Business of Betting Podcast

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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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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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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