Risk of Ruin

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.

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.

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

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

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

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.

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 

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/drivelinekyleBlackjack Shuffle Tracker's Cookbook: https://www.amazon.com/Blackjack-Shuffle-Trackers-Cookbook-Arnold/dp/B001CH9S0IBeyond Coupons: https://www.lasvegasadvisor.com/gambling-with-an-edge/wp-content/uploads/2022/02/beyondcouponsbjfo.pdfThe Risk of Ruin Newsletter: https://riskofruinpod.substack.com/?utm_source=substack&utm_medium=web&utm_campaign=substack_profileEmail the show: risk of ruin pod @ gmailFollow us on Twitter: https://twitter.com/halfkelly

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/berttheboldEmail the show: riskofruinpod@gmail.comFollow 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/strassa2Email the show: risk of ruin pod at gmailFollow us on Twitter: https://twitter.com/halfkelly