When Patrick O’Shaughnessy launched his podcast Invest Like the Best in 2016, he had no intention of building it into a media company. He just wanted to use it to interview the world’s best investing minds so that he could deepen his own understanding of the industry. But the show proved to be a huge hit, attracting some of the biggest names in finance. By 2020, he and a few co-founders launched Colossus, an investing-focused podcast network that now produces more than a half dozen shows across various finance niches.

In an interview, Colossus CEO Matt Reustle walked me through the vision behind the network, how it develops and promotes new shows, and why the company hasn’t yet launched video versions of its podcasts.

Watch our interview in the video embedded below:

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Transcript

Hey, Matt. Thanks for joining us. 

Thank you for having me, Simon. It's a pleasure to be here. 

So we're going to talk about a media company that you currently run. But first, I just want to talk about your background leading up to it. So prior to joining the company you're in now, you didn't actually have a background in media at all, right? What were you doing?

That's correct. I came from a very traditional finance background, did not even realize once I came to Colossus that I was truly in media, probably for a year or two. Much to my appreciation, you were writing about a lot of the things that I was caring about and started to realize, you know what, I think I am in the media business. But prior to that, I worked at a large investment bank for almost 10 years, worked in private equity, private credit for a few years, and was not planning to leave that world, but had an interesting opportunity that sprouted out and ultimately jumped at joining the Colossus media business.

Yeah. So you worked in finance, obviously pays well, but very grueling hours. Some people find it not very rewarding. Other people do. Where did you fall on that spectrum?

I think everything that you mentioned there is accurate. I think that I did enjoy what I was doing towards the back half of my finance career; it was very research oriented, learning about different businesses, different business models. So I probably view it in a more favorable light than many people who are put through the investment banking, grueling, painful seven days a week, you know, 20 hours a day. I had some pretty brutal hours, but at least I was enjoying a lot of the work that I was doing.

And what was your relationship to media? Had you ever wanted to be in media or was that just like completely out of left field?

So there's two things. I would say I was always a consumer of media, enjoyed books, movies, podcasts in particular quite a bit. So I was always a big user, media lover across a wide genre. I think that where my actual finance career overlapped a bit with some of the things that I've started to do in media is I was writing a lot of research reports and doing basically behind the scenes work, then compiling that into consolidated summaries. Some of those were 120 page reports. But that gave me a sense of what the institutional investing audience actually cared about. And it gave me some media sense because it is a form of content in some way. So I think that is where I was able to take some of what I was doing in the past and then actually apply it to what I'm doing now.

So from what I understand, Colossus started out as a single podcast. What podcast was that?

That was Invest Like the Best, which launched in 2016. And Patrick O'Shaughnessy was the voice and host behind that podcast. And it was something that I was listening to when I was still in the finance world. Anybody that I talked to that was a listener was also very interesting. So there was this bat signal in some ways for very interesting people to be listening to that podcast. It was very fresh. It was very different, particularly from what I was doing in the finance world. It all felt like the answers were more natural, more authentic. They were better.

It could be a lot of the same guests that you might hear in a banking interview, but completely different style, completely different output. And it wasn't until 2020 that Patrick, the summer of COVID, decided, I'm going to take this successful single property and build something bigger around it, build a media business around it. And that was the catalyst that ultimately created Colossus.

I know you can't speak for Patrick, but what was so great about the podcast? Did he have really good interview subjects? Was he very magnetic? What was it that drew people to it?

Well, I think in terms of interviewer, I'm biased, but I will give Patrick constructive criticism on various things. In terms of interviewing, I think he's up there. I can't think of a better interviewer. If I want to hear the definitive conversation with a person, I want Patrick to be the one interviewing them. And that was always what drew me towards his podcast was you could have the same guest on four different podcasts. If it was going to be on Invest Like the Best, it was always going to be the best conversation. And I think that continues to this day. So that was one.

I think his interviewing style was just always excellent. He's a very, very curious person. I think a lot of people now forget what he was doing 10 years ago, which was reading just loads and loads of books, summarizing them. He was in the institutional investing world, so he had an appreciation for that work.

So that was one thing. And then that was what started to draw higher and higher quality guests. And he just had people chirping in his ear, many media executives. You know, it was a former HBO executive who basically reamed him out over a phone call prior to that summer of 2020 and said, you're actually stupid for not building something around this. And it wasn't the first time he heard it, but it was the catalyst, the summer of COVID when people had some extra time on their hands, that drew him to build something on top of it.

And was he getting high caliber guests, like top hedge fund managers and stuff like that?

Yes. Yeah. You could think of hedge fund managers, investment managers, people that are founders of businesses that you weren't hearing anywhere else. And that continues to this day. Over the past year, Josh Kushner, his single podcast interview was with Patrick. Steve Mandel, famous hedge fund manager. Lee Ainslie, famous hedge fund manager. These people go back decades and decades. And a lot of what they want to do is kind of, you know, talk about their legacy, their career, and they want somebody who will treat it properly. And Patrick has kind of been a go-to resource for a lot of that...