Casey Wasserman has an app that reminds him how many days are left until the opening ceremony of the 2028 Summer Olympics in Los Angeles. Sitting in the Wasserman offices in a black hoodie, with framed artwork of the U.S. flag behind him, the 49-year-old sports and music executive checks his phone: just under 1,650 days until the LA28 campaign he is leading comes to fruition. “I’m not sure I knew I was signing up for a 14-year volunteer job,” he says, “but lo and behold, here we are.”

Almost a decade ago, Los Angeles Mayor Eric Garcetti called Wasserman asking for suggestions of who could spearhead the bid to bring the U.S. Olympic and Paralympic games to the Southern California metropolis. A few weeks later, Garcetti called him again: Those people weren’t going to work. He wanted Wasserman to take on the herculean task himself.

“I told him, ‘This is a hard thing to do in the best-case scenario — and, by the way, I have a job,’ ” Wasserman says. After another few weeks, the mayor rang him yet again: “I hate to do this to you, but I’m the mayor. It’s important to our city. You have to do this.”

In 2015, when Wasserman officially started the campaign to bring the Olympics to L.A., he was 13 years into building his sports and entertainment agency (at the time named Wasserman Media Group). But entertainment was in his DNA. The grandson of famed Hollywood talent agent and MCA president Lew Wasserman, the younger Wasserman learned the industry’s ropes from him, and says that while he deals in sports instead of film, he still plays out in his head on a daily basis the lessons his grandfather taught him.

Although MCA never owned sports rights, Wasserman’s grandparents were avid sports fans. He would join them in London in the summer while Lew worked across the pond. Once, at Wimbledon, Wasserman spotted Nike founder and businessman Phil Knight “in shorts and a polo shirt and a straw hat,” he recalls. “When I went to Wimbledon with my grandparents, we were in suits and ties.” He asked his grandfather to introduce them.

“I’m sure there were entertainment people there. That’s not who I wanted to meet,” says Wasserman, who claims he has never been star-struck by celebrities. “I wanted to meet Phil Knight.”

A self-professed “weird kid who liked the business side of sports,” Wasserman began his agency business in 2002, mere months after Lew died. One of his first acquisitions was The Familie, an action sports agency in Carlsbad, Calif. — not because he was a passionate skateboarder or snowboarder, but because he saw an untapped niche. “The X Games were relatively new, and there was an opportunity to buy a business that was a leader in its space — small, but a leader in its space — in a world that was growing,” he says. “Or more frankly, where the entrenched players weren’t.”

Since then, the Wasserman agency has made almost 40 acquisitions, including the major purchase of Paradigm’s music division in 2021, which brought a massive, multigenre roster including Coldplay, Billie Eilish, Janelle Monáe and Ed Sheeran under its purview. Now the company sits comfortably at the intersection of sports and music (as well as film and TV, following its 2023 acquisition of entertainment management and production company Brillstein Entertainment Partners) with clients ranging from Kendrick Lamar and Diplo to pro basketball stars Shai Gilgeous-Alexander and Brittney Griner. It’s an ideal position to be in as the chairperson of the LA28 board, eagerly watching the days tick down.

“Hopefully, all the way through to the closing ceremonies and the Paralympics, you will feel the authenticity of L.A.,” Wasserman says. “Which means a lot of star power, a lot of music.”

How will sports and entertainment overlap at the Olympics?

The Olympic Games in Los Angeles have to be authentic to who and what L.A. is, just like the Olympic Games in Paris will be authentic to what they are. We don’t have the Eiffel Tower. We don’t have Versailles. That’s why people say Paris is the most beautiful city in the world, because it probably is. But we’re the creative capital of the world. We have star power that no one else in the world has, and you’re going to see a lot of it.

Where did your love of sports come from?

I was born with an interest in sports. I’ve always loved the business of sports. Obviously, my family was in the entertainment industry, and I grew up being raised by my grandparents. They both loved watching sports. MCA Universal never owned anything in sports, but [my grandfather] had lots of friends in and around the sports business, so I got a lot of exposure to the sports world.

What did you learn from your grandfather, Lew Wasserman?

He wasn’t alive for the start of [my] business, but spending as much time as I did [with him] for as long as I did, I certainly heard a lot of stories. There literally isn’t a day that goes by where I don’t think about something or a story he told me and use it in my business or tell someone in my business something that I learned from him through storytelling.

Why did you decide to get into music in 2021 with the acquisition of Paradigm’s music division?

For us, if we were going to expand beyond the representation of athletes or talent in or around sports, music was always a logical extension because of the close connection: the relevance of those two businesses, their value as live events that matter in a world where not much else matters live. The crossover between sports and music, that’s sort of engendered in each other.

I tried to buy Paradigm for three years. I ­probably had drinks — not really drinks, but we’ll call them drinks — with [Paradigm founder] Sam Gores every other week roughly for two to three years. Never could break through. COVID happened, changed the world overnight, changed his business overnight, and [I] got a call from him and his brother, who was his investor, and [they] said, “We have to sell the music business, and you spend a lot of time in and around it, and we have to get this done.”

I think it was April 4, 2020. And 13 months later, we closed the deal. And we were in the music business.

What was the idea behind buying a live-music agency when live music was at a standstill?

Because we believe in the music business. We’re not buying it for tomorrow; we’re buying it for the next 100 years. We believe in the value of it and the power of it, to buy a business that had some of the best music agents in the world — I’m biased — and bring them together and invigorate them with culture and support and leadership and perspective and breath, which we’ve done since we owned it. It doesn’t matter whether you’re the biggest client we have or an act who’s playing in front of 10 people, we take every one of those seriously. Because for me, my name is on the door.

Do you have the same passion for music as you do for sports?

I love sports. I love watching sports on TV, no different than I like listening to music. But I love the business side of sports, and I love the business side of the music industry. Thankfully for us, I’m not the one deciding what artists we sign because, hopefully, that’s not my greatest contribution to the business. I am supporting our agents to the fullest extent so that they can do their job to the best of their abilities and therefore attract and maintain clients.

Do you meet a lot of athletes who want to get into music or musicians who want to get into sports?

People used to think that was a thing. That was always a false theory. Really simply, if you’re that big of an athlete and you’re that good of a musician, it doesn’t matter if you’re represented by the same person or not. And if you’re that good an athlete and you’re not that good a musician, it doesn’t matter who represents you. Agents don’t make things happen that aren’t supposed to happen. You can’t make someone what they aren’t.

The overlap is the skill sets we have across the company. With athletes, the entire sports industry is about brand association. Every sporting event has brands built into the presentation of the game — on the uniforms, off the court. It’s a core competency you have when you are a sports agent with the caliber and scale of clients and business we have. Now, in a time and place where those things are desired, we have a talent and a skill set that I don’t think our competitors have. We have produced extraordinary results for our musicians around brand deals.

It’s not that you’re going to make the best player in the NBA be the greatest musician in the world; it’s that the skill sets you have representing the best player in the NBA now apply to representing the best musician in the world and vice versa.

So you see someone like Shaquille O’Neal — NBA star turned DJ — as an anomaly?

Shaq is unique in a lot of ways. He’s a friend and someone who’s great to be around. But he’s got such a big personality. Anything he does, no one will be surprised. He’ll try and do anything. He’s fearless that way.

What about Oklahoma City Thunder’s Shai Gilgeous-Alexander, who’s reportedly recording in a studio?

Yeah, but those things are few and far between. That doesn’t mean the interest isn’t there. There has never been anyone who has had equal success [in music and sports]. What Shaq will earn as a DJ will pale in comparison with what he earned at his height playing basketball.

Why is there so much crossover between music and sports?

Sports and music matter live, so the ability to present them together can always be interesting and create value. At [Formula 1] race weekend in Las Vegas, we booked 40 performances — not 40 different artists — during the four days. You go to any sporting event in the world and when there’s a stop in play, music comes on over the speakers. That’s because music and sports are universal languages.

What is Wasserman’s strategy for business growth?

Well, we are in the service business, and service businesses are remarkably simple. They only grow in two ways: You get more revenue from the clients you have or revenue from new clients. That is it. As far as I can tell, the only ways to do those two things are to have more services for your clients or more geographies to serve them in. Our business is not complicated.

We are driven by nothing other than what we believe is in [our clients’] best interest. And today, that has proved to be a good formula for consistency and success and growth. That doesn’t mean we are static. We’ve done almost 40 acquisitions in 20 years, and we went from one person to 3,000 people. Clearly, we’re a business that’s growing.

Would Wasserman go public?

I’m fond of saying I’m absolutely horrible at two things: reading minds and predicting the future.

This story will appear in the Feb. 10, 2024, issue of Billboard.