This episode is supported by Xero, helping businesses use AI with more control through JAX, its in-platform AI finance partner. Get 90% off your plan for your first 6 months at xero.com/highflyers.

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Kevin Hartz is the Co-Founder of Eventbrite and Xoom, and Co-Founder and General Partner at A*, the early-stage venture firm whose latest fund is $450M. Xoom was acquired by PayPal for more than $1B, Eventbrite went public, and Kevin has backed some of technology’s most important companies from the earliest stages, including PayPal, Airbnb, Palantir, SpaceX, Anduril, Ramp and Decagon.

In this conversation with Vidit, Kevin goes back to the beginning: growing up in the Bay Area before Silicon Valley became Silicon Valley, studying history at Stanford and Oxford, returning home “fairly lost,” and nearly choosing medicine before the internet pulled him into technology. He shares how friendships with Peter Thiel and the early PayPal team shaped his trajectory, why he chose to build Xoom instead of joining PayPal, and what it felt like to later be “brushed aside” as CEO.

Kevin also reflects on building Eventbrite with his wife Julia while raising a family, the relentless reality of being a scaling CEO, and how identity changes when a company that defined two decades of your life is no longer yours. He explains what the PayPal Mafia taught him about talent, why the best founders create leverage by surrounding themselves with exceptional people, and why some founders are simply an “automatic check.”

They also explore A*, how Kevin finds the next generation of breakout founders, the extraordinary valuations and competition in today’s AI market, why relationships still matter at seed, and what decades of building and investing have taught him about ambition, judgment and the people you choose to spend your life around.

Please enjoy exploring your curiosity.

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This episode is supported by Xero, helping businesses use AI with more control through JAX, its in-platform AI finance partner. Get 90% off your plan for your first 6 months at xero.com/highflyers.

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TIMESTAMPS

00:00 – Meet Kevin Hartz
02:56 – Xero
03:56 – Childhood and family
16:00 – Stanford vs Oxford
21:00 – “I was fairly lost”
24:00 – PayPal, Peter Thiel and Xoom
30:00 – Getting pushed out as Xoom CEO
33:00 – Tech then vs now
35:00 – Why Eventbrite had to exist
43:00 – The reality of being CEO
45:00 – Building with Julia and becoming a dad
48:00 – What the PayPal Mafia taught him
53:00 – Investing in a wild market
56:00 – Who is Kevin Hartz after Eventbrite?
59:00 – Building A* after the SPAC era
1:02:00 – Finding the next great founder
1:04:00 – Why Ashwin was an “automatic check”
1:08:00 – Kevin’s dream dinner table
1:11:00 – The question Kevin asks every founder
1:13:00 – Why “I’d be happy to” is banned at A*

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The High Flyers Podcast features in-depth interviews with the world’s most influential figures in business, tech, finance, government and sport. Launched in 2020, it has ranked in the global top ten for past three years, with listeners in 27 countries and over 200+ episodes released, and featured in Forbes, Daily Telegraph, and at SXSW.

Our guests include -- Malcolm Turnbull (Prime Minister of Australia), Jason Collins (Head of BlackRock, Asia Pacific), Brad Banducci (CEO, Woolworths), Michael Schneider (CEO, Bunnings), David Eckstein (CFO, Legora), Kevin Hartz (Partner, A*; Founder, Eventbrite), Jesse Zhang (CEO, Decagon), Vandita Pant (CFO, BHP), Elena Verna (Head of Growth, Lovable), David Haber (a16z Partner), Jodie Auster (Uber's Global Head of Travel), Rob Giglio (CCO, Canva), Jean-Michel Limieux (CTO, Shopify and Atlassian), Stevie Case (CRO, Vanta), Cristina Cordova (COO, Linear), Gautam Chari (Head of Capital Commitments, Bank of America), John Haddock (CBO, Harvey), Mark Suster (Partner, Upfront Ventures), Niki Scevak (Partner, Blackbird), Craig Tiley (CEO, USA Tennis), Jeanne DeWitt Grosser (COO, Vercel), Paul Bassat (Partner, Square Peg), Bowen Pan (Creator, Facebook Marketplace), Peter Varghese (Secretary of Foreign Affairs, Australian Government), Sam Sicilia (CIO, Hostplus), Jack Zhang (CEO, Airwallex), Tim Doyle (CEO, Eucalyptus), Sukhinder Singh Cassidy (CEO, Xero), Sanjeev Gandhi (CEO, Orica) and Philip Green (Australia's Ambassador/High Commissioner to India).

#273 Kevin Hartz: Studying with Peter Thiel, Founding Eventbrite, Spotting the PayPal Mafia Early & Building A*

The High Flyers Podcast with Vidit Agarwal

#273 Kevin Hartz: Studying with Peter Thiel, Founding Eventbrite, Spotting the PayPal Mafia Early & Building A*