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Risk of Ruin

Half Kelly Media
Risk of Ruin
Latest episode

47 episodes

  • Risk of Ruin

    Expected Goals

    21/01/2026 | 1h 7 mins.
    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.
  • Risk of Ruin

    Let Them Eat Cake

    08/12/2025 | 1h 40 mins.
    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 Substack
    Follow Kevin on Twitter
    Ben Bear is the CEO of BuildCasa.
    BuildCasa website
    Follow Ben on Twitter
    Cody is a homebuilder in Oregon.
    Show resources:
    It’s Time to Build - Marc Andreessen
    But not in Atherton - Marc Andreessen
    Institutional SFR landlord on ResiClub podcast
    Support the show: Subscribe to the Premium Substack
    Email me: riskofruinpod at gmail
    Follow me on Twitter: @halfkelly
  • Risk of Ruin

    Trading Games

    17/10/2025 | 1h 5 mins.
    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.
  • Risk of Ruin

    Trial and Error

    11/09/2025 | 1h 8 mins.
    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
  • Risk of Ruin

    Casino Schemes

    11/08/2025 | 1h 56 mins.
    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

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About Risk of Ruin

Audio documentaries about risk takers.
Podcast website

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