10 Podcasts I Liked, and You Might Too

Gambling, investing, credit card points... i.e. standard fare.

The general goal for each episode of the Risk of Ruin podcast is that we’ll get a guest who will take us into an esoteric topic, and then the keep our brains engaged by giving us a front row seat to their world - but also won’t give away everything.

This is just my two cents, but I think it’s that balance between getting information which is novel, but also not getting everything, that really keeps the brain in an engaged state.

When I’m not making the podcast I also listen to lots of other podcasts and I tend toward seeking out episodes that fit the pattern I’ve just described above.

Here are some episodes I like:

Cliff Asness - Masters in Business

Cliff is one of the giants of quant investing. One thing I particularly like about his value/momentum strategy is that it makes sense from a behavioral standpoint. If you spend any time watching human behavior, then you know how difficult it is for people to buy into ideas which are off trend. So just pairing momentum with value gets to that basic human impulse of wanting to own things which have done better recently.

Sampa the Great, Let Me Be Great - Song Exploder

I am a sucker for any kind of music explainer podcast (or Netflix show). This episode talks about the making of “Let Me Be Great” which is pure ear candy whether the genre is your thing or not.

Will Ferrell - Fly on the Wall

I am a middle aged man, which means that all of the Fly on the Wall guests were on Saturday Night Live when I was a young man. Which means that at a minimum I am going to love Fly on the Wall out of nostalgia. But I also love the episodes because they give you something novel. They talk about the stories behind famous sketches (like Cowbell), and they also have pointers to great small moments in sketches that could easily go unnoticed.

Mickey Crimm - Gambling With an Edge

Probably in some ways my podcast is like an unaffiliated spinoff of Gambling With an Edge. I’ve had Richard Munchkin on the show a number of times, and GWAE has done a ton of work on a lot of the well known gambling stories over the past decade. Their episodes often provide the basis of the story, which I can then build on because they’ve pointed out that the thing exists in the first place.

This episode with Mickey Crimm is great for a few reasons. First, Mickey is one of the great characters in the online gambling world. Second, he talks about actual slot machines which are the subject of advantage plays. And he mentions them, but doesn’t tell you everything you need to know. Which is my favorite kind of thing because I like to try to think about what information is still missing. Also, as Mickey says in the episode, he was a day laborer before he found advantage slots. And yet he uses what I think you could call a Bayesian approach to beating machines.

Parrell / Missy Elliott / Timbaland - Hit Parade

I am also a sucker for the “Holy shit, can you believe all of this came out of such a small area?” genre of story. This podcast talks about all of the hits that came from the artists that grew up around Virginia Beach, whose songs topped the charts in the mid 00’s.

Ken Pomeroy - Bet the Process

This episode has a great discussion of modeling college basketball from the OG of modeling college basketball. They talk about model building in general, hint at some areas that could still be ripe for study, and also talk about specifics - like how much is an individual star player worth to the point spread?

David Einhorn - Invest Like the Best

David Einhorn has been running Greenlight Capital for almost 30 years, which means that he’s had periods where their strategies really worked, and also periods where their strategies really didn’t work. If you’re talking about edges, the looming question of “what do you do when your edge has disappeared?” is probably the thing that isn’t talked about enough. In this episode David talks about what they did to address the fact that their original view of finding winners seems to have stopped working.

Hawaii on Points - Frequent Miler

I liked this episode because I have a fairly simple strategy for traveling to Hawaii on points. It is roughly:

• Southwest Companion pass for cheap flights

• Grand Hyatt Kauai / Maui Hyatt Regency / Hyatt Regency Waikiki Beach (using Chase points transferred to Hyatt)

It’s a very simple strategy but also very effective. In this episode they actually talk about a completely different path involving Citi points and Wyndham points. But that’s basically what I am looking for in a credit card points podcast. I want something that I haven’t been thinking about already.

Leigh Drogen - The Meb Faber Show

I would like to find more crypto related podcasts to listen to, but the ones I’ve found are often so full of logical errors that I have to eventually stop listening. Example: an episode focused on where are we on the S-curve for crypto, without ever establishing that an S-curve can be applied to crypto. It’s classic question begging.

This episode of the Meb Faber show was good because they simply talk about a trend following strategy for crypto. I will say that I found one of the statements in the podcast to be relatively shocking. They said roughly: the next bull market won’t involve many of the same coins from the last bull market.

Chris Bruno - Be Better Bettors

This is an older episode of BBB, but it’s one of the great gambling stories that I’ve heard. Chris Bruno was a bookmaker in the days before it was legal to be one. Eventually he ended up in prison as a result.

Henry Reardon - The Business Brew

I have been short Carvana off and on over the past 14 months or so. Before that I would see their car vending machines, which seemed preposterous, but I didn’t take much more notice than that. Then I saw a guy on Twitter who seemed to have a pretty logical case for why the entire thing was probably just a stock promotion scheme. That Twitter account was Henry Reardon. In this episode he talks about Carvana.

Hope you find in these suggestions an episode or two that is new to you.

John Reeder

Risk of Ruin Podcast