Business of Betting Podcast

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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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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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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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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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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