Risk of Ruin

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 Foll...

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. The Eudaemonic Pie. Bloomberg article on roulette. A Man for All Markets - which d...

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://pol...

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....

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. Find Reilly on X. https://twitter.com/ValleyBlitz_15 Support the show credit card links: https://docs.google.com/document/d/1YTMUqap_Z0D9832cOl5wYxUs16Byr6xx-iAZzrRL3VU/edit...

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: HBS Study on LTCM dividend Eric's talk at MIT in 2009 Michael Lewis article on LTCM When Genius Failed, Roger Lowenstein Follow the show on Twitter: @halfkelly Email: riskofruinpod@gmail.com Web: halfkelly.com

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. John Hempton on Twitter: https://twitter.com/John_Hempton John's Blog: http://brontecapital.blogspot.com/ Netflix documentary on Valeant: https://www.imdb.com/title/tt...

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-epi...

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. Follow Zack White on Twitter. Follow Mark DeRosa on Twitter. Follow Rufus Peabody on Twitter. Rufus's betting analytics startup: Unabated.

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. Follow Zack White on Twitter. Follow Mark DeRosa on Twitter. Follow Rufus Peabody on Twitter. Rufus's betting analytics startup: Unabated.

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: 2024 Grass Clippings Open https://www.youtube.com/watch?v=6cX0ktag2kA 2024 Good Good Desert Open https://www.youtube.com/watch?v=PE7t7K173-U Follow Grass Clippings on X (formerly Twitter): https://x.com/GrassClippingsc Follow Howard Lindzon on X (formerly Twitter)...

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 Support the show links: https://docs.google.com/document/d/1YTMUqap_Z0D9832cOl5wYxUs16Byr6xx-iAZzrRL3VU/edit Email the show: Risk of ruin pod at gmail dot com Follow us on Twitter: https://twitter.com/halfkelly

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. Darryl Purpose's music website: https://darrylpurpose.com/ Richard Munchkin / Gambing With an Edge: https://www.lasvegasadvisor.com/gambling-with-an-edge/category/podcast/ Earlier episode of Risk of Ruin featuring Richard and Darryl: https:/...

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. Marc recounts the war stories from his shorts of iomega, TCBY, Lernout & Hauspie, Novastar Financial, Jos. A Bank, Bally Manufacturing, Di...

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. Email the show: riskofruinpod@gmail.com Follow us on Twitter: @halfkelly

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. Follow David on Twitter: https://twitter.com/orrdavid Support the show links: https://docs.google.com/document/d/1YTMUqap_Z0D9832cOl5wYxUs16Byr6xx-iAZzrRL3VU/edit Follow the show on Twitter: https://twitter.com/halfkelly Email: risk of ruin pod at gmail

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. In addition to blackjack, Jeff talks about his career in tech where he has focused on using data and analytics to create value. Note: an earlier upload contained a claim that the Patriots were caught filming opponent practices. That has been corr...

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. Driveline Baseball: https://www.drivelinebaseball.com/ Follow Kyle on Twitter: https://twitter.com/drivelinekyle Blackjack Shuffle Tracker's Cookbook: https://www...

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. Bert's horse farm: https://www.chasemorefarm.co.uk/ Bert's Twitter: https://twitter.com/bertthebold Email the show: riskofruinpod@gmail.com Follow us on Twitter: @halfkelly

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. Follow Jason on Twitter: https://twitter.com/strassa2 Email the show: risk of ruin pod at gmail Follow us on Twitter: https://twitter.com/hal...