Will Gaybrick explains that startups have higher quality standards than enterprises because they're accustomed to modern tools, which forces Stripe to build better products that then serve Fortune 500 companies. ✦ AI generated
Will Gaybrick · a16z Podcast · 2026-08-17 · original ↗
starts at this moment · 5:49
“How do you think about the product strategy as it relates to serving startups versus serving large enterprises?”
Stripe strategy is unabashed, I'm paraphrasing his words, but it's win all the startups and then win them again. Startups are very ambitious. They typically grow into the biggest companies of tomorrow. They're sort of canaries for what the next opportunity is. They actually have the highest standards of all of our customers. For our very very large enterprise users, your reporting is great, we love the data. For startups: your reporting is garbage, you have got to fix this, this is driving me crazy. And so there's this persistent sense that startups just make us better by being the fastest, by being most demanding.
verbatim transcript · starts at 5:49
5:49strategy as it relates to serving startups versus serving large enterprises? >> So, I think it was actually um Colin at Clerk who who summarized our strategy nicely on on X recently where he said stripe strategy is unabashed. I'm paraphrasing his words, but it's win all the startups and then win them again. >> Yes. Um and I think you know to some extent that's just a good business model
6:14because startups are um very ambitious. They typically grow into the biggest companies of tomorrow. They're sort of canaries for what the next opportunity is. So on another subtle reason to win all the startups and win them again is they actually have the highest standards of all of our customers. uh you know I I looked recently at uh the seesap for stripes reporting and for our very very
6:38large enterprise users like your reporting is great like we love the data you go it's way better than anything we get from any of our other >> because they're accustomed to the incumbents. Yeah, exactly. And then you you look at it for startups like your reporting is garbage. You have got to fix this. This is driving me crazy. And so there's um this persistent sense that startups just make us better by being
6:57the fastest, by being most demanding and so on. But of course once we start working with startups, we want to work with them forever. And so this pulls us up market and you know forces us to become you know as sort of surprisingly great. That's the standard we try to hold ourselves to for enterprises as for startups. And now we're working with I don't know what the exact percentage is
7:17today but it's not quite half but we're getting there. Uh Fortune 500 companies you know we work of course with the Amazons of the world um Microsofts and you know at the enterprise it's sort of a different sales cycle. It's a different uh you know post sale activation motion. It's a lot more required you know after you've already signed the contract whereas startups sort of go live like that. But