

Risk of Ruin
Half Kelly Media
Audio documentaries about risk takers.
Episodes
Mentioned books

18 snips
Dec 8, 2025 • 1h 41min
Let Them Eat Cake
Kevin Erdmann, a housing economist at the Mercatus Center, and Ben Baer, CEO of BuildCasa, delve into the surprising shift from the 2008 financial crash to today's housing shortages. They discuss how post-crash regulations transformed the lending landscape, leading to a rental market boom. Erdmann shares insights on migration-induced demand bubbles and the intricacies of zoning laws as barriers to housing development. Baer reveals innovative strategies for leveraging small-lot developments in California and the challenges posed by recent legislation.

85 snips
Oct 17, 2025 • 1h 6min
Trading Games
Kris Abdelmessih is an experienced options trader, former portfolio manager, and author of the Moontower newsletter, known for his insights into volatility trading. He shares his journey from Susquehanna, discussing the unique training environment and how game-playing skills translate to trading success. Kris explains the intricacies of options trading, the importance of volatility over direction, and the challenges retail traders face. He also emphasizes the benefits of teaching kids trading as a way to develop critical life skills through decision-making games.

53 snips
Sep 11, 2025 • 1h 8min
Trial and Error
Explore the thrilling ups and downs of a gambler’s journey, from losing bets to mastering strategies like Closing Line Value and exploiting VIP promotions. Delve into the ethical dilemmas of sports betting and the psychological tactics gamblers use to cope with financial losses. Hear candid stories of navigating a complex landscape filled with market manipulation, emotional struggles, and the pursuit of strategic advantage. This is a raw look at the fine line between calculated risk and the challenges of responsible gambling.

Aug 11, 2025 • 1h 56min
Casino Schemes
Dive into the wild world of advantage players as they unravel secrets of beating casino games, from automatic roulette wheels to innovative slot strategies. Hear personal stories shaped by the Black Friday poker shutdown and the chaotic dynamics of teamwork in gambling. Discover how unconventional thinking guides problem-solving and how new sweepstakes casinos thrived during the pandemic. With anecdotes about mastering roulette and navigating the psychology of gambling, this episode balances risk with the thrilling game of chance.

15 snips
Aug 11, 2025 • 1h 11min
Betting on Chaos
Dive into the chaotic world of political betting with a seasoned trader who shares his intriguing journey from poker to prediction markets. Hear about high-stakes bets, including the thrill of backing Kamala Harris and the tumultuous experience of betting against Trump. Discover the mysterious 'French Whale' and the impact of biases on betting decisions, revealing how political loyalties influence market behaviors. The emotional rollercoaster of navigating this unpredictable landscape offers insightful lessons on risk-taking and strategic thinking.

24 snips
Aug 10, 2025 • 54min
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 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, Direct Focus, and more.Follow Marc on Twitter: @alderlaneeggsMarc's Mimedx Website: http://petiteparkerthebarker.com/Email the show: riskofruinpod@gmail.comTwitter: @halfkelly

31 snips
Aug 9, 2025 • 1h 2min
Credit Card Arbitrage
Matt, a blogger in the credit card space, discusses advanced strategies in credit card arbitrage. Topics covered include the value of American Express cards, exploiting discrepancies for profit, credit card hacking risks, automating tasks for earnings, exploring manufactured spend, and the importance of collaboration and being an empiricist.

12 snips
Aug 8, 2025 • 1h 35min
Movers
Professional sports bettors share their journey from casino advantage players to logistics providers in gambling, facing huge losses, exploring sports betting, and navigating the complexities of the industry. They discuss transitioning from card counting to advantage play, high-stakes bets, financial challenges, legal sports betting, and balancing dual careers.

28 snips
Aug 7, 2025 • 1h 3min
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:HBS Study on LTCM dividendEric's talk at MIT in 2009Michael Lewis article on LTCMWhen Genius Failed, Roger LowensteinFollow the show on Twitter: @halfkellyEmail: riskofruinpod@gmail.comWeb: halfkelly.com

11 snips
Aug 7, 2025 • 55min
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 can be expected. He also discusses his shorts of Valeant Pharmaceutical and Wirecard.John Hempton on Twitter: https://twitter.com/John_HemptonJohn's Blog: http://brontecapital.blogspot.com/Netflix documentary on Valeant: https://www.imdb.com/title/tt7909184/Email the show: riskofruinpod@gmail.comFollow the show on Twitter: https://twitter.com/halfkelly


