This episode first aired in May 2018. This is a Knowledge Project Podcast episode from the archive.

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Patrick Collison, CEO, and co-founder of Stripe shares wise insights on success, failure, management, decision making, learning and so much more.

In this conversation, 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, and so much more.
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Timecodes:

00:00 - Collison’s journey from dropping out to founding Stripe
09:58 - On Stripe’s culture
15:30 - Lessons learned from the early days of Stripe
21:51 - What Collison has learned from scaling Stripe
30:04 - On specialization vs generalization
37:48 - How Collison manages risk and large downsides
41:09 - On “thoughtful disagree-ness”
45:07 - How Collison has modified his decision making process
55:22 - The company culture's Collison admires
59:13 - What Collison learned from studying Koch Industries
1:00:57 - On Collison's reading habits
1:19:15 - Collison's smallest habits that make the biggest difference
01:21:55 - Mistakes Collison sees people make
01:24:39 - The future of online payments
01:37:00 - Success and Silicon Valley

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Like the mentor you’ve always dreamed of having, The Knowledge Project shares timely yet timeless lessons for work and life. Past guests include Naval Ravikant, Daniel Kahneman, Jim Collins, Angela Duckworth, Seth Godin, Melanie Mitchell, & Esther Perel.