What Stripe Gets Right

I recently made the decision to leave Stripe and join Macro Oceans full time. This was a difficult decision and was more about not wanting to miss the opportunity to build Macro Oceans rather than quitting Stripe.

While I was working at YouTube, I began doing something that really helped me: team and company cultures the way I would about a friend. They have a lot of good qualities and some faults. [0]

But when you’re working somewhere everyday, even little faults can be really grating, the way that you might have a friend you really enjoy who you can’t stand after two weeks traveling together.

Part of my breakthrough was to spend more time focusing on the virtues rather than the faults. I also began to accept that the faults developed over time and would take time to change. This made it easier for me to navigate through the things that drove me a little crazy: it was part of what made the place what it was.

With this context, I want to reflect a little bit about what Stripe gets right, if only so I can remember it. These aren’t the only things about Stripe or a balanced picture of what it’s like to work there, but the things I want to remember and to emulate. [1]

0: At every company where I’ve worked as an adult, with one possible exception, the good qualities outweighed the faults pretty significantly.

1: I enjoyed my time at Stripe and on some level wish it had been longer. If you’re considering a job at Stripe and want more detail about my experience, feel free to reach out: jdillaxyz@gmail.com.

2: The possible exception here is Bain. The difference that at Stripe the talent level is high and distributed across functions whereas Bain everyone basically did the same thing — corporate strategy.