Risk of Ruin

A very specific housing related bet. How did we go from The Big Short... to a housing shortage in such a short time? Governments in seemingly disparate places are having to take drastic measures to enable more housing...

Kris Abdelmessih writes the Moontower newsletter which is required reading for any edge seeking generalist who wants to learn about the world of volatility. Kris got his start as a trader over 20 years ago with...

Thomas started as a losing bettor, and then learned to win. Eventually he won so much that a regulated sportsbooks stole several million dollars from him. He talks about CLV, harvesting bonuses, faking the NBA overnight...

Jamie, Steve, and Kyle are advantage players. They talk about beating casino games including carnival games, automatic roulette wheels, and sweepstakes slot machines. Support the show: References from the episode...

Domer is a prediction market trader, and is one of the biggest bettors on Polymarket. He talks about his journey from Intrade, to Predictit, to Polymarket. He also talks about the 2024 election, which was a...

Marc Cohodes made a living exposing fraudulent companies, and profiting when their stock prices collapsed. But the life of a short seller is spent on a high wire because executives willing to engage in fraud don't play...

Matt writes the blog "Miles Earn and Burn" which stands alone in the credit card space. He has no ads on the site, and he writes about advanced strategies that don't make it into the mainstream travel blog world. The...

Curtis, Phil, and Reilly are professional sports bettors that provide the valuable service of getting down for originating groups. They are logistics providers in the gambling world. They talk about starting as casino...

The story of Long Term Capital Management as told by LTCM partner Eric Rosenfeld. Eric earned a PhD from MIT, then taught at Harvard Business School, then became a trader at Salomon, then was a founding partner of LTCM...

John Hempton runs Bronte Capital, which generates its excess returns primarily through shorting fraudulent companies. John walks through a hypothetical short, explaining how they find it, how they size positions, and...

Mark DeRosa, Zack White, and Rufus Peabody. The story a group of friends from Appalachian State that went on to team up with an econ grad from Yale. They started playing casino games and eventually would go on to bet...

Mark DeRosa, Zack White, and Rufus Peabody. The story a group of friends from Appalachian State that went on to team up with an econ grad from Yale. They started playing casino games and eventually would go on to bet...

Richard Munchkin and Darryl Purpose are career advantage players. Over the past 40 years they've teamed up to win millions of dollars from casinos. In this episode they recount some of the war stories and also offer...

Citrini Research has taken Fintwit by storm with a series of prescient market calls covering themes such as AI, GLP-1, and the Trump election. In this episode Citrini discusses how he arrived at thematic investing, the...

Jake Hoselton is the CEO of Grass Clippings. Pete Wilson is the CMO of Grass Clippings. Howard Lindzon is the Managing Partner of Social Leverage. The guests talk about trying to build a new high stakes par 3 golf...

Mr. Doppy became an advantage player hustling the video poker game Ultimate X. Since then he's gone after online sports books, credit card points, and also a state lottery. Mr. Doppy's Twitter account: Support the show...

Houyi went from Yale Law School to a job in finance before he left it all behind to become a professional advantage player. He talks about counting cards, learning to play hole cards, traveling the world, and a fateful...

David Orr is a former poker player turned fund manager. He started out investing with a value bias, and then eventually did a 180 and started shorting value traps. He talks about how his strategy evolved and also his...

Jeff Ma was a member of the MIT Blackjack Team. He told his story to the writer Ben Mezrich, who wrote a book titled "Bringing Down the House." The book was later made into the movie "21" which starred Kevin Spacey...

Kyle Boddy is the founder of Driveline Baseball, which promises data driven performance training. He is best known for training pitchers in baseball. Prior to his career in sports Kyle was a professional gambler. On...

Andrew "Bert" Black is a co-founder of Betfair, which is the world's largest betting exchange. He recounts his life in gambling, coming up with the idea for Betfair, and how they managed to win the P2P betting war in...

Jason Strasser is the co-founder and Chief Investment Officer of Caption Partners. While in college Jason became a high stakes poker player and was making $100k/month before he left competitive poker for Wall Street...

Evan Tindell is a former poker player and now is the CIO of Bireme Capital. He talks about how he got into the market, and also his value investing based process for finding investments. Follow Evan on Twitter: Bireme...

In 2022 Elon Musk signed an agreement to purchase Twitter. Then all hell broke loose. This episode is about that merger, the investors that traded it, and the most valuable Twitter follow to come out of the saga...

Erik Seidel and Steve Zolotow were among the gamblers to come out of the storied Mayfair Club in New York City. The Mayfair inspired some of the locations in Rounders, and is also known for the breadth of success that...