E300 - Dave Portnoy from Barstool Sports

On Episode 304 of the Business of Betting podcast, Jeff Edelstein is joined by Adam Bjorn, CEO of Plannatech Group, for a wide-ranging discussion on his three decades in sports betting, Prime, prediction markets, U.S. regulation, and the future of the industry.   Hear them discuss: How Adam got his start in sports betting in Australia and the cultural influence of the Melbourne Cup. Why America's growing gambling and gaming culture could create risks as sports betting, prediction markets, and iGaming expand. The challenges of operating across 50 different U.S. regulatory environments, including taxes, market-access costs, and the federal excise tax. Why Adam decided to acquire Prime and the opportunity he sees in competing for customers in the unregulated market. How prediction markets are attracting professional, syndicate, and recreational bettors away from traditional sportsbooks. Why Adam believes prediction markets are not a new concept and how the U.S. market's liquidity and large consumer base have accelerated their growth. How the World Cup became a major coming-out party for prediction markets, with enormous trading volumes on platforms like Kalshi and Polymarket. Why Prime is focused on grassroots growth, customer service, and carving out a niche rather than competing with the industry's biggest marketing spenders. Adam's experience with U.S. regulators and why he believes changes to taxation could make the regulated sports betting market more sustainable. The evolution of sports betting over Adam's 30-year career, from handwritten ledgers and phone betting to live betting, massive data availability, and AI-powered betting insights.   ⚡️ Follow BoB on Twitter/X ⚡️ Watch BoB on Youtube ⚡️ Apply to be a guest here

On Episode 303 of the Business of Betting podcast, Jeff Edelstein is joined by Jonathan Cohen, Policy Lead at the American Institute for Boys and Men and author of Losing Big, for a wide-ranging discussion on sports betting regulation, the challenges facing young men, prediction markets, gambling education, dopamine-driven technology, and the future of responsible gambling policy.   Hear them discuss: Why Jonathan believes sports betting should remain legal, but argues its rapid post-PASPA rollout lacked the guardrails needed to protect younger and more vulnerable consumers. How the challenges facing boys and young men from economic uncertainty to shifting ideas of masculinity can make gambling, prediction markets, and other high-risk activities especially appealing. Why gambling should be viewed alongside crypto, day trading, collectibles, online casinos, social media, and other dopamine-driven products competing for people's attention. Whether sportsbooks, prediction markets, and regulators should introduce more friction through default betting limits, waiting periods, and restrictions on high-frequency betting products like microbets. Why Jonathan believes prediction markets may pose even greater consumer risks than traditional sportsbooks by marketing themselves as opportunities to make money. How advertising shapes public perception of gambling, investing, and financial success, and why younger bettors may be especially vulnerable to those messages. The similarities between gambling, alcohol, pornography, social media, and other modern technologies that exploit the brain's dopamine reward system. Jonathan's outlook on the future of gambling regulation, why today's debates may look very different five years from now, and what reforms he believes are both realistic and achievable. Jonathan's unexpected work as a Bruce Springsteen scholar, what he learned from studying Springsteen's fanbase, and why great art means something different to every listener.   ⚡️ Follow BoB on Twitter/X ⚡️ Watch BoB on Youtube ⚡️ Apply to be a guest here

On Episode 302 of the Business of Betting podcast, Jeff Edelstein is joined by Zack Panos, founder of 4Casters, for a deep dive into the future of prediction markets, peer-to-peer betting, and the evolving sports betting ecosystem.  Hear them discuss: Zack's journey from learning poker and risk management as a child to founding 4Casters and building a peer-to-peer betting exchange. Why prediction markets have gained momentum, how they differ from traditional sportsbooks, and why California and Texas have become key battlegrounds for their growth. The future of liquidity, market makers, pricing, and why Zack believes betting odds will eventually become a commodity across platforms. Whether prediction markets are here to stay, the regulatory challenges ahead, and why Zack expects sportsbooks and prediction markets to ultimately converge into a similar user experience. How betting and prediction markets encourage probabilistic thinking, improve decision-making, and could reshape how people consume news and information. The growing "gamblification" of society, the impact of AI on entertainment and gambling, and why gambling education should become a much bigger priority. Why Zack believes the industry's biggest opportunity lies in creating customer-friendly products that emphasize long-term engagement over maximizing player losses. 4Casters' long-term vision, lessons learned from fundraising, and Zack's strategy for building a sustainable betting business designed for the next generation of sports bettors   ⚡️ Follow BoB on Twitter/X ⚡️ Watch BoB on Youtube ⚡️ Apply to be a guest here

On Episode 301 of the Business of Betting podcast, the tables are turned as Third Planet CEO Adam Small takes over hosting duties to interview Jeff Edelstein. Together, they reflect on the evolution of the U.S. sports betting industry since PASPA, debate prediction markets, discuss the future of gambling regulation, and explore why the industry's biggest challenges may still lie ahead. Hear them discuss: The rise and growing pains of the regulated U.S. sports betting market since PASPA was repealed Why higher tax rates, betting limits, and shifting regulation have changed the industry's outlook Looking back at the "gold rush" era of sports betting and whether those opportunities still exist Why community remains one of sports betting's biggest untapped opportunities, from live events to social experiences How DFS paved the way for products like PrizePicks, Kalshi, and prediction markets The ongoing debate over what qualifies as gambling versus financial trading Whether prediction markets can justify their soaring valuations and challenge established sportsbooks Why DraftKings, FanDuel, and other incumbents may still be best positioned to dominate if prediction markets expand The growing concern around gambling's influence on younger audiences and the need for gambling education in schools Jeff's predictions for where sports betting, prediction markets, and the broader gambling industry are headed over the next decade   ⚡️ Follow BoB on Twitter/X ⚡️ Watch BoB on Youtube ⚡️ Apply to be a guest here

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.   ⚡️ Follow BoB on Twitter/X ⚡️ Watch BoB on Youtube ⚡️ Apply to be a guest here

On this episode of the Business of Betting podcast, Jeff Edelstein is joined by John Aristotle Phillips, founder of PredictIt and CEO of Aristotle.  Hear them discuss: How PredictIt was founded and why prediction markets emerged as an alternative to traditional polling Why prediction markets could fundamentally change the way people think about risk, probability, and decision-making The future of sports prediction markets and why forecasting extends far beyond politics and sports How media companies, businesses, and consumers may use prediction markets as everyday forecasting tools The regulatory challenges facing prediction markets and why balanced oversight is essential for long-term growth Whether political prediction markets should be viewed as protected political speech rather than gambling The extraordinary story behind John's Princeton thesis demonstrating how an atomic bomb could be designed using publicly available information How John's passion for nuclear nonproliferation led him into politics and the creation of Aristotle, a leading political technology company The role AI could play in prediction markets and why human judgment will continue to matter John's vision for a future where prediction markets help guide everything from financial decisions and healthcare to everyday life     ⚡️ Follow BoB on Twitter/X ⚡️ Watch BoB on Youtube ⚡️ Apply to be a guest here

On this episode of the Business of Betting podcast, Jeff Edelstein sits down with ESPN sports betting reporter David Purdum to discuss the evolution of the betting industry, the rise of prediction markets, AI's impact on journalism, responsible gambling, and the integrity challenges shaping the future of sports wagering. Hear them discuss: David Purdum's journey from newspaper journalism to becoming ESPN's leading sports betting reporter How the sports betting industry has evolved from offshore books to legalization and today's prediction market era Why AI is becoming an essential tool for journalists and how it improves reporting and research The future of prediction markets and whether they can coexist with traditional sportsbooks The rise in betting integrity scandals and why player prop markets deserve closer scrutiny Responsible gambling, operator accountability, and the challenges of protecting vulnerable bettors Why gambling addiction is often called the "hidden addiction" and the unique risks it presents The need for gambling education in schools and whether the legal betting age should be increased How gambling mechanics are expanding beyond sportsbooks into prediction markets, collectibles, and gamified products David's approach to balancing a fast-paced reporting career with coaching youth soccer and maintaining perspective   ⚡️ Follow BoB on Twitter/X ⚡️ Watch BoB on Youtube ⚡️ Apply to be a guest here

On this episode of the Business of Betting Podcast, Jeff Edelstein sits down with Peter Hammon, gaming attorney and consultant at Vela Wood, to discuss prediction markets, exchange wagering, regulatory risk, and the legal battles that could shape the future of sports betting in America.    Hear them discuss: Why prediction markets have created a modern-day gold rush for operators, market makers, and investors looking to capitalize on a rapidly evolving opportunity The growing role of market makers and liquidity providers operating across sportsbooks, prediction markets, and international trading platforms How companies like Kalshi, Polymarket, Fanatics, Novig, and Sporttrade are positioning themselves for a future where prediction markets and sports betting increasingly overlap The legal and regulatory risks facing businesses operating across both state-regulated sportsbooks and federally regulated prediction markets Whether prediction markets have become too big to fail and why Peter believes the ultimate question centers on state versus federal authority over sports wagering Why Kalshi is emphasizing non-sports markets as it prepares for future legal and regulatory challenges The similarities between prediction markets, exchange wagering, poker, and peer-to-peer betting models, and why many of these concepts have existed for years under different names Peter’s journey into gaming law, from launching the UCLA Gaming Law Association to joining Smarkets and helping shape the early exchange wagering movement in the United States How Daily Fantasy Sports helped pave the way for PASPA’s repeal and fundamentally changed the trajectory of legal sports betting in America California’s ongoing sports betting stalemate, the leverage prediction markets may be giving tribal operators, and why the state's unique geography continues to shape the debate   ⚡️ Follow BoB on Twitter/X ⚡️ Watch BoB on Youtube ⚡️ Apply to be a guest here

On this episode of the Business of Betting Podcast, Jeff Edelstein sits down with Chris Dierkes, Head of Trading at Novig, to discuss exchange-based betting, prediction markets, bankroll management, and the future of the sports betting industry.    Hear them discuss: Why Chris believes betting exchanges provide better value for consumers through tighter pricing, lower fees, and increased flexibility The differences between traditional sportsbook cash-out features and exchange trading, and why bettors should understand the hidden costs involved Whether exchanges are actually safer and more consumer-friendly than sportsbooks despite the learning curve for new users Novig’s strategy for competing with prediction market leaders like Kalshi and Polymarket in an increasingly crowded marketplace The challenge of convincing recreational bettors to prioritize price and value over promotions, bonuses, and brand familiarity How Chris uses the Kelly Criterion to manage risk and determine position sizing when betting with significant edges The thought process behind placing million-dollar wagers and why bankroll management matters more than headline bet sizes Lessons learned from building a betting operation, scaling a bankroll, and overcoming the limitations imposed by traditional sportsbooks The regulatory uncertainty surrounding prediction markets and how potential Supreme Court involvement could shape the industry's future Why Chris chose to move from professional betting into exchange operations, and what he sees as the biggest opportunities ahead for market-based wagering   ⚡️ Follow BoB on Twitter/X ⚡️ Watch BoB on Youtube ⚡️ Apply to be a guest here

On this episode of the Business of Betting Podcast, Jeff Edelstein sits down with David Woodley, sports betting entrepreneur, investor, and advisor to companies including Edge Markets and Speed Labs, to share his perspective on prediction markets, gambling’s place in society, and the startups building the next generation of betting products.   Hear them discuss: Why gambling should be viewed more like alcohol, something most people can enjoy responsibly rather than through an all-or-nothing lens The rise of prediction markets, the regulatory battles surrounding them, and why younger founders are reshaping the industry David’s work with Edge Markets and how the company is reducing payment friction for bettors, sportsbooks, and prediction market traders The evolution of Speed Labs from a survivor pool game into a real-time prediction market platform powered by proprietary micro-market technology Why David believes betting “pick services” are often overrated, while niche businesses focused on solving one problem exceptionally well remain underrated The parallels between gambling, entrepreneurship, collectibles, investing, and other forms of risk-taking How gambling education could benefit from the same practical approach used for alcohol and financial literacy The opportunities and challenges facing startups building products around prediction markets and sports gaming Lessons learned from building, investing in, and advising companies across the betting ecosystem A lighthearted discussion on sports fandom, heartbreak, and why Vikings and Mets fans share a special bond     ⚡️ Follow BoB on Twitter/X ⚡️ Watch BoB on Youtube ⚡️ Apply to be a guest here