Stripe CEO Patrick Collison wishes he could be a ‘cave dwelling’ remote worker

Stripe has its fair share of people who would prefer to work remotely, most notably the CEO. In the world of fintech startups, however, it’s a luxury not all can afford. In a recent fireside chat at Berkeley Haas business school, CEO Patrick Collison spoke on remote work, internal meetings, intense hours, and the importance of honesty.

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In-office trumps remote for early stage startups.

Collison calls himself a “cave dweller,” preferring to work remotely if possible, despite not being “in a role where that makes sense.” However, he doesn’t deny the obvious benefits of in-person work, particularly for early-stage companies.

Companies with around 50 employees “that exercise that option [of working in-person] really seem to do better,” Collison said. “And I think we all intuitively kind of know it.” 

This is not to say that hours in the office is a metric for success at Stripe. Given its expanded headcount and growing global presence, Collison says Stripe employees “can’t all fit in the same room” anymore, and “there’s no universe in which we’re not having loads of Zoom meetings.” 

Collison says catering to both in-office advocates and remote workers creates a “significant efficiency gain.” Co-founder John Collison has previously stated that teams with remote workers tend to consist entirely of remote workers, which also streamlines the process.

Internal meetings aren’t always popular.

Patrick described his brother John as the “front-man” of Stripe. John may be a big fan of internal meetings, but it seems he was the outlier in Stripe’s early days.

Patrick described the team as a group of “misanthropic introverts,” preferring to communicate in writing as it was “less oppressive.” The key benefit of this for Collison is that it makes “our past selves look stupider, and that’s actually very adaptive.” With physical evidence, it’s harder to avoid confronting previous poor decisions.

11pm was an early finish at Stripe…

Things might have changed, given the scale of the business today, but the early days of Stripe were very intensive and “never fun.” Collison said he remembered “vividly how intently and intensely we worked.”

Collison said one of the earlier employees ended up moving from San Francisco to Palo Alto, where Stripe was based. This was because the last train back to San Francisco left at 11pm, and he “felt guilty leaving the office early every evening.” 😨

Being Right > Being Consistent

Radical Transparency isn’t a tenet reserved only for Bridgewater Associates. At Stripe, Collison says that if someone has “constructive feedback, and you’re not telling them, I think you’re really undermining trust.”

Keeping it real with Patrick is more likely to get you in his good books. He said “the people at Stripe with whom I feel the greatest trust are, to a significant extent, those who give me the most critical feedback.”

Who inspired Collison to quit MIT?

One of the most influential people in Stripe’s existence likely has no clue who Collison is.

When studying mathematics at MIT, Collison chose a particularly difficult physics module. It had a punishing midterm, with an average score of 43. Everyone’s results were public, and Collison scored 70, but he “saw that this guy, Yufei Zhao, had gotten a 97.”

Collison said he has “never interacted with Yufei Zhao, I don’t think he’s heard of me,” but still described the event as “a big moment in my life.” He thought, “if Yufei Xiao exists and can be so spectacularly better than me at Physics, maybe I shouldn’t become a physicist.”

Collison subsequently dropped out of MIT. Zhao, meanwhile, has gone on to great things himself; he studied at both Oxford and Cambridge, won awards, and has been a mathematics professor at MIT for the past seven years.

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