

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

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

May 23, 2025 • 47min
Greetings from Las Vegas - Part I
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.

5 snips
May 22, 2025 • 46min
Greetings from Las Vegas - Part II
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.

10 snips
May 22, 2025 • 50min
The Road of Trials
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.comFollow us on Twitter: @halfkelly

9 snips
May 21, 2025 • 1h 13min
The Audacity of Help
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://podcasts.apple.com/us/podcast/david-goliath-part-i/id1527018692?i=1000493338179James Grosjean's "Beyond Coupons": https://www.lasvegasadvisor.com/gambling-with-an-edge/wp-content/uploads/2022/02/beyondcouponsbjfo.pdfEmail the show: risk of ruin pod at gmailFollow us on Twitter: https://twitter.com/halfkelly

50 snips
May 20, 2025 • 1h 1min
Big. Chunky. Changes.
Citrini, the brains behind Citrini Research, is revolutionizing thematic investment with his sharp market insights. He dives into the art of crafting investment theses and how understanding human behavior can lead to better predictions. He shares his emotional rollercoaster with Super Micro Computer and emphasizes the significance of long-term perspectives. Discussions also cover the impact of GLP-1 drugs on markets and the dynamic nature of creating effective stock baskets, all while advocating for transparency through the Citrindex.

Jul 26, 2024 • 1h 18min
Startup Sports League
Jake Hoselton and Pete Wilson, key players behind Grass Clippings, join Howard Lindzon, Managing Partner at Social Leverage. They dive into their ambitious venture of creating a high-stakes par-three golf league and discuss the emotional ties fans have with sports. The trio shares amusing tales from golf tournaments, focusing on the innovative transformation of courses for night play and community involvement. They also explore the rise of 'alt-golf' and its appeal to new audiences, reflecting on the intersection of sports, entertainment, and investment opportunities.

Jul 23, 2024 • 58min
You Can't Beat the Lottery*
Mr. Doppy, an advantage player and expert in video poker hustles, shares his journey through the thrilling world of gambling. He dives into calculated strategies for playing Ultimate X and overcoming the skepticism associated with lotteries. With tales of points hacking and navigating the complexities of credit card rewards, he highlights the emotional toll of chasing expected value. Doppy also reflects on the unexpected struggles that winners face, illustrating the intricate balance between luck, skill, and personal growth in gambling.

May 27, 2024 • 1h 10min
Value Traps
Former poker player turned fund manager, David Orr, discusses evolving his investment strategy from value bias to shorting value traps. Topics include transitioning from poker to stocks, meme stock phenomenon, navigating stock investing complexity, successful long bets, adaptive investment approaches, using Twitter for market insights, and the path to success in investing.

31 snips
Mar 4, 2024 • 50min
Blackjack Legacy
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 corrected in the episode. They were accused of that, but they dispute it, and there was no evidence found.Links: The Bet the Process Podcasthttps://podcasts.apple.com/us/podcast/bet-the-process/id1291010585Follow Jeff on Twitter:https://twitter.com/jeffmaRisk of Ruin Substack:https://riskofruinpod.substack.com/Email the show: risk of ruin pod at gmailFollow us on Twitter: https://twitter.com/halfkelly


