Business of Betting Podcast

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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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

 

 

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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

 

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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

 

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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

 

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