Dan Levitt is the founder and CEO of Long Haul Management. We discuss how Dan paid rent while making only $6,000 a year out of college (many side hustles), beating me in an office rap battle, Disney's big miss in digital music, executive producing one of YouTube's premium original series, and what it's like to represent some of the biggest sports and gamer personalities on the Internet.

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Chris Erwin:

Hi, I'm Chris Erwin. Welcome to The Come Up, a podcast that interviews entrepreneurs and leaders.

Dan Levitt:

I chose the safer Disney route. Again, I needed to pay the bills. But I made a promise to myself. Every day, I saw someone else doing what I wanted to do. They were the AbsolutePunks of the world. Or there were other people who turned the music blog into an A&R career, or leveraged it in other ways.

I'm good at seeing gaps in the marketplace and where could you go in it. I made a promise. The next time I see it, I'm fucking going for it.

Chris Erwin:

This week's episode features Dan Levitt, the founder and CEO of Long Haul Management. Dan grew up in Boston with an early love for music and yet-to-be-discovered bands. So, after wrapping a few acts in high school and interning at Philly radio stations during college, he kicked off his career by moving to LA with absolutely no job prospects.

But after a few A&R gigs at Columbia Records and Disney, Dan was early to see how digital and YouTube were going to transform the music industry. So, he left traditional media and kicked off his digital career, joining one of the early YouTube multichannel networks, company called Big Frame.

We actually worked together there. And in less than nine months, I actually had to lay him off. Dan struck out on his own, positioned himself as the YouTube guy for the music industry and started his own talent shop, Long Haul Management.

Some highlights of our chat include how Dan paid rent while making only $6,000 a year when he first moved to LA ... You'll crack up at some of his many side hustles ... when he beat me in an office rap battle, executive producing one of YouTube's premium original series, and what it's like to represent some of the biggest sports and gamer personalities on the internet. 

All right, let's get to it. Dan, thanks for being and the podcast.

Dan Levitt:

Thanks for having me.

Chris Erwin:

Awesome. I believe that you're a fellow East Coaster like myself. So tell me, where did you grow up?

Dan Levitt:

Sure, I'm from a nice suburb of Boston, Newton, Massachusetts. Literally voted safest city in America back when I was younger. So, nice Jewish suburb of Boston.

Chris Erwin:

Got it. It's funny. I went to underground at Tufts in Medford/Somerville. I think, while I was there, it was rated one of the most dangerous mafia-driven neighborhoods in the Northeast, or all of the US. So, quite the opposite of you. What was your household like? What were your family and parents doing?

Dan Levitt:

So, one, my parents are both from South Africa. They moved to the US in, I think, '77. My dad went to school for engineering, and then got a job in Boston, and then eventually started his own software business that really had a bunch of ups and downs. Mostly ups, and then fortunately sold to IBM right before the big bubble burst there. So, the timing was fortunate.

Dan Levitt:

And then my mom was artist. So, had all kinds of different things she would do in the art space, be it theater, be it actual prints and displays and stuff.

Chris Erwin:

Okay, very cool. It's funny. I've known you for about a decade and I had no idea your parents were from South Africa. Look, you're an entrepreneur. You've built out an incredible talent management firm. We're going to get to that in a bit. But you have entrepreneurial roots in your family.

Dan Levitt:

It's interesting now. I remember my dad would come back ... I think maybe at the height, he had 50, 60 people. Maybe more. I remember growing up, he'd come back from work and we'd be watching a Celtics game. It was the most exciting game ever, especially, they were really good back then.

Dan Levitt:

And he would fall asleep, and I'd be like, "How in the world can you possibly fall asleep during this game?" And now, I'm like, "Yep, I get it." Yeah, I could totally get how you could be so wiped out the day that, no matter what is on TV, you're just out.

Dan Levitt:

I mean, what was really interesting is, my parents went through a kind of messy divorce. We don't need to get into that but that's a whole fun story. But what's interesting is, when they separated, he stayed with a friend for a bit. And he went from sleeping in the basement of a friend's house to selling his business to IBM in a year.

Dan Levitt:

There were a lot of times that people told him, because the business had some challenges over the years, there were a lot of people that told him that he should declare bankruptcy with the business. But he stayed with it. And eventually, it worked out for him. I'm sure, hopefully, some of the resiliency I have, learned from him.

Chris Erwin:

Wow. Awesome. I have to ask. Being from Boston, a lot of media professionals from Boston have a pretty strong Boston identity. I think of Dave Portnoy in Barstool Sports, and Bill Simmons from The Ringer. Do you think of yourself like that, or your total West Coast transplant now?

Dan Levitt:

It's not just specific to Boston, but especially in the Northeast, there's a certain intensity and, I think, an edge that you can have, where in Boston, in traffic, if someone cuts you off, you scream at each other. And that's just acceptable and that's how you vent, right?

Dan Levitt:

In LA, it's much different than that. I'm in LA now. On the West Coast, people are more scared of confrontation. If you scream at someone, that's a really big deal. I think there's just a certain firm mentality that you have where it's pretty hard to bother me or get under my skin.

Dan Levitt:

I have thick skin. I do think part of that is just growing up in a culture where people are so up front with that. I also think, to a certain extent, growing up in cold climate where the weather is pretty brutal, and you just have to plow through it, does give some sort of mental toughness.

Chris Erwin:

I think that's totally right. I think there's this saying. I hope I'm not butchering it. But it's, "In New York, when people are saying, 'Fuck you,' they're saying, 'Good morning.' In the West Coast, when they say, 'Good morning,' they're saying, 'Fuck you.'"

Dan Levitt:

Yeah. I mean, but it's more so ... I remember in one of my first PA jobs in LA, I had a disagreement with another PA about the way things should be done. And then later on, I was brought into the office by my supervisor and they're like, "Dan, you were screaming at them. Why?"

Dan Levitt:

And I was like, "I wasn't screaming at them. I was telling them something they didn't want to hear in a certain tone. If I was screaming at them, they would know. Everybody would know." So, that was really the first ... I just moved to LA and I was like, "Shit, I got to really be cognizant of how I talk to people out here. They're going to think I'm a fucking lunatic," which, to a certain extent, is true. But maybe I need to slow play that a bit. Keep my response-

Chris Erwin:

It's part of your je ne sais quoi, as they say. Nothing-

Dan Levitt:

Yeah. I mean, you know me really well. But for people who just meet me, I can be a lot.

Chris Erwin:

Yeah, so let's actually talk about how you got to where you are today. I think, trying to get a sense of, was there a glimpse in your early days of you entering entertainment, becoming a talent manager? I think about things that you had mentioned that you were looking at unsigned bands in high school in the '90s. Tell me about that.

Dan Levitt:

My skillset is, I'm really good at seeing patterns and seeing where things are going, right? Before they get there. So, I think that's what I'm best at, be it entertainment or trends. I've done okay in the stock market, investing and stuff. So, specific to your question, yeah.

Dan Levitt:

My first real strong passion was music. I heard Green Day and it changed my life. And I was like, "This is it." And then I definitely have the personality type where if I'm into something, I'm all the way fucking in. So, if I like Green Day, okay, I need ever record they've ever had.

Dan Levitt:

So, I started, the mid '90s or so, music was starting to shift to digital, right? So, you used to discover bands on the radio, and then around that time, there started to be primitive websites. Around when Napster first came out, there started to be people who would put MP3s online, right?

Dan Levitt:

So, now here are these blogs that are hosting MP3s. So, they would be posting bands that would be signed to record labels. And I would like these bands. I'd find then, I'd like them, and then t