Risk of Ruin

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/canzhiy...

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:/...

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_...

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

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: http...

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 Seni...

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 be...

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/t...

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 o...

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 t...

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 hi...

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 fr...

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 l...

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 Ema...

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 B...

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: Unaba...

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: Unaba...

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

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/gam...

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 F...

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. Not...

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...

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/s...

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/evantindell Bireme Capital Blog Post on Meta: https://www.biremecapital.com/blog/pounding-the-table-on-meta Risk of Ruin Podcast Newsletter: https://riskofruinpod.substa...

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 - Rangeley Capital https://twitter.com/ChrisDeMuthJr Evan Tindell - Bireme Capital https://twitter.com/evantindell Chance, Editor in Chief of The Chancery Daily https...