From organizing jam-band afterparties in a Vermont college town to presiding over one of the top booking agencies in the world, Wasserman Music President Lee Anderson has always been driven by live music’s ability to entertain and inspire.

At Wasserman, where he reps Skrillex and such fellow dance-music titans as Disclosure and Zedd, Anderson has helped shepherd the nascent company through its evolution from Paradigm into a powerhouse that represents Kendrick Lamar, Drake, SZA, Coldplay, Ed Sheeran, Chappell Roan and Kenny Chesney, among others. Wasserman has also become a magnet for high-profile agents, as evidenced by the arrival earlier this year of former WME execs Kevin Shivers, James Rubin and Cristina Baxter, who collectively work with Tyler, the Creator, Travis Scott, Kali Uchis and Lil Baby.

In advance of Anderson’s one-year anniversary as honcho and the 2025 edition of Coachella—where Wasserman counts more acts than any other agency for a fourth consecutive year—the 43-year-old Phish freak was kind enough to field some mush-brained inquiries from HITS.

You have played a major role in elevating dance music to the place it is today. What was it like trying to book tours for those artists in the early 2000s compared to now, when many of them are stadium acts?
I grew up in West Hartford, Connecticut and went to school in Burlington, Vermont. My two favorite artists of all time are Jay-Z and Phish. Prior to being an agent, I had my own concert production company in Burlington. We started doing shows from Philly to Montreal and every college market in between. I basically invented the Disco Biscuits after party, and through that, I started to learn a bit about electronic music. I did a Bassnectar show during Burlington's Jazz Fest. When I originally started in the business, I interned for a guy named Alex Chaykin, who was the talent buyer at Nectar's and Metronome. Alex left and he ended up at an electronic agency in New York, AM Only. They didn't even call it EDM back then.

When I joined Alex and AM Only, I was the 11th employee. It was a couple years before Daft Punk did the pyramid, and I worked on a lot of the electro house stuff. My boss at the time, Paul Morris, repped David Guetta. Electro house was more hipster—Kid Cudi, Kid Sister, MGMT. I was living in Williamsburg, so I would deal with Webster Hall on Friday nights, which was East Village and NYU kids in dunks and leather jackets listening to electronic music.

This was also the infancy of digital marketing, which in the early 2000s was copying and pasting HTML onto a MySpace wall. I had amassed this large national street team, so I was able to find this niche where, instead of paying $2,000 for two full-page ads in alt weeklies in Boston, pay me three grand and I'll run a digital campaign, but you’ve got to give me six or eight markets. I was doing that for Waukarusa, Lollapalooza and Camp Bisco. I met a lot of people in the business and I also had a reputation of being able to execute live as a promoter. The people who I worked with were coming out of the rave world. You'd go to Disco Donnie and he would get you 28 tours. You weren't going to the local Live Nation, AEG or Another Planet guy.

If you’re of my generation, you either went to Warped Tour or were on the jam bandwagon. I was trying to bring traditional touring models to the electronic world. Paul had done some Tiësto bus tours along the way, but I was churning out 42-day tours where you’d play Boulder on a Tuesday and Madison on a Thursday. I signed Skrillex, and that was like a rocket ship. You're getting Rolling Stone covers and invites to the Clive Davis party. From there, I built the Zedds and the Disclosures.

We were acquired 50% by Paradigm and I got to work with Chip Hooper very closely. He became a mentor and a close friend. Same with Marty Diamond. I got added to the executive team after Chip passed. Ultimately, Marty took the lead on it, but I was able to be part of that team and help apply modern management practices.

Is it fair to say the notion of Skrillex as a festival headliner wasn't top of mind when you started working together?
When I signed him, his first gigs were for $250. I was working on Zedd’s "Clarity" on my sofa in a total shithole apartment off the Grand stop in Brooklyn. I started all those acts at Glasslands or Mercury Lounge, but some built faster than others. Skrillex is one of the fastest building acts I've ever worked with.

I’m Doing arenas in 2023 with the combination of Skrillex, Four Tet and Fred again.. was pretty groundbreaking.
In particular when you announce them two days out!

How were you able to be so nimble and still sell so many tickets?
The three of them had done these warm-up shows that January together, which were underplays in London. Then they wanted to do Madison Square Garden. I asked Josh Moore from Bowery Presents and Stacie George from Live Nation if they would do it together, because I wanted all hands on deck for something this unconventional. I give kudos to them for the work they did, and a major high five to [MSG SVP of Bookings] Randy Fibiger for trusting it.

Then, the slot became available on Coachella [after Frank Ocean canceled]. They were in a bit of a pickle. I got a call six days out from that weekend. We were able to get Skrillex to jet down from L.A. He walked the grounds, called the guys and said, we can do this. It was pretty epic.

What are some keys that have helped EDM become such a force in the live space?
When I was young, kids who went to raves had JNCOs on and gauge earrings. Ketamine was a thing. In the late 2000s/early 2010s, the producer started to step out as the artist. All of the sudden, they had Ariana Grande features, which gave them star power. It felt new for the valedictorian and captain of the football team to be out at these shows wearing neon. Also, a dance show is an experience, particularly in unconventional venues and unique one-offs.

We're coming up on a year of your presidential tenure and Wasserman is turning four. What are some leaps that you've seen the company take?
We started in April 2021 with 131 employees. We grew significantly. Number one, touring’s back, so you've got the revenue and you're able to hire support staff. Number two, we finalized the deal with our U.K. office, which is about 125 people. Those contribute to the growth, but beyond that, we set out to simplify the agency business with a couple of north stars. We want to be the best place to work. Let's be transparent. If we're going to make a new hire, let's tell our entire staff about it before it comes out in HITS. When you do that, people feel like they understand the strategy, what they're working towards and what they're a part of. That keeps morale and efficiency up, and it builds some pride. We constantly work to help people in their careers.

Also, the way you get paid. You're not working in a territorial system where it's like, oh, here's your salary and I think you're worth this. If you're an agent. you earn your money and you know how. If you work in a booking department or a service department, there are triggers and metrics that determine how you get paid, and you see those as well. Things like that go a long way towards building a company that people want to work at. It has led to attracting a lot of agents to come over, although we've probably said no to more agents than we've said yes.

Wasserman has a really large brands and properties business. Within that is a 100-person-plus research and insights development team which is great with data. It yields better results in brand partnership deals. We’re able to pitch some of those high-visibility platforms, like the NBA All-Star Weekend, that people are looking for, particularly around album campaigns. Clients are relying on agents way more than they ever have.

We are obviously adding agents, but probably 85% of our new hires are based around super-serving clients outside of traditional touring. That could be in our casinos and performing arts departments. It could be in colleges, corporates and privates. We launched an orchestral division with a couple of great agents in the space who can take Disney properties and tour them. When you apply that to a contemporary artist like John Legend, Zedd, Bob Weir or Trey Anastasio, that’s a cool way for them to have a different creative outlet.

We've been building out a really robust agent services division with specialists across digital, gaming, social, working with the DSPs and data aggregation. We’re trying to build the future of the agency, and that's geared around what our clients and their teams are asking us for. Today, we have 440 employees globally, so we've about tripled in size in four years, which is remarkable. People want to be a part of what we’re doing.

That speaks to people like Kevin, James and Cristina wanting to come to Wasserman.
We were honored they wanted to come and are proud to have them working here.

Kevin told me he appreciates that you’re involving him in things that might be outside of the normal purview of an agent.
Career growth lasts forever. There's a big premium put on getting an assistant to a coordinator or a coordinator to an agent, but I just had a chat with a 53-year-old SVP about how to get to an executive level, and areas that they could grow in. That matters. The Gen Z and millennial population don't want bosses. They want leaders.

That would go for anybody in our executive group, whether it's Corrie Martin, Marty Diamond, Jonathan Levine, Brent Smith, Kevin and James, Sam Hunt or Jackie Nalpant. I really never try to be a boss. I try to approach it like playing point guard and facilitating the offense to make sure a lot of different people are scoring and we’re winning games.

Festival saturation is always a topic of conversation this time of year. What are your thoughts on the state of that part of the business?
You've got some established mega brands. In North America, there’s Lollapalooza, ACL, Coachella, Outside Lands, Osheaga and Governors Ball. Those buyers have the most pressure. Those are hard to book and you've got to get it right early. It’s risky to be a promoter right now. Insurance costs are very high. Many agents can be a total pain in the ass. You’ve got to deal with weather, too.

What I am seeing emerge are the more curated festivals, like Kilby Block Party, Portola, III Points and Arc in Chicago. You're not going too big, but it's big enough where there’s a great community and your artist could play a big set there. I'm seeing it internationally as well. Australia went through a rough patch, but they figured it out. Latin American festivals are performing well. So are European festivals.

I know that Governors Ball is having a great year. Last year, Lollapalooza had its biggest on-sale of all time. Coachella’s in really good shape. Festivals are important, but they became cookie-cutter and there were too many. Now, we're whittled down to the significant ones that have been there and will stay, and some of these niche-level, 30k- to 40k-person events are doing well. CRSSD is an amazing example. The guy behind it applied a model to dance music that he’s been successful with in booking country and Americana at Big Sky in Montana. I think that’s the sweet spot. Honestly, I think it's good for the touring business to not be oversaturated with so many festivals.

On a similar note, stadium business is booming for everyone from Oasis to Kendrick Lamar and SZA.
The market cap for a lot of music fans is growing. We’ve got a bigger audience of people who want to attend concerts now, which has made it more feasible for artists to get to stadiums at an early level.

It used to be that Lollapalooza would pay a headliner a million-and-a-half, two million bucks, which was more money than they would make in an arena. Now with the sophistication of the ticketing platforms and dynamic pricing, you can capture more of the gross without a lot of it going on secondary. Instead of Lollapalooza, I can do two United Centers at a million-and-a-half a night. And by the way, that's a stepping stone because I want to get to Soldier Field.

I’ve heard some fascinating rumors about how the Oasis tour was planned without news of it ever leaking.
I have no comment.

Beyond the superstars, are you seeing anyone who could rise to a stadium level before too long?
Tyler, the Creator just did five Cryptos. He feels like an act that can get there. Kendrick and SZA are already there. Olivia Rodriguez, Dua Lipa and Sabrina Carpenter are doing big business.

What has it been like working with Casey Wasserman?
He's incredible. I could not feel more fortunate or more proud to work for him. Casey is unbelievably well connected. I don't understand how he deals with everything he does during the day, because it doesn't matter who you are on the music team—if you reach out to him and ask him for something, he is all over it and will not stop until it's done. Through him, I have grown 10 times in terms of my understanding of business. Anytime I’ve asked him to help connect me with someone, it’s done in 30 minutes, whether that's putting Fred again.. onto a text with Tim Cook or connecting me with Daniel Ek.

He doesn't sit in an ivory tower. He's in the mix. He's at a ton of shows, constantly checking in. Just a tenacious professional. The culture of the whole organization really starts with him: be good people, make a positive impact in your communities and industries, have a relentless pursuit of excellence and always try to improve and grow.

It’s unclear what’s going to happen with the Live Nation/Department of Justice investigation, but do you think splitting up Live Nation and Ticketmaster would provide some tangible benefits to the consumer and the industry?
Live Nation runs a really smart business. Everyone I know there is unbelievably proud. There are not many organizations where the staff refers to their boss by his first name.

A lot of the DOJ stuff is based around free-market competition on ticketing, and it's a complex web. I do a ton of business with Live Nation and I've never felt like anything I've done with them has been unfair. I don't look at Live Nation as the evil empire. I look at them as great partners and people who are very passionate about music.

You've addressed what you think is working in the biz at the moment. What might be a stumbling block or two that you would like to see dislodged or tipped over?
Expenses are really high. Artists want to build shows that look like they're the second coming of Jesus Christ. We're focused on helping to make sure the margins are okay and the budgets are there. Buses cost more. LEDs cost more. You don't want to just pass that down to the consumer. We pay attention to the elasticity of pricing, and we never want to gouge people. A lot of artists are operating on a 15 to 20% profit margin. Every business manager will say, let's shoot for 30%, but it's hard to deliver.

I'd love to see merch become a little bit easier, where you buy it there and it shows up at your house. Every promoter, ticketing company, agent, fan and musician hopes that we can find a way to combat bots. I wish that there were more grants out of certain nations to help their talent and artists be a national export. Canada does this incredibly well. But if you're a developing act based in Chicago and you can sell a thousand tickets a night in Australia, it’s hard to get there to make it make sense.

I'd like to see people in the industry have a bit more transparency on their compensation. I'm not saying you’ve got to raise salaries everywhere, but it's important that people know how they get paid on their work. I hope the premium we put on transparency and career growth shakes up the industry and creates change across this business. A lot of companies are well-oiled machines, but I wish people would try to figure out how you build those based on your staff from the bottom up. For anyone who says it's not possible, I would say, look at our company.