PayPal Mafia
topic on 17 shows · 6 statements across 6 episodes · said 65 times in 45 episodes since 2017
All-In 13 
Acquired 9 
20VC 9 
Sourcery 7 
Founder's Journal 5 
the Neon Show 5 
Lenny's Podcast 3 
My First Million 3 
TBPN 3 
the a16z Podcast 2 
Big Technology 2 
Founders 1 
the Pitch 1 
BigDeal 1 
Capital Allocators 1 
More or Less 
the Knowledge Project
Mentions by year, every show
tap a year for its mentions
All-In 1320VC 9Acquired 9Sourcery 7the Neon Show 5Founder's Journal 5My First Million 3Lenny's Podcast 37 more shows
2026 11 mentions in 7 episodes 2 per episode
- "Dig Through Your Couches. SpaceX Needs It." Cyan Banister on Luke Nosek's Pitch · Sourcery with Molly O'Shea
- Should the US Ban Chinese Open-Source Models | OpenRouter's Chance To Sell | Stripe Buying PayPal
- GPT-6 Hits AGI? Tech Euphoria 2.0, SF Mansion Shortage, NYC Bans AI in Schools & Venezuela Oil Deal
- Chip Stocks Crash, $20B Fund Margin Called, Frontier Labs: SLOW DOWN AI, Mamdani's Grocery Stores
- How Elon Musk Solves Problems | Eric Jorgenson
- Andy Dunn is Building the App to Get You Off Your Phone
- Ed Grefenstette and Sean Warrington – Venture Market Update (EP.488)
- every mention in 2026, scene by scene →
2025 15 mentions in 10 episodes 2 per episode
- Google Part II: Alphabet (Audio) · Acquired
- What 20 Years of Investing taught Somesh Dash of IVP after backing Perplexity, Figma, Dropbox
- Google Part III: The AI Company. Google is amazingly well-positioned... will they win in AI? (Audio) · Acquired
- Keith Rabois: Lessons from PayPal Mafia, $OPEN, & Investing · Sourcery with Molly O'Shea
- He saved OpenAI, invented the “Like” button, and built Google Maps: Bret Taylor (Sierra)
- Grok 4 Wows, The Bitter Lesson, Third Party, AI Browsers, SCOTUS backs POTUS on RIFs
- Unconventional product lessons from Binance, N26, Google, more | Mayur Kamat (CPO at N26)
- Is OpenAI's o3 Model AGI? Is AI The New Social Media? Zuck's Revealing Testimony
- 2 more episodes that year, every mention in 2025 →
2024 17 mentions in 14 episodes 1 per episode
- The All-In Holiday Spectacular
- $100B Founder Breaks Down The Biggest AI Business Opportunities For 2025
- How to Spend a Trillion Dollars Fast (ep13)
- Meta (Audio) · Acquired
- Lessons in product leadership and AI strategy from Glean, Google, Amazon, and Slack | Tamar Yehoshua
- Dmitry Gurski: From Potato Farm to $200M in Revenue: The Never-Before-Told Story of Flo Health|E1205 · 20VC with Harry Stebbings
- How To Grow An Audience If You Have 0 Followers
- David Cahn: Why Servers, Steel and Power Are the Pillars Powering the Future of AI | E1186 · 20VC with Harry Stebbings
- 6 more episodes that year, every mention in 2024 →
2023 2 mentions in 2 episodes 1 per episode
2022 9 mentions in 5 episodes 2 per episode
- #AIS: Pear VC’s Mar Hershenson on making successful founders
- ACQ Sessions: Jason Calacanis · Acquired
- Jeffrey Katzenberg & Sujay Jaswa: Takeaways from Dreamworks; What happened with Quibi? | 20VC #952 · 20VC with Harry Stebbings
- Brian Singerman: How I Became a Partner at Founders Fund, Why We Put $400M into Anduril | 20VC #943 · 20VC with Harry Stebbings
- Amazon.com · Acquired
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2021 6 mentions in 3 episodes 2 per episode
2020 2 mentions in 2 episodes 1 per episode
- 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*
- Episode 54 | Rahul Chandra, Managing Director, Unitary Helion Fund
- every mention in 2020, scene by scene →
2019 2 mentions in 1 episode
every mention on every show, scene by scene, with the transcript →
6 statements about PayPal Mafia, every show
Taylor: PayPal Mafia learned more about entrepreneurship than Google PMs
“Folks like the PayPal mafia, I think learned a lot more about entrepreneurialism than like a typical PM at Google.”
Coogan: PayPal Could Have Reached $1T Valuation Under Original Founders
“Like I could have been running something that I think PayPal's peak market cap is like a hundred billion could easily be a trillion if they were still there.”
Lessin: Tech 'mafias' cannot form today because talent is too dispersed
“Now the problem is, is like, there, it's very hard to build mafias because there's just too much going on. Like, there are too many good places for talent to go. It's not concentrated the same way”
Singerman: Deal sourcing grows harder as venture capitalists age and networks decay
“The part that's just harder and harder over the years as you do this longer and quite frankly get older is the seeing. You've got to keep your networks fresh. You've got to like make sure that you're somehow still connected, right? Cause your networks get stal…”
Without Amazon outbidding eBay for Accept.com, PayPal might not exist
“If that had gone otherwise, I don't know about PayPal. Like, there's probably no PayPal. There might not be a PayPal mafia.”