E287 - Jonathan Gruber from Loserball

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

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

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

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

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

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

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

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

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

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