Show notes
On Episode 300 of the Business of Betting podcast, Jeff Edelstein is joined by Barstool Sports founder Dave Portnoy for a candid conversation covering the rise of Barstool, the ESPN Bet partnership, gambling regulation, cancel culture, media, politics, philanthropy, and what the future might hold, including a possible run for public office.
Hear them discuss:
Why the Barstool Sportsbook partnership ultimately failed, what went wrong with ESPN Bet, and how strict regulatory oversight limited Barstool's ability to market authentically.
Dave's approach to building Barstool's culture, creating viral content, and empowering talent behind brands like Pardon My Take, Call Her Daddy, and The Pat McAfee Show.
The origin of the iconic One Bite Pizza Reviews and how a simple office debate turned into one of Barstool's biggest brands.
The story behind The Barstool Fund, raising over $50 million to help hundreds of small businesses survive the COVID-19 shutdowns.
How Dave navigates controversy, media criticism, cancel culture, and where he draws the line between accountability and online outrage.
Dave's views on politics, why he believes more outsiders should enter public service, and whether a future political campaign is truly on the table.
His perspective on antisemitism, social media polarization, and why he has become more outspoken in recent years.
The business lessons behind Barstool's growth, why authenticity beats traditional media, and how Dave evaluates creative talent.
Dave's passion for sports betting, horse racing, investing, and why he still loves wagering despite decades in the industry.
What's next for Dave Portnoy—from Barstool's future to horse racing ambitions, and why he believes his biggest challenge may still be ahead.
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