In the summer of 2014, Cyrus Borki was doing what he’s been doing for the better part of two decades: playing drums with New Found Glory during long, brutally hot summers, traveling from city to city. But at some point between soundcheck and showtime for that year’s Warped Tour, he found himself having a different kind of conversation.
The ska-punk band Less Than Jake was also on tour that year, and Borki had learned that the band’s frontman, Chris Demakes, was a licensed real estate agent in Florida. Borki pulled DeMakes aside and asked him what it was like to have a second job selling homes.
What started as a casual behind-the-scenes interaction quickly turned into a substantial career pivot. DeMakes explained to him the basics, including how licensing works, what the business is like and why it makes sense for someone whose day job relies on touring schedules and unpredictable income. The idea caught on, and Borki quickly obtained a license.
“What’s the downside? It’s just the fees and the learning curve. If I don’t really like it, I won’t do it,” Borki told Inman, noting that his wife, Debbie, a longtime Florida agent and now his business partner, had also encouraged him to go in that direction.
traveled skills
More musicians are getting into real estate than you might expect.
In the pop-punk and emo touring world of the early 2000s, many former and current musicians quietly forged second careers in real estate — some still touring actively, others long after they left the music business altogether.
Peter “PJ” DeCicco, who used to play guitar in the band Armor for Sleep, now leads a team at Compass in Essex County, New Jersey, with average sales of more than $1 million. Darren Wilson, drummer for The Hush Sound, is in the real estate business in the Nashville area.
For many touring musicians, this change isn’t as surprising as it might seem. Even with relatively high levels of success, a life on the road rarely leads to financial security. DeCicco recalls one tour where the band was tens of thousands of dollars in the red on final accounts.
“My ego was gone at that point. I just wanted to do something that could feed myself. That DIY ethic, I’m going to do it myself, I don’t need a big label. That energy translated.”
— PJ DeCicco, Armor for Sleep · Compass, Essex County, New Jersey
When Armor for Sleep ended in 2009, he found himself in his mid-twenties, with no degree, no clear path forward, and briefly delivering newspapers at 4 a.m., wondering what would happen next. Real estate offered what he felt could be a natural next life and career step, with low barriers to entry, no income caps, and no bosses to micromanage.
peter dichko
“My ego was gone at that point. I just wanted to do something that could support myself,” DeCicco said. But it wasn’t just the practical appeal that resonated. “You can fail or you can succeed. It’s all up to you. That DIY ethic, do it yourself, you don’t need a big label, that energy translated.”
Wilson’s path was less direct, but ultimately led him to a similar place. After Hush Sound stalled and his college career in Chicago gave way to other ambitions, he eventually moved to Nashville, started a family, and got his license in late 2021, just as the city’s market was booming.
Wilson tried several different agencies before arriving at Real, before finally finding the right person and the guidance that came with it.
“The biggest struggle for everyone in this industry is staying consistent,” he said. “I don’t think that kind of freedom is necessarily what some people are looking for when they get into real estate.”
No ceiling or safety net
That fascination is natural for a musician who has spent years creating something from nothing. The real estate industry offers a career with unlimited income and the autonomy of a familiar job. Every client is different, every deal is new, and the brand you build is completely yours.
“I realized that I had to start asking people questions about them, which led directly to working with clients to really understand them and understand why they do what they do.”
— Darren Wilson, The Hush Sound Real, Nashville
However, transferable skills go deeper than hustle and bustle. Wilson directly traces the relationship between Hush Sound’s post-show merchandise table and his work with clients today. After every set, he spent time talking to his fans (some excited, others unsure of how to start a conversation) and learned how to guide those interactions.
Darren Wilson
“I realized I had to start asking people questions about them,” he said. “That translates directly into working directly with clients, really understanding them and understanding why they do what they do.”
DeCicco points to something similar rooted in the DIY ethos of the scene from which many of these musicians emerged.
“We met all different types of people and had different interactions: fans, promoters, people at truck stops,” he said. “On tour, you go to these venues and all of a sudden you’re very sociable. I mean, you’re turned on. I think there’s a similar feeling with open houses and booking listings. There’s a performative aspect to it.”
While DeCicco and Wilson moved primarily into real estate, Bolooki never left music. New Found Glory continues to tour and release new albums, and Borki is juggling his music and real estate careers at the same time.
For him, real estate started out as a strategic addition rather than a necessity. He is based in Boca Raton and works with his wife Debbie at Berkshire Hathaway HomeServices Florida Realty. Debbie focuses on the vision side of things: staging, marketing, and identifying real estate potential, while Borki handles the final analysis of contracts and transactions. Some of his biggest deals were completed while on the road, he said.
“Some people come to you knowing who you are, but you still have to show them that you take this seriously. I’m not going to be a brand new agent when or if the band breaks up. I’ve been doing it forever.”
— Cyrus Borki, New Found Glory · Berkshire Hathaway HomeServices Florida Realty
Cyrus Bolki
One piece of advice DeMakes gave him early on stuck with him. The idea was that as a public figure, releasing contact information meant fielding calls from people who were fans rather than clients. He explained that if you are patient and work through them, real customers will follow.
Some of Borki’s most important deals, he said, came from longtime New Found Glory fans who specifically sought him out.
“Some people come to you knowing who you are, but you still have to show them that you take this seriously. I’m not going to be a brand new agent when or if the band breaks up. I’ve been doing it forever.”
In all three, the draw is control. There are no financial caps or safety nets. Income is often uneven when you’re just starting out, building a customer base takes time, and work often requires more availability than people initially expect.
“If you don’t take initiative, you won’t be in business,” Wilson says.
For musicians accustomed to uncertainty, those situations feel less like a drawback and more like familiar territory.
Their native scene is in the midst of a well-documented revival, with reunions, festival headlines, and audience numbers unthinkable a decade ago. Midway through the conversation, Wilson brought up Spotify stats. In the past seven days, Hush Sound had recorded 77,000 listeners. 36% of them are under the age of 24 and were born around the time the band’s first record was released.
People who used to buy tickets are now buying homes. It turns out that for a growing number of musicians, the two worlds weren’t so far apart.
Email AJ Latrace
