Business of Betting Podcast

Hosted by Business of Betting Podcast

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Episodes

297

Latest episode

Jun 2026

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About the show

A podcast covering the sports betting industry from the perspective of bettors, operators, and industry insiders. Hosted by Jeff Edelstein, Senior Analyst at InGame.com.

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60 recent

June 11, 2026Episode 29538 min

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

June 4, 2026Episode 29451 min

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

May 29, 2026Episode 29341 min

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

May 21, 2026Episode 29233 min

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

May 14, 2026Episode 29134 min

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

May 7, 2026Episode 29033 min

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

April 30, 2026Episode 28941 min

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

April 23, 2026Episode 28832 min

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

April 16, 2026Episode 28530 min

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

April 9, 2026Episode 28736 min

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

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