frank Wilczek to intellectuals such as Stephen Wolfram and Nassim Taleb. Like Dwarkesh Patel, Joe Walker is a professional learner in the guise of a podcast host.

An episode of his I particularly enjoyed, and recommend, was this discussion with Shruti Rajagopalan (especially her dissection of the ‘Basic Structure’ doctrine of the Indian Supreme Court).

Articles

Technology and Grieving, by Ranjan Roy

I cried reading this piece by Ranjan Roy reflecting on the death of his young daughter. It is simultaneously the best and the most painful read I have had in a long while.

Ranjan Roy (who wrote a popular piece on Doordash selling pizzas below cost) writes about the death of his young daughter Samaya due to a rare condition called FIRES. It is the bravest piece of writing I have read in years. I hope this helped him process the loss somewhat.

Margins by Ranjan Roy and Can Duruk

Technology and Grieving

It's been a while since we've last posted here at Margins. My co-host Can has been busy with his startup Felt, and I ended up on an incredible startup/acquisition journey with a DTC intimate apparel company called Adore Me. That's right, Can is selling maps and I'm selling bras. That’s how we keep this newsletter free…

Read more

2 years ago · 311 likes · 48 comments · Ranjan Roy

Books

I read three books over the past month. They are:

• The Money Trap by Alok Sama: Entertaining read by an ex-banker turned investor in Softbank, giving us a behind-the-scenes look at dealmaking at Softbank during the go-go years of the last decade. Invaluable for the behind the scenes look alone, and a glimpse into how Masa Son thinks and acts. Goes in depth into how the Softbank - Arm deal transpired, as well as how Masa won over MBS as anchor for the Vision Fund. The book tries hard to go deeper and reflect into various themes such as the author's immigrant experience, his relationship with parents etc., but the core of the book and the most interesting part is the author's relationship w Masa Son, the founder of Softbank, and the dealmaking machinations. There is also a look into the smear campaign conducted by one of his colleagues that finally led to his exit, and surprisingly despite that it is public who was behind it, doesnt mention the perpetrator's name (possibly because there was a settlement with a no disparagement clause likely).

• Behold the Leviathan by Saurabh Mukherjea and Nandita Rajhansa: an optimistic look at the Indian economic model, its rise and future prospects, seen through what the authors call the WESCO framework (rise of women, improved education, rise of southern India, China + 1, octopus or wealthy class). It is a short book, chockfull of charts, and I did get the feel of a report converted into a book. While the book is not entirely rah-rah, and it does bring up potential challenges and risks as well, it is nonetheless a highly optimistic look at India and its future.

• Breaking the Mould by Raghuram Rajan and Rohit Lamba: In contrast this is a more assertively cautious or negative take on the Indian economy and the recent policy directions. It is better written than Behold the Leviathan, and marshalls its arguments better. In particular I enjoyed reading the authors’ take on why the PLI (production linked incentive) is an expensive mistake. Along with the analysis of recent policy missteps it also tries to lay out recommendations to set the economy on the right course. Recommended if you like to read books written from a macroeconomic perspective on India.

Bye!

It is time to wrap this! As I shared earlier, you should think of this substack as akin to a monthly magazine - you don’t have to read it all in one sitting, and you don’t have to read all of it!

That is all for now folks. Feedback, or your own ruminations, in the comments or at sp@sajithpai.com (Please don’t send pitches or CVs or anything work-related at my personal id; I won’t respond to them at this id; instead please use sp@blume.vc for pitches and any official comms please).

Quick housekeeping announcements for the new subscribers. The newsletter has two permanent sections: Writings - where I usually write and / or refer to one or more original pieces that I published in the previous months, typically about venture or the startup ecosystem, and Readings - about what I read and learnt about. My reading diet is tilted rather heavily in favour of books and podcast transcripts, and against articles / newsletters. This will naturally reflect in the reading list.

This is a long newsletter - think of it as akin to a monthly magazine from me (only the frequency may not be monthly!). I don’t know if you can read this entire newsletter (and peruse the links) in one sitting, and even if you do a second run ( which I very much doubt), you will have to pick and choose what to focus on. A good way to read this newsletter is to certainly read my original writing(s) below, and then glance through the rest and pick 1-2-3 items that pique your interest. Anything more is a bonus!

Writings

PMF Playbook / The Pick

Much of my writing energy lately has been devoted to the book on Product-Market Fit (PMF) that I am working on. I researched and wrote 7 chapters that comprise Part II of the book, that I call ‘The Pick’ over the last two months. This segment is about understanding the importance of picking the right problem to work on (or the pick) for the founder, and why getting it right matters so much for eventual PMF (product market fit). By reading it, the founder gets a good idea of how to pick the problem to work on, and validate that it is indeed the right one, through the contents of these chapters.

I am presently getting these chapters beta-read by volunteer readers, who responded to my callout on Twitter and LinkedIn. For enabling beta-reading and gathering feedback, I am using a software called helpthisbook.com. Screenshots from the software.

‘PMF Playbook’ is the working title, yes. The next two screenshots show the dashboard through which I access the feedback readers shared.

In the below image, you can see how I can view the specific feedback a reader left behind. This one is re a grammatical error, but you can also leave long reflections. Oh, the image below also gives you the rough table of contents:)

I got to hear of the software HelpThisBook, from a book that I read by the creator of the software. It is a book titled ‘Write Useful Books’ and it is by Rob Fitzpatrick who also authored ‘The Mom Test’, a book I read recently as well. Both are short self-published books, and highly readable and useful ones at that.

I will be publishing the seven chapters that constitute ‘The Pick’ online in early to mid-December. Subsequently over the coming year, I will write and publish the remaining chapters too. Excited to write a book around this obsession of mine, and see it come to life.

On to other pieces.

PMF Convos

I restarted the PMF Convo series. This is where I interview founders, operators, VCs who have struggled with PMF (product-market fit) successfully, or unsuccessfully, with the startups they have founded or worked with (or work at).

Episode #17 was Mohit Kumar, cofounder and CEO, Ultrahuman, a fast-growing consumer health startup, speaking to me about Ultrahuman’s PMF journey. 

In addition, he shared

• how his view on product-market fit (PMF) have evolved, 

• why more and more brands should eschew performance marketing in favour of compounding channels like content, influencer partnerships etc., 

• why nudging consumers to open your app in the morning is an effective growth hack to drive retention, 

• as well as his advice to younger founders on building a personal runway before worrying about the company’s runway, 

• and finally his fave books and podcasts. 

Link to the complete transcript of our convo, or a shorter set of curated highlights from the chat.

***

Episode #18 was Sri Ganesan, cofounder and CEO of Rocketlane, a SaaS startup that sells software for better customer onboarding, implementation, and professional services automation. In our convo, Sri covers the Rocketlane story giving us glimpses of the decisions that led to their success. In addition he also covers his learnings on the importance of the market and picking the space to play in well. This emerges as a key takeaway from the episode.

In our conversation, we covered

• the journey of his first startup, Konotor, and how he arrived at the unlock that they were playing in the wrong end of the market, and how correcting it led to growth and momentum. 

• his definition of PMF as pull, and why stranger MRR is important 

• how they decided the problem they were going after at Rocketlane was worth it, and how they validated the solution / product

• How they arrived at the community + content playbook that has decisively contributed to Rocketlane’s success.

• his advice to younger founders and finally, his book recommendations.

Link to the complete transcript of our convo, or a shorter set of curated highlights from the chat.

Interview with Mel Goldman, early Indian Venture Pioneer

I published an interview of Mel Goldman, who effectively birthed the Indian venture scene in the late 1980s. As the World Bank officer in charge of the Industrial Technology Development Project, he identified four local partner institutions (who thus became venture capital firms) for loans, earmarked for the specific purpose of these institutions providing venture capital in turn to innovative Indian ‘startups’. From this initiative, the seeds of India’s now vibrant venture industry were sown. 

Subsequently, Mel Goldman resigned from the World Bank, and took to a life of teaching (visiting faculty at Cornell University) and farming – operating a vineyard, and eventually launching a winery. Now in his late ‘70s, from upstate New York, he runs the award-winning Keuka Lake Vineyards. In our conversation, he reminisces about his journey to joining the World Bank, and launching the Industrial Technology Development Project. He talks about his interactions with government functionaries as well as the operators at the enterprises he partnered with. The Program, as well as the pioneers who shaped and executed it, like Mel Goldman, are forgotten today. Through this oral transcript of our conversation, I hope to bring him and the Program into the spotlight, briefly.

Interesting trivia. Mel Goldman’s father Jack Goldman is regarded as the man who founded the famous Xerox PARC labs, from where originated a lot of the technologies as well as interfaces now commonly accepted as part of computing such as the graphical user interface, ethernet / networking, laser printing etc.

Link to the (edited) transcript of our conversation: My website, or LinkedIn (same content).

Two short pieces

Smart Productivity vs Wisdom Productivity

The first was on a new strand of post-productivity pr0n literature that I see emerging - the likes of Oliver Burkeman’s ‘Four Thousand Weeks’, Celeste Hadlee’s ‘Do Nothing’ - and how I see them as occupying a space I call ‘Wisdom Productivity’ in contrast to the traditional hacks around time management, and instilling habits, which I refer to as ‘Smart Productivity’. At some point in our lives, as we begin to grapple with our mortality, we switch to wisdom productivity, I posit. The (short) essay is here.

Great Curators >> Good Creators

The second, is a take on an observation made by Luly Meservey, founder of buzzy PR firm Rostra, in a podcast (more deets in the podcast section). The take was part of a review of the podcast but is excerpted here for convenience:

One interesting point she made is on the raison d’etre for Rostra, which I see as a model of an open source co (similar to open source software monetisation model), as in the co lays out all of its trade secrets for free, and charges for help around edge cases or 1% of scenarios. She says in a world where founders have all the tools for going direct and also distribution, the value of a good PR firm is helping you read the room, as in, is the message you are going with broadly still as relevant as last week, or do you need to tinker with a little bit more, and thus give you feedback around whether your message will land well. It is also helping you mitigate the curse of knowledge. This is when you are so well-versed with a concept (your product / your tech) that you think everyone else knows it as much as you do and stop seeing it from the layperson’s eyes. This is where a good PR person can help you with feedback for you to recalibrate your message appropriately. It is sort of like a book editor, except that many book editors are also gatekeepers in addition to their editorial advisory services, so this is just the editor sans gatekeeping.

This also harks to a larger point around where the alpha in content lies, and the importance of curation and the curator. If anyone can create content thanks to GPT / AI tools, and many of these folks also have larger distribution then what is the need for media publications or media services? Primarily it will be around two areas I think

• Editorial support for high stakes content: Support on creation of potentially needle-moving  / high stakes content by ‘reading the room’ / providing inputs on landing the message. Because this is high stakes content, service providers can charge a lot more than usual.

• Curating interestingness: Yes, a creator has massive distribution, but reader or user attention is the new chokepoint, and hence the value of a curator who is valued for their taste in curation, or commentary contextualising a topic’s importance, and thus becomes a trusted recommender or rebundler of content. Like Benedict Evans’ newsletter, or The Diff’s longreads mail etc. Analog media had inbuilt constraints built in (on creating / distribution), and digital media removed both creating and distribution constraints. But time is still finite, and there is a ton of content now suddenly hitting us, so the chokepoint has moved to what we can be attentive about, and hence the importance of attention agents who tell us where to direct our attention to, and where we can safely ignore, and why. A great curator can command as much alpha as a good creator.

Readings 

Notes on podcasts, articles, and books I consumed over the past two months in this section; Readings (and not ‘Readings and Listenings’) because I usually read podcast transcripts as opposed to listening to them. I know.

After feedback from a few readers, I have now spun out the VC-related podcasts into a separate substack - venturelore.substack.com - after some of my followers complained that they didn’t find the VC-related podcasts relevant. Like here.

Hence, this newsletter will have more founder / operator focused content, while Venture Lore will have more investing / venture ops content that is specific to the venture business.

Podcasts

Here are a few of the podcast episodes I particularly enjoyed consuming.

Mike Maples Jr on the Lenny Rachitsky podcast

7 July 2024

Link to podcast + transcript. 

Excerpts from the podcast that I found interesting here.

I have always enjoyed Mike Maples’s podcasts. He is a differentiated thinker, and backed by a terrific track record. These days Mike has been on a podcast tour, as he is promoting his book Pattern Breakers, which is about the success patterns or themes underlying successful startups. The title comes from his quote that “The way a startup wins is they deny the premise of the rules and propose something completely different. They radically break the pattern and cant be compared to anything which came before.” The book's basically broken up into two parts, how to come up with an idea and then the actions you need to get right to move forward an idea. In this podcast with Lenny, he covers the key themes of the book. It is worth a listen / read.

I particularly enjoyed this riff on how startups can storytell better, especially in the context of their fundraising pitch.

Emery Wells, ex Frame.io, now Adobe, on the Logan Bartlett Show

16 August 2024

Link to podcast + transcript. 

Excerpts from the podcast that I found interesting here.

Sajith: Enjoyable podcast episode where Emery Wells takes us through the founding story of Frame.io - the canonical examples of a product built for himself, the challenges they went through incl three senior execs quitting on a single day, then finding success, and the sale to Adobe. A few points which stood out

• ‘People do what you inspect not what you expect’ so if you dont inspect the work or check in that they are aligning to the expectations you set initially then great work wont get done

• Says he wants people and likes to work with people with a high pain tolerance - to do great work you need to have a high pain tolerance. The passage where he describes this seemed quiet Jobsian.

• Disagrees w the Lean Startup philosophy, and says they built it up for 2.5 yrs, didnt show it to too many people and launched. But clearly he had an immense understanding of the space and says he was customer number 1. So in this context when you are building to solve a personal pain, and you have a deep understanding of the space, then perhaps you can do the caveman approach to building.

Daniel Yergin on the Dwarkesh Podcast

18 September 2024

Link to podcast + transcript.

Excerpts from the podcast that I found interesting here.

Daniel Yergin is an oil / energy expert and author of ‘The Prize’, which is an acclaimed history of oil (and as Dwarkesh says, a parallel history of the 20th century too). I haven't read the book. It is there in the bookshelf somewhere waiting to be read. For now this podcast will do. This is a riveting episode with so many interesting threads and themes. Dwarkesh’s range is incredible - from AI to Oil to Geopolitics and History (as i post this, he is doing a live lecture with military historian Sarah Paine). He is also able to see parallels between different contexts, like w Kerosene and early AI models, which is fascinating.

What stood out for me

• For 50 years after oil was discovered its primary use was as Kerosene for lighting. When Edison invented the lightbulb there was a view that Rockefeller’s Standard Oil would go out of business. It was only when the motor car was invented and became popular that gasoline became the primary use of oil. (“In the 19th century gasoline was a waste product. It went for like three cents a gallon.” Interesting to see if there are parallels w AI, asks Dwarkesh. He says “Currently what we're using these models for is research and chat and whatever. That’s like the kerosene. What would the equivalent of billions of vehicles look like for AI?”

• The rise of AI and compute is straining the US energy grid. A slow sclerotic industry now has been jolted awake by AI’s demands. Data centers account for 4% of US electricity and is expected to go to 10% by 2030. The US electricity industry, growing 0.35% over the past 10 years, now is seeing growth of 2% a year. Daniel Yergin says “Bill Gates said we used to talk about data centers as 20,000 CPUs. Now we talk about them as 300 megawatt data centers.”

• WWII was determined by who had access to oil. Hitler’s assault on Russia was a play for Baku’s oil fields, Japan attacked Pearl Harbour when an oil embargo was levied on it. Rommel’s advances in North Africa were held back by shortage of oil. He writes to his wife, "Shortage of oil, it's enough to make one weep." Here is another from Yergin: “People have heard of kamikaze pilots who would fly their planes into aircraft carriers. One big reason they were doing that was to save fuel so they wouldn't have to fly back.”

Lulu Meservey, on Colossus’ Invest Like The Best

24 September 2024

Link to podcast + transcript.

Excerpts from the podcast that I found interesting here.

Lulu Cheng Meservey is the founder of Rostra, the ‘PR’ firm du jour, and the high priestess of the ‘go direct’ movement, where founders are encouraged to front the message about their co to the world, instead of relying on internal or external PR teams to front their point of view. I first came across Lulu on Twitter when Dwarkesh Patel thanked her for connecting him to Daniel Yergin (resulting in a wonderful podcast episode). Hmm, I said who is this? And then I read her site (rostra.co) and her message for why founders should go direct, and I was impressed. So when this episode with Patrick O’Shaughnessy was released, I knew I had to check it out.

The episode is a great introduction to Lulu’s and Rostra’s philosophy of going direct. She covers

• Why founders should go direct – no transmission loss in messaging, all the tools of going direct are there, many have good distribution reach through their social followers etc.

• What the key elements of going direct are – loved the line on communication being a vector and not a scalar, as in, it is important to have a communication direction or objective attached to each message

• Why founders should write a manifesto whilst going direct and the contents of the manifesto

• The specific publication matters less than the right journalist for sharing the message with. Individuals >> Institutions (similar to how founders sometimes select a great Partner a Tier2 fund over a so so Partner at a Tier1 fund)

• How a good PR firm can help you ‘read the room’ (more on this below)

• Crisis PR, and why CEOs should apologise less, and do wartime scenario exercises

3 x AI-related podcasts: Saam Motamedi, Gavin Baker, and Bret Taylor

Bunching these three podcasts together as they are themed around GenAI, AI’s impact on SaaS, AI economics and the likes. They were extremely useful in giving me mental tools and frameworks to grapple with the rise of Generative AI, its implications and emerging opportunities.

Saam Motamedi on 20VC

15 July 2024

Link to podcast.

Excerpts from the podcast that I found interesting here. 

In particular, I thought his framework on how existing legacy system of record giants (Salesforce, Workday, ServiceNow) can be disrupted via shifts in the data model, delivery of value, UI, was an insightful one. 

Gavin Baker on Colossus Invest Like The Best

27 August 2024

Link to podcast + transcript.

Excerpts from the podcast that I found interesting here.

This section on how the explains that GPU advances alone are not enough to understand the power of a data centre was riveting. What matters is MFU of the GPU, where MFU = model FLOPS utilization.

He then teases apart MFU into MAMMF (software efficiency) x SFU (system FLOPS efficiency). I can't say I understood it at all but it gives you a drone level view which is extremely useful.

Bret Taylor on Colossus Invest Like The Best

3 September 2024

Link to podcast + transcript.

Excerpts from the podcast that I found interesting here.

This one was particularly useful to understand the world of agentic systems. Very soon, we will be able to afford custom or generic personal agents that continually learn about us, and do all the dirty digital work (coordinating with telecallers to cancel or pause your subscriptions, or troubleshoot a bill). Similarly businesses will have functional or corporate agents. This will be the new website, and that is what Sierra is building. It is cofounded by Bret Taylor, an elite operator (ex Google, Facebook, Salesforce) who is also on the board of OpenAI.

Here is a 101 from Bret on agentic systems.

Articles

Liquid vs Illiquid careers

Link to article.

Excellent post by Vaishnav Sunil. Superb framing of careers as liquid vs illiquid. TL;DR = Liquid careers have high demand and ‘legibility’ that others can attest to your value or work, e.g., a McKinsey consultant, or an elite magic circle firm lawyer, while Illiquid careers are harder to parse for market value - a freelance marketing person who previously worked in an NGO in Africa and worked in a couple of startups before that in junior roles. Interesting, but unclear what his or her value and worth is.

Vaishnav: “When human capital is built through non-linear or less legible paths, the lack of legibility increases variance from the employer's perspective. This isn't necessarily negative, but it does increase the value of additional information. If the cost of obtaining this information doesn't justify the potential upside, candidates with less legible backgrounds may be passed over in screening processes.”

Essentially, if you are in an illiquid career, you have potentially higher alpha than in a liquid career, but it can be hard for others to parse your value / worth, without someone burning their social capital to promote you, and / or without signals or artifacts that you can provide to sell you better (say a blog, or a github repo etc).

My takeaway:

• Liquidity = demand for role + legibility of the role.

• You can use legibility signals (blog, github repo, someone burning social capital to intro you) to help others parse your career better. Appearance on lists like Tyler Cowen / Mercatus’s programs / fellows could be legibility signal boosters, and perhaps there could be a site which hosts such legibility signals and allows you to claim them to your profile boosts them as an alternate linkedin for illiquid careers.

As someone whose illiquid career became relatively more liquid thanks to a fortunate move to VC, the article struck a chord.

Time management techniques that actually work

Link to articles: Part 1, and Part 2. 

Good collection of time management and productivity tips and hacks. The most useful might be calendaring instead of to-do lists, keeping a waiting for list, scheduling deep work time, saying no more often to meetings and instead moving them to mails, and lastly, creating a limited set of items (3 typically) that you have to get done, and doing them first as much as possible. The best of what I call Smart Productivity (in the context of my above piece on Smart Productivity vs Wisdom Productivity which I hope you read or glanced through).

Why no productivity hack will solve your overwhelm

Link to article.

I first came across IFS Or Internal Family Systems in an article on how Clay achieved PMF, where the cofounder Kareem Amin described using the technique. IFS propounds there is a family of different selves (the perfectionist vs the pragmatist vs the slacker etc) within us who are not entirely aligned with each other. It is a technique to understand ourselves better and to drive better alignment amongst our different selves. Kinda like the movie Inside Out!

In this piece, which is a response to Lenny’s pieces on productivity / time management, the author Natalie Rothfels, an executive coach, describes how some of her clients struggled to manage time better / be more productive despite knowing all of the techniques that Lenny suggested given the conflicts in their Internal Family. She gives you the broad process to overcome these conflicts. Useful read, and as I shared above, you can see Lenny’s piece in the smart productivity camp, and Natalie’s in the wisdom productivity camp.

The Silicon Valley Canon / Vague Tech Canon

Link to article.

This essay by Tanner Greer (@Scholars_Stage on twitter) contrasting the 'book writers' of Washington DC and their narrow erudition, with the 'book readers' of Silicon Valley and their broad eclectic explorations was a fun read. In particular the contrast and framing was excellent. 

Bonus: The essay has a list of the Silicon Valley 'vague tech canon' (recommended by Patrick Collison et al). Lots of good reads there. That said, I H=have always felt that podcast interviews matter disproportionately in Silicon Valley / startup landscapes, as that is the lowest friction way for tech elite to broadcast their learnings / ideas.

Dwarkesh Patel’s podcast progress update

Link to article.

This 'progress update' by Dwarkesh Patel detailing how he thinks / approaches his podcast was an enjoyable read. As I shared above, Dwarkesh publishes one of the most eclectic podcast series I have seen. Perhaps only Tyler Cowen comes close. Not surprising, for both are super-learners. 

This passage on how he chooses guests was illuminating. The podcast is effectively Dwarkesh’s forcing function for learning.

Chris Miller’s interview on The Generalist

Link to article / interview.

This interview by Mario Gabriele of Chip War author Chris Miller was fascinating. Perhaps Chris can write this book on petrochemichals that he is longing to read, a la Daniel Yergin's Prize (which is his fave read). I also love this concept of aimless summer reading that he does. I remember reading somewhere how Drucker would pick one topic every 2-3 yrs and read intensely on that topic - Jane Austen was one topic / author, I remember.

Michael Pettis: “The World Is not Willing to Absorb China’s Overproduction“

Link to article / interview.

Excellent summary of the challenges facing China by Michael Pettis. Essentially it overinvested in non-productive infra, and piled on debt doing so. China’s gross fixed capital formation spends as % of GDP is 43% vs India’s 29%. In doing so it piled on a fair amount of debt. A fair bit of it is worthless, and they need to get someone - private biz, central government or local govt, to accept the losses and clear the debt.

Books

I read half a dozen books over the last few months. 

Ones that resonated in particular were 

• Rama Bijapurkar’s ‘Lilliput Land’: on the structural issues that lead to India’s undersized consumer market. Lots of interesting data here, and in typical Rama Bijapurkar fashion lots of interesting anecdata as well. I will be taking this for another round of reading over the next few months, and will be back with my take on this soon.

• Rob Fitzpatrick’s ‘The Mom Test’: Easily the single best resource for conducting customer conversations better, especially during the problem validation phase of a startup (before you build the product), is the book ‘The Mom Test’ by Rob Fitzpatrick. It is a short book, and the time of 3-4 hours invested in reading it is well worth it in terms of impact. The name comes from asking questions in such a manner that even your mom can’t lie to you, because your mom will always think whatever you tell her is a great idea, and respond effusively. Hence your questions need to pass ‘the mom test’! The book encourages you to ask questions about your customers' lives - “their problems, cares, constraints, and goals” and use these “concrete facts about our customer’s lives” to “take your own visionary leap to a solution”.  The book says that the later you mention your idea to the customer you are interviewing, and even better if you don’t mention your idea, the better the questions you will ask, and the more insights you will extract from the conversation. The book puts it well: “It boils down to this:  you aren’t allowed to tell them what their problem is, and in return, they aren’t allowed to tell you what to build. They own the problem, you own the solution.” Link to highlights / summary. 

• In addition, I read two books on successful Indian corporates: Tarun Shukla’s ‘Sky High’ (on the rise of Indigo Airlines) and Anupam Gupta’s ‘The Rise of Asian Paints’, which looked at the first ~50 or so years of Asian Paints. Recently I wrapped up Gary Sernovitz’s ‘The Counting House’, an odd piece of fiction written from the lens of the Chief Investment Officer of a university endowment! I am still processing it:) Very recently, I wrapped up Alok Sama’s ‘The Money Trap’, a fun, racy, narrative of his years at Softbank, working with Masayashi Son. Presently I am halfway through Jack Farchy and Javier Blas’ ‘The World for Sale’, on the rise of commodity traders, and the power they wield. Fun so far.

Bye!

It is time to wrap this! As I shared earlier, you should think of this substack as akin to a monthly magazine - you don’t have to read it all in one sitting, and you don’t have to read all of it!

That is all for now folks. Feedback, or your own ruminations, in the comments or at sp@sajithpai.com (Please don’t send pitches or CVs or anything work-related at my personal id; I won’t respond to them at this id; instead please use sp@blume.vc for pitches and any official comms please).

Quick housekeeping announcements for the new subsribers. The newsletter has two permanent sections: Writings - where I usually write and / or refer to one or more original pieces that I published in the previous months, typically about venture or the startup ecosystem, and Readings - about what I read and learnt about. My reading diet is tilted heavily in favour of books and podcast transcripts, and against articles / newsletters. This will naturally reflect in the reading list.

This is a long newsletter - think of it as akin to a monthly magazine from me (only the frequency may not be monthly!). I don’t know if you can read this entire newsletter (and peruse the links) in one sitting, and even if you do a second run (or more which I very much doubt), you will have to pick and choose what to focus on. A good way to read this newsletter is to certainly read my original writing(s) below, and then glance through the rest and pick 1-2-3 items that pique your interest. Anything more is a bonus!

Writings

I wrote three original long-form pieces (okay, one isn’t very long!) over the past two months. One was my reflections on TAM (Total Addressable Market) and why perhaps TEM or Total Expandable Market is a better way to think about it. In the second, I look at how senior executives planning a later shift to venture-backed startups, or want to work / associate with them should think about the shift, and execute it. Finally, in the shortest of the three pieces, I look at how revenue alone is not a valid filter in the world of consumer brands investing. 

1/ TAM: Notes and Thoughts

My thoughts on TAM or Total Addressable Market, that favourite VC coat hanger for rejecting startups, gathered into a piece. I have long held that most lazy VCs use TAM as an excuse to pass on you instead of working harder to explain their rationale for passing. I also feel that TAM is not very relevant for newer emerging categories, given that it largely measures existing demand.

The best founders and startups help expand TAM, primarily by removing friction in consumption, or by creating an entirely new customer experience via a Delta4 product. As Jason Calacanis said: “The best products induce a market to manifest itself”. But the best founders don't stop at just the great product. Subsequently they think about expanding TAM by expanding to new geographies, or selling to new customer categories, or through layering on additional new revenue streams (payments, lending, ads etc). So, really what matters is Total Expandable Market or TEM, not TAM. Finally, what matters is not so much TAM or TEM, so much as thinking about TAM in a structured manner, and bringing that structured thinking to drive business operations as well as VC discussions.

TLDR; Much like Eisenhower’s views on plans (worthless) vs planning (everything), TAM in itself is not very useful, but thinking and estimating TAM is extremely useful.

Link: ‘TAM: Notes & Thoughts’

2/ A VC's Thoughts on How Senior Corporate Leaders Should Explore and Approach Startups

Every other week, I get an inbound from a senior corporate leaders to 'pick my brain' or have an 'open-ended chat' around making a transition to venture / startups. It is hard for me to get on every call, do every coffee request or chat. I do try, but now it is getting to the point where a) it is getting repetitive for me – most calls have similar advice to offer b) it is beginning to suck out an hour from my schedule every week at least. So i thought I would convert the verbal advice that I usually share on calls into a written public piece. The advantage of this is two-fold - one, i can share this with the requestor as a pre-read, and perhaps obviating the need for a call, and two, by making it public, it would useful to a wider audience.

Here is the written piece contained what I share with them when we meet. Broadly there are four ways in which you as a corporate leader can transition to / engage with the worlds of venture and startups - join a fund, join a startup, advise, angel invest. How should you think about each of these options? And, how should you approach them? My post gives you my perspectives, both from my vantage point as a VC, and as some one who made a succesful transition six years ago from Corporate to VC.

Link: How Senior Corporate Leaders Should Explore and Approach Startups

3/ Revenue alone is not enough to estimate product strength of a consumer brand

A short post on the perils of relying on revenue alone for determining product strength of consumer brands. Yes, growing revenue is an important signal but it needs to seen along with own site revenue, repeats, stable or declining CACs and margins to arrive at a complete picture.

Link: ‘Revenue alone is not enough…’

Readings

Notes on books and podcasts that I read over the past two months. I prefer reading podcast transcripts to listening. Yes, I know.

Books

9/ Double Entry: How the Merchants of Venice Created Modern Finance by Jane Gleeson-White

9th book of the year, hence the numbering starts with 9. This was a strange book. The first six chapters are highly readable, chronicling the birth of double entry bookkeeping, against the backdrop of Venice, the leading entrepot of that era, the adoption of 'technologies' from the Muslim East (algebra, the number system, Greek mathematics), the emergence of the printing press, the ongoing Renaissance etc. The origin of double entry bookkeeping is told from the perspective of Luca Pacioli, an Italian mathematician whose book carried the first detailed exposition of the Venetian method (double entry) of accounting. There is lots here to like and learn from, in these chapters, for instance, the Venetians pioneered Abbaco Mathematics, a branch of mathematics to do with commercial topics, and Pacioli was a teacher of that. Then there are passages on Pacioli's friendship with Leonardo Da Vinci and his mentorship by the humanist Leon Battista Alberti. But from the seventh chapter, the book morphs into the impact and issues that double entry bookkeeping creates including corporate scandals etc. I did a quick scan of these chapters but didn't read them. They were a major departure from the first six chapters, which makes for an enjoyable historical read.

10/ Court on Trial: A Data-Driven Account of the Supreme Court of India by Aparna Chandra, Sital Kalantry and William H.J. Hubbard

I enjoyed this slim and enjoyable book 'Court on Trial', reviewing the (mis)functioning of the Indian Supreme Court, through data. Highly recommended. It is surprising it hasn't created the kind of noise it deserves to, given the topic it deals with and conclusions it derives.  The book was fascinating and infuriating in equal measures. Fascinating, because to a legal layman like me, it opened up the world of the Indian Supreme Court, and the challenges the court faces (the large number of cases, the pendency / delays, the power of the senior advocates, the lack of diversity on the court etc.). Infuriating, seeing the Supreme Court riddled with challenges which it has brought upon itself. The book lays out the challenges the Indian Supreme Court is grappling with, not through anecdotes (though there are some of those in the book) but through data which is not easy to come by, and was painstakingly assembled. 

Through this data, the authors come to conclusions such as the Court, in trying to be a 'People's Court', takes on too many cases, and often unimportant ones at that. Most of these cases are of a kind known as SLPs (Special Leave Petition, a provision which was only meant to be used sparingly, but accounts for a bulk of the workload of the court). The court admits a sixth of the ~60k cases it is petitioned (far too much), with SLPs accounting for 88% of these, and passes judgement in ~1k of those. (In contrast, US Supreme Court admits 1% of the ~8k cases it is appealed). Because of the lack of time to deal with the ~10k cases it admits, the ~1k judgements it passes often do not cite legal precedent, give limited guidances to the lower courts, and thus often cannot be used for future judgements. 

In different chapters, the authors cover different misfunctioning facets of the court including how the large number of SLPs lead to admission hearings on mondays and fridays, where the 'elite senior' advocates get facetime of 90 seconds per case, and charge anywhere from 1L to 15L per appearance. Many of these hearings are influenced by the signaling power (or 'face value') of the Senior Advocates. It looks at how the power shifted from judges to senior advocates and asks what can be done to redress that. Subsequent chapters look at topics such as diversity, political influence, the power of the Chief Justice in determining which judge is assigned to which case, etc. All of these are analysed, and conclusions are drawn through the use of data. Despite all of the legal arcana, the book was an easy read, even for a legal layman like me. It is also a relatively slim read (around 200 pages). Recommended read.

(Also check out Aparna Chandra’s appearance on the Ideas of India Podcast. This was a very good episode.)

11/ Accidental Empires: How the Boys of Silicon Valley Make Their Millions, Battle Foreign Competition and Still Don't Get a Date by Robert X. Cringely

Fun, racy, spicy, ultra-gossipy read of the history of Silicon Valley, and the shenanigans of the computer pioneers (Bill Gates, Steve Jobs etc) from the 1970s-80s. That said, it goes beyond gossip and funny anecdotes to cover the shifting technological trends and business dynamics of the industry as well. There is also a deep dive into the culture of then startups Microsoft, Adobe, Apple, Lotus etc., as well as behemoth IBM (the best one). Its ability to mix and cover tech trends, business strategy, as well as bad boy behaviour, equally well made it an enjoyable and interesting read for me. The book became notorious when it was first released in 1992 (apparently Microsoft tried to get it banned) because it mentioned stuff like Bill Gates not showering regularly, and drunk-bitching about IBM in a meeting with Lotus executives (which found its way to IBM). Should you read it? Well, if you have a deep interest in Silicon Valley history like I do, go for it. If you don't, then strictly don't bother, though if you do, you won't be disappointed!

12/ Write Useful Books: A modern approach to designing and refining recommendable nonfiction by Rob Fitzpatrick

A short and highly readable guide to writing the non-fiction book that dispenses actionable advice, and helps readers achieve their outcomes (books like The Lean Startup, Building a Second Brain etc., which the authors calls 'Problem-solvers') as opposed to non-fiction works that are edutainment products such as Malcolm Gladwell or Steven Johnson's books (which he calls 'Pleasure-givers'). Writing a 'Problem-solver' needs to be approached very differently, says the author, noting that much of the advice that is usually dispensed for non-fiction books is for 'Pleasure-givers'. For one, you need to define the scope and the audience tightly enough that there is a strong promise (it is hence 'Desirable'), it needs to deliver on the promise by offering a high degree of value ('Effective'), the reader should not have to work very hard to extract that value ('Engaging') and finally it needs to be aesthetically designed and well-produced ('Polished'). 'Desirable', 'Effective', 'Engaging' and 'Polished' add to the acronym DEEP, which is a handy way to remember the attributes of a successful 'Problem-solver'. Such a work, he says, will become a self-recommending title, because it is actionable and useful for anyone faced with the problem, that the book has solutions for. 

The author shares a lot of useful tips to create self-recommending titles, such as 1) a descriptive Table of Contents, with each chapter's description being the benefit or value the reader gets from reading the chapter 2) front-loading the value - quickly getting to the meaty parts / main course instead of forcing the reader to consume a lot of starters or front matter 3) having 'listening' and 'teaching conversation' with prospective readers to validate the Table of Contents, and some key chapters 4) striving for high value per pages turned - reviewing the pages per value or benefits offered, and so on 5) Beta-testing the book with a select group of readers you recruit 6) a guide to self-publish and market the book 7) how to decide on the cover page, and so on. All in all, a useful read for anyone looking to write a 'problem-solver'.

13 / Beyond Market Value: A Memoir of Book Collecting and the World of Venture Capital by Annette Campbell-White

Interesting but ultimately disappointing book this, an autobiography by a venture capital investor and rare book collector. I was expecting an equal weightage to both topics, but sadly it is a bit weighted in favour of book collecting. As a female investment banker-turned venture investor, and as one of the few female VCs in her time, a detailed and comprehensive narrative of her career and investing experiences would have been fascinating to read. In fact we do get a few glimpses of this but they are too few and far between.There is far too much space given to books and book-collecting, and while there are some amusing anecdotes, sadly much of it is not as interesting as the venture part. Yes, your mileage may vary, depending on your interests. That said I have reasonable interest in both and yet, I felt the book collecting part overwhelmed the venture part, leading ultimately to a book that is not as intriguing as the cover and premise suggests. That said, a beautifully produced book.

Podcasts

1/ Capital Allocators Podcast: Dan Tennebaum on the case for India

Link to podcast.

I thought this comparison between India and China over the past 25 yrs was really interesting. By India public market investor Dan Tennebaum of India Capital (they have a concentrated 16 stock portfolio exposure to the Indian market) in the Capital Allocators Podcast.

The episode is a good listen for public market investors, especially how they research the true value of companies by digging into land records, talking to customers of the companies to estimate pricing power etc.

Explanations to the above in QTs and replies here - on Twitter, on LinkedIn -

and, reply by the author on LinkedIn

2/ Business Breakdowns: Saurabh Mukherjea on Bajaj Finance

Link to podcast + transcript.

This episode on Bajaj Finance where Matt Reustle interviews Saurabh Mukherjea of Marcellus Investments is an exceptional one. Worth a listen / read even if you are not in fintech, if only to understand what an incredibly tight biz model Bajaj Finance has built. The market share numbers (Bajaj Finance accounts for a sixth of India’s non bank lending) and growth numbers (50% Profit After Tax CAGR over 16 years( are mind blowing, resulting in a $50b market cap and a 1,000x increase in share price over the past 16 years. Whoa! 

They say there are 4 elements to a lending business - cost of capital, cost of acquiring customer, quality of underwriting, and ability to collect. You need to great at at least two of these and ok at the others (cant be bad) to run a profitable lending biz. Bajaj Finance is that rare lender, who is great at all four elements, from what I understand from the podcast. 

This screenshot, on the data advantage they have, was mind-blowing. I heard once that Bajaj Finance is Salesforce's 2nd biggest account globally. I couldn't believe it then, but now after seeing the below I do, and can understand why.

3/ Ideas of India: Karthik Muralidharan, UCSD Professor

Link to podcast + transcript.

Enjoyable and interesting episode where Shruti Rajagopalan interviews Karthik Muralidaran, author of the book ‘Accelerating India’s Development’, a prescriptive book where he writes on how specific interventions around improving the quality of expenditure in areas such as healthcare, education can yield dramatically improved outcomes. I haven’t read the book yet though the podcast episode gives you a sense of the contents. The core message of the book is that too much rhetoric is devoted to what the government should do, while remarkable little is around how it should do it, and that matters because thinking about the how, and interventions around these can generate very high returns for the investment undertaken. I found the discussion on centralisation vs fiscal federalism in the context of India and US respectively utterly interesting.  The other interesting theme was around government pay (high) and recruitment (too few) in India and how that limits state capacity. During the course of the podcast, Karthik Muralidharan shares this deeply thought-through ideas such as the Practicum and Empanelment, and interventions around local hiring, as well as hiring a second anganwadi worker etc. A good read / listen for those with an interest in public policy and statecraft, and India, or all of these.

4/ Lenny Rachitsky Podcast: Dalton Caldwell, YCombinator

Link to podcast + transcript.

Dalton Caldwell is an exfounder and YC Partner. His podcast is an enjoyable interesting one covering a lot of frameworks such as how to think about pivots and when to pivot (has anecotes of Retool, Brex, Segment pivots), tarpit ideas (which look good but ultimately are doomed to fail, like serendpitious meeting apps) and the importance of talking to customers, and driving customer validation for the idea / product. Every month he says the founder should review the previous month’s calendar and see if at least 20-30% of the time has been spent in in-person meetings with potential customers. There is also a fun anecdote of the Collision Install, where Patrick Collison of Stripe would do the installation himself, to ensure the onboarding happened:)

5/ Lenny Rachitsky Podcast: Carole Robin, Stanford Professor

Link to podcast + transcript.

Really enjoyed this interview with Stanford Professor Carole Robin who teaches an ultrapopular course ‘Interpersonal Dynamics’ popularly known as ‘Touchy Feely’ with the objective of helping people build strong relationships, because as she says “people do business with people, not ideas or products”! The conversation covers topics such as why vulnerability is central to strong leadership (why should someone follow you?), how to progressively and safely be more vulnerable in a relationship, the three realities underpinning any interpersonal interaction, why feedback is never negative, and why feedback is central to every relationship, but advice can hinder relationships.

I found three concepts especially useful - first the part about anger being a secondary emotion covering up for fear or hurt, was a very interesting one. Second, on the leader’s job being to ensure that the best answer is found and not necessarily by him or her, and creating a culture and environment where everyone is empowered to come up with the best answer. Thirdly, and finally, that behind every behaviour is a choice, and there is a belief and underlying mental model underprinning that choice and behaviour. We need to unlock the belief / mental model driving the choices really.

Bye!

It is time to wrap this! As I shared earlier, you should think of this substack as akin to a monthly magazine - you don’t have to read it all in one sitting, and you don’t have to read all of it!

That is all for now folks. Feedback, or your own ruminations, in the comments or at sp@sajithpai.com (Please don’t send pitches or CVs or anything work-related at my personal id; I won’t respond to them at this id; instead please use sp@blume.vc for pitches and any official comms please).

Quick housekeeping announcements. The newsletter has two permanent sections: Writings - where I usually write and / or refer to one or more original pieces that I published in the previous months, typically about venture or the startup ecosystem, and Readings - about what I read and learnt about. My reading diet is tilted heavily in favour of podcast transcripts (and of course books) and against articles / newsletters. This will naturally reflect in the reading list.

This is a long newsletter - think of it as akin to a monthly magazine from me (only the frequency may not be monthly!). I don’t know if you can read this entire newsletter (and peruse the links) in one sitting, and even if you do a second run (or more which I very much doubt), you will have to pick and choose what to focus on. A good way to read this newsletter is to certainly read my original writing(s) below, and then glance through the rest and pick 1-2-3 items that pique your interest. Anything more is a bonus!

Writings

The Indus Valley Report

Much of the first two months of this year went into working on and publishing The Indus Valley Report. Indus Valley is our moniker for the Indian Silicon Valley or Indian startup ecosystem. This is an annual report I conceived around two years ago, as a kind of a stocktaking of the Indian startup ecosystem. I work along with a colleague (this year there were three of us) to publish this report, typically around late February / early March every year. It is timed for release around our annual Blume Day (which happens late February). This was the third edition of the report. Links to past editions: 2023 edition, 2022 edition.

The Indus Valley Report celebrates the rise of the Indian startup ecosystem, and its emergence as one of the centres of innovation and enterprise in the startup world. Through 150 or so insightful, and some provocative charts, this year’s report identified key themes, patterns and trends in the Indian startup and venture ecosystem, as well as hinted at what is coming next.

This year’s report covered themes such as

• How 30 million households are fueling the majority of consumption in India.

• India's K-shaped recovery and the rise of premiumization.

• How digital public infrastructure has made India a digital welfare state and also helped various startups flourish.

• Why India is going through a booming IPO market and the rise of "SME IPO" as a new way to raise capital.

• How digitally native Indian brands are rewriting international and domestic playbooks.

as well as a look at many more deep dives and playbooks on what makes India a unique market and startup ecosystem.

In addition, this year, we also did a youtube explainer episode where we unpacked this year’s report.

The Indus Valley Report has become an anticipated fixture in the Indian startup ecosystem. It is also heartening to note that it spurs the creation of further tweet threads / posts, explainer videos, commentary etc.  Special callout to Varun Mayya who did a wonderful explainer of the report in his inimitable style (He did one last year too). Think School / Ganesh Prasad did another highly appreciated explainer as well.

There were a whole lotta memes as well!

The report does take a fair amount of time to create. We go through 100+ reports and surveys across various sectors (not to mention articles), and scrape around 3,000 or so charts which we distil / remix into 150 or so charts and a set of narratives. The report-making process starts around October with initial brainstorming around the structure as well a first run at the reports we have collected. This is a divergent / exploratory phase. By mid to end December we broadly lock in on the structure. Of course there are always some changes in the structure by the time we get to the end but it is more or less set.

January and February is when we narrow down our aperture – this is the convergent phase where we now start distilling / removing what is unwanted and figure out the essential. This is also when we start creating the slides. Since we do all the slides (no design partners / consultants), and regular venture work doesn’t stop, this does mean a lot of evenings and weekends kept aside for Indus Valley work. Since the last three years, I have been joking that given that Indus Valley Report’s prep work happens during what is the ‘festive season’ in India (November - February), I don’t get to enjoy the festive season and Delhi winters as much as I would like to.

I am not alone. Larry Fink of Blackrock publishes his famous annual letter, and it sucks hundreds of his hours during the September to January period. Here he is (referred to as LF) talking to David Rubenstein (DR), cofounder of Carlyle; this excerpt is from David Rubenstein’s book of interviews of well-known investors, titled How to Invest.

“DR: Warren Buffett popularized the idea of having a letter to his shareholders telling everybody what he thinks. You have, with him, become probably the most prominent person who writes a letter to shareholders. How long does it take you to write that letter, and how much time and thought do you put into it?

LF: It’s hundreds of hours. I generally don’t put pen to paper until September, but it’s a dominant component of September through January in terms of my life…. my letters are well received by our clients, and I do believe it helps drive the success of the firm.”

Then there is Dan Wang, who used to write a famous annual letter on China. He writes:  “I’m not going to write many more of these letters. After five, the end is in sight. Writing these pieces demands an enormous effort of concentration. It’s the timing that hurts: I am working hard in the last ten days of the year, doing my most frenzied thinking when everyone else is in the happiest mood of relaxation. It’s getting annoying that I wish I could take a break from Christmas and New Year’s. Therefore, I’m trying to terminate this annual burden. I think I will write these again, but not more than one or two.”

Byron Wien of Blackstone used to write his famous 10 Surprises till he passed away. From his NYT obituary: “One place the list was not popular was his own home. “My wife hopes I give this up as soon as possible,” Mr. Wien told The New York Times in 2001. “While people are enjoying the holidays, between Thanksgiving and Christmas I am in a total panic, working quite hard on developing these.”

Other Writings

I wrote two other pieces – one on strategy, and my take on it, and the other was a review of First Round’s PMF Method framework and program that they launched recently.

In my essay on strategy, titled ‘Reflections on Strategy’, I take a deep dive into strategy and culture, two of the most ill-used terms in business, and how they relate to startups. I share a definition of strategy, and drill deeper. If I could leave you with 3 takeaways from this piece, it would be
- Strategy is about choices and tradeoffs around ‘where to play’ and ‘how to win’
- the most important choice is around where to play
- a winning business system (interlinking of product, rev model, GTM and team) needs to be married with the right capital structure, to arrive at a solid how to win.
Link to ‘Reflections on Strategy’.

In the first week of April, First Round Capital's PMF Method framework launched. Given my obsession with PMF and past writings on the topic, I had the framework forwarded to me by multiple people! Now, having digested this over the past few hours, I do feel this is *perhaps the the most important advance in PMF lore and craft since Eric Ries’ Lean Startup*. Here is my review of the First Round PMF Method including a few minor areas it comes up short. Overall, I think this is a very well-thought out and put together body of work. Link to my review of First Round’s PMF Method.

Readings

Books

After a slow start on the book reading front (largely because much of free time in January and February went into the Indus Valley Report), I have been able to get a regular reading cadence going. Despite my best attempts, I am not reading as much fiction, and older books as I would like to.

Here is what I read

1/ More Money Than God (2010), by Sebastian Mallaby - A history of the Hedge Fund industry by the author who gave us The Power Law, a history of the venture industry. Readable and entertaining in most parts barring some pages covering deal structuring which was a tad non-intuitive. Skimmed through those parts.

2/ India is Broken (2023), by Ashoka Mody - Good breezy read on India's economic history since 1947 with a deep dive and discussion of its economic failings. Skewers both the Congress and the BJP.

3/ How Big Things Get Done (2023), by Bent Flyvbjerg and Dan Gardner - Bent Flyvbjerg is an expert on megaprojects and why most megaprojects are delayed and overbudget (only 0.5% of megaprojects are underbudget and on time he says). In this book, he covers why most megaprojects 'fail' and how you can get them done in time and underbudget. Good easy read with lots of examples.

4/ Private Equity: A Memoir (2024), by Carrie Sun - Roman a clef novel that is about the author's stint as an executive assistant to Chase Coleman of Tiger Global, and how the stress and pressures of the job nearly broke her. In the second half of the book it also covers the author's dysfunctional relationship with her parents, who were immigrants to USA, as well as her complex and toxic relationship with her boyfriend. Readable but ultimately not deeply satisfying; somehow I could not generate deep empathy or sympathy for the character, not sure why.

5/ Tokyo Express (1958), by Seicho Matsumoto - Lovely short crime thriller / police procedural set in 1957 Japan. If you are into trains and schedules, you will love this book even more, as the plot is built around the protagonists' clever hacking of train schedules.

6/ The Grid (2007), by Philip Schewe - History of the electric grid and its evolution. Unfortunately, not a good book. It is interesting in parts given the topic itself, but the bad style of writing (excessively lyrical, ornamental and not so direct writing) lets it down.

7/ The Learning Trap (2023), by Pradip K Saha - Not so well-written (and edited) book on the Byju's scandal. Could have covered much more (such as Byju the person, the investor dynamics around why the Board didn’t push harder etc.,) but doesn’t, and does not go as deep as a book should. Felt like it was rushed out to take advantage of the Byju negative buzz.

8/ Snow Leopard (2022), by Nicholas Cole, Eddie Yoon and Christopher Lochhead – Heard about this book from a Lenny Rachitsky podcast appearance on Colossus’s Making Media. This is a book about the principles of category design (pioneered by Chris Lochhead) applied to writing books. Essentially the books says to create non-obvious content and / or invent your category and dominate it (like Ryan Holiday and Stoicism). The broad idea or thrust is interesting, but is ill-served by the length and the poor structure. It is like a series of paragraphs sprung together. There is a fair amount of repetition as well. There are some interesting passages as well as a section where they look at the top-selling non-fiction books and derive insights from that. Overall I felt the book could have been a 40-50 page monograph.

Podcasts

Many of you know that I have been deliberately eschewing articles in favour of podcast transcripts (given the higher signal to noise ratio in these). That trend continues.

Here are five podcasts whose transcripts I enjoyed reading, with my learning notes on them. For the last three podcasts in the list below, I organised the transcript, as the podcast publisher doesn’t provide the transcript. You are welcome!

A/ Nick Kokonas, Tock + Alinea Restaurant Group, on Colossus w Patrick O’Shaugnessy

Link to podcast + transcript.

One of the best podcast episodes I ‘read’ this year. It is not new, but after it was referred in a Colossus annual wrap as one of their best episodes, i decided to give it a go. Any one who is a restaurateur (esp offering mid to high priced food) or in strategy will enjoy and learn from this podcast. One of my big learnings from it was on how to figure out your revenue sources (essentially all of the experience touchpoints that customers may be willing to pay, or pay differential prices for) and make that visible to your org. Time-based pricing, and having the courage to go all-out on that, then using advance bookings, and leveraging the float to buy in advance at lower prices from your vendors, so as to price the menu lower, and be competitively advantaged, were other learnings as well.

This below is one of the best examples of the strategic use of working capital i have read. Getting your customers to pay your early, and then using that neg working capital / float to get crazy good deals from your vendors. I believe Trader Joe's does similar stuff too.

B/ Ben Gilbert + David Rosenthal, on Hermes, in Acquired

Link to podcast + transcript: https://www.acquired.fm/episodes/hermes

Excellent episode, where the hosts dig deep into the Hermes history as well as their manufacturing process, with lots of fun facts sprinkled across such as how they never openly reveal their highest-selling and most prestigious products, the Birkin and Kelly bags. Overall an excellent episode to listen to, and one of the many that have come on luxury brands such as on Ferrari, Rolex and Patek (all in Colossus’ Business Breakdowns; the Rolex one in particular was v good). Common to all is that you cant just walk into a store and walk out with a purchase. Often the one you want will not be available or you will be told the ones in stores was reserved for a specific buyer. Purchase of choice products is subject to you building a track record or purchase history over time and spending a lots of money on what you really dont need before you get to buy what you want:)

C/ Sarah Tavel & Eric Vishria, Benchmark Capital, on Turpentine VC, w Erik Torenburg

Link to podcast. Link to Transcript (organised by me).

Benchmark is such an interesting firm, given the strategic choices they made around equal partnership, and working without any support (no analysts / associates, just an occasional Principal, and no platform team). In this episode, there are interesting discussions of the implications of these choices and tradeoffs. The bad is that this can mean insufficient coverage (not enough cold bodies to email) or support to founder, but the good is that it is a forcing function to focus on what is truly important, which is direct time to the founder on key inflection points, and build greater and better context about the business which informs future decisions. There is also an interesting section on how they think about future Partners and recruit them. Benchmark is a one of a kind firm. It is very unlikely there will be too many more like it, so it is unlikely any of their strategic choices will fit those of other firms, but it is fascinating to see the entire set of choices and tradeoffs, and how they make for a firm like them, and the implications of these choices.

D/ Logan Bartlett, Redpoint Ventures, on Turpentine VC w Erik Torenburg

Link to podcast. Link to transcript (organised by me).

Good episode for venture nerds. Covers a diverse range of topics including why venture is oversized as an asset class, why we have exaggerated the barbelling (boutique at one end and supersized at the other) of venture, the rise of funds such as Founder’s Fund, Thrive, Amplify, how Redpoint uses firm brand to enter the room, and partner brand to win the deal, and so on. Consistently interesting. The story of how he was hired - the other Redpoint Partners wearing Wu Tang Clan sweaters - was fun. It reminded me of the story on Sequoia’s website on how Jess Lee was won over by Sequoia Partners Roleof Botha and Jim Goetz dressed as Woody and Buzz Lightyear coming over with the offer letter.

E/ Howard Morgan, BCapital Group, on Turpentine VC, w Erik Torenburg

Link to podcast. Link to transcript (organised by me).

Fun enjoyable podcast with the Forrest Gump of Venture and Investing, Howard Morgan, who has been part of cofounding three iconic institutions (Rentech, Idealab, and First Round Capital), and is on his fourth, B Capital.  It is of course an enjoyable chronicling of his journey and adventures in venture capital, but it is also a glimpse into how First Round Capital and great venture firms are built and the processes underpinning these cultures (like instilling a written vote / note before the Investment Committee discussion so folks don’t try to read how the firm’s seniors are leaning and are forced to share their independent views). Some fun anecdotes here like how Josh Kopelman (First Round Capital’s cofounder) got a town in Oregon to change its name to his startup’s name, how they monitored Bill Gurley’s twitter feed to get investing signals and so on. Enjoyable treat for venture (history) nerds.

Bye

It is time to wrap this! As I shared earlier, you should think of this substack as akin to a monthly magazine - you don’t have to read it all in one sitting, and you don’t have to read all of it!

That is all for now folks. Feedback, or your own ruminations, in the comments or at sp@sajithpai.com (Please don’t send pitches or CVs or anything work-related at my personal id; I won’t respond to them; instead please use sp@blume.vc for pitches please).

There are 3 parts to this issue, a longer one on what I enjoyed reading (across books and podcast transcripts) this year, as well two shorter ones on what I enjoyed listening (music) and watching (web series).

Reading

Book reading is a competitive sport for some. Some want to read 52 books, one for every week. Some are more ambitious, going for 100 books. There was a time when I had such ambitions though I now strive to read fewer books. It is a realisation arrived after a year of book bingeing when I arrived at the end of the year, and stuggled to remember what I had absorbed. I almost had no memory of what was in those books. That is when I decided, I would strive for ‘fewer but better’ when it came to books.

I ended up with 17 books this year, just over half of what I read last year. Now, I do skim through or rush through a quarter of these books. It doesn’t pay to be OCD about reading each page, I have figured.  This is not the lowest I have read in a year (have gone to as low as 14 books in some years), but this is below the average annual number (23) I have read in the past two decades. Low is good, and that makes me happy.

I read five works of fiction this year. I have been trying to increase the number of fiction works I read, and this was in the right direction. I have also been trying to read older books, and here I failed. I read far too many newly published works this year. A key reason for reading older books is that they are likely to be better, going by the Lindy principle.

This year’s best fiction read was Jeffrey Eugenides’ Middlesex. I had heard about the book but what spurred me to buy it and read it, was a comment by my colleague Ria, in an interview that it is her favourite book, and one she rereads every year. I had high expectations going in and wasn’t disappointed. It is an extraordinary read, covering the story of the transgender Calliope / Cal Stephanides, and the three generations of the American-Greek Stephanides family. It is funny, but also bittersweet, and tragicomic and utterly riveting. Most of all, Jeffrey Eugenides is a magician with the language, using arresting metaphors and analogies to build out a highly readable arresting classic. As with some of my previous fave reads (like A Suitable Boy), I had to ration myself on not reading faster, for I wanted to make it last.

Two other works of fiction delighted me. One was Vivek Shanbagh's 'Ghachar Ghochar', a translation from Kannada. It describes an economically ascendant family that grows steadily dysfunctional with their shift to new house and shifting power equations within the family. Shanbagh is a genius at steadily building up atmosphere and claustrophobia, with economical use of language and a tight narrative arc. The book is a tiny masterpiece, the entire book is only about 117 pages long.

The other was 'Roman Stories' by Jhumpa Lahiri (one of my favourite writers). Jhumpa Lahiri's book is a collection of stories set in Rome, featuring nameless immigrants and locals, but richly wrought out, each wrestling with unrooting, alienation, the uncertainties of memory etc., her typical themes but now dealing with non-Indian characters in the Italian landscape. I find it fascinating that Ms Lahiri now writes in Italian (having moved to Italy to learn the language), and that this piece was a translation (also like Ghachar Ghochar).

Another translation this time in faction / non-fiction, was my favourite non-fiction read of the year. This was 'Papyrus', by Spanish writer, Irene Vallejo, an eclectic, wide-ranging exploration of the origin of books, and early book culture (Alexander to Romans), and a celebration of the written word. Runner up was Pulak Prasad's 'What I learned about Investing from Darwin', his rules for public market investing and how it resonates with ecology & biological principles (fascinating both for the comparison and a glimpse into the public market investing style employed by Nalanda).

*

A lot of the time allocated to book (and articles) reading was replaced by podcast transcript reading, typically tech / venture podcasts. Yes, I never watch podcasts on Youtube, and only rarely listen. My preferred consumption style is reading text, and I have optimised for that by downloading transcripts as pdfs on my Remarkable device. I can mark it up and transfer highlights from that to my notes app easily. Given most startup and venture podcasts publish transcripts these days, I don’t need to put much effort into getting the transcripts. For the ones that don’t do, I get my assistant to transcribe it via Rev, and edit it a bit for formatting.

Why less books (or articles) and more podcast transcripts? Well, regular readers of my writings know about my views on podcasts as well as how I see tech and venture podcast transcripts as having amongst the highest insight density per page of all forms of writing. So, I am very happy with the shift to reading more podcast transcripts.

On podcasts, I find that there are six I find frequenting more than the others – they are 20VC by Harry Stebbings, Colossus’ Invest Like The Best, Lenny’s Podcast, Dwarkesh Podcast, Acquired, and Venture Unlocked.  All six publish transcripts now. For each, I picked one representative episode. Here they are

1.    20VC – Rob Go of NextView Ventures giving you the inner mechanics and dynamics of raising a venture fund.

2.    Colossus’s Invest Like The Best - Scott Davis & Rob Wertheimer, authors of ‘Lessons from the Titans’ detail learnings from their book covering high-performing industrial companies such as Danaher, Roper, Honeywell, and draw out lessons from their success while contrasting them with high profile failures such as GE. 

3.    Lenny’s Podcast – Andy Raskin describes how to create a strategic narrative, a simple story to help people understand why to use / back your product.

4.    Dwarkesh Podcast – riveting exposition of military strategy or specifically grand strategy, and associated concepts by Dr Sarah Paine, Professor of History and Strategy at US Naval War College.

5.    Acquired – Enjoyed this long but riveting deconstruction of Costco’s strategy by Ben Gilbert and David Rosenthal including the interconnected choices, and intentional tradeoffs, that have led to one of the most formidable and valuable retail companies today.

6.    Venture Unlocked – Kyle Harrison of Contrary Capital covers emerging themes in the venture business such as shift in power from firm to superstar partners, and implications of that.

Watching and Listening

Writing, and reading mean something must give and that was watching. I didn’t watch too much to be honest. As to listening, given it can run parallel to other activities, it doesn’t get compromised as much.

Watching: Recently I liked 'Slow Horses' (Season 1), a spy thriller on Apple. Before that Raj & DK's 'Guns & Gulaabs' and 'Farzi' (Vijay Sethupathi is sooo good in Farzi!) I also liked 'Class' the remake of Spanish hit 'Elite' (the music is incredible - especially love Nayantara Bhatkal on 'Girta Sambalta'). I possibly watched and liked a few more but can’t recall now!

Listening: Beach House, and shoegaze / dream pop was my big discovery this year. Beach House was my most listened to band. Cocteau Twins came a far second. If you like music like Cigarettes After Sex, then you will like Beach House, though it has far more variation than Cigarettes After Sex. It is joyful, buoyant, wistful, nostalgic, sad, full of longing, ambient and so on. Beach House was the background music for much of my Indus Valley Annual Report work, filling in those cold winter nights.

Your recommendations?

What were your favourite reads or watches or listens this year? Comment here or email me your recommendations at sp@sajithpai.com – if I get enough I will add them here with due credit to you.

*

I wish each of you a very happy new year, and hope you are able to make substantial progress this year, towards your long term and short term goals.

Quick housekeeping announcements. The newsletter has two permanent sections: Writings - where I usually write and / or refer to one or more original pieces that I published in the previous months, typically about venture or the startup ecosystem, and Readings - about what I read and learnt about. My reading diet is tilted heavily in favour of podcast transcripts (and of course books) and against articles / newsletters. This will naturally reflect in the reading list.

This is a long newsletter - think of it as akin to a monthly magazine from me (only the frequency may not be monthly!). I don’t know if you can read this entire newsletter (and peruse the links) in one sitting, and even if you do a second run (or more which I very much doubt), you will have to pick and choose what to focus on. A good way to read this newsletter is to certainly read my original writing(s) below, and then glance through the rest and pick 1-2-3 items that pique your interest. Anything more is a bonus.

Writings

1/ A question I get all the time is how to break into VC (venture capital), or what gets you selected into a venture fund. I understand: VC is seen as a desirable job, and there is a fair amount of applicants for every role, so how does one stand out especially if not from a IIT or a BITS. So, here is my rough guide for breaking into VC. This would be useful for any level, but most for Analyst / Associate role aspirants in early stage VC.

In the post, I share my earned secrets gathered over the past five years in venture: why top-tier VC is a sellside not a buyside business, why top-tier VC is best seen as a form of enterprise sales where you sell your firm's brand of capital in turn for equity, and therefore why firms evaluate you on the basis of your ability to connect, engage and persuade rising or star founders. In addition, I share six ways to signal your abilities on this front, and stand out vis a vis other candidates. I hope you find this rough guide to breaking into venture useful!

Link to the piece.

2/ I published 2 episodes of my PMF Convo series. These are 1:1 zoom or in person conversations I have with founders, operators, VCs as part of my research on PMF (product market fit). I record and transcribe these conversations, and if the guest is willing, I release the edited transcript (no audio).

In PMF Convo #15, I spoke to Ranjeet Pratap Singh, the cofounder of Pratilipi. I have, for long, enjoyed Ranjeet’s tweets and thoughts on the challenges and learnings from building a content platform in India - one that has paved the way for a wave of vernacular language apps to inspire and follow and expand the market. In our convo, Ranjeet doesn't disappoint. He is his trademark candid, first principles self, talking about why he doesn’t like the concept of PMF (too vague), and why a better framework is to see the early startup journey as one of verifying each of the hypotheses that need to hold true for the vision to be realised, and why businesses need to address the biggest risk first.

Ranjeet then explains his perspectives on Network Effects ventures like Pratilipi - how network effects businesses see engagement metrics such as time spent increase with scale, unlike say a pure media business, the importance of liquidity (or supply of inventory) as a way to measure the health of a marketplace with network effects and finally, why frequency of usage is almost always the most important metric for consumer app companies.

Link to the transcript of my PMF Convo with Ranjeet Pratap Singh

Now to the 16th episode.

This one was with Shubham Goel of Affinity the relationship intelligence SaaS play that has hit late stage eight figures $ ARR. Shubham co-founded Affinity when he was a college student at Stanford (along with his roommate Ray Zhuo). In this convo, he talks about how Affinity hit PMF or Product-Market Fit, through a distinct referral-led motion supported by strong customer success focus, and insane product love. He then covers his definition of PMF, why he thinks founders should talk to the founders 18m ahead of them (and not any senior founder), his recommended book on selling. This was a terrific chat. Every B2B / enterprise saas founder should read the transcript. It is a systematic guide to hitting PMF. Enjoy!

Link to the transcript of my PMF Convo w Shubham Goel.

Readings

Now to Part II of the newsletter where I share what I read and found interesting.

1 - Blume’s cofounder & Managing Partner, Karthik Reddy, and his Chief of Staff, Adithya Santosh, published the Omega Files, an x-ray of our Fund I performance. It is a never-before fund performance breakdown and deconstruction,  providing complete transparency of our Fund I’s investments and performance to a never seen before degree. If you are a student of venture capital, or practitioner, or aspirant, you will find it an incredibly useful resource.

Here is the chart of Fund I’s performance.

Here is a look at the educational backgrounds of our founders.

There are over 90 such fascinating charts in the Omega Files. Do give it a looksee!

2 - In 2020 or so, Sir Michael Moritz, one of the previous Stewards of Sequoia wrote a tribute to Don Valentine, the founder of Sequoia, who had passed away the year before. It is a private book meant mostly for internal circulation, as the tweet below shares. I finally got my hands on a scan of the book. Sharing it here for fans of venture history – Click on DTV or enter bit.ly/dtvbook into your browser.

Many of you know that I have been deliberately eschewing articles in favour of podcast transcripts (given the higher signal to noise ratio in these). That trend continues.

Here are five podcasts whose transcripts I enjoyed reading, with my learning notes on them. For the first podcast in the list below, I organised the transcript, as the podcast publisher doesn’t provide the transcript. You are welcome!

A/ Jason Lemkin, Mike Maples, Eric Paley & Harry Stebbings Debate on the 20VC podcast

Good listen for seed investors this roundtable (from Sep'23) Jason Lemkin, Mike Maples, Eric Paley and Harry Stebbings debating the seed market and what seed investing is, in today's context. What stood out for me - a) often the best investments at seed are non-consensus unloved (or misunderstood) bets b) Mulligan funds ("everyone in venture gets one Mulligan fund”). Clearly, 2021 vintage fund returns are not gonna be great and LPs will have to forgive & give a 2nd chance to GPs c) Mike Maples elaboration of PMF (“product market fit answers a very important but profound question, which is what can we uniquely do that people are desperate for?”). It is a good affirmation of what good seed investing is about, and a glimpse into the craft of classic seed investing from top tier practitioners of the venture craft.

Link to podcast and transcript.

B/ Andrew Roberts, historian, on the Dwarkesh Patel podcast

Good podcast episode covering war and conflict over the ages, with a deep dive into Churchill and Napoleon (whose biographies Andrew wrote). The big takeaways for me was how the first half of 20th century saw a lot of large multi-continent conflicts, but the second half didn’t see this trend (Vietnam, Korea, Afghanistan were largely local civil wars with another large state intervening) and the reason per Andrew is nuclear deterrence (talks about how Truman’s refusal to use nukes in the Korea war kept up the taboo on nuclear weapons) and how the existence of nuclear bombs forces wars to be fought on a narrower scale than in the past. Interesting look at Churchill as an emotive, principled (vs probabilistic, logical) thinker and Napoleon as an innovative, science-friendly leader. Has a fascinating para on Andrew’s working style that allows him to write these biographies (wakes up at 4am and writes / works till 9am on his books).

Link to podcast + transcript.

C/ Andy Raskin on the Lenny Rachitsky Podcast

Really good episode, and one that founders or aspiring founders of venture-backed startups should listen to / read. Andy describes how to create a strategic narrative, a simple story to help people understand why to use / back your product. A common failing is to pitch according to the arrogant doctor framework (you have a pain, and this product solves it, so use it). A superior framework is to position this product as part of a new way of solving the problem (“The world is changing. Here is where it is going. We will help you get there.”). In the podcast Andy provides a five-step playbook to craft your strategic narrative. A key step is naming the old and the new game through an evocative moniker. This is an insightful episode, and one I personally enjoyed given it plays at the intersection of strategy and marketing / narrative crafting.

Link to podcast + transcript.

D/ Brian O’Malley of Forerunner, on Acquired w Ben Gilbert and David Rosenthal

Forerunner is one of the leading consumer VCs and Brian gives us a glimpse of what makes them special - their focus on understanding the evolving U.S. consumer comes through. They do a fair bit of primary and secondary research to glean insights to figure out key themes in the life of the consumer. One interesting theme was rising spirituality. Through the interview, he gives a glimpse of what he looks for in the founders looking to raise from him (GTM thinking, a willingness to understand and use non-performance marketing channels to reduce CAC, an understanding of margin structures and unit economics) as well as how he helps founders he backs (asking the right Qs over helping them on operational matters). Overall a good podcast for an early stage investor, especially on the consumer side.<Insert Image>

Link to podcast + transcript.

E/ Charlie Munger, Berkshire Hathaway w John Collison of Stripe on Colossus’ Invest Like The Best

Enjoyable rambling podcast covering a range of Charlie Munger’s interests including architecture, politics, why having more kids at a younger age makes you happier, and of course finance and business models. A few points stood out to me.

Munger and Buffett care deeply about money at scale in the right way, which isn’t easy but it matters to them. Munger talks about how he doesn’t want to make money the way that Sacklers did by selling oxycontin, or FDR’s family made from selling opium in China, or by owning a toll bridge affording them monopolistic pricing powers.

They have their circles of competence when it comes to investing, and want to focus on that. Predictability of earnings emerges as a key investment criterion, which is why ideally little to no tech investing which runs the risk of getting disrupted, like Kodak or Intel. That said, they did invest in Apple, where they are the largest single shareholders. They love consumer brands or utility businesses like railroads for a reason. Even with railroads, he describes how they purchased it only because the US railroad system had consolidated into two, and there was scope for even more efficiencies to be wrung (by stacking containers atop each other).

Munger is a big fan of LKY who transformed Singapore. He reveals he has two busts of people - one is Ben Franklin and the other is Lee Kuan Yew!

Link to podcast + transcript. Link to my public notes.

Bye

It is time to wrap this! As I shared earlier, you should think of this substack as akin to a monthly magazine - you don’t have to read it all in one sitting, and you don’t have to read all of it!

That is all for now folks. Feedback, or your own ruminations, in the comments or at sp@sajithpai.com (Please don’t send pitches or CVs or anything work-related at my personal id; I may / may not respond to them; instead please use sp@blume.vc for pitches please).