Why I started YIP, and what I got wrong in year one

I started YIP because I kept having the same conversation with different founders, talented, hardworking people stuck not because their idea was bad, but because nobody had ever shown them the actual mechanics of building a company. Not inspiration. Mechanics. How a term sheet actually works, how to run a customer interview that isn't a leading question in disguise, how to know when a rebrand instinct is real or just month-three doubt.

What year one got right

We got the mentor model right early, pairing founders with people who'd actually done the specific thing they were stuck on, not generalist advisors giving generic advice. That decision is still the backbone of every cohort we run, and it's the one piece of the original plan I wouldn't change.

What I got wrong

I underestimated how much founders needed each other, not just mentors. Cohort 01 was structured almost entirely around one-to-one mentorship, and the founders who struggled most were the ones with no peer accountability, nobody checking in on a Tuesday just because they were in it together. We rebuilt the entire community and classroom structure around that gap by Cohort 02, and it's made a bigger difference than any single piece of curriculum content.

“Mentorship gets founders unstuck on a specific problem. Community is what gets them to show up the following week when nothing's unstuck yet.”

Four cohorts in, the thing I'm proudest of isn't a growth number. It's how many founders from Cohort 01 are still in the community chat, still answering the newer cohorts' questions, entirely unprompted. That wasn't in the original plan. It's the part of year one I'd take credit for the least and value the most.