Chas Lacaillade — Founder of Bottle Rocket Management on $5,000 Startup Loans, Jerry Maguire Moments, and the Digital Video Revolution

Chas Lacaillade is the founder and CEO of Bottle Rocket Management. Chas took a big bet on the digital video revolution, and now builds businesses for some of the most exciting creative talent from New Hollywood. We discuss why he left a prestigious talent agency to sell water pumps, Louisiana roadtrips, and how he converted a $5,000 bank loan into a multi-million dollar business. Full episode transcript is below.  

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EPISODE TRANSCRIPT

Chris Erwin:

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

Chas Lacaillade:

I had my Jerry Maguire moment where I called all my clients and said, "Am I your manager? Am I your manager? And if so, this is my new endeavor, I'm going out on my own." It was terrifying. I took out a $5,000 loan from Chase Bank to live, and there was no interest for the first 18 months.

Chris Erwin:

This week's episode features Chas Lacaillade. Chas took a big bet on the digital video revolution, and now he builds businesses for some of the most exciting creative talent from New Hollywood. Yet Chas's career has a lot of twists and turns, and includes a lot of early disillusionment to be honest, like when he left a prestigious Hollywood talent agency to sell water pumps. But Chas's ambition eventually pays off. A Louisiana road-trip inspires a new career and soon after he turns a $5,000 bank loan into a multi-million dollar business. So Chas is a close friend of mine, and he's known for telling you like it is. It makes for fun listening. All right, let's get into it.

Chris Erwin:

Quick heads up, that my interview with Chas was recorded back in December and prior to COVID. Chas, welcome to the podcast.

Chas Lacaillade:

Great being here.

Chris Erwin:

Before we go through your entire entertainment story which is an impressive one, let's talk about some of your early days. Where did you grow up?

Chas Lacaillade:

I grew up in Lincoln Park, a neighborhood in Chicago which is very picturesque, very walkable. I attended schools in the neighborhood. All my friends lived in the neighborhood and it was great. I just had a really magical childhood, to be honest. I walked through Lincoln Park to my school, on winter days I'd walk through this enchanting, snow-covered park back home from school, and I'd have lots of time to review what I'd experienced that day, and what was going on in my life, and what I wanted to do. And I think that meditative time was really helpful for me in getting in tune with my thoughts because your teenage years are so frantic, and there's so much insecurity. You know, it took me about 40 minutes to get home probably, or between 30 and 40 minutes to walk home from school, and so-

Chris Erwin:

"Up hill both ways-"

Chas Lacaillade:

Yeah.

Chris Erwin:

... as my father used to say. He was also from Chicago-

Chas Lacaillade:

Yeah.

Chris Erwin:

... which was considered a pretty flat neighborhood overall.

Chas Lacaillade:

Yeah, and dodging crossfire from enemy combatants. And so, just walking home gave me some contemplative time, it was very therapeutic, that probably a lot of kids don't get.

Chris Erwin:

So in these meditative moments, were you thinking about your future career and that you were planning to start something, or was it more of like the whimsical child fantasies and fun back in the day?

Chas Lacaillade:

Well, I was a big reader as a child, so I read a lot of fiction and nonfiction, and I consumed a lot of biographies from basically, the age I could start reading. And biographies on a really wide range of people. So I remember when I was 12, reading Muhammad Ali's biography, and then Ayatollah Khomeini's biography.

Chris Erwin:

Wow.

Chas Lacaillade:

Just a real span of people because I was interested in a lot of different points of view, and the more I became exposed to what was out there and the different ways to obtain leadership, and fame, and infamy, and repute, and accomplishment, the more I became fascinated with what was possible if you just created a path for yourself.

Chris Erwin:

Yeah.

Chas Lacaillade:

And so, a lot of my thoughts were dedicated just to reviewing what these people who really impressed me, how they got to where they did. And how I could chart a path for myself that would employ my personal interests, that could hopefully some day lead to me being successful and known.

Chris Erwin:

Through many of our conversations over the years, there's a strong sense that you are highly ambitious, and that you really strive to overcome challenge. And I know that you often share with me, different biographical stories from magazines, something that you're reading in Esquire or GQ, or we will compare notes about Shackleton's journey to the Arctic.

Chas Lacaillade:

Yeah. Yeah.

Chris Erwin:

And I think these stories really resonate with you. I see this as a precursor to starting Bottle Rocket dating back 15, 20 years. Was there entrepreneurs in your family, your mother and father, siblings?

Chas Lacaillade:

Touching on what you were saying about these people that I've always been very impressed by, fortunately my parents exposed me to a lot of different ways of life. And I remember visiting William Randolph Hearst's mansion and just being so blown away by the scope of what this guy built, and how he lived, and his lifestyle, and the indoor pool and the outdoor pool. And all the art and architecture that he had imported from around the world, and how he'd customized this lifestyle. And so, I was so thrilled by that ambiance and the glamor of it. You know, how could I not be curious about how he provided this, and how he made this possible for himself? And so that lead me to familiarize myself with his accomplishments. And so once you know who somebody is and how they did it, and in this case he was very entrepreneurial, right? He created a newspaper empire and there's little he wouldn't do in order to achieve success.

Chas Lacaillade:

And so exposure to things like his mansion, or The Breakers in Rhode Island, and Providence, Rhode Island. I would go tour the Vanderbilt's mansions with my family in Rhode Island too. So just, I got exposure to these really impressive families. And my parents, my mother and father, would tell me how Cornelius Vanderbilt made his fortune, how he created a shipping empire. Or how Randolph Hearst created a newspaper empire.

Chris Erwin:

It's essentially made these stories accessible to you.

Chas Lacaillade:

Yeah.

Chris Erwin:

They grounded them in saying, "These are normal people-"

Chas Lacaillade:

Right.

Chris Erwin:

... "just like you and I, and so this is attainable if you have the spirit, and the intent, and drive to make it happen."

Chas Lacaillade:

Right.

Chris Erwin:

Is that like what you're processing of these stories and exposure?

Chas Lacaillade:

That's how I internalized it. It was also just like, "This is a pretty fascinating place. It's basically a museum, it's also a house. And it's indicative of a lifestyle that is pretty much bygone." And different people are going to take that in differently, but the way I interpreted the whole experience on all those occasions was like, "This is what's out there. If they did it, you can do it."

Chris Erwin:

I like that. Instead of looking at it and saying, "Oh, I can never achieve that," and then there's pangs of jealousy and frustration, it's, "Wow, if I hold myself big, there's incredible opportunity in front of me."

Chas Lacaillade:

Yeah.

Chris Erwin:

So let's fast forward. You find yourself in LA in 2006, and you're starting as an agent trainee at ICM Partners. So, what lead to the decision to join entertainment, overseeing and representing talent? Did you perceive it as, "This is the way to pursue your big ambitions"? Or, "Hey, this is just a key building block in learning, and I have a structured trajectory that I'm planning"? What was that thought process?

Chas Lacaillade:

Well, I'd always been really enamored with the world of entertainment, and Hollywood, music, they are areas that have fascinated me from a very young age. Consumed movies, and television, and music at a very high volume ever since I could remember, because I had an older brother and sister who could turn me on to different artists, and actors, and directors, and writers. So I felt like that was the path for me, and so basically I started my career out in an advertising agency in New York. Basical