Risk of Ruin

Odcinki

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  From Pinnacle Sports to Jane Street 07.09.2026 1godz 4min

  Support the show by subscribing to the Premium Substack. (Search "ARCHIVE" for past paywalled episodes.) Guest: Zvi Mowshowitz grew up playing Magic the Gathering. He played on the Pro Tour, and is now in the Magic Pro Tour Hall of Fame. He then moved on to sports betting, and eventually became a trader for Pinnacle Sports. Zvi has also worked for the quant trading firm Jane Street. Zvi currently writes the Don't Worry About the Vase Substack which provides daily expansive coverage of AI. You...
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  Advantage Programming - Part II 06.07.2026 40min

  Canzhi is a programmer and also part of a sports betting syndicate. He talks about his path from coding in middle school to computer science in college, to becoming a software developer. Then he left the mainstream world for professional gambling. Canzhi also talks about using OpenAI Codex to do the data science work that his betting group relies on. Follow Canzhi on Twitter: https://x.com/canzhiye Follow the show on Twitter: https://x.com/halfkelly Substack Archive: https://riskofruinpod.sub...
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  Advantage Programming - Part I 26.06.2026 1godz

  Cartwright is an advantage player and is in a unique position to comment on the intersection of programming and advantage play. He was a software engineer until he left that career for full time gambling. In the past he has used his programming skills to hit vulnerable table games. Now he is more focused on sports. He talks about AI and advantage play. Cartwright on Gambling With an Edge: https://www.youtube.com/watch?v=jJ1IXeW9y8s Subscribe to the premium Substack: https://riskofruinpo...
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  Turning Over 70,000 Rocks 14.05.2026 53min

  Andrew Martin is the CEO of Fairlight Capital. Fairlight invests in small call value stocks all over the world. In this episode Andrew talks about finding these value names, his diligence process, the firm's use of AI, and how to know whether to sell a loser. Fairlight's investor letters: https://www.fairlightcapital.com/investor-letters Follow Andrew on Twitter: https://x.com/Fairlight_Cap Follow the show on Twitter: https://x.com/halfkelly Support the show: https://riskofruinpod.substack.co...
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  Call Security 25.03.2026 1godz 13min

  Jordan and Ohio Mike are part of a group of advantage players that spread their plays across casinos (physical and online), sportsbooks (physical and online), and various manufactured spending related opportunities. Subscribe to the Substack and Support the show: https://riskofruinpod.substack.com/ Email: risk of ruin pod at gmail Follow the show on Twitter: https://x.com/halfkelly
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  Expected Goals 20.01.2026 1godz 7min

  Preston Johnson and a group called WAGMI United had a novel idea to buy an English football club and then use NFT sales to fund player spending. Their goal was to take a club from League Two and gain eventual promotion to the Premier League. Follow Preston on Twitter: https://x.com/SportsCheetah Subscribe to the Premium Substack: https://riskofruinpod.substack.com/ Preston on Bet the Process: https://podcasts.apple.com/us/podcast/end-of-year-with-sports-cheetah-preston-johnson/id1291010585?i=...
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  Let Them Eat Cake 08.12.2025 1godz 40min

  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 development. This episode is about how those conditions materialized in the United States, and also whether anything can be done to ameliorate the situation. Kevin Erdmann is a Senior Affiliated Scholar at the Mercatus Center. Kevin’s SubstackFollow Kevin on TwitterBen Bea...
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  Trading Games 17.10.2025 1godz 5min

  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 - ...
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  Trial and Error 10.09.2025 1godz 8min

  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...
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  Casino Schemes 11.08.2025 1godz 56min

  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...
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  Betting on Chaos 10.08.2025 1godz 11min

  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...
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  Life's Too Short 09.08.2025 53min

  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...
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  Credit Card Arbitrage 09.08.2025 1godz 1min

  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....
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  Movers 08.08.2025 1godz 35min

  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...
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  Inside Long Term Capital 07.08.2025 1godz 3min

  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: [email protected] Web: halfkelly.com
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  Zero, by Way of a Hundred 06.08.2025 55min

  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...
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  Greetings from Las Vegas - Part I 23.05.2025 46min

  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.
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  Greetings from Las Vegas - Part II 22.05.2025 45min

  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.
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  The Road of Trials 21.05.2025 49min

  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: [email protected] Follow us on Twitter: @halfkelly
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  The Audacity of Help 21.05.2025 1godz 13min

  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:/...