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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]

I'll talk about how it was super miserable, and it's pretty easy to imagine how it was super miserable. But it is worth just making a point. We were not fighting the Japanese in the Pacific. It sucked, but in the realm of human experience, I've lived a blessed life. I would say one way to think about it is there were two versions of me.

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

I'll talk about how it was super miserable, and it's pretty easy to imagine how it was super miserable. But it is worth just making a point. We were not fighting the Japanese in the Pacific. It sucked, but in the realm of human experience, I've lived a blessed life. I would say one way to think about it is there were two versions of me.

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

There was the me who you spoke to, who I think would sort of cogently say, well... There's this weird thing going on with rates and it can't last forever. And when it gets better, I think this will get better. And there was the me who was laying awake at night at 1 a.m. who was just kind of like, you know, my inner voice was not being kind to me. And I've always thought of myself as a person.

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

There was the me who you spoke to, who I think would sort of cogently say, well... There's this weird thing going on with rates and it can't last forever. And when it gets better, I think this will get better. And there was the me who was laying awake at night at 1 a.m. who was just kind of like, you know, my inner voice was not being kind to me. And I've always thought of myself as a person.

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

I think I am sort of naturally one of these people who has pretty good control over his inner monologue. And it was the first and only time in my life where I like lost control of my inner monologue. Like I, you know, would lay awake at night. I never lose sleep over monologues. things. I sleep and I would lay awake at night and I would, you know, fret and berate myself.

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

I think I am sort of naturally one of these people who has pretty good control over his inner monologue. And it was the first and only time in my life where I like lost control of my inner monologue. Like I, you know, would lay awake at night. I never lose sleep over monologues. things. I sleep and I would lay awake at night and I would, you know, fret and berate myself.

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

And it's super hard to live like that. But, you know, like again, it didn't have terminal cancer. I wasn't fighting the Japanese in the Pacific. Like it was, you know, within the realm of human experience. But like it is super difficult. And, you know, you've partners that you've let down. Right. And I mean, I say you've let them down as though you've let them down. Like, have you let them down?

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

And it's super hard to live like that. But, you know, like again, it didn't have terminal cancer. I wasn't fighting the Japanese in the Pacific. Like it was, you know, within the realm of human experience. But like it is super difficult. And, you know, you've partners that you've let down. Right. And I mean, I say you've let them down as though you've let them down. Like, have you let them down?

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

Like, your view of the world is that maybe you haven't let them down. It's just like, this is just a very big wave. But, like, then your partners would, you know, some, like, you got different responses. You know, I had some smaller partners who are no longer partners who, you know, were mean.

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

Like, your view of the world is that maybe you haven't let them down. It's just like, this is just a very big wave. But, like, then your partners would, you know, some, like, you got different responses. You know, I had some smaller partners who are no longer partners who, you know, were mean.

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

But, like, I had other, you know, partners who would very sensibly and totally appropriately, like, want to grill me about it. But that grilling didn't, wasn't, like, mean. It was totally reasonable. But, like, it didn't come from a place of confidence, right? You know, we'll eventually get to people I'm grateful for. But there was one partner who drove, you know, a long distance.

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

But, like, I had other, you know, partners who would very sensibly and totally appropriately, like, want to grill me about it. But that grilling didn't, wasn't, like, mean. It was totally reasonable. But, like, it didn't come from a place of confidence, right? You know, we'll eventually get to people I'm grateful for. But there was one partner who drove, you know, a long distance.

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

to have lunch with me. And it turns out that was the only reason they drove this long distance. And we get to lunch and it's like, this is not going to go great. These meetings haven't been going my way recently. And we sit down and he goes, Cliff, I'm just here to express my and everyone I work with's view that you're awesome. And, you know, you're going through a lot.

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

to have lunch with me. And it turns out that was the only reason they drove this long distance. And we get to lunch and it's like, this is not going to go great. These meetings haven't been going my way recently. And we sit down and he goes, Cliff, I'm just here to express my and everyone I work with's view that you're awesome. And, you know, you're going through a lot.

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

And I'm just here to say, like, you're great. We support you. Let us know if we can be helpful. But, like, we're Team Cliff. And I didn't cry, but I was like, wow. What a thing. And he's like, Neil, look, we're here for lunch. I drove here just to meet with you. We can talk about investing. Yeah, we can talk about other things. I don't really care. But this is what we're doing.

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

And I'm just here to say, like, you're great. We support you. Let us know if we can be helpful. But, like, we're Team Cliff. And I didn't cry, but I was like, wow. What a thing. And he's like, Neil, look, we're here for lunch. I drove here just to meet with you. We can talk about investing. Yeah, we can talk about other things. I don't really care. But this is what we're doing.

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

And I was just like, wow. And so that would be the other thing. To that day, and I think it makes me a better person because I remember how that affected me. Like the other day, there's a CEO in a company I'm involved in. He's wrongly getting a lot of crap. from really dumb investors. So I wrote him like, I sent him like a hug. Like I sent him like a nice, like a really nice email, I think.

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

And I was just like, wow. And so that would be the other thing. To that day, and I think it makes me a better person because I remember how that affected me. Like the other day, there's a CEO in a company I'm involved in. He's wrongly getting a lot of crap. from really dumb investors. So I wrote him like, I sent him like a hug. Like I sent him like a nice, like a really nice email, I think.

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

As nice as I could write it. But I think it makes me a better person to be on that side and to hear it and remember. So in terms of other things I'm grateful for, that would be another one. But you've let people down and you internalize that. And there's also this weird thing that happens where like,

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

As nice as I could write it. But I think it makes me a better person to be on that side and to hear it and remember. So in terms of other things I'm grateful for, that would be another one. But you've let people down and you internalize that. And there's also this weird thing that happens where like,