E259 - Gadoon “Spanky” Kyrollos

On this episode of the Business of Betting Podcast, Jeff Edelstein is joined by Isaac Rose Berman, gambling policy fellow, writer, and bettor, for an in-depth conversation on youth exposure to gambling, social media algorithms, prediction markets, and what effective responsible gambling policy should actually look like. Hear them discuss: 00:00 – Introductions, Isaac’s background, and navigating credibility as a young voice in gambling research 02:30 – Isaac’s path from poker and sports betting to journalism, research, and policy work 06:30 – Underage gambling exposure, loot boxes, fantasy sports, and why kids are seeing gambling content without seeking it out 10:30 – The “gamified” nature of modern life, social media algorithms, and how gambling content spreads organically 14:30 – Why social media may pose a greater risk to young people than gambling itself 18:30 – Practical regulatory ideas: opt-out limits, schedulable cool-off periods, and separating sportsbook and casino apps 22:00 – Micro-betting vs. live betting, addiction risk, and why banning micro-bets may make sense 26:00 – Same-game parlays as entertainment products vs. high-frequency betting behavior 30:00 – Prediction markets, regulatory arbitrage, and whether sportsbooks will remain the dominant betting product 34:30 – Advertising, athlete endorsements, and why gambling ads generate universal fatigue 38:30 – Gambling education, parental conversations, and what modern gambling literacy should actually teach young people     ⚡️ Follow BoB on Twitter/X ⚡️ Watch BoB on Youtube ⚡️ Apply to be a guest here

On this episode of the Business of Betting Podcast, Jeff Edelstein is joined by Seth Young, CEO of High Roller, for a wide-ranging conversation on prediction markets, public company dynamics, regulation, responsible gambling, and why the next wave of gaming may look very different from the last.   Hear them discuss: 01:00 – Seth’s background in gaming, law, and poker, and why prediction markets caught his attention at this moment 03:00 – The rapid rise of prediction markets, whether the space is getting “frothy,” and how consumer behavior is changing 04:30 – High Roller’s stock volatility following its prediction market announcement and how Seth thinks about public market pressure 08:00 – Competitive dynamics in prediction markets and what it takes to move beyond first-mover hype 11:30 – Licensing strategy, Canada expansion, and why U.S. market entry remains complex 13:00 – Prediction markets as audience-building tools and potential gateways into regulated gaming 16:30 – Supreme Court implications, states’ rights, and why government involvement is inevitable at scale 20:00 – Responsible gambling in prediction markets and why guardrails matter even outside traditional betting 24:00 – Could prediction markets extend into casino-style outcomes and other controversial frontiers? 28:00 – What’s next for High Roller, emerging trends in gaming, and Seth’s long-term outlook on the industry     ⚡️ Follow BoB on Twitter/X ⚡️ Watch BoB on Youtube ⚡️ Apply to be a guest here

On this episode of the Business of Betting Podcast, Jeff Edelstein is joined by Michael “Mando” Anderson, Co-founder of Yeet and longtime crypto entrepreneur, for a wide-ranging conversation on crypto casinos, sportsbook innovation, prediction markets, regulation, and how AI is reshaping gambling, media, and business more broadly. Hear them discuss: 01:00 – Mando’s background on Wall Street, his move into crypto, and the path that led him to gambling and media 02:30 – The founding of Yeet and why trust, transparency, and founder visibility matter in crypto gambling 05:00 – Competing in a space dominated by giants like Stake and why Yeet focuses on VIPs and community-first growth 08:00 – Launching a crypto sportsbook, regulatory realities, and why prediction markets are a different animal 11:00 – Regulation, enforcement uncertainty, and why the gambling landscape feels like a modern Wild West 14:00 – Prediction markets, insider advantage, and whether markets actually lead to “truth” 20:00 – NFTs, meme coins, and separating hype from real, lasting use cases 23:00 – Gamification, generational risk-taking, and the economic pressures driving betting behavior 26:00 – How AI is shrinking teams, replacing workflows, and changing how gambling businesses are built 29:00 – Why human connection, trust, and brand still matter in an AI-driven future 31:00 – Final thoughts on innovation, adaptability, and what’s coming next for betting and crypto   ⚡️ Follow BoB on Twitter/X ⚡️ Watch BoB on Youtube ⚡️ Apply to be a guest here  

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   ⚡️ Follow BoB on Twitter/X ⚡️ Watch BoB on Youtube ⚡️ Apply to be a guest here  

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   ⚡️ Follow BoB on Twitter/X ⚡️ Watch BoB on Youtube ⚡️ Apply to be a guest here

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     ⚡️ 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 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 guests 04:30 – Vegas history, Steve Wynn’s influence, and why the Mirage changed casino design forever 09:00 – Stadium Swim skepticism, why investors doubted it, and how it became Circa’s signature attraction 11:00 – Derek’s unlikely path from Michigan manufacturing to casino ownership and the family business roots behind it 15:00 – The Stevens brothers’ partnership, division of responsibilities, and why it’s worked for decades 17:00 – Circa Sports’ expansion into online betting, proprietary technology, and choosing where the model actually fits 20:00 – State tax revenue, problem gambling funding, and why prediction markets undermine the regulated ecosystem 22:00 – DraftKings, FanDuel, and Fanatics entering prediction markets and why Derek believes it puts future licenses at risk 23:30 – The origin story of Circa Million and Circa Survivor and how Survivor became lightning in a bottle 25:00 – Circa Survivor’s growth to a $18.7M prize pool, five perfect entries, and why the contest resonates emotionally 27:30 – Derek’s pitch for Circa: sunshine, Stadium Swim year-round, best-in-class rooms, and real value in Vegas     ⚡️ 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 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