Risk of Ruin

Latest Episodes:

This is My (Chess) Quant Nov 09, 2026

Show notes

Dr. Kenneth Regan is a professor of computer science at the University of Buffalo. He is perhaps best known for his work to prove and disprove allegations of cheating in chess.
In this episode Ken talks about his discovery that he had a unique background to approach this problem, his model for evaluating chess matches, and the important issues that are weighed in any suspected cheating case.
Ken's website: https://cse.buffalo.edu/~regan/

Email the show - risk of ruin pod at gmail

https://x.com/halfkelly

00:00 Before we start
00:27 A moment of scientific joy
02:54 An embarrassing admission
04:20 No basis to establish cheating
05:54 Inference from imperfect information
07:10 A form of language
08:40 From 1400 to nearly master
09:33 Dots and lines
10:54 Too often, with Fritz 9
13:13 29 of 32
14:46 Loaded for bear
17:53 Elo in two minutes
20:00 A thousand-sided die
22:08 Four motives
25:03 Over the board is hard
26:17 Cheating in small increments
27:54 Fourth and 15
29:47 A 2850 signal
31:47 Ceilings
33:47 Not a magic button
35:55 How sure is sure?
37:47 Four times the data
39:51 Fast moves, better moves
44:10 Look elsewhere
48:55 The frozen envelope
51:21 Kramnik accuses Nakamura
52:50 Frozen ratings
54:32 1845 on the wall chart
57:18 The dog that didn't bark
59:21 Doing science faithfully

From Pinnacle Sports to Jane Street Sep 07, 2026

Show notes

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

Advantage Programming - Part II Jul 06, 2026

Show notes

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

Advantage Programming - Part I Jun 26, 2026

Show notes

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

Turning Over 70,000 Rocks May 14, 2026

Show notes

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.

Call Security Mar 25, 2026

Show notes

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

Expected Goals Jan 20, 2026

Show notes

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.

Let Them Eat Cake Dec 08, 2025

Show notes

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

Trading Games Oct 17, 2025

Show notes

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.

Trial and Error Sep 10, 2025

Show notes

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

Our TOPPODCAST Picks

Follow Us

Stay Connected

Related Podcasts

Links

Stay Connected