Business of Betting Podcast

E297 - Peter Hammon

On this episode of the Business of Betting Podcast, Jeff Edelstein sits down with Peter Hammon, gaming attorney and consultant at Vela Wood, to discuss prediction markets, exchange wagering, regulatory risk, and the legal battles that could shape the future of sports betting in America. 
 
Hear them discuss:
Why prediction markets have created a modern-day gold rush for operators, market makers, and investors looking to capitalize on a rapidly evolving opportunity
The growing role of market makers and liquidity providers operating across sportsbooks, prediction markets, and international trading platforms
How companies like Kalshi, Polymarket, Fanatics, Novig, and Sporttrade are positioning themselves for a future where prediction markets and sports betting increasingly overlap
The legal and regulatory risks facing businesses operating across both state-regulated sportsbooks and federally regulated prediction markets
Whether prediction markets have become too big to fail and why Peter believes the ultimate question centers on state versus federal authority over sports wagering
Why Kalshi is emphasizing non-sports markets as it prepares for future legal and regulatory challenges
The similarities between prediction markets, exchange wagering, poker, and peer-to-peer betting models, and why many of these concepts have existed for years under different names
Peter’s journey into gaming law, from launching the UCLA Gaming Law Association to joining Smarkets and helping shape the early exchange wagering movement in the United States
How Daily Fantasy Sports helped pave the way for PASPA’s repeal and fundamentally changed the trajectory of legal sports betting in America
California’s ongoing sports betting stalemate, the leverage prediction markets may be giving tribal operators, and why the state's unique geography continues to shape the debate
 
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E296 - Chris Dierkes from Novig

On this episode of the Business of Betting Podcast, Jeff Edelstein sits down with Chris Dierkes, Head of Trading at Novig, to discuss exchange-based betting, prediction markets, bankroll management, and the future of the sports betting industry. 
 
Hear them discuss:
Why Chris believes betting exchanges provide better value for consumers through tighter pricing, lower fees, and increased flexibility
The differences between traditional sportsbook cash-out features and exchange trading, and why bettors should understand the hidden costs involved
Whether exchanges are actually safer and more consumer-friendly than sportsbooks despite the learning curve for new users
Novig’s strategy for competing with prediction market leaders like Kalshi and Polymarket in an increasingly crowded marketplace
The challenge of convincing recreational bettors to prioritize price and value over promotions, bonuses, and brand familiarity
How Chris uses the Kelly Criterion to manage risk and determine position sizing when betting with significant edges
The thought process behind placing million-dollar wagers and why bankroll management matters more than headline bet sizes
Lessons learned from building a betting operation, scaling a bankroll, and overcoming the limitations imposed by traditional sportsbooks
The regulatory uncertainty surrounding prediction markets and how potential Supreme Court involvement could shape the industry's future
Why Chris chose to move from professional betting into exchange operations, and what he sees as the biggest opportunities ahead for market-based wagering
 
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E295 - David Woodley from SpeedLabs

On this episode of the Business of Betting Podcast, Jeff Edelstein sits down with David Woodley, sports betting entrepreneur, investor, and advisor to companies including Edge Markets and Speed Labs, to share his perspective on prediction markets, gambling’s place in society, and the startups building the next generation of betting products.
 
Hear them discuss:
Why gambling should be viewed more like alcohol, something most people can enjoy responsibly rather than through an all-or-nothing lens
The rise of prediction markets, the regulatory battles surrounding them, and why younger founders are reshaping the industry
David’s work with Edge Markets and how the company is reducing payment friction for bettors, sportsbooks, and prediction market traders
The evolution of Speed Labs from a survivor pool game into a real-time prediction market platform powered by proprietary micro-market technology
Why David believes betting “pick services” are often overrated, while niche businesses focused on solving one problem exceptionally well remain underrated
The parallels between gambling, entrepreneurship, collectibles, investing, and other forms of risk-taking
How gambling education could benefit from the same practical approach used for alcohol and financial literacy
The opportunities and challenges facing startups building products around prediction markets and sports gaming
Lessons learned from building, investing in, and advising companies across the betting ecosystem
A lighthearted discussion on sports fandom, heartbreak, and why Vikings and Mets fans share a special bond
 
 
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E294 - Alfonso Straffon from Matchbook Betting Exchange

On this episode of the Business of Betting Podcast, Jeff Edelstein sits down with Alfonso Straffon to discuss his journey from Costa Rica’s offshore sportsbook boom to Wall Street bond trading and back into sports betting through the rise of prediction markets.
 
Hear them discuss:
Alfonso’s unique career path through offshore sportsbooks, finance, equity research, and prediction markets
The evolution of sports betting from credit bookmakers and offshore operators to online, mobile, and in-play betting
How PASPA changed the industry and reshaped the future of offshore sportsbooks
Why Matchbook believes sports prediction markets and betting exchanges can thrive alongside traditional sportsbooks
The similarities between financial markets, bond trading, sports betting, and prediction market price discovery
The opportunities and regulatory risks facing prediction markets in the United States
How operators like DraftKings, FanDuel, Kalshi, and Matchbook may compete in the next phase of market evolution
The impact prediction markets are having on offshore sportsbooks and betting behavior in unregulated states
Why Alfonso believes exchange-style betting offers better economics and longevity for bettors
His vision for Matchbook’s U.S. launch and the future of sports-focused prediction
 
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E293 - Matt Kalish

On this episode of the Business of Betting Podcast, Jeff Edelstein sits down with Matt Kalish, co-founder of DraftKings and founder of Hardscope, to discuss his public criticism of Kalshi, the risks of exchange-style betting products, and why he believes prediction markets are being marketed incorrectly to everyday consumers.
 
Hear them discuss:
Why Matt’s first experience betting on Kalshi triggered concerns about pricing, liquidity, and customer transparency
The wager that sparked his deep dive into prediction market mechanics
How exchange-style betting differs from traditional sportsbook experiences
Why Matt believes retail users are competing against sophisticated Wall Street market makers and API traders
The ethical concerns around marketing prediction markets as “easy” or beatable for everyday users
Lessons DraftKings learned from the early daily fantasy sports boom and regulatory backlash
The similarities and differences between DFS-era marketing and today’s prediction market messaging
Why Matt believes companies should clearly position these products as financial markets—not casual sports betting apps
Concerns around transparency, enforcement, wash trading, and market surveillance
How traditional sportsbooks and state regulators may respond to prediction markets moving forward
Why operators like DraftKings and FanDuel can’t afford to ignore the prediction market space
Matt’s perspective on consumer product DNA versus Wall Street infrastructure culture
Why he believes recreational bettors prioritize entertainment and trust over pure trading mechanics
The future of creator-led marketing and why gambling companies still haven’t mastered the creator economy
Matt’s transition from DraftKings into building Hardscope and his interest in digital media and creator platforms
 
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E292 - Dan Zimmermann from Betting Intelligence

On this episode of the Business of Betting Podcast, Jeff Edelstein sits down with Dan Zimmermann, co-founder and Chief Intelligence Officer of Betting Intelligence, to discuss the explosive growth of prediction markets and the weaponization of market data.
 
Hear them discuss:
How Dan transitioned from launching a consumer-facing app to founding a private firm focused on the underlying intelligence value of prediction markets
Why he defines "BETINT" as a new discipline alongside OSINT and HUMINT dedicated to interpreting behavior on gambling and stock platforms
How prediction markets have expanded far beyond sports to price complex real-world realities like the outbreak of wars and assassinations
Why current insider trading guardrails are largely an illusion against individuals with true non-public information who know how to conceal their identity
How bad actors and state operations can manipulate public sentiment using fake AI footage and bot farms to move market lines for financial profit
The phenomenon of "signal jamming" and how million-dollar volume walls are strategically placed to absorb and mask smaller informational leaks
How Betting Intelligence utilizes deep wallet forensics and a natural language AI interface to provide an information insurance layer for newsrooms and government agencies
Why Dan’s biggest fear is that massive institutional capital will eventually enter these platforms and price out everyday retail traders
 
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Ep 291 - Megan Lanham from Rithmm

On this episode of the Business of Betting Podcast, Jeff Edelstein sits down with Megan Lanham, co-founder and CEO of Rithmm, to discuss the intersection of artificial intelligence and sports betting, the transition from elite coaching to tech entrepreneurship, and how predictive modeling is becoming accessible to the everyday bettor. 
 
  Hear them discuss:
Megan’s unconventional career path, moving from D1 basketball player and coach to running a pharmaceutical recruiting company before attending MIT and founding an AI startup.
The technical reality of Rithmm’s modeling, which utilizes machine learning to ingest billions of paid data points rather than relying on "fugazi" AI or basic scraping.
Why she left the world of Division I coaching, citing the "parochial" nature of campus life and a gut feeling that she needed to stretch herself beyond the university bubble.
The "serendipitous" origin story of Rithmm, including a chance meeting at a birthday party bar that turned a predictive modeling class project into a business.
What separates Rithmm from the competition, specifically its "intelligence layer" that allows users to build, back-test, and copy successful models via a community leaderboard.
The dynamic nature of the model, which must constantly recompute as lines move, players are announced out, and odds shift in real-time.
Navigating the ethics of collegiate sports, including why Rithmm refuses to offer player props on college athletes and Megan’s concerns regarding the risks to students.
New product innovations like "Scout," a proprietary AI layer designed to allow bettors to query complex models through voice and text to find the "why" behind a pick.
The reality of the startup grind, from sharing desks in garden-level offices to raising over $8 million in funding to scale the platform.
 
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E290 - Kevin Roth

On this episode of the Business of Betting Podcast, Jeff Edelstein sits down with Kevin Roth, meteorologist and founder of a leading weather analytics platform, to discuss the growing role of weather data in sports betting, the rise of AI-driven models, and how niche expertise can still stand out in an increasingly crowded market.
 
Hear them discuss:
How Kevin built a 13+ year career turning weather data into actionable insights for DFS players and bettors
The rise of AI-powered weather models and why access to raw data still creates a major edge
Surprising weather-driven outcomes in baseball, including how cold temperatures can outweigh strong winds
Why baseball is uniquely suited for weather modeling—and the challenges of applying similar models to football and other sports
His experience at RotoGrinders and Better Collective, and how layoffs ultimately pushed him to go independent
The balance between content, analysis, and personal life—and why he stepped away from hosting to focus on family
How understanding probability connects weather forecasting and sports betting mindsets
The realities of being a TV meteorologist, from early mornings to the unseen work behind broadcasts
New product innovations, including roof data tracking and simplified weather-based scoring systems
The shift from DFS to sports betting audiences and why betting is now the primary use case for his data
 
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E289 - Nigel Eccles from BetHog

On this episode of the Business of Betting Podcast, Jeff Edelstein sits down with Nigel Eccles, CEO and Co-founder of BetHog, to discuss AI-powered casino innovation, prediction markets, crypto payments, and the future of gambling product design.
 
Hear them discuss:
Why Nigel believes AI dealers could make up the majority of live dealer gaming within five years
How BetHog is using AI avatars and conversational interfaces to reimagine blackjack and online casino entertainment
Why product innovation—not marketing spend—is the biggest opportunity 
The case for voice interfaces, AI copilots, and rethinking sportsbook user experiences
How prediction markets compare to the early legal battles of FanDuel and DraftKings
Why Nigel sees major upside and major legal risk for sports event prediction markets
His view that crypto’s biggest gambling use case is payments, not speculation
Why the U.S. online betting market remains brutally difficult for new operators
How AI personalization intersects with responsible gambling and product ethics
 
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E288 - Scott Savin from World Jai Alai League

On this episode of the Business of Betting Podcast, Jeff Edelstein sits down with Scott Savin, COO of World Jai Alai League, to discuss the revival of one of the fastest and most dangerous sports in the world through modern betting and media.
 
Hear them discuss:
The strategy behind reviving Jai Alai as a modern betting product, shifting from pari-mutuel wagering to fixed-odds formats on platforms like DraftKings and FanDuel
Reinventing the sport for today’s audience, including format changes, faster gameplay, and structuring matches like tennis for better betting engagement
Building a league from scratch by recruiting and training athletes rather than relying solely on traditional jai alai players
The role of distribution, including streaming on ESPN+ and the importance of landing a major streaming deal to scale a niche sport
Betting performance and early traction, with growing wager volume and increasing engagement across sportsbooks
Overcoming the sport’s past challenges around integrity, scandals, and perception through strict regulation and monitoring
The vision for expansion, including team-based leagues in Miami and Las Vegas and long-term international growth
The intersection of sports, entertainment, and betting and why niche sports need gambling and media to survive and thrive
 
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