Risk of Ruin

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/SportsCheetahSubscribe to the Premium Substack: https://riskofruinpod.substack.com/Preston on Bet the Process: https://podcasts.apple.com/us/podcast/end-of-year-with-sports-cheetah-preston-johnson/id1291010585?i=1000743258624Follow the show on Twitter: https://x.com/halfkellyEmail the show: risk of ruin pod at gmail.

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 Senior Affiliated Scholar at the Mercatus Center.Kevin’s SubstackFollow Kevin on TwitterBen Bear is the CEO of BuildCasa.BuildCasa websiteFollow Ben on TwitterCody is a homebuilder in Oregon.Show resources:It’s Time to Build - Marc AndreessenBut not in Atherton - Marc AndreessenInstitutional SFR landlord on ResiClub podcastSupport the show: Subscribe to the Premium SubstackEmail me: riskofruinpod at gmailFollow me on Twitter: @halfkelly

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 became a portfolio manager at a vol focused hedge fund.Kris also has options analytics software - Moontower AI - and you can follow him on Twitter - @KrisAbdelmessih.References from the episode:David Sklansky - Getting the Best of ItMichael Lewis - Liar’s PokerAdvantage Podcast Mixtape Vol IAdvantage Podcast Mixtape Vol IIFollow me on Twitter - @halfkelly.

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_stephens97Subscribe to the Premium Substack: https://riskofruinpod.substack.com/p/trial-and-error?r=ckepv&utm_campaign=post&utm_medium=web&showWelcomeOnShare=falseFollow the show on Twitter: https://x.com/halfkelly

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 on Risk of Ruin.The Eudaemonic Pie.Bloomberg article on roulette.A Man for All Markets - which describes Ed Thorp’s effort to beat roulette.Kyle’s appearance on Gambling With an Edge.Email the show: risk of ruin pod at gmailFollow on Twitter: https://x.com/halfkelly

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 talks about unraveling the mystery of the so-called French Whale.Domer on Polymarket: https://polymarket.com/profile/0x9d84ce0306f8551e02efef1680475fc0f1dc1344Domer on Twitter: https://x.com/DomahhhhSupport the show by subscribing on Substack: https://riskofruinpod.substack.comFollow the show on Twitter: https://x.com/halfkelly

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 from. In the advantage play world that would be called scouting. In the manufactured spend world it's known as probing. https://milesearnandburn.com/index.php/2023/09/29/taking-a-stroll-to-the-local-financial-district/Email the show: risk of ruin pod at gmailFollow us on Twitter: https://twitter.com/halfkelly

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_15Support the show credit card links: https://docs.google.com/document/d/1YTMUqap_Z0D9832cOl5wYxUs16Byr6xx-iAZzrRL3VU/edit?usp=sharingEmail us: risk of ruin pod at gmailFollow on X: https://twitter.com/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: [email protected]: halfkelly.com

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: [email protected] the show on Twitter: https://twitter.com/halfkelly