Dave Portnoy On Cancel Culture, Kanye West, Skip Bayless, LeBron, Tom Brady, Taylor Swift, Celtics, Patriots, Barstool Sports & Call Her Daddy

In Part 1 of this episode of Club Shay Shay, Shannon Sharpe sits down with Dave Portnoy—founder of Barstool Sports, one of the most influential figures in modern sports media. A business trailblazer and digital powerhouse, Portnoy—known as “El Presidente”—is a University of Michigan alum who turned a small free sports newspaper into a multi-platform empire now valued at over half a billion dollars. An outspoken personality, social media icon, and pizza aficionado, Dave built Barstool Sports into a cultural movement by doing things his way—and never backing down.

Portnoy breaks down how he started Barstool as a free newspaper in Boston, why he named it "Barstool," and how being high school classmates with ESPN’s Todd McShay shaped part of his journey. He explains how Barstool capitalized on raw, unfiltered media, his admiration for Bill Simmons, and how his love for gambling played a key role in shaping the brand’s voice.

We explore his Massachusetts roots, how the company exploded in popularity among college audiences, and how Barstool grew to surpass legacy networks in social media dominance. Portnoy opens up about firing people publicly, and working with big names like Wallo267 and Gillie, Pat McAfee, Coach Jon Gruden, Bussin’ With The Boys, and Alexandra Cooper of Call Her Daddy. He also talks about the fallout with Cooper and Caleb Pressley, the future of sports media, and why he’s always hunting for the next big star. Plus—his take on Jon Gruden saying Roger Goodell “hates football.”

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