During its formative years in the late 1990's, Paypal attracted an extraordinary group of young entrepreneurs, who then went on to build some of the best known companies in tech. They became known as The PayPal Mafia—and Max Levchin was one of the leaders. A computer genius from Soviet Ukraine, Max joined Peter Thiel, Elon Musk, Reid Hoffman and others as they grew PayPal into a massively successful online payment service. Along the way, they encountered almost every start-up challenge imaginable, including the emotional ouster of Elon Musk as CEO. After PayPal was acquired by eBay in 2002, Max couldn't sit still, so he launched a startup lab that eventually led to another successful fintech company: Affirm.

This episode was produced by Alex Cheng with music by Ramtin Arablouei. Edited by Neva Grant, with research from Claire Murashima.

You can follow HIBT on X & Instagram, and email us at hibt@id.wondery.com. Sign up for Guy’s free newsletter at guyraz.com

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Herschel Supply Co. co-founder Lyndon Cormack joins Guy on the Advice Line, where they answer questions from three early-stage founders about leveraging brand stories to reach new customers.

Today we meet Lauren in Michigan, a former journalist now capturing family histories in bespoke commemorative books. Then Jon in London, whose creation might be a solution for the pile of clothes on your chair. And Virginia in Alaska, who designed a bra that stays comfortable through a 12-hour nursing shift—and now wants to expand to the lower 48.

Thank you to the founders of Memory Lane Jane, Floordrobe, and SWOOP for being a part of our show.

If you’d like to be featured on a future Advice Line episode, leave us a one-minute message that tells us about your business and a specific question you’d like answered. Send a voice memo to hibt@id.wondery.com or call 1-800-433-1298.

And be sure to listen to Herschel Supply Co.’s founding story as told by Lyndon and his brother Jamie on the show in 2023.

This episode was produced by Alex Cheng with music by Ramtin Arablouei. It was edited by John Isabella. Our audio engineer was Cena Loffredo.

You can follow HIBT on X & Instagram and sign up for Guy's free newsletter at guyraz.com or on Substack.

See Privacy Policy at https://art19.com/privacy and California Privacy Notice at https://art19.com/privacy#do-not-sell-my-info.

Monica Lewinsky has been a major reference in pop culture since she was 24 years old when a scandal made her a household name overnight. Since then, she’s fought to redefine her reputation - and now, she's ready to encourage others to take back their power, too.

On her new podcast "Reclaiming with Monica Lewinsky," Monica leads honest and wide-ranging conversations about what it means to write your own narrative. Each week, guests share how they've rediscovered purpose, rebuilt relationships, and redefined success after their most vulnerable moments.

This is just a preview of Reclaiming with Monica Lewinsky. You can listen to the full episode wherever you get your podcasts, or here: Wondery.fm/ReclaimingWithMonicaLewinsky

See Privacy Policy at https://art19.com/privacy and California Privacy Notice at https://art19.com/privacy#do-not-sell-my-info.