TL;DR: The pull of San Francisco is real and rational, and nearly everyone at this table has felt it. Humza Ahmed sat at our first dinner with a company and a little revenue, then dropped out of Waterloo, moved to the Bay, went through Y Combinator, and raised $5 million. Founders from these dinners have gone on to raise from YC, Afore, and Garage. We are not competing with any of that. What we have is twenty years of using San Francisco to build from here: when to go, what to take, what to bring home, and which parts of the Valley playbook stop working in a market where customers want social proof before they buy. You can work all of that out alone, and plenty have. It takes years, and time is the most expensive thing a founder spends. Six Tuesdays this fall, fifteen founders, and a table where a weekend project turning into a company looks like a normal thing that happens to people you know.

Applications are open until September 8: apply here.

Humza Ahmed was at a family wedding, listening to his relatives complain about work. His extended family runs real estate appraisal firms. His grandfather started one in the 1970s. The complaints were about manual data entry and reports that took a week to turn around, which is about as unglamorous as a problem gets.

He built a demo over a weekend. Then he made a fake LinkedIn profile, AI-generated beard and suit included, so that appraisers with thirty years in the business would take a twenty-one-year-old’s call. The CEO of Canada’s largest appraisal company saw his Figma mockup and asked for a demo, so he spent another weekend building something that fell apart if you pressed the wrong button.

He showed up to our first dinner series in the spring of 2024 with a company, a little revenue, and the problem of how to grow it. He sat where the fifteen founders will sit this fall.

A year later he had dropped out of Waterloo, moved to San Francisco, gone through Y Combinator, and raised $5 million for Automax.ai. He came back in January and told that story from the other end of the table, sitting next to Michael Litt, who started Vidyard in 2011 and now writes cheques at Garage.

Project first, product later, and there is no other order

Nobody in this series started a company. They started a project, and the project turned into a company later, usually after a period where it wasn’t clear which one it was.

Matt Stevens has a PhD from Waterloo and sold FleetCarma to Geotab in 2018. He now grows apples commercially near Simcoe, and he is building a robot that thins baby apples off the tree so the rest grow better. A Mennonite fabricator near him builds the frame. He iterates with a 3D printer on the back of a pickup truck in the middle of an orchard, on satellite internet. He built the product without venture money first, because he wanted to know the market was real before anyone else’s money was in it.

Mike Kirkup coached more than a thousand companies at Communitech and ran Velocity. He is back in the founder seat with Jacqui Murphy, building Elderella, and he went from concept to alpha in four months without writing a line of code by hand. They found a company that had built something similar ten years earlier. Best guess: eight to ten engineers, a couple of years. He and Jacqui now spend their spare time reading psychology books, because the hard part was never the software. It’s getting an exhausted caregiver to change how they do things.

Brad Murray was employee number four at Pebble in 2012, working on a smartwatch operating system that had no precedent to copy. Three Kickstarter campaigns, the largest at $20 million, over a million devices sold. Then Apple arrived in 2015 and it got hard fast. He co-founded Beeper with Eric Migicovsky, raised a large round in 2021 when that was easy, and went back to market in 2023 when it wasn’t. “Cash flow became king,” Brad said simply. Automattic acquired Beeper. It turned out okay. He never left Waterloo.

A wedding complaint, an orchard, a caregiving problem in his own family, a watch that just needed to exist. None of them looked like a company at the start.

The point is that it’s normal

Over twelve founders have sat at the head of this table so far, and every session is written up on this Substack. Read them in order and the effect is cumulative.

Paul Graham has a version of this argument about universities. Harvard undergrads apply to Y Combinator at roughly twice the rate of Yale and Princeton students, and he doesn’t think that’s an ability gap. It’s that at Harvard, starting a company reads as a normal thing a person like you might do. His prescription isn’t a class. It’s proximity to people two or three years ahead of you, close enough that their path still looks like a sequence of decisions instead of a legend.

That’s the mechanism, and it’s most of what a dinner does. Fifteen people hear how it actually went, including the parts that went badly, and building stops being an abstraction.

Waterloo has been doing this by accident for forty years.

The workshop focuses on the part that isn’t luck

Projects don’t become products on their own. The curriculum exists for the gap in between.

Every session came from someone at this table who has lived it. Founder-led sales. Default alive or dead, which is a real question with real arithmetic and most founders avoid doing it. Doing things that don’t scale, an essay both Michael and Humza pointed to independently on the same night. Hiring, which produced the most useful hour of the winter term after Michael described cycling through seven revenue leadership teams at Vidyard and Humza described knowing in two days that his first engineer was wrong and waiting a month anyway.

There’s no pitch practice. There’s no demo day. Humza’s line about the first version of his product taking two hundred pull requests to get right, because he built to a thirteen-page requirements list before talking to a user, is worth more than a term of pitch coaching. He now says “two hundred pull requests” to his team whenever someone starts building without a customer in the room.

Ask Mike Kirkup what actually kills the companies he has coached and he doesn’t say competition or funding. “Fighting with their co-founders, 100%.”

Using SF without leaving

The people at this table have taken every version of the trip.

Humza went all the way: dropped out, moved, raised there. He is now opening a Canadian engineering office while running the company from the Bay Area, which is roughly the right answer. Michael Litt went through YC in 2011, built Vidyard in Waterloo anyway, and now invests out of Garage. Brad Murray co-founded a YC company and never moved at all. Three different answers to the same question, and none of them is the wrong one.

What none of them did was guess. They knew what the trip was for before they took it, which is the part that takes years to learn on your own. When to go and for how long. What to bring back that actually transfers, and what only works in a market with a decade of reference customers behind it. How to keep a technical team here while your customers are there. Which introductions are worth the flight, and which ones are a coffee you could have had on a call.

Time is the most expensive thing a founder spends. Six dinners with people who already paid that cost is the fast version.

The fall speakers

Three confirmed so far:

Ryan Gariepy, co-founder of Clearpath Robotics and OTTO Motors, acquired by Rockwell Automation.

Roger Kirkness, founder of Convictional.

Michelle McBane, Managing Director at StandUp Ventures.

Three more to come.

The details

Six Tuesdays: September 22, September 29, October 20, October 27, November 17, and November 24. A late afternoon workshop and an evening dinner each session, with three weeks between to build, adjust, and test what came up.

Fifteen seats this term, and attendance at all six nights is a condition. Speakers tell the version of their story they don’t post publicly, and that only holds when it’s the same room every time. By week four the questions get better, because the person asking already knows what you’re building. If you can’t make all six dates, this isn’t the term to apply. There will be more.

Applications are open until September 8: apply here.

Somewhere in Waterloo right now there’s a person with a weekend project and no plan to start a company. Send this to them.

The Founder Dinner Series is hosted by Builders Club in Waterloo with Barn Ventures. Sessions pair evening founder dinners with late afternoon workshops. Thanks to our sponsors Osler, TD Innovation Partners, and Communitech for their continued support.

TL;DR: Every room that worked in this ecosystem was built without permission. I spent twenty years building them and asking anyway. When the boards said no for the last time, I stopped asking and built Builders Club. This is that story, and why the timing matters more than I do.

Borrowed rooms

Before I ever had a job supporting this community, I was hosting BarCamp and StartupCampWaterloo. My actual job was, at first, managing the web presence, then I was building a new co-op system at Waterloo, and it happened to come with access to the bookable rooms in the Tatham Centre. So that’s where it started: a borrowed meeting room on campus, booked for something nobody asked for. Nobody approved those events. Nobody funded them. People showed up anyway.

And the ecosystem worked the way it actually works: person by person. Gary Will, who was the only EIR at Communitech at the time, bought the pizza. Tim Ellis let us use the Accelerator Centre’s lobby on weekends. Jacqui Murphy at Tech Capital Partners, the only VC in town at the time, supported it, and so did James Smith at LaBarge Weinstein. None of that was permission. They helped because they showed up too. And as the room grew, the support grew with it.

That’s how Velocity’s path was forged. The room existed before the institution did.

The plan expires. The density doesn’t.

I was on the committee that developed an idea for mobile phones in residence to Velocity, and became its director eight months after it started. The pitch the university approved was a place for students to build mobile apps. We planned it when the BlackBerry Pearl and the Nokia E71 were the frontier, and the thesis was that mobile development was complex enough to need its own ‘living and learning’ residence. Then the iPhone changed everything. The first big things out of Velocity, Kik and Pebble, came out of a world nobody had planned for. The mandate was obsolete almost immediately. Thankfully, the residence wasn’t constrained by a committee or any oversight at all at the time.

The Creative Destruction Lab was the same pattern at a different school. I was its director from the start, and it existed outside Rotman’s organizational norms from day one. It still does. And the same thing happened that happened in that borrowed meeting room at Tatham: people showed up before there was anything official to join. Geoff Taber and Chad Bayne at Osler. The first seven who agreed to be the “board.” Brendan Calder. So many more. Support, not permission. Person by person, again. And when Sonia Sennik took over the leadership five or so years in, the momentum just kept going.

And here’s the part I love: Chad, Jacqui, and so many others from those years are in the room at Builders Club today. The people who show up keep showing up. That’s the whole thesis, walking around.

Ajay and Sonia demonstrate daily that you can run one of the most productive programs in the country without asking anyone’s permission to do it. That’s not a quirk of personality. It’s the design.

Asking for the seat

I was inside both of those from the beginning. And I still drew the wrong conclusion. I thought the lesson was: get inside the institution, get the mandate, then build. So I kept trying to get the seat. I was down to the final two for the CEO role at the two institutions that run this ecosystem’s front doors. At one of them, twice, across five years. Each time, the board chose a different path.

I’m thankful they did.

Those boards were hiring a steward for what their organizations already were. That’s their job. I was pitching what I thought the ecosystem needed next but the picture was more a feeling than an image. That is hard for a board. They need a clear direction and I couldn’t find the words at the time. I only knew the direction. But it meant the seat was never going to fit: I’d have spent these years running their formula instead of testing mine. The no didn’t close a door. It removed the last layer of asking.

Because here’s what took me twenty years to see: everything I’ve built that worked was built without permission, inside institutions generous enough to make room for it. The permission was never what made those things work. The rooms were. And whoever holds the pen writes the history, which is why, this time, I’m writing it down.

The room before the institution, again

So Builders Club has no permission layer. It’s the room before the institution, again. This time on purpose.

Even the space tells the story. It’s still a borrowed room: a floor lent by a founder who came up through this community and owns the building now. Twenty years ago, we borrowed lobbies from institutions. Now builders lend each other buildings. That’s an ecosystem growing up.

One room in Kitchener where first-timers, YC alumni, people with exits, people that work in tech jobs remotely, and big-company builders work side by side. Professionals who build inside companies all day and build their own things at night, or who are just deeply engaged in their craft. Freelancers running three different things at once. People building whatever they’ve decided needs to exist. Not all of it is tech. Some of it is services. Some of it is something else entirely. It doesn’t matter. They’re builders.

No silos, because building is building. No program clock. No formula. Come when it’s useful, work on your thing, run into people.

The results so far: dinner alumni have gone on to raise from Y Combinator, Afore, and Garage. Founders from Datacurve, Voltra, and Automax have been through early versions of the room. Communities have been born, people have moved up in their career, and small companies have been started. Not because we picked them, but because we made a space where they could step up.

The next phase

And the timing matters more than my story does. Company creation is entering a new phase. AI has collapsed the cost of building to almost nothing, and the old infrastructure was priced for the old cost. I’ve watched a mandate go obsolete before; I know what it looks like. The ecosystem that survives this won’t be run from a boardroom. Boardrooms move at the speed of consensus, and this moment doesn’t. It will be human-scale. Builder-owned. Built by people who stopped asking.

And the room keeps widening. Communitech, Osler, and TD Innovation Partners have been part of our second year. Support, not permission, the same way it’s always worked. There’s space for more as we enter our third year. This community doesn’t ask permission, but it includes every builder friend it can find. The work is making Waterloo one of the best places in the world to start and grow a company. Of any size, of any type.

I thought I needed permission from the existing orgs. I never did.

Neither do you. The room’s open.

TL;DR: David Crow closed out the S26 series with the talk he has been refining for twenty years: what venture capital actually is, from someone who has sat on every side of the table. He co-founded a company in the late nineties, sold it in a nine-figure exit, and took home about ten thousand dollars. Working out why took him through community building in Toronto, founding Influitive, and running three institutional venture funds whose portfolio included Shopify and Wattpad. The workshop covered fund mechanics from the investor’s side of the spreadsheet; the dinner covered red flags, product-market fit, and why a retired investor is the only kind who gives you a straight answer. The most unvarnished session of the series.

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Six dinners in, the S26 series ended where the startup conversation usually begins and rarely gets explained: money. Jesse has known David since the DemoCamp era, when David came back from the Valley, found Toronto tech was mostly marketing agencies, and started running the same events he had been flying to San Francisco for every week. That community fed Toronto’s startup scene and, indirectly, the creation of Velocity. He is now, in his words, semi-retired, which matters: an investor with an active fund is incented to keep hope alive. A retired one can just tell you the truth.

The nine-figure education

David’s first company started in 1997 with six founders out of Carnegie Mellon, MIT, Stanford, Berkeley, and Apple’s design group. They raised big rounds from top-tier Valley investors. In late 2000 they walked into a board meeting having closed zero deals in months, after a year of strong revenue. By Wednesday of that week they had shut three of four offices and cut most of the remaining staff.

The company still sold in 2004 for well over $100 million. David held a meaningful chunk of the cap table and took home about ten thousand dollars. Liquidation preferences ate everything below them. He wasn’t angry so much as confused: there were no blog posts about preference stacks then, one textbook mostly about chip fabs. That confusion became the career, and this talk is the current iteration of the answer.

It still happens today. The week of this dinner, TouchBistro sold to Constellation Software for $100 million after raising some $270 million in venture capital; VCs take a nine-figure loss and common shareholders got essentially nothing. The press release says exit. The waterfall says who gets paid. And the story cuts both ways: the investors lost well over a hundred million dollars on a single company, which is the risk venture underwrites on every cheque and the reason the model needs its winners to be enormous. More than twenty years after David signed his own closing docs, the mechanics have not changed, and the founders who understand them going in are the ones who come out able to try again. Structure matters as much as valuation.

The math on the other side of the table

The workshop showed why losses like that are priced in. It walked through a $100 million fund from the inside: two percent in annual fees over ten years takes $20 million off the top, leaving $80 million to deploy across ten to twenty companies. Roughly half will fail, and returns come from a small number of large winners. The two levers an investor has are speed and size: return the capital in four years and the fund needs to generate about $207 million; hold for seven and the number passes $350 million. And if a fund owns ten percent of your company, the math only works if you can become a $6 billion company.

That pressure is mostly a later-stage story. Early investors are usually the aligned ones: they hold the same upside shape as the founder, so if the founder does well, they do well. What puts that alignment at risk is a valuation that gets too high too early. A price you cannot grow into leaves founder and early backer stuck together with no off-ramp: too expensive for an acquirer, too far from the numbers the next round needs.

That arithmetic explains investor behaviour better than any pitch advice. It is why speed is the thing being priced: half a million in revenue after three years is too slow no matter how real the product is, while zero revenue and fast movement through a hard problem can be investable. It is also why David tells early founders to ignore revenue, a lagging indicator, and pick a single integer to grow eight percent week on week. When his fund invested in Wattpad, the number the founders brought was minutes of active reading, and it had been compounding for months. Nobody on the investment side knew anything about the market. It didn’t matter. An investor can argue with your choice of number, but not with the number.

What sets off alarms

At dinner the conversation turned to red flags, and David listed his without hesitation. The biggest: “if I just had money, it would solve this problem.” Investors don’t buy problems, they buy solutions; money is for growth, not repairs. Second: “this is our last round,” which tells an investor you don’t understand how they make money, since their returns depend on future rounds marking up the shares. Third: “I don’t want to sell my company,” a strange thing to say to someone whose only payday is your exit. And underneath all of them, a CEO who is not obsessed with customers.

On metrics at pre-seed, his answer to a question from the table was one word: zero. Unless you are building in a known category, seed and earlier comes down to two beliefs: that the market can get big, and that the founders are resilient enough to survive what the universe throws at them. A Waterloo degree helps and is not enough on its own. The textbook version of fundraising, hit these numbers and someone funds you, is fiction.

Product-market fit is a market question

The most useful reframe of the evening came from David’s second company. Influitive grew into a real business and then plateaued, for years, despite significant funding. The tooling worked; the market had moved. His conclusion: product-market fit has surprisingly little to do with your product. Who is the customer, are there enough of them, are they accessible, and are they willing to change their behaviour? If there are not ten thousand people willing to change how they work, the quality of your software is beside the point. The prescription is one this series keeps arriving at: spend your time with customers, don’t try to sell them, and get them to show you what they actually do.

The last seat at the table

It was the right dinner to end on. Most of what founders hear about venture comes from people with something to sell: a fund, an accelerator, a program. David has none of those anymore, and the honesty showed, on Canadian venture’s structural gaps as much as his own misses. What he left the room with is what the series has been about all along: learn the mechanics, talk to customers, and don’t run out of cash. Companies exist to create customers. Everything else is academic discussion.

Key Takeaways

Structure matters as much as valuation. A nine-figure exit can pay a founder ten thousand dollars, and it is not ancient history: TouchBistro’s $100 million sale this month left common shareholders with essentially nothing after $270 million raised. Preference stacks and down rounds decide who gets paid, not the headline number.

Know the fund math before you pitch. Half the portfolio fails and returns concentrate in a few winners, so an investor holding ten percent needs you to be worth billions. Their behaviour is not personal; it is arithmetic.

Revenue is a lagging indicator. Pick one integer and grow it eight percent week on week. Wattpad raised on minutes of active reading, not dollars. Months of compounding in a number tied to real customer behaviour beats any projection.

Money is for growth, not for fixing problems. The fastest way to lose an investor is to present capital as the solution. Solve the problem first, then raise to scale what works, and never promise that this round is the last one.

Product-market fit lives in the market, not the product. Influitive built tooling that worked and still plateaued because the market shifted underneath it. Ask who the customer is, whether there are enough of them, and whether they will change their behaviour.

The S26 Founder Dinner Series is hosted by Builders Club in Waterloo. Sessions pair evening founder dinners with midday workshops. Thanks to our sponsors Osler, TD Innovation Partners, and Communitech for their continued support.

TL;DR: Eldon spent two decades building a cybersecurity company from a standing start to a nine-figure recurring revenue business and a billion-dollar valuation, then stepped out of the driver’s seat to advise rather than lead. That distance is what let him talk plainly about what actually kept it alive, and his answer is uncomfortable: most of it was refusing to die long enough for the market to move. The evening moved across three themes that rarely share a table, AI in security, why investors pass, and founder health, and tied them together with a single idea. Survival is the job. What made this session distinct from the others in the series was how little Eldon romanticized any of it. He talked about odds, cash, and inertia the way an operator does, not the way a keynote does.

Twenty years to a Centaur

Eldon started his company in 2001 and led its machine learning and threat analysis work for two decades. No MBA. He learned to sell by selling, and closed the early customers himself years before “founder-led sales” became advice people repeat. By the time he stepped back from leading, the business had well over a thousand customers, more than $100M in ARR, and a $1.1B enterprise value. He still advises it; he no longer runs it.

He rejects the word unicorn. His preferred term is Centaur, a company at $100M in recurring revenue, and the distinction is a real one to him. Recurring revenue is durable and observable; a valuation is a story the market is telling on a given day. It was a fitting way to open a night that kept returning to the difference between what is real and what only looks real.

AI that routes work instead of replacing it

The most concrete part of the evening was Eldon walking through how AI actually entered his company, which was not as a replacement for analysts. His first model existed to match a security incident to the analyst best suited to handle it. The gains compounded fast. An early version hit 73% agreement with a Tier 1 analyst; by later in the year the system reached 93% against a far more senior Tier 3 analyst and ran roughly 29 times faster.

He was candid that the curve bends the wrong way from here. The last few points of accuracy cost more than the entire climb that got you most of the way there, and the closer you get to human-expert performance, the steeper the price. The more interesting shift was in customer appetite. Not long ago, buyers flatly refused to hand real decisions to an autonomous agent. That resistance is cracking fast, with a growing share now willing to accept some hallucination risk in exchange for real-time response. Attackers and defenders, he noted, work from the same tools and the same data. The only variable is intent.

The real vulnerability is human inertia

For all the talk of AI-chained attacks that stitch five or six vulnerabilities into a single path, Eldon located the actual weakness somewhere unglamorous: nobody patches. The hardest environments are not the most technical, they are the most stuck. Hospitals run north of a hundred vendors, firmware locked by regulators, and systems old enough that some still carry hardcoded passwords. The fix he pointed to is the model where updates are forced and the user gets no vote, the way conferencing software quietly updates itself. It works precisely because it removes human choice, which is also why it remains impossible in the places that need it most.

Why investors actually pass

The workshop earlier in the day set up the fundraising thread, and Eldon sharpened it. Founders collect a long list of surface reasons for a pass: a messy cap table, a valuation gap, a story that did not land, bad timing. He collapsed all of it into two. Either the investor cannot see a path to making their money back many times over, or they are simply not into you. When they are into you, the behavior is unmistakable. They move fast, and they do not want you talking to anyone else.

Chasing whatever is hot is a losing game, since the hot thing rotates every few weeks. The durable version is smaller and harder: find a problem enough people have, and who will pay to have it solved. On reading the room, the group worked through the tells without attaching them to anyone present. Vague language such as “send me a deck” carries almost no signal. Real conviction looks like a sale. And titles matter, because associates and business development staff cannot write checks, so the honest question is always whether you have reached a partner.

Validate with money, not words

Eldon’s customer discovery standard was the bluntest line of the night. Words are cheap and verbal validation is close to worthless. If the problem is real, someone will wire you $10K before a single line of code exists. The example that surfaced, kept general in keeping with the room’s Chatham House footing, was a founder who ran through 35 companies in their ideal profile and secured payment up front, before building anything. A design partner who has paid is locked in. One who has nodded along is not.

Founder health is company health

The evening closed on the founder, not the company, though Eldon’s point is that the two are the same thing. A sick founder cannot run a healthy business. His non-negotiables are simple and scheduled: water on waking with coffee held off for an hour, and exercise booked like a client meeting you would never cancel, an hour at a time, at least three times a week. He flagged alcohol and stimulants as genuine occupational hazards in a high-stress seat, and pointed the room toward the founder health framework that came out of a Huberman and a16z conversation, built on exercise, sleep, decompression, and focus.

The throughline held all the way to the end. Fifteen percent of startups make it ten years, worse odds than most founders let themselves believe. Eldon’s reframe is meant to free you rather than scare you. Your company is probably going to fail anyway, so you may as well keep going. Treat yourself as the Chief Survival Officer, stay solvent and sane, and give the market enough time to shift in your favor.

Key Takeaways

Survival is the strategy, not a byproduct of it. Only about 15% of startups reach ten years. Eldon’s response is to stop treating failure as a threat and start treating it as the baseline. Once you assume it, the fear stops driving decisions and you can focus on staying alive long enough for conditions to change.

Validation is measured in dollars, not enthusiasm. Verbal interest tells you almost nothing. A design partner who pays $10K before you have written code has told you the problem is real and locked themselves in. Thirty-plus conversations with your ideal customer, followed by an upfront ask, beats any amount of encouraging feedback.

Investors pass for two reasons, and the rest is noise. Either they cannot see the path to a large return, or they are not into you. When they are, they move fast and want exclusivity. Vague language is not a maybe, it is a no, and only a partner can actually write the check.

Use AI where it fits and regex where it fits. Eldon’s model succeeded because it routed work to the right person rather than trying to replace people. The last two points of accuracy cost more than the first twenty. Adopt the tool that matches the problem, not the tool that matches the moment.

The hardest security problem is behavioral. Chained AI attacks are real, but the vulnerability that matters is that people and institutions do not patch. Forced, choice-free updates are the right answer and remain impossible in the environments that need them most.

Founder health is not self-care, it is operations. A founder who is not sleeping, moving, and decompressing is a single point of failure for the whole company. Scheduling exercise like an unmissable meeting is a business decision as much as a personal one.

The S26 Founder Dinner Series is hosted by Builders Club in Waterloo. Sessions pair evening founder dinners with midday workshops. Thanks to our sponsors Osler, TD Innovation Partners, and Communitech for their continued support.

A companion to Built to Support, Not to Capture.

TL;DR — Building a company is one of the riskiest financial bets a person can make, and none of the systems meant to back risk-takers — tax, grants, lending — recognize it. They wait for the outcome, then line up for a piece. The fix isn’t another program: recognize the risk people take to build anything, and support it early. Do that and you get more venture-scale companies too, because they come out of the wide base of people building any kind of company — not out of programs aimed at the ones who already look safe.

Picture the person we say we want more of. She’s got a job, a salary, a mortgage. She has an idea for a company — maybe a big one, maybe a good small one, she can’t know yet. To find out, she has to quit the salary, sign a personal guarantee for anything the business borrows, and put her own name behind every dollar of downside. If it fails, that’s hers. All of it.

That leap is the single most important thing that happens in an economy, and it’s the moment our entire support system is built to ignore. We have a hundred programs for the founder who already made the jump and landed — nothing for the one standing at the edge. We don’t back the risk. We wait to see who survives it, then ask for a cut.

Recognize the risk on the way up, not the reward on the way down. That’s the whole change. The rest of this is why it matters and what it looks like.

Built to reward the outcome, not the risk

The tax system treats you as a source of revenue from day one, not someone absorbing years of downside on a bet that might pay off. The grant system waits until you’re incorporated, have traction, and already look like a winner — it de-risks the people who’ve mostly de-risked themselves. The funding system shows up later still, and only for the narrow slice that can plausibly return a fund.

Everything rewards the outcome. Nothing recognizes the risk that produces it.

And the risk is personal — all of it

There is no such thing as a business loan in this country that isn’t personal. A BDC small business loan requires a personal guarantee. Your bank requires a personal guarantee. Take on debt to build something and you are personally on the hook — your house, your credit score, your name. A business credit card that doesn’t touch your personal credit only became possible here in the last few years, and only through fintechs that route around the banks entirely.

For most of this country’s history, the message to anyone building a company has been: the risk is yours. All of it. Personally.

Then it works — and everyone wants in

Watch how fast the posture changes. The grant programs that wouldn’t touch you pre-revenue put your logo on their wall. The investors who passed want the round. The system that priced your risk at zero on the way up wants a piece of the upside on the way down.

The support is treated as a public good; the success is treated as private property to be claimed. The last piece found this misalignment in the programs — public money de-risks the founder, private money takes the equity — but it runs deeper than programs. We socialize the encouragement and privatize the credit.

The part funders should sit with

Backing people who build any kind of company produces more venture-scale companies than any amount of venture-focused intervention. It starts with building a company. Full stop. The agency, the shop, the small software product, the services business that hires three people — that’s the top of the funnel. Some of those founders discover they’re standing on something that can go much faster, and that’s what VC is for: fuel for the rare company that can. You don’t get the rare company without the wide base it comes out of.

Optimize only for the ones that already look venture-scale and you’re not de-risking anything — you’re harvesting a funnel someone else built. Usually in the US, and they keep the upside. We pour programs into the stage where the risk is already legible and leave the actual risk — the decision to build anything at all — unsupported. Then we wonder why 517 US companies have Canadian founders, 88% of them our own graduates.

What recognizing the risk looks like

Fix who gets in the door. Tax treatment, grant eligibility, lending — stop gating everything on having already survived. A founder who quit a job to build is taking risk, not failing to qualify. The cheapest thing to change is the threshold.

De-risk the person, not just the cap table. The most punishing fact of building here is that every dollar of business risk lands on you personally. Anything that moves risk off the founder’s own name — real credit without a personal guarantee, backing that arrives before the company is “safe” — does more for company formation than another accelerator.

Support building a company, period — not building a fundable startup. Encouragement, permission, a room full of people doing the same hard thing. It’s cheap, it needs no scalability test, and it’s the widest mouth of the funnel that produces the venture-scale outcomes everyone actually wants.

Then align: keep a piece by backing them, not by claiming them. The green shoots from the last piece — House 831, Launch Academy, Vancouver.dev, ElanTech, Rep Matters — are founder-owned rooms handing out belonging before anyone is fundable. Back the risk early. Own a piece because you were there for it, not because you showed up after it worked.

Why we build it this way

That’s the whole idea behind Builders Club: one entity — the room, the people, the capital — that only wins when the founder does, and shows up for the risk before anyone else will price it. Not because venture-scale companies don’t matter. They’re the point. You get more of them by backing everyone with the nerve to build a company than by only backing the ones who already made it look safe.

Canada asks its builders to carry all the risk personally, recognizes none of it, and lines up for the upside the day it appears. The better system prices the risk on the way up — and keeps a piece of what it backed, so the value stays here too.

Build with us · See the full map · Read The Conveyor

TLDR; Devon Galloway co-founded Vidyard out of Waterloo, took it through Y Combinator in 2011, and has spent the fifteen years since both building it and, from 2013 on, investing through Garage Capital. He joined us to talk about the part most rooms skip: what happens after the validation pyramid, and what venture money is and isn’t for. The throughline was discipline about reality. The best pitches are dead simple, most software no longer has a durable moat, half of any good fund’s bets fail, and the thing that reliably wins is a founder who will figure it out. It paired cleanly with the workshop on default dead or alive, because Devon’s spent a long time deciding which companies are worth betting on, and for how long.

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The first three dinners were founders talking about building. The fourth brought the conversation to the other side of the table. Devon Galloway has built, he is still building as CTO of Vidyard, but he has also written close to 300 early-stage cheques through Garage Capital, and that double vantage point shaped the whole evening. He started angel investing in 2013, fresh out of YC, back when he and his co-founder were paying themselves two thousand dollars a month and felt rich.

Fifteen years past the finish line

Devon’s least favourite founder trope is the one that treats getting into YC as the finish line. He called it the validation pyramid: the talks, the startup-school advice, the scramble to put a logo on a slide. For him and his co-founder, YC was the beginning of the beginning. The fifteen years after the batch taught him far more than the batch itself did, and would have changed plenty of his early decisions if he had known what was coming. The road is long, he wanted the room to understand, and the validation you chase early is rarely the validation that ends up mattering.

What those years did teach him is how to recognize a good pitch, and his test is almost aggressively simple. He and his co-founder day-traded together as co-op students, badly, and the tips that stuck were always the clean ones: a friend leaning over to say, here is the one thing about this company. He still remembers a tip about a small pharma company whose FDA clearance had been pulled and looked likely to come back. One sentence of insight, and the stock ran.

A startup pitch should sound the same. There is usually one real insight, and everything else is detail. The Groq pitch was that clean: AI is going to be enormous, the chips built for it are bad, I will build a great one, and I happen to be very good at chips. He gets three- and four-page founder emails all the time, and the length usually tells him the founder doesn’t yet know what is special about the business and is hoping the reader will find it for them.

Default dead, on purpose

Groq is also the cleanest illustration of the workshop’s theme. It was default dead for the better part of a decade: little real revenue, selling mostly to universities and research labs, burning capital to build genuinely hard technology. Nvidia bought it last Christmas for twenty billion dollars, the best outcome in the fund’s history. That is the exception that proves the rule rather than a counterargument to it. Most deep tech is default dead for years, and that is acceptable only when the prize at the end is enormous. Default alive, the frame from the earlier workshop, is simple arithmetic: on flat expenses, with the cash you already have, does a dollar in come back as at least a dollar? Knowing that number is what gives you a direction to climb toward, and most founders avoid running it because the answer is uncomfortable.

For companies that are not building a chip, the question of when to raise has a cleaner answer. Devon’s tell for product-market fit in software is the ratio of customer lifetime value to acquisition cost: put plainly, your company is a machine that turns one dollar into five, and if that is true and it scales, putting more dollars in is close to a no-brainer. The harder truth is that technology moats have thinned. Someone can prototype your software over a weekend and your margin goes to zero. The advantages that compound now are customer ones: knowing a problem better than anyone else, becoming the system of record, and getting genuinely creative about reaching customers when every inbox is buried in noise.

He quoted Buffett, that you find out who is swimming naked when the tide goes out, and the tide is out on software right now. Then Larry Smith: if you can crack go-to-market while it is hard, you should be dancing in the streets, because almost everyone else is stuck.

The other side of the table

The most useful stretch of the night was Devon being honest about fund math. A great fund returns about five times the capital its investors put in; ten times is crushing it, and under three is mediocre. The way you get there is brutal in its concentration: roughly five percent of the money has to come back a hundredfold, and almost nothing else moves the needle. Half of a VC’s investments fail, and a two or three times return, life-changing for the founder, is a rounding error to the fund. Paul Graham calls this black swan farming, and it means an investor’s real fear is not backing a company that dies; it is passing on the one that becomes a home run.

The honest consequence is that an investor never validates your company. They validate that you fit their thesis right now. That runs both ways: if an investor has gone quiet because your outcome no longer moves their fund, name it, be respectful of their time, and call them only at the moments they can genuinely help. Sunlight is a good disinfectant.

The economics underneath all of this have moved, and not subtly. When Garage started in 2015, the largest outcome anyone could point to was Instagram at a billion dollars, and that felt absurd. WhatsApp later went for nineteen billion and held the record for years. Groq took it last Christmas at twenty, then lost it to Google’s Wiz deal a few weeks later. SpaceX now sat near 1.7 trillion while still private. The point was not the trivia; it was that the prize in private markets is now a hundred to a thousand times larger than it was a decade ago, and companies can stay private long enough to capture it rather than handing it to public markets early. That shifts the math on almost every decision, including where you raise. Moving an entry valuation from ten million to twenty is immaterial when the outcome at the end is ten or a hundred times bigger.

Building today

So what does this mean for someone starting now? The leverage has changed. Devon described a founder doing the work of a full sales team essentially alone, using AI agents to run prospecting and outreach across a hundred fronts at once. That is the gift of the moment: a resourceful person can cover ground that used to take a headcount of dozens, and the prize at the end is larger than it has ever been. The hard part, the unglamorous go-to-market grind, is also the opening, because most people are waiting for it to get easier instead of doing it.

The catch is that the same tools are in everyone’s hands, which is why the durable edge keeps circling back to the founder. Build something a few people genuinely love, stay closer to the customer than to the investor, and be the kind of person who figures it out when the plan breaks. That is the part no model and no market shift replaces, and it is what Devon returned to all night.

Key Takeaways

The best pitch sounds like a stock tip among friends. One or two sentences on why this wins, and the rest is detail. If a founder cannot find that line, an investor usually cannot find it for them, and a long email is a tell that the work hasn’t been done yet.

Default dead can be a deliberate strategy. Companies building hard technology stay default dead for years by design, and that is fine when the eventual prize is enormous. It is not a licence for everyone else; most companies do not have that excuse, and should be doing the default-alive math instead.

Most software no longer has a technology moat. A weekend is enough to clone a lot of products, which pushes margins toward zero. The advantages that compound are customer-side: deep knowledge of the problem, being the system of record, and finding novel ways to reach people when attention is scarce.

You are a lottery ticket, and understanding that helps. Half of any good fund’s bets fail and a 2-3x outcome barely registers, even though it would change a founder’s life. Knowing you are one ticket among hundreds lets you manage the relationship like an adult rather than chasing approval.

Know your default-alive number before you decide anything about money. It is plain arithmetic on flat costs and current cash, and it is the thing that tells you whether to raise, how much, and when. Without it, every funding decision is a guess dressed up as a plan.

Don’t let geography set your ceiling. The prize in private markets is far larger than it was a decade ago, and capital now stays private long enough to capture it. The ambition you choose is the ambition you get priced on.

The S26 Founder Dinner Series is hosted by Builders Club in Waterloo. Sessions pair evening founder dinners with midday workshops. Thanks to our sponsors Osler, TD Innovation Partners, and Communitech for their continued support.

TL;DR: Sheldon McCormick took eight years to build the confidence to start a company. He spent four of them inside Uber’s Canadian launch, recruiting drivers from the back of the taxi line at Billy Bishop and scaling that motion from 30 drivers a week to 800. Then he co-founded Properly, a proptech company that found real pull during the pandemic, lost it when the market turned, and found a responsible ending. It was the most candid session of the series so far: a founder walking through what worked, what didn’t, and what he’d tell you to avoid. The throughline was his own lesson: there is always a move to be made.

The third dinner of the series picked up exactly where the afternoon workshop left off. The workshop covered Paul Graham’s Do Things That Don’t Scale: the manual, unglamorous work that early companies are built on. Then Sheldon sat down and told a story that is, start to finish, a case study in that essay.

Eight years to confidence

Sheldon didn’t start a company out of school. His university roommate did, coding twelve hours a day in their shared apartment, and Sheldon concluded a startup wasn’t for him. He went into consulting instead, and a few years later found himself a regional expert in light commercial air conditioning market share in Brazil, wondering what his life had become. Around the same time, his roommate sold his company. Sheldon liked that trajectory better.

The roommate also introduced him to a new thing called Uber. Sheldon joined the Canadian team when it was three or four people. On his first day, the job was simple: go to the airport, stand at the back of the taxi line, and recruit drivers. Eight to ten hours a day. The back of the line, not the front, because the line keeps moving and you want to keep talking.

The work that doesn’t scale, at scale

That manual motion became a system. When Uber assigned him to launch uberX in Toronto in 2014, the goal was 30 drivers a week. Six months later it was 800 a week. Getting there meant renting hotel conference rooms in Brampton, Mississauga, and Richmond Hill two or three days a week, filling them with a couple hundred prospective drivers, and giving the same talk over and over. With language barriers and a legal fight with City Hall running in the background, people needed to see a human being who could look them in the eye and answer the question: is this okay?

By the time he left, the Canadian business he helped run had grown enormously, and the company had gone from a few hundred employees to tens of thousands. The lesson he took wasn’t that Uber was magic. It was that the founding team weren’t kings or gods. They were smart and curious, and not that different from people he knew. So he started.

Properly and the two-miracle business

Properly launched as an iBuyer: sell your house to us directly, skip the listing process, get certainty. Sheldon did the first 3,000 homeowner calls himself. Top of funnel was easy, because “we’ll buy your house” is a compelling offer. Conversion was brutal, because homeowners are emotional about price. Every one of them was anchored to the neighbour who sold two years ago at some outrageous number.

He calls this a two-miracle business: you need homeowners to sell to you at a fair discount, and you need to resell profitably, and you need both to work at massive scale. One miracle is hard enough. He’d also add a warning about seasonal and cyclical markets, not for the reason you’d think: at small scale, seasonality destroys your ability to read your own experiments. Is the test failing, or is it just December? You can lose a year trying to tell signal from noise.

Finding pull

The pandemic broke the iBuying model overnight, and forced the pivot that defined the company. Instead of buying every house, Properly offered Sale Assurance: a firm backstop offer that let homeowners buy their next house with confidence, knowing they could sell to Properly if the market didn’t come through. Same core competencies, far less capital required, and a piece of paper a bank could underwrite a mortgage against. Major Canadian banks got on board, and once one did, the rest followed.

The difference was immediate and physical. With iBuying, ten homeowner conversations got nine hang-ups. With Sale Assurance, the same ten calls got three hard yeses. Revenue went from zero to meaningful in six months. For the first time since Uber, Sheldon felt pulled by the market instead of pushing a boulder up a hill. That feeling, he told the room, is the real test of product-market fit. Your job at a company with pull is keeping the thing on the rails. Your job without it is endless experimentation.

Losing it, and the move that was left

When rates rose rapidly in 2022, liquidity vanished from Canadian housing and the product stopped converting. The reason traced back to the very first lesson from those 3,000 calls: homeowners are emotional about price. The backstop offers the market could support no longer let people unlock the equity they needed for their next home, and intellectually fair terms couldn’t overcome that. Product-market fit turned out to be a moving target, and the market had moved.

What happened next is the part of the story founders rarely hear. When it was clear the venture-scale outcome was gone, the team didn’t freeze and didn’t burn what was left chasing a long shot. They got creative, did the work, and found a responsible ending. Not the outcome anyone wanted. But there was still a move to be made. There always is.

What he’d tell you

A few of his lessons landed hard with the room. Never put an intermediary between you and your customer; he regrets every dollar of product sold through a channel instead of directly. Watch your team’s sales calls maniacally and build structured feedback, even when it’s painful to listen. And understand that when things go wrong, your investors’ portfolio math takes over. They are not villains, but they are not your friends either. Make decisions for yourself.

He closed with a line from a former colleague that he kept on his wall: it never gets easier, you just go faster. After Uber, after Properly, he’s now leading Communitech, which means the region’s founders get the benefit of every one of those scars. Only start a company, he said, if the problem genuinely captivates you. Nothing else survives contact with year seven.

Key Takeaways

Beware the two-miracle business. If your model requires two independent hard things to be true before it works, you’ve doubled your risk before you’ve started. Count the miracles in your plan honestly.

Pull is the test. When you have product-market fit, your job is keeping the machine on the rails. When you don’t, every day is another experiment. If you can’t tell which mode you’re in, you’re in the second one.

Product-market fit is a moving target. A model can be honest, transparent, and backtested, and still stop converting when market conditions shift what your customer can emotionally accept. Fit isn’t something you find once; it’s something you have to keep re-earning as the world changes around you.

Seasonality wrecks your signal. At small scale, cyclical markets make it nearly impossible to tell whether an experiment failed or the calendar did. Account for it before you trust your data.

Never put an intermediary between you and your customer. Channels feel like leverage. What they actually do is cut you off from the feedback that keeps your product honest.

There is always a move. Even when the venture outcome is gone, a founder with cash, a board, and a clear head has options. Finding the responsible ending is part of the job too.

The S26 Founder Dinner Series is hosted by Builders Club in Waterloo. Sessions pair evening founder dinners with midday workshops. Thanks to our sponsors Osler, TD Innovation Partners, and Communitech for their continued support.

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A follow-up to “The Conveyor.” If you read that one, you know the machine. This one is about what we do with it — and why our answer so far has been the wrong one.

A year ago I wrote that Canada produces incredible founders and loses the best of them before a local VC ever sees them. Then I spent a year in the data showing exactly how — the conveyor belt of US programs that recruits Canadian builders from high school onward, the 88% of those founders who came through our own lecture halls, the value that pools in San Francisco while we keep the alumni photo.

People mostly agreed with the diagnosis. Then they asked the obvious question: so how do we keep them home?

The instinct behind that question is right. We want Canadians to win, and we want that winning to mean something here. But “keep them home” quietly treats a Canadian success as a Canadian loss and that’s the part we’ve got backwards.

Here’s a very Canadian way to see it, including the trap we fall into. We’ve spent more than thirty years mourning that no Canadian team has won the Stanley Cup since 1993, reliving the drought every single June. And yet Canadians win the Cup every year — on American teams. We produce most of the league’s best players and we own the entire system that makes them: the rinks, the junior leagues, the scouts, the development pipeline that runs through every small town in the country. We celebrate each of those players by name. We just refuse to count it as a win, because the trophy didn’t come home.

That reflex — claiming the individual while mourning the collective — is exactly the one we’ve adopted in tech. And it has to stop. A Canadian hoisting the Cup in an American city is still, unmistakably, a Canadian win; we’ve just trained ourselves to feel it as a loss. Now we do the same thing with founders: we lament that the company isn’t headquartered here while a Canadian builds it into a giant somewhere else, and we miss that the win was ours the whole time.

This was never a fight with San Francisco to win or lose. It’s an opportunity to participate in — and the founders are showing us not just what they want, but how well it works. The move isn’t to keep them home. It’s to get in the game: to hold a stake in the outcome wherever it gets built. And we can’t do that while the foundation of our ecosystem is a hundred non-profits built to help instead of own.

What we built instead of capital

Here’s something we measured for this project. There are roughly 110 founder-support programs in Canada that we could catalogue — accelerators, incubators, grants, regional development funds, competitions. That’s not the full count; it’s the ones with a website and a name. The real number of touchpoints is higher.

Look at how they’re built and a single pattern dominates. The typical Canadian program is non-profit or government, and it’s funded by braiding the same four layers together: a federal regional-development contribution as the anchor, a provincial match on top, a university partner contributing space and talent, and corporate sponsors rounding it out. Most take no equity. By design. They are built to assist a founder, not to own a piece of one.

That’s the whole story in one structural fact. The American conveyor looks at a nineteen-year-old in Markham and sees an investment, it writes a cheque and takes a stake. The Canadian system looks at the same kid and sees a cause — it offers a program, a mentor, a grant, and waves them off at the gate. One side ends up on the cap table. The other ends up issuing a press release when the kid’s company IPOs in New York.

We didn’t build a capital ecosystem. We built a charitable one and then we acted surprised that the returns went somewhere else.

One important thing to be clear about: this isn’t about Canadian VCs. Over the same stretch, a cohort of Canadian firms grew up doing exactly the right thing — backing Canadian founders wherever they choose to build, with real cheques and real ownership, and several have closed strong new funds recently. Version One, Garage Capital, Golden Ventures and others have shown the ownership model works and travels. They’re not the problem; they’re the proof of concept, and they’re an asset to build on. The critique here is aimed squarely at the assistance layer — the hundred non-profit and government programs we’ve stacked up around the capital, mistaking help for ownership. The capital side is where Canada has been getting it right, and we need more of it, earlier.

It didn’t work — and we can show it

The kind defense of all this is that it’s at least helping at the margins. Maybe fewer founders leave than would have. I went looking for evidence of that and couldn’t find it. None of these programs publish retention or outcome data you could tie to founders actually staying. So I can’t tell you the model failed. I can tell you there’s no evidence it succeeded — and the one trend we can measure cleanly didn’t move.

Here it is. The share of Canadian-founded billion-dollar companies that got built at home fell from about 60% before 2001 to about 32% in the 2016–2020 cohort. The crossover — the moment more of our winners started building in the US than here — happened around 2006.

Now line that up against the timeline of everything we just talked about. The non-profit support ecosystem expanded hardest after 2015. New programs, more funders, bigger announcements, year after year. And the home share kept sliding straight through the period we were building all of it.

So the most generous reading of two decades of assistance is zero net effect. The less generous reading is worse: a well-funded support layer that gets founders “investor-ready” — polished, networked, pitch-trained — without giving them capital or ownership is functionally a finishing school for the conveyor. We sand the talent down to a fine point and then the people with cheques in San Francisco pick it up. At our own expense, we may be advertising the US path as the one with real money behind it.

I want to be careful here, because the distress in the system is real and the people running these programs are good people working hard. This isn’t an attack on them. It’s an argument that we pointed all that effort at the wrong outcome.

Keeping them home was never the move

Set aside whether the programs are well run. Ask whether the goal — retention, keeping founders home — is even the right one. I don’t think it is, and the reason is in the data too.

Speed to a billion dollars is now roughly equal whether a Canadian builds at home or in the US. That surprised me. The American edge was never really about being faster or even about writing bigger cheques. It’s about density — capital, customers, mentors, and other all-in founders compounding in the same room, raising the odds and the speed of every next move. Density is the one asset no single subsidy can buy, and it’s the one San Francisco already has in surplus.

For high-agency, high-performing people, proximity to that kind of opportunity isn’t constrained by a border. This is the part I’ve come around to: it’s not that our best founders wouldn’t build here. It’s that they can’t — not at the same altitude — because the frontier is somewhere else and the whole point of being that caliber of person is that you go to the frontier. The best junior players have always gone where the best hockey is played. That isn’t a defeat to reverse; it’s just how talent behaves. Building a slower San Francisco next door and asking people to stay out of loyalty was never going to work, because pride doesn’t compound — capital does. The opportunity isn’t to wall the talent in. It’s to back it wherever the frontier takes it, and hold a stake when it wins.

What joining them actually means

So stop trying to keep them home. Start owning a piece of where they go. The shift is from assistance to equity, and it runs in three moves.

Back the talent wherever it builds — and take a stake. If Canada made the founder, Canada should own a piece of the outcome, not just claim the bragging rights. That means Canadian capital that’s willing to travel with a Canadian founder to San Francisco and write the cheque, instead of charity that stops at customs. A win for a Canadian who built in the US is still a Canadian win — but only if we’re on the cap table when it happens. Right now we’re not, because we filed the whole thing under help.

Get in before it makes sense. The conveyor’s real weapon is timing: it shows up at the idea stage, pre-incorporation, while the founder is still in the room. Canadian institutions, by founders’ own accounts, won’t move until the success is already obvious — and by then the founder is gone and so is the cap table. Owning the upside means being early enough to actually own it. Late capital doesn’t get a stake; it gets a markup.

Count the people we currently can’t see. Our data captures Canadians who founded US companies. It cannot see the Canadians who are early scientists, key engineers, and first operators inside US companies founded by non-Canadians — and that group is enormous. The frontier AI labs are full of Toronto- and Waterloo-trained people who will never appear on any founder list. That contribution is real, it’s ours, and it’s completely unmeasured. A serious strategy treats those people as a network to invest through — the warmest possible path to the next company — not a loss to mourn.

None of this means giving up on building here. It means being honest that the thing we kept calling charity was always an investment, and the Americans have been collecting the returns for a decade while we collected gratitude.

What we’re actually doing about it

This is why Builders Club and Barn Ventures exist, and why they’re built the way they are.

Builders Club is the density — a community in Waterloo of builders going all-in around each other, because the room is the thing no program can manufacture and the one input the conveyor can’t ship in from California. Barn Ventures is the capital that shows up before it makes sense: first cheque, pre-incorporation, equity early, while the founder is still here and not yet on a flight south. The same three things the conveyor sells — capital, density, access — offered first, at home, as an investment. A stake in the talent we already produce on a schedule, instead of a free handoff.

We’re not trying to replace San Francisco. You can’t out-San-Francisco San Francisco, and some of the best people will still go — that’s fine, that’s physics, and we’d rather own a piece of them when they do than wave a flag from a thousand miles away. We’re trying to do the one thing the assistance model never did: treat Canadian builders like they’re worth owning, because they are.

The talent was never the problem. Waterloo makes it every year, on time, world-class. The problem was that we built a hundred ways to help and almost no ways to own — and we kept calling a Canadian win a Canadian loss, the same mistake we make every June staring at a Stanley Cup that isn’t in a Canadian city. The way out isn’t to keep anyone home. It’s to get in the game the way we always have: own the system that produces the talent, and own a piece of the talent wherever it goes on to win — capital, not charity; ownership, not assistance; at home where we can, and right beside them everywhere else.

Building something early, or just want to talk it through? We’re easy to reach → barnvc.com

Sources

• The catalogue of ~110 Canadian founder-support programs, and the home-share figures for Canadian billion-dollar companies, are from Barn Ventures’ own research, compiled June 2026 from public reporting and the sources below.

• The Dominion List — running catalogue of U.S. companies with a Canadian founder: dominionlist.com

• “The Conveyor: How US Capital Recruits Canadian Founders” — companion essay (the 88% education link and the speed/density argument): https://barnvc.com/the-conveyor.html

• “The Great Canadian Founder Drain: What Are We Missing?” — Jesse Rodgers, Feb 2025: https://whoyoucallingajesse.com/the-great-canadian-founder-drain-what-are-we-missing-1caf77dd54be

TL;DR:
Built for Her wasn’t just a conversation about women’s health tech. It was a conversation about what happens when entire industries are built around the wrong default, and what it looks like when founders start rebuilding them from the ground up.

When “Sounds Like Anxiety” Becomes a Pattern

We live in the most technologically advanced healthcare era in history. AI can detect patterns invisible to the human eye, and medicine has never been more data-driven or personalized.

And yet millions of women still leave medical appointments wondering if they imagined their own pain.

That contradiction sat underneath Built for Her, a Toronto Tech Week event hosted by HerSay around women’s health, AI, the future of care and Sarah Beth Bianchi. Across conversations on healthcare, design, venture capital, and technology, speakers kept returning to the same idea: many of the systems shaping modern medicine were never really built around women in the first place.

Rebecca Lyons, founder of HerSay, opened the evening with the story that pushed her toward building the company. Before entering women’s health, she studied psychology at the University of Waterloo, drifted into business psychology and innovation, and eventually found herself working in trucking. None of it looked linear in retrospect, but that was part of the point.

“Reinvention isn’t failure,” she said. “It’s feedback.”

Each chapter, even the ones that felt disconnected at the time, prepared her for something she would later apply somewhere more personal.

A few years ago, Rebecca started experiencing severe pain that made ordinary things difficult. Breathing hurts. Getting out of bed hurts. She booked a doctor’s appointment, explained what she was feeling, and was met with a response many women in the room immediately recognized.

“Sounds like anxiety.”

The pain didn’t disappear, but her confidence did. That was the part she kept returning to throughout the night. Medical dismissal doesn’t just leave symptoms untreated. It teaches people to distrust their own instincts. Eventually the question stops being “what’s wrong?” and becomes “am I overreacting?”

She changed providers. She then was diagnosed with a stage four lifelong disease.

What shocked her afterward was not just the diagnosis itself, but how common the story turned out to be. Once she started speaking openly about the experience, women around her had nearly identical versions of it: different symptoms, different conditions, but the same pattern of uncertainty, dismissal, and years spent trying to explain pain that never fully made sense to anyone else.

That realization became part of why she started building HerSay. In a world with more medical information than ever before, why do so many people still leave appointments feeling unheard or unable to advocate for themselves? Rebecca emphasized that the issue isn’t just access to information, but confidence. AI can process data and recognize patterns, but it cannot understand the emotional weight of not being believed.

As she put it throughout the discussion, transformation in healthcare is not just digital, it’s relational. The goal is not to replace doctors, but to help patients become more informed and active participants in their own care.

One statistic shared during the event captured the scale of that frustration. Among the women HerSay surveyed, 89% said they had felt dismissed by healthcare providers, with average frustration ratings consistently high across responses.

By the end of the night, Rebecca kept returning to a simpler idea underneath all the technology and data: trust your gut. If something doesn’t sit right, that instinct can be powerful.

The Data Gap Underneath Everything

The problem, as several founders pointed out throughout the panel, is bigger than individual doctors. The issue is structural. Before 1993, women were largely excluded from clinical trials, and much of modern healthcare data was built around male bodies as the default model. Many of those assumptions still quietly shape products, diagnostics, research priorities, and treatment systems today.

Parnian Majd, a medical engineering founder building wearable reproductive-health technology, described discovering just how deep the gap runs while researching women’s biomarkers. At one point, she found decades-old research papers measuring pH levels in cows while equivalent baseline data for women barely existed.

“That was a shocking moment for me,” she said.

Her company is building yarn-based sensors embedded into underwear that monitor biomarkers connected to reproductive health, tracking things like discharge, cycle changes, ovulation patterns, and eventually broader hormonal and menopause-related signals. But what stood out was not just the technology itself. It was the reason it needed to exist at all.

Many modern AI systems are only as accurate as the datasets they’re trained on. If women’s bodies were historically underrepresented in research, then the intelligence layered on top of those systems inherits the same blind spots. The issue is not that AI is biased on purpose. It’s that incomplete systems produce incomplete intelligence.

Designing for the People Who Were Ignored

That same pattern showed up outside healthcare too.

Designer and founder Katie McIntyre spoke about discovering how much of automotive design has historically been engineered around male bodies, from crash testing assumptions to seatbelt positioning. Instead of waiting for the industry to change, she started building her own EV company.

“If you can’t force them,” she said, “build it yourself.”

Part of her work involved redesigning seatbelt systems around differences in female anatomy, particularly softer tissue distribution and pelvic structure. In retrospect, the problem sounds obvious. What’s harder to understand is how something so fundamental remained overlooked for decades inside one of the largest industries in the world.

Katie spoke about realizing that many automotive standards were built around male-centered assumptions that had simply gone unquestioned for years. Crash testing, safety positioning, and even broader design choices often treated the male body as the baseline. Her response wasn’t just to critique the industry, but to build something different from the ground up.

That became one of the recurring themes of the night. Many of these gaps persist not because the solutions are impossible, but because industries normalized designing around a narrow default human for so long that alternative perspectives started being treated as niche instead of necessary.

AI Won’t Fix a System It Learns From

Near the end of the panel, Sarah-Beth Bianchi asked what the speakers hoped the future data story would become from here. Interestingly, most of the answers were less about technology itself and more about participation.

Parnian spoke about helping women connect the dots between lifestyle, exercise, nutrition, menstrual health, and broader reproductive systems. Rebecca emphasized that HerSay was never intended to replace doctors, but to help patients become more active participants in their own care. Katie focused on inclusivity, using data to move systems forward rather than reinforcing older assumptions through newer tools.

The conversation around AI followed the same logic. None of the panelists framed technology as the solution by itself. If anything, they were careful about the opposite. AI can process information, recognize patterns, and accelerate testing in ways humans never could, but it cannot create empathy on its own, nor can it repair trust by itself. And if it is trained on incomplete or biased systems, it can just as easily scale those flaws.

The deeper question sitting underneath the conversation was who gets included in building these systems now.

Katie put it simply near the end of the night:

“Women are not niche. We are half of humanity.”

That line lingered because it reframed the entire discussion. The event wasn’t arguing for special treatment or entirely separate systems. It was pointing out how unusual it is that designing around half the population still feels innovative in the first place.

The technology mattered. The startups mattered. But the deeper shift happening in the room felt cultural. For a long time, women were expected to adapt themselves to systems that were never fully designed around them. Increasingly, people in rooms like this are deciding to rebuild those systems instead.

TL;DR: The Week 2 workshop was on the demo, and the through-line was conviction: investors and customers read whether you actually believe what you’re saying, and you can’t fake it. Harry Gandhi spent the dinner answering the obvious next question, which is how you hold that belief when most of what you hear is no. His answer was a single idea he calls egoless ambition: care about the outcome completely, and treat the attempt as just another shot, both at once. He’s earned the right to the claim. He’s been a researcher, a founder who ran a company for six and a half years until COVID killed it, and an investor at 1517 Fund, and he’s now building robots around his own theory of cognition. What follows is less a biography than the framework he laid out, and why he thinks it’s the thing that actually lets people build.

The second dinner of the S26 cycle landed on the same night as a workshop about the demo, which made the pairing useful. The workshop’s core claim is that a pitch doesn’t exist to prove your company works; it exists to get you the next conversation. What carries it is conviction, and you can't fake that. The obvious follow-up question, the one a room of early founders actually needs answered, is how you generate and hold that conviction when everything around you is telling you to quit. Harry spent most of the evening on exactly that.

He’s an unusual person to answer it, because he’s sat in every seat. He led the creation of what became Velocity Science out of a frustration that researchers with good ideas had no path to build anything. He founded a glucose-monitoring sensor company and ran it for six and a half years. He spent a stretch as an investor at 1517 Fund, the same people behind the Thiel Fellowship he’d done in 2013. So when he talks about the psychology of pitching, it isn’t theory. He’s been the person pitching, the person being pitched, and the person who walked away from the safe version of all of it.

The contradiction at the center

Harry’s term for it is egoless ambition, and he knows it sounds like a contradiction. He reaches for basketball to explain it. Picture a player at the free-throw line, game seven, the shot to win a championship. If “I have to win this” is the thought bouncing around their head as they release, the pressure is too much and they miss. The players who make it do something stranger: they care enormously about the outcome and treat the shot as just another shot at the same time. Both at once.

Founders need the identical split. This pitch matters, you need to close this investor or this customer, and it’s just the next one. The freedom that comes from the indifferent half is what gives you the better shot. He used a second image for it, the one about sand: the tighter you try to grip it, the faster it runs out of your hand. Holding on harder is the thing that makes you lose it.

Why it works, and where it comes from

The reason egoless ambition is a building tool and not just a calming technique is that the fear leaks. As Jesse put it in the workshop, when you pitch something scared or uncertain, it comes out in the pitch, and customers and investors and the people you want to hire all pick up on it. You can’t hide it. So the work of holding the outcome loosely isn’t self-help; it’s the difference between a pitch that reads as conviction and one that reads as someone hoping to be talked out of doing it.

Harry traced where he learned it, and it wasn’t in a company. It was competitive badminton, years before any of the startup stuff. The thing a sport does, or anything that pushes you to the edge of what you can do, is put you on the path to the frontier, and that’s the same place the flow state lives. The two go hand in hand. The person who can be locked in and unattached to the result at the same time is the one operating at the top of their ability.

Jesse pointed at a sharper version of it through a young local hockey player he knows who went in the top five in the NHL draft. The kid isn’t a physical outlier. What he has is the ability to care intensely and let go of everything around the moment, and his fallback was always just “if it doesn’t work out, I’ll go back to the farm.” That escape hatch, held honestly, is part of what unlocked the performance. Harry had his own version: midway through his first company, IBM offered him a job, and the quiet knowledge that he’d be fine if the company failed was part of what let him keep swinging at it.

The Canadian tax on conviction

The workshop named the local obstacle directly, the tall poppy reflex, the apology built into the way Canadian founders take up space. Harry’s framing of it was that there isn’t much reinforcement here for taking a chance; the default question is closer to “why would you?” It’s why founders who move to San Francisco often describe the shift as suddenly feeling normal. The belief was always there; it just stops being penalized.

He added a cultural angle from his own background that reframes the whole thing as a question of normalization. He grew up in a Gujarati family where business ownership was simply the water everyone swam in, where failure meant a cousin gives you a job, you lick your wounds, and you go again. When that’s normal, the risk stops reading as risk. His point for the room was that this is the only real lever: entrepreneurship gets normalized a few people at a time, by being around it until it stops looking crazy. That, in a sentence, is what a room like this dinner is for.

When the experience works against you

The most counterintuitive thing he said was that having been an investor did not make him a better founder. It made one thing easier: he closed his pre-seed in about three weeks by calling people he’d done deals with, which he was clear a first-timer can’t replicate. But the muscle a VC builds is judgment, the constant evaluation of other people’s work, and that muscle is close to useless when you’re the one who has to physically do the thing.

With all his pattern recognition, he still fell into the same trap as the first time around: spending too long chasing research milestones because the technical work was comfortable, when he should have been talking to customers. The lesson he drew is that no advantage substitutes for the actual work, and the comfortable kind of work is the one to be suspicious of.

What he’s building, and why it’s a startup

In early 2023 Harry started doing cognitive-science research full time, relearning the mathematics, physics, and cognitive science he needed to build his own theory of cognition. By the end of that year he’d encoded the theory into robots, and they worked, which he was candid about not having expected. That forced a choice: nonprofit or startup.

He picked startup with a blunt rationale, that charity means perpetually begging for money, while raising venture is comparatively easy when you’ve sat on the other side. He incorporated Lumen Research Labs two months ago, turned several of his math and physics mentors into teammates, already has a construction company asking to integrate the work, and is looking for robotics engineers. He’s also indifferent, by design, to the swing between the day the robot smacks into a glass wall and the day a customer calls. The point isn’t the day. The point is the craft.

Key Takeaways

Egoless ambition is the whole framework. Care about the outcome completely and treat the attempt as just one more attempt. The pressure of needing to win is precisely what makes you miss, and the freedom in the indifferent half is what produces the better shot. Hold it like sand: loosely, or it runs out.

Conviction can’t be faked, because fear leaks. When you pitch scared, it shows up in the pitch, and everyone you’re trying to win over feels it. The work of holding the result loosely is what lets genuine belief come through, which is the one signal investors can’t manufacture or ignore.

Build the escape hatch so you can ignore it. The honest knowledge that you’ll be fine if it fails, a job to fall back on, a life that’s worth it either way, is what frees you to swing hard. The NHL prospect and the founder both perform better for having a floor they never intend to use.

Risk is mostly a story about what’s normal. Entrepreneurship feels dangerous where it’s rare and ordinary where it’s everywhere. You can’t legislate that into a culture; you normalize it a few people at a time, which is exactly what gathering founders in a room does.

The comfortable work is the work to distrust. Coming from the investor’s side made Harry better at raising and no better at building, and he still hid in research milestones because they were familiar. Whatever your background, the founder’s job is to do the uncomfortable thing, which is almost always talking to customers sooner than you want to.

The S26 Founder Dinner Series is hosted by Builders Club in Waterloo. Sessions pair evening founder dinners with midday workshops. Thanks to our sponsors Osler, TD Innovation Partners, and Communitech for their continued support.

TL;DR — Adi Patel runs Clearline, an AI-native operating system for car dealerships, with his brother and co-founder Abhi as CTO. They went through YC in Summer 2022 as Lancey, a front-end demo cloner. Lancey pivoted into LLM-powered feedback management, scaled to 50,000 users, and got caught in a token-pricing arms race. Adi shut it down. Clearline is the current bet: voice AI for an industry that has never bought AI before. The dinner covered what it actually looks like to kill something that’s working, why Clearline operates out of a Kitchener office one floor below Builders Club, and how a young non-technical CEO walks into automotive trade shows and walks out with serious contract conversations.

The first Founder Dinner of the S26 cycle. A long table, a full room, and the kind of conversation that only happens when the speaker is close enough to the work to still be in it. Adi didn’t have to travel far. Clearline works out of an office in Kitchener directly below Builders Club, which means most of the room has walked past their door at some point this year. That proximity showed up in the conversation. Several of the questions weren’t hypothetical; they were the questions you ask the team you actually share a building with.

Adi is the co-founder and CEO of a YC S22 company that has pivoted twice. Clearline is where they’ve landed, and it’s in the middle of the customer conversations that will determine whether the bet pays off. He talked about all of it openly, which set the tone for the rest of the evening.

From Lancey to Clearline

Adi and Abhi started Lancey in 2022 as a front-end cloning tool. It was the kind of thing engineers built when GPT-4 made it possible to scrape a website and stand up a working demo in a few minutes. It was useful. It also wasn’t a company.

The first pivot came through customer feedback. Lancey moved into feedback management, using early LLMs to help product teams parse signal from noise across user inputs. The product worked. It scaled to 50,000 users. Revenue was decent. By most early-stage metrics, this was a success story.

It was also, in Adi’s words, undefensible. The core mechanic was token-based pricing on top of a foundation model. Every quarter a new competitor showed up with better prompts and a thinner margin. The product was a wrapper, and the wrapper economy had stopped being a place where good companies got built.

Killing a working product is harder than killing a failing one. The reflex is to keep going because the numbers don’t tell you to stop. Adi stopped anyway.

Why Car Dealerships

Clearline is sharply scoped. The product is an AI-native operating system for car dealerships, built around three pieces: an inbound voice agent that answers every sales and service call, an outbound system that runs disciplined follow-up cadences from day one through day ninety, and a CRM that logs everything so managers actually know what’s happening across sales, service, and the back office.

The numbers in the dealership world are absurd in the way that markets ignored by software usually are. Twenty-three percent of dealership calls go unanswered. Eighty-five percent of those callers never call back. Lead follow-up typically dies by day five. The existing stack is fragmented and nothing talks to each other. Clearline’s early customers are recovering sixty thousand dollars or more in their first thirty days.

The thesis underneath the wedge is broader. Most of the durable AI value over the next decade lives in industries that haven’t seriously encountered modern AI yet. Not SaaS dashboards. Not knowledge-worker copilots. The physical-world economy: service businesses, logistics, retail operations, automotive. The places where the existing tech stack is a phone tree and a clipboard. Voice is the entry point. The CRM is the lock-in.

Selling Into Industries Without AI

The most useful thread from the dinner was how Adi finds and closes customers in an industry that has never bought AI before.

One of the larger contracts now in flight, a 200-plus-location automotive chain, came out of a 400-person aftermarket automotive conference. Adi was the youngest person in the room by a meaningful margin. He used that. People wanted to talk to him because he was curious-looking, not threatening, and because he wasn’t there with a slide deck. He was there asking questions. The conversation started from a hallway introduction and is now three months in.

A few patterns came out of the broader conversation about selling into AI-naive industries. The first is that you can’t lead with the technology, because nobody on the other side has a reference point. You lead with the outcome and let them ask how it works. The second is that ROI alone doesn’t close deals at the operations level. The decision-maker is a regional manager with a bonus structure and a career path. Helping them get promoted matters as much as the cost savings. The third is that the existing AI exposure of your buyer is almost always invisible to them. They use Google Maps, Netflix recommendations, fraud detection on their credit cards. Walking them through what they already trust is more effective than walking them through what you’re building.

A Floor Below Builders Club

Clearline operates from Kitchener on purpose. The reasoning is operational, not sentimental. First-year engineers come in at a fraction of the cost of comparable hires in San Francisco. The talent pool is technically deep. The team is on a five-day in-person policy, communicated up front in job applications, and that filter works in this city in a way it doesn’t elsewhere.

Adi’s co-founder and CTO is his brother Abhi. The company is committed to the location. The office is one floor below the room where this dinner happened. That kind of density, where a YC company and a founder program share a building and most of the founders in the room recognize each other from the elevator, is the thing that makes a place actually compound over time. It’s also the thing that’s hardest to engineer on purpose.

What Adi’s Presence Represented

The first dinner of a series sets the temperature for the rest of it. The room this year is largely founders at the earliest stage. Adi is a few years further along, and he can still describe the early stretch clearly enough that the lessons translate. He talked about killing a product that was working, what it actually looks like to sell into an industry that’s never bought AI, and what it took to get from a YC demo to a company with customers. None of it was abstract.

That’s the version of founder storytelling this series exists for.

Key Takeaways

Working is not the same as defensible. Lancey hit 50,000 users and meaningful revenue, and Adi shut it down anyway. The signal he trusted was structural, not metric: every quarter a competitor showed up with the same product and a thinner margin. A growing wrapper is still a wrapper.

Physical-world AI is an education problem before it’s a technology problem. Most of the addressable market for AI in service industries hasn’t bought AI before. The sales cycle is long because you’re teaching, not pitching. The companies that win this wave will be the ones who learn to sell into curiosity rather than urgency.

Show up where your customers already are, not where founders already are. A 400-person aftermarket automotive conference is not a place where AI startups hang out. That was the point. Adi was the only one in the room talking about what his product did, and he was the youngest person by twenty years. Both of those things were assets.

Sell to the person, not just the company. Operational buyers in mid-market industries have careers, bonuses, and personal stakes. ROI gets you in the room. Helping them get promoted closes the deal. Founders who only optimize for the spreadsheet miss the human variable that decides most contracts.

Density beats geography. Clearline operates one floor below Builders Club in Kitchener. That arrangement isn’t an accident. Cheaper engineering, deeper technical pool, a culture that supports in-person work, and the kind of accidental encounters that turn into customers and team members. Distributed teams are a strategy. Being physically close to other builders is a different one, and it compounds differently.

The bet that matters is the one you can articulate clearly. Adi can say what Clearline is in one sentence: AI for the physical economy, starting with car dealerships. That clarity didn’t come from a positioning workshop. It came from pivoting twice and learning what each version taught him about where the durable value lives.

The S26 Founder Dinner Series is hosted by Builders Club in Waterloo. Sessions pair evening founder dinners with midday workshops. Thanks to our sponsors Osler, TD Innovation Partners, and Communitech for their continued support.

The Waterloo Thesis is simple. The talent has always been here. The system that produces it has always been here. What’s missing isn’t builders. It’s the infrastructure to recognize and back them before someone else does.

Most of Canada has tried to answer with structured process. Programs, intakes, milestones, metrics, gates. The same shape, repeated in every region, optimized for legibility instead of motion. By the time the system is ready to act, the best builders are already somewhere else. Funded, focused, and far from here.

It just doesn’t work.

Waterloo has always been the place where a different way is possible. That’s still true. And it’s why Builders Club and Communitech are working together on some things now. The shorthand version: two organizations who both see that what worked for the last era isn’t going to work for the next one, doing something about it from different angles.

The structured process is not the answer

Builders going zero to one don’t need another intake form. They don’t need another six-week curriculum. They don’t need another stage to perform on.

They need to be close to other people doing the same thing, in rooms where trust forms through proximity instead of credentials. They need access to people who’ve shipped, raised, sold, failed, and started again, without having to apply for it. They need to be able to start before they have permission to start.

That’s what the structured process can’t deliver. It was designed for a slower, more legible version of building, where stages were predictable and support could be programmed. AI is rewriting the practice every day. What one person can ship, what a small team can hold, what early even means. None of it is fixed anymore. The playbook from two years ago is already half-obsolete.

A program can’t move fast enough to keep up. A community of builders can.

What Builders Club is

In just over a year, Builders Club has had over 500 applications. The membership (free + professional) has grown past 400. The newsletter has 4,000+ subscribers. None of it was marketed in the usual sense. People found us, because the shape was already what they were looking for.

It's a community shaped by its members, not designed for them. Evolving as fast as the practice does, connected back to the grassroots that built this ecosystem in the first place. The earliest versions of what we now call infrastructure here all started this way. Rooms, dinners, side projects, people who didn't ask for permission. Builders Club is the current expression of that same impulse, built for builders going zero to one in 2026 and beyond.

The mix in the room is the point. Independent operators. Remote workers earning U.S. salaries from Waterloo. Mid-career people who have shipped before and are now building again with a new set of tools. Founders building companies that don’t fit a neat classification because the categories themselves are moving. They use the leading tools daily. They learn from each other faster than any curriculum could teach them. The mix is not curated by a program. It assembled itself, because this is where these builders want to be.

That’s the shape. And it’s the shape that fits the moment.

Working together: Builders Club and Communitech

Communitech has scale, history, and reach. Its role is increasingly about being the connective tissue across the region, bringing founders, startups, corporates, institutions, government, and talent into closer proximity as the next generation of companies emerges. Builders Club is something different. It’s the activation layer the Waterloo Thesis has been waiting for. Closer to the grassroots that built this ecosystem, fast enough to move with a practice that changes every week, shaped by builders rather than designed for them.

Those are different roles by design. Each of us doing what only we can do, pointed at the same builders.

Sheldon McCormick, who came in as Communitech’s CEO last year, has been part of this conversation for months. The same question on every call: how do we meaningfully support people going zero to one, right now, in this moment. No theatre, no MOU dance. Communitech is moving toward a more adaptive way of supporting the earliest stage too, and that’s what makes this work. We’re starting with a few specific things and the shape of the support will keep evolving because the practice does.

That’s what working together means here. Two organizations who see the same opportunity in Waterloo and are doing something about it.

Why Waterloo

The Waterloo Thesis has always said the talent is here. Builders Club is what activating it looks like. Communitech working with us on that is what recognition looks like.

We need to find a different way to support what’s coming next. The old shape was built for a world that’s gone. The new one is being built right now, in rooms full of builders who don’t have a playbook and don’t need one.

This is what we’re doing. Together.

— Jesse

TL;DR: Canada’s startup community is staging a national fight over a $750M federal venture envelope that’s smaller than the AUM of one Canadian-founded pre-seed fund (Afore Capital, $500M USD). Multiple coalitions — CVCA, NACO, the brand-new CSCA — are competing for slices of a pot that’s the wrong size, pointed at the wrong stage.

Growth capital isn’t the constraint. The market funds good growth-stage companies. The real constraint is at the start, where ownership is cheap and returns compound for decades. And we keep showing up there with grants instead of cap table positions — treating early support as charity instead of investment.

We’re trying to build a 10,000 sq ft house on a 10x10 lot with no foundation. The work is expanding the lot (regulatory) and pouring the base (early-stage investment, not grants). Neither photographs well. Neither produces a slide-ready number next year. Both are the actual job.

Stop forming coalitions to talk. Build.

Afore Capital manages $500 million USD. That’s stated on their website. At today’s exchange rate, it’s north of $750 million Canadian.

Afore is a pre-seed fund. It was co-founded by Gaurav Jain, a University of Waterloo alum.

One firm, founded by someone from our backyard, manages more capital than the entire pot Canada is currently staging a national debate over.

That’s the whole problem in one sentence.

The cottage industry around the envelope

The fight over how to split the federal envelope has already produced its own cottage industry. The CVCA, representing 340-plus private capital firms, wants the $750M deployed to growth-stage companies — Series B and beyond — arguing Canada’s gap is at scale. NACO, representing the angel side, says the gap is actually at pre-seed and seed, and wants $500M of the envelope going to a matching program for early-stage funds. As of last week, there’s a third organization in the room: the Canadian Startup Capital Association, launched April 22, with 19 founding members and a proposal to split the difference. And those are just the three with the loudest current press cycles. There are more.

Multiple coalitions. One pot of money. A pot of money smaller than the AUM of a single fund founded by a Canadian operating out of California.

Let that sit.

The CSCA’s own founding members claim to have collectively invested more than $750 million into early-stage Canadian startups already. The coalition formed to debate how to split a federal envelope is, on its own balance sheet, the size of the envelope.

(Quick housekeeping: the CSCA was founded by Jesse Wiebe. I’m Jesse Rodgers. Different Jesse. He’s doing real work. So is everyone in this story. Jesses are amazing. That’s part of what makes this so frustrating to watch.)

I’m not writing this to attack the $750M, or any of the people fighting over it. The intent is good. The people are working hard. This isn’t about the number being bad. It’s about the number being small, the conversation being small, and all of it pointed at the wrong stage of a problem that has almost nothing to do with how the envelope gets split.

The 10,000 square foot home on a 10x10 lot

Here’s what I think we’re actually doing.

We’re trying to spec out a 10,000 square foot home on a 10-by-10 parcel of land with no foundation. Everyone’s arguing about the countertops and the roofline. Nobody’s pouring concrete. And the kicker, the foundation we’d need requires a bigger lot than current rules allow. We are literally not permitted to build the base that would support what we say we want.

So we keep designing the house. Beautiful renderings. Press releases. New coalitions announcing they’ll help design the house. Existing organizations repositioning to claim a piece of the design budget. The lot stays 10-by-10, the ground stays soft, and nothing actually gets built.

Ownership compounds backward

Now let’s talk about ownership, because this is the part most people skip.

Canadians should own pieces of the companies built here. That’s the whole point of any of this. But ownership compounds backward from when you got in. The biggest returns — the ones that move generational wealth, that capitalize the next decade of builders, that create the flywheel everyone says they want — go to the people who wrote the first check. Not the tenth. Not the twentieth.

A growth-stage envelope is buying in late at a markup. The market already handles that stage. Good Canadian growth-stage companies get funded. They always have. Foreign capital fills the gap, yes, and that means the upside flows out of the country. That’s a real problem. But it’s a downstream problem. By the time you’re trying to fix it at Series B, the ownership math is already lost.

The constraint isn’t there. The constraint is at the start.

The grant trap

And here’s where it gets worse: even when we do support the start, we hand the money out as grants. Non-dilutive funding. SR&ED. IRAP. Programs that say, in effect: here’s some cash, go build something, we don’t want a piece. We treat the earliest, riskiest support as charity instead of investment. And then we wonder why the upside leaves the country.

Think about CDL. Fourteen years of operation. Hundreds of companies through the program. Real outcomes. Now imagine if, alongside CDL, there had been a sidecar fund — public capital, taking small early positions in the cohort. Not picking winners, just participating in the surface area CDL was already creating. Run the math on what that would have returned by now. Compare it to what the same dollars produced as grants and program funding.

I’d bet the sidecar wins by an order of magnitude. And the returns would have recapitalized the next fourteen years of foundational work, instead of disappearing into a sunk-cost line item we don’t even bother to measure.

This is the pattern we keep repeating. We give early founders money with no strings, congratulate ourselves for being supportive, and then watch the equity compound somewhere else. By the time anyone in Canada wants to own a piece, the price is twenty times higher and we’re calling it a $750M growth fund.

Early support shouldn’t be charity. It should be investment in our own future. The country writing the first check should be on the cap table.

The leaky bucket and the lot underneath it

Jesse Wiebe at the CSCA had a line in his launch interview that’s stayed with me: “We have such a leaky bucket in Canada right now, I’d rather plug the holes first before we start pouring more water into it.”

He’s right. The bucket is leaky.

Companies get started here and move south. Founders raise their first round in Canada and their second in California. Promising IP comes out of Canadian universities and ends up commercialized somewhere else. Talent leaves. Capital leaves. The upside leaves. By the time anyone in Canada wants to buy in, the price has tripled and the cap table is full of US funds.

That’s the bucket. And plugging those holes — keeping more of what we start, more of what we fund, more of what we build — is genuinely important work. Wiebe is doing the right thing by naming it.

But I’d push the question one level further.

The bucket is leaky because the foundation underneath it is wrong. The structural conditions that cause companies to leave, that cause capital to flow out, that cause founders to relocate, those aren’t bucket problems. They’re building lot problems. They’re foundation problems. Plugging holes in a bucket sitting on a 10-by-10 lot of cracked earth doesn’t change the lot. Eventually the bucket falls over, or the next bucket cracks in the same spots.

You can spend the next decade patching, and the leaks will keep finding new places to come from. Or you can do the harder, slower, less photogenic work of fixing what the bucket is sitting on.

Both matter. But only one of them compounds.

The honest part nobody says out loud

You can’t draw a line from this dollar to that outcome. You can’t promise a timeline. You might not see the house in your career. This is why we keep defaulting to growth-stage announcements and new coalitions, they’re legible. They photograph well. You can cut a ribbon. You can put out a press release. You can convene a roundtable.

Foundations don’t cut ribbons. Pre-seed checks don’t make headlines. Removing the regulations that constrain the lot size won’t trend on LinkedIn.

Legibility is not impact. We’ve confused them for a long time and it’s costing us the thing we say we’re trying to build.

Who this isn’t aimed at

Not the founders. Not the civil servants.

The people in government working on this have been handed an impossible task with the wrong tools, and asked to deliver something legible on a timeline that doesn’t match the work. They are doing their best with what they know. Most of them care more than they get credit for.

And the founders pushing back aren’t wrong about the substance. Canadian policy has under-served builders for a long time. The frustration is earned.

But the way the two sides talk to each other isn’t working. The founder posture has been ungenerous — dismissing every government effort as proof that government can’t help, treating civil servants as obstacles instead of people trying to solve a hard problem with limited room to move. The government posture has been performative — announcing programs, convening roundtables, producing reports that signal activity without producing outcomes, and then getting defensive when builders point that out.

Both sides are responding to a real thing in the other. Neither side is fixing it.

The disrespect runs both ways. It serves nobody. The work doesn’t get easier when we keep talking past each other. Fix that, and the rest of this becomes possible.

What foundational work actually means

It means expanding the lot, the structural conditions under which something can be built. Right now those conditions are constrained by rules written for a different era and a different ambition. That’s the work. Not another fund. Not another coalition. Not another roundtable. The deeply unglamorous job of changing what’s structurally possible so that builders can build.

It means pouring the base, supporting the earliest, riskiest, least photogenic work, and doing it as investment rather than charity. Pre-seed. Seed. Sidecars. Cap table. The stage where the market doesn’t reach and where Canadians could actually own meaningful pieces of what gets built here, for the next forty years.

Neither of those things will produce a number you can put on a slide next year. Both will produce, twenty years from now, the houses we keep saying we want.

Build. Now.

We don’t need another organization to talk about this. We have rooms full of people talking. We have op-eds, including this one. We have studies and panels and working groups and now a coalition of coalitions. The talking layer is fully staffed.

What we need is to build. To pour the foundation. To expand the lot. To put serious effort and serious capital at the stage where ownership and impact actually compound. To stop staging fights over the wrong number at the wrong stage.

The $750M isn’t the problem. The problem is treating it like the answer.

One Canadian, with one fund, manages more than that already. Imagine what happens if the ground beneath the next ten Gauravs is solid before they have to leave to find it.

Build. Now.

TL;DR: The W26 Founder Dinner Series ran from January through March, pairing midday workshops with evening dinners across six Tuesday sessions in Waterloo. Speakers ranged from a robotics founder still getting his hands dirty in apple orchards to a Shopify engineering veteran now running a brewery in Elora. Each dinner was its own thing: a different person, a different set of scars, a different version of the same underlying question about why you do this. The through-line was harder to name than any single theme, but it was there: the work is the point, and the people who last know that.

The series started with a simple premise: bring a small group of early-stage technical founders into the same room, repeatedly, over a winter session. Give them a workshop with something to take away. Then seat them at a table with someone who has actually done it, and let the conversation go where it needs to go.

That’s a harder thing to program than it sounds. Most founder events default to polished panels or carefully managed Q&As. This series was neither. Six dinners, seven speakers, and three months of showing up on Tuesday.

Matt Stevens: Build for the Economics, Not Just the Problem

Matt Stevens opened the series in exactly the right register. He’s the co-founder of Finite Robotics, building orchard robots for apple thinning. Nearly two decades in electric mobility and sustainability, a PhD from Waterloo, a company sale to Geotab behind him, and now he’s also a farmer. The economics of agriculture, he explained, make robotics inevitable: labor can represent more than half of total production costs. Understanding the customer’s cost structure, not just their workflow, is what gives the product direction.

His broader vision goes past the thinning robot. Lower the labor costs of farming and you can grow more diverse, higher-quality food locally. That kind of thinking, grounded in both the technical and the economic reality of the industry, set a tone for the series. Matt didn’t come in with a deck. He came in with context.

Read the full recap: Matt Stevens on Robotics for Agriculture

Humza Ahmed and Michael Litt: Two Angles on Building Durable Companies

Week 2 doubled the perspective. Humza Ahmed, founder of Automax.ai and a Y Combinator company, brought the view of a technical founder working in a complex, regulated market. Property valuation is not a simple problem to automate; the hard parts are compliance, trust, and workflow integration, not the AI itself.

Michael Litt, co-founder of Vidyard and a general partner at Garage VC, offered the longer arc: a decade of building Vidyard from zero, and now the investor-side view of what separates founders who build durable companies from those who don’t. His position on AI was direct: it changes the speed of iteration, not the fundamental problem of creating value. The pressure on product quality is higher now, not lower. You have to be the best product to win. That bar hasn’t moved.

Read the full recap: Michael Litt and Humza Ahmed on Building Through Different Eras

Mike Kirkup: Staying in the Game

Mike Kirkup co-founded Elderella and has spent years coaching early-stage founders in Waterloo. His session covered something that doesn’t show up in pitch decks: the mental cycle that traps founders who can’t separate their identity from their company’s performance. Overproduction, breakdown, paralysis, repeat. He has seen it enough times to describe it with precision.

His point was not only motivational, it was practical. Founders who visualize a company as alive, as a thing that will exist and matter, make different decisions than founders who are managing against failure. The ones who last are not the ones with the best plan; they are the ones who can stay in the room long enough to learn what the plan actually needs to be.

Read the full recap: Mike Kirkup on Building AI-Native Products at Breakneck Speed

Brad Murray: Craft at Scale

Brad Murray was one of the first engineers at Pebble, where he helped build the OS from scratch, co-founded Beeper, and has since joined OpenAI. He is one of the more technically serious builders Waterloo has produced, and the dinner with him was the kind where the conversation doesn’t really stop.

Brad’s version of the evening was grounded in craft: what it actually takes to build systems that work at scale, how early technical decisions compound over time, and how the culture around code matters as much as the code itself. For a room full of builders, it was the right conversation at the right moment in the series.

Read the full recap: Brad Murray on Building Things That Last

Hongwei Liu: The North Star Doesn’t Move

Hongwei Liu is the co-founder and CEO of Mappedin, which powers indoor mapping for malls, airports, and major venues globally. He has been building the same company for over a decade, which puts him in a small category.

His story covered the early days of driving across Ontario to pitch a casino that wanted to map its slot machines, and the pandemic years when every customer’s building was closed and Mappedin’s revenue somehow kept climbing because the relationships were real. His north star, map every building, never changed. Everything around it shifted constantly. That distinction, between a fixed destination and flexible execution, was one of the cleaner ideas the series produced.

He also had a clear view on selling: it is a skill, not a personality trait. He got better at it intentionally, the same way you get better at anything. The founders in the room who thought they were not salespeople heard that.

Read the full recap: Hongwei Liu on Playing the Long Game

Jim Murphy: Why You Do This

The series closed with Jim Murphy: Boltmade, acquired by Shopify; a key part of building Shopify’s Waterloo engineering organization; now running Elora Brewing Company. He is 25 years into building, which gives him a kind of clarity about what actually matters that is hard to manufacture.

The dinner conversation covered a lot of ground, including VC, wealth creation, and the gap between the effort that went into fundraising and the outcomes that actually followed. His observation was personal, not prescriptive: most of the grinding happened while chasing external validation, and most of the actual gains came when the focus was on the work and the customer in front of him. The brewery, he said, taught him more about unit economics and planning discipline than most of his software companies had, because the business demanded it.

He closed the evening with a question the series had been building toward all series: why do you do this? Not for the money, not for the validation. The people in this room who make it to the other side will have an answer that holds up.

Read the full recap: Jim Murphy on Capital and Commitment

What Carried Through

Seven speakers across six dinners is not a curriculum; it is more of a sample. But certain things repeated often enough to qualify as patterns.

The founders who built something durable stayed close to real customers from the beginning. They treated selling as a skill to develop, not a task to delegate. They held a clear long-term direction while staying genuinely flexible about how to get there. They understood the economics of the business they were in, not just the product. And they had, at some point, stopped measuring themselves against external signals and started measuring against the work itself.

Those are not original ideas. But hearing them from people who have actually lived them, across a table, over three months, is different from reading them anywhere else. That is what the series is for.

The Spring Series Is Open

The next cohort runs May through July. Same format: six Tuesday sessions, midday workshops, evening dinners with founders who have actually done it. Small group, curated for people who are actively building and willing to engage.

If W26 sounds like the room you want to be in, applications for the spring series are open now. Apply here.

Key Takeaways Across the Series

Understanding your customer’s economics is more valuable than understanding their workflow. Matt Stevens spent two decades in electric mobility before moving into agriculture. When he understood that labor represents more than half the cost of running an orchard, the product direction became obvious. The best technical founders don’t just solve the usability problem; they solve the business problem underneath it.

AI has changed the speed of the game, not the fundamentals. The point surfaced in multiple sessions. The pressure on product quality is higher because the bar for shipping has dropped. Speed is a commodity now. Value is not.

The founders who last are not the ones with the best plan. Several speakers returned to the question of what keeps a person in the game during the hard stretches. Staying in contact with real customers, holding a clear north star, and resisting the loop of managing against failure all appeared repeatedly as the actual durability mechanisms.

Proximity to customers beats abstraction every time. Hongwei Liu drove across Ontario to close his first deal. Jim Murphy locked in his first brewery customer before the doors opened. Both built something that lasted. Early revenue from real customers is a forcing function that no amount of planning replicates.

Chasing external validation is expensive. More than one speaker described a period where the energy went into the fundraise, the investor relationship, or the perception of traction rather than the thing itself. The wealth creation, when it came, came from somewhere else. The cohort heard this not as advice but as lived experience, which is the only version worth listening to.

The ecosystem is the point of being here. Every speaker in the W26 series is Waterloo-connected in some form. Some grew up here, some chose to come back, some never left. The pattern is not nostalgia; it is compounding. The founders who came through this program sit inside a network that is now three months deeper than when they arrived. That is the actual return on a winter session.

The W26 Founder Dinner Series is hosted by Builders Club in Waterloo. Sessions run every two weeks through the winter session, pairing evening founder dinners with midday workshops. Thanks to our sponsors Osler and TD Innovation Partners for their continued support.

TL;DR: Jim Murphy has been in and around the Waterloo startup ecosystem since before it was called an ecosystem. He built a product company, a services firm, a brewery, and a farm operation, while also passing through Google and Shopify along the way. The throughline across all of it: a deep skepticism of external validation, a hard-won appreciation for customers over capital, and a conviction that the barriers founders believe in are mostly imaginary. The final session of W26 ended where it should have: with a founder who had done the reps reminding a room of founders just starting them that the work is the point.

Coming Home

Jim graduated from Waterloo in 1995 and did what most technically ambitious people did at the time: left. Texas first, then Boston, New York, California, back and forth across the US for fifteen years. He was building a network, working on software, and accumulating the kind of experience that, at the time, felt like it could only happen somewhere other than here.

He came back in 2008 because his wife made a compelling case. Three kids, two families in Waterloo, a life that made more sense closer to home. At the time, Jim thought it felt like a sacrifice. A step backward. The career equivalent of admitting that the bigger game had passed you by.

It wasn’t. Coming back in 2008 meant arriving in a Waterloo that was just beginning to find its own footing. Smaller than Silicon Valley, obviously. Less developed, less transactional, less polished. But that turned out to be the point. In a scene that size, relationships move faster and mean more. Jim knew people, people knew him, and that mattered in ways that a fully scaled, fully saturated market can’t replicate.

What he found wasn’t a rear-view-mirror version of the city he’d left. It was something earlier and more interesting: a community of people writing equity lines of credit on their homes to invest in their friends’ companies. Real skin in the game. Real belief. The kind of thing that looks naive from the outside and essential from the inside.

Postrank and an Exit

Back in Waterloo, Jim got involved with a company called Postrank. The connection came through StartupCamp Waterloo, a community event in the same spirit as what Builders Club runs today: the right people in a room, no agenda, things happening because of proximity and trust rather than formal introductions.

Postrank was founded by Ilya Grigorik, another Waterloo grad, building a social media analytics platform at a moment when that category was still being defined. The work was interesting, the team was strong, and it was exactly the kind of thing the ecosystem was capable of producing if you looked past the idea that the real stuff only happened elsewhere.

Google bought it and relocated the team to the Bay Area. Jim stayed in Waterloo. Ilya eventually landed at Shopify as a Distinguished Engineer. Another Waterloo thread that found its way back.

Watching that happen, seeing what you built get absorbed and the people around you scatter to California, is its own kind of education. The outcome looks like success from the outside. From where Jim was standing, it was also a clearing: the company was gone, the team had moved on, and he was back to figuring out what came next. He had more experience, a stronger network, and a clearer sense of what he actually wanted to build toward.

Boltmade and the Value of Proximity

When he got back, people kept pulling him in to assess their situations: something’s broken, something’s not quite right, can you help? The problem with that kind of outside help is structural. You can give someone a rough map of what they should do, but there’s no shared trust, no accountability, no motion. You can’t improve a thing you’re not inside.

So Jim built a team that could go in. Boltmade wasn’t quite a traditional services company and wasn’t quite a product studio. It was a group of people who could embed alongside a company, demonstrate how they worked, and do real things alongside real teams. Projects ran six months, roughly. The clients ranged from Xerox PARC to local startups to larger enterprises.

For Jim, it was the ideal environment for that point in his career. He wanted to work on interesting problems with people he liked without the weight of owning the outcome long-term. There’s a tyranny that sets in around year five of a product company, he explained: you can feel owned by the thing you built. Boltmade was, in part, an answer to that feeling.

It also worked as a business. When the room offered the predictable counterpoint, that product companies are the real thing and services are the consolation prize, Jim was direct: Boltmade made money. Real money. Without a single investor.

From Boltmade to Shopify

Boltmade was acquired by Shopify. Jim went with it, spending several years there as Director of Engineering before moving on to the next chapter.

The story of how that came together is one of the better ones shared at the table this winter. You had to be there (apply to the Spring series).

What the outcome represents, though, is worth saying plainly: a bootstrapped services company, built on relationships and craft, acquired by one of the most important technology companies in the country. No fundraising deck. No growth rounds. Just a team doing good work until someone wanted to bring them inside.

On Venture Capital: Demystifying the Gatekeeper

The longest part of the evening, and the one that most directly continued the workshop’s themes, was Jim’s frank assessment of venture capital as both an asset class and a psychological trap for founders.

The asset class argument is relatively clean. VC is illiquid, high-fee, and structurally dependent on a power law that benefits almost no one: a small number of enormous wins have to cover a majority of losses. Jim has seen this from the LP side as well as the founder side. The details of what that’s looked like in practice were for the room.

The more interesting argument is the psychological one. Jim spent the early part of his career treating venture capital as a form of external validation. If a VC writes the check, it means you’re smart enough, the idea is good enough, the plan is credible enough. He wanted that anointment. He worked toward it. And a lot of his hardest stretches came during the periods when he was chasing it.

All of his actual wealth creation, he said, happened during the periods when he wasn’t.

His critique isn’t that VC is useless. It’s that it’s been elevated into the only legitimate path for building a company, and that’s a fiction. The perception that there’s one right way to build something, a SaaS model, a growth rate, a fundraising sequence, and that deviation from it signals failure, is a learned helplessness. It disempowers founders before they’ve even started.

He made a point about status worth repeating: there’s no more fungible commodity in the world than money. Value-added capital is largely a myth. Founders who schlep up to investors in the hope of getting anointed have the power dynamic exactly backward. You are the main event. The capital is looking for the company, not the other way around.

That’s not a counsel against raising money. It’s a counsel against organizing your self-worth around whether or not someone writes you a check.

Building Things That Bleed

Jim started Elora Brewing while he was still running Boltmade. It ran alongside everything else through the Shopify years, and after he left, it became the thing he turned his full attention toward. This part of the story gets told quickly at dinner but carries a lot of weight. The brewery was a deliberate departure from everything software: physical product, low margins, regulatory complexity, bricks and mortar, minimum wage staff, inventory sitting in tanks.

He was terrified by parts of it. The unit economics were nothing like enterprise software. The forecasting discipline required was real: you had to know how much malt to order because there were lead times and cost of goods and limited capital. No fuzzy five-year projections. Actual lemonade-stand math. How much does it cost to make a litre, how many litres do you need to sell, what’s the margin, what’s the plan.

What he found, somewhat to his surprise, was that this kind of planning was clarifying. He could build a model, track it against reality, and manage to it. It gave him a respect for the majority of businesses in the world that aren’t high-gross-margin software: the ones running at 6 to 8% net margin, doing real work, serving real customers, and not pretending that scale is something separate from revenue.

He also had a customer before he opened. The manager at a nearby restaurant agreed to buy everything the brewery produced. That commitment came from proximity and relationship, not from a pitch deck.

What the Series Built

Jim was the sixth and final guest of the W26 series. It wasn’t planned as a bookend, but it worked as one. Matt Stevens opened the series with a story about building real things for real uses, physical robotics for real farms, and a message about getting started before everything is figured out. Jim closed it with a longer arc: 30 years of building across contexts, geographies, and company types, and a consistent conclusion that the work itself is what compounds.

The dinner themes across the series, Start, Talk, Ship, Ask, Charge, Learn, Story, Scale, Commit, are not a formula. They’re orientations. Jim’s presence in the final week, under the theme of Commit, was fitting not because he had a single answer but because he had visible scar tissue from following the question all the way through.

The message he left with the room: you’re more in control than you think. The barriers are mostly invented. If you can’t help yourself, the worst thing you can do is structure your life around passing through a gate held by someone who probably doesn’t know which companies will succeed and is as likely as not to make your path harder.

Go talk to customers. Build toward something real. The rest tends to follow.

Key Takeaways

VC is not validation. Venture capital is a specific financial instrument optimized for a specific return profile. When it works, it works at scale. For most founders at most stages, treating a VC check as confirmation that you’re on the right track is a category error. The investors who matter most tend to be following success, not leading it.

Your wealth creation will happen in the gaps. Jim’s experience, and the experience he observed in others, was consistent: the hard grinding stretches coincided with fundraising cycles. The actual value got built during the periods of direct customer focus, lean operations, and no one else’s timeline to satisfy.

Proximity to customers is the real leverage. Whether he was talking about Boltmade, the brewery, or the farm, the pattern was the same: get close to the people who will actually use or buy the thing. Real relationships, real feedback, real commitment. Not abstractions. Not assumptions. Not investor-ready narratives.

There is no one right way to build a company. The SaaS playbook, the growth-at-all-costs model, the raise-first-figure-it-out-later approach: these are patterns from a specific market moment, not laws of nature. Husband-and-wife teams work. Service companies work. Breweries work. The pattern that doesn’t work is the one where you wait for external permission to start.

Waterloo is a structural advantage, not a consolation prize. Every company that came up during the series as an example of successful building had roots here and customers or partners across North America. The perch matters. Canadian cost structure, access to the US market, a community small enough to have real relationships: these are real advantages, not things to apologize for.

The W26 Founder Dinner Series is hosted by Builders Club in Waterloo. Sessions run every two weeks through the winter term, pairing evening founder dinners with midday workshops. Thanks to our sponsors Osler and TD Innovation Banking for their continued support.

TLDR; Hongwei Liu is not a typical dinner guest for a room full of early-stage founders. He has not pivoted, exited, or reinvented himself. He started Mappedin with a small team and a conviction that every building in the world should be mapped indoors, and he has spent the better part of a decade executing on exactly that. By the time he sat down with the W26 cohort, the company was powering indoor navigation for malls, airports, offices, and major venues globally. The conversation that followed was one of the most grounded of the series: a founder who has been through real turbulence sharing what it actually looks like on the other side.

Week five is where the March arc, Story + Scale + Commit, starts to resolve into something concrete. The first four dinners covered early formation, communication, survival, and default dead-or-alive decisions. Hongwei brought something different: a perspective from someone who had made it through each of those phases and was still standing, still building, and still in the same city.

Mappedin is not a flashy company. It does not court consumer attention. It powers the map you use when you’re trying to find the food court at an airport, and it does so quietly, reliably, for some of the largest physical venues in the world. That invisibility is almost the point.

From Three People to Global Infrastructure

Mappedin started, like most companies, as a small team with a clear problem and unclear path to revenue. Hongwei’s north star was simple: every building should be mapped indoors. The thesis has not changed. What changed, over a decade, was the shape of the market around it and the company’s ability to find where it fit.

That kind of commitment to a single problem is harder than it sounds. The table conversation surfaced a consistent pattern among the best founders: the ones who stop asking “what should I build next” and start asking “how do I actually solve this” tend to make faster progress. When the problem is the anchor, the tactical questions get easier. The ladder-climbing instinct, the trained reflex to always be optimizing for what comes next, is one of the things founders have to consciously unlearn.

The COVID Test

The most revealing story of the evening came from a period that should have broken the company. When COVID shut down every physical space Mappedin served, malls and airports and offices went dark overnight. By any reasonable model, customer churn should have followed.

It did not. Not a single customer canceled their contract. One asked for a credit. Everyone else said, essentially: the lights will come back on, and the maps need to be there when they do. That response told Hongwei something important about the nature of the product he had built and the relationships underneath it.

Then 2021 happened. The anticipated return to office triggered a wave of enterprise spending on hybrid workspace infrastructure. Room booking, hoteling setups, wayfinding for reconfigured floors. Mappedin was already positioned for exactly that. Growth surged from the same seeds planted before the shutdown. Hongwei’s framing: revenue is like a balloon. External pressure compresses some parts while others expand. The lucky breaks came from work already done.

The broader lesson for the room was about what customer relationships actually look like when they are real. Not a churn metric. Not a renewal rate. A customer saying: we’ll be here when this is over.

Who You Raise From Matters More Than How Much You Raise

The workshop and dinner both circled investor alignment, and Hongwei was candid about what it had cost him to learn it. His board jitsu, as he put it, is now sharp. It wasn’t always.

The core insight is structural: most angels are functionally private equity investors, whether they think of themselves that way or not. They want their money back with a return, at a timeline that roughly maps to PE IRR expectations. That is not the same as what venture capital wants, which is swings at outsized outcomes. And neither of those is the same as what a solo founder running a profitable business wants. Misalignment between a founder’s actual trajectory and an investor’s mental model of what they signed up for is one of the most reliable ways to end up with a difficult board dynamic.

His reflection looking back: by the time Mappedin reached three or four million in ARR, he would have raised less. Grown slower. Preserved more ownership. The angels he took on were betting on a path that did not quite match the one he was actually on, and the friction that created took years to work through.

The workshop covered the mechanics: how VC fund structures create incentives that are genuinely misaligned with good businesses that are not swinging for billion-dollar outcomes, why valuation caps at pre-seed have become disconnected from any underlying logic, and what back-channel diligence between investors and lawyers actually looks like in practice. This last point landed: the ecosystem is smaller than it appears, everyone talks, and that is mostly a feature rather than a bug. It keeps bad actors out as reliably as it surfaces good ones.

The Secondary Value Problem

Every founder who has scaled past a certain headcount encounters a version of the same problem. In the early days, everyone in the building understands that their job exists because of the primary value being created: the code, the sales, the customer relationships. That shared understanding is one of the things that makes small companies fast.

As a company grows, a tier of coordination and administration naturally emerges. That is not inherently bad. But the incentive structure that comes with it can quietly shift: roles that exist to support the builders can, over time, begin to optimize for their own complexity rather than for the output they were meant to enable. The farm is still there, but not everyone is thinking about the farm.

Hongwei has watched this play out at enough companies, and in enough forms, to recognize it early. The challenge is not the people. It is the incentives. And protecting the startup’s original clarity of purpose as headcount grows is one of the harder problems in company building, one that rarely gets discussed in early-stage circles because it feels like a problem for later.

It is not a problem for later. It is a decision you make early, by the culture you build and the things you make visible.

What the Hard Part Actually Is

One moment from the evening stood out as a fitting close. Early in Mappedin’s life, Hongwei expected a meeting with a well-known local CEO to be a celebration: recognition, encouragement, the kind of validation you imagine getting when someone prominent agrees to sit across from you.

It was not that. The CEO opened by talking about losing close friends to depression and suicide. About how genuinely difficult the founder path is. About wanting to sit with them and acknowledge that honestly, rather than paper over it with optimism.

Hongwei did not fully understand it at the time. Years later, he said, it made complete sense. The people who can actually help are not the ones who manage founders from a distance. They are the ones who have been through it, or who have watched people close to them go through it, and can tell the truth about what it costs.

That is also why rooms like this one at Builders Club matter.

Key Takeaways

Stay attached to the problem, not the path. Founders who anchor their identity to a specific problem rather than a specific solution or funding stage tend to make clearer decisions. The questions about what to build next, who to hire, whether to raise, get easier when the problem is fixed and the path is the variable.

Customer relationships are an asset class. Mappedin survived COVID because the product was genuinely embedded in its customers’ operations and the relationships reflected that. Retention under pressure is one of the clearest signals of real product-market fit.

Investor alignment is a structural problem, not a people problem. The conflict between a founder building a durable, profitable business and an investor who needs an outsized return to justify their fund math is not about bad intentions. It is about mismatched models. Understanding that structure before you raise is more useful than being surprised by it after.

The back channel is real and it works in your favor. Investors, lawyers, and advisors in a region know each other and talk. That social engineering is mostly protective. It keeps bad actors out of deals and signals good ones. Pretending it does not happen tends to be when things go wrong.

Slower can compound faster. Raising less and growing more deliberately preserves ownership and alignment. The founders Hongwei described as the happiest in the game were often the ones who had taken the least from outside the company and built the most deliberately over time.

The W26 Founder Dinner Series is hosted by Builders Club in Waterloo. Sessions run every two weeks through the winter term, pairing evening founder dinners with midday workshops. Thanks to our sponsors Osler and TD Innovation Partners for their continued support.

At Socratica this week, Krish Shah showed a room full of people how to turn a MacBook into a musical instrument.

Not by following a tutorial. By breaking down how the machine actually works — mapping sensors, understanding the hardware at a level most people never bother with — and then using all of it for something it was never designed to do. Something beautiful. Something that made people in that room think: I could do something like that.

That moment didn’t come from a classroom. It didn’t come from a curriculum. It came from curiosity that was given enough room to run.

That’s what Socratica is. And it’s worth paying attention to.

The above video features a student taking over everyone’s phones and all the sound and lights are from all the phones in the room.

What they built

Socratica is not even four years old. It started as a small group of students who wanted a different kind of gathering - one built around showing your work, sharing what you’re figuring out, being honest about where you are in the process. While making friends.

It has become something international. People fly in from San Francisco, New York, Boston, EU, Asia, etc to understand what this community is and why it feels like something real.

And when they took the stage this week, the students did something I found quietly remarkable: they acknowledged the campus. Upfront, genuinely. Not as a formality, as a truth. The campus gave them a place to find each other. It challenged them. It made what they’re doing possible.

That acknowledgment was generous and correct. But here’s the thing: the students own this. Every bit of it. Not the sponsors. Not the institution. The people who showed up, kept showing up, and built something worth flying across a continent to see.

The pattern we keep forgetting

If you trace the history of what Waterloo has produced - the companies, the products, the research, the movements - you find the same story over and over again.

Two people (or more) met in a dorm. A group figured something out together in a lab. Someone found their collaborator in a lecture hall, their first customer at a hackathon, their co-founder at a house party in the student village.

The university didn’t build those things. The people did. The university built the conditions - the density, the culture, the excuse to be in the same place at the same time - and then, crucially, got out of the way.

That’s the model. That’s always been the model. And somewhere along the way, institutions started forgetting it.

What universities are getting wrong

There’s a creeping instinct in institutions to own things. To lead causes. To take credit for outcomes they created the conditions for, not the outcomes themselves. To measure everything, approve everything, and thereby ensure that only the things they can already imagine are allowed to happen.

This is exactly backwards.

The magic of a great university has never been the lectures. It’s been the place. The campus as a container for free thought - where you can explore without judgment, say things that aren’t fully formed yet, be wrong in public, find the people who are working on adjacent problems, and figure out who you are and what you’re capable of.

That’s not something you can own. It’s something you have to protect.

Keep in mind, Socratica would not exist if they accepted the rules. They figured this out on their own.

One thing worth keeping

None of this means anything goes. Free thought isn’t the same as no standards.

The best communities - and Socratica is a good example - hold people to basic human decency while leaving everything else open. You can say what you think. You can challenge received wisdom. You can be weird, ambitious, half-baked, wildly wrong. But you treat people well. Full stop.

That’s not a contradiction. That’s the whole point. The freedom to explore only works when people feel safe enough to actually try.

The alumni advantage nobody is talking about

Waterloo has something most universities would kill for: a connected web of alumni on the bleeding edge of invention, scattered across the world, who still feel the pull of this place.

But right now, a lot of what binds us is a trauma bond. School was hard. The terms were brutal. We survived it together and that’s something, but it’s not enough to build on.

We should be proud to shape this institution, not just survive it.

The alumni are here. The talent is here. The goodwill is here. What’s needed is an invitation, a genuine one, to re-engage. To challenge the institution to think differently. To bring back the spirit that a room full of long-tenured staff and faculty quoted on the 40th anniversary when they put a George Bernard Shaw line on the wall about “why not?” It felt corny at the time. It was actually the whole point.

Find that again. Mean it this time.

What Waterloo could be

In the age of AI, what you’re being taught matters less and less. Access to information is everywhere. The ability to synthesize it, question it, build with it - that’s what’s scarce.

What’s going to be genuinely rare is a place where you can think freely. Where curiosity is treated as a virtue, not an inconvenience. Where the institution’s job is to create the conditions for discovery and then celebrate what emerges, without needing to own it.

Waterloo has been that place before. Co-op was a strange idea. A Red Room was a strange idea. Quantum computing was a strange idea. Mechatronics was a strange idea. They were all bets on the environment over the outcome.

Socratica is showing us what that looks like right now, in this moment, with this generation. Students discovering their ability. Finding the people they’ll build things with. Creating something that belongs entirely to them.

Build the campus that thrives in the AI world. Make it the place where free thought is protected, where curiosity compounds, where students find each other and make things that nobody could have predicted.

The alumni are watching. More than that, we’re ready to help shape it.

Come find us.

TLDR; Builders Club's physical space is where real trust and friendships form, but that the community's value doesn't stop when you leave the room. Nearly two years in, it has become something broader than a startup community — a diverse group of builders across consulting, hard tech, software, coaching, and more, all using AI to figure out what building looks like right now. The connections, intros, and knowledge sharing are already traveling beyond the space. The next step is making that more intentional so the community's value is accessible whether or not you're in the room on any given day.

We’re almost two years into Builders Club.

That’s long enough to see what it actually is, not just what we hoped it would be.

What I’ve seen is harder to describe than I expected.

We are on the leading edge of something. Not just building startups, building everything. Consulting practices, side projects, software products, coaching businesses, marketing operations, hard tech. Members are using AI to move faster, figure out new models, and do things that weren’t practical twelve months ago.

What makes that interesting isn’t the technology. It’s the room it’s happening in.

Because when a hard tech founder and a consultant and someone building a coaching practice are all wrestling with the same tool at the same time, the conversation gets weird and useful in ways that a single-category community never produces. Different problems. Different constraints. Different instincts. All pointed at the same moment.

That diversity isn’t incidental. It’s the thing.

What the Room Does

There’s something that happens in the physical space that I haven’t figured out how to manufacture anywhere else.

Someone mentions a problem offhand, pricing, a technical decision, a customer conversation that went sideways, and three people turn their chairs. Not because it’s a scheduled discussion. Because they’ve been in that exact situation and they have something real to say.

Friendships form. Patterns develop. You start to recognize how someone thinks before they’ve finished their sentence. That’s not a Slack channel thing. That’s a Tuesday afternoon, same room, same coffee, three weeks in a row thing.

The physical space is where trust gets made. It doesn’t come from a shared channel or a monthly call. It comes from proximity, repetition, and the small moments that don’t make it into anyone’s content calendar.

That part can’t be replaced. We’re not trying to replace it.

But Trust Shouldn’t Stop at the Door

Here’s the thing about the connections that form inside that room.

They don’t stay inside that room.

An intro happens on a Wednesday afternoon in person. A week later it turns into a customer conversation in San Francisco. Someone shares what they’ve learned deploying a new model, not in a talk, not in a post, in a message to three people who needed to hear exactly that. A member who moved to Toronto six months ago is still one of the most active people in the community.

The value travels. The trust travels. What we’ve built in the physical space has started to compound outside of it.

That’s not surprising. It’s the whole point.

What We Haven’t Fully Solved

An active Slack and a good room will take you a long way.

They haven’t taken us all the way.

There are members who want to be connected but can’t always be present. There are introductions that should happen but don’t because nobody facilitated them. There’s knowledge inside this community, real, hard-won, current knowledge about building in the age of AI, that isn’t reaching the people who need it most.

The informal version of Builders Club has been better than most communities ever get. The next version needs to be something more. Not more structured for its own sake. More intentional about making sure the community’s value isn’t gated by whether you were in the room on the right day.

We’re working on that.

Who This Community Actually Is

Not just founders. Not just Waterloo.

Some of our most connected members don’t live here full time. Some are deep inside companies, building things that matter, not in startup mode but in builder mode. Some are consulting, some are growing practices, some are figuring out what’s next.

What they share is a preference for being around people who are serious. Not performative, not networky, not playing startup. Actually trying to level up and willing to do it out loud.

That’s who this community is. And that person exists in more places than one building in Waterloo.

What Comes Next

We are building companies in the age of AI. Nobody has done this before. The playbooks are thin and the tools are changing faster than the frameworks for using them.

What we have inside Builders Club is a group of people figuring this out in real time. Sharing what’s working, applying techniques before anyone has decided they’re best practices, challenging each other’s assumptions before the assumptions cost them.

That’s rare. And it shouldn’t only be available to whoever showed up in person this week.

The physical space will always be the anchor. But the network is the asset.

We’re figuring out how to make sure more people can feel that, wherever they are.

And if you’re reading this because you’re looking for exactly this kind of community, people who are serious about building, who are using AI across every kind of work, who will give you an honest answer instead of a polished one, we’re here.

Not every question has a home. But a lot of them do.

Reach out (link to book a meeting is on the website). Come see what’s happening.

Jesse Rodgers is the founder of Builders Club, Waterloo’s community for serious builders, and Barn Ventures, an early-stage fund backing people before the rest of the market notices them.

TLDR: Centralized systems build qualifications, formal ones and social ones. The social ones do the most damage. They select for compliance, legibility, and the pattern of what a builder looked like last cycle. The builders worth finding don’t fit that pattern yet. The ecosystems that compound aren’t the most organized ones. They’re the ones that kept a door unlocked.

There’s a version of ecosystem building that feels responsible.

You create structure. You set standards. You design a room with clear criteria for who belongs in it, what stage they need to be at, what they should be able to show.

Something that can be managed, measured, reported on.

And in a lot of ways, it works. Just not for the people you actually want.

The qualifications nobody posts

Every centralized system builds qualifications. Usually the formal ones get written down - stage, revenue, team size, sector.

The ones that do the most damage are the social ones.

Have you been seen at the right events? Do you know the right people? Can you speak the language of the room - the vocabulary of traction, the grammar of a well-structured pitch? Do you fit the pattern of what this community has decided a builder looks like?

That’s a different gate than it sounds. And it’s not malicious. It’s just what happens when a system optimizes for legibility.

Legibility requires pattern-matching. Pattern-matching, over time, closes the room to anything genuinely new.

The person building something nobody has a category for yet doesn’t pass that filter. Not because they’re not serious. Because seriousness, at that stage, looks indistinguishable from confusion.

What YC actually does

People misread YC constantly.

The common read: it’s a program. Apply, get in, do the program, raise money.

The honest read: it’s a very specific filter for a very specific moment. They’re looking for a particular type of person at a particular point in their trajectory - someone ready to move hard in the next 12 weeks, who will have something significant to show for it. They scour the world for enough people to fill a batch. And even then they get it wrong sometimes.

What they’re not doing is organizing builders generally. They don’t put effort into the places the builders come from. They care about filling their batches with the right people.

The problem isn’t YC. The problem is when every local version of support tries to replicate the structure of YC without the filter and ends up with something too broad to be selective and too centralized to be porous.

You get a room with gates but no real criteria. And the gates end up being social.

What compliance selects for

Here’s what happens when control tightens: the people who stay are the ones willing to comply.

Compliance selects for patience. For social fluency. For the ability to explain yourself in the expected format, to wait for the right moment, to modulate your ambition to fit the room.

Those are real skills. They’re just not builder skills.

The builders who won’t comply don’t disappear. They find a room with an unlocked door. They leave for San Francisco, or they start in a basement, or they show up to some low-production event with no formal criteria and try the thing out in front of whoever happens to be there.

And some of them are building a Tailscale. And nobody in the organized room knows.

Avery Pennarun demoed something at StartupCampWaterloo that was so early, so unpolished, nobody could have told you what it would become. PagerDuty was in a room like that too - product already real, already working - and you still couldn’t have imagined the scale they would achieve. No one handed them a grant. No one vetted them. The room had no qualifications. It just had an unlocked door and enough people willing to show up and share something half-formed.

That’s not a model you can institutionalize. But it is a condition you can either protect or destroy.

What institutions can’t do

Institutions are good at keeping things calm. Consistent. Accountable.

Those are real virtues. The problem isn’t that they have them. It’s that they’re structurally incompatible with what early builders actually need.

Early builders need to try things without having to explain too much. They need to fail in front of people who won’t use it against them. They need to be around others who are also in the middle of something uncertain, so the uncertainty feels normal rather than disqualifying.

That environment has a texture. It’s a little messy. Low-production. It has overlap and friction and half-baked ideas that take up airtime they haven’t earned yet. From the outside, it doesn’t look like much is happening.

From the inside, it’s where everything starts.

Universities used to do this - not intentionally, but structurally. The labs were open. The doors were unlocked. You could try things without approval because there weren’t enough resources to police everything. That’s not a design philosophy. It’s an accident of under-resourcing that turned out to be generative.

When you add resources, you add oversight. When you add oversight, you add qualifications.

And the unlocked door quietly closes.

What you’re actually looking for

The builders most worth finding don’t look like builders yet.

They look like edge cases. People who showed up without quite fitting the profile. Working on something they can’t fully describe, for a customer they haven’t found yet, with conviction that seems disproportionate to what they can show you.

That’s what early looks like.

An organized room - calibrated to legibility, to social qualification, to the expected pattern - will miss them almost every time. Not because it’s hostile. Because it’s not designed for this moment. It’s designed for the moment after, when things are starting to make sense, when you can point at traction, when the pitch has gotten clean.

By then, the most interesting part is already over.

The ecosystems that compound aren’t the most organized ones. They’re the ones that kept a door unlocked long enough for the next thing to walk through before anyone knew what it was.

That’s harder to build than a program. Harder to measure. Harder to report on.

But it’s the only part that actually matters.

Builders Club is where serious builders in Waterloo gather - not a program, not an institution, just a room with an unlocked door (if you buzz up). Barn Ventures backs them before it’s obvious.

TL;DR: Brad Murray joined us for Week 4 of the W26 Founder Dinner Series. His career arc, from Pebble’s fourth employee building a smartwatch OS from scratch, to co-founding Beeper and navigating a high-profile fight with Apple, to landing at Automattic as Head of Engineering for Beeper, is a masterclass in staying technical, staying curious, and staying local. The evening’s conversation touched on what it’s really like to build hardware before there was a playbook, how to manage remote teams without losing alignment, why async communication requires intentional design, and what it means to raise money and build a company in a market that changed dramatically between your first and second rounds.

Week 4 brought a different kind of energy to the table. Where earlier dinners featured founders and investors who could point to clear product-market fit and venture-scale outcomes, Brad Murray offered something just as valuable: an honest, unfiltered view of what it’s like to be the person actually building the thing. The one writing the OS, debugging the hardware, keeping the ship running.

Brad is Head of Engineering at Beeper, now part of Automattic, the company behind WordPress. He co-founded Beeper with Eric Migicovsky, and before that was employee number four at Pebble, arguably the company that put the smartwatch category on the map before Apple showed up and redefined it overnight.

He never left Waterloo. That fact alone says something.

The Pebble Story: Building the First Smartwatch

Most founders in the room knew the name Pebble. Fewer knew what it actually took to build it.

Brad joined as one of the first engineers in 2012, shortly after the Kickstarter campaign that raised $10 million, at the time the largest crowdfunding campaign ever run. The product was a watch that paired with your phone, showed notifications, and ran apps. That sounds obvious now. In 2012, it wasn’t.

“I would call it the first smartwatch, basically,” Brad said. “There were weird Casio things before it, but Pebble was the first popular one.”

The team had to build everything from scratch: the OS, the SDK, the developer ecosystem, all of it. They sold over a million devices. They ran three Kickstarter campaigns, the largest of which raised $20 million. They were, by any measure, doing something that mattered.

Then the Apple Watch arrived in 2015. Things got hard fast.

Pebble sold in 2016. The outcome was mixed: a real company, real users, real technology, but ultimately unable to compete with a hardware giant that had decided the market was worth owning. What’s interesting is what came out of it. The underlying frustration that drove Pebble’s co-founder Eric Migicovsky (why can’t developers get API access to text messages? why are platforms locking this down?) never went away. It eventually became the seed of Beeper.

Beeper: Taking on Apple (Again)

Beeper started with a simple premise: messaging is personal, and it should work across every platform. iMessage, WhatsApp, Signal, Telegram, SMS, one app, all of them. The technical challenges were enormous, and the business model challenges were arguably bigger.

Brad and Eric started the company remotely during 2021, a moment when raising money felt very different than it does now. “We were able to start a company during the good old days of 2021 where raising money was actually decent,” Brad noted. They raised a single significant round, a “monster” by his description, coming out of Y Combinator, and rode that runway for two to three years.

By 2023, the fundraising market had changed entirely. The metrics investors wanted had shifted. The story that worked in 2021 (DAUs matter, monetization comes later) didn’t land the same way. “Cash flow became king,” Brad said simply.

What followed was a high-profile battle with Apple over iMessage access that played out very publicly. The tension between building a product that depends on platform APIs and the platform’s willingness to honor that access is a structural problem for many founders. Beeper experienced the most visible version of it.

Automattic ultimately acquired Beeper. It turned out okay. But the journey from initial raise to acquisition was a clear illustration of how dramatically the funding environment can shift mid-company, and why founders who aren’t thinking about what it takes to stay alive can find themselves in serious trouble.

Workshop: Default Dead or Alive?

The evening was paired with a workshop focused on Paul Graham’s “Default Dead or Alive?” framework, and the timing felt right. Brad’s Beeper story is, in part, a story about runway, about what it costs to stay alive, and about what happens when the external environment changes the rules of the game while you’re in it.

The core concept isn’t complicated: a company is either on a path to profitability before it runs out of money, or it isn’t. Default alive means your growth trajectory gets you to breakeven before the runway ends. Default dead means it doesn’t, and you need either a new plan or new capital.

The nuance is that most early-stage founders don’t spend enough time thinking about this clearly. The temptation is to focus on product, on traction, on metrics that feel like progress without asking the harder question: what does it actually cost to be alive, and how do I get there?

As the workshop framed it: running out of money is what kills 100% of companies. The game isn’t valuation; it’s staying alive long enough to get lucky. And getting lucky requires a realistic picture of the math.

Brad’s story illustrated the point in both directions. Beeper had significant runway from their initial raise, which gave them time to build and iterate. But when they went back to market in 2023 and investors had changed what they were optimizing for, the company had to reckon seriously with what it would take to survive in a tougher environment. That’s not a failure of execution. It’s the reality of building a company across multiple market cycles.

Remote Teams: The Alignment Problem

One of the most practical conversations of the evening was about remote work, fitting given that Brad has been building remote-first teams since 2012, when the tooling barely existed and the concept was still experimental.

His perspective wasn’t that remote is bad. It was more specific than that: remote and async are not the same thing, and conflating them creates problems.

When Pebble scaled quickly after the Kickstarter, Brad and a colleague set up what was effectively a remote outpost in Waterloo while the core team operated elsewhere. The tools were primitive: Skype, early video conferencing, whatever worked. They made it work.

With Beeper, the team was distributed across multiple time zones, including engineers in Finland. The practical reality was that 11 AM Eastern was 6 PM in Helsinki. Someone always loses when you’re spread that far. “You just have to be straight with people,” Brad said. “Here are the four hours we must be online. If those hours don’t work for you, this isn’t the right company for you.”

But the deeper insight was about what remote removes without anyone noticing: the constant, ambient nudging back into alignment that happens when people share a physical space. In an office, you absorb what’s working and what isn’t through a hundred small interactions. You overhear what’s getting traction. You sense when something’s off.

Remove that, and people drift. Not maliciously, just gradually, quietly, in small ways that compound. Brad described a period about nine months into Beeper when the team was around eight to ten people and something wasn’t clicking. “We kind of had this come-to-Jesus moment where we thought, did we hire idiots? What’s going on?” The people were smart. The problem was structural. Without constant realignment, teams working on hard, ambiguous problems naturally diverge.

His solution wasn’t to mandate more meetings. It was to get serious about written communication as a primary tool for building shared context.

The Case for Writing

If there was one piece of tactical advice that landed hardest, it was this: learn to write.

Not journaling. Not documentation for its own sake. The specific discipline of writing out your thinking, your proposal, your reasoning, your tradeoffs, and giving people time to engage with it before responding.

“I write a lot of RFP-type things,” Brad explained. “Here’s a change I’m thinking about making. Here’s why it’s a good idea. Here are the tradeoffs I considered.” He puts it in Notion, links it in Slack, and lets it collect comments for a day before the live discussion.

The contrast is with how most decisions get made in chat: someone asks a question, a few people react quickly, the context collapses immediately, and when you look at it later it’s nearly impossible to reconstruct what problem you were actually trying to solve.

Writing forces clarity. It gives people time to think rather than just react. It creates a record. And for distributed teams operating across time zones, it’s often the only way to have real conversations about important decisions, since not every conversation will happen live.

This is a skill, Brad noted, not a natural instinct. Most people are better at talking than writing. Building companies that default to writing requires deliberate effort, especially at the beginning when it feels slower than just getting on a call.

On Staying in Waterloo

Brad has been in the Waterloo ecosystem for his entire career: Pebble, Beeper, and now Automattic. He’s watched cohorts of founders move through, some to San Francisco, some staying local, most doing a version of both. He chose to stay.

There’s something worth noticing in that. The dinner format, small group, honest conversation, founders at different stages in the same room, is exactly the kind of community infrastructure that makes it possible to build in Waterloo rather than feeling like you have to leave to be taken seriously. Brad’s presence was a reminder that the builders who stay are part of what makes that possible for the next generation.

Key Takeaways

The evening crystallized several ideas worth carrying forward:

Running out of money is the only cause of death that’s 100% consistent. Everything else, bad product, bad market, bad timing, can be survived or pivoted through. No runway can’t. Founders who don’t develop a clear picture of what it costs to be alive are operating on borrowed time.

Remote work doesn’t solve the alignment problem; it relocates it. Distributed teams lose the ambient alignment that happens in shared spaces. The answer isn’t more meetings. It’s intentional written communication that creates shared context and gives people time to think.

Write more than you think you need to. The discipline of writing out your reasoning, proposals, decisions, tradeoffs, before discussing them live is a superpower for distributed teams and a forcing function for clearer thinking generally.

Fundraising markets change faster than product cycles. Beeper raised in 2021 and tried to raise again in 2023. Those were completely different conversations. Founders who build assuming the market will look the same in two years are making a bet they may not have intended to make.

Staying technical is a competitive advantage. Brad has been writing code across every company he’s worked on. That foundation, understanding how things actually work, doesn’t disappear when you scale into leadership. It informs every decision.

The W26 Founder Dinner Series is hosted by Builders Club in Waterloo. Sessions run every two weeks through the winter term, pairing evening founder dinners with midday workshops. Thanks to our sponsors Osler and TD Innovation Partners for their continued support.