From Pinnacle Sports to Jane Street

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 gmailFollow the show on X: Antonino DeRosa on Gambling With an Edge.OpenAI Executive Sounds Pretty Nervous About AI

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/canzhiyeFollow the show on Twitter: https://x.com/halfkellySubstack 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

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=jJ1IXeW9y8sSubscribe to the premium Substack: https://riskofruinpod.substack.com/Twitter: https://x.com/halfkellyEmail: risk of ruin pod at gmail

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-lettersFollow Andrew on Twitter: https://x.com/Fairlight_CapFollow the show on Twitter: https://x.com/halfkellySupport 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.

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

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/SportsCheetahSubscribe 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=1000743258624Follow the show on Twitter: https://x.com/halfkellyEmail the show: risk of ruin pod at gmail.

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 SubstackEmail me: riskofruinpod at gmailFollow me on Twitter: @halfkelly

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 ItMichael Lewis - Liar’s PokerAdvantage Podcast Mixtape Vol IAdvantage Podcast Mixtape Vol IIFollow me on Twitter - @halfkelly.

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_stephens97Subscribe to the Premium Substack: https://riskofruinpod.substack.com/p/trial-and-error?r=ckepv&utm_campaign=post&utm_medium=web&showWelcomeOnShare=falseFollow the show on Twitter: https://x.com/halfkelly

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 gmailFollow on Twitter: https://x.com/halfkelly