Aug 4, 2026
Braindump on what made Stripe great (c. 2018):
- almost everyone was agentic, smart, and conscientious.
- agentic matters because ppl go out and find new ideas without being told. Also creates very high positive energy that's impossible to replicate merely by top down pressure.
- intelligence matters because ideas, execution, process, etc. are just better (and more fun).
- conscientious matters because you get no slop and great delivery. Ppl chase things down to bedrock, then actually follow through. Everything you read is super high quality. (But it does demand tremendous energy expenditure; not for everyone)
- tons of experienced ppl from world-class institutions. You can call it credentialism, but it also meant any question you have, there is a world-class expert on that topic. Pricing, engineering, m&a, product, ops, finance, whatever niche topic you might care about, etc.
- creativity was amplified by a very lightweight process that kept ppl from doing dumb things. Basic stuff-- talk to customers, validate hypotheses, decide what you're not doing, fast demos, etc. Blindingly following the template would alone produce surprisingly good results.
- an ambient value that quality is its own reward. Stripe didn't need good design but had a killer design team for this reason. But you'd see this in everything.
- the org produced tons of very high quality signals that were aggregated up to the exec team, they'd process the signals, guidance would diffuse down, the process would repeat. You could clearly see information pulse up and down the org, which gave a distinct feeling that every single person had tangible input into company direction.
- incidentally, the previous point results in a much better company strategy. It only works if the signals are high quality though, which can only happen if the talent bar is high.
- charismatic founders. That goes a really really long way.
- frequent reorgs. A lot of ppl see it as a negative (which I can understand-- reorgs can be stressful). I always saw it as continuous org-level garbage collection and refactoring. A counterfactual in which a fast-growing company isn't doing this would produce much more painful problems imo.
There is probably a lot more stuff, but I'm running out of steam.