Business of Betting Podcast

On this episode of the Business of Betting Podcast, Jeff Edelstein sits down with Peter Overzet, fantasy sports personality, content creator, and entrepreneur, for a candid conversation on creativity, monetization, best ball growth, and the realities of building a media career in betting and fantasy sports.

Hear them discuss:
00:00 – Peter’s background in fantasy, DFS, and content creation, and how he navigates a fragmented media landscape
02:30 – The rise of the “Pete Mans” persona, using humor to break into the industry, and why parody worked
05:30 – Early pivots through poker, crypto, and NFTs, and how chasing curiosity shaped his career path
08:30 – Moving away from characters and leaning into authenticity as a long-term brand strategy
14:30 – The current state of fantasy sports, industry layoffs, and concerns about innovation stagnation
17:30 – Why best ball continues to grow while traditional DFS struggles to evolve
20:30 – Monetization realities: balancing W2 work, affiliates, partnerships, and content revenue
24:00 – Long-running shows, on-air trust, and why chemistry beats rigid formats
27:30 – Outsourcing, operations, and the unsexy work behind sustainable content businesses
30:30 – Fatherhood, time management, and becoming more intentional with creative energy

 

 

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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

 

 

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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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