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  • From Pinnacle Sports to Jane Street
    2026/09/07

    Support the show by subscribing to the Premium Substack. (Search "ARCHIVE" for past paywalled episodes.)

    Guest:

    Zvi Mowshowitz grew up playing Magic the Gathering. He played on the Pro Tour, and is now in the Magic Pro Tour Hall of Fame. He then moved on to sports betting, and eventually became a trader for Pinnacle Sports. Zvi has also worked for the quant trading firm Jane Street.

    Zvi currently writes the Don't Worry About the Vase Substack which provides daily expansive coverage of AI. You can follow him on X.

    Email the show: risk of ruin pod at gmail

    Follow the show on X:

    Antonino DeRosa on Gambling With an Edge.

    OpenAI Executive Sounds Pretty Nervous About AI

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    1 時間 4 分
  • Advantage Programming - Part II
    2026/07/06

    Canzhi is a programmer and also part of a sports betting syndicate. He talks about his path from coding in middle school to computer science in college, to becoming a software developer. Then he left the mainstream world for professional gambling.

    Canzhi also talks about using OpenAI Codex to do the data science work that his betting group relies on.

    Follow Canzhi on Twitter: https://x.com/canzhiye

    Follow the show on Twitter: https://x.com/halfkelly

    Substack Archive: https://riskofruinpod.substack.com/

    (To find past paywalled episodes of the show search the word "ARCHIVE" in the search bar in the top right).

    Email the show: risk of ruin pod at gmail

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    41 分
  • Advantage Programming - Part I
    2026/06/26

    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

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    1 時間 1 分
  • Turning Over 70,000 Rocks
    2026/05/14

    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.

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    54 分
  • Call Security
    2026/03/25

    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

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    1 時間 13 分
  • Expected Goals
    2026/01/21

    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.

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    1 時間 7 分
  • Let Them Eat Cake
    2025/12/08

    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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    1 時間 41 分
  • Trading Games
    2025/10/17

    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.

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    1 時間 6 分