Business of Betting Podcast

E287 - Jonathan Gruber from Loserball

On this episode of the Business of Betting Podcast, Jeff Edelstein sits down with Jonathan Gruber, Founder of Loserball, to discuss a unique twist on fantasy sports where success comes from predicting failure. 
 
Hear them discuss:
00:00 – Introduction to Jonathan's background and the concept behind Loserball
01:00 – The “contrarian” fantasy sports model: rooting for everything to go wrong
02:00 – How the game works: categories of futility, weighted questions, and strategy
04:00 – Early product experimentation and why pure chaos didn’t work for most players
06:00 – Finding the right balance between humor, unpredictability, and skill-based play
08:00 – The origins of the idea and how traditional fantasy sports became too complex
11:00 – Why community banter and shared misery can be just as entertaining as winning
14:00 – Lessons learned from building and iterating on a niche sports gaming product
18:00 – Who the ideal Loserball player is and why fantasy players enjoy the twist
23:00 – The future of alternative fantasy formats and opportunities for experimentation in sports gaming
 
Want to play for yourself? Head to Loserball.com to learn more and subscribe so you can play next football season. 
 
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E286 - Adam Rosenberg & CJ Buskey from Handigraphs

On this episode of the Business of Betting Podcast, Jeff Edelstein is joined by Adam Rosenberg and CJ Buskey of Handigraphs for a deep dive into building a smarter, AI-driven sports betting analytics platform.
 
Hear them discuss:
How Handigraphs was born from the need to replace juggling multiple tools like FanGraphs and Baseball Savant
Turning complex stats into simple, actionable insights for everyday bettors
The power of matchup-based data and why “recent form” beats traditional averages
How their platform uncovers betting edges especially in props and DFS
Building a product that works for both sharp bettors and beginners
The rise of personalization in betting tools, from custom filters to tailored dashboards
Integrating AI to speed up research and deliver smarter betting insights
Why the future of betting is having your own AI-powered assistant
Standing out in a crowded analytics space by complementing—not competing with—other tools
The long-term vision: evolving from a data platform into a fully AI-driven betting experience
 
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E285 - Jordan Bender from Citizens

On this episode of the Business of Betting Podcast, Jeff Edelstein is joined by Jordan Bender, Senior Equity Research Analyst at Citizens, for a deep dive into the rapidly evolving sports betting and prediction markets landscape.Hear them discuss:
How the repeal of PASPA created a fast-moving, unpredictable market where long-term forecasting has become increasingly difficult
Why prediction market users may lose more on average and how sharper bettors are shifting into these platforms
Why analysts and investors are now focused on quarterly performance instead of long-term fundamentals.
How prediction markets are attracting a younger audience compared to traditional sportsbook users
Why legalization has been slower than expected and what needs to happen for major states like New York to move forward
Why companies like DraftKings and Flutter may be undervalued despite current headwinds
How emerging betting formats could face increased scrutiny from regulators
Whether prediction markets will ultimately be treated as gambling or as a legitimate financial asset class
 
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E284 - Patrick Mostboeck from Sportradar

On this episode of the Business of Betting Podcast, Jeff Edelstein is joined by Patrick Mostboeck, SVP of Fan Engagement at Sportradar, for a conversation on how sports data powers the global betting ecosystem, the evolution of fan engagement tools, and how technology is shaping the future of the sports experience.
 
Hear them discuss:
Introduction to Patrick Mostboeck and an overview of Sportradar’s role at the intersection of sports data, media, and betting
How Sportradar built its foundation as a global sports data company covering nearly a million sporting events annually
The evolution from pure data collection to a broader ecosystem including video streaming, integrity services, and fan engagement tools
Patrick’s role leading Fan Engagement and how Sportradar helps operators create deeper interactions with sports fans
Why data visualization, real-time stats, and interactive experiences are becoming essential for sportsbooks and media platforms
The importance of micro-moments in sports consumption and how bettors increasingly engage during live games
How sportsbooks, media companies, and leagues are converging around shared data and technology infrastructure
Integrity monitoring in global sports betting and how Sportradar works to protect competitions and markets
The impact of AI and automation on sports data collection, analytics, and fan-facing products
Differences between U.S. and international betting markets and how operators approach fan engagement in each
Patrick’s outlook on the future of sports data, fan engagement, and where innovation in the betting ecosystem is headed next.
 
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E283 - Chris Christie

On this episode of the Business of Betting Podcast, Jeff Edelstein is joined by Chris Christie, former Governor of New Jersey, for a wide-ranging conversation on the legalization of sports betting in the United States, the landmark Supreme Court decision that changed the industry, and the ongoing evolution of regulation, competition, and responsible gambling.
 
Hear them discuss:
00:00 – Governor Chris Christie joins the podcast and explains how he got pulled back into the sports betting conversation, now working with the AGA on prediction markets.
02:30 – Christie’s core issue with prediction markets: why he believes they are violating state laws and undermining established regulatory frameworks.
04:00 – The importance of state-by-state regulation post-PASPA repeal and how the current system has worked effectively.
06:00 – Why legal battles between states and prediction market operators are likely headed back to the Supreme Court.
07:00 – Concerns around consumer protection, tax revenue loss, and lack of regulatory oversight in prediction markets.
08:00 – The debate: are prediction markets actually beneficial for bettors, or do they create more risk than value?
09:30 – The rise of microbetting and live betting, and why some markets may need to be scaled back based on integrity concerns.
10:30 – His stance on banning prop bets in college sports and the pressure they place on student-athletes.
11:30 – The role of regulation, enforcement, and accountability in protecting athletes and consumers.
12:00 – Comparing today’s betting landscape to the early days of DFS and why the stakes are much higher now.
13:00 – Christie on re-entering the public conversation, media appearances, and staying engaged in the industry.
18:00 – A lighter moment: Christie compares Donald Trump to a “live bettor” and discusses impulsiveness in decision-making.
21:00 – Closing thoughts on the Mets, sports fandom, and how betting has changed fan engagement across generations.
 
 
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E282 - Joe Maloney from Sports Betting Alliance

On this episode of the Business of Betting Podcast, Jeff Edelstein is joined by Joe Maloney, President of the Sports Betting Alliance to discuss the policy battles shaping the future of regulated sports betting in the United States.Hear them discuss:
00:00 – Joe discuss the role of the Sports Betting Alliance and the current state of U.S. sports betting policy.
02:00 – An overview of the organization’s mission and how it represents major sportsbook operators in legislative and regulatory conversations.
06:30 – Why prediction markets have become a hot topic and why the SBA has not taken a unified position.
12:00 – Joe explains why online casino expansion remains a major priority for operators and industry advocates.
18:30 – A look at which states could be next to legalize and what hurdles remain in key markets.
24:00 – How policymakers weigh tax revenue, consumer protection, and pressure from competing stakeholders.
30:00 – Joe shares his outlook on upcoming legislative fights and where the industry may be headed next.
35:00 – Final reflections on the evolving landscape and the role of advocacy groups in shaping the future of betting.
 
 
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E281 - Peter Overzet from Fantasy Life

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 landscape02:30 – The rise of the “Pete Mans” persona, using humor to break into the industry, and why parody worked05:30 – Early pivots through poker, crypto, and NFTs, and how chasing curiosity shaped his career path08:30 – Moving away from characters and leaning into authenticity as a long-term brand strategy14:30 – The current state of fantasy sports, industry layoffs, and concerns about innovation stagnation17:30 – Why best ball continues to grow while traditional DFS struggles to evolve20:30 – Monetization realities: balancing W2 work, affiliates, partnerships, and content revenue24:00 – Long-running shows, on-air trust, and why chemistry beats rigid formats27:30 – Outsourcing, operations, and the unsexy work behind sustainable content businesses30:30 – Fatherhood, time management, and becoming more intentional with creative energy
 
 
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E280 - Isaac Rose Berman

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 research02:30 – Isaac’s path from poker and sports betting to journalism, research, and policy work06:30 – Underage gambling exposure, loot boxes, fantasy sports, and why kids are seeing gambling content without seeking it out10:30 – The “gamified” nature of modern life, social media algorithms, and how gambling content spreads organically14:30 – Why social media may pose a greater risk to young people than gambling itself18:30 – Practical regulatory ideas: opt-out limits, schedulable cool-off periods, and separating sportsbook and casino apps22:00 – Micro-betting vs. live betting, addiction risk, and why banning micro-bets may make sense26:00 – Same-game parlays as entertainment products vs. high-frequency betting behavior30:00 – Prediction markets, regulatory arbitrage, and whether sportsbooks will remain the dominant betting product34:30 – Advertising, athlete endorsements, and why gambling ads generate universal fatigue38:30 – Gambling education, parental conversations, and what modern gambling literacy should actually teach young people
 
 
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E279 - Seth Young from High Roller

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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E278 - Mando from Yeet

On this episode of the Business of Betting Podcast, Jeff Edelstein is joined by Mando, 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 media02:30 – The founding of Yeet and why trust, transparency, and founder visibility matter in crypto gambling05:00 – Competing in a space dominated by giants like Stake and why Yeet focuses on VIPs and community-first growth08:00 – Launching a crypto sportsbook, regulatory realities, and why prediction markets are a different animal11:00 – Regulation, enforcement uncertainty, and why the gambling landscape feels like a modern Wild West14:00 – Prediction markets, insider advantage, and whether markets actually lead to “truth”20:00 – NFTs, meme coins, and separating hype from real, lasting use cases23:00 – Gamification, generational risk-taking, and the economic pressures driving betting behavior26:00 – How AI is shrinking teams, replacing workflows, and changing how gambling businesses are built29:00 – Why human connection, trust, and brand still matter in an AI-driven future31:00 – Final thoughts on innovation, adaptability, and what’s coming next for betting and crypto
 
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