Jack Selby was part of the original founding team at PayPal, where he served as SVP of International before going on to become Managing Director at Thiel Capital and later launch his own venture capital fund in Arizona. He joined Sean Kelly on the Digital Social Hour for a relaxed, wide-ranging conversation.
Rather than retracing his resume, the talk stays light — favorite podcast guests, dating stories, and the personal choices that keep him grounded — giving a more casual side of a founding-era tech figure.
About Jack Selby
Jack Selby helped build PayPal from its earliest days as a member of the founding team, later serving as the company's SVP of International. That early experience placed him at the center of one of the most influential companies in internet history.
After PayPal, Selby became Managing Director at Thiel Capital and went on to found his own venture capital fund based in Arizona, continuing to back and build companies well beyond his founding-team roots.
What Jack Selby and Sean Kelly Talked About
- Which guest he considers his favorite from all his podcast appearances
- The story behind traveling 100 miles for a single Tinder date
- Why he chooses not to do drugs, in his own words
- What it's like reflecting on a career that started at PayPal
- How he keeps conversations light even with a heavyweight resume
- A few of the personal habits that keep him sober and grounded
Why This Conversation Matters
This is a lighter, more personal side of Jack Selby than his PayPal-era bio usually shows. It's a fun watch for anyone who wants to see a founding-generation tech figure talk about dating, sobriety, and favorite podcast moments instead of deal terms.
▶ Watch the full episode on YouTube
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About Sean Kelly & the Digital Social Hour
Sean Kelly is an entrepreneur and the host of the Digital Social Hour, one of the fastest-growing interview podcasts in the world, where he sits down with entrepreneurs, athletes, creators, and cultural voices for candid, long-form conversations. The show draws over 100 million views a month across platforms. Explore more guest features on SeanKelly.io.
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