My guest today is John Collison, the Co-Founder of the digital payments company Stripe. Stripe’s mission is to increase the GDP of the internet, a lofty and deeply interesting pursuit. John is clearly a voracious learner across business and investing, which you’ll hear instantly. He started Stripe with his brother Patrick when he was just 19 years old, and has grown it to, at last valuation, a $36B business. In our conversation, we discuss conglomerates, the internet economy, the power of writing, and why board members are like Pokémon characters, each with different powers. It’s a lively and wide-ranging conversation with one of the entrepreneurs I’ve most enjoyed speaking with. Please enjoy.

For more episodes go to InvestorFieldGuide.com/podcast.

Sign up for the book club, where you’ll get a full investor curriculum and then 3-4 suggestions every month at InvestorFieldGuide.com/bookclub.

Follow Patrick on Twitter at @patrick_oshag

Show Notes

(1:30) – (First question) – Interest in industrial conglomerates

(9:10) – Their thinking on acquisitions vs starting new companies

(11:42) – How the payment landscape looked when Stripe was started

(15:55) – View on the internet economy

(20:09) – Exciting possibilities for the future of the internet economy

(22:11) – The forces of size vs speed among startups

(26:53) – Driving reasons why employees choose Stripe starting with clear communication

(28:55) – Tips for better internal communications

(30:09) – The importance of rigor in Stripe’s corporate culture

(32:15) – Investors and investing styles that are most intriguing to him

(36:02) – Teaching vs experiencing business lessons

(37:56) – Lessons from going to market with new ideas

(50:58) – Allowing teams to explore new ideas at Stripe

(44:11) – Best startup companies to study to understand the history of this space

(44:52) – Softwar: An Intimate Portrait of Larry Ellison and Oracle

(48:18) – Cable Cowboy: John Malone and the Rise of the Modern Cable Business

(48:43) – Infrastructures of internet businesses that are missing

(52:03) – Does general accounting practices need to change to capture the true value of a company like Stripe

(1:01:53) – Shared playbooks in Silicon Valley

(1:02:02) – The transition to the no code movement

(1:08:22) – Other businesses that pique his interest outside of software

(1:10:21) – Future trends that excite him

(1:11:10) – First memory when he felt like he was participating in the tech economy

(1:12:46 – The role of board members

(1:15:48) – Kindest thing anyone has done for him

(1:18:49) – Advice for young people

Learn More

For more episodes go to InvestorFieldGuide.com/podcast.

Sign up for the book club, where you’ll get a full investor curriculum and then 3-4 suggestions every month at InvestorFieldGuide.com/bookclub

Follow Patrick on Twitter at @patrick_oshag

Lockheed Martin CTO Ray Johnson