PayPal Mafia, every mention

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every year anyone Harry Stebbings 3Rory O'Driscoll 2Kevin Hartz 1Dmitry Gurski 1David Cahn 1Brian Singerman 1

Verbatim, from the transcripts: the passages where PayPal Mafia comes up

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Should the US Ban Chinese Open-Source Models | OpenRouter's Chance To Sell | Stripe Buying PayPal Jul 23, 2026 · 2 mentions

  • ▶ 57:16 Rory O'Driscoll My guess is this is one where you have, frankly, one well-won company for the last decade and a half in Stripe, and you have another company that, you know, ever since the PayPal mafia walked out has been just a revolving door of… 2 times in the scene

Max Levchin, Founder & CEO @ Affirm:The Biggest Surprise Scaling to $18.7BN Market Cap · 20VC with Harry Stebbings Feb 5, 2025 · 1 mention

  • ▶ 53:05 Harry Stebbings If you could start a company with only one member of the PayPal mafia again, who would it be?

Dmitry Gurski: From Potato Farm to $200M in Revenue: The Never-Before-Told Story of Flo Health|E1205 · 20VC with Harry Stebbings Sep 23, 2024 · 1 mention

David Cahn: Why Servers, Steel and Power Are the Pillars Powering the Future of AI | E1186 · 20VC with Harry Stebbings Aug 5, 2024 · 1 mention

  • ▶ 53:37 David Cahn Roloff is always telling this story about how at PayPal, the best moments of PayPal are when the company was running out of money, and the company just had to figure it out, and you talk about the PayPal mafia, everyone was so great.

Jeffrey Katzenberg & Sujay Jaswa: Takeaways from Dreamworks; What happened with Quibi? | 20VC #952 · 20VC with Harry Stebbings Nov 26, 2022 · 1 mention

Brian Singerman: How I Became a Partner at Founders Fund, Why We Put $400M into Anduril | 20VC #943 · 20VC with Harry Stebbings Oct 31, 2022 · 1 mention

20VC: SPACs. What Are They? Why Now? How Do They Change The Venture Landscape? Are They Better Than IPOs & Direct Listings? How Should Founders Think About Them? Kevin Hartz & Troy Steckenrider @ A* Aug 31, 2020 · 1 mention

  • ▶ 27:22 Kevin Hartz And that's been very informative all the way back to the PayPal days of having the honor of watching the PayPal mafia really grow and proliferate into some really incredible people, really changing the world.

20VC: Why Valuation Is Of Critical Importance At Seed, How To Understand Innovation Cycles & Having 3 CEOs and Burning $10m a Month with Lee Hower, Co-Founder @ NextView Ventures Mar 8, 2017 · 1 mention

  • ▶ 4:48 Harry Stebbings What an incredible story, but I do have to ask, then, a natural kind of subsequent question from that is, what did you learn, then, in the subsequent years from working with the various members of the so-called PayPal mafia and how they…
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