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Mr Z

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Medial • 3h

This is the greatest heist in business history. This guy sold his company for $550M... Then bought it back for JUST $1. The original buyers lost $800M in the process. Here's the incredible story of how Dave Portnoy won his company back. In 2003, Dave Portnoy launched a small betting newspaper in Boston. At first, it was ignored—until he put women in bikinis on the cover. The paper gained attention and grew. In 2007, as print media struggled, Dave went online and created Barstool Sports, a raw, unfiltered alternative to polished media like ESPN. By 2020, Penn Gaming bought Barstool for $551M. But Barstool’s bold style caused regulatory issues in the gambling industry. In 2023, Penn sold Barstool back to Dave for $1 to secure a $2B deal with ESPN. Dave kept creative control and declared he’d never sell again. Now, Barstool thrives with total freedom, new partnerships, and multiple revenue streams—truly a masterclass in business. Follow for more valuable content like this.

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