Photo by S O C I A L . C U T on Unsplash

It continues to strike me, the more and more I speak with individuals across Canada (and around the world, too) how desperate we all are for a better way. A better way to manage our health and wellness journeys.

It occurred to me this week that this is actually the third time I’ve tried my hand at solving a problem for people through starting a business. The first two attempts, when I would tell people what I was working on, I would only get a mix of “that’s interesting” and “huh, best of luck”.

The latter response especially was a clear signal I hadn’t landed on something worth working on just yet. So I would put the idea to bed and keep moving forward with an open mind.

But with Stowe, something feels very different.

Just about every person I’ve spoken with has experienced the issue we’re solving for. And same thing, just about all of them say that if the product does what I say it will, they want to have it in their lives.

That feedback has been absolutely mind blowing.

And it has been so energizing!

I’m not building Stowe because I want accolades or a get-rich-quick plan. Wholeheartedly, I am building Stowe because I genuinely want to make people’s lives better and this is the best way I can conceive of doing that.

So many of you have generously shared your stories with me. These stories have motivated me and have helped shape Stowe’s roadmap.

But I am eager for more!

If you too have a story to share about your health and wellness journey, I want to hear it.

If you’ve had a bad experience because of the fragmentation and disorganization in our health systems, I want to hear it.

If you’ve got a janky workaround cobbled together to solve this problem today, I want to hear it!

Just maybe, you’ll help shape the way we make people’s lives easier as they navigate their health and wellness journeys 💛

So if you’re willing, drop your story in the chat, DM me directly, or follow our team at Stowe Health and send us a note there!

Ever yours,

Lindsay

That’s what I’ve been doing the last month or so, putting my head down and grinding. Sorry (not sorry) for the radio silence, fellow builder.

In an upcoming post, I’ll share more about our exciting Stowe progress - I’m thrilled about how much my small team has accomplished in such a short time - but for today’s newsletter I’m going to focus on the idea of what to focus on. Or to say it another way, how to avoid the insidious distractions that disrupt your progress.

Some distractions are just a matter of poor judgement. You have limited resources (time being one of them). Applying good judgement toward how to allocate your resources in pursuit of the top two to three things that yield the greatest return is arguably the most important skill when you’re building. If you’re spending time on X when Y is objectively more valuable, then X is a distraction and you’re eroding your potential outcome.

Let’s take sitting and reading a book, for example. On one hand, one could argue this is time taken away from delivering an output, which would make it a distraction. On the other hand, however, if this book is the way you learn something which unlocks significant value, it could be considered time well spent. Alternatively, if the best thing you can possibly do for your overworked brain is to rest and recover for the hard task tomorrow, then it’s also extremely valuable. You might just want to ask yourself if there is a better way to achieve that R&R so tomorrow’s brain is even better off, and maybe that other thing is worth doing instead.

Either way, when you’re serious about building, you must allocate your resources with intention. I’m learning that such relentless intention is what separates the good from the great.

Let’s talk a bit more about distractions.

Some distractions are obvious ones, but I want to spend a little more time today talking about an insidious source of erosion, both of value and of momentum.

Doubt.

I’m not talking about doubt in the form of healthy skepticism. I’m talking about doubt as the seed that worry grows from.

To worry is to fear, and fear is the mind killer.

Worry leads to uncertainty and anxiety, which leads to hesitation and poor decision-making.

Poor decision-making risks sending you off in the wrong direction altogether, whereas hesitation takes your foot off the gas. Either way, you’re missing the target.

It’s like you’re a dragster racing off the line with your chute out right from the word go. Doubt holds you back, it kills your momentum. It distracts you from the things that really matter and that’s a killer all on its own.

Art by Andrew Archer

Here’s another way to think about it.

When I was young, my parents taught me how to ride a motorbike. One of their first lessons was, “If you don’t want to hit the ditch, don’t stare at the ditch.” When you’re riding a motorbike, especially at high speeds, the bike becomes an extension of your body. Unintentionally, with your mind turning over, “Don’t hit the ditch, don’t hit the ditch”, you’re fixating on the ditch. Next thing you know, your head is turned toward the ditch, your shoulders align with where your head is looking, your core aligns with your shoulders, your hips fall in line too, and suddenly, despite your best intentions to ‘not hit the ditch’, you’re heading straight for it.

The outcome you fixate on, even if it’s a fixation on avoiding it, becomes the thing you steer yourself toward.

What if I fail? Ditch. What if no one buys my product? Right to ditch. What if I can’t raise money? Believe it or not, ditch. What if no one wants to work for me? Also ditch.

It makes me think of this video I saw in university called, The Secret. (Remember, I grew up on Vancouver Island, we were a little hippy over there, just bear with me.) The premise of the film, originally a book, was the “law of attraction” or the claim that a person’s thoughts and emotions can influence the events that happen in their life. Basically, the secret was manifestation. It was hooey for me even then, but a little part of me thought, ‘but what if it works?’

So, I secretly gave the secret a shot. I started flipping my mental framing on its head. Instead of thinking, “I hope I don’t fail that exam,” or “I hope I don’t bomb that interview,” my thinking became, “I hope I pass that exam,” or “I hope I get the job.” The jury is still out on whether manifestation truly works, but I think it says something that I’ve built a career I’m deeply proud of and a home life that makes me incredibly happy. On the other hand, I am still waiting for that lush, thick head of hair I manifested the shit out of, so it clearly doesn’t always work.

Jokes aside, without realizing it, by focusing our thoughts and emotions on these worries, maybe we’re manifesting them coming to life. In other words, we’re fixating on the ditch.

So what’s the counter?

Focus on the road ahead. Focus on the opportunity. Focus on the thing you do want more than anything. The thoughts shift from “what if no one buys my product?” to “what needs to happen so people will buy my product?” Goodbye worry, hello problem that can be solved.

Now, if you’re anything like me, you might read this and start beating yourself up for all the wasted time and energy spent doubting yourself. “Just think of how much further along I’d be if I wasn’t dragging this chute behind me!”

Well, fear not, I’m here with the counterthought once again.

When I was young, I swam competitively. During our practice sessions, as the chlorine and repeated use wore out our swim suits, instead of tossing them out, we would wear our baggy and tattered old suits over our newer suits. I say suits in this case because some of us would be layering up three, four, five old suits at a time. Sometimes we’d take it even further and wear literal drag suits, mesh things we wore around our hips and bottoms that had pouches held out by plastic semi-circles to catch even more water. Boy did it ever make our training sessions hard.

But when we finally had the chance to take it all off? The relief, the pace, the strength we felt was phenomenal. We were strong and resilient, and we felt invincible.

That feeling, reader; focus on the positive and just chase that feeling.

So, I’ll leave you with this.

Have you been staring at the ditch? Have you been manifesting the thing you don’t want instead of the thing you do? Have you been swimming wearing a drag suit, making it harder than it needs to be? If so, take it off. Believe in yourself, relentlessly. Focus on the thing you want, and chase it like nothing else matters. Like me, you might surprise yourself with what you can accomplish if you stop holding yourself back.

So much love,

Lindsay

I won’t get into the details of that story today, but ultimately it didn’t work out. From quite early on, I was building solo, and I confess that worried me at first.

There’s a playbook within the industry, one that espouses “the most successful companies have co-founders”, so I went looking for my counterpart. I kept moving forward regardless, but I was simultaneously putting in the effort to find that partner to build with.

Once bitten, twice shy, I was eyes wide open with my search and wasn’t finding anything remotely close to a fit. And so I kept building. And, I kept building. And, I kept building some more.

The progress kept coming, and I was still solo founding. At some point, I even started to joke that Claude was my co-founder.

But how could that be? Industry experts with much more experience than me say that building with a co-founder is the only real way to go, the only way to get financing from certain sources.

And yet, something felt right about this path.

Decisions were mine to own. Less time was spent clarifying and debating. I could trust my own judgement and keep moving forward at a steady clip. Co-founders can help shoulder the various burdens of building a business, but it turned out my shoulders were pretty broad all on their own. I was able to recruit highly skilled talent who wanted to join the team, but the vision could stay mine.

My experience helping others’ businesses run well has started to pay dividends.

For the first time ever, more than one in three new companies are being started solo. Five years ago, that number was under 25%. The default is quietly flipping in plain sight.

- Ari Dutilh, for Solo Founders

This experience isn’t just mine. It turns out there are growing numbers of others who are building contrary to convention.

I was recently introduced to the network, Solo Founders, which is, not ironically, solo founded by Julian Weisser. Weisser previously co-founded On Deck and ran the On Deck Founders program (ODF), a prominent and prestigious cohort-based co-founder program. He was a major advocate for the way, but he has clearly changed his tune.

The Solo Founders website, podcast, and State of Solo Founding Report all highlight founder stories and statistics to showcase the successes of the businesses they’re building.

Finding the validation that I wasn’t alone in building alone was such a boost for me this week.

There is a rough edge to this choice, however: the potential loneliness of building alone.

This time last week, I had the honour of addressing my peers in the Rotman Executive MBA program as Valedictorian.

I’m generally allergic to the stereotypical “carpe diem, the world’s your oyster” trope in a convocation speech. Especially when speaking to a room full of talented, driven, highly capable leaders who have already accomplished so much, I knew I needed to take a different tack.

Instead, I focused my address on something else that has been on my heart and mind lately, something that I realize now might have been rooted in worries about the downside of building alone.

I’m including an excerpt from that speech below, because I think it serves up a potential solution to this worry.

Photo by micheile henderson on Unsplash

Let me start by asking you this: have you ever made yourself smaller, shrunk yourself down, to make someone else more comfortable? Have you ever held yourself back because you felt you ought to “know your place”? I know I have, and I’m sure some of you have too.

Our cultural comfort zone of humility and politeness can become a double edged sword when it drives the unintended negative consequences of shrinking ambition and limiting accomplishment.

It’s even worse if one actually starts to believe that the constrained outcome is all they’re really capable of.

This phenomenon has a name, Tall Poppy Syndrome.

Why Tall Poppy?

I’ll explain.

If you can take a moment to imagine it, the poppy has a long, thin stem with a fairly hefty flower at the end. On its own, the poppy flower doesn’t make a lot of sense - it just tips right over. So, how does it flourish?

Poppies tend to grow in fields in abundance. As more and more of these flowers grow, usually around the same height, the heads of these flowers serve to bolster one another, to quite literally hold each other up.

Now imagine a particular poppy that grows taller than those around it. Sure, it’s surrounded by others, but without that flower-to-flower support, it’s almost as though it’s standing on its own.

Having grown beyond those around it, the tall poppy becomes more exposed to being battered by the wind and the rain, or it just becomes a more conspicuous and likely target for cutting down.

If you haven’t drawn the connection, that tall poppy having a hard go of it just for aiming higher might be one of us, the high achievers.

You’ve heard the expression “It’s lonely at the top”? Well, it’s worse yet if we’re talking about a tall poppy who had to go it alone along the way.

So, what’s the solution? Sure, you could shrink yourself down and avoid the exposure in the first place; or perhaps you could just toughen up, develop thicker skin, weather the storm with a thicker constitution.

Been there, done that. It’s lonely, and it’s hard.

But there is another option.

What can support a tall poppy? Other tall poppies.

There’s no need to go it alone, you just find and support each other.

…

So, I’ll end by saying this, my hope for each and every one of you:

May you grow ever taller; may you find your fellow poppies, your support, in this field of life; and may you grow on to achieve your wildest dreams.

Lindsay Kruit, Rotman EMBA Valedictory Address, June 17, 2026

The Solo Founder team signs off their emails with “Solo, together” and isn’t that a vibe us tall poppies can get behind.

Thanks for standing with me today,

Lindsay

I know that feeling well - it’s like a pilot light for the builder’s furnace. It’s an omnipresent burning flame deep inside, the fire in your soul.

Photo by Timur Kozmenko on Unsplash

My recent posts have been about encouraging the builder’s mindset and leveraging vibecoding as the means. This one’s a different tack but a similar destination. In this post I am going to write about my perspective on that deep burning feeling, especially when you lack a sense of how to really ignite it.

Here are a few lessons learned I’d like to share with you.

That feeling won’t just go away. For me, that flame, that feeling, manifested as a desire to found my own company. Sometimes, that feeling dimmed, but it never completely went away. I knew that if I made it to the end of my life and hadn’t mustered the courage to venture out on my own, I would regret it. Personally, I don’t mind failing, but I do mind the idea of having regret. In that sense, going for it is actually a safer bet than living a life of suppressed dreams.

How long have I been sitting with this feeling, you might wonder? I’ve been building publicly now for a few months now, so perhaps it’s been a bit longer than that? Maybe a year, or even two?

I almost wish that were the case, dear reader, that I woke up one morning, bit by the entrepreneurial bug, and immediately acted on it. Sadly, no. In my case, I’ve been consciously aware of the desire to be an entrepreneur for nearly a decade, and I have known in my bones that I wanted to build something of my own many years before that.

What I mean to say is that it’s been a long time. Long enough that if the feeling were to pass, you’d think it would have by now. I almost hate how long it took me to clue into the fact that I should fuel that fire rather than suppress it.

This was my first lesson learned: that feeling won’t just go away, so act on it.

It’s okay not to have an idea. I don’t have the statistics to back this up, but I would venture a guess that it’s rare that an idea simply strikes, like a bolt of lightning, fully formed out of the blue. Being an entrepreneur doesn’t start with the idea, it starts with a mindset. That builder’s fire burns, and you just need to find a problem, an opportunity, to set it upon.

One of the best ways to find a problem worth solving is to start paying attention, with intention, to the friction in your own life and the lives of the people around you. What do you find yourself complaining about? What do the people you know complain about? Are they creating their own workaround solutions to the problem?

Once you’ve spotted something, resist the urge to immediately start building what you assume the solution to be. Talk to more people first, validate your assumptions. Ask questions without leading them toward your solution. Be on the lookout for problems shared by many people who would be willing to pay for the problem to be solved. This constitutes the market, and your solution is the product. Your goal is to find a fit between the two - product market fit. Looking for more to go on? The Lean Startup coupled with Incorruptible, both by Eric Ries, provide a good framework to follow.

This was my second lesson learned: you don’t have to start with the idea, you can build up to it - you just need the right mindset.

Don’t focus on what you can’t do, focus on what you can. One of the reasons it took me so long to start out on my entrepreneurial journey was that I kept focusing on the wrong things. I worried more about the risks than the opportunities. I convinced myself of all the reasons I couldn’t rather than the reasons I could. Effectively, I kept talking myself out of it.

I had a therapist once teach me the importance of counter thoughts. If I’m ruminating on something negative - in this case all the reasons I could fail at something - naturally I am going to feel the evidence is insurmountable. Failure is all I’ve focused on. Counter thoughts involve actively working to argue the other side - all the reasons I could succeed instead. Surprisingly, there was a lot of evidence in support of my potential success. The situation just needed a reframing.

It has been important for me to remember that no single person can do everything. I used to think I needed all the answers, and needed to be able to personally do all the things, before I could consider starting my own business. What I have learned is that no one person needs to do it all.

A founder I admire recently narrowed it down for me. A CEO needs to do just three things: 1. bring in the money (meaning fundraising and/or selling); 2. inspire others to join them on the journey; and 3. set the vision for where the company is heading. Three things, not all the things. That’s manageable, right?

If that’s not you, that’s okay. Are you technically skilled at something specific? Great, you could possibly be a technical or product focused founder. Still not your jam? Are you good with people and story-telling? Perhaps sales, revenue, or growth are more your forte. I’m sure you’re catching my drift here. There’s surely something you can do.

Very few founders are Steve Jobs, Jensen Huang, and the like. Most entrepreneurs, founders, and builders are not that different from you and me. In fact, many are less experienced than you’d think. What they do have is confidence, conviction, and a healthy disregard for what could go wrong. Genuinely, if they can do it, so can you.

This was my third lesson learned: No single person needs to be all things to be a builder, so start focusing on what you can do instead of what you can’t. I’ll bet you’ll surprise yourself with what you’re capable of.

Aim higher than you think. One possibly controversial thing I’ll say as my final point is an encouragement to set the bar higher. In other words, stop playing it so safe.

I’ve spoken with many aspiring founders, and I’ve noticed a pattern. Particularly - and I say this with love - among Canadians and especially women. The idea that surfaces first is often something manageable and contained, the quintessential candle business. When I ask a few questions, it becomes clear that it’s not really their dream. It’s a way to dip a toe in without risking too much.

Don’t get me wrong, the world needs candles, but I’d encourage you to ask yourself, honestly: is that truly it? Or is it a placeholder while your real idea waits in the wings, feeling too big or too scary to say out loud?

Because here’s what I’ve found: there’s a magic that happens when you commit to something genuinely ambitious. Things start to move differently. People show up. Doors open. Things just click. The goal itself becomes a kind of fuel.

I know you, reader, you’re a badass. What bold, ambitious, massively scalable thing could you do to change the world if you really set your mind to it? I dare you to try for it.

I believe in you. You should too.

Always Yours,

Lindsay

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I’ve had the good fortune of getting my hands on an early copy of Incorruptible, the highly anticipated new book by Eric Ries, which releases tomorrow, May 26th, 2026. If the name rings a bell, Eric is the author of The Lean Startup, a book that, when I first read it, genuinely cracked something open in me.

At the time of The Lean Startup’s release, I was working at a large, well-established publicly traded manufacturing company where operational efficiency reigned supreme and the process was to be followed religiously. I had just come off an ERP implementation following the rigid waterfall methodology, and I sincerely believed that this was how serious work got done. I was a diligent and dutiful corporate employee, and it hadn’t really occurred to me there was any other way.

The Lean Startup completely upended that for me. The book made the case that in environments of genuine uncertainty (which I can now say are most of the interesting ones) the old playbook actively works against you. When you don’t yet know what you’re building or who you’re building it for, a highly detailed and rigid plan isn’t a roadmap, it’s a liability. Ries argued for speed and iteration, not to take shortcuts, but as something of the new process. The steps were simple: form a hypothesis, build the smallest possible thing that tests it, measure what actually happens, and learn - then repeat. The framework was borrowed from lean manufacturing and the scientific method, and it treated waste (e.g. wasted time, wasted capital, wasted effort building things nobody wants) as the real enemy.

For someone who had spent years equating thoroughness with value, this was a revelation. It gave me a language for something I had sensed but couldn’t articulate: that moving thoughtfully and moving quickly are not always opposites. Needless to say, not too long after reading it, I left my corporate job and joined a startup.

As many of you may already know, what happened in startup culture in the decade that followed is a more complicated story.

The Lean Startup arrived at exactly the right cultural moment, and it changed how a generation of founders thought about building. But like most powerful ideas, its influence eventually outran its original intent. The spirit of “iterate fast and learn” got flattened into something that looked more like “ship it and sort out the consequences later.” Some of this was innocent drift. Some of it, as academics like Wansley and Weinstein have written about in the context of venture predation, was something more deliberate: a funding environment that rewarded hypergrowth and fast exits over durable value creation, an environment that sometimes used the language of innovation to justify practices that weren’t in anyone’s long-term interest.

Couple that dynamic with the shareholder primacy doctrine that has dominated corporate governance for decades, and the principal-agent problems that come with it, and you start to see a pattern. The same era that produced genuinely transformative companies also produced a culture where founders were pressured to optimize for metrics that looked good on a pitch deck rather than outcomes that were good for the people they were supposed to serve. Building something great became harder to distinguish from building something that would grow fast and sell out.

Eric addresses this directly in Incorruptible, and the statistics he cites are jarring. Company lifespans on the S&P 500 have collapsed from sixty-one years in 1958 to just eighteen in 2025. Average stock holding periods have fallen from eight years to under six months. Average CEO tenure shrinks with each passing decade. As he puts it, we have entered “an age of temporary operators managing temporary organizations for temporary owners”. Nobody making a promise today expects to be around to keep it, and the public, through repeated bitter experience, has internalized that lesson. As Eric points out, trust in government in the US has fallen from 77% in 1964 to just 22% today. Confidence in big business has similarly dropped from 30% in 1999 to a record low of 16%.

This is the world I’ve been watching carefully as I slowly worked up the courage to build something myself.

Over the past decade, as I observed startup culture from the outside, a few things made me genuinely wary of becoming a founder. I watched companies raise capital on a clear mission and then watched that mission quietly get renegotiated as the investor base changed. I watched founding teams get displaced by the very structures they had built. I watched companies I respected make decisions I couldn’t square with what they had originally promised.

The story of 23andMe (which you can read more about here, here, and here) is the one I think about most, partly because what I’m building puts me in similar territory. The company didn’t set out to betray anyone. It went bankrupt, and what followed - the prospect of 15 million people’s genetic data passing to a pharmaceutical company through a bankruptcy auction, with no meaningful ability for customers to consent or object - exposed a structural failure hiding beneath a decade of good intentions. It broke something that is very hard to rebuild - trust.

I kept a close eye on all of it. Not because I was planning to write about it, but because I knew that if I ever did build something, I would need to have thought hard about how not to become that story.

As I build Stowe Health, I know in my bones that what I’m working toward could be both massively scalable and enormously impactful.

I also know that I will need outside capital to truly bring this vision to life, and that capital comes with dynamics I am not naive about. I have seen firsthand what happens when misalignment forms between founding leadership and invested ownership. It doesn’t just hurt the founders. It breaks the original basis of trust with the customer, and that is the one thing I am not willing to let happen.

My moral compass on this has always felt clear. Stowe will never break the trust of the people who rely on us. The mission is to make individual people’s lives better, and I mean that without caveat or asterisk. But good intentions, on their own, are not a governance structure. And this is precisely why I was so eager to read Eric’s new book.

Incorruptible is not a polemic against capitalism or a nostalgic wish for a simpler time. It’s a practical framework for founders who want to build companies that can genuinely resist corruption. This isn’t accomplished by hoping that the right people stay in charge, but by encoding good governance from the very beginning, structurally, before the pressure arrives.

Without giving too much away, a few things in the book really stood out:

• These problems are not reserved for inexperienced first-time founders. Despite his standing and experience, even Eric himself faced them when founding the Long-Term Stock Exchange. If he wasn’t immune to these pressures, no one is. You cannot hope them away. You have to build your company to withstand them by design.

• Wanting to build with the greater good in mind is not a naive goal. The world genuinely needs more people who believe a better future is possible and who are willing to do the unglamorous work of building it.

• And building an incorruptible company is not about the founder’s virtue holding things together through force of will. It means encoding your values into the structure of the organization itself (while you still can).

This book could not have come at a better time for me. As I continue building Stowe with a relentless focus on safeguarding the most personal data people will ever share with a company, and with an unambiguous intention to build something financially sustainable for decades rather than optimized for a fast exit, I feel genuinely grateful for the roadmap.

Incorruptible releases tomorrow, May 26th, 2026. I’d encourage you to get your hands on it.

And if you’ve been reading this newsletter thinking it was mostly about AI and vibecoding, it is in part, but really it’s about building. It’s about building despite the headwinds, be they skills gap in nature or simply the status quo. I said I’d build in public, no matter how uncomfortable that makes the introvert in me. Thanks for being here for my journey.

As always, I hope you’ll keep building with me.

Sincerely,

Lindsay

P.S. This is not an ad, I have not been paid to write this. I am just an avid reader who found the book at exactly the right moment for me, and maybe it’s the right time for you too.

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I confess I procrastinate fairly often. When it manifests for me, it often comes from a place of knowing I’ll be able to finish a task within a certain amount of time — perhaps to an overconfident degree — so I opt to deal with it later.

I’ve felt something different with this particular post, though. I am still getting into the rhythm of writing and posting, and navigating the how has been uncharted territory for me. I knew what I wanted to write about, but just couldn’t get started. I was overthinking it a bit, worried there was a “right” and “wrong” way to frame a subsequent post. I wanted to maximize the utility, benefit, and enjoyment that you — the reader — get from this newsletter. In other words, I was being a perfectionist and getting in my own way again.

But then I remembered: this newsletter is quite literally about doing it anyway. So what if I don’t go about it perfectly — I’m going about it regardless. And thus, here I am, breaking my writer’s block with a rambling preamble about writer’s block.

What really started my fingers moving on this particular post, however, was the realization that perhaps this is how many of you might be feeling about vibecoding (or trying out other new technologies available to us today). You’re perhaps curious and willing, but the sense of uncertainty about how to start is holding you back.

Are you suffering from vibecoder’s block?

Well, good news: there is no real wrong way to get started. If you’d nevertheless appreciate a guide, I’m ready with more of my lessons learned from building Effie Connect, the webapp I vibecoded in recent weeks.

In my last post, I outlined the why behind Effie. Today, I’ll cover more of the how.

Let’s recap where we left off: I knew I wanted a customized tool to help me solve a particular problem. I elected to leverage Lovable for the vibecoding, and coupled the build with Claude for planning and prompt development. Claude and I collaborated at length until we had seven clean prompts ready to drop into Lovable. The plan was to provide them to Lovable in sequence and — bing, bang, boom — I’d have my app.

While in planning mode, I didn’t shy away from talking back to Claude. These AI systems function from a place of simulated certainty, and it’s not uncommon to get a definitive response like “Great! Here’s the final answer.” I can’t stress enough how important it is to think critically about what an LLM like Claude provides you. I must have pushed back dozens of times during our iterative planning process with something like “Are you sure?” or “What about this other thing you said?” or “This doesn’t feel right.” Sometimes it would clarify and confirm, which was helpful, but sometimes it would alter course and provide something more refined.

I had been clear with Claude about my intended end use. I wanted a webapp and I knew I might share it with others, so I needed a way to manage users and data securely. Claude recommended Supabase for this — an open-source Backend-as-a-Service platform that handles the behind-the-scenes infrastructure so you don’t have to. Before doing anything in Lovable, I first needed to set up my Supabase account.

The great thing about interacting with any LLM is that it’s judgement-free. You never have to worry about looking silly in front of a boss or colleague — you can ask any follow-up questions you wish. When Claude first recommended Supabase, I had never heard of it and had no idea what steps I’d need to take to get it set up such that Lovable could leverage it. I asked Claude exactly those questions, and it walked me through the steps carefully. The necessity and value of that kind of clarification is a general theme throughout this post.

Once Supabase was set up and connected to a fresh project in Lovable, I was ready with the seven polished prompts Claude and I had prepared. They were separated this way so that Lovable didn’t attempt to accomplish too much in one go and create a mess along the way.

In theory, I could have dropped those prompts in one after another and taken a closer look only once the final product was ready. The downside of that approach is that if something is built poorly early in the process, the foundation on which the later elements rest is shaky.

Much like leading or working with others, the expression “trust, but verify” applies to managing an LLM too.

Years ago, I worked on several software implementation projects and even acquired my PMP credentials along the way. Something that stuck with me from those initiatives — beyond the importance of diligent planning — was the criticality of robust testing at various stages. I won’t take too deep a dive into the theory, but I’ll plant a few seeds.

Three key tests that can be performed when it comes to software are functional, process, and end-to-end. Functional testing confirms that a discrete function can be performed — for example, a button can be pressed as intended. Process testing verifies that a string of functions can yield the expected result — for example, a new contact card can be opened, populated, and saved. End-to-end testing verifies that a string of processes can achieve an entire workflow successfully — for example, a contact can be added, they appear as expected on the network map, and they surface within the system’s reports.

A final test worth noting is the negative test: confirming something in the negative (i.e. that you cannot do that which you should not be able to do). For example, a contact added on one user’s profile should not be visible from another user’s profile.

I applied this testing approach after each prompt I submitted to Lovable. Depending on what I had asked the system to do, I would rotate through functional, process, end-to-end, and negative testing to validate that the output was as expected. That testing lens is what turned seven polished prompts into something at least 10x that number, because I caught little things along the way and fixed them immediately, rather than letting them compound. Ultimately, I didn’t want to create the vibecoded equivalent of tech debt and end up with a shaky foundation that would be much harder to fix later.

As I built, I also realized I wanted elements I hadn’t initially considered. I was able to intersperse those additions along the way. For example, I decided I wanted a feedback form, so Claude walked me through the setup needed in an external application and gave me the prompt to add it into Lovable.

Throughout the build, I would often take a screenshot of what I was seeing, outline the result of my testing or the concern I had, and Claude would help me problem-solve. This was the primary reason I was glad to have kept the build in Lovable separate from the planning and iteration in Claude. It was almost like having a fresh perspective on the problem. I had so much back and forth with Claude that I hit the individual chat attachment limit, spinning up a new project chat thread not once but twice. Claude was my planner and thought partner; Lovable executed the plan. I can’t imagine trying to do both in the same place without it becoming a tangled mess.

Here’s a sample of how I actually talked to Claude throughout the process, in plain language, with honest feedback:

“So far things are looking really great, with a couple points of concern…”
“Here is the result from prompt #X. What tests do you recommend to validate this progress?”
“Here are the findings from the testing: 1. Test passed; 2. I am seeing a problem…”
“I can’t see the button you’re referring to. Here’s a screenshot of what I see. Help me navigate, please*.”
“This clearly didn’t work. Can we think about this another way?”
“Here’s a copy of the code thus far. Please run a security check and let me know your concerns.”
“Bearing in mind the above changes, please refresh prompts X through Y for completeness.”
“Thank you, can you prepare some sample data for me to conduct more thorough testing of…”
“I need to chew on that some more. Let’s add it to the parking lot and move on.”

(The “parking lot,” for those who are unfamiliar, is a project management term for ideas worth revisiting that aren’t blocking you right now. Highly recommend the concept for anyone prone to going down rabbit holes which, building software as a non-developer, I very much was.)

* Please and thank you are optional, but I’m sure they don’t hurt.

As you can see, I’m using natural language throughout. More than that, I’m open with my uncertainty and honest with my feedback. Working with an LLM or a vibecoding tool is almost like working with a team member. You need to set an objective, identify constraints, provide clear instructions and feedback, and trust but verify. The key difference is that it’s wicked fast and bonkers smart. What you get out of the experience comes down to how much you put in.

So, give it a go. Take your time, build carefully and diligently, but keep moving forward. I went in not knowing what I was doing, and I surprised myself with what came out the other side. I’m genuinely proud of what Effie became, and I think that’s the part that’s hardest to explain until you’ve experienced it yourself.

Don’t believe me? Here’s Effie.

— Lindsay

P.S. Effie functions much better on a webapp than on a phone.

Her work, just like mine, requires a large degree of network building to socialize the vision and the Why behind the work. When endeavouring to accomplish something scary, substantial, and really damn hard, you need allies in your corner - but you need to meet them first.

She builds up her resilience by consistently pushing the boundaries of her comfort zone through what she called “deliberate discomfort”. She described this as the act of overcoming various physical discomforts - such as being cold - in order to develop the resilience necessary to overcome something mentally or emotionally difficult - like repeatedly pitching her documentary or being in the field in less-than-comfortable settings.

I’m not sure I’ll follow her approach and start taking ice cold showers anytime soon, but the intention behind it resonated with me.

To accomplish big goals, we have to push ourselves outside of our comfort zones. We must constantly grow. We need increased resilience. And if all else fails, we need to embrace tools to supplement our innate abilities and learned skills.

I have a problem. I struggle with networking - like really struggle. It triggers my anxiety, sometimes badly enough that I’ll leave an event I truly wanted to attend just to be able to breathe again. Some people have a talent for working the room, for remembering names and context, but I am not one of those people.

I required some help. In order to build Stowe, improving my networking abilities will be paramount. I need to connect with people in new ecosystems and remember the context of our interactions, including how they interconnect with others. Initially, I was trying to solve this problem with a clunky spreadsheet coupled with attempts to leverage LinkedIn better. I don’t know about you, but for me, LinkedIn has become too unruly to bring value in the areas I need it the most.

I promised a focus on vibecoding in my early posts, and so here it is.

I knew I had a problem and I just generally wanted to give vibecoding a try. Something something about two birds and a stone, I set out to build myself a tool to better manage my growing network with intention.

As I’ve previously mentioned, vibecoding is building software or apps by interacting with an AI system using natural language. You don’t necessarily need to know how to code, you just need to know what your goal is.

Here’s how I started…

I had been briefly exposed to the vibecoding app Lovable at a conference late last year where I was granted some free credits, so naturally it was my tool of choice for this project. There are others on the market such as Replit, Cursor, Claude Code, and many more. Full disclosure: I have not yet given these others a try.

I think for the majority of users, the vibecoding app you elect to use is more a matter of preference than anything else. (I’d love to hear your thoughts in the chat below if you have a different opinion on this.) Personally, I’ve had reasonable success with Lovable, so I’ve continued to build with it and am writing about that experience today.

In Lovable, once you’re signed up, getting started is (technically) as easy as dropping a prompt into the chat bar in the middle of the screen. In this context, when I say a prompt, I mean that you can just write, in your own words, what you’re looking for. This is where the “vibe” in vibecoding comes from - you just tell the system what vibe you’re looking for, and it delivers its interpretation of that ask.

I say “technically”, however, because I don’t recommend taking this approach straight away. Putting my Project Manager hat on for a moment, I’ll highlight that projects that are well planned have an increased likelihood of success.

In Lovable, within the chat prompt bar, you may notice it says “Build ⌄”. This means any prompt you enter will result in Lovable starting to code whatever you tell it within that chat field. However, if you click the down arrow beside “Build ⌄”, you can change this to “Plan” mode, where the system allows you to discuss before you start building. Planning mode in Lovable does not consume any credits.

I recommend planning before you build for two reasons: one, unlike planning mode, building does consume credits, and having to redo poorly planned work will simply waste resources; and two, thinking through the planning process allows you to better define and articulate the end goal, making your prompts more direct and the resulting product build somewhat cleaner.

So is that how I approached it? Close, but not quite.

I am signed up for a monthly plan with Claude (I’m sure many of you are too). I’ve tried other LLMs, but it’s my preferred so far. I use it for countless tasks in support of Stowe, other professional projects, and even my personal life. I feel confident enough in my prompt writing to get the outcome I’m looking for from it.

I viewed the monthly plan with Claude as something of a fixed cost and my build credits with Lovable as a variable cost, and thus elected to engage in project planning with Claude. I suppose I could have tried switching back and forth in Lovable between Plan mode and Build mode, but I confess I was reluctant to try just in case it didn’t work as expected and burned up my credits. In my next post, I’ll explain more about why, with the benefit of hindsight, I’m glad I took this approach.

To get started with planning in Claude, I first created a Project so I can keep all chats related to this initiative in one place. Then, within the Project, I fed it the following prompt, specifying the objective, constraints, context, problem, and ultimate goal:

Side bar: If you haven’t read Power for All by Julie Battilana and Tiziana Casciaro, highly recommend.

I then provided a list of seventeen individual features I initially wanted to include in the app - but I didn’t stop there. I wanted Claude to act as my thought partner in this planning phase, and so I challenged it to stress test my thinking.

Claude and I then proceeded to engage in a substantive, iterative discussion about the plan for the network mapping app. We - meaning Claude and I - spent at least an afternoon deep in planning mode, working out both the prompt and tech stack strategy for what I ultimately decided to call Effie Connect.

At the end of this planning session, I emerged with clear instructions to stand up the tech stack and a polished set of seven sequential Lovable prompts to deliver the product.

Yes, you read that right. Not only did Claude brainstorm with me, it then clearly identified the crisp and sufficiently technical prompts to be dropped into Lovable to maximize build efficiency. All it took was a quick copy-paste, and I was off to the races.

In my next post, I’ll walk through the iterative build process to go from quick and scrappy to something more robust, including how I interspersed testing and bug fixing along the way.

Spoiler alert: it took much more than the original seven prompts.

Do you have any pain points in your daily lives, personally or professionally, that you wish there was some niche solution for? Try giving it some thought, and maybe this can be the thing you try vibecoding to solve for. I’d love to hear your ideas in the comments.

- Lindsay

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I help businesses run really well.

In recent years, that had become my motto.

I would feel a sense of pride as I said it, thinking back to my journey from small town Vancouver Island to the heart of Toronto, feeling empowered as a two-time CFO, Rotman MBA valedictorian, and proven business builder. I felt confident in my ability to bring value anywhere I worked.

Well, almost anywhere.

Anywhere, but for myself it seemed.

For years, I had felt a call toward entrepreneurship, but always managed to talk myself out of it.

Hello, Imposter Syndrome? It’s me, Lindsay.

It wasn’t the right time, I didn’t have the right idea, I didn’t have the right partner to build with, I lacked the necessary skills, I just wasn’t ready…

But that call kept getting louder and louder, and I started to challenge the risk aversion that had long held me back. I can build for others, why not for myself? I bring value for other companies, why not for my own? If they can do it, why can’t I?

I’ll save the details for another time, but I finally hit a breaking point a few months back. Enough was enough, and it was time. I was standing at a clear fork in the road, and I was going to take a hard right.

I was never going to stop calculating the risks, but I was going to start taking more of them. Since February, I have been all in on building a future on my own terms. I’ve founded a company called Stowe Health, and I’m dedicating myself toward increasing the health and prosperity of my fellow Canadians (and of all humanity, if I can play my cards right).

To get where I want to go and build what I want to build, I am going to need new skills and new support systems surrounding me. So that’s where this newsletter comes in. The introvert in me squirms as I write this, but I am going to build publically and loudly in the hopes of garnering your support along the way. I’d love your thoughts and feedback - most especially if you are building too.

But this won’t be a one-way exchange. I’m learning new things and gaining new skills along the way, and I’d love to share them with you.

In particular, most recently, I have taught myself how to vibecode. If you’re not familiar, vibecoding is building software or apps by interacting with an AI system using natural language. Quite literally, you’re chatting with the AI system, telling it what vibe you want, and it does the coding for you.

I’ll have much more to say on the concept going forward, but the long and short of it is vibe coding is democratizing access to technology in a way we’ve never seen before. It will unlock immense value for those who embrace it and is already disrupting established ecosystems across the board. If you’re reading this and haven’t tried vibecoding - I’m not going to give you too hard a time about it - but you really should be.

So, the first thing I’ll focus on with this newsletter is sharing my learnings on vibecoding. I’ve built myself a tool to help supplement an area I’m less skilled at, and I’ve surprised myself with what I was able to create. In the next few editions, I’ll tell you more about the steps I took and how you can get started too.

Seriously, if I can do it, so can you.

I’m not an experienced tech founder. I don’t consider myself an expert in anything. The learning curve ahead is unbearably steep. Nevertheless, I build.

My not-so-secret hope is that I can inspire you to build too.

- Lindsay