Sheldon McCormick on Always Having a Move: Taxi Lines, Two-Miracle Businesses, and the Ending Nobody Plans For
Third Founder Dinner for S26: Launched uberX in Toronto. Co-founded Properly. Now leads Communitech.
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.