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.

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.

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.

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

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

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

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

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.