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Risk of Ruin

Half Kelly Media
Risk of Ruin
Latest episode

50 episodes

  • Risk of Ruin

    Advantage Programming - Part I

    26/06/2026 | 1h
    Cartwright is an advantage player and is in a unique position to comment on the intersection of programming and advantage play. He was a software engineer until he left that career for full time gambling. In the past he has used his programming skills to hit vulnerable table games. Now he is more focused on sports. He talks about AI and advantage play. 
    Cartwright on Gambling With an Edge: https://www.youtube.com/watch?v=jJ1IXeW9y8s
    Subscribe to the premium Substack: https://riskofruinpod.substack.com/
    Twitter: https://x.com/halfkelly
    Email: risk of ruin pod at gmail
  • Risk of Ruin

    Turning Over 70,000 Rocks

    14/05/2026 | 53 mins.
    Andrew Martin is the CEO of Fairlight Capital. Fairlight invests in small call value stocks all over the world. In this episode Andrew talks about finding these value names, his diligence process, the firm's use of AI, and how to know whether to sell a loser.
    Fairlight's investor letters: https://www.fairlightcapital.com/investor-letters
    Follow Andrew on Twitter: https://x.com/Fairlight_Cap
    Follow the show on Twitter: https://x.com/halfkelly
    Support the show: https://riskofruinpod.substack.com/
    LEGAL DISCLAIMER:  This content is for informational purposes only and should not be considered financial, legal, or tax advice. Investing involves risk, including potential loss of principal. Always consult with a certified financial professional to consider your personal circumstances before making any investment decisions.
  • Risk of Ruin

    Call Security

    25/03/2026 | 1h 13 mins.
    Jordan and Ohio Mike are part of a group of advantage players that spread their plays across casinos (physical and online), sportsbooks (physical and online), and various manufactured spending related opportunities.
    Subscribe to the Substack and Support the show: https://riskofruinpod.substack.com/
    Email: risk of ruin pod at gmail
    Follow the show on Twitter: https://x.com/halfkelly
  • 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
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About Risk of Ruin
Audio documentaries about risk takers.
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