Kevin Hartz | Backing Teen Founders, Lessons from the PayPal Mafia
Show notes
Kevin Hartz, Co-founder of A*, Eventbrite, Xoom, and Sauron. Kevin has been building and investing in technology companies for 30 years, and we talk about how the industry’s evolved, why he calls AI the Mother of All Bubbles, why we’re still early, and lessons today’s breakout AI companies can learn from those that survived the Dot Com Crash. Kevin is a big proponent of backing young founders. A significant percentage of his latest fund at A* is invested in teenagers, and he shares how he identifies outlier talent so early, from Seed investments in Airbnb, PayPal, and Pinterest, to many of today’s hottest AI companies. He also shares the insane story of investing 100% of the proceeds from his first startup into PayPal’s Seed round, how PayPal’s early fraud systems inspired Palantir, what he learned from the PayPal Mafia, from Peter Thiel, and what makes Founders Fund special. We also talk about how he and his wife recently had two babies, five months apart, using genome screening and surrogates. Thanks to Ramtin Naimi, Navya Gudimetla, and Bennett Siegel for helping brainstorm topics for the conversation. Try Numeral, the end-to-end platform for sales tax and compliance: https://www.numeral.com Sign-up for Flex Elite with code TURNER, get $1,000: https://form.typeform.com/to/Rx9rTjFz Timestamps: (4:25) Power shift from VC’s to founders since the 90’s (9:08) AI is the mother of all bubbles (12:40) Why AI is still underhyped (14:10) What Kevin and A* are investing in today (16:02) Investing 100% of his first startups proceeds in PayPal’s Seed round (21:21) What made the PayPal Mafia special (23:37) Parallels between the 90’s and today (26:40) What makes Founders Fund special (35:07) How Palantir evolved from PayPal’s fraud models (39:06) Building Xoom on the PayPal API (43:38) Lessons between Kevin’s 1st and 2nd startups (46:52) Starting Eventbrite off early PayPal API app (51:51) Eventbrite’s hidden TAM challenge (53:49) Selling Eventbrite to Bending Spoons (54:59) Investing 20% of A* in teenage founders (1:02:33) Incubating Sauron, the home security company (1:08:44) Making breakfast for our kids (1:13:33) Having kids with genome screening and surrogates (1:20:31) Collecting art, how to get started Referenced https://www.a-star.co/ https://www.eventbrite.com/ https://www.xoom.com/ https://www.sauron.systems/ https://www.orchidhealth.com/ Setting the Table by Danny Meyer: https://www.amazon.com/Setting-Table-Transforming-Hospitality-Business/dp/0060742763 20% of fund in teenage founders: https://techcrunch.com/2025/10/18/this-top-vc-bet-close-to-20-of-his-fund-on-teenagers-heres-why/ https://nypost.com/2025/12/14/us-news/xu-bo-chinese-billionaire-reportedly-sires-more-than-100-kids/ Follow Kevin Twitter: https://x.com/kevinhartz LinkedIn: https://www.linkedin.com/in/hartz Follow Turner Twitter: https://twitter.com/TurnerNovak LinkedIn: https://www.linkedin.com/in/turnernovak Subscribe to my newsletter to get every episode + the transcript in your inbox every week: https://www.thespl.it/
Guests
Analysis: done · source seed