#72 Tyler Cain | What It Really Takes to Get Hired as a Stadium Touring Musician
Tyler Cain’s first real paycheck in music came from a German beer hall inside a Virginia theme park. He was a teenager at Busch Gardens Williamsburg, dressed like Pinocchio, playing the chicken dance for $12 an hour.
The guitar was only part of the job. The headliner was an 87-year-old local legend who’d sung oompah drinking songs at the park for about 30 years, and he had started falling down. Once he tumbled down the stage steps so hard the staff thought he’d died. He got back up singing.
“So they hired me. My job was to play the chicken dance with him, but then when he falls, I had to catch him and stand him back up again.”
Two decades later, Tyler has played arenas and stadiums with Big & Rich, Gavin DeGraw, Colbie Caillat, Billy Currington, and James Otto, worked in the studio with artists from Ashley Monroe to Darius Rucker, and co-founded Bold Music Group with his wife, Meghan Linsey. He also gave Nikki Sanz her first job in Nashville.
Bar Gigs at 13
At 13, Tyler joined a Virginia band called The Noodles after the singer read a local newspaper article about a young guitar player in town. The singer’s grandmother managed the band and had the kids learn Elvis and Jerry Lee Lewis songs. They went to school during the day and played four-hour bar sets at night, then went home with about $75 each.
When Nikki asks if he felt different from the other kids at school, his answer is two words: “More tired.”
The Noodles opened for artists passing through Virginia, including Brad Paisley when he had one single out. Tyler spent those nights backstage trying to get the touring musicians to tell him about that life. It’s why he makes time now for the kids who hang around after his shows.
“You have to give them time of day, because you know this could become their whole life.”
Then came Nashville and Belmont University, where he met the friends who are still his closest. The bar sets had already taught him the rest.
The FBI on the Living Room Floor
Toward the end of Belmont, an internship at a management company turned into Tyler’s first industry job. Then an independent label bought the company.
Tyler saw a pattern on Music Row back then: a wealthy investor funds a label, burns through millions, and the doors close overnight. His label added a twist. The man funding it went to prison, and the FBI came to Tyler’s apartment asking about the money.
He was 21 or 22. The apartment had no furniture and no TV, so the agents sat on the floor.
“I think they’re like, this isn’t our guy. And then they moved on.”
The label closed. The next day, Tyler got a call to go on radio tour with Ashley Monroe and Sarah Buxton. That call turned into 20 years on the road.
A Studio With No Gear
Ashley Monroe wrote for Wrensong, a publishing company run by Ree Guyer, who rented Tyler a vacant studio in the back of the building on Music Row. Tyler counts her as a mentor from watching how she ran the business. (Her father, Reyn Guyer, co-created Twister and the Nerf ball.)
He had a room and no equipment. Then Ree called him into her office. Ashley was out of her deal with Columbia. Would he produce a six-song EP?
It was the first time anyone had hired Tyler to produce. He called an engineer friend, offered him the session, and then asked for one more thing.
“Can you bring all the gear from your studio over to my studio? I was like, hear me out.”
After that, his touring money went into equipment. He’s built four studios since, and he takes artists’ budgets seriously. Someone might work six months or crowdfund to pay for a record, and Tyler doesn’t spend that money lightly.
One Hit Song and a Faux Hawk
Around 2008, Tyler was on the road with James Otto when “Just Got Started Lovin’ You” took off. It was the first time he watched an artist rise from inside the band. One week the room was nearly empty. A week or two later, the same kind of show was packed and sold out.
“The power of a hit song is like bananas.”
James gave Tyler his first arena, his first stadium, and his first time breaking three strings during a televised stadium show. That run also fed his ego. They were playing arenas with Lynyrd Skynyrd and Hank Williams Jr., and Tyler wore skinny jeans, a wallet chain, and a faux hawk he styled with hair goop every time he climbed out of his bunk.
At a Chinese restaurant in Arkansas, the owners’ 3-year-old daughter walked up, tapped his leg, and asked if the band were clowns. She was not joking.
Tyler calls that a turning point. A sideman is there to work for the artist, and he admits it took a few years of being lost in the sauce before that sank in.
Every Gig Started With a Phone Call
After James Otto came five or six years with Big & Rich, several stints with Billy Currington, and three and a half years with Gavin DeGraw. A friend he met on his first day at Belmont got him the Currington gig, and the two have been passing each other’s names around ever since.
Tyler has gotten one gig from an audition in his entire career. Every other tour came from a call from a friend.
“Every opportunity starts with somebody.”
When people back home talk about the odds of making it, Tyler runs the numbers his own way. Start with everyone talented enough. Keep the ones who show up on time, then the ones who show up prepared, then the ones who are good to be around. The pool left is small, and there’s real demand for it.
“You can’t teach people to be cool.”
He’s seen far more people lose gigs over personality than over talent.
The Right People
Tyler has one quote he gives anyone putting together a band for an artist or a crew for a tour:
“If you have the wrong people, there’s nothing you can say. And if you have the right people, there’s nothing you need to say.”
He’s watched one bad person ruin a tour for everyone. Asked how he handles that as a leader, his first answer is “very brutally.”
Even after 20 years, he gets superstitious about turning down a tour, half-convinced the calls will stop if he does. He says no anyway when something isn’t right, because that’s how you make room for what is.
Bold Music Group Started With the Rent
Tyler met Meghan Linsey while producing a James Otto project at Jay DeMarcus’s studio. Meghan was in Steel Magnolia, touring around 200 days a year, and had ruptured a vocal cord on the road. James wanted her on a duet anyway, so she kept coming back to redo it. They’ve been together 14 years.
Their experiential business started with a practical problem. Their studio sat next to House of Blues Studios in Berry Hill, and the rent was high.
“The music industry is so up and down. But the rent’s not up and down. It’s only up.”
So they started a concert series inside the studio, four shows every weekend. That was the beginning of Bold Music Group.
It’s also where Nikki came in. Tyler and Meghan met her at a CMA Fest signing, where she was one of about 10 people working for the Nashville CVC and, by Tyler’s count, the only one getting anything done. They hired her to build client lists and hand out fliers on Broadway. Tyler also once asked her to stop showing up five minutes late. Nikki says that one note changed her life.
Leaving the Creaks In
Tyler recently bought a tape machine for his studio and has been cutting sessions with no click track and the band in the room together. AI is part of the reason. He’ll spend weeks on a track, play it for someone, and the first thing they ask is whether it was made with Suno.
“Lately, I just prefer leaving the sound of the room in the recording. Leaving the creak in the chairs, things that let you know that it was humans there.”
He traces the idea to a flight where he sat next to an engineer who’d worked on Michael Jackson records. The engineer’s point: much of a sound’s emotion comes from how your ear hears the room, the first reflections off the surfaces. It’s why Tyler still tracks at FAME in Muscle Shoals, where a band can record without headphones.
His most recent release is Generations, an instrumental EP from Tyler y Zoro, his project with drummer Zoro, whose credits include Lenny Kravitz’s band. G. Love, Eddie Perez of The Mavericks, and Shannon Sanders all appear on it, with the guitar carrying the melody where a singer usually would.
“Bubbly,” Planet Fitness, and the Post-Show Comedown
Tyler’s show days start at the gym, and there’s a story behind that. He threw his back out playing “Bubbly” with Colbie Caillat on acoustic guitar.
“I was like, I’m not going down like this, throwing my back out on the gentlest song of all time.”
His tip for anyone on tour: Planet Fitness gives you a free day, so a 30-city run can mean 30 free workouts. After that he walks the city, usually with a Fujifilm X100VI for street photography, then soundcheck, email, and dinner a few hours before the show.
The harder part is after the show: going from an arena full of energy to a quiet hotel room. Tyler knows a lot of musicians who struggle with that comedown, and he’ll often take another walk at night to ease it.
“I just don’t want to be too alone with my own mind all at once.”
He also has a warning about getting used to a great crew. After years with Gavin DeGraw, where the techs handled everything, he played a show with someone else and left all his gear at the venue. Three hours later, someone asked if he was ever coming back for it.
Free to Be Early
When Nikki asks for advice for young musicians, Tyler comes back to a short list: love the craft, keep your word, show up prepared, and be careful about who’s in your circle, because those are the people who will rise with you.
“It’s free to be early. It’s free to be nice to people, not talk poorly of anyone. It’s free to have a good attitude. … Just doing those things alone are going to put you ahead of probably like 80 or 90% of people fighting for the same opportunities.”
Last year, Tyler went back to Busch Gardens to play the amphitheater with Colbie Caillat, the same stage he used to stare at from the park in his Festhaus costume. The outfit still does its job.
“Once you’ve dressed like Pinocchio, you’re humbled forever.”
