Business of Betting Podcast

Business of Betting Podcast
  • 4.6 (56)
  • Sports
  • Updated Weekly

A podcast covering the sports betting industry from the perspective of bettors, operators, and industry insiders. Hosted by Jeff Edelstein, Senior Analyst at InGame.com.

  1. 5d ago

    E300 - Dave Portnoy from Barstool Sports

    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

  2. Jul 9

    E299 - John Phillips from PredictIt

    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

    E299 - John Phillips from PredictIt

  3. Jul 2

    E298 - David Purdum from ESPN

    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

    E298 - David Purdum from ESPN

  4. Jun 25

    E297 - Peter Hammon

    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

    E297 - Peter Hammon

  5. Jun 18

    E296 - Chris Dierkes from Novig

    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

    E296 - Chris Dierkes from Novig

  6. Jun 11

    E295 - David Woodley from SpeedLabs

    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

    E295 - David Woodley from SpeedLabs

  7. Jun 4

    E294 - Alfonso Straffon from Matchbook Betting Exchange

    On this episode of the Business of Betting Podcast, Jeff Edelstein sits down with Alfonso Straffon to discuss his journey from Costa Rica’s offshore sportsbook boom to Wall Street bond trading and back into sports betting through the rise of prediction markets.   Hear them discuss: Alfonso’s unique career path through offshore sportsbooks, finance, equity research, and prediction markets The evolution of sports betting from credit bookmakers and offshore operators to online, mobile, and in-play betting How PASPA changed the industry and reshaped the future of offshore sportsbooks Why Matchbook believes sports prediction markets and betting exchanges can thrive alongside traditional sportsbooks The similarities between financial markets, bond trading, sports betting, and prediction market price discovery The opportunities and regulatory risks facing prediction markets in the United States How operators like DraftKings, FanDuel, Kalshi, and Matchbook may compete in the next phase of market evolution The impact prediction markets are having on offshore sportsbooks and betting behavior in unregulated states Why Alfonso believes exchange-style betting offers better economics and longevity for bettors His vision for Matchbook’s U.S. launch and the future of sports-focused prediction   ⚡️ Follow BoB on Twitter/X ⚡️ Watch BoB on Youtube ⚡️ Apply to be a guest here

    E294 - Alfonso Straffon from Matchbook Betting Exchange

  8. May 29

    E293 - Matt Kalish

    On this episode of the Business of Betting Podcast, Jeff Edelstein sits down with Matt Kalish, co-founder of DraftKings and founder of Hardscope, to discuss his public criticism of Kalshi, the risks of exchange-style betting products, and why he believes prediction markets are being marketed incorrectly to everyday consumers.   Hear them discuss: Why Matt’s first experience betting on Kalshi triggered concerns about pricing, liquidity, and customer transparency The wager that sparked his deep dive into prediction market mechanics How exchange-style betting differs from traditional sportsbook experiences Why Matt believes retail users are competing against sophisticated Wall Street market makers and API traders The ethical concerns around marketing prediction markets as “easy” or beatable for everyday users Lessons DraftKings learned from the early daily fantasy sports boom and regulatory backlash The similarities and differences between DFS-era marketing and today’s prediction market messaging Why Matt believes companies should clearly position these products as financial markets—not casual sports betting apps Concerns around transparency, enforcement, wash trading, and market surveillance How traditional sportsbooks and state regulators may respond to prediction markets moving forward Why operators like DraftKings and FanDuel can’t afford to ignore the prediction market space Matt’s perspective on consumer product DNA versus Wall Street infrastructure culture Why he believes recreational bettors prioritize entertainment and trust over pure trading mechanics The future of creator-led marketing and why gambling companies still haven’t mastered the creator economy Matt’s transition from DraftKings into building Hardscope and his interest in digital media and creator platforms   ⚡️ Follow BoB on Twitter/X ⚡️ Watch BoB on Youtube ⚡️ Apply to be a guest here

    E293 - Matt Kalish
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4.6
out of 5
56 Ratings

About

A podcast covering the sports betting industry from the perspective of bettors, operators, and industry insiders. Hosted by Jeff Edelstein, Senior Analyst at InGame.com.

Information

  • Creator
    Business of Betting Podcast
  • Years Active
    2017 - 2026
  • Episodes
    302
  • Rating
    Explicit
  • Copyright
    © Copyright 2025
  • Show Website
    Business of Betting Podcast

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