Tom Windish is the head of business development and A&R for the talent agency Wasserman Music, where his clients include the artists Lorde, the xx and Coachella headliner Billie Eilish. And like the most seasoned of booking agents, he got his start while still in college. SUNY Binghamton in New York is where he first caught the bug for buzzing bands that were left of center. Upon graduating, he had a short-lived internship at William Morris, where he would bug the agents to show him the ropes. It’s why Tom named his own company Bug, launched a little over 30 years ago as the indie rock scene was exploding.

In fact, the word indie is practically baked into Tom’s last name, which makes his career track seem almost pre-destined. Circumstances led him to Chicago, where he would build a formidable roster of bands most people had never heard of, and he would scale up to include dozens more. That led to gaining the attention of the budding midwest booking agency Billions, which took Tom under its wing from 1997 to 2004.

For the following 13 years, Tom called The Windish Agency home. He operated a lean and mean machine that looked after hundreds of artists, but it was his own skills as a talent scout — and being in the right place at the right time — that resulted in identifying the singular talent that is Billie Eilish.

As she and other clients got more popular, competing agencies, he says, “were all trying to steal them.” The solution, as Tom Windish saw it, was to align with a bigger entity. He chose Paradigm in 2017 as it had absorbed several small- to mid-sized indies “cut from the same cloth” — among them the firms Little Big Man, AM Only, Coda and X-Ray Touring — which brought to the roster such touring giants as Ed Sheeran, Coldplay, David Guetta and Phish.

Not long after arriving at Paradigm, Tom Windish marveled at the health of his industry. Little did he know what was coming in the form of COVID. The pandemic not only disrupted touring in its physical form, it turned the business of live music upside down. All agencies were impacted, but Paradigm in particular lost its financial footing and began exploring a merger or a sale. The buyer would turn out to be Casey Wasserman, grandson of Lew Wasserman who was among Hollywood’s founding fathers, working for over eight decades to completely reshape entertainment.

Not surprisingly, Tom was well-read on the Wasserman dynasty and it’s proven to be an asset and he and his new boss navigate the post-COVID landscape, passing on that guidance to his artists.

As Tom Windish prepares to fly from his home base of New York to Indio, Calif. for Coachella, where he has multiple acts on the bill — among them: Rina Sawayama and the Viagra Boys — he cautiously exhales while recounting the routing and supply chain problems COVID has wrought, how Eilish’s live career progressed methodically (despite second-guessing by peers), when streaming “turned the floodlights on” lesser-known artists and what he’s learned from decades spent directing artists on the road.

Listen to his appearance on Variety‘s “Strictly Business” below or wherever you get your podcasts.