In this latest snippet from our profiles of industry ballers, we look at a couple of snapshots from the careers of Paradigm's dynamic duo.

In 1994, as Windish was closing out his college career booking bands such as Dinosaur Jr., Sonic Youth and Cypress Hill, Diamond created Little Big Man Booking, subleasing office space in midtown Manhattan and working, literally, out of the guitar closet of Living Colour’s Vernon Reid. Diamond and his team have repped the likes of Janelle Monáe, Lorde and the Lilith Fair; with a history of doing well with singer/songwriters, he signed on to rep Sheeran after seeing him in a small club in the U.K.

Diamond’s career has been more circuitous than Windish’s. He started as an intern at Neil Warnock and Steve Hedges’ Cricket, which repped Echo and the Bunnymen, The Teardrop Explodes, Haircut 100, The Thompson Twins and Madness. “It was kind of like an underdog competitor at the time to Ian Copeland’s FBI agency,” Diamond says. “They were the gold standard at that point in terms of finding new and developing bands.”

From there, he moved to other side of the business, booking The Ritz in New York for three years. “I was there all day and all night,” he says of the venue now called Webster Hall. “Every day and every night.” After a brief time with Bill Graham Presents, he went into the record business, first at PolyGram as a product manager and then as head of artist development at Arista. It bored him.

So Diamond returned to the live side, helping market shows for Michael Farrell and Wayne Forte’s ITG. The two split up, and both asked Diamond to join them in their new ventures, but he felt it was time to go out on his own. His bankroll was the $30,000 he had in a 401K from his label gigs, and all he could afford for an office was Vernon Reid’s aforementioned guitar closet. “I was really fucking proud of that closet,” he says.

While Diamond was getting Lilith Fair off the ground with Nettwerk and McLachlan in the mid-’90s, Tom Windish was in the process of leaving his Bug Booking operation for the Billions Corporation.

“That was like winning the lottery,” he told Music Business Worldwide in 2018. “Billions was probably my favorite agency; they were booking Pavement, Jon Spencer Blues Explosion, The Jesus Lizard. They helped me sign some bands and helped me fill in some of the cities on the map where I just didn’t have relationships with promoters.”

His time at Billions coincided with the rise of Napster and the Internet, dramatically increasing the speed with which information traveled. That opened windows of opportunity for Windish, who would learn about British bands long before they were picked up for distribution in the U.S. For many young acts, the Internet helped them build a fan base far more quickly than had previously been possible.

On day one, he had about 40 acts and quickly developed a reputation for discovering artists early, signing them when they were only drawing double-digit audiences to their shows. Low—one of the first acts he signed to Bug Booking—Hot Chip, Kid Koala, Godspeed You! Black Emperor and St. Germain were among them. Once the agency—run out of a spare bedroom in his apartment with one employee—was up and running, he signed Diplo.

Windish is fond of saying the company has three principles: Only work with artists that you love, respond to every email immediately and be nice to people. “It sounds simple and silly, but we said that a lot, and we really tried to do that,” he told Crain’s. “I think it’s pretty amazing how far those principles got us.”

Read the whole profile of Marty and Tom here.