Business of Betting Podcast

E273 - Adam Levitan from Establish The Run

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 banter02:40 – Adam’s early career at Rotoworld and the founding of Established The Run05:45 – Building ETR as a business: scalability, partnerships, and key-man risk07:30 – The DFS boom, legacy media missteps, and leaving NBC10:30 – DFS longevity, legality, and comparisons to poker ecosystems13:45 – Content strategy, niche audiences, and the rise of solo pods17:15 – Tournament vs. cash play and setting realistic bettor expectations20:45 – Staying competitive: data investment, modeling, and hiring elite talent25:00 – Parenting, gambling conversations, and work–life balance31:00 – Sustainability, identity, and long-term thinking in betting and business
 
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---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. 

E272 - Adam Small from Third Planet Media

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 time02:30 – The current state of affiliate marketing and how the model has changed dramatically over the past decade04:30 – Fragmentation in U.S. gambling media: regulated markets, sweepstakes, prediction markets, and offshore resurgence06:30 – Why SEO and search traffic are becoming less reliable and what that means for media businesses08:30 – Lessons from building PocketFives with $50 and why that era of affiliate marketing is gone10:30 – Why modern gaming media companies must diversify beyond pure affiliate revenue12:30 – Expansion strategies: tools, horizontal growth, and why major affiliates are moving beyond traditional models15:00 – The rapid rise of InGame and why high-quality, trusted reporting filled a critical industry gap18:00 – Building credibility in gambling journalism and earning trust from operators, regulators, and executives21:00 – Adam’s entrepreneurial origin story, PocketFives, trivia nights, poker, and founding a company with friends25:00 – The importance of relationships, networking, and long-term reputation in the gambling industry28:00 – The reality of bad actors in gaming and hard lessons learned about trust in business31:00 – Media independence vs. advertiser influence and why smaller outlets face unique pressures35:00 – Costa Rica culture, relationships, and why the country leaves such a lasting impression39:00 – Balancing business ambition, family life, and future plans across the U.S. and Costa Rica41:00 – What’s next for Third Planet, lessons from working at a public company, and building for long-term impact
 
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---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. 

E271 - Zaire Williams from Exclusive

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.
 
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---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

E270 - Roxy Roxborough

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
 
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---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

E269 - Bill Miller from American Gaming Association

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 reinterpreted02:00 – 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 sweepstakes04:30 – 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 mission07:00 – Why offering sports contracts not elections or Oscars is what triggered the regulatory showdown, and how state regulators view the integrity of approved betting menus08:30 – Industry fragmentation: the rise of new trade groups (Sports Betting Alliance & Coalition for Prediction Markets), how CEOs face shareholder pressure, and whether reunification is possible11:00 – The legal battle ahead: federalism, states’ rights, tribal sovereignty, and why the AGA expects the dispute to reach the Supreme Court14:00 – How prediction markets could undermine tribal exclusivity (e.g., Florida), state budgets, and federally recognized regulatory authority18:00 – 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 it24:00 – Bill’s experience representing Fortune 500 CEOs and how those relationships helped modernize cashless payments and banking integrations for casinos29:00 – Texas & California outlooks: entrenched political roadblocks, tribal dynamics, and whether prediction markets could actually unify tribal interests33:00 – G2E’s growth, what exhibitors really want, and how AGA navigates pre-show vs. on-floor engagement in the largest gaming conference in the world37:00 – 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
 
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---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

E268 - Shawn Fluharty

On this episode of the Business of Betting Podcast, Jeff Edelstein is joined by Shawn Fluharty, West Virginia Delegate, President of NCLGS, and Head of Government Affairs at Play’n GO to break down the rapidly shifting U.S. gambling landscape, from prediction markets to sweepstakes crackdowns to the political realities shaping iCasino expansion.
 
Hear them discuss:
01:00 – Shawn’s path from journalism student to West Virginia legislator and the surprising way he ended up in gaming policy
03:00 – How West Virginia became an early adopter of sports betting and iCasino, and why integrity fees failed before they even started
05:00 – Why gaming policy remains bipartisan and how lawmakers think about consumer protection, revenue, and political optics
07:00 – The sweepstakes industry crackdown: why states view it as revenue leakage and why the model was always doomed
09:00 – Prediction markets, CFTC authority, and why Shawn believes the issue is heading toward the Supreme Court
12:00 – The danger of loophole-based gambling models and how regulators evaluate “if it walks like a duck…” arguments
14:00 – iCasino progress: which states are closest to legalizing next, and why education gaps stall legislative momentum
17:00 – The post-PASPA state-federal balance: who actually controls the future of U.S. gambling policy?
19:00 – Responsible gambling oversight, the shrinking gray market, and parallels between sweepstakes and historical horse racing
21:00 – The future of prediction markets, what happens if they scale, and whether they can coexist with casino-style outcomes
 
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---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

E267 - Adam Kaplan from Astralis Capital Management

On this episode of the Business of Betting Podcast, Jeff Edelstein is joined by Adam Kaplan, investor, operator, and long-time industry strategist working at the intersection of sports betting, DFS, prediction markets, and emerging gaming products.Hear them discuss:01:00 – How the pace of innovation since PASPA has completely reshaped the gaming landscape02:00 – DraftKings & FanDuel’s decision to leave the AGA, what it signals, and why prediction markets are forcing operators to redraw alliances03:15 – How big operators approach new products: build, buy, undermine… then build anyway and why speed now separates winners from laggards04:50 – Who becomes dominant in prediction markets: PolyMarket, Kalshi, DraftKings, FanDuel, Robinhood and the power of cross-sell advantages06:45 – Why everyone is entering prediction markets despite lower CAC/LTV economics and why public companies can’t afford to sit out08:45 – Why land-based casino operators are staying away, and which companies are best positioned to launch direct-to-consumer prediction products10:30 – Testing the boundaries: whether prediction markets will push into casino-style propositions and how regulators might respond12:00 – The big question: Do prediction markets survive the courts? Will the fight reach the Supreme Court? What operators must hedge for.13:30 – How investor pressure, stock performance, and regulatory risk are forcing operators to move quickly  even without clarity on legality16:00 – What PrizePicks could mean for U.S. market share, innovation cycles, and the next phase of digital gaming competition18:50 – Emerging innovations bubbling under the surface: new gaming categories, regulatory interpretations, and tech-driven product shifts20:15 – What the next 5–10 years might look like: consolidation vs. vertical specialization, crypto-integrated markets, and where Robinhood could disrupt the most
 
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---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

E266 - Pierre Lindh from Next.io

On this episode of the Business of Betting Podcast, Jeff Edelstein is joined by Pierre Lindh, Co-Founder and Managing Director of Next.io, for a wide-ranging conversation recorded live at G2E Las Vegas.Hear them discuss:00:00 – How Pierre began running a 150-player underground poker club at age 1503:50 – The 2006 police raid that made national headlines and launched his gaming career05:45 – Swedish poker culture, card-playing heritage, and why Texas Hold’em spread so quickly09:00 – How live poker culture changed from social gatherings to headphones and sunglasses12:00 – Building Next.io: 800+ global events and designing conferences for every personality type15:00 – Why Malta became the world’s online-gambling capital19:00 – Why Pierre’s identity is inseparable from Next.io and how he thinks about entrepreneurship27:00 – The future of gambling: prediction markets, sweeps, skill games, and U.S. creativity28:40 – The shrinking global gray market: why operators must choose regulated or unregulated paths30:00 – Why the U.S. is brutally competitive and only a few operators can thrive32:00 – Cultural differences in loyalty, trust, and brand adoption in gambling markets36:40 – Closing thoughts from the G2E show floor
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---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

E265 - Drew Tabor from Ungambled

On this episode of the Business of Betting Podcast, Jeff Edelstein is joined by Drew Tabor, Founder of Ungambled, to break down the evolving world of bonus farming, account profiling, and how sharp bettors gain long-term edges in the modern U.S. sportsbook landscape.Hear them discuss:01:00 – Drew’s early background, from finishing every math class in his state to becoming the world’s #1 ranked Guitar Hero player and how that discipline shaped his entrepreneurial journey03:00 – The origin story of Ungambled and why sharp bettors needed a more systematic way to bonus hedge and extend the lifespan of partner accounts05:00 – How the Ungambled app deliberately violates sharp-betting heuristics to profile accounts as “high-limit squares”07:00 – The logic behind hedging bonuses, manipulating CLV signals, and timing-based strategies that minimize detection08:00 – Why female accounts statistically receive higher bonuses and how users scale earnings through partner accounts09:00 – Building “aggressive bonus farming” systems that generate $10–$20K in two months and how VIP programs expand opportunity12:00 – The future of Ungambled: hedging multi-book parlays, advanced modeling, and automation designed to scale14:00 – The business philosophy of leverage software, capital, people, and one-to-many systems and how it informs Drew’s long-term vision17:00 – Prediction markets, crypto casinos, and whether bonuses shrink or sustain as the industry matures19:00 – Why Drew rarely bets recreationally anymore and why same-game parlays still hold a soft spot for him
 
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---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

E264 - Bernard Marantelli from White Swan Data

On this episode of the Business of Betting Podcast, Jeff Edelstein is joined by Bernard Marantelli, Founder of White Swan Data and Colossus Bets, to discuss his entrepreneurial journey, the evolution of pool betting, and what innovation looks like in a changing global gaming landscape.Hear them discuss:01:00 – Bernard’s background growing up in a family of bookmakers and how that shaped his career in data, biotech, and gambling02:00 – The Texas Lottery caper: why a 2023 jackpot became +EV, how Bernard’s team bought 25M+ tickets, and the massive logistical hurdles they overcame05:00 – The math behind beating a state lottery, from permutations to public participation to splitting risk across millions of tickets10:30 – What it actually looks like to print, store, and organize millions of physical lottery slips (including hiring an Uber driver on the spot)15:00 – Introducing iBankroll: why crypto casinos have a liquidity and credibility problem and how his company underwrites VIP risk17:00 – Understanding “Black Swan” risk for high-stakes casino action and why decentralized bankrolls reduce catastrophic exposure22:00 – Why crypto casinos are growing fast globally as regulated markets tighten KYC, RG, and deposit limits24:30 – Bernard’s candid take on prediction markets, their regulatory uncertainty, and why the economics, not politics, may determine who survives30:00 – Lessons from a lifetime in gambling: building edge, information, diversification, and the constant search for expected value38:00 – Why opportunities are cyclical, why secrecy isn’t always the winning strategy, and why the next “Texas moment” is unlikely under modern rules
 
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---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