Sep 28, 2026
What made Stripe great, c. 2016 (Part II)
- p&j would talk to anyone any time. You could dm them and get a near instant response. If you needed to meet them they'd always find 15m for you. They'd do that with everyone, you didn't have to be a high-ranking employee. It's impossible to overstate how accessible they were. (We all tried really hard to use this sparingly to protect their time, though in hindsight from their pov it must have looked like ppl are avoiding them)
- if you abstract this a little, these informal connections functioned like dozens of bidirectional probes inserted throughout the org. It let ppl give information directly to the founders, and let p&j steer the company outside of standard channels. This probably contributed to Stripe's success as much as the formal process
- everyone was extremely optimistic, not just about Stripe but about the world as a whole. There was this conviction that the world can be improved, that there is no limit to this, that making it better is everyone's responsibility, and that big improvements are within reach. Stripe of that time was brimming with noblesse oblige
- one tangible example of this is Stripe Press. There is no commercial reason for it to exist. Why spend management bandwidth on publishing a beautiful meticulously typeset hardcover of The Making of Prince of Persia? The only reason is a strong conviction that putting these books on people's shelves materially improves the world. (Btw you can experience that sense of optimism yourself. Buy a Stripe Press book, you will feel it the moment you hold it in your hands)
- everyone without exception had an egalitarian mindset. In hypergrowth startups you have OGs with $50M worth of options and new employees who basically just got a normal job. Not one time did I sense even a shade of this in any interaction. All anyone ever thought about was contributing to building the rocket ship as best they could
- p&j were surprisingly good writers. (I think Patrick was more prolific, maybe three essays for every one of John’s, but both were very good. My memory might be off though.) Running Stripe demanded an insane rate of learning of them. Every time they'd work out some new problem they'd write about it, so in a sense everyone got to learn with them. The essays were typically far more perceptive than the best ft/economist writing imo
- the executive team was felt everywhere yet had a very light touch. If you picture a company as a growing clump of cells, execs would be standing to its side, collecting vitals, reading signs, tending here, nudging there, pruning the occasional bad cell. They could be commanding when necessary but reaching for chain of command was not their first instinct
- Stripe felt incredibly bottom up. p&j would declare a goal and at every level people did their best to reorient their corner of the company in the goal's direction. There are tradeoffs to this. The upside is that the company was remarkably agile, more fun to work in, more inventive. The downside is that it often could be totally unobvious what to do, you'd have to figure it out yourself
- this wasn't for everyone. If you needed a lot of structure you'd be screwed. But if you loved it you *really* loved it. Stripe selected for those people. You were surrounded by scrappy, tenacious, intrepid colleagues, it was probably the best part of working there