Above: 2005 YoungArts Winner in Voice Niia Bertino with Tom Windish of The Windish Agency and Esther Park of the National YoungArts Foundation. Photo by World Red Eye. 

Few industries have felt the disruptive impact of technology as strongly as the music business. Seemingly overnight, long established practices of creation, production and consumption were upended. From auto-tuning to iTunes, artists and promoters suddenly found themselves before once unimaginable opportunities, but also daunting challenges. Old roles were reshaped, some eliminated. And the new rules of engagement are still being written, making it even more challenging for people who aspire to make a living as musicians.

That was the context, and subject, of a conversation featuring singer, pianist and composer Niia Bertino, better known as Niia (pronounced Nye-a), and booking agent extraordinaire Tom Windish, founder and owner of The Windish Agency, at a YoungArts Salon at the National YoungArts Foundation headquarters in Miami on Thursday. The discussion, which included a lively audience Q&A, was followed by a two-song performance by Niia. The event, sponsored by Knight Foundation, was moderated by Esther Park, YoungArts’ director of campus programming.

Unlike other events in the Salon series, which have tended to offer a window into an artist’s vision and work, Thursday’s event focused on artistic and business nuts and bolts and how-to concerns. Intriguingly, the conversation zigzagged between new strategies and old values.

The importance for an artist’s career of the number of Twitter or Snapchat followers was set in a musical context (“I come from an older generation, and for me it’s about understanding your craft and really trying to be the best at what you do,” noted Niia) and historical perspective. “I don’t pay attention to any of those numbers,” said Windish. “You have to try and do all that stuff well, but the biggest thing is to make great music and play great shows. At the beginning of my career … the number was SoundScan, how many records has [this artist] sold in each market? I don’t really care. What I really care about, and what I think a musician should care about today more than ever, is to make great music and be authentic.”

At another point, Niia shrugged off a discussion of “cool” noting that “most people that are cool don’t even know it. It’s not about being cool. It’s about being good at what you do.”

2005 YoungArts Winner in Voice Niia Bertino performs with Josh Bermudez, 2014 YoungArts Winner in Music. Photo by World Red Eye.

And then, there was also some practical advice. To get to a booking agent, Windish told the budding musicians in the audience, “go through a person who has a relationship with an agent or agency. It can be a publicist, a lawyer or a manager; it doesn’t matter. That person can go a lot farther than you reaching out to me. No offense, but I haven’t really picked up almost anything that I got unsolicited.”

He also said that the three principles at his agency were “book bands you like, return every email immediately and be nice to people.” He wasn’t just talking about good manners.

“The music business is a relationship business,” he said more than once. “It’s important for musicians and aspiring music business people to realize that I spend an enormous amount of time nurturing relationships.”

Meanwhile, Niia spoke of the importance of curating a career rather than simply getting bookings.

“[Windish] books me shows that make sense for me,” she said. “Meaning: You don’t want to smell cheap beer when listening to my music. He will not put me in these rock venues. It takes the right environment for my music to be better received.”

Born in a musical family—her mother was a classical pianist, her grandmother an opera singer—for Niia, music was simply around. She started by studying piano, then she discovered her voice and began performing by the age of 13, and yet, she “really didn’t understand that there was a music industry or a whole system set up to support artists in a career path,” she said. “So I just focused on the craft and studied voice.”

In time, Niia, a 2005 YoungArts Winner in Voice, found a champion in singer, songwriter and producer Wyclef Jean, who called on her to record (on the hit single “Sweetest Girl (Dollar Bill)”) and be part of his touring group. There were performances around the world and also appearances on choice TV programs such as the “Late Show With David Letterman,” “Jimmy Kimmel Live!” and “MTV New Year’s Eve in Times Square.”

Still, making the transition to solo artist, including those first recordings and live shows that might establish your name, is a high-wire act fraught with peril. “Once I understood there was this whole world of being a professional artist and making money I tried to work with the best people to help me develop the best path for me,” said Niia. Enter Tom Windish.

The shows that an artist does early on in his her career “are partly important to developing the brand, the type of following the artist wants, the way the world perceives them,” he said. “One of the things that I tell the artists that I sign is: Slow down, figure out what the plan is for next year, year and a half, two years.”

Windish started booking concerts while in college and founded his agency in 2004, out of his apartment. He had two assistants and they represented “about 50 acts.” Less than a decade later, the company was named “Independent Booking Agency of the Year” in 2012, 2013 and 2015 by Pollstar, the leading trade publication for the concert tour industry. The agency’s remarkably diverse roster features 650 artists, including acts such as singer-songwriter Lorde, DJ Diplo, Sierra Leone’s Refugee All Stars and the experimental Norwegian jazz group Jaga Jazzist, which Windish started booking without ever seeing them play live.

“The music was amazing,” he recalled. “They came over, did a very successful tour here and were awesome, so I learned even way back then to take chances.” Last year he entered a partnership with Paradigm Talent Agency, Am Only and Coda Agency, expanding into film, books and television.

“Music is at an incredible place today,” said Windish. “The most incredible place in my entire life. Almost every day I hear amazing things that my brain had never conceived of before. The walls that were up 15 years ago in the music business are largely gone. … So seize the day; go for it; do what you love.”

Fernando González is a Miami-based arts and culture writer. He can be reached via email at [email protected]