Go to https://ziprecruiter.com/SHAYSHAY right now to try ZipIntro for free. In 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.” Dave opens up about the deal that shocked the industry—selling Barstool for $500 million and then buying it back for just $1. He explains why he doesn't believe he can be cancelled, why he rarely apologizes, and how he’s thrived by embracing controversy. From beefs with Jason Whitlock and Michael Rapaport to the Angel Reese vs. Caitlin Clark debate and calling Reese “classless”, Portnoy gives his unfiltered opinions. He breaks down his best and worst purchases, winning $2.6 million betting on UConn, being called a "legitimate degenerate" by his dad, and his past bankruptcy. He weighs in on crypto scams, the Hawk Tuah crypto controversy, and even Gisele Bündchen moving on from Tom Brady. He talks about his ex-wife still able to access his bank account and his defense of Taylor Swift against Kanye West. He also dives into the TikTok ban, Mahomes vs. Brady, Jerod Mayo’s unfair exit from the Patriots, and his Top 5 Celtics of all time. He speaks on the Lakers getting Luka Doncic, Bronny James entering the NBA, Larry Ellison’s recruiting tactics with Bryce Underwood, and interviewing Donald Trump. Portnoy talks his past run for mayor of Boston, shares the best advice he’s ever received, and reveals his Top 5 fast food chains. This is Dave Portnoy—raw, controversial, unapologetic, and more transparent than ever. You don’t want to miss this brutally honest, wildly entertaining deep-dive into the mind of one of the most polarizing and powerful figures in sports media. #ClubShayShay​ #DavePortnoy #BarstoolSports Buy LePortier: https://leportiercognac.com/products/shay_vsop_750ml/ SUBSCRIBE to get the latest Club Shay Shay content: https://www.youtube.com/c/ClubShayShay?sub_confirmation=1 Listen to the Club Shay Shay podcast on Apple Podcasts: https://podcasts.apple.com/us/podcast/club-shay-shay/id1531023690 Listen to the Club Shay Shay podcast on Spotify: https://open.spotify.com/show/060hDdnydsJyMi17TmvyAh?si=iuda1z7oTE-21ZYzwiUdhg&nd=1 Like Club Shay Shay on Facebook: https://m.facebook.com/ClubShayShay/ Follow Club Shay Shay on Twitter: https://x.com/clubshayshay?s=21&t=PF1soCgsTT_NEerDJm9Lfg Follow Club Shay Shay on Instagram: https://instagram.com/clubshayshay?igshid=MzRlODBiNWFlZA== Follow Shannon Sharpe on Twitter: https://x.com/shannonsharpe?s=21&t=PF1soCgsTT_NEerDJm9Lfg Follow Club Shay Shay on Tik Tok: https://www.tiktok.com/@clubshayshaypod?_t=8fJ79WZy2fb&_r=1 About Club Shay Shay: Club Shay Shay is a weekly podcast hosted by Shannon Sharpe – 3x Super Bowl champion, member of the Pro Football Hall of Fame and co-host of First Take on ESPN. Each week Shannon will sit down with athletes, celebrities and influencers to break down, analyze and discuss the latest headlines in sports, pop culture and everything in-between. Get on the VIP list at Club Shay Shay NOW and never miss an episode! Dave Portnoy | EP. 168 Link of Ep. https://youtu.be/r67t8z6sNOo Club Shay Shay https://www.youtube.com/c/ClubShayShay