This summer, Superfly co-founder Jonathan Mayers will celebrate a few significant milestones: 20 years since his company’s first show, 16 years of Bonnaroo, 10 years of Outside Lands and the launch of Colossal Clusterfest, a comedy-centric festival, featuring headliners Jerry Seinfeld and Kevin Hart. Mayers grew up an hour outside New York City and attended Tulane University, where he immersed himself in New Orleans’ rich musical culture. After graduating in 1995, Mayers worked with New Orleans institutions Tipitina’s and Jazz Fest, and he founded Superfly in 1996—the new company’s first official show was the Mardi Gras offering “Take Funk to Heaven” in 1997 at the Contemporary Arts Center with the funky Meters, Maceo Parker and Rebirth Brass Band. (The first date Mayers presented under the Superfly name was a May 1995 Tipitina’s show with George Porter Jr., Kermit Ruffins, The Wild Magnolias and Rebirth Brass Band.) From there, Mayers and his partners went on to create Bonnaroo and they have helped define the festival landscape for over 15 years.

You began seeing a lot of music and spending a lot of time at Tipitina’s while you were studying at Tulane. At that point, were you more interested in working in music or just going to shows?

At the time, I was unsure of what I wanted to do. I always had different entrepreneurial ventures and businesses going on. They weren’t related to music, but I knew that I wanted to have my own business. When I was in school, I interned at New Orleans Jazz Fest, and I was really inspired by the festival and the people working there. Around graduation, I thought maybe there was an opportunity to merge my interests in live music and events with being an entrepreneur.

What happened after graduation?

A lot of my friends left New Orleans, went back to wherever they were from and got “real jobs,” but I stayed in New Orleans and wound up booking Tipitina’s. At the time, this place that I loved and had all these amazing musical experiences at was falling on hard times— they were getting beat up by House of Blues, which had just recently opened in New Orleans about a year earlier. I had done one show at Tip’s around my college graduation, I got to know the people who owned it and they offered me a job. That’s why I wound up staying, and that’s when I really threw myself into this line of work.

Can you describe an early influence—an experience or individual—that made an impact on the trajectory of your career?

Quint Davis, Jazz Fest’s producer, was a big influence when I was an intern and someone who I looked up to—all the different talents he worked with, just his passion for what he was doing, his creative spirit. I remember peeking into his office and looking at all the concert posters on his wall and thinking, “I would like to have a concert poster from a show that I did.” It just felt very real. He was passionate and he was very creative. That spoke to me. Jazz Fest had such a profound effect on the community and the diversity of the community. I was just really inspired by that.

Can you talk about your transition from Tipitina’s to the genesis of Bonnaroo, and how you put that team together?

Around ‘96-‘97, there was a change in ownership at Tip’s, and I left and wound up getting a full-time position at Jazz Fest for about a year or so. During that time, I teamed up with my current partners: Rick [Farman], Rich [Goodstone] and Kerry [Black]. And we said, “While I’m working at Jazz Fest, let’s do some shows focused on Mardi Gras and Jazz Fest—kind of satellite shows.” I got permission from Jazz Fest, and we started booking.

We were always ambitious, and we put one foot in front of the other, thinking, “How can we make this sustainable? How can we grow this?” We didn’t have a master plan except that we were excited by the work, and we wanted to do it full time. Eventually, we had to make the choice of, “Do we want to take this leap to really focus on Superfly and make this a full-time thing?” And we decided to do it. That’s when we went beyond doing special events and we started promoting throughout the rest of the year.

It was a hard business model. We were coming into venues where we weren’t getting the bar—going into an established place and just working off the door and competing with all of the established clubs for talent. We were doing a lot of shows, but we weren’t making any money. We soon realized, “This is probably not the right business plan to sustain and grow.” We were thinking, “What can we do where people are going to sell us more talent, and let us have a platform to be creative and do something outside of the box?” That’s when we started thinking about doing a festival.

It was an interesting time in the live-music industry. A lot of the established, well-known promoters were getting wrapped up into SFX and becoming one company. We thought that maybe there was a lane for us to do something different. A lot of the bands we were working with at the time were bands that we loved in the jamband scene—the disciples of the Dead and Phish, these great touring bands that had devout followings. We thought, “Well, what if we brought all of those bands together in one place?”

What do you think made this attractive to Ashley Capps and Coran Capshaw, your Bonnaroo partners at the time?

Capps was an independent promoter. It was an opportunity for independent promoters to stand out and do something to counter what the rest of the industry was doing. There was an opportunity for us to be competitive, going into a field as opposed to going to major markets [where] there was now even more competition because it was concentrated under this umbrella. It was an opportunity for us and Capps to figure out our footing within this changing industry. That’s why it was appealing.

Capshaw is a serial entrepreneur who has always been on the innovative front, whether it’s Musictoday or the way that he manages bands, and he’s a calculated risk-taker. He has always been on the front end of taking smart chances—obviously with his work with Dave Matthews Band— and, being a fan of the Grateful Dead, he understood the strength of this community and a new way of thinking about the business model. It was also a platform for him with some of his other businesses, like Musictoday, to have a case study for his fan-club ticketing. It deviated into some of the other business lines that he was in.

What was an early lesson that you learned?

You have to be open to change. You could write a business plan, and it could be well thought out and planned, but the nature of our business is the twists and turns, and you have to go in expecting that and you have to be flexible in your thinking— and also be decisive and have a point of view. We were fortunate, but one of the challenges at the beginning of Bonnaroo was that everyone wanted to play. It was hard saying no. There’s the realization that if this is something that’s true to what we want to present, then you’re going to have to say no. You’re not going to please everyone, but that’s being true to what it is you’re trying to present and [having] your own point of view.

What are your worst or most stressful days like?

The harder days, which are inevitable, are the days that things get stuck, or make one step forward and two steps back, because of circumstance. It’s important, as I get older, to realize that they’ve all blended together. You have to stay diligent about things, stay on them and be aggressively patient. You have to push forward, but you’ve got to be patient. That’s why I have to have multiple things going—they all have a different trajectory, but that helps when I wrestle with that patience of not seeing things move as quickly as I would like to.

And that’s the aggressively patient concept— being aggressive about stuff but knowing when to hang tight.

That’s right. That took some time and I’m still challenged by it. There are things that are beyond your control, and there are things that are going to have their timeline because you’re working with different partners, colleagues, talent. Knowing where I can push [and] when to let go are the kind of gray in-betweens that come from learning through experience.

There’s a challenge in going from having an idea and communicating it to getting people to come on board, forming partnerships, creating a business model, bringing it into the world and having it be well received. There are so many different elements. Again, I go back to why I do it, and it can be very challenging. Sometimes I feel like the more I do it, the less I know. The biggest challenge is just being open to changes in plans or expectations, and being able to pivot a strategy. You’ve got to be passionate, focused and have a vision, but you’ve got to be open to it evolving.

Did you have a specific experience where something didn’t go the way you’d hoped and led you guys to make a big change?

There’s a ton that I’ve learned along the way, and I’m still learning to be able to just let go. If you want to build a team, have good partners and want everyone to feel invested, then there has to be some elements of compromise. There has to be an understanding of when to let go, when not to micromanage, in order to get the best out of your team or partners. That’s an easy thing to fall on, especially in your early years when your chain of command isn’t totally fleshed out—you’re making it up as you are going along. But as you do it more, you create lanes for people to take ownership. That’s how you get the best out of teams or partnerships.