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Cliff Sosin

๐Ÿ‘ค Speaker
646 total appearances

Appearances Over Time

Podcast Appearances

Invest Like the Best with Patrick O'Shaughnessy
Cliff Sosin - Investing in Carvana - [Invest Like the Best, EP.421]

And so, you know, I started poking around quietly looking for another place to work. And I realized that so did all the other firms. in the industry had the same problem. In fact, it's endemic. Basically, one might naively think that the investing business is about maximizing performance, but it's not. It's about maximizing marketability.

Invest Like the Best with Patrick O'Shaughnessy
Cliff Sosin - Investing in Carvana - [Invest Like the Best, EP.421]

And so, you know, I started poking around quietly looking for another place to work. And I realized that so did all the other firms. in the industry had the same problem. In fact, it's endemic. Basically, one might naively think that the investing business is about maximizing performance, but it's not. It's about maximizing marketability.

Invest Like the Best with Patrick O'Shaughnessy
Cliff Sosin - Investing in Carvana - [Invest Like the Best, EP.421]

And performance is a component of marketability, but really what you're trying to do is signal talent. And the way you do that is by finding things with short feedback loops, with low amounts of noise, so that you can sort of show people, look, we did this and it worked, and we did this and it worked, and we did this and it didn't work, but on average, we win.

Invest Like the Best with Patrick O'Shaughnessy
Cliff Sosin - Investing in Carvana - [Invest Like the Best, EP.421]

And performance is a component of marketability, but really what you're trying to do is signal talent. And the way you do that is by finding things with short feedback loops, with low amounts of noise, so that you can sort of show people, look, we did this and it worked, and we did this and it worked, and we did this and it didn't work, but on average, we win.

Invest Like the Best with Patrick O'Shaughnessy
Cliff Sosin - Investing in Carvana - [Invest Like the Best, EP.421]

And the type of investing I was thinking about, basically buying a piece of a company through the stock market and owning it for a long time, these are multi-year, 3-, 5-, 10-year feedback loops that are incredibly noisy, and they just don't lend themselves to it. And if you think about it practically,

Invest Like the Best with Patrick O'Shaughnessy
Cliff Sosin - Investing in Carvana - [Invest Like the Best, EP.421]

And the type of investing I was thinking about, basically buying a piece of a company through the stock market and owning it for a long time, these are multi-year, 3-, 5-, 10-year feedback loops that are incredibly noisy, and they just don't lend themselves to it. And if you think about it practically,

Invest Like the Best with Patrick O'Shaughnessy
Cliff Sosin - Investing in Carvana - [Invest Like the Best, EP.421]

Let's say that I meet with someone from an institution, and first of all, and I convince them that I've got this. They're gonna say, how do you pick stocks? I'm gonna say, well, I think really hard. And they're gonna be like, okay, cool. I'm convinced Cliff thinks really hard. He's good at this. But then they have to go back to their committee.

Invest Like the Best with Patrick O'Shaughnessy
Cliff Sosin - Investing in Carvana - [Invest Like the Best, EP.421]

Let's say that I meet with someone from an institution, and first of all, and I convince them that I've got this. They're gonna say, how do you pick stocks? I'm gonna say, well, I think really hard. And they're gonna be like, okay, cool. I'm convinced Cliff thinks really hard. He's good at this. But then they have to go back to their committee.

Invest Like the Best with Patrick O'Shaughnessy
Cliff Sosin - Investing in Carvana - [Invest Like the Best, EP.421]

And the committee's going to be like, well, how does Cliff pick stocks? And he's like, well, he thinks really hard. And they're going to be like, well, you know, that's not very credible. And then even if they do make the investment, now, you know, they're going to own it. And so invariably, we're up, we're down, we're up, we're down. I look smart, I look dumb.

Invest Like the Best with Patrick O'Shaughnessy
Cliff Sosin - Investing in Carvana - [Invest Like the Best, EP.421]

And the committee's going to be like, well, how does Cliff pick stocks? And he's like, well, he thinks really hard. And they're going to be like, well, you know, that's not very credible. And then even if they do make the investment, now, you know, they're going to own it. And so invariably, we're up, we're down, we're up, we're down. I look smart, I look dumb.

Invest Like the Best with Patrick O'Shaughnessy
Cliff Sosin - Investing in Carvana - [Invest Like the Best, EP.421]

And along the way, they're going to be like, why did we do this? And by the way, we have a board that we're reporting to. And like, we're down this quarter because Cliff thinks really hard, apparently. This is just a really challenging setup. What this means is that When I started this, I wasn't fully aware of quite how challenging it would be.

Invest Like the Best with Patrick O'Shaughnessy
Cliff Sosin - Investing in Carvana - [Invest Like the Best, EP.421]

And along the way, they're going to be like, why did we do this? And by the way, we have a board that we're reporting to. And like, we're down this quarter because Cliff thinks really hard, apparently. This is just a really challenging setup. What this means is that When I started this, I wasn't fully aware of quite how challenging it would be.

Invest Like the Best with Patrick O'Shaughnessy
Cliff Sosin - Investing in Carvana - [Invest Like the Best, EP.421]

But the premise was that I would start a business based on really focusing on long-term compounding, finding a relatively small number of stocks, treating it like owning a piece of a business, dealing with the volatility that comes with it. And I figured it would be maximally optimized around returns and minimally optimized around marketability.

Invest Like the Best with Patrick O'Shaughnessy
Cliff Sosin - Investing in Carvana - [Invest Like the Best, EP.421]

But the premise was that I would start a business based on really focusing on long-term compounding, finding a relatively small number of stocks, treating it like owning a piece of a business, dealing with the volatility that comes with it. And I figured it would be maximally optimized around returns and minimally optimized around marketability.

Invest Like the Best with Patrick O'Shaughnessy
Cliff Sosin - Investing in Carvana - [Invest Like the Best, EP.421]

And I think certainly on the marketability side, we nailed it. And so that's where we are. But I wouldn't change a thing. It's how I'm built. So that's how I am.

Invest Like the Best with Patrick O'Shaughnessy
Cliff Sosin - Investing in Carvana - [Invest Like the Best, EP.421]

And I think certainly on the marketability side, we nailed it. And so that's where we are. But I wouldn't change a thing. It's how I'm built. So that's how I am.

Invest Like the Best with Patrick O'Shaughnessy
Cliff Sosin - Investing in Carvana - [Invest Like the Best, EP.421]

So I launched with $5.2 million. The old-fashioned way. It was $2 million from me because I'd been successful at UBS and they'd paid me. I like to joke it was a lot for post-crisis, not a lot pre-crisis. And I also got $2 million from my mom. She was a sympathetic audience. I had one million from a friend and it was, at the end you always ask people who they're most grateful to.

Invest Like the Best with Patrick O'Shaughnessy
Cliff Sosin - Investing in Carvana - [Invest Like the Best, EP.421]

So I launched with $5.2 million. The old-fashioned way. It was $2 million from me because I'd been successful at UBS and they'd paid me. I like to joke it was a lot for post-crisis, not a lot pre-crisis. And I also got $2 million from my mom. She was a sympathetic audience. I had one million from a friend and it was, at the end you always ask people who they're most grateful to.

Invest Like the Best with Patrick O'Shaughnessy
Cliff Sosin - Investing in Carvana - [Invest Like the Best, EP.421]

I had two in mind and he's one of them. I'd known him for years and we talked and he's a very successful person and I had this meeting, it was like my second marketing meeting ever and I sit down and he basically is like, I'm absolutely gonna give you my dollars, no problem. And I was like, wow, this is gonna go great. The next time I saw a check like that, you know, it was years.

Invest Like the Best with Patrick O'Shaughnessy
Cliff Sosin - Investing in Carvana - [Invest Like the Best, EP.421]

I had two in mind and he's one of them. I'd known him for years and we talked and he's a very successful person and I had this meeting, it was like my second marketing meeting ever and I sit down and he basically is like, I'm absolutely gonna give you my dollars, no problem. And I was like, wow, this is gonna go great. The next time I saw a check like that, you know, it was years.