Explore every episode of the podcast Risk of Ruin
| Title | Pub. Date | Duration | |
|---|---|---|---|
| Startup Sports League | 26 Jul 2024 | 01:17:55 | |
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. | |||
| Value Traps | 27 May 2024 | 01:09:46 | |
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. | |||
| The Audacity of Help | 21 Jul 2024 | 01:13:15 | |
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 teamwork. | |||
| The Character Building Side Effect of Losing | 26 Dec 2023 | 00:52:21 | |
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 trading options, looking for one-off events where the volatility of the options are mispriced by algorithms. | |||
| Waiting on Value | 26 Dec 2023 | 00:49:06 | |
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. | |||
| Zero, by Way of a Hundred | 07 Aug 2025 | 00:55:27 | |
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 can be expected. He also discusses his shorts of Valeant Pharmaceutical and Wirecard. | |||
| Life's Too Short | 20 Jul 2024 | 00:53:32 | |
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 freedom is at stake. Marc tells the stories of the adversity he's faced holding public companies accountable. | |||
| Rocket Man | 20 Oct 2023 | 01:46:10 | |
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. | |||
| The Mayfair Revisited | 20 Oct 2023 | 01:24:26 | |
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 poker. The episode covers the history of the club, its bridge and backgammon roots, and the careers of Erik and Steve. | |||
| A Family Business | 18 Oct 2023 | 01:02:02 | |
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 starting as a backgammon player during the heyday of that game. Dan joined him in professional gambling when they found opportunities with the early internet sportsbooks. | |||
| The Game-like Aspect | 16 Oct 2023 | 00:47:08 | |
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 plan. | |||
| The Frontier - Part II | 19 Aug 2023 | 00:58:26 | |
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 the show on all of the platforms check out the Linktree. https://linktr.ee/johnreeder | |||
| Movers | 08 Aug 2025 | 01:35:15 | |
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 having several hundred thousand dollars taken from them by a sportsbook. | |||
| The Frontier - Part I | 17 Aug 2023 | 01:10:18 | |
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. | |||
| The Road of Trials | 19 Jul 2024 | 00:49:55 | |
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. | |||
| Bill Perkins is Not Afraid | 06 May 2023 | 00:44:45 | |
Bill Perkins is a natural gas trader, a minor celebrity in the poker world, and the author of "Die With Zero." Bill talks about his start in the markets and becoming an energy trader. He tells the story of almost blowing up during an extremely cold winter. | |||
| Inside Long Term Capital | 07 Aug 2025 | 01:03:12 | |
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. | |||
| The Disrespected | 01 May 2023 | 01:12:42 | |
Marc Cohodes was the subject of the prior episode titled "Life's Too Short." Marc returns to the podcast to talk about figuring out the FTX scheme, using that to short Silvergate, and Signature Banks, and also the banking turmoil that has followed. | |||
| Rabbit Hole | 16 Feb 2023 | 01:05:28 | |
An episode about the ever elusive idea of winning at craps using physical skill, aka dice control. | |||
| From Blackjack to Black Monday | 08 Feb 2023 | 00:34:05 | |
Blair Hull played on the original Big Player blackjack team in the 1970s. He played with Al Francesco, Ken Uston, and ran into other pioneers of the game including Keith Taft. The Francesco teams were the subject of the book "The Big Player". After blackjack Blair moved into the financial markets where he used his proprietary options strategies to turn $25,000 into millions. Blair talks about his life searching for edges, and the lessons he learned. | |||
| Greetings from Las Vegas - Part I | 23 May 2025 | 00:46:51 | |
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 over Las Vegas. | |||
| Made in America - Part I | 01 Sep 2022 | 00:44:31 | |
The lives of two sharp sports bettors, and one bookmaker. Our guests talk about getting started in gambling, going from losers to winners, and the technology they use to keep their edges. | |||
| Made in America - Part II | 01 Sep 2022 | 00:47:45 | |
The lives of two sharp sports bettors, and one bookmaker. The guests expand on the relationship between sharp bettors and bookmakers. Spanky talks about being the target of a government investigation. | |||
| Greetings from Las Vegas - Part II | 22 May 2025 | 00:45:32 | |
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 over Las Vegas. | |||
| Blackjack Legacy | 04 Mar 2024 | 00:50:06 | |
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 Sturgess. | |||
| Credit Card Arbitrage | 09 Aug 2025 | 01:01:57 | |
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 in having Matt as a guest said basically: go to your local credit union and see if there's anything that you might be able to profit from. In the advantage play world that would be called scouting. In the manufactured spend world it's known as probing. https://milesearnandburn.com/index.php/2023/09/29/taking-a-stroll-to-the-local-financial-district/ | |||
| You Can't Beat the Lottery* | 23 Jul 2024 | 00:58:29 | |
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. | |||
| A Healthy Disrespect | 02 Mar 2024 | 01:00:04 | |
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 stories about exploiting online casino bonuses, as well as shuffle tracking, and playing poker. | |||
| A Seemingly Obvious Idea | 02 Mar 2024 | 00:45:25 | |
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. | |||
| Betting on Chaos | 11 Aug 2025 | 01:11:19 | |
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 rollercoaster. It featured highs - like backing Kamala Harris before President Joe Biden had even dropped out of the race - and also lows, like being short Trump on election night. Domer also talks about unraveling the mystery of the so-called French Whale. Domer on Polymarket: https://polymarket.com/profile/0x9d84ce0306f8551e02efef1680475fc0f1dc1344 Domer on Twitter: https://x.com/Domahhhh Support the show by subscribing on Substack: https://riskofruinpod.substack.com Follow the show on Twitter: https://x.com/halfkelly | |||
| Trial and Error | 11 Sep 2025 | 01:08:17 | |
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 market, parlays, SGPs, round robins, and VIP rewards. Follow Thomas on Twitter: https://x.com/t_stephens97 Subscribe to the Premium Substack: https://riskofruinpod.substack.com/p/trial-and-error?r=ckepv&utm_campaign=post&utm_medium=web&showWelcomeOnShare=false Follow the show on Twitter: https://x.com/halfkelly | |||
| Casino Schemes | 11 Aug 2025 | 01:56:19 | |
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: https://riskofruinpod.substack.com/ References from the episode: Laurence Scott on Gambling With an Edge. Mark Billings on Gambling With an Edge (related to biased wheels), and also using computers. Mark Billings on Risk of Ruin. Bloomberg article on roulette. A Man for All Markets - which describes Ed Thorp’s effort to beat roulette. Kyle’s appearance on Gambling With an Edge. Email the show: risk of ruin pod at gmail Follow on Twitter: https://x.com/halfkelly | |||
| Big. Chunky. Changes. | 23 Jun 2025 | 01:00:53 | |
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 process he uses to find baskets of stocks, and also what it’s like to write up a thesis for tens of thousands of subscribers. Find Citrini on Substack. Find Citrini on Twitter. Support the show by subscribing to the Premium Substack: https://riskofruinpod.substack.com/p/new-episode-big-chunky-changes?r=ckepv Email the show: risk of ruin pod at gmail Follow the show on Twitter: @halfkelly | |||
| Trading Games | 17 Oct 2025 | 01:05:58 | |
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 Susquehanna. He talks about getting the job, SIG’s training program, and the “degenerate atmosphere.” Kris also talks about his career where he moved from pit to pit, and then ultimately became a portfolio manager at a vol focused hedge fund. Kris also has options analytics software - Moontower AI - and you can follow him on Twitter - @KrisAbdelmessih. References from the episode: David Sklansky - Getting the Best of It Michael Lewis - Liar’s Poker Advantage Podcast Mixtape Vol I Advantage Podcast Mixtape Vol II Follow me on Twitter - @halfkelly. | |||