Business of Betting Podcast

E277 - Danny Funt

On this episode of the Business of Betting Podcast, Jeff Edelstein is joined by Danny Funt, journalist and author of Everybody Loses: The Tumultuous Rise of American Sports Gambling, for an in-depth conversation on the legalization of sports betting, industry incentives, responsible gambling, and how betting is reshaping sports culture.
 
Hear them discuss:
00:00 – Danny’s background covering sports betting, the origins of Everybody Loses, and why he wanted to avoid writing a one-sided hit piece on the industry
03:00 – The historical context behind legalized sports betting, from early league opposition to the post-PASPA explosion
06:00 – Reporting challenges, access issues, and which major operators and leagues declined to participate in the book
08:00 – VIP bettors, sportsbook incentives, and why a small group of customers drives a disproportionate share of industry revenue
11:00 – Sports betting, cultural gamification, and concerns around youth exposure and normalization
15:00 – Responsible gambling efforts inside sportsbooks and what surprised Danny most during his reporting
19:00 – Team partnerships, exclusive VIP perks, and how access to sports experiences is used to retain high-value bettors
22:00 – Where the industry is making progress, including funding for treatment and counseling
24:00 – Prediction markets, DFS parallels, and the regulatory gray areas creating friction with lawmakers
28:00 – How betting changes fandom, emotional investment, and the way fans experience sports
31:00 – Industry reaction to the book, media framing, and what Danny hopes comes next for sports betting regulation
 
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E276 - Adam Chernoff

On this episode of the Business of Betting Podcast, Jeff Edelstein is joined by Adam Chernoff, sports betting analyst and founder of adamchernoff.com, for a wide-ranging conversation on betting markets, media, content, and where value still exists in an increasingly efficient ecosystem.
 
Hear them discuss:
00:00 – Adam’s unconventional career path across betting, media, casino operations, and content creation, and why labels don’t fully capture his role in the industry
05:00 – How betting markets have evolved over the past decade, why edges are harder to find, and what that means for modern bettors
09:30 – The growing influence of narrative, media personalities, and public perception on betting lines and market movement
14:00 – Why information is no longer the advantage it once was, and how execution and discipline now matter more than raw insight
18:30 – Content vs. betting: how Adam thinks about building trust with an audience without selling false certainty or hype
22:30 – The role of technology, data, and automation in betting, and where human judgment still outperforms models
26:00 – Why most bettors misunderstand bankroll management, risk tolerance, and long-term sustainability
30:00 – Adam’s perspective on prediction markets, pricing efficiency, and whether they truly threaten traditional sportsbooks
34:00 – Media incentives, engagement-driven content, and the tension between education and entertainment
38:00 – What Adam would focus on today if he were starting over in the betting industry
 
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E275 - John Gordon from Incentive Games

On this episode of the Business of Betting Podcast, Jeff Edelstein is joined by John Gordon, Founder & CEO of Incentive Games, for a deep dive into free-to-play gaming, behavioral science, and why engagement—not acquisition—is becoming the most valuable currency in modern iGaming. 
 
Hear them discuss:
00:00 – John’s background in chemical engineering and how an analytical mindset shaped his approach to gaming and product design
02:30 – Buying and running a fifth-division football club in Cyprus and the surprising parallels between sports ownership and gaming
05:00 – The origins of Incentive Games and how an early fantasy betting concept evolved into a global free-to-play platform
07:00 – The psychology behind free-to-play games: motivation, habit formation, and why engagement beats bonuses
09:30 – Responsible gaming, regulation, and why free-to-play products can support safer player behavior
11:30 – Expanding into real-money games, including crash and arcade-style formats
14:00 – Why retention and engagement drive more long-term value than aggressive acquisition strategies
16:00 – How Incentive Labs uses data, cadence, and timing to optimize player experiences
18:00 – High-value players vs. bonus abusers and why free-to-play resonates with VIP audiences
20:00 – Innovation gaps in iGaming and where John believes the next big opportunities lie
24:00 – Personalization, volatility preferences, and the future of engagement-led game design
 
 
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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. 

E274 - Derek Stevens from Circa Resort & Casino

On this episode of the Business of Betting Podcast, Jeff Edelstein is joined by Derek Stevens, Owner & CEO of Circa Resort & Casino, for a wide-ranging conversation on building one of Las Vegas’ most distinctive properties, the evolution of sports betting, the explosion of Circa Survivor, and why prediction markets pose an existential threat to state-regulated gaming.Hear them discuss:00:00 – Fremont Street’s resurgence, Circa’s role in downtown Vegas, and designing an elevated experience beyond hotel guests04:30 – Vegas history, Steve Wynn’s influence, and why the Mirage changed casino design forever09:00 – Stadium Swim skepticism, why investors doubted it, and how it became Circa’s signature attraction11:00 – Derek’s unlikely path from Michigan manufacturing to casino ownership and the family business roots behind it15:00 – The Stevens brothers’ partnership, division of responsibilities, and why it’s worked for decades17:00 – Circa Sports’ expansion into online betting, proprietary technology, and choosing where the model actually fits20:00 – State tax revenue, problem gambling funding, and why prediction markets undermine the regulated ecosystem22:00 – DraftKings, FanDuel, and Fanatics entering prediction markets and why Derek believes it puts future licenses at risk23:30 – The origin story of Circa Million and Circa Survivor and how Survivor became lightning in a bottle25:00 – Circa Survivor’s growth to a $18.7M prize pool, five perfect entries, and why the contest resonates emotionally27:30 – Derek’s pitch for Circa: sunshine, Stadium Swim year-round, best-in-class rooms, and real value in Vegas
 
 
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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. 

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