Top 5 Invest Like the Best Podcast Episodes


Let’s just calm the bleep down for a minute. NFTs, Dogecoins, and Mars hotels can wait; we need to get back to some fundamentals. It’s time to relax with some timeless advice, level-headed insight, and soothing conversation. Patrick O’Shaughnessy creates “Invest Like The Best,” one of the most succinct and informative podcasts out there covering all things investing. So clear your palette, grab a cup of decaf, and enjoy one of the most sensible, thoughtful, and enlightening podcasts in the financial world.

If you’re not familiar, Patrick is CEO of O’Shaughnessy Asset Management and runs over $5 billion under management. When he’s not busy as Chief Executive overseeing OSAM’s business, he produces one of the top business and investing podcasts out there.

Invest Like The Best

It’s almost impossible to do a “Top 5” Invest Like the Best list. I could probably make a “Top 50 episodes” list and still have a tough time narrowing it down. I was a subscriber to Patrick’s book-club recommendations email list when, in late 2016, he announced he was delving into the podcast world and starting “Invest Like the Best.” I clearly remember looking forward to his first episode, and obviously, it delivered right out of the gate with an epic interview by legend Jeff Gramm. A few minutes into the very first episode, I knew it would be one of my go-to podcasts from then on. And the show has only improved over the last 5 years.

So here’s my attempt at the preposterous goal of ranking my Top 5 favorite Invest Like the Best episodes. Every week there’s a new amazing guest with completely fresh perspectives. Odds are that you’ve already been listening, but if you haven’t yet, I highly recommend you check it out.

Brent Beshore, November 2016

The first time I heard the ‘Invest Like the Best’ episode with Brent Beshore, I stopped what I was doing and instantly Googled this guy. And there wasn’t much to be found at the time. Apparently, this was Brent’s first podcast interview ever, but his rap was so smooth and compelling I was confused by what I was actually hearing. Were they playing some sort of trick? How could someone give an interview like that on his first attempt? It sounded like Brent had done nothing but podcast interviews since he was a toddler. That’s how smart this guy is.

Brent Beshore buys companies and operates them. It seems pretty simple – It’s not. If you have any experience running a small or mid-sized business, you are well aware of the knife-fight you wake up to every morning. Brent is an expert in this struggle. During the episode, Brent explains how his team attempts to find excellent companies to buy, and it’s not for the faint of heart. Out of 2,000 companies with 1 to 10 million dollars in owner earnings he and his team analyzed over the course of a year, they completed three deals. That’s a whole lot of due diligence for just 3 deals. But the painstaking investigation is exactly what it takes in this treacherous arena, or you will be eaten alive.

The goal is to “buy boring businesses and make them less boring,” as Brent describes. This was an amazing interview because of the rare combination of Brent’s extreme intelligence for business along with his unique and humble persona. The title of the podcast is “cultivating a disaster resistant, compound interest machine.” To compound over the long-term, you must first and foremost remain operational and stay in business. Brent does an excellent job explaining how complicated it is to run a company and how he attempts to add value. Brent has done multiple interviews with Patrick since his first appearance, and they’re all captivating.


Josh Wolfe, February 2018

As Co-founder and managing partner of Lux Capital, Josh Wolfe has a front-row seat to the world of investing. The title of this episode is actually called “This Is Who You Are Up Against.” And this phrase runs through my mind quite often since I listened to this interview. There are people out there operating on a whole different level than the rest of us, and you know who they are when you hear them. The Josh Wolfe episode is a great example of this thought.

Josh Wolfe is a machine. When you listen to him give interviews, he is absolutely relentless. Idea after idea, the guy does not quit; Josh is shockingly brilliant. His humble beginnings and background are super interesting. He’s completely shot out of a cannon, delivering the goods on investing, the technology world, and where we may be headed in the future. When Patrick says, “this is who you are up against,” he is basically saying, good luck competing with people like Josh Wolfe.

Listening to Josh Wolfe gives me a slight headache – but in a good way. Maybe it’s from the panic and realization that I’m struggling to keep up with the guy, and he could lose me altogether at any second. Like running in the lane next to Usain Bolt, I am outmatched in every sense. Much respect Mr. Wolfe. And to everyone else, this is who you are up against, don’t forget it.


Brian Koppelman, January 2017

Brian Koppelman is a really intriguing figure. Someone who I’ve come to be familiar with through listening to his own podcast called, The Moment. Koppelman is a writer, director, and filmmaker, who’s shared much of his amazing journey through his podcast. He’s super compelling because of his genuine authenticity and desire to generously share so much of what he’s learned. Koppelman doesn’t shy away from questions about his deeply personal struggles and challenges and how he has risen to the very top of his field.

One of Brian Koppelman’s favorite topics is how some people face a moment when they decide to become what they know they should be. He describes his “Moment,” where he decided to become a writer, and after working with Julia Cameron’s “The Artist’s Way,” he was able to “un-block” his writing ability. A year later, he had three different screenplays in some phase of production.

With his hit Showtime series “Billions,” Koppelman has immersed himself in the world of hedge fund titans and billionaire Wall Street tycoons. The conversation includes a debate over society’s infatuation with billionaires and the aura that surrounds them.


Shane Parrish, December 2016

If you enjoy finance and investing, you will want to explore this Invest Like the Best episode with Shane Parrish. This is not an interview on the nuts and bolts of running companies or analyzing P-E ratios but a wide-ranging conversation on discovery.

Shane Parrish runs Farnam Street with the goal of “helping you master the best of what other people have already figured out.” In addition to Farnam Street, Parrish also hosts his own podcast titled “The Knowledge Project,” where he explores problem-solving and decision making.

Some of the most memorable podcast episodes are where I’m introduced to other great podcasts. After listening to the Shane Parrish episode on Invest Like the Best, I dove head-first into “The Knowledge Project” and discovered hundreds more gold nuggets of wisdom. This is a great example of the incredible value one can gain from such a solid podcast such as Patrick’s show.


Jim O’Shaughnessy, March 2017

Patrick’s father, Jim O’Shaughnessy, founded O’Shaughnessy Asset Management in 2007 after a long career on Wall Street, working for various asset managers. Jim shares many old stories of his struggle, determination, and some luck to rise through Wall Street’s ranks and eventually make the move to forming his own firm.

The discussion starts at the very beginning of Jim’s investing career, which happens to be when he was just a teenager. Jim had the opportunity to participate in his family’s business discussions. But, come to find out, this was not your typical family. Jim had unique insight from a prominent, influential, and well-known family with deep roots in the community.

The interview was personally fascinating for me from the very start because I was able to connect a few dots that hadn’t registered until this discussion. It turns out, Jim’s family is from the same area I’m from, and I quickly realized that a University I’m very familiar with is directly related to Jim and Patrick. Nearly half the buildings at this certain University have the “O’Shaughnessy” name on them, and I found out some fascinating history directly from the source on how this occurred.

Jim’s grandfather, Ignatius, made a fortune in the oil industry during the 1920s and 30s. But much of his legacy is found in his generosity and support of the area he grew up in. Jim discusses stories from his ancestors, helping me piece together some fascinating history of a place very recognizable to me. Already a fan of the podcast and Patrick’s book recommendation list for years prior, this conversation was a pleasant surprise that hit close to home and provided just one more reason to admire and respect Patrick’s podcast and the O’Shaughnessy family.


Invest Like The Best and Colossus

Recently, Patrick announced the formation of Colossus, with the mission “to become the leading destination to learn about business building and investing.” With Colossus, Patrick and his crew want to create a resource for investment professionals and entrepreneurs to find answers to tough questions through an easy to consume and enjoyable format.

It’s a monumental task, but if Patrick’s display of mastery in the Podcast world over the last five or six years is any indication, there’s no doubt Colossus will be a gigantic success as well. I would highly recommend you visit the Colossus website. I could already spend a few weeks consuming the content found there, and they are just getting started.