Patrick Collison on the Culture of Stripe and How to Hire [The Knowledge Project Ep. #32]

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I was fortunate enough to sit down with FS reader and Stripe CEO Patrick Collison. In our two hour conversation we talk about the biggest mistakes he made in the early days, how he scaled stripe from 2 to over 1,000 employees today, why he values velocity over correctness, his unique approach to reading and so much more. In the powerful excerpt below, Patrick explores the culture of stripe and what he’s looking for when hiring.

You can find full audio, show notes, and a pdf of the entire transcript here.

How would you describe the culture at Stripe? What do you actively try to achieve with that?

I’ll answer that with a caveat, and the caveat is that I’m pretty sure the answer I would have given to this would have differed in some material ways two or three years ago. That’s in part because I think we’re coming to realize things that we just hadn’t really appreciated or seen the significance of two or three years ago. Also, in part, because literally what it is that we need today is just different from what we needed two or three years ago. And so I think there’s a double contingency in the answer, where it’s a function of just what we’ve realized at this point, but also what it is that the organization and the company needs and the challenges that we currently face.

With that caveat, I think there are a few things that we really prize and try to seek in the people we hire. First, a kind of rigor and clarity of thought. So many organizations prize smoothness, smoothness in interactions and trying to reduce or minimize the number of ruffled feathers. And they at least inadvertently, if not deliberately, prefer cohesion over correctness, and we really try to identify people who are seeking correctness and who don’t mind being wrong and who are willing to at least contemplate things that seem improbable or surprising if true or really divergent [from] that which is the generally accepted status quo.

And that’s hard to find. I don’t think most of the educational institutions that we all tend to have attended do a great job of teaching that. We look for that combination of openness and rigor.

Next,I don’t exactly know what the right word is, but a determination and competitiveness, and I guess willfulness, in that … just doing anything of significance is hard. Anyone who’s tried to do anything that they themselves considered significant knows that very viscerally. And especially for a startup, the default outcome is your relatively near-term non-existence.

The default outcome is that you do not survive; and to survive over the medium or, even with more difficulty, over the long term, that is like an unnatural act. And so you need to find people who not just are willing to push against the expected trajectory of non-existence, but people who actually enjoy that, who want that. Because if they’re merely willing to do it but they don’t actually enjoy it, then the work is probably going to be less fulfilling for them over the medium term.

And I really don’t think that is for everyone and I don’t think that’s a bad thing. The cliché, of course, is that startups are extraordinarily hard, and they just are. You want somebody who is at a stage in their life where that’s the kind of challenge they want, where the fact that the particular area in which they’re going to be working is undefined or significantly under-built-out or significantly broken or whatever the case might be, that that’s what they’re looking for.

And then we try to find people who just have — again, to return to these words — interpersonal warmth and a desire to make others around them better and just a degree of caring for others and a desire to be, nice is kind of an anodyne word, but to be nice to them and to make them better off.

We really try to find people who you just actively enjoy spending time with. You spend such a large fraction of your life inside the walls and under the roof of whatever organization [or] institution you’re working at, and so, given that I really think it’s worth prioritizing this and I think, I of course don’t know for sure, but I think we go to some greater lengths to find these people than other organizations tend to do. There’s other things as well. It almost goes without saying, but we really care a great deal about ethics and integrity and people, but I think so too do a lot of other organizations.

I think the three that really stand out to me are this rigor and clarity of thought, this hunger, appetite, willfulness, determination, and this … warmth and desire to make people around them better off. Those are three that really stand out to me.

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