Business of Betting Podcast

Latest Episodes:

E301 - Adam Small from Third Planet Media Jul 23, 2026

Show notes

On Episode 301 of the Business of Betting podcast, the tables are turned as Third Planet CEO Adam Small takes over hosting duties to interview Jeff Edelstein. Together, they reflect on the evolution of the U.S. sports betting industry since PASPA, debate prediction markets, discuss the future of gambling regulation, and explore why the industry's biggest challenges may still lie ahead.
Hear them discuss:

The rise and growing pains of the regulated U.S. sports betting market since PASPA was repealed
Why higher tax rates, betting limits, and shifting regulation have changed the industry's outlook
Looking back at the "gold rush" era of sports betting and whether those opportunities still exist
Why community remains one of sports betting's biggest untapped opportunities, from live events to social experiences
How DFS paved the way for products like PrizePicks, Kalshi, and prediction markets
The ongoing debate over what qualifies as gambling versus financial trading
Whether prediction markets can justify their soaring valuations and challenge established sportsbooks
Why DraftKings, FanDuel, and other incumbents may still be best positioned to dominate if prediction markets expand
The growing concern around gambling's influence on younger audiences and the need for gambling education in schools
Jeff's predictions for where sports betting, prediction markets, and the broader gambling industry are headed over the next decade

⚡️ Follow BoB on Twitter/X

⚡️ Watch BoB on Youtube

⚡️ Apply to be a guest here

E300 - Dave Portnoy from Barstool Sports Jul 16, 2026

Show notes

On Episode 300 of the Business of Betting podcast, Jeff Edelstein is joined by Barstool Sports founder Dave Portnoy for a candid conversation covering the rise of Barstool, the ESPN Bet partnership, gambling regulation, cancel culture, media, politics, philanthropy, and what the future might hold, including a possible run for public office.
Hear them discuss:

Why the Barstool Sportsbook partnership ultimately failed, what went wrong with ESPN Bet, and how strict regulatory oversight limited Barstool's ability to market authentically.
Dave's approach to building Barstool's culture, creating viral content, and empowering talent behind brands like Pardon My Take, Call Her Daddy, and The Pat McAfee Show.
The origin of the iconic One Bite Pizza Reviews and how a simple office debate turned into one of Barstool's biggest brands.
The story behind The Barstool Fund, raising over $50 million to help hundreds of small businesses survive the COVID-19 shutdowns.
How Dave navigates controversy, media criticism, cancel culture, and where he draws the line between accountability and online outrage.
Dave's views on politics, why he believes more outsiders should enter public service, and whether a future political campaign is truly on the table.
His perspective on antisemitism, social media polarization, and why he has become more outspoken in recent years.
The business lessons behind Barstool's growth, why authenticity beats traditional media, and how Dave evaluates creative talent.
Dave's passion for sports betting, horse racing, investing, and why he still loves wagering despite decades in the industry.
What's next for Dave Portnoy—from Barstool's future to horse racing ambitions, and why he believes his biggest challenge may still be ahead.

⚡️ Follow BoB on Twitter/X

⚡️ Watch BoB on Youtube

⚡️ Apply to be a guest here

E299 - John Phillips from PredictIt Jul 09, 2026

Show notes

On this episode of the Business of Betting podcast, Jeff Edelstein is joined by John Aristotle Phillips, founder of PredictIt and CEO of Aristotle.
Hear them discuss:

How PredictIt was founded and why prediction markets emerged as an alternative to traditional polling
Why prediction markets could fundamentally change the way people think about risk, probability, and decision-making
The future of sports prediction markets and why forecasting extends far beyond politics and sports
How media companies, businesses, and consumers may use prediction markets as everyday forecasting tools
The regulatory challenges facing prediction markets and why balanced oversight is essential for long-term growth
Whether political prediction markets should be viewed as protected political speech rather than gambling
The extraordinary story behind John's Princeton thesis demonstrating how an atomic bomb could be designed using publicly available information
How John's passion for nuclear nonproliferation led him into politics and the creation of Aristotle, a leading political technology company
The role AI could play in prediction markets and why human judgment will continue to matter
John's vision for a future where prediction markets help guide everything from financial decisions and healthcare to everyday life

⚡️ Follow BoB on Twitter/X

⚡️ Watch BoB on Youtube

⚡️ Apply to be a guest here

E298 - David Purdum from ESPN Jul 02, 2026

Show notes

On this episode of the Business of Betting podcast, Jeff Edelstein sits down with ESPN sports betting reporter David Purdum to discuss the evolution of the betting industry, the rise of prediction markets, AI's impact on journalism, responsible gambling, and the integrity challenges shaping the future of sports wagering.
Hear them discuss:

David Purdum's journey from newspaper journalism to becoming ESPN's leading sports betting reporter
How the sports betting industry has evolved from offshore books to legalization and today's prediction market era
Why AI is becoming an essential tool for journalists and how it improves reporting and research
The future of prediction markets and whether they can coexist with traditional sportsbooks
The rise in betting integrity scandals and why player prop markets deserve closer scrutiny
Responsible gambling, operator accountability, and the challenges of protecting vulnerable bettors
Why gambling addiction is often called the "hidden addiction" and the unique risks it presents
The need for gambling education in schools and whether the legal betting age should be increased
How gambling mechanics are expanding beyond sportsbooks into prediction markets, collectibles, and gamified products
David's approach to balancing a fast-paced reporting career with coaching youth soccer and maintaining perspective

⚡️ Follow BoB on Twitter/X

⚡️ Watch BoB on Youtube

⚡️ Apply to be a guest here

E297 - Peter Hammon Jun 25, 2026

Show notes

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

⚡️ Follow BoB on Twitter/X

⚡️ Watch BoB on Youtube

⚡️ Apply to be a guest here

E296 - Chris Dierkes from Novig Jun 18, 2026

Show notes

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

⚡️ Follow BoB on Twitter/X

⚡️ Watch BoB on Youtube

⚡️ Apply to be a guest here

E295 - David Woodley from SpeedLabs Jun 11, 2026

Show notes

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

E294 - Alfonso Straffon from Matchbook Betting Exchange Jun 04, 2026

Show notes

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

E293 - Matt Kalish May 29, 2026

Show notes

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

E292 - Dan Zimmermann from Betting Intelligence May 21, 2026

Show notes

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

Our TOPPODCAST Picks

Follow Us

Stay Connected

Business of Betting Podcast

Related Podcasts

Links

Stay Connected