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Caleb Pressley on Putting All of His Money into Bitcoin and Which Barstool Employees Own Crypto

This is an episode of The Pomp Podcast with host Anthony “Pomp” Pompliano and guest, Caleb Pressley, one of the most electric people on the internet. He currently works at Barstool Sports, runs the @thinker account on Instagram, and previously played football at the University of North Carolina.

In this conversation, we discuss college football, pro athletes creating content and building audiences, social media trends, default digital value of assets, volatility as Bitcoin’s PR team, and many behind the scenes stories of Caleb’s escapades.

Pomp writes a daily letter to over 50,000 investors about business, technology, and finance. He breaks down complex topics into easy to understand language while sharing opinions on various aspects of each industry. You can subscribe at

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