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The official CEO.com podcast featuring unfiltered conversations with the leaders shaping our world.
Clint Betts: Jonathan, thank you so much for coming on the show. What an honor to have you. You are the founder and CEO of Terrapin Station Entertainment. Prior to that, you were with the House of Blues in New Orleans, an iconic venue. You’ve done a lot of incredible things.
Tell us, what is Terrapin Station Entertainment? How did you become founder and CEO? Give us your story.
Jonathan Shank: All right. Well, I’ll give you the Cliff Notes version, so to speak.
First of all, thank you so much for having me. Great to be here.
You mentioned House of Blues, and that was actually the first place I got an internship in New Orleans. It was right when the House of Blues in New Orleans first opened in 1994, and they had an incredible lineup of artists. At that particular moment, House of Blues was one of the hottest clubs in the country.
That year they had Dylan, Clapton, Ratdog, Aerosmith, but also Bill Monroe, the Neville Brothers, Dr. John, and Dirty Dozen Brass Band. It was just this unbelievable mix of New Orleans musicians and national touring artists.
I had the distinct honor of hanging flyers in the bathrooms. That was my first job at the club.
Not just the bathrooms, though. I also went to record stores and basically became friends with every telephone pole in the city.
It all sounds very unglamorous, but in between those things, I attended almost all of the soundchecks and got to observe the entire process: load-in, soundcheck, show execution, what was the venue’s responsibility versus the artist’s responsibility.
So I got a really amazing introduction to the live business that way.
I also ended up doing some work in the talent buyer’s office, which really sparked something in my mind about where I wanted to land in the business, which was on the live side.
During my time in New Orleans, I also interned for the record producer Kim Fowley. That mostly entailed listening to him on the phone talking—or as he would say, “hustling”—other people in the music business.
When I moved out to LA in the ’90s, it was still pre-cell phone. We had car phones and things like that, but everybody still carried business cards.
Kim sent me out to Los Angeles with a stack of his business cards, and on the back of every one he had written, “Hire this guy.”
He told me that whenever I went into a job interview, I should hand them the card so they’d turn it over and see, “Hire this guy — Kim.”
I don’t know if I ever actually used those cards, but I got out to LA and started in the agency business, representing a lot of classic rock bands like Marshall Tucker Band, Dave Mason, Robbie Krieger and John Densmore from The Doors, Dave Davies from The Kinks, Jefferson Starship, and others.
I really cut my teeth booking every type of show imaginable: fairs, festivals, clubs, theaters, amphitheaters, arenas—even Marshall Tucker at the Super Bowl in Tampa Bay.
I was also working on the original Jazz Is Dead project with Jimmy Herring, Alfonso Johnson, T Lavitz, and Billy Cobham, which was this unbelievable amalgamation of artists. They sold out all their dates in 1997.
I took all of that experience and moved into day-to-day management.
At that point, I was working with a handful of artists including War, Isaac Hayes, and LFO, but it wasn’t until I signed Particle—an instrumental electronic band out of Los Angeles—that I really got tremendous experience as a manager.
Within the first two years of managing them, they played Coachella, Bonnaroo, and 10,000 Lakes, and they were headlining 1,000-to-2,000-seat clubs around the country.
We did 170 shows in one year.
They had an incredible run. They played three of the first four Bonnaroos, which was hugely impactful because it was the dawn of that festival era.
That experience taught me a lot about artist development.
After that, I worked management jobs with Irving Azoff and Red Light. I did both day-to-day and direct management for artists ranging from Eve to Panic! at the Disco, Smashing Pumpkins, Ashley Tisdale, Aly & AJ, Coco Jones, Victoria Justice, and many others.
One of the most impactful experiences I had was working with Mickey Hart from the Grateful Dead.
All of those experiences eventually led me toward producing shows and producing content.
That really introduced me to a different business model that fascinated me: licensing intellectual property and transforming that IP into live stage productions.
It started with Fresh Beat Band, then Peppa Pig, Octonauts, Disney Junior, and now Gabby’s Dollhouse Live.
Terrapin Station Entertainment was born out of the pandemic, like so many other companies, and partnered with Sony Music.
Our role is really to be a best-in-class producer of nontraditional entertainment, with a particular focus on preschool and family entertainment.
I’ve now been producing family entertainment for about 15 years, though I still like to mix in artist-driven projects as well.
I always say Terrapin was born out of the idea of bringing together mythical, magical, and iconic characters and giving them one place to gather.
Clint Betts: How has the industry changed over time, and how has technology changed it?
I mean, that’s a huge question.
How has AI changed it? How are you thinking about all of this?
From when you started until now, is this even the same industry anymore?
Jonathan Shank: There are definitely foundational disciplines that still exist, but it’s a very different business now.
When I first moved to Los Angeles, there were literally lines around the corner for A&R jobs. That was the hottest job in the industry. Everybody wanted to discover and sign artists.
Now those jobs are virtually nonexistent because everybody is an A&R person.
Anybody with a smartphone and access to YouTube can discover artists now.
The discovery process is entirely different, and the acceleration process is entirely different too.
It’s become much more of a people’s game rather than purely a corporate game because what goes viral is what labels and corporations ultimately latch onto.
Everybody is looking to streaming platforms and DSPs to understand trends rather than relying on one executive saying, “I think this artist could become huge.”
A lot of times by the time labels get involved now, there’s already a massive fan base and infrastructure built around the artist or brand.
Information also moves dramatically faster.
And because of that, people are much better at identifying what’s authentic versus something superficial.
There’s a lot more groundedness now in terms of authenticity.
Clint Betts: I have to ask before we move on: what was Dylan like live at the House of Blues in New Orleans?
What was that experience like?
Jonathan Shank: Okay. Two nights in 1994.
We could probably do an entire podcast just about Dylan.
I grew up in a house where one room was literally dedicated to Bob Dylan. He was a huge part of my inspiration into music.
I knew songs like “Visions of Johanna” when I was 10 years old. By the time I was 18, I’d probably already seen Dylan 20 times.
When he came to House of Blues in ’94, he was going through a huge renaissance creatively.
Around 1992 he had really reinvigorated his live performance. He was much more engaged, the setlists were on fire, and he was touring constantly, so the band was incredibly tight.
Dylan has always had different eras and different interpretations of his material, which is part of why he’s one of the greatest live performers ever. Nobody wants to see the exact same thing twice.
At that time he was in phenomenal form. He was still playing guitar through the whole set because he hadn’t yet developed the carpal tunnel issues that later pushed him toward keyboards more heavily.
I remember the setlists being incredible, the energy being incredible, and huge crowds outside desperately trying to get tickets.
I went both nights, by the way.
That internship definitely came in handy.
Clint Betts: That alone made the internship worth it.
That’s incredible.
I wonder how you think about leadership now and growing the company. Give us a sense for the business side of this and how you manage the day-to-day.
Jonathan Shank: First of all, I think everything starts with working with great teams and waking up excited about who you’re going to spend your day with.
I also deeply respect this industry—its history, its people, all of it.
Honestly, I think the people behind the scenes are the real rock stars because they’re the ones empowering what happens onstage and helping create inspiration for millions, potentially billions, of people.
The ecosystems surrounding artists and productions are just as important as the performers themselves.
So I approach leadership from that standpoint.
Understand the ecosystem:
Who are the agents?
Who are the managers?
Who are the publicists?
Who are the tour managers?
Understand how all the pieces fit together because, ultimately, this is still a relatively small industry.
When you look at the biggest live experiences and entertainment productions in the world, there are actually very few people and companies driving that narrative.
Leadership also comes from wanting to improve every single day and wanting to put a little positivity into the world.
And honestly, a lot of it comes from simply wanting to keep building.
I don’t necessarily know exactly where I’m going or whether I’ll even recognize it when I get there, but I know I’m pushing toward a higher place.
Clint Betts: How is the industry thinking about AI? How are you thinking about it? What do you think this is going to do?
Jonathan Shank: AI is obviously going to impact a lot of industries, including content and entertainment.
But just like humanity has adapted to every major technological shift before, we’re going to adapt to AI too.
The key is figuring out how to use it as a tool that empowers you and makes you smarter while still allowing you to create tangible ideas that exist in the real world.
Because ultimately, if we’re all just sitting around listening to AI and taking direction from AI all day long, there’s going to be very little creativity left.
So I think we need to use it as a tool of empowerment while continuing to rely on our own creativity.
If you look at music as an example, we’ve already gone from vinyl to cassette to CD to digital streaming.
If you had told someone in the 1970s that someday they’d be listening to music on a phone instead of a record player, they would’ve thought you were insane.
We’ve already adapted through many disruptive eras:
Napster.
The Wild West of digital music.
The rise of streaming platforms.
So I don’t think we should be scared.
We need to keep inventing, keep creating, and keep thinking outside the box.
Because that’s the one thing I don’t think AI can truly do: think outside the box.
Clint Betts: Yeah, that’s a really good point.
Give me a sense for what a typical day looks like for you.
Jonathan Shank: Mornings are usually internationally focused.
That’s when I’m handling UK business and anything global we need to address.
Then I’ll usually get into the office mid-morning.
We’ll have staff meetings at the beginning of the week, and then the rest of the week becomes more activation- and engagement-driven.
We’re currently doing around 225 shows this year, so there’s a lot happening constantly.
There are a lot of in-office meetings, but also a lot of meetings outside the office because networking is absolutely key in this business.
If we have rehearsals, tech runs, or live events happening, I’m often at those too. I just spent three weeks in rehearsal for one of our tours.
I also attend conferences, do a lot of public speaking at colleges and universities, and work with music business programs.
And I host a podcast too.
Clint Betts: Promote the podcast. Let’s get people listening.
Jonathan Shank: We’re about to launch season four of The Jam.
The podcast is really an homage to my roots in the jam-band scene.
It focuses on artists and lifting up both newer artists in that world and artists whose stories maybe haven’t been told enough.
We’ve had everyone from Dispatch to Cyril Neville to The Disco Biscuits to Goose to Randy Jackson.
It’s really about listening to people’s experiences and hopefully helping elevate them a little bit.
And honestly, I think that’s part of what you’re doing too.
Clint Betts: Yeah, absolutely.
Finally, because I want to respect your time, we end every interview with the same question.
At CEO.com, we believe the chances one gives are just as important as the chances one takes.
When you hear that, who gave you a chance that helped get you where you are today?
Jonathan Shank: There are honestly several people who helped get me where I am today, and I hope I can give a little of that back to others moving forward.
Sonny at House of Blues was one of the first people to really give me a shot and mentor me a bit.
Kim Fowley, who I mentioned earlier.
Michael Gaiman.
Ron Rainey.
Peter Shields—rest in peace.
And Steve Jensen, who still manages Katy Perry today. He was an incredible inspiration and one of the first managers I knew who truly understood the live business.
Those were the core people I learned from and who lifted me up.
And fortunately, I’ve had the opportunity to sit down with most of them, look them in the eye, and thank them personally.
That’s a really important and powerful thing to do once you realize how much someone impacted your life.
Clint Betts: That’s incredible.
Jonathan, thank you so much for joining us and being part of this. Congratulations on everything you’ve built. What an incredible career.
Keep going, man. So awesome.
Jonathan Shank: Thank you. Such a pleasure to be here. Truly an honor. I look forward to seeing you down the road.