Risk of Ruin

Half Kelly Media
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Audio documentaries about risk takers.

  1. JAN 21

    Expected Goals

    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/SportsCheetah Subscribe 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=1000743258624 Follow the show on Twitter: https://x.com/halfkelly Email the show: risk of ruin pod at gmail.

    1h 7m

  2. 12/08/2025

    Let Them Eat Cake

    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 Substack Email me: riskofruinpod at gmail Follow me on Twitter: @halfkelly

    1h 41m

  3. 10/17/2025

    Trading Games

    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 It Michael Lewis - Liar’s Poker Advantage Podcast Mixtape Vol I Advantage Podcast Mixtape Vol II Follow me on Twitter - @halfkelly.

    1h 6m

  4. 09/11/2025

    Trial and Error

    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_stephens97 Subscribe to the Premium Substack: https://riskofruinpod.substack.com/p/trial-and-error?r=ckepv&utm_campaign=post&utm_medium=web&showWelcomeOnShare=false Follow the show on Twitter: https://x.com/halfkelly

    1h 8m

  5. 08/11/2025

    Casino Schemes

    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 gmail Follow on Twitter: https://x.com/halfkelly

    1h 56m

  6. 08/11/2025

    Betting on Chaos

    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/0x9d84ce0306f8551e02efef1680475fc0f1dc1344 Domer on Twitter: https://x.com/Domahhhh Support the show by subscribing on Substack: https://riskofruinpod.substack.com Follow the show on Twitter: https://x.com/halfkelly

    1h 11m

  7. 08/10/2025

    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: @alderlaneeggs Marc's Mimedx Website: http://petiteparkerthebarker.com/ Email the show: riskofruinpod@gmail.com Twitter: @halfkelly

    54 min

  8. 08/09/2025

    Credit Card Arbitrage

    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 gmail Follow us on Twitter: https://twitter.com/halfkelly

    1h 2m
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4.9
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About

Audio documentaries about risk takers.

Information

  • Creator
    Half Kelly Media
  • Years Active
    2020 - 2026
  • Episodes
    33
  • Rating
    Explicit
  • Copyright
    © 2026 Risk of Ruin
  • Show Website
    Risk of Ruin

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