
Risk of Ruin
Audio documentaries about risk takers.
Episodes
40 episodes
Startup Sports League
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 league.Links:
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1:17:55

Movers
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 APs, finding sports, and h...
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1:35:15

Credit Card Arbitrage
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 post that got me interested...
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1:01:57

You Can't Beat the Lottery*
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: https://twitter.com/MrDoppy...
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58:29

The Audacity of Help
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 reflections on the nature of...
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1:13:15

Zero, by Way of a Hundred
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 the kinds of returns that c...
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55:27

Life's Too Short
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 by the rules when their f...
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53:32

The Road of Trials
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 poker game in Cambodia.
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49:55

Inside Long Term Capital
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.Resources:
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1:03:12

Value Traps
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 plan to grow his fund.<...
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1:09:46

Greetings from Las Vegas - Part I
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 the max at sports books all...
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46:51

Greetings from Las Vegas - Part II
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 the max at sports books all...
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45:32

Blackjack Legacy
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, Kate Bosworth, and Jim Sturg...
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50:06

A Healthy Disrespect
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 this episode he tells storie...
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1:00:04

A Seemingly Obvious Idea
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 the early 2000s. <...
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45:25

The Character Building Side Effect of Losing
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. Today he generates his edge...
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52:21

Waiting on Value
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:https://twitter.com/eva...
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49:06

Rocket Man
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.Guests:Chris DeMuth ...
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1:46:10

The Mayfair Revisited
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 its players have had in po...
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1:24:26

A Family Business
Jim and Dan Pasko talk about their father and son sportsbetting operation. The Paskos use math to find positive EV bets like correlated parlays and player props. Jim Pasko has been a professional gambler for almost his entire adult life, first ...
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1:02:02

The Game-like Aspect
Kai talks about leaving the work world behind in favor of early retirement, and the part time pursuit of bank and credit card bonuses. He also discusses Lean FIRE (Financial Independence Retire Early) and how churning bonuses fits into his FIRE...
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47:08

The Frontier - Part II
To this point we've published 33 podcast episodes covering everything from slot machines to hedge funds. This episode is Part II of an attempt to make sense of the guests, and make sense of the domain they operate in.To find t...
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58:26

The Frontier - Part I
To this point we've published 33 podcast episodes covering everything from slot machines to hedge funds. This episode is Part I of an attempt to make sense of the guests, and make sense of the domain they operate in.To find the show on ...
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1:10:18
