On the venture side of the table: Aileen Lee from & from Precursor. My qualification for being there? A room full of Ausi’s needs a Kiwi.

We were in a board room discussing a song we just sat and listened to about Pigeons and how they were our first technology platform (Long story).

This is what I learned and what I shared.

“If Canva stumbles, you’re toast”

First surprise: The families think the USA is the answer and Australia is to busy promoting Canva.

One family office executive said it straight. Every Australian fund shows them the same names. Canva. You pay fees to concentrate into one company. His words about the local scene: you’re investing in a cocoon, and the innovation isn’t in the cocoon.

And here’s the number that makes it absurd. Australia has over A$4.5 trillion in super. It’s parked in US equities and bonds. But almost none of it touches US venture. The families have spotted the gap before their institutions have. That’s why they decided to be in San Francisco and not Melbourne.

The money lines up before the battle now

Charles has been investing in the Valley for 30 years. He said a few things have changed recently with AI>

It used to work like this. Every startup got a bit of money. They they fought it out. And the capital lined up behind whoever won.

Now the top 12 firms raise roughly two thirds of all venture capital. Andreessen went from not existing to the second biggest firm in the industry in 15 years. And when your fund is that big, a $10 million check isn’t a considered decision. So a founder asks for $5 million and gets told take 25. If 5 is good, 25 is better. It buy’s you time and it scares off your competitors.

What nobody says out loud is that none of that means anyone will ever want the product. The money lines up before the battle even starts.

One of the Australians sat through all this and said what everyone was thinking. This just sounds like a bubble. Nobody really argued. The honest answer from the room was that two things are true at once. AI is the biggest platform shift any of us have seen, and this generation of companies will have very few winners. The dot com boom built the internet we still use. It also killed nearly every company that raised in it.

The woman who invented “unicorn” has a new word

In 2013 Aileen wrote an essay that gave the industry the word “unicorn”. She has a new one. Zombiecorn.

The mechanics are simple. A pedigreed team like an ex OpenAI or ex Palantir, raises $25 million at $100 million pre. The company is only 3 weeks old. The founders are thrilled and they go and tell their friends.

What they’ve actually bought is a treadmill. The next round has to mark up from $120 million post, and enterprise software trades at about three times revenue. If growth isn’t insane there is no next mark. The bank balance keeps them alive for years. The cap table keeps them dead.

Aileen said something else that stuck with me. Before AI, 70% of her deals were pre product. It would be founders with a plan who needed money to build. Now nearly everyone she meets has already built something.

Deals are relationships, all the way down

A key stat of the discussion was the following: 40% of the deals in Charles’s last fund came from founders he’d already backed. Heading to 50%. He said that his best deal flow isn’t a process. It’s a thousand founders who had made money with you referring you, at the founder only dinner parties VC’s can’t get into.

Aileen’s shared a story about her investmetn in Drata. They were 2 brothers in San Diego. They had no cybersecurity background, they weren’t in the Valley, and everyone other VC passed for exactly those reasons. But what she saw was what they had was rage. They’d paid a consultant a fortune for a SOC 2 audit, done all the work themselves, and all they got was a stamp for it. They came to her because they wanted to automate the whole thing into continuous compliance. Cowboy put a chief security officers on it to review, the that CSO called it a better mousetrap, and Aileen led the round at about $15 million. Drata is now worth about $2 billion.

The lesson here isn’t about backing angry brothers. It’s that the deal was won on relationships and real diligence while everyone else pattern matched on pedigree.

What the room is hunting

Uranium. Seriously. America’s nuclear is built out has a fuel problem and startups that can find uranium in friendly territories are suddenly a venture category. The Australians loved this. They’re sitting on the stuff.

Robotics…. hmm careful. The contrarian view in the room was that China will win on robotics on cost of capital and manufacturing base, while the US investors pile in because every mega fund partner needs a swim lane and the themes have to be big enough to absorb the fund. Sit with that because the themes get’s chosen to fit the fund size.

Several families now have defense as an explicit thesis. Even small countries are moving budgets from ships they can’t crew to drones they can actually use. There’s a real opening for Australian and New Zealand money to co-invest alongside the the USA defense funds and bring the technology home.

Then it was my turn. What I pitched, and what happened when I finished.

The pitch I gave the room

Aileen and Charles were selling something families genuinely needed. Access to the power law, run by people with decades of pattern recognition. I can’t out credential that and I didn’t try. I pitched the thing I actually believe, built from ten years of being the founder instead of the fund.

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Here’s the short version of my pitch.

CAPITAL IS NOT THE ANSWER

Every time I ask a kiwi founder why American companies grow faster I get the same word back: capital. They’ve got more access to money.

It’s not wrong. I just don’t think it’s the answer.

In New Zealand we build businesses. In America they build positions. A business makes money from what it does. A position makes money from what it’s near.

There are two things American companies treat as assets that kiwis treat as overheads: influence and distribution. The best American companies trade both for ownership. Kiwi companies give both away for a discount on the invoice.

HOW I LEARNED THIS

In 2019, working on U2’s tour, I met Guy Oseary, Madonna’s manager and one of the real Hollywood powerbrokers. We took my original cup business, put real technology into it, and deployed it into the United States as TURN. We became the main supplier of packaging to Live Nation and replaced single-use packaging at Lollapalooza, Austin City Limits, Starbucks, Pepsi, Delta. At Austin City Limits alone we’d supply over a million products in a single day.

Which meant I spent four years watching how Guy and Ashton Kutcher actually operate.

LEVERAGE

There’s one word for how these people work: leverage.

In New Zealand we use that word for debt. In Los Angeles they use it for everything except money. Who you know, what you own, where you sit, who has to walk past your door. All of it is currency, and all of it gets spent.

When Guy and Ashton started their VC firm they rented office space at the front door of Live Nation’s headquarters. Every artist coming home from tour with a truckload of cash walked past their door first and asked the same question: what should I invest in? The office was the deal flow. Nothing they do is accidental, including the furniture.

When they wanted AB InBev as a client, they asked exactly one question about the CEO. Not his margins. Not his procurement cycle. “Who does he follow?”

They flew to New York with no pitch deck and brought the CEO’s favourite celebrity instead. They got the deal. Another time Ashton rang Howard Schultz directly, and two days later Starbucks was a client. Not a meeting. A client.

They didn’t spend a dollar on either deal. They worked out where they had leverage and spent access instead. Access, unlike money, comes back worth more than you paid for it.

THE LESSON

The companies that scale fastest don’t have the biggest cap table. They have the smartest one.

Most companies raise money and optimise for one number, the valuation, then spend five years wondering why no door ever opens. That’s dumb money. Dumb money is the most expensive money you’ll ever take, because you don’t pay for it in equity. You pay for it in years.

Ask one question of anyone about to join your cap table or your payroll: what happens the day after you sign that couldn’t happen the day before?

If the honest answer is “the money arrives”, you didn’t raise capital. You sold a piece of your company for cash.

WHAT LIVE NATION KNOWS

Pepsi once offered Live Nation millions to be the official drink of two hundred festivals. Live Nation said no. Instead they took a stake in a canned water company nobody had heard of, called Liquid Death.

That position is likely worth over two hundred million dollars today. Live Nation handed them the one thing no investor on earth could: a hundred and twenty million fans and every major venue in the world. Costco started calling Liquid Death. Traditionally it’s the drink company calling Costco.

Rapino didn’t sell them access. He kept a piece of what the access created.

I know this works because it happened to me. In 2022 Live Nation didn’t just take TURN on as a supplier, they invested. My single biggest customer bought a piece of my company. Doors that had been shut for two years opened in a week. We hadn’t got better overnight. Our customer had started making money when we won.

Vendors get managed. Owners get answered.

THE UNCOMFORTABLE BIT

Most established New Zealand companies are running the best savings account in the country. Twenty years of work, throws off cash every year. The American version of the same owner looks at the identical business and sees a platform to deploy.

You have distribution that can’t be bought at any price. Customers who trust you. Industry knowledge a twenty-two year old in San Francisco would give an arm for. Right now there’s a startup burning venture capital trying to reach exactly the customers you already have, and they would hand you equity for a phone call you could make for free.

Instead, most companies sign the supplier agreement and negotiate four percent off.

You negotiated four percent off. Live Nation took four percent of the company.

Here’s what taking the equity actually gets you, and the investment return is the smallest part. You get the equity. You get their technology running in your business before your competitors can buy it — that’s margin, this year. And when it works, you buy the whole thing at a price you understood two years before anyone else did.

Equity, margin, and an acquisition you’ve already test-driven. You don’t need to move to San Francisco or raise a fund. You change one sentence in one negotiation.

THE HIGHLIGHT

One rule underneath all of it, for your investors, your hires and your partners: choose them on distribution and leverage, not on cash and credentials.

I told the room my dad wanted me to be a lawyer and I wanted to sell cups. It took me twenty years and a term sheet from Live Nation to understand what that meant. It isn’t about who you work for. It’s what you own around you.

Would you rather have a million dollars, or a million people who can move your business forward?

Take the people. The money gets spent. The people compound.

Picture it. The biggest band in the world is about to play, the room is full of people who matter, and I’m explaining why my plastic cups are great to the guy who manages Madonna. Everyone is staring at us with the same question on their face: who the hell is that, and why did Guy pick him?

Fifteen minutes. That’s all I got. I walked out with my adrenaline going like I’d played the show myself.

The next time I saw him was at his office. And this is where it gets good.

Sound Ventures put their office right next to the front door of Live Nation’s HQ. Think about that placement. Every touring artist who comes home with a boatload of cash has to walk past Guy and Ashton’s low-key, relaxed little VC office to get to Live Nation’s front door. So they take a left instead right into Sounds Office and say. “Hey guys — what should I invest in?”

Guy and Ashton just found another LP in the fund. The office is the deal flow.

What I learned from Guy is that everything is strategic, he loves the strategy, and he is good at it.

One of the craziest strategies however may have been the couch in Guy’s office.

Guy’s room wasn’t big or fancy. Yet in it was one thing - A couch. Black leather, probably expensive. I didn’t think anything of it - until I had to sit on it.

The thing was LOW. Comically low. Hard to to get down onto, harder to get back up from. You’re standing there doing math while Guy is laughing and saying some joke: do I just drop into it? Do I turn my butt to the world’s most powerful music manager and lower myself down on one knee? Before you’ve said a word, you’re doubting yourself, wondering how stupid you look, most of all you’re feeling awkward as F***.

After speaking to a bunch of founders who also raised capital from Guy, I relised we had the same situation happen and the couch is strategic. It’s his office. Before you’ve even opened negotiations, you’re uncertain, awkward, and three inches off the floor. He’s got a leg up.

No pun intended.

That’s the thing about Guy. Psychology is everything. Nothing in that room is an accident, but it’s all subtle and you start to question was it strategy or was it just random. But its smart. The office next to Live Nation’s door, the couch, all of it. And I was lucky enough to have him as an investor.

[Video: Guy and me at Global Citizen Festival]

Guy took this video of us at Global Citizen Festival. I was catching up with him and his wife Michelle, both of us enjoying the fact that our company we started TURN was at the only festival ever thrown in Central Park — celebrities sipping out of our cups.

Here’s the weird thing about standing next to Guy. Everyone just keeps looking at you. The room is filled with want-to-be rockstars clocking me, because they are thinking if only Guy was my manager. Celebrities wondering what deal he’s cooking now. Proximity to Guy makes people assume you’re somebody.

When I started my first company, I wanted Guy Oseary as an investor. Not for fame. The math was simpler than that: get the world’s top music manager on the cap table, and every music artist in the world opens its doors.

The crazy thing is, visions come true and that is what happens when you have someone like him involved with you.

Here’s what standing next to him actually taught me.

Five minutes

Guy just did his first podcast ever, with Tim Ferriss, and dropped the line that explains everything I watched him do:

“90 percent of the things I do happen in the first five minutes.”

He signed Alanis Morissette off one song, after every label in town passed. Thirty million albums later, he was right. Muse flew from London to LA to showcase for him and he stopped them after the first song — “You do not have to play another song.” They wanted to keep playing. He wanted them to know he was already in.

And here’s the part people miss: it’s not recklessness. The five minutes decide whether there’s magic. Everything after is checking the thing actually works — “make sure the car actually shows up when you press the app.” He decides fast on conviction and verifies slow on execution.

Most people do the opposite. They agonize for three weeks over the gut call, then skip the boring verification. Guy would tell you that’s exactly backwards. When you’re the smaller player — smaller label, smaller fund, smaller checkbook — the fast, clear yes is the only edge you’ve got. “If I left it available, maybe someone will offer them way more money. I couldn’t afford to not make fast decisions.”

The jokes are load-bearing

Guy and Ashton also have this bit. Guy introduces Ashton: “Have you met Ashton? He’s the good-looking one.”

It’s funny. It’s warm. Everyone relaxes.

And it’s doing exactly what the couch is doing. You’re at ease, you’re laughing, and somewhere in there the question of who’s running this conversation got answered — and it wasn’t you. Self-deprecation from a guy that powerful isn’t modesty. It’s anchoring.

But the couch and the jokes are the warm-up act.

The single sharpest thing I ever watched Guy and Ashton pull off was the move they used to close some of the worlds largest Fortune 500 companies.

Here’s exactly what they would do.

🔒 The rest of this post is for paid subscribers.

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When Live Nation invested in my company, I thought I understood what had happened. My biggest customer had become my shareholder. Great outcome. Champagne.

It took me another year of sitting inside their organisation to understand what had actually happened.

Live Nation wasn’t doing us a favour. They were running a playbook. One that Michael Rapino — the CEO who controls Ticketmaster, owns more festivals than anyone on the planet, and has a relationship with virtually every major artist alive — has been running quietly for years.

Here’s the visible part of it.

For decades, the way a company like Live Nation made money from a brand like Pepsi was sponsorship. Pepsi writes a cheque, gets its logo on the stage, everyone shakes hands.

At some point Rapino did the maths and realised sponsorship is a terrible trade. You’re renting your most valuable asset — access to your audience — for a flat fee, while the brand keeps all the upside.

So in 2021 Live Nation did something different. They put money into Liquid Death — a canned water brand most people thought was a joke — and made it the exclusive water across their US venues and festivals. Over 120 venues. A hundred million fans a year walking past it at every bar and concession stand.

Liquid Death is now worth over a billion dollars. And every can sold at a Live Nation venue pays Live Nation twice: once at the register, once in equity.

That’s the part you can read in TechCrunch.

What you can’t read anywhere is what this playbook looks like from the inside — because I lived it. Live Nation ran the exact same play on my company. And once you’ve been the startup on the other side of that table, you see four structural advantages these companies are building that never make the press release, and a repricing happening across the economy that almost nobody has noticed.

That’s what the rest of this post is about:

• What actually changes the day your customer becomes your shareholder — the mechanics nobody talks about

• The four advantages corporates get from this that no VC on Sand Hill Road can ever get

• The numbers showing the serious money has already moved

• The three signals I now use to spot which industry gets repriced next

What Actually Changes the Day Your Customer Becomes Your Shareholder

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My own Family Office even called me asking for recommendations and ran a deep due diligence process end to end — I share exactly what funds they recommend in this post.

What you’ll learn in this post:

• How much you actually need to invest — and where to invest it

• Who you can invest in — the five fund “types,” in normal words

• How you can buy a house — Yes - rule changed in December

• (Paid subscribers, at the end) the exact shortlist of investments my family office took to final due diligence — and how to get warm intros to the funds, lawyers, tax advisers, and the real estate agents.

The whole thing, in one paragraph

It’s the Active Investor Plus visa (AIP) — New Zealand’s investor-residency route. Invest enough into approved NZ investments, hold for the required period, meet the immigration rules, and you get residency. Two lanes. That’s the entire game at the top level. Everything else is choosing the right lane, the right fund, and the right people — and not doing anything dumb with eight figures.

How much money: the two lanes

Picture two security lines at an airport.

The NZ$5M (2.8M USD) Growth line — this is the one most people ask about.
NZ$5M into higher-growth NZ investments, held 3 years, and you only need 21 days in-country over the whole period. Think private credit, venture, private equity, direct investment into NZ businesses, certain managed funds, and (from June 2026) up to 20% philanthropy. Lower number, shorter hold, more private and illiquid.

The NZ$10M (5.7M USD) Balanced line — more flexible, bigger cheque. NZ$10M , held 5 years, 105 days in-country (invest more, knock days off). Broader menu: bonds, listed equities, managed funds, eligible property development, plus anything on the Growth list.

The whole thing in one line:

$2.8M USD = private/growth. $5.7M USD = broad/flexible.

How to buy the house

This is usually the first emotional question. Can I eventually buy the New Zealand house?

If you get an AIP visa you can then buy or build a home — as long as it’s worth NZ$5M (US2.8M) or more.

So the dream version is real now. Do the visa, get residency, then buy or build. The “if things get weird, we have somewhere” plan. The visa is the paperwork. That’s the product.

Who you can invest your $2.8M USD in —
the five “types”

Open the approved-fund list and it’s a wall of names and PDFs. Ignore the names at first. Learn the five animals.

1. Private credit — “I want to sleep at night.” Your money goes into a fund that lends to NZ businesses and infrastructure — secured, for interest. Not buying startup shares and praying. Senior-secured lending, monthly income, real companies banks won’t fully serve. Not risk-free, and not a bank account — redemptions usually open only after a lock-up and stay at the manager’s discretion. But it’s the easiest story to understand.

2. Venture capital — “I want the upside.” NZ has more globally-minded growth companies than people expect — software, AI, climate, agtech, aerospace, health. Exciting, riskier, far less liquid.

3. Private equity — “real companies, not startups.” Established operating businesses. Buy good, professionalize, expand offshore, exit. For people who like business-building without lottery-ticket odds.

4. Infrastructure & real assets — “I want my money building something.” Energy, solar, food and fibre, tourism, forestry, property development. The tangible lane. Very New Zealand, because it is New Zealand — land, energy, exports.

5. Public markets — “the normal investor version.” Mostly the $10M Balanced path: listed shares, bonds, a familiar portfolio. More flexibility, bigger cheque, longer hold.

The team you actually need

You don’t start by picking a fund off a PDF. You build a team — in this order:

1. Immigration lawyer/adviser — confirms you qualify, runs the application.

2. Tax adviser — especially if you’re American. Residency and tax are separate problems that collide fast.

3. Investment adviser / family office — answers “what should I actually invest in,” which is not the same as “what’s on the approved list.”

4. Bank / FX / source-of-funds — the boring step that becomes the blocker.

5. Fund manager — the one actually deploying the capital.

6. Real estate agent — once you’re resident and ready for the NZ$5M+ house. The trophy-home market here is small and relationship-driven; the right agent sees places before they list.

Why this is worth the attention

Lots of countries sell visas. What’s different about New Zealand is it’s trying to make the money useful — capital into businesses, infrastructure, private credit, growth — instead of “buy an apartment and wait.” The pitch isn’t really the visa. It’s optionality: a second home country, a family hedge, a place that still feels sane.

The world’s getting weird. New Zealand was always the joke escape plan. Now it has the paperwork. Its a little like joining a private club, you can join but only if you have the money.

For paid subscribers I have narrowed dozens of approved funds to a shortlist, took a handful to final due diligence, and built the team around it. Below, for paid subscribers, is exactly which funds my family office shortlisted — plus how to get warm introductions to those managers. You can contact me if you are interested in who I would recommend as an immigration lawyer, a US cross-border tax adviser, and the real estate agents who actually handle New Zealand’s NZ$5M+ homes.

If you’re even half-serious about a NZ Plan B, this is the part worth the subscription.

🔒 The Shortlist (Paid Subscribers)

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The event was Humans in the Loop, hosted by of . The setup was simple but brilliant: 23 of the world’s top venture funds including , Y Combinator, , and 20 others, together managing over $100 billion — were each allowed to nominate exactly one startup to pitch on stage.

Not their whole portfolio. One company they’d put their name behind.

When a VC who sees thousands of companies a year is forced to pick a single one, that pick tells you what they really believe. So this wasn’t a demo day. It was a map of where the smartest money thinks the world is going.

Here’s what I saw.

The man who almost deleted ChatGPT

The headline guest was Nick Turley, the OpenAI executive who runs ChatGPT as a product. A billion people use the thing. He manages it.

Here’s the part almost nobody knows: ChatGPT was supposed to be deleted after 30 days.

It launched as a throwaway demo. The team didn’t think it deserved name. The plan was to shut it down after a month because OpenAI couldn’t afford to run it for free. It only exists because users kept ignoring what OpenAI built and using their tools for everything else.

Turley’s advice to every builder in the room came down to one question: “How does my product get 10x better when the AI gets 10x smarter?” If the answer is “it doesn’t,” you’re building on sand. Even OpenAI kills its own features when they fail this test.

What the smartest money is betting on

Twenty-plus startups pitched. Almost none of them will sound like “AI companies” to you. That’s the point. Every single one started with an everyday problem you’d recognize:

Your to-do list. Town is building an AI assistant that lives in your email and quietly handles the boring stuff — booking, forwarding receipts, prepping meetings. Their pitch: LeBron James doesn’t register his own kids for summer camp at 5am. Someone does it for him. Everyone deserves that someone. (Two major funds just put $55 million behind it.)

The school calendar. Otto, made by Indexed Labs, watches your email and the school websites so parents stop missing early dismissals and spirit days. The founder’s stat: 60% of school weeks are “nonstandard.” Every parent in the audience nodded.

The doctor you can’t get in to see. This was the boldest one. Doctronic convinced the state of Utah to let AI renew prescriptions — something that’s never been legal anywhere. Turns out 75% of all prescriptions in America are just renewals. After five months: the AI agreed with human doctors 97% of the time, with zero bad outcomes. The founder, a practicing surgeon, put it simply: there will never be enough doctors — but now that’s a computing problem, and computing problems get solved.

The tutor most kids never get. Aristotle offers unlimited one-on-one AI tutoring for $299 a month — in a country where only 1 in 50 kids has a tutor at all. Kids are voluntarily doing 50-minute sessions. One parent canceled their $250-per-hour human tutor.

The trip you never have time to plan. Odessia — built by the founder of Sonder — planned and booked an entire weekend in Mexico City live on stage in three minutes. Flights, hotel, restaurants, museum tickets. The average trip takes 14 hours to plan.

The home that runs itself. Casa gives every homeowner what rich people have: a property manager who knows your house and “knows a guy” when something breaks.

And then there were the wildcards: a startup where the AI builds an entire movie studio around your idea (Dollhouse — their cost to generate video is now about 10 cents a minute), and a social app called Sekai where instead of posting videos, people post little apps they made by just describing them. Its users created 15 million apps in six months. Apple’s App Store took 17 years to reach 2 million.

The line of the day

Between pitches, — a longtime tech executive who now runs her company called ChatPRD almost entirely with AI agents and one part-time human — was asked what will still matter when AI can do everything else.

Her answer: imagination, conviction, and charisma. Or as she tells her kids: “Rizz is the only moat.”

AI can refine ideas and grind without getting tired. It can’t decide what’s worth building, and it can’t make people follow you. That’s still ours.

The full roster — every pick, one line each

For the completists (and the founders studying what top funds want), here’s every company that took the stage:

1. Town (First Round + Forerunner) — an AI assistant that lives in your email and handles your busywork

2. Indexed Labs (Otto) (NEA + Adverb) — never miss a school pickup, spirit day, or camp signup again

3. Corner — a map app that learns your taste, so recommendations actually feel like yours

4. Pax Historia (Y Combinator) — strategy games where AI writes history live: “What if Germany won WWI?”

5. Dollhouse (South Park Commons) — type an idea, get a whole film studio: script, storyboard, rendered video

6. Doctronic (Lightspeed + Union Square Ventures) — the first AI legally allowed to renew prescriptions in America

7. No Logo (Greylock) — turns a creator’s product idea into real manufactured goods in a month

8. LeLamp — robot characters for your home, built for personality before chores

9. Odessia (Sequoia) — plans and books an entire trip in 3 minutes instead of 14 hours

10. Mother (GV) — a private vault of everything you’ve ever created, that works for you instead of advertisers

11. Wabi (backed by a16z) — make your own apps by describing them, share and remix like YouTube videos

12. Casa (Adverb) — a personal property manager for every homeowner, not just the rich

13. Era (Abstract) — the brains for a coming wave of small AI gadgets (their demo: a talking bag charm)

14. Aristotle (True Ventures) — unlimited 1:1 tutoring for kids, $299/month, available at 11pm before the test

15. Extra (Felicis) — your inbox reorganized around your life instead of everyone else’s asks

16. Alta (Menlo Ventures) — an AI stylist that knows your closet; #1 in the App Store in a dozen countries

17. Sekai (A*) — a social app where people post mini-apps instead of videos; 15M made in 6 months. is a legend.

18. Moda — demoed in the final block (by Anvisha Pai)

19. Clearspace — helps you take your attention back from your phone

20. Innate — teachable personal robots for the home

21. Poke — an AI assistant you just text; first AI agent approved on Apple’s Messages platform, built by the guys who won Elon Musk’s tunnel-digging competition

22. Monogram — Udemy and Carbon Health founder Eren Bali’s third act: building the interface for AGI itself

Twenty-two companies. Not one enterprise tool in the bunch.

What it all adds up to

Not one of the 23 funds picked a company building a better chatbot or a tool for corporations. Every single bet was on regular life: school pickup, prescription refills, homework, trip planning, a broken water heater.

The host, Kirsten Green of Forerunner, opened the day by saying that outside San Francisco, fear about AI outweighs excitement — and that the story won’t be changed by arguments. It’ll be changed the first time these products quietly fix something real in your week.

After watching twenty demos, I believe her.

About that prize

One more thing. The event ran a contest across all thousand attendees: who’s using an AI agent in the most creative way?

I won. There’s a new Mac Mini sitting on my desk to prove it.

What did my agent do to beat a thousand of San Francisco’s best builders? It’s right below this button.

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Here it is:

I built an agent that texts me when three things are true at the same time — a container ship is entering or exiting the San Francisco Bay, the wind is over 20 knots, tide is ebbing, and the sun is out.

Why? Because when a ship that size moves through the Bay, it pushes a wave. And if you time it right, you can ride it.

So while everyone else’s agents were summarizing meetings, mine was watching ship traffic and weather data — waiting to tell me when to drop everything and go surf the wake of a container ship.

That’s the thing about this technology that no keynote can teach you. The magic isn’t that AI can do your work. It’s that it can watch the world for moments you’d otherwise miss.

What would your agent watch for? Reply and tell me — best answer gets a breakdown of exactly how I built mine.

And if you’re building something in this vein — or arguing with my read on any of these bets — reply. I read everything.

What I expected: a polished investor talking about renewables and solar power.

What I got: a surprisingly candid, almost urgent account of why the next decade of investing looks nothing like the last one — and why the serious money is finally moving in ways most people haven’t noticed yet..

“We’ve Never Seen This Level of Unpredictability. Never.”

Generation has been around for 23 years. Through financial crises. Through political whiplash. Through every tide going in and out on climate.

They were not just talking about Climate, they were talking about politics.

The world is fracturing. America First. De-globalisation spreading like a virus across governments everywhere. Countries no longer trusting that global trade, global capital, or global institutions will be there for them when things get hard. The result: every nation is turning inward, trying to secure its own food, its own energy, its own supply chains — regardless of whether that’s economically efficient.

That political reality is what makes climate investing so hard right now. And, paradoxically, so important. Because when governments stop trusting each other, the only capital that flows freely is the capital attached to local strategic priorities — which is exactly where climate infrastructure sits.

“If you lose control of both of those things,” he said — AI and climate — “you basically lose control of warfare.” Uncontrolled migration. Countries purely looking after themselves. The de-globalisation playbook playing out everywhere at once.

That’s the context in which he’s deploying capital. Not a thesis about solar adoption curves — a thesis about what holds civilisation’s together when the old rules stop applying.

Sovereign Wealth Funds Are Turning Inward — And That Changes Everything

Here’s the structural shift that I think most founders and investors are sleeping on.

The largest pools of institutional capital in the world — sovereign wealth funds — are growing. It’s one of the only categories of institutional capital that is expanding right now. And they’re doing something new: they’re turning inward.

Colin described mandates arriving from New Zealand, Ireland, the state of Victoria in Australia, Brazil’s development bank BNDES — all with the same underlying demand: “What are you going to do for our food system? What are you going to do for our housing market? What are you going to do for our local energy?”

This isn’t “ESG investing.” This is capital with a strategic mission attached: protect citizens, protect food systems, protect energy security. The big LPs, as Colin put it, are funding climate “because it helps us de-risk the system and gives us optionality.”

Capital is becoming geographically anchored in a way it hasn’t been in decades. For anyone building in climate, energy, food, or infrastructure — understanding which sovereign backs which mandate is now a core strategic skill.

Oh, plus they want this while also seeing large returns on their capital.

The Steel Story That Blew My Mind

This was the specific example I haven’t stopped thinking about.

Steel causes 7-8% of global emissions. The reason is structural: old steel plants were built next to permanent (high-emitting) energy sources. You can retrofit them and cut emissions 30-40%. But you can never get to zero that way. To get to truly zero-carbon steel, you have to build new plants from scratch, next to 24/7 renewable energy.

That’s exactly what Stegra (formerly H2 Green Steel) is doing — building a €10 billion green steel plant from scratch in Boden, northern Sweden, next to renewable power. Generation is the biggest funder. The plant is 60-70% built and will start producing steel next year.

What unlocked the financing? Off-take agreements. The big tech companies and car manufacturers committed to buying only truly zero-carbon steel — not “slightly less dirty,” but genuinely zero. That commitment unlocked the European Investment Bank, the Swedish Export Agency, pension funds — the whole capital stack.

Then, nine months ago: a €1.4 billion cost overrun. As Colin told it, bluntly: “Shit, this is gonna go down.”

Everyone remembered Northvolt — a Swedish battery factory that collapsed — and the real question hanging in the air was whether Europe could actually build large-scale infrastructure at all anymore.

The Wallenberg family (Swedish Industrial Family) stepped in. Their thesis: “We can’t let this fail. If this fails, Europe never raises money for big projects again.”

The lesson Colin drew from it wasn’t about green energy. It was about what climate investing actually requires:

“You’ve got to work with the government, you’ve got to work with other investors, you’ve got to work with the banks, DFIs, endless amounts of people. This is what climate investing at scale actually looks like — it is real economy infrastructure development.”

While US Investors Debate, China Is Building Toll Roads in Africa

Here’s the part of the conversation that stuck with me most uncomfortably.

While Western investors — constrained by regulation, politics, ESG committee sign-offs, and endless due diligence — are still figuring out how to deploy capital into emerging markets, China just... builds things.

Toll roads connecting Nairobi to the airport. Ports in Mombasa. Rail networks across the continent. Not through funds and term sheets — through long-term concession agreements and debt deals that give China physical assets and lasting influence in exchange for infrastructure that actually gets built.

The best part - The signs are all in Chinese.

The uncomfortable truth Colin was pointing at: the complexity that makes Western capital “responsible” also makes it slow. And in the race to build the infrastructure of the next century — in Africa, in Southeast Asia, in Latin America — slow means absent.

This isn’t an argument for abandoning standards. It’s a wake-up call about what it actually takes to compete. The countries and investors who figure out how to move with speed and integrity in these markets are going to own the next chapter. Everyone else is going to watch China do it and write think-pieces about why it’s problematic.

The thing that keeps echoing in my head is this reframe: the bottleneck isn’t technology anymore.

Solar works. Wind works. Zero-carbon steel is being built right now. The bottleneck is orchestration — the ability to align governments, capital, industrial buyers, and policy simultaneously so these things can actually get built and scaled.

Colin was explicit: getting these projects done requires “a completely different muscle, a completely different type of setup as an asset manager.” Early-stage venture instincts don’t transfer. You need industrial coordination at scale.

For founders, I think the version of this that applies to us is equally important: the biggest opportunities in the next decade sit at the intersection of public infrastructure, sovereign capital, and private enterprise. The founders who learn to operate in that space — who can speak to governments and pension funds and industrial buyers in the same breath — are going to build things at a scale most of us haven’t imagined.

We’ve been trained to build in isolation, to move fast, to avoid dependencies. That instinct served us in software. It won’t serve us in the decade ahead.

One More Thing: Watch the Steel Giants

If you believe zero-carbon steel is coming — and after hearing Colin, I do — then the world’s largest public steel companies are worth watching right now. These are the players with the scale, customer relationships, and infrastructure that will either adapt and dominate or get left behind:

⚠ Not financial advice. Performance estimates are approximate based on publicly available data — do your own research. Asian names in particular are affected by currency moves so treat as directional.

The old playbook said: find the best return. The new one says: make sure the system you're investing in still exists when you go to collect. That's not pessimism. That's the most important investment insight of the decade — and most people are still asleep on it.

The serious money doesn’t move loudly. It moves early. And it’s already moved.

Last month, I had dinner with a GP at a $750M AI-focused fund.

Early VP at Google.
Worked alongside Sergey Brin when Google was still building the rails of the internet.

I asked them a simple question:

“How do you decide what to invest in with AI right now?”

They didn’t hesitate.

“The ones that own data no one else has.”

Not the flashiest demo.
Not the biggest model.
Not the best pitch deck.

The ones sitting where real world behavior happens.

Here are three examples they shared.

1. The Company That Sees Every AI Decision

Chalk powers real time AI systems.

Fraud detection.
Loan approvals.
Pricing engines.

They sit in the middle of those systems.

Which means they see:
Who was approved
Who was rejected
What signals mattered
Where the model changed

Millions of live decisions.

Over time, they don’t just power AI.

They understand how AI behaves in the real world.

That dataset doesn’t exist anywhere else in one place.

2. The Company That Sees How AI Actually Runs

d-Matrix builds chips designed for running AI.

They sit below the model layer.

That means they see:

Where inference slows down
How often systems fail
What real workloads look like at scale
Which architectures actually perform

This isn’t benchmark data.

It’s production behavior across customers.

You cannot scrape that.
You cannot simulate that.
You have to be inside the system.

3. The Company That Owns the Lab Results

Chemify automates chemistry experiments.

Every experiment is structured digitally.

Every result becomes clean, usable data.

Over time, they build a living database of:

What combinations worked
Which ones failed
Under what conditions

The more experiments run, the stronger the moat.

You cannot shortcut the experiments.

You have to run them.

The Pattern (In Plain English)

All three companies sit:

Where decisions happen.
Where experiments happen.
Where money moves.

They aren’t just tools.

They are data positions.

AI models will commoditize.
Infrastructure will get cheaper.
But unique data compounds.

That’s the bet.

Then they said something that stuck with me:

“Most founders are trying to build smarter models. The smarter founders are trying to sit where new data is created.”

So I started thinking:

Where is valuable data being generated every day — and who owns it?

What Would You Fund Tomorrow?

I asked them one more question.

“What’s a business I could start tomorrow that you would fund?”

Read on to learn what AI business you could start that would get the backing of a $750M AI fund.

Read more

When the inspection report came back on the Miami truck, the seller went quiet.
Before that, it was “clean.”
“Dry climate car.”
“Sorted.”

On paper, it was perfect.

On a lift, it was a different story.

Frame rust. Cooling shortcuts. Cosmetic coverups hiding bigger problems.

Two hundred dollars for the inspection saved me what could have been a six figure mistake.

It took me over six months to find the right truck. I looked in Ohio. I looked in Miami. Both failed inspection. Both were represented as well sorted.

I almost bought them.

Here’s what I wish I knew before buying a Range Rover Classic.

1. Always Get an Inspection. Always.

I do not care how reputable the seller is.
I do not care how clean the photos look.
I do not care how compelling the story is.

Get a proper third party inspection from someone who understands classic Land Rovers.

These trucks can look incredible and still hide serious issues underneath.

If you want to see what a real inspection report looks like, book a call with me. I will show you the exact reports that nearly fooled me.

That $200 was the best money I spent in the entire process.

2. Gas vs Diesel Is Not a Small Decision

We ultimately chose a manual diesel.

The V8 gas trucks sound fantastic. But they are known for cooling issues, head gaskets, and layered electrical quirks from 1980s engineering.

The diesel is slower. No question.

But it is simpler. More mechanical. More tractor than sports car. And paired with a manual gearbox, it transforms the driving experience.

It feels honest.

If you are buying this for speed, stop here.
If you are buying it for character, keep going.

3. You Are Not Buying Luxury. You Are Buying Charm.

The Range Rover Classic was once the definition of luxury SUV.

Today, it is a leather lined farm tool.

It is slow.
It smells faintly of oil sometimes.
You will watch the gauges more than you expect.
A diesel may see 20 to 30 mpg if you are lucky. The V8 will not.

But the view is extraordinary.

The glass is massive. The seating position is high. You feel like you are driving a greenhouse on wheels. It has presence without shouting.

Modern Range Rovers feel like tech products.
This feels like machinery.

4. If You Are Tall, Solve It Early

I am 6 foot 7.

Stock seat rails were not going to work.

After getting nowhere trying to find answers, I found a custom solution from Tom Beaton at Tiro Mechanical Design Solutions that extends the seat travel.

It completely changed the usability of the truck for me.

If you are tall, plan for this from day one. Otherwise the romance wears off quickly.

5. It Will Take Longer Than You Think

I assumed I would find one in a month.

It took six.

You are competing with nostalgic buyers, Instagram dreamers, flippers, and people who watched too much Camel Trophy footage.

The right truck exists. But discipline is everything.

Walking away is power.

6. Buy From People Who Actually Live in This World

We ultimately bought a Stray Dog Classics import from New York. We were its second owner.

It was not cheap. Most of them are over $80k USD.

But after navigating sellers who were cutting corners or hiding issues, paying for transparency felt better than chasing a deal.

They documented it properly. They were open about flaws. They understood what they were selling.

That matters more than a glossy listing.

7. This Is What It Actually Costs

This is not a hobby you casually fund.

Maintenance

Plan on roughly $5,000 per year in maintenance.

This is not exaggeration. Some years will be light. Some will hurt. But if you are not prepared to spend money on it, do not buy one.

Upholstery

In San Francisco, expect:
Around $200 per seat for repairs
Around $800 for a full seat recover

Leather cracks. Foam collapses. It is normal.

Paint

Sun damage is common.

We were quoted:
$1,000 for a boot repaint
$1,500 for a hood repaint
$2,000 for roof repaint.

Touch ups are for free ;)

Parts

The good news is parts are surprisingly available. You can source a large amount through eBay and specialist suppliers.

The bad news is you will become very familiar with them.

8. You Will Talk to Strangers. Constantly.

Fuel stops turn into conversations.

Parking lots turn into photo shoots.

Everyone has a story about a Land Rover.

You are not just buying a vehicle. You are buying a moving conversation piece.

9. This Is Not Rational

If you want reliability, buy a Toyota.

If you want modern comfort, buy new.

If you want something that feels like a mechanical time capsule that can still climb a mountain and makes you feel something every time you start it, this is your truck.

It is slow.
It is thirsty.
It is imperfect.

And it is incredible.

If You’re Thinking About Buying One

I still have the inspection reports from the Ohio and Miami trucks that almost fooled me.

If you want to avoid the same mistakes, you can book a call with me here:

https://app.hubble.social/ryaneverton

I am happy to walk you through what to look for, what to avoid, and whether a Range Rover Classic is actually right for you.

Subscribe now

For some reason, that planted a dangerous thought:

Why not buy a sailing team?

That curiosity led me to explore buying the New Zealand SailGP team, the Black Foils.

I met with Peter and Blair from the Black Foils. I spoke with owners of other SailGP teams. Some had built and sold very large companies. I spent hours with a former CFO of the America’s Cup. I ran scenarios, downside cases, and walked through what failure would actually look like.

During that process, I learned more about business than I expected.

Not from decks or models, but from the owners themselves.

Each owner I met, I asked a simple question:

“How do you decide what’s worth backing?”

These are two things that stuck with me.

Lesson #1: Back #2. Let #1 Die Teaching You.

One owner told me about his best friend at UCLA.

That friend didn’t invent rollerblades.

He bought the company after it failed.

The original business had burned capital on R&D, marketing, education, and distribution. The product was early. The market wasn’t ready. The company collapsed.

Everyone else saw a failure.

He saw something different.

He saw a team that now knew exactly why the business didn’t work.

What he really bought wasn’t rollerblades.
It was earned knowledge.

The team understood:
• what customers rejected
• which assumptions were wrong
• what features mattered
• what didn’t
• and why timing killed the first attempt

With fresh capital and better sequencing, that same team rebuilt the category.

Rollerblading as we know it today came from the second attempt, not the first.

Then he leaned back and said:

“It’s much easier to back number two than to be number one.”

After a failure, most people panic.

They decide the product didn’t work.
The idea didn’t work.
The market didn’t work.

What they miss is that the team has just spent years and millions learning exactly what would have worked.

If you can get past the noise and the stigma, that’s the opportunity.

The failed teams understood where the market pushed back, what broke, and why the first attempt failed.

That pattern showed up repeatedly for the owner I spoke with.

He had 3 billion-dollar businesses he helped start and sold and all were created by backing teams and products that failed the first time.

The lesson is simple:

Back #2, don’t be the first to market.

But the second lesson is the one of the most valuable business lessons I have ever learned.

Subscribe and read on below to learn my second lesson.

Read more

I had dreamed of this moment for years. The CEO of the largest entertainment company on the planet wanted to invest in my company.

For so long I had been grinding away trying to get festivals to use us. Emails ignored. Calls cold. Rejections. All of it.

I used to think if I could just get Live Nation behind us, everything would get easier.

That call came when I was in Tampa Florida. One of my advisors Jerry Diefer had dragged me to go visit a casino - The Hard Rock casino.

But my luck that day didn’t come from a slot machine covered in cigarette smoke. It came from a phone call from the most powerful music company in the world.

People keep asking me how I got Live Nation to invest in my company.

So I decided to write about it below.

Read more

In the 1800s you needed land to start a business.
In the 1900s you needed a factory.
In the 2000s you needed to know software.

In 2025, the requirements change again.

Airbnb is worth more than the Marriott and Hilton groups combined yet it never bought real estate.

Ownership is not the moat anymore.
Thinking is the moat.

AI gives us the ability to think with more clarity, speed, and range than ever before.

Today, I can run one company & Elon could run five.

If everyone will be 100x more productive, I could run 100 companies, while Elon could run 500.

We are stepping into a time where the primary constraint is not intelligence, or capital, or time.

The constraint is imagination.

The New Entrepreneurial Equation

For two decades, the formula for starting something looked like this:

Have the idea
Raise the money
Hire the team
Ship the product

That formula is dissolving.

Today, a lot of founders are intelligence-constrained.

AI will cut the cost of starting a company by replacing many early hires.

If intelligence is no longer scarce
and capital is no longer scarce
and execution is no longer scarce

what is left?

Read more

I think about all the days I was unhappy.
Too tired to go to an event.
Stressed out of my mind.
Busy.

At 20, I was sleeping on someone’s couch on an island in Mexico with a friend I met a week earlier at the airport.
At 22, I walked into a bar and met the most beautiful person I had ever seen. She is now my wife.

Lately I have started having visions of my 5 year old self.
Running on my family farm.
Bumping into farm workers on motorbikes.
Smelling silage while watching my dad bale hay.

Who am I?

suggests asking this question “Who am I” to move beyond the conditioned identities we cling to: our jobs, our families, our passions. The question helps us discover what is deeper than all of that.

Am I Ryan, the 5 year old running on a farm in New Zealand.
Or am I Ryan at 18, drunk at law school.

As I get older I worry that in todays world too much of who I am has been handed out as fragments to other people’s memories.

It is easier to stare at a photo of stars than to go outside and look at the sky.
It is easier to send someone a picture of food than invite them to dinner.
It is easier to call my parents than for either of us to get on a plane.
It is easier to read a quote about who you want to be than to become that person.

My world used to be explored.
Information was shared over coffee.
Books.
Nanna.
I bumped into people.
Life felt coincidental.
It was coincidental.
It was magical, random, unknown.

Scared to move so far that we no longer recognize the person we have been calling I.
Scared that people might stop loving us because they love who we were, not who we might become.

I learned recently that humans prefer the pain we know to the joy we do not know.
And that becomes something psychologists call repetition compulsion.
When we unconsciously recreate past trauma or unhealthy dynamics even when they hurt us.

To face this is terrifying.
These patterns scarcity, fear, guilt, anger, desire pass through generations, becoming so unconscious we think they are us.

We judge others through these unconscious biases.
Projections of who we are and who we are afraid to be.

So the question becomes:
Is who I am actually the person I need to unlearn.

The more I live, the more I believe we should in our lifetime explore every version of ourselves.

And when we look back, we move past unconscious limiting beliefs, false messaging, and codependent people pleasing.

And we abandon it.

It is terrifying to look at yourself and ask,
Is this really who I am.

But the more time I spend doing the work, the more I see how much of my life was built on repetition compulsions and not on who I really wanted to be.
Unconscious loops about who I thought I should be instead of consciously choosing who I am.

And when I look around me, I realize many of the people in my life are here because of those loops.

Stressed.
Anxious.
Worried.
Uncertain.
Searching.

I realized the life I am living and the people in it are tied to who I was.
And that became who I am.

And this is where founders get stuck.

We build companies from the part of us we have not examined.
We build from fear.
We build from scarcity.
We build from the version of ourselves we were taught to be.

And then we wonder why we feel disconnected from the thing we created.

To be an intuitive founder is to return to who we actually are.
Not who we learned to be.
Not who we think we need to become.
Not the version of ourselves that earns approval or funding or praise.

It begins with meeting the one person we avoid. The person we need to love the most.

Who I am.

They said “The money will be wired on Monday.”

I said “Thanks, Kush.”

It cost me over $300k in legal fees to close the deal. I was sweating.

And then Monday came. I checked our bank account. No money.

This is what it’s like to have an investor wanted by the FBI.

Read more

Somehow, I’ve always met the exact people I needed to meet.

When I was nineteen, drifting through a law degree I had no interest in, I met a guy who had managed billions for Steve Jobs in the early years. We were sitting in a café and he looked at me and said:

“You only have a short time to live, so do something that makes the world better.”

Read more

From growing up on a farm and selling meat pies at boarding school during the tuck shop prohibition — to tackling global plastic waste, building infrastructure to wash a million cups at a time (literally) … Ryan’s journey embodies Kiwi ingenuity and entrepreneurial spirit.

In this episode, we explore:

* TURN’s origins as “Globelet” .. and ideation journey through the Otago University “Audacious” business competition.

* The journey from landing his first festival customers, through to partnering with Live Nation and rolling out across 36 festivals on the same contract… now on to Starbucks, Chick-fil-A.

* How TURN achieves >90% cup return rates at events - building loyalty programs, rolling out powerful incentive mechanics.

* Navigating the pandemic - seeing it as an opportunity to take stock, invest in R&D and rebranding, automating washing infrastructure, come out swinging on the other side.

* Riding regulatory tailwinds — coming California restrictions on single-use plastics, and how they’re positioning themselves to ride them.

* Unlearning classic Kiwi habits to lead a global team.

* Why grit is an important founder trait, and where he thinks it comes from (hint: back on the farm).

* Philosophical reflections on purpose, success, and leaving a legacy

Where to find Ryan online:

* LinkedIn: https://www.linkedin.com/in/ryaneverton/

* Twitter/X: https://x.com/Valueroad

Make sure you subscribe for more epic expat stories every Friday!

Enjoying Diaspora.nz? Share this episode with a friend or family member:

This is a public episode. If you would like to discuss this with other subscribers or get access to bonus episodes, visit www.diaspora.nz

There are the ones who think the job is to push forward: to act, to build, to force the next version of their life into existence through sheer momentum. This is the founder archetype most of us identify with—the grinder who keeps going when others stop, who creates opportunity where there is none, who wills things into reality.

And then there are the other builders.
The ones who excavate.

Their work is not to push forward but to uncover. They move through life like archeologists: brushing away the sand to reveal what already exists beneath the surface. Their mastery is not in force, but in perception.

I feel like the greatest builders in history (those who erected the pyramids, encoded cosmic frequencies in stone, left behind architecture that refuses to yield its secrets) were excavators. Not because they were digging into rock, but because they were digging into themselves.

Its time that we all start doing the second type of building.

The building that doesn’t come from force, but from awareness.
The building that doesn’t happen “out there,” but “in here.”
The building that begins not when you add more to your life, but when you finally remove what’s been covering it.

This question is so simple it feels dangerous:

What if your highest potential isn’t something you create, but something you uncover?

A few days ago, I sat down with a guy.
A guy who worked for Marc Benioff before he even bought the domain salesforce.com.

He’s one of those rare people who can look at the same market everyone else sees —
and somehow spot the invisible layer of opportunity beneath it.

We talked about a gap that almost no one is talking about — the <$10M investment bank opportunity.

Traditional investment bankers chase $100M+ deals.
VCs chase billion-dollar outcomes.
But between those worlds lies a golden window: the sub-$10M transactions that are happening (or should be happening) every day — startups building fast with AI, incumbents desperate for tech, and nobody connecting the dots.

Why Now

There are two forces creating this window:

1. Distribution: Incumbent companies are now the fastest and cheapest path to customers.

2. Product: AI has made it faster and cheaper than ever to build.

The result?
An explosion of small, high-value products — and a growing demand from larger companies that can’t build fast enough but have reach, customers, and cash.

That’s where the opportunity lies.

Distribution: The Game Changed

Five years ago, if you wanted users, you ran Meta or Google ads. It was simple. Those platforms had the data, the targeting, and the scale.

It was cheap, addictive, and it worked — until it didn’t.

They got you hooked, then raised prices until your margins disappeared.
Now, every investor asks the same question:

“How will you get users?”

And the answer can’t be, “We’ll run ads.”

That era is gone.

Today, distribution is trapped inside incumbents — big companies that already own the customer but can’t innovate fast enough. They have trust, channels, and scale. What they don’t have is product velocity.

That’s the bridge.

Product: AI Has Collapsed the Cost Curve

Building a product used to take millions and a team of engineers.
Now? Two people and a weekend with AI tools can ship an MVP.

The cost of creation has collapsed.
The cost of attention has exploded.

That dynamic has flipped everything.

Small teams can now build better products faster than enterprise can move — but they can’t reach customers at scale.
Enter incumbents. They need this tech yesterday.

The New Investment Bank

If the old investment banks brokered billion-dollar mergers, the next generation will broker micro-acquisitions.

Sub-$10M deals.
Founders building fast, corporates buying faster.
Hundreds of niche AI tools, data products, and automation layers waiting to be matched to the companies that need them.

There’s no Goldman Sachs for this layer.
No one connecting the buyers and the builders.
That’s the $10M investment bank opportunity.

How to Capture It

Two plays:

1. Build → Sell
   Identify where incumbents lack tech, build quickly, validate with users, then sell before scaling headaches begin.

2. Broker → Connect
   Act as the bridge — find the startups building gold and the companies desperate to buy.

Either way, this space is wide open.

My friend called it a golden window. A once-in-a-decade window.
He’s right.

The incumbents have the distribution.
AI has collapsed the product timeline.
And what sits between them is a market no one is serving — yet.

That’s the <$10M investment bank opportunity.

Read more

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“Is he actually smart?”

Here’s the truth.
------

Every call I had with Ashton and his partner Guy Oseary (Madonna’s longtime manager) would eventually land on one question:

“What’s our leverage?”

Then came the ping-pong:

“Don’t we have leverage here?”
“No, they do — because of X.”
“Can we build leverage by doing Y?”

It became a habit. A mindset.

And it changed how I think about business.

If you want better pricing, faster decisions, or stronger partnerships. If you want to win deals, get investors, anything. You need leverage.

People don’t act just because they like you.
They act when you have something they want.
Now, I ask myself this every time I do something:

What’s my leverage?

So… is Ashton Kutcher smart?

I would say he was smart enough to teach me one of the most important lessons in business. Leverage.