On this episode of the Knowledge Project Podcast, I chat with Patrick Collison, co-founder and CEO of the leading online payment processing company, Stripe. If you’ve purchased anything online recently, there’s a good chance that Stripe facilitated the transaction.

What is now an organization with over a thousand employees and handling tens of billions of dollars of online purchases every year, began as a small side experiment while Patrick and his brother John were going to college.

During our conversation, Patrick shares the details of their unlikely journey and some of the hard-earned wisdom he picked up along the way. I hope you have something handy to write with because the nuggets per minute in this episode are off the charts. Patrick was so open and generous with his responses that I’m really excited for you to hear what he has to say.

Here are just a few of the things we cover:

The biggest (and most valuable) mistakes Patrick made in the early days of Stripe and how they helped him get better
The characteristics that Patrick looks for in a new hire to fit and contribute to the Stripe company culture
What compelled he and his brother to move forward with the early concept of Stripe, even though on paper it was doomed to fail from the start
The gaps Patrick saw in the market that dozens of other processing companies were missing — and how he capitalized on them
The lessons Patrick learned from scaling Stripe from two employees (he and his brother) to nearly 1,000 today
How he evaluates the upsides and potential dangers of speculative positions within the company
How his Irish upbringing influenced his ability to argue and disagree without taking offense (and how we can all be a little more “Irish”)
The power of finding the right peer group in your social and professional circles and how impactful and influential it can be in determining where you end up.
The 4 ways Patrick has modified his decision making process over the last 5 years and how it’s helped him develop as a person and as a business leader (this part alone is worth the listen)
Patrick’s unique approach to books and how he chooses what he’s going to spend his time reading

...life in Silicon Valley, Baumol’s cost disease, and so, so much more.

Patrick truly is one of the warmest, humblest and down-to-earth people I’ve had the pleasure to speak with and I thoroughly enjoyed our conversation together. I hope you will too!

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#32 Patrick Collison: Earning Your Stripes

The Knowledge Project with Shane Parrish