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At our YC Winter feedback session, Canadian YC alumni Raghav Midha (S23), 🤖 Danilo Cabello (W22), Jason Goldlist (W22), Daniel Baum (W21), and William Ma, CFA (S18), went through real YC applications line by line with founders in the room.
Their advice was specific, and most of it can be applied to your own application in an afternoon
Find and fix the small gaps
A reviewer comparing two applications will usually pick the one with fewer open questions. The alumni pointed to small details that cost founders more than they realise.
No website. You can build a basic one in an afternoon, and leaving the field blank makes the application look unfinished.
A vague co-founder answer. If you’re solo, show how you’re searching. If you aren’t looking, say so and explain why.
Grants listed as “investment.” Government funding doesn’t count. If you’re unsure whether you’ve taken investment, you probably haven’t.
Overthinking “incorporated?” If you haven’t incorporated yet, say no. It doesn’t make you any less of a founder.
Assuming the reviewer knows your industry. Partners won’t know it, and nobody expects them to. One plain line about why the problem hurts your customer sets up everything that follows.
Say what you don't know, then show how you'd find out
This came up more than once.
Founders feel pressure to sound certain, especially about market size, and it's tempting to borrow a trillion-dollar figure from a research report. The alumni said anything made up doesn't belong in your application. YC is betting on you, and they want to see how you think when the data isn’t there.
Their advice was to build your market size from the ground up. One alum's team counted the vehicles in America and multiplied that by what they could charge per vehicle each year. Math like that shows you understand how you'd actually make money. If the number comes out small, that's a signal to think about where the business goes next.
A $60M-a-year company is a great business, but YC "won't get out of bed" for it. For the bigger vision, start with "we believe" and follow it with something you genuinely believe.
As one alum put it, if you think you know all the answers, that's bad news for you.
Make your traction easy to picture
Traction claims are easy to skim past. A few small rewrites make your progress feel real.
Instead of | Try |
|---|---|
"We think customers need this." | "We heard from 10 customers that this costs them [X]." |
"We've made strong progress." | One line per month on what you shipped, sold, or learned. |
"We have early users." | Who they are, how they found you, and what problem brought them in. |
The month-by-month format came from one alum's own application. It made their team's speed easy to see, and speed is one of the main things YC looks for.
Give the questions about you as much care as the business ones
Most applicants pour their time into the business questions and rush the ones about themselves. One alum said their team spent 90% of its effort on the business side and called it a trap. Another said around 15% of their batch was accepted with no idea at all, because YC knows companies pivot and is really backing the founder.
The alumni said partners read your personal answers for a few signals, so make each one easy to find.
Tenacity. Share times you competed, pushed through, or found a way around a closed door.
Why you left the safer path. Say why you chose to build this instead of staying where you were.
How you communicate. Your founder video shows whether you could stand on stage at Demo Day and close a round.
Humility. Making it clear you’re still learning from your customers builds trust.
Bring the same approach to any investor room
Pitching an investor means asking someone to take a bet on very little information.
Being clear about what you've done, honest about what you don't know, and specific about how you'll figure it out makes that bet easier to take.
If you're working on your application, go through it section by section with this edition open. And if you land an interview, let us know so we can help you prepare.
Which part of your application or pitch is hardest to get right?
👀 A Packed Room of Canadian Founders in SF
Last night, 100+ Canadian founders and investors got together in San Francisco during SF Tech Week.
Some were visiting, some have lived in the Bay for years, and some are mid-move. All of them came to meet other Canadian founders, and almost all plan to build in both places, pairing Silicon Valley’s pace and connections with the talent back home.
That came through on the panel too, where AngelList CEO Avlok Kohli, Boardy creator and Clearco co-founder Andrew D’Souza, and Quo co-founder Daryna Kulya shared what they’ve learned building across both.
📣 Get your product in front of 200+ founders, operators, and investors
We're looking for F&B and CPG brands to set up booths at Commerce Toronto on Oct 13 and partner with us on future events.
At past events, @waterballoonco, @brodohouse, @go_kunana, @nutes.nutrition, @greenbowleatsalad, and @rawcology sampled and sold their products to hundreds of attendees.
Sample your products, sell on the spot, collect live feedback, and walk away with new leads and connections. Reach out to [email protected] to get your brand in the room.
📆 TechTO upcoming events
Oct 15 - Peerscale Quarterly Dinner: A private dinner for Canada's fastest-growing tech founders and executives (CEOs, COOs, CTOs & CFOs) of companies over $2M ARR. Learn more at peerscale.com. To request a spot, email [email protected].
Planning to attend TechExit.io Toronto? Get 20% off with code TECHTO-20, or reply to this email for a bigger discount.
Oct 17 - TechTO Fast and Frugal Hackathon (Toronto): Build an AI Agent that finds and books the best hotel deal in any city in 12 hours. The fastest and cheapest booking wins cash prizes and cloud credits.
Oct 20 - TechTO Montreal Rocketships Soirée: An invite-only evening with builders and investors in Quebec with a spotlight on eight fastest-growing companies. Know a company that should be on the list? Nominate here!
Nov 3–5 - TechTO x SAAS North AI 2026 (Ottawa): Join 2,500+ SaaS founders and operators building the future of AI. Get your all-access pass through TechTO for nearly 40% less than the online price.
📣 Announcements
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Have a question you’ve been wanting to find an answer to? Type it in at AskTechTO and get answers from 1,500+ founder talks on TechTO’s stage across industries, growth and funding stages.
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