Risk of Ruin

Hosted by Half Kelly Media

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Latest episode

Jul 2026

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EN-US

About the show

Audio documentaries about risk takers.

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30 recent

July 6, 202640 min

Advantage Programming - Part II

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

June 26, 20261 hr 0 min

Advantage Programming - Part I

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

May 14, 202653 min

Turning Over 70,000 Rocks

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.

March 25, 20261 hr 13 min

Call Security

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

January 21, 20261 hr 7 min

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.

December 8, 20251 hr 40 min

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 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

October 17, 20251 hr 5 min

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.

September 11, 20251 hr 8 min

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

August 11, 20251 hr 56 min

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

August 11, 20251 hr 11 min

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