Business of Betting Podcast

On this episode of the Business of Betting Podcast, Jeff Edelstein is joined by Adam Levitan, Co-founder of Establish The Run, to discuss the evolution of DFS, building durable betting media businesses, and what it really takes to maintain an edge in a competitive gambling landscape. Hear them discuss: 00:00 – Lifestyle shifts, Colorado living, and opening banter 02:40 – Adam’s early career at Rotoworld and the founding of Established The Run 05:45 – Building ETR as a business: scalability, partnerships, and key-man risk 07:30 – The DFS boom, legacy media missteps, and leaving NBC 10:30 – DFS longevity, legality, and comparisons to poker ecosystems 13:45 – Content strategy, niche audiences, and the rise of solo pods 17:15 – Tournament vs. cash play and setting realistic bettor expectations 20:45 – Staying competitive: data investment, modeling, and hiring elite talent 25:00 – Parenting, gambling conversations, and work–life balance 31:00 – Sustainability, identity, and long-term thinking in betting and business   ⚡️ Follow BoB on Twitter/X ⚡️ Watch BoB on Youtube ⚡️ Apply to be a guest here --- This podcast is presented by Optimove, the #1 CRM Marketing solution for the iGaming industry. Since 2012, Optimove has served iGaming Operators from startups to industry leaders. Today, 4 out of the Top 5 US Operators Personalize Player Experiences with Optimove. iGaming operators know their growth journey begins and continues with Optimove, the #1 CRM Marketing solution for the iGaming industry. 

On this year-end episode of the Business of Betting Podcast, host Jeff Edelstein is joined by Adam Small, Co-Founder of Third Planet Media. Adam shares candid insights into the evolution of affiliate marketing, the challenges facing media and SEO-driven businesses, and why Costa Rica holds a special place in his heart. Hear them discuss: 01:00 – Adam Small’s background, his role at Third Planet, and joining the Business of Betting Podcast for the first time 02:30 – The current state of affiliate marketing and how the model has changed dramatically over the past decade 04:30 – Fragmentation in U.S. gambling media: regulated markets, sweepstakes, prediction markets, and offshore resurgence 06:30 – Why SEO and search traffic are becoming less reliable and what that means for media businesses 08:30 – Lessons from building PocketFives with $50 and why that era of affiliate marketing is gone 10:30 – Why modern gaming media companies must diversify beyond pure affiliate revenue 12:30 – Expansion strategies: tools, horizontal growth, and why major affiliates are moving beyond traditional models 15:00 – The rapid rise of InGame and why high-quality, trusted reporting filled a critical industry gap 18:00 – Building credibility in gambling journalism and earning trust from operators, regulators, and executives 21:00 – Adam’s entrepreneurial origin story, PocketFives, trivia nights, poker, and founding a company with friends 25:00 – The importance of relationships, networking, and long-term reputation in the gambling industry 28:00 – The reality of bad actors in gaming and hard lessons learned about trust in business 31:00 – Media independence vs. advertiser influence and why smaller outlets face unique pressures 35:00 – Costa Rica culture, relationships, and why the country leaves such a lasting impression 39:00 – Balancing business ambition, family life, and future plans across the U.S. and Costa Rica 41:00 – What’s next for Third Planet, lessons from working at a public company, and building for long-term impact   ⚡️ Follow BoB on Twitter/X ⚡️ Watch BoB on Youtube ⚡️ Apply to be a guest here --- This podcast is presented by Optimove, the #1 CRM Marketing solution for the iGaming industry. Since 2012, Optimove has served iGaming Operators from startups to industry leaders. Today, 4 out of the Top 5 US Operators Personalize Player Experiences with Optimove. iGaming operators know their growth journey begins and continues with Optimove, the #1 CRM Marketing solution for the iGaming industry. 

On this episode of the Business of Betting Podcast, Jeff Edelstein is joined by Zaire Williams, founder of Exclusive, on-the-ground acquisition specialist, and one of the most unique new-age affiliate operators working at the intersection of sports betting, influencer marketing, and experiential events. Hear them discuss: 01:00 – How Zaire built a “new-age affiliate” using influencer content, live events, and face-to-face education to drive signups and why SEO isn’t part of their playbook. 02:00 – Why operators aren’t getting many new sportsbook users in 2025, and how Exclusive now converts bettors into social sportsbooks, sweepstakes, and research platforms. 03:00 – How Zaire’s first company used ambassadors in bars to walk people through KYC, and why operators pushed back ultimately leading to a more educational, higher-LTV model. 04:45 – Why older generations underestimate the power of creators, and how young bettors treat betting like everyday entertainment instead of gambling. 06:00 – Zaire break down how Roblox, gaming loot boxes, online marketplaces, and digital culture primed younger users to treat betting like another fun digital activity. 07:30 – Why loyalty programs don’t resonate, why parlays work as social currency, and how small rewards (like Starbucks or Sephora credits) could outperform massive bonuses. 09:30 – Micro-rewards, creator-led education, and loyalty designed around lifestyle not casino comps or high-roller incentives. 11:00 – Zaire discusses being one of the few Black operators in the space, how that became a superpower, and why diverse teams outperform in creator-driven ecosystems. 14:00 – About Jersey food, neighborhood culture, and how the state’s mix of communities prepares people to thrive in gaming. 16:00 – A breakdown of their playbook: creators, experiential events, education-focused onboarding, and targeted influencer content. 18:00 – From “I already have all the apps” to past negative experiences and how education, better tools, and improved UX reduce barriers. 20:00 – Why PolyMarket and Kalshi are becoming top priorities, and how Exclusive is positioning itself for U.S. elections, World Cup, and broader entertainment wagering. 22:00 – How Exclusive plans to grow with the industry: entertainment-first betting, creator ecosystems, and product education that goes beyond acquisition.   ⚡️ Follow BoB on Twitter/X ⚡️ Watch BoB on Youtube ⚡️ Apply to be a guest here --- This podcast is presented by Optimove, the #1 CRM Marketing solution for the iGaming industry. Since 2012, Optimove has served iGaming Operators from startups to industry leaders. Today, 4 out of the Top 5 US Operators Personalize Player Experiences with Optimove. iGaming operators know their growth journey begins and continues with Optimove, the #1 CRM Marketing solution for the iGaming industry. Get your first month free: https://optimove.com/businessofbetting

On this episode of the Business of Betting Podcast, Jeff Edelstein is joined by legendary oddsmaker and gambling industry icon Roxy Roxborough to reflect on his career, the evolution of sports betting, and where the industry is headed next.   Hear them discuss: 01:00 - Roxy’s introduction and early memories of gambling culture 03:00 - How racetracks and pool halls shaped the early gambling ecosystem 07:30 - Building Las Vegas Sports Consultants and making odds for the world 12:30 - The rise of technology, computers, and early data-driven betting models 16:00 - Post-PASPA sports betting: what Roxy got right, what he got wrong 20:00 - Why FanDuel and DraftKings dominated—and legacy operators got left behind 24:00 - Prediction markets, taxation surprises, and what bettors don’t see coming 28:00 - Match fixing, integrity concerns, and whether gambling problems are truly new 31:00 - The gambler’s mindset and how it impacts real-life decision making 34:00 - Fashion, legacy, and lessons learned from a lifetime in betting 37:00 - Final thoughts on regulation, education, and the future of the industry   ⚡️ Follow BoB on Twitter/X ⚡️ Watch BoB on Youtube ⚡️ Apply to be a guest here --- This podcast is presented by Optimove, the #1 CRM Marketing solution for the iGaming industry. Since 2012, Optimove has served iGaming Operators from startups to industry leaders. Today, 4 out of the Top 5 US Operators Personalize Player Experiences with Optimove. iGaming operators know their growth journey begins and continues with Optimove, the #1 CRM Marketing solution for the iGaming industry. Get your first month free: https://optimove.com/businessofbetting

On this episode of the Business of Betting Podcast, Jeff Edelstein is joined by Bill Miller, CEO of the American Gaming Association, for a deep dive into prediction markets, federal vs. state authority, industry fragmentation, and the future of U.S. gambling policy. Hear them discuss: 01:00 – Bill’s journey to the AGA, his background at the Business Roundtable and U.S. Chamber of Commerce, and how he entered the gaming industry on the same day the Wire Act was reinterpreted 02:00 – The rapid rise of prediction markets, how CFTC involvement blindsided the industry, and why AGA sees loophole-based models as regulatory threats similar to skill games and sweepstakes 04:30 – The internal tensions leading to DraftKings, FanDuel, and Fanatics leaving the AGA, and why licensed operators joining prediction markets created an irreconcilable conflict with AGA’s mission 07:00 – Why offering sports contracts not elections or Oscars is what triggered the regulatory showdown, and how state regulators view the integrity of approved betting menus 08:30 – Industry fragmentation: the rise of new trade groups (Sports Betting Alliance & Coalition for Prediction Markets), how CEOs face shareholder pressure, and whether reunification is possible 11:00 – The legal battle ahead: federalism, states’ rights, tribal sovereignty, and why the AGA expects the dispute to reach the Supreme Court 14:00 – How prediction markets could undermine tribal exclusivity (e.g., Florida), state budgets, and federally recognized regulatory authority 18:00 – The “One Big Beautiful Bill,” why the AGA supported it, and how the late-added 90% loss deduction rule blindsided the industry—and the bipartisan effort underway to reverse it 24:00 – Bill’s experience representing Fortune 500 CEOs and how those relationships helped modernize cashless payments and banking integrations for casinos 29:00 – Texas & California outlooks: entrenched political roadblocks, tribal dynamics, and whether prediction markets could actually unify tribal interests 33:00 – G2E’s growth, what exhibitors really want, and how AGA navigates pre-show vs. on-floor engagement in the largest gaming conference in the world 37:00 – Bill on being a gambler, his favorite games (craps, blackjack, roulette), and why 2026 will be one of the most consequential years in gaming policy   ⚡️ Follow BoB on Twitter/X ⚡️ Watch BoB on Youtube ⚡️ Apply to be a guest here --- This podcast is presented by Optimove, the #1 CRM Marketing solution for the iGaming industry. Since 2012, Optimove has served iGaming Operators from startups to industry leaders. Today, 4 out of the Top 5 US Operators Personalize Player Experiences with Optimove. iGaming operators know their growth journey begins and continues with Optimove, the #1 CRM Marketing solution for the iGaming industry. Get your first month free: https://optimove.com/businessofbetting