Risk of Ruin

34 Episodes
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By: Half Kelly Media

Audio documentaries about risk takers.

Big. Chunky. Changes.
06/23/2025

Citrini Research has taken Fintwit by storm with a series of prescient market calls covering themes such as AI, GLP-1, and the Trump election.

In this episode Citrini discusses how he arrived at thematic investing, the process he uses to find baskets of stocks, and also what it’s like to write up a thesis for tens of thousands of subscribers.

Find Citrini on Substack.

Find Citrini on Twitter.

Support the show by subscribing to the Premium Substack: https://riskofruinpod.substack.com/p/new-episode-big-chunky-changes?r=ckepv

Email the show: ri...


Betting on Chaos
05/27/2025

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

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Startup Sports League
07/26/2024

Jake Hoselton is the CEO of Grass Clippings. Pete Wilson is the CMO of Grass Clippings. Howard Lindzon is the Managing Partner of Social Leverage.

The guests talk about trying to build a new high stakes par 3 golf league.

Links:

2024 Grass Clippings Open
https://www.youtube.com/watch?v=6cX0ktag2kA
2024 Good Good Desert Open
https://www.youtube.com/watch?v=PE7t7K173-U

Follow Grass Clippings on X (formerly Twitter):
https://x.com/GrassClippingsc
Follow Howard Lindzon on X (formerly Twitter):
https...


Movers
07/24/2024

Curtis, Phil, and Reilly are professional sports bettors that provide the valuable service of getting down for originating groups. They are logistics providers in the gambling world. They talk about starting as casino APs, finding sports, and having several hundred thousand dollars taken from them by a  sportsbook.

Find Reilly on X. https://twitter.com/ValleyBlitz_15

Support the show credit card links: https://docs.google.com/document/d/1YTMUqap_Z0D9832cOl5wYxUs16Byr6xx-iAZzrRL3VU/edit?usp=sharing

Email us: risk of ruin pod at gmail
Follow on X: https://twitter.c...


Credit Card Arbitrage
07/23/2024

Matt writes the blog "Miles Earn and Burn" which stands alone in the credit card space. He has no ads on the site, and he writes about advanced strategies that don't make it into the mainstream travel blog world. The post that got me interested in having Matt as a guest said basically: go to your local credit union and see if there's anything that you might be able to profit from. In the advantage play world that would be called scouting. In the manufactured spend world it's known as probing. https://milesearnandburn.com/index.php/2023/09/29/taking-a-stroll-to-the-local-financial-district/

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You Can't Beat the Lottery*
07/23/2024

Mr. Doppy became an advantage player hustling the video poker game Ultimate X. Since then he's gone after online sports books, credit card points, and also a state lottery.

Mr. Doppy's Twitter account: https://twitter.com/MrDoppy

Support the show links: https://docs.google.com/document/d/1YTMUqap_Z0D9832cOl5wYxUs16Byr6xx-iAZzrRL3VU/edit

Email the show: Risk of ruin pod at gmail dot com
Follow us on Twitter: https://twitter.com/halfkelly


The Audacity of Help
07/21/2024

Richard Munchkin and Darryl Purpose are career advantage players. Over the past 40 years they've teamed up to win millions of dollars from casinos. In this episode they recount some of the war stories and also offer reflections on the nature of teamwork.

Darryl Purpose's music website: https://darrylpurpose.com/
Richard Munchkin / Gambing With an Edge: https://www.lasvegasadvisor.com/gambling-with-an-edge/category/podcast/
Earlier episode of Risk of Ruin featuring Richard and Darryl: https://podcasts.apple.com/us/podcast/david-goliath-part-i/id1527018692?i=1000493338179
James Grosjean's "Beyond Coupons": https://www.lasvegasadvisor.com/gambling-with-an-edge/wp-content/uploads/2022/02/beyondcouponsbjfo.pdf<...


Zero, by Way of a Hundred
07/21/2024

John Hempton runs Bronte Capital, which generates its excess returns primarily through shorting fraudulent companies. John walks through a hypothetical short, explaining how they find it, how they size positions, and the kinds of returns that can be expected. He also discusses his shorts of Valeant Pharmaceutical and Wirecard.

John Hempton on Twitter: https://twitter.com/John_Hempton
John's Blog: http://brontecapital.blogspot.com/
Netflix documentary on Valeant: https://www.imdb.com/title/tt7909184/

Email the show: riskofruinpod@gmail.com
Follow the show on Twitter: https://twitter.com/halfkelly


Life's Too Short
07/20/2024

Marc Cohodes made a living exposing fraudulent companies, and profiting when their stock prices collapsed. But the life of a short seller is spent on a high wire because executives willing to engage in fraud don't play by the rules when their freedom is at stake. Marc tells the stories of the adversity he's faced holding public companies accountable.

Marc recounts the war stories from his shorts of iomega, TCBY, Lernout & Hauspie, Novastar Financial, Jos. A Bank, Bally Manufacturing, Direct Focus, and more.

Follow Marc on Twitter: @alderlaneeggs
Marc's Mimedx Website: http://petiteparkerthebarker.com/<...


The Road of Trials
07/19/2024

Houyi went from Yale Law School to a job in finance before he left it all behind to become a professional advantage player. He talks about counting cards, learning to play hole cards, traveling the world, and a fateful poker game in Cambodia.

Email the show: riskofruinpod@gmail.com
Follow us on Twitter: @halfkelly


Inside Long Term Capital
07/17/2024

The story of Long Term Capital Management as told by LTCM partner Eric Rosenfeld. Eric earned a PhD from MIT, then taught at Harvard Business School, then became a trader at Salomon, then was a founding partner of LTCM.

Resources:

HBS Study on LTCM dividend

Eric's talk at MIT in 2009

Michael Lewis article on LTCM

When Genius Failed, Roger Lowenstein

Follow the show on Twitter: @halfkelly
Email: riskofruinpod@gmail.com
Web: halfkelly.com


Value Traps
05/27/2024

David Orr is a former poker player turned fund manager. He started out investing with a value bias, and then eventually did a 180 and started shorting value traps. He talks about how his strategy evolved and also his plan to grow his fund.

Follow David on Twitter: https://twitter.com/orrdavid

Support the show links: https://docs.google.com/document/d/1YTMUqap_Z0D9832cOl5wYxUs16Byr6xx-iAZzrRL3VU/edit

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

Email: risk of ruin pod at gmail


Greetings from Las Vegas - Part I
03/04/2024

Mark DeRosa, Zack White, and Rufus Peabody. The story a group of friends from Appalachian State that went on to team up with an econ grad from Yale. They started playing casino games and eventually would go on to bet the max at sports books all over Las Vegas.

Follow Zack White on Twitter.

Follow Mark DeRosa on Twitter.

Follow Rufus Peabody on Twitter.

Rufus's betting analytics startup: Unabated. 


Greetings from Las Vegas - Part II
03/04/2024

Mark DeRosa, Zack White, and Rufus Peabody. The story a group of friends from Appalachian State that went on to team up with an econ grad from Yale. They started playing casino games and eventually would go on to bet the max at sports books all over Las Vegas.

Follow Zack White on Twitter.

Follow Mark DeRosa on Twitter.

Follow Rufus Peabody on Twitter.

Rufus's betting analytics startup: Unabated. 


Blackjack Legacy
03/04/2024

Jeff Ma was a member of the MIT Blackjack Team. He told his story to the writer Ben Mezrich, who wrote a book titled "Bringing Down the House." The book was later made into the movie "21" which starred Kevin Spacey, Kate Bosworth, and Jim Sturgess.

In addition to blackjack, Jeff talks about his career in tech where he has focused on using data and analytics to create value.

Note: an earlier upload contained a claim that the Patriots were caught filming opponent practices. That has been corrected in the episode. They were accused of that...


A Healthy Disrespect
03/02/2024

Kyle Boddy is the founder of Driveline Baseball, which promises data driven performance training. He is best known for training pitchers in baseball. Prior to his career in sports Kyle was a professional gambler. On this episode he tells stories about exploiting online casino bonuses, as well as shuffle tracking, and playing poker.

Driveline Baseball: https://www.drivelinebaseball.com/
Follow Kyle on Twitter: https://twitter.com/drivelinekyle
Blackjack Shuffle Tracker's Cookbook: https://www.amazon.com/Blackjack-Shuffle-Trackers-Cookbook-Arnold/dp/B001CH9S0I
Beyond Coupons: https://www.lasvegasadvisor.com/gambling-with-an-edge/wp-content/uploads/2022/02/beyondcouponsbjfo.pdf

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A Seemingly Obvious Idea
03/02/2024

Andrew "Bert" Black is a co-founder of Betfair, which is the world's largest betting exchange. He recounts his life in gambling, coming up with the idea for Betfair, and how they managed to win the P2P betting war in the early 2000s. 

Bert's horse farm: https://www.chasemorefarm.co.uk/
Bert's Twitter:  https://twitter.com/bertthebold

Email the show: riskofruinpod@gmail.com
Follow us on Twitter: @halfkelly


The Character Building Side Effect of Losing
12/26/2023

Jason Strasser is the co-founder and Chief Investment Officer of Caption Partners. While in college Jason became a high stakes poker player and was making $100k/month before he left competitive poker for Wall Street. Today he generates his edge trading options, looking for one-off events where the volatility of the options are mispriced by algorithms.

Follow Jason on Twitter: https://twitter.com/strassa2

Email the show: risk of ruin pod at gmail
Follow us on Twitter: https://twitter.com/halfkelly


Waiting on Value
12/26/2023

Evan Tindell is a former poker player and now is the CIO of Bireme Capital. He talks about how he got into the market, and also his value investing based process for finding investments.

Follow Evan on Twitter:
https://twitter.com/evantindell

Bireme Capital Blog Post on Meta:
https://www.biremecapital.com/blog/pounding-the-table-on-meta

Risk of Ruin Podcast Newsletter:
https://riskofruinpod.substack.com/

Email the show risk of ruin pod at gmail.

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


Rocket Man
10/20/2023

In 2022 Elon Musk signed an agreement to purchase Twitter. Then all hell broke loose. This episode is about that merger, the investors that traded it, and the most valuable Twitter follow to come out of the saga.

Guests:
Chris DeMuth - Rangeley Capital
https://twitter.com/ChrisDeMuthJr
Evan Tindell - Bireme Capital
https://twitter.com/evantindell
Chance, Editor in Chief of The Chancery Daily
https://twitter.com/chancery_daily

Media Clips Used:
Tesla 3rd Quarter Earnings Call
https://www.youtube.com/watch?v=c_SOWBDCQnM
David...


The Mayfair Revisited
10/20/2023

Erik Seidel and Steve Zolotow were among the gamblers to come out of the storied Mayfair Club in New York City. The Mayfair inspired some of the locations in Rounders, and is also known for the breadth of success that its players have had in poker. The episode covers the history of the club, its bridge and backgammon roots, and the careers of Erik and Steve.

Special thanks to Larry Bernstein.

Email the show: Risk of ruin pod at gmail
Twitter: @halfkelly

Follow Erik on Twitter: @Erik_Seidel


A Family Business
10/18/2023

Jim and Dan Pasko talk about their father and son sportsbetting operation. The Paskos use math to find positive EV bets like correlated parlays and player props. Jim Pasko has been a professional gambler for almost his entire adult life, first starting as a backgammon player during the heyday of that game. Dan joined him in professional gambling when they found opportunities with the early internet sportsbooks.

Follow Dan on Twitter: @dan_pasko
Follow the show on Twitter: @halfkelly
Email the show: risk of ruin pod at gmail.


The Game-like Aspect
10/16/2023

Kai talks about leaving the work world behind in favor of early retirement, and the part time pursuit of bank and credit card bonuses. He also discusses Lean FIRE (Financial Independence Retire Early) and how churning bonuses fits into his FIRE plan.

Kai's podcast: The Daily Churn
https://podcasts.apple.com/us/podcast/the-daily-churn/id1577648675

Email the show: riskofruinpod@gmail.com
Twitter: @halfkelly


The Frontier - Part II
08/19/2023

To this point we've published 33 podcast episodes covering everything from slot machines to hedge funds. This episode is Part II of an attempt to make sense of the guests, and make sense of the domain they operate in.


To find the show on all of the platforms check out the Linktree.


https://linktr.ee/johnreeder


The Frontier - Part I
08/17/2023

To this point we've published 33 podcast episodes covering everything from slot machines to hedge funds. This episode is Part I of an attempt to make sense of the guests, and make sense of the domain they operate in.

To find the show on all of the platforms check out the Linktree.

https://linktr.ee/johnreeder


Bill Perkins is Not Afraid
05/06/2023

Bill Perkins is a natural gas trader, a minor celebrity in the poker world, and the author of "Die With Zero." Bill talks about his start in the markets and becoming an energy trader. He tells the story of almost blowing up during an extremely cold winter.

Links:

Die With Zero
https://www.diewithzerobook.com/

Bill's Twitter
https://twitter.com/bp22

Bill's Instagram
https://www.instagram.com/billperkins/?hl=en

WSJ Article titled "The Last Cowboy"
https://www.wsj.com/articles/bill-perkins-is-the-last-cowboy-betting-on-volatile-gas-markets-1501844400

Email...


David & Goliath, Part I
05/05/2023

They went to Las Vegas as card counters and over years they discovered other ways to win in the casino. Eventually they became advantage players. This episode is about the Las Vegas that existed before mega resorts. Our heroes played hole cards, used computers in the casino, used video cameras in the casino - to name a few of the crazy stunts they pulled off.

Guests: Richard Munchkin, Mark Billings, Tommy Hyland, Darryl Purpose.

Contact the show: riskofruinpod@gmail.com
Twitter: @halfkelly

Links:
Gambling Wizards, Richard Munchkin
The Ultimate Edge...


David & Goliath, Part II
05/05/2023

They went to Las Vegas as card counters and over years they discovered other ways to win in the casino. Eventually they became advantage players. This episode is about the Las Vegas that existed before mega resorts. Our heroes played hole cards, used computers in the casino, used video cameras in the casino - to name a few of the crazy stunts they pulled off.

Guests: Richard Munchkin, Mark Billings, Tommy Hyland, Darryl Purpose.

Contact the show: riskofruinpod@gmail.com
Twitter: @halfkelly


The Disrespected
05/01/2023

Marc Cohodes was the subject of the prior episode titled "Life's Too Short." Marc returns to the podcast to talk about figuring out the FTX scheme, using that to short Silvergate, and Signature Banks, and also the banking turmoil that has followed.

Follow Marc on Twitter:
https://twitter.com/AlderLaneEggs

Life's Too Short
https://podcasts.apple.com/us/podcast/lifes-too-short/id1527018692?i=1000498472731

Odd Lots episode with Sam Bankman-Fried
https://podcasts.apple.com/us/podcast/sam-bankman-fried-and-matt-levine-on-how-the/id1056200096?i=1000531062191

Alan Lane on the Pomp Podcast
https://podcasts.apple.com...


Rabbit Hole
02/16/2023

An episode about the ever elusive idea of winning at craps using physical skill, aka dice control. 

Guests: Advantage player Frank B., PhD economist Robert Scott, and special guest Richard Munchkin.

Risk of Ruin Newsletter: https://riskofruinpod.substack.com/

Links: Robert Scott's papers on dice control
https://digitalscholarship.unlv.edu/cgi/viewcontent.cgi?article=1375&context=grrj
https://digitalscholarship.unlv.edu/cgi/viewcontent.cgi?article=1415&context=grrj

Gambling With an Edge episodes on dice control:
https://www.youtube.com/watch?v=8iWapKXDCH0
https://podcasts.apple.com/us/podcast/g...


From Blackjack to Black Monday
02/08/2023

Blair Hull played on the original Big Player blackjack team in the 1970s. He played with Al Francesco, Ken Uston, and ran into other pioneers of the game including Keith Taft. The Francesco teams were the subject of the book "The Big Player".  After blackjack Blair moved into the financial markets where he used his proprietary options strategies to turn $25,000 into millions. Blair talks about his life searching for edges, and the lessons he learned.

Links: Hull Tactical ETF
Email the show: riskofruinpod@gmail.com
Follow on Twitter: @halfkelly
The Big Player on Amazon


Two Hustlers
09/14/2022

Mickey Crimm hitchhiked to Laughlin with little more than a sleeping bag and a backpack. In the casinos there he learned to hustle slot machines and play video poker with an advantage. He made a career out of these advantages and built up a bankroll over the years.

Bob Dancer arrived in Vegas with a bankroll of $6,0000. He eventually became a video poker pro and then later a millionaire.

This episode is about playing casino machines with an advantage.

Resources:

Follow Risk of Ruin on Twitter: @HalfKelly

Email the...


Made in America - Part I
09/01/2022

The lives of two sharp sports bettors, and one bookmaker. Our guests talk about getting started in gambling, going from losers to winners, and the technology they use to keep their edges.

Guests: Spanky, Captain Jack Andrews, and Ray Marino

Spanky's Be Better Bettors: https://podcasts.apple.com/us/podcast/be-better-bettors/id1493902736

Captain Jack's Youtube Channel: https://www.youtube.com/watch?v=bH3gZ9jpBZY

Captain Jack's new venture: https://unabated.com

Ray Marino: https://www.bookmaker.eu/

Frank B. talks about dice control on GWAE: https...


Made in America - Part II
09/01/2022

The lives of two sharp sports bettors, and one bookmaker. The guests expand on the relationship between sharp bettors and bookmakers. Spanky talks about being the target of a government investigation.

Guests: Spanky, Captain Jack Andrews, and Ray Marino

Spanky's podcast on closing line value: https://podcasts.apple.com/us/podcast/closing-line-breakdown/id1493902736?i=1000505042641

Spanky's interview with Chris Bruno: https://podcasts.apple.com/us/podcast/christopher-bruno-interview/id1493902736?i=1000500772401

Captain Jack's Youtube Channel: https://www.youtube.com/watch?v=bH3gZ9jpBZY

Captain Jack's new venture: https://unabated.com
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