Business of Betting Podcast

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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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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