The HITS Interview: Casey Wasserman

Seated at a conference table on the 12th floor of the gleaming Westwood office building that bears his famous surname, Casey Wasserman is strikingly relaxed for a man who, when not running one of the leading talent agencies in town, has a particularly nerve-rattling side hustle: chairman of the organizing committee for the 2028 L.A. Summer Olympic Games.

Casey is the grandson of the late Lew Wasserman, the former chairman and chief executive of MCA, whom the New York Times lionized as “The Last of Hollywood's Moguls,” which somehow underplayed his outsized role in the creation of the modern movie and television business. Raised primarily by Lew and his wife, Edie, Casey broke onto the scene as a wheeler-dealer in the sports world, where today his titular agency is a dominant force, representing hundreds of star athletes in all major sports.

In 2021, in the midst of the COVID pandemic, Wasserman made a bold move into the music space, purchasing Paradigm Talent Agency’s live music business, which included such top agents as Marty Diamond and Lee Anderson and such A-list concert draws as Ed Sheeran, Billie Eilish (who’d later move to WME), Coldplay (in North America) and Imagine Dragons. Since the acquisition, Wasserman Music has aggressively bolstered its hip-hop and R&B presence, snatching agents Kevin Shivers, Brent Smith and James Rubin from its rivals and adding Kendrick Lamar, SZA, Drake (now with CAA), Tyler, the Creator and Travis Scott to a roster that also includes BLACKPINK, Chappell Roan, Noah Kahan, RAYE, Kenny Chesney, Fred Again.., My Chemical Romance and The Lumineers. Wasserman is a firm believer in scale, which is borne out by this year’s Coachella, for which Team Wass represents nearly one third of the artists booked to perform, more than double the number of its closest competitor.

The night before we meet, Wasserman mingled at a Golden Globes after-party celebrating host Nikki Glaser, a management client from his company's 2023 acquisition of Brillstein Entertainment Partners. But of all his high-profile gigs, none is more pressurized or open to public scrutiny than chairing LA 28. Beyond the logistical nightmare of organizing the Summer Olympics in his hometown, Wasserman, a lifelong Democrat, must work closely with President Trump, whose virulent anti-immigrant rhetoric and deportation raids enacted in L.A. and elsewhere prompted calls by some for the games to be moved. Wasserman notes that since 1980, every Olympics held in the U.S. has had a White House Task Force, and thus Trump’s role as head of said force is not wholly unique; for his part, Trump called Wasserman “a very nice guy” in a recent interview with the New York Post.

That’s what’s known as a blessing and a curse, as is talking to this trade rag.

How’s business these days?

Our music business is really good. It's hard to imagine buying a business in the middle of COVID and it turning out to be the greatest gift.

Did you buy low, as they say?

We made a good deal. We took a risk that a lot of people weren't willing to take at the time. With Paradigm, we bought an incredible group of agents, but not a cohesive culture. COVID allowed us not just to do the deal, but to redo all of the agents' contracts who came over. Prior, even though they operated under the Paradigm name, they were all kind of separate. The new deal created an alignment among them.

Then the business rebounded a lot quicker than we thought, and we were prepared. The combination of getting the culture right, investing in the business and the overall comeback of the live business has made the last few years a really fun ride.

What’s involved in getting the culture right?

When you start in the sports business like we did on the representation side, essentially every 10 years you lose 100% of your clients because their careers are over. You can have one good run, but if you don't have a good culture and good people, you won't get more. When you have those, you can build sustainability. Our mindset is about the people and the culture. We have never bought client lists in the history of this company. We better be the best place for our agents and managers to work. We better be the best place for them to monetize their career. Anything we do that gets in the way of those things hurts our culture.

Our mindset is about the people and the culture. We better be the best place for our agents and managers to work. We better be the best place for them to monetize their career. Anything we do that gets in the way of those things hurts our culture.

Is the music space particularly volatile these days?

I don't know that it's more volatile than others, but it's more transactional by the nature of booking tours. With sports, you do deals for a lot of money over a long period of time. Music is a tour-to-tour business. I would say it’s transactional, not volatile, because when you have scale, it smooths out the ups and downs of the business.

You have so many things that you're overseeing. Are you happy with the amount of time you get to spend with the music people?

It's not about quantity of time. I'm a resource to the people who work here. If an agent calls me and asks for help—"Can you call this manager? Can you call this executive at a company?"—I always do it. I can be helpful, I will do anything I can to be involved.

Didn’t you start a music agency in the early 2000s?

No. We hired Dave Holmes in the old days when he worked at Nettwerk and managed Coldplay. David came over, he brought Coldplay, and they had this idea to do what today you would call a festival. We were going to support it financially and help generate sponsorship revenue. In the end, it wasn't right for the band at the time, and Dave ultimately wasn't comfortable being in a company. We were really young then. I would be shocked if we were a hundred employees before Dave Holmes.

How many are you now?

We're 4,000.

How long have you been cogitating on being in the live music space?

A long time. Look, the two things that matter live are sports and music. We’ve learned that we’re really good when we operate at scale. In the music business, the only way to operate at scale is to be an agent. Managers by definition don't operate at scale, they operate in a very bespoke way with a hands-on relationship with a client. Agents by definition operate at scale. And so we realized that being an agency was where we should be. To be fair, we tried to buy Paradigm for three years. I would go see [Paradigm chairman] Sam Gores every week, every other week, once a month, just relentlessly trying to convince him to sell us Paradigm and then we could spin out the music business. We could never get traction. When COVID happened, it changed overnight.

Did you eyeball any other agencies in the process?

No. For whatever reason, when we've bought small or singular businesses in highly competitive businesses with scale, we have not done well. When we’ve bought medium-sized businesses with big competitors, we've done really well. Twenty years ago, we hired a great golf agent who had some great golfers, and we thought we could build a golf business around it. It was not successful. A few years later, we bought a medium-sized golf agency and now we're the biggest golf agency in the world. We’re really good at taking something that's got some heft to it and growing it.

Everyone I talk to in the live business says "we’re in a gold rush, we’re the cash cow of the music space." Given that, what are the headwinds that could derail that momentum?

Roughly 85% of an artist's earnings now come from touring. That means there's a lot more people on the road, which means there's a lot more artists and concerts asking fans to part with their money.

This seems to be a problem in the festival business.

Correct. When we're asking people to part with discretionary dollars, we have to be cognizant of the general state of the economy. Overpricing and oversaturation in a K-shaped economy would be a bad combination. You have to be intentional about where you're going, why you're going there, how many seats you're playing, what your pricing is, all those things, to make sure you don't get out over your skis.

Left, Kendrick Lamar on his record-setting Grand National tour; right, Chappell Roan at Lollapalooza in Chicago, 2024

Let’s shift subjects a bit. What’s the first concert you remember attending?

The first concert I attended with my grandparents was Frank Sinatra at the Universal Amphitheater.

Once I got a car, I could go on my own. I’ll never forget going to see Jane's Addiction at Universal Amphitheater, and Jay Marciano, who ran it at the time and is still a great friend, nearly had a heart attack when I showed up. He told me I didn't really understand what the crowd was like in the mosh pit. He was horrified that if something happened to me, my grandfather was going to fire him!

When I was 16, my grandfather’s company, MCA, bought Geffen Records. This was the height of Guns N' Roses. A couple of years later, they toured with Metallica and played the Rose Bowl. I used to call my grandfather's office and ask for concert tickets. This time he said, "If you want tickets to Guns N' Roses, call David Geffen yourself." And he hung up. So I called the main number there. “It's Casey Wasserman. Is Mr. Geffen there?" A few seconds later, Dave picks up. Thank God he couldn't see me because I was so nervous, I was sweating profusely. He said, "What do you want?" And I said, "Guns N' Roses, the Rose Bowl." He goes, "You want tickets to go to Guns N' Roses?" "Uh, yes." "How many do you want?" I go, "Eight?" He goes, “Come to my office tomorrow. Goodbye."

Rolling deep. Eight tickets.

If you're going to ask, you might as well not be shy. So me and seven buddies, we go to the Rose Bowl, and we keep showing the attendants our tickets. They're like, "I don't know where those are." So we're on the floor, walking and walking. Turns out, David had them put eight seats in front of the front row for us. Guns N’ Roses pretty much sweated on my head for three hours.

You've mentioned David Geffen and Jay Marciano. Who are some other people in the music biz you admire?

I have incredible respect, admiration and fondness for Lucian [Grainge]. The way he has managed and built that business is remarkable. And we both like Arsenal, so that's a good thing.

I've known Irving [Azoff] since I was 10 years old, when my grandfather bought Front Line Management. [In 1986, MCA purchased Front Line along with Full Moon Records, both of which were majority owned by Azoff, who was president of MCA Records at the time.] In many ways, Irving was a surrogate father to me because I didn't really have a traditional... I didn't really have a dad. My grandfather served that role, but I grew up around the Azoff family. There's nobody who's had a more remarkable and diverse career in music. A lot of people can do one thing well. He's done a lot of things incredibly well.

Did your grandfather like the music business?

He did. He especially liked the touring business. He liked live events. Whether it was music touring, theme parks or building the Universal Amphitheater, he understood the power of those things.

I've heard you talk about what you learned from your grandfather. I'm curious, what did you learn from your grandmother, Edie?

She was an incredible woman. I tell people maybe the best piece of advice I've ever gotten from anyone is from my grandmother, who always said to me, "Even if you're right, you don't always have to be right." And there's probably not a day where I don't think about that. If I was in Los Angeles, I saw her every day. She outlived my grandfather by 10 years. Those years were pretty special because it was just me and her.

Was your mom in the picture?

My mom is Lew and Edie's only child. She had a complicated relationship with her parents, and I had a complicated relationship with her. I was much closer to my grandparents than I was my mom.

I read that you and Lew used to go to Nate ‘n Al’s every weekend, but I’ve heard conflicting accounts of your standard order. Can you set the breakfast record straight?

This is important stuff! When I was three, when my grandfather and I started going there every Saturday and Sunday, just the two of us. He would get me a bagel and cream cheese, and he would rip it up into little pieces. Then he would crinkle up bacon, and I would dunk the little pieces of bagel and cream cheese into the bacon.

Definitely not kosher.

No, but it was a very efficient way to get me fed. Then as I got older, I switched to matzo brei. Sweet, not savory, for the record.

Back to Wasserman Music, who are the execs leading the way there?

Marty Diamond, whom I met when I hired Dave Holmes, has been a friend for a long time. He still has Ed Sheeran and Coldplay, but he also continues to find great young talent like Tyla. It’s great to see someone who's had so much success continue to grow and develop. The leadership team that came over has thrived: Sam Hunt, Corrie Martin, Lee Anderson, Jonathan Levine. Adding Brent Smith, Kevin Shivers, James Rubin and Cristina Baxter was an incredible boost to our business. It gave us a breadth of leadership and elevated the younger generation of agents, too.

I know clients come and go at any agency. When a Drake or Billie Eilish leaves Wasserman, do you personally try to intervene and persuade them to stay?

I hate losing any client because that's how competitive I am, whether it's Drake or someone you've never heard of. Maybe that's not the healthiest thing…

Do you take it personally?

I'm almost not capable of distinguishing between personal and professional. So the answer is yes. Every client has different reasons for leaving. Drake is a pretty obvious situation given who else we represent [Kendrick Lamar]. In that case, it’s frustrating because you didn’t do anything wrong. The facts don't matter.

Did you try to talk Billie into staying?

I never talked to Billie. I tried to talk to her mom, but to no avail. People are entitled to do what they want. I'm not sure it's as simple as the story people would like to craft. I wish her and her family the best. She's obviously an incredible talent. I think I've proven myself to be magnanimous because after she left, I kept her on the LA 28 handover show [part of the closing ceremony of the Paris 2024 Summer Olympic Games]. I could have easily removed her, and no one would have known the difference, but she's an important star, important to L.A. Having her and FINNEAS perform on that was the right thing to do.

Are you going to the Winter Olympics in Milan?

I’ll be there for the beginning, then I’ll come back for the Super Bowl, then go to the NBA All-Star Game, and then go back to the Olympics, for both LA 28 and for business: We represent the captains of the U.S. and Canadian hockey teams, Auston Matthews and Connor McDavid.

When you visit the Winter Olympics, what are you hoping to learn?

First of all, the Summer Olympics is about 10 times larger than the Winter Olympics. So there are a lot of things that are not equivalent. But we'll send Peter Rice and Ben Winston to watch how they execute the opening ceremony. The Winter Olympics broadcast center is one of the few things that's probably close to the scale of the Summer Olympics. But look, they will sell a million-plus tickets. We'll sell 15 million tickets. They have seven sports, we have 36. The scale is way different.

What role will President Trump’s White House Task Force play in the planning of the games itself?

First off, there has been a White House Task Force for every Olympic Games in the United States going back to 1980. Mike Deaver, if you remember the name, was President Reagan's appointee. In '96, Vice President Gore was the head of the White House Task Force. So this is not a new thing.

Here’s the reason the Task Force is important. LA 28 will touch 36 federal agencies, from Defense to FCC to I.R.S. to State Department to Homeland. Without a task force, you can't have a unified engagement with the federal government. A task force creates an executive order to make sure that all the departments we touch have both a point person and a plan.

Case in point: The FCC had to give us more bandwidth, because there's not enough bandwidth in L.A. to handle the Olympic Games. The I.R.S. will change tax laws so that athletes don't get taxed for winning a medal. The State Department has to issue 250,000 visas. Imagine issuing a quarter-million visas in 30 days to 209 countries, 25 of which you don't have embassies in. Secret Service will manage and deliver the security operation for the Olympics. So the Task Force is a mechanism. There's a White House Task Force for the World Cup. There's a White House Task Force for America 250.

Without the money from the federal government, there's no Olympic Games in the United States of America. We’re the only developed country on earth where the government does not support the Olympic movement. We are a private 501(c)(3) responsible for delivering the biggest event in the history of the world. You obviously need the city of L.A., you need the state of California, but the federal government is by far our biggest economic supporter. We have a $2 billion request for transportation alone in this budget. We're doubling the size of LA Metro for 30 days. LA Metro doesn't have the money to do that. It only happens with the Department of Transportation.

How would you describe your conversations with President Trump?

Let me offer some perspective. For four years, I would regularly go to the White House and meet with the Biden administration, including the President, and beg him to announce the White House Task Force so we could get started on a lot of the work. I wanted this White House Task Force launched a long time ago, because the more time you have to plan, the more efficient you can be.

So why didn’t the Biden administration launch it?

Their view was that if they lost the 2020 election, it would be someone else's problem, and if they won, they would deal with it after the election. That's what they said for four years. They kicked the can.

Here is what I will say about President Trump. Everything we've asked this administration to do, they have done exactly how we've asked, without conditions. And in my role as chair of the Olympics, that is the only thing I could ask for.