Business of Betting Podcast

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

 

 

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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

 

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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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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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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.