Business of Betting Podcast

Business of Betting Podcast

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. 1d ago

    E315 - Jake Pearson from ProPublica

    On this episode of the Business of Betting Podcast, Jeff Edelstein is joined by Jake Pearson, reporter at Pro Publica, to discuss his 10-week investigation into DraftKings’ responsible gambling practices. Jake explains how he tested sportsbook safeguards by escalating his betting behavior, what the experiment revealed about VIP programs and player protections, and why the industry needs greater transparency and accountability.   Hear them discuss: How Jake’s 10-week betting experiment tested DraftKings’ responsible gambling safeguards and led to a VIP invitation after a night of repeated loss-chasing. The findings from Pearson’s investigation, including the company’s responses to his betting patterns and the dispute over how many responsible gambling messages he received. The tension between sportsbook growth, VIP programs, and protecting high-value bettors who may also be at risk of gambling harm. Why responsible gambling interventions are difficult to design, including the role of betting patterns, player limits, cooling-off periods, and added friction. The challenges sportsbooks face under a fragmented state regulatory system while competing with prediction markets. Whether operators should face stronger expectations around advertising, customer retention, and identifying potentially harmful gambling behavior. How easier access to betting through mobile apps can make it harder for family members or operators to recognize escalating gambling problems. Why Jake and Edelstein believe gambling education should improve, particularly around expected value, parlays, and how betting products work. The need for more data on VIP customers, large losses, and the effectiveness of responsible gambling programs to inform better policy. Jake’s perspective on investigative journalism, industry accountability, and why the debate over responsible gambling protections is far from settled.     ⚡️ Follow BoB on Twitter/X ⚡️ Watch BoB on Youtube ⚡️ Apply to be a guest here

    E315 - Jake Pearson from ProPublica

  2. Oct 22

    E314 - Travis Geiger from WagerWire

    On this episode of the Business of Betting podcast, Jeff Edelstein is joined by Travis Geiger, Co-Founder and Chief Experience Officer of WagerWire, to discuss the company's expansion into international prediction markets, why it's avoiding the U.S. market for now, and how prediction markets could reshape the future of sports betting.  Hear them discuss: WagerWire's move into international prediction markets after securing Gibraltar's prediction market and gambling intermediary licenses, and why the company is targeting the UK and Mexico first. Why WagerWire is choosing to expand internationally rather than bet on the outcome of U.S. regulatory battles, and how its global rollout could inform a future U.S. launch. The difference between traditional betting exchanges and prediction markets, and how the latter have made betting on everything from economic outcomes to pop culture more accessible. How WagerWire plans to tailor its prediction markets to local cultures, using country-specific interests, trending topics, and new ways to gamify events. Why WagerWire is taking a compliance-first approach to international expansion, engaging regulators before launching rather than operating in gray markets. How WagerWire's original secondary market for sports bets connects with its new prediction market business, including plans to use international markets to price buyouts of domestic sportsbook bets. Travis's journey from UCLA film school and Hollywood to co-founding WagerWire, and how his frustration with traditional cash-out options and sports betting media inspired the company. How WagerWire uses AI to identify trending conversations, surface relevant markets, and turn long-form content into short clips, articles, and social posts while keeping much of its editorial production human-led. The importance of market integrity and responsible gambling, including using technology to identify potentially harmful behavior, intervene when necessary, and connect customers with professional support. Travis's vision for making gambling more consumer-friendly, why prediction markets need stronger education and guardrails for younger users, and how storytelling and community initiatives like WagerWire Cares can help the industry make a positive impact.   ⚡️ Follow BoB on Twitter/X ⚡️ Watch BoB on Youtube ⚡️ Apply to be a guest here

    E314 - Travis Geiger from WagerWire

  3. Oct 15

    E313 - Alex Keeney from Eventual

    On this episode of the Business of Betting Podcast, Jeff Edelstein is joined by Alex Keeney, Founder of Eventual, a video-first news and intelligence platform built around top prediction market traders. They discuss how Eventual turns political, economic, cultural, and technology signals into actionable insights, the growing prediction market industry, and potential betting opportunities ahead of the 2026 midterms and 2028 presidential election.   Hear them discuss: Alex’s unconventional career path through Hollywood, Capitol Hill, and working with Jordan Belfort and the lessons he carried into building Eventual. How Eventual uses insights from high-performing prediction market traders to help audiences understand what’s likely to happen and how to trade it. The growth of political prediction markets, why sports still dominates, and the untapped potential of markets tied to real-world events. How celebrity, retail sentiment, and differences between large traders and everyday participants can create pricing inefficiencies. The 2026 midterms, why Alex sees stronger signals favoring Democrats, and where he believes the obvious trading opportunities have already been priced in. Why qualitative signals—or “vibes”—such as candidate quality, voter conversations, and campaign behavior can complement polling and quantitative models. How prediction market traders are developing new edges through private polling, door-to-door canvassing, and cross-market arbitrage. The long-term opportunity for prediction markets to become more useful and accessible, along with Eventual’s plans for analytics, consulting, and B2B intelligence products. Why markets can be efficient over the long run while still presenting short-term opportunities when prices move on poor information. Alex’s long-shot political trades, including his case for Gina Hinojosa in Texas and a potential upset involving Victoria Spartz in Indiana.   ⚡️ Follow BoB on Twitter/X ⚡️ Watch BoB on Youtube ⚡️ Apply to be a guest here

    E313 - Alex Keeney from Eventual

  4. Oct 8

    E312 - Gina Fiore

    On this episode of the Business of Betting podcast, Jeff Edelstein is joined by Gina Fiore, professional advantage player and author of Advantage Player, to discuss her journey from blackjack dealer to professional gambler, the world of advantage play, and the story behind her new book and upcoming TV adaptation.   Hear them discuss: Gina’s childhood in Long Island, move to Nevada, and early pursuit of music before entering the casino world. How becoming a blackjack dealer and her mother’s suggestion to try card counting changed the direction of her career. Her transition into full-time advantage play and the competitive mindset that helped fuel her success. Being a woman in a male-dominated industry and how being underestimated became an advantage inside casinos. Teaching her son about card counting, probability, expected value, and why she wants him to understand gambling without becoming a gambler. Gina’s approach to risk and probability, including how her experience with advantage play influenced the way she viewed a 44% breast cancer risk. Her most memorable advantage-play stories, including beating Treasure Island badly enough that the casino changed its game conditions. The tight-knit advantage-play community, hole-card play, and the line between beating the house and getting casino employees in trouble. The realities of professional gambling, from bankroll swings and losing streaks to carrying large amounts of cash and treating money as a tool. The making of Advantage Player, her journey to a major publishing deal, the upcoming TV drama, and why she believes the book can reach far beyond the gambling audience   ⚡️ Follow BoB on Twitter/X ⚡️ Watch BoB on Youtube ⚡️ Apply to be a guest here

    E312 - Gina Fiore

  5. Oct 1

    E311 - Captain Jack Andrews

    On this episode of the Business of Betting podcast, Jeff Edelstein is joined by Captain Jack Andrews to discuss the evolution of advantage play, the rise of prediction markets, and the changing economics of sports betting. Hear them discuss: Captain Jack’s journey from private advantage player to a public voice in the gambling industry. How advantage play has evolved from card counting into a constantly changing landscape. The major “gold rushes” in gambling, from online casino bonuses and casino promotions to legalized sports betting. Why Captain Jack considers prediction markets the latest gold rush and how he is participating as a market maker. The growing competition among prediction-market makers and how it can create better prices for bettors. How supply, demand, order books, commissions, and competition shape prediction-market pricing. The rise of sports-focused prediction markets and the opportunities emerging beyond the biggest platforms. The legal debate surrounding prediction markets, gambling, the Wire Act, and potential regulatory changes. The growing pervasiveness of gambling, responsible gambling, AI, regulation, and the need for better consumer education. Captain Jack’s views on probabilistic thinking, the personal costs of a gambling career, and some of his most memorable advantage-play stories.   ⚡️ Follow BoB on Twitter/X ⚡️ Watch BoB on Youtube ⚡️ Apply to be a guest here

    E311 - Captain Jack Andrews

  6. Sep 24

    E310 - Justin Herzig from PredictQ

    On this episode of the Business of Betting podcast, Jeff Edelstein is joined by Justin Herzig, Co-founder of PredictQ, to discuss his journey from DFS and fantasy sports to prediction markets and his approach to finding new edges as markets evolve. Hear them discuss: Justin’s evolution from Yahoo fantasy leagues and DFS to Best Ball, showdown formats, simulations, and prediction markets. How he identifies new opportunities, finds emerging edges, and knows when it’s time to move on from a market. PredictQ’s mission to provide prediction-market content, tools, research, community, and price discovery for traders. Why prediction markets still offer opportunities in niche and less-liquid markets despite sophisticated market makers. The learning curve around prediction markets, including pricing, fees, liquidity, order books, and market-making versus market-taking. Justin’s record of five consecutive Best Ball Mania finals and how portfolio diversification helped him manage variance and injuries. Why he believes DFS has become more stagnant as prediction markets and other betting products attract more attention and marketing investment. The future of sports prediction markets, including potential regulatory changes and the need for clearer rules around certain markets. How PredictQ aims to combine the community and educational elements of DFS platforms with market discovery, research, price comparison, and eventually direct trading. Justin’s approach to finding edges in prediction markets, using his own trades and models to develop new tools while continuing to adapt as the market matures.   ⚡️ Follow BoB on Twitter/X ⚡️ Watch BoB on Youtube ⚡️ Apply to be a guest here

    E310 - Justin Herzig from PredictQ

  7. Sep 17

    E309 - Karl Whelan

    On this episode of the Business of Betting Podcast, Jeff Edelstein is joined by Professor Karl Whelan, Professor of Economics at University College Dublin and author of Fine Margins: How Economics Explains Sports Betting.   Hear them discuss: How Karl went from macroeconomics to researching the economics behind sports betting. What bookmakers got right about home-field advantage when sports returned after COVID. Why betting odds are designed to maximize sportsbook profits rather than simply reflect the “truth.” The favorite-longshot bias and why longshot bets tend to produce worse returns for bettors. Why NBA and MLB markets are notable exceptions to the favorite-longshot bias. Why unders are generally priced more favorably than overs, particularly in player props. The economics behind parlays and why single-game parlays can be especially profitable for sportsbooks. How Karl’s research into Kalshi and prediction markets reveals opportunities, pricing inefficiencies, market makers, and the impact of fees. Why sports betting markets function much like financial markets and how they aggregate information. How AI is transforming Karl’s research, data analysis, backtesting, and the way he teaches economics and sports betting.     ⚡️ Follow BoB on Twitter/X ⚡️ Watch BoB on Youtube ⚡️ Apply to be a guest here

    E309 - Karl Whelan

  8. Sep 10

    E308 - Sean Green from Sports Gambling Podcast Network

    On this episode of the Business of Betting Podcast, Jeff Edelstein is joined by Sean Green, co-founder and host of the Sports Gambling Podcast Network (SGPN), to discuss how a passion project that started with two friends picking NFL games grew into one of the longest-running independent sports betting media companies. Sean shares lessons on authenticity, audience building, monetization, independence, comedy, and taking the leap from Hollywood to full-time entrepreneurship. Hear them discuss: How Sean Green and Ryan Kramer launched the Sports Gambling Podcast in 2011, long before sports betting became a mainstream media business. How steady growth and expansion into new sports transformed a simple NFL podcast into the Sports Gambling Podcast Network. Why authenticity has been central to SGPN's success and how audiences can tell the difference between genuine bettors and those simply chasing industry trends. How SGPN adapted during the COVID-19 sports shutdown by creating simulated games and betting content that helped strengthen its audience and community. Why the company has never sold picks, instead focusing on free content, advertising, sponsorships, and building long-term trust with its audience. How the post-PASPA sports betting boom changed the content landscape and why many gambling media competitors have struggled as sportsbook marketing budgets tightened. Why SGPN has remained independent despite acquisition interest and how operating lean has allowed the company to maintain control over its future. Sean's decision to leave his career as a Hollywood TV writer in 2019 and take the leap into full-time entrepreneurship. Why comedy and entertainment are essential to SGPN's content strategy, along with Sean's memorable $200,000 DFS score and his thoughts on the changing DFS landscape. Sean's advice for aspiring sports betting content creators on finding an authentic angle, staying passionate, and consistently giving audiences a reason to return.   ⚡️ Follow BoB on Twitter/X ⚡️ Watch BoB on Youtube ⚡️ Apply to be a guest here

    E308 - Sean Green from Sports Gambling Podcast Network
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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
    317
  • Rating
    Explicit
  • Copyright
    © Copyright 2025
  • Show Website
    Business of Betting Podcast

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