Gabriel Jarrosson has invested over $40M in more than 100 Y Combinator startups. But before becoming a VC, he was a founder — scaling seven companies (some to exit) and bootstrapping to $1M ARR with zero employees.
In this episode, Gabriel joins Richard Lee to talk about what founders really need to know before raising capital. It’s a candid, practical conversation that cuts through the hype around venture funding and digs into what actually builds resilience and power in a startup.
We cover:
Why the best time to raise is when you don’t need the money
The personal risk most founders ignore — and how to de-risk without selling out
The emotional cost of staying too long in a business that’s “doing okay”
What makes a pitch deck land (and what turns investors off)
One AI startup that blew Gabriel away — and what it teaches us about product-market fit
This one is packed with founder truth bombs, hard-won lessons, and a refreshing perspective on growth without giving it all away.
