From Ottawa to YC: How My Friends Turned a $5K Gamble Into a Y Combinator Acceptance
By Hai Nghiem
Josh was on a bus in Russian Hill when his phone buzzed. The name on the email made him do a double take: Garry Tan.
It was 5:55 PM. The email said to meet at 6:00 PM. Across town.
He yanked the cord, jumped off the bus, and called an Uber to Dog Patch. It was their second-to-last day in San Francisco. They had almost nothing to show for 30 days of pitching. And now the CEO of Y Combinator wanted to meet.
I've known Josh and Leo for a while now. They were members of our AI Tinkerers Ottawa community (now AGI Ventures Canada) before any of this happened. We talk every week about what we're going through in our own business journeys. I watched this whole story unfold in real time.
Nine Months of Nothing
Before that bus ride, Josh and his two co-founders had been grinding in Ottawa for nine months. They were cooped up in their apartments, building something in the AI contracts space. Nothing was working.
They had a product. They had conviction. What they didn't have was traction, customers, or any sign that the market cared.
Then they won $5,000 in a pitch competition. It wasn't life-changing money. But it was enough to ask a dangerous question: What if we just go to San Francisco and see what happens?
They didn't have a plan. They had a hypothesis. If they could get in front of enough people, something might click. In Ottawa, the opportunities felt limited. In San Francisco, they'd heard stories of founders getting lucky breaks just by showing up.
So they booked flights, signed up for every event they could find, and emailed investors with vague promises about maybe raising a round. It was part hustle, part desperation.
Thirty Days of Pitching
For the next month, all three co-founders pitched. Everyone pitched. The CTO pitched. They'd show up to events with laptops open, shoving their product in people's faces. "Do you think this is cool? Would you pay for this?"
Most conversations went nowhere. The idea wasn't landing. They were burning through their limited funds with little to show for it.
But they kept going. Every single day for 30 days.
Near the end of the trip, they reached out to someone they'd met online months earlier. He'd been working on LLM testing, they'd collaborated a bit, and he'd since joined a new company and gotten into YC. They figured they'd finally meet in person.
Over lunch, he mentioned something offhand: there was a YC dinner coming up. He could only bring one person. Did they want to come?
For founders who'd been dreaming about YC from afar, this was surreal. They decided Josh would go. Leo, who had originally made the connection, stepped aside. Then they waited.
Days passed. No confirmation. On their second-to-last day in San Francisco, sitting on that bus in Russian Hill, Josh had mostly given up on the dinner happening.
Then Garry Tan's email arrived.
The YC Dinner
Josh made it to YC headquarters with minutes to spare. He didn't actually meet Garry. The email turned out to be automated. But he made it inside.
The energy was unlike anything he'd experienced. Long tables, food and drinks everywhere, founders swapping stories. He described it to me like Hogwarts. The CEO of DoorDash gave a talk about his background.
But Josh wasn't there to spectate. He was there to pitch.
After the talk, he found David Lieb. David had founded Bump, the app where you'd bump phones together to share photos. That technology eventually became Google Photos. He'd seen everything.
Josh pitched him anyway. Laid out the whole vision, everything they'd been building.
David's response was short: "Hm, that's pretty interesting. I've never heard that before."
From someone who'd seen thousands of pitches, that was enough. Josh got his email and promised to stay in touch.
The Crash
They flew back to Ottawa with one new connection and not much else. No LOIs. No committed investors. No clear path forward.
The energy shifted fast. Their third co-founder grew distant. A few weeks later, he came to Josh directly: he didn't see it anymore. They'd been at this for over a year. The SF trip hadn't delivered. He was stepping back.
It was hard. They'd built this vision together. When someone tells you they don't believe in it anymore, it stings.
But they ended things cleanly. No bad blood. That would matter later.
Now it was just Josh and Leo. Limited funds. No traction. A YC application they'd submitted weeks ago with no response.
They figured they weren't getting in.
The Callback
A week after their co-founder left, another email arrived. Same Garry Tan name in the sender field. This time it was real: YC wanted to interview them.
The timing was brutal. They'd applied as a team of three. Now they were two. Things weren't looking great.
The interview was scheduled for two days later. Ten minutes. That's all you get.
When they joined the Zoom, Garry Tan was sitting there. Not David Lieb, who Josh had met. Garry himself.
They answered everything as best they could. What are you building? How does it work? How will people adopt it?
Ten minutes flew by. Then came the follow-up requests.
First, YC wanted all their recent Git commits. Probably because they'd mentioned losing a co-founder. They wanted proof of work.
Then Eric Levine, a visiting group partner, asked to speak with the ex-co-founder directly.
Josh had to make an awkward call: "I know you left the company a week ago, but YC wants to talk to you."
Because they'd ended things well, his former co-founder said yes. No hard feelings.
Six hours of waiting followed. Josh and Leo sat at their desks in Ottawa, refreshing their inboxes, wondering if this was really happening.
Then the phone rang. San Francisco number.
Garry was on the line. "Hey guys, it was great. Thank you for providing all the information. I want you to be a part of this program."
After a year of taking Ls, they were in.
The Batch
Once in San Francisco for the batch, Josh and Leo went heads down. Sixteen-hour days. No events. No networking. Just building and talking to customers.
I remember Leo telling me his plan was to DoorDash every meal so he wouldn't have to cook. Just code all day. That didn't last long.
Leo posted on LinkedIn that they weren't going to any more events. They were there to grind. The YC community pushed back. You're missing the experience. You should be meeting people.
They had to take the post down. In retrospect, Josh thinks the community was right. YC is short. Two and a half months. The founders around you might be building the next unicorn. You should probably get to know them.
But they were focused on survival. They vibe-coded prototypes in V0 and Cursor, turning them around in 24 hours when enterprises asked for something specific. I remember Josh showing me different versions of the product over our calls. They pivoted from procurement contracts to legal contracts to deal desk. They built a community from scratch for deal desk professionals because no resources existed. Heads of deal desk from Stripe and Airbnb joined. The community gave them insights that shaped their product.
Today, Outlit is an AI workspace for custom sales proposals. The path there was anything but straight.
What Canadian Founders Should Know
Josh tried raising from Canadian investors before any of this. The conversations were tough. How much revenue do you have? How many customers? The expectations for early-stage founders felt unrealistic.
In the US, investors take bets on ideas and people. In Canada, the risk appetite isn't there.
This is why Canadian founders leave. They go to San Francisco, get into programs like YC, incorporate in Delaware, and never look back. Canada loses these companies entirely.
Josh's advice for founders still in Canada: branch out. You don't have to move immediately. Build connections online first. Reach out to people in San Francisco. Validate what you're building remotely. Then, when you're ready, take the risk.
Because that's what this game requires. Josh and Leo took their last $5,000 and flew to a city where they knew almost no one. They pitched for 30 days with almost nothing to show for it. They lost a co-founder. They waited six hours for a phone call that could have gone either way.
The YC acceptance didn't come from a perfect application. It came from one lunch, one dinner invitation, one pitch to a guy who'd seen everything, and the willingness to show up when showing up was all they had left.
Sometimes the only path forward is through.