"In terms of what I sign, or the things I'm involved with, I very much act on what's my gut and how does it make me feel," said Diamond during the conversation. "I still sign what I like and work on what I think is really cool and when I try to divert from that instinct, I fuck up. Anytime I'm like, 'I'm gonna sign this because it's going to be big thing,' it ain't big. Nine times out of 10."
Diamond -- who was recently honored by longtime clients Sara Bareilles, Janelle Monae and David Gray at the annual gala of New York's City Parks Foundation -- honed his instincts for years before starting Little Big Man, working jobs at Arista, PolyGram, Bill Graham Management, New York music venue The Ritz (now Webster Hall) and, finally, International Talent Group. But it was only when ITG co-founders Wayne Forte and Michael Farrell decided to part ways that Diamond finally made the decision to strike out on his own.
"I had $30,000. A friend of mine, Jim Grant and his partner Roger Cramer who at the time looked after Soul Coughing and Living Colour said, 'Oh, you can take space in our office,'" said Diamond. "And they were literally across the street from where ITG was on Seventh Avenue. So I took the boxes, walked across the street -- never really looking at the space that Jim was giving me, just assuming I'm getting an office – [and] it was Vernon Reid's guitar closet."
Despite these humble beginnings, Diamond -- along with Webman and Tammy Shin-Sprotte, who now works in accounting at Paradigm – built Little Big Man into a thriving booking agency via a mixture of passion, industry savvy and unadulterated work ethic.
"Marty has a very creative outlook on things, and with his various other experiences up to that point, he was able to sit in a meeting with a client and talk about their full career with an in-depth knowledge of the workings of record labels and merchandise and management," said Webman. "At the time, other agents who were just agents for their whole career didn't really have that full view. I think his passion for the act and being able to talk the whole picture helped convince people that, 'yeah, this guy knows what he's doing.' And plus, I just think we out-hustled everybody."
The hustle paid off. Over the next decade, Diamond and his cohorts built Little Big Man into a world-class boutique touring agency, going on to rep such superstar acts as Monae, Coldplay, Franz Ferdinand, Avril Lavigne, Arctic Monkeys, Snow Patrol and Sarah McLachlan, with whom Diamond co-founded the all-woman touring festival the Lilith Fair in the late ‘90s. And in 2006, the agency was acquired by Paradigm, where Diamond has been ever since (he was named global music head this past April).
Today, Diamond continues to thrive in a music industry that has radically altered since he first entered it decades ago. He hears these changes echoed in the words of his own children, who embody the fast pace of today's streaming culture during joint listening sessions in the car.
"I travel to Montauk during the summer quite a bit, and until my kids basically tune me out completely, I live by top hits on the streaming cycle in the car," he said. "And I spend more time skipping songs. And then asking, 'But I thought you liked that?' [And they answer] ‘No, no, I liked it last week.'"
As Diamond notes, that kind of culture can make things tricky when it comes to booking artists whose big streaming numbers don't always translate into loyal fan bases.
"There is this component of like, that 2 million streams or 3 million streams or 5 million streams might mean 17 tickets [being sold]," he continued. "You can look at the data ... but there's a very big disconnect between I'm taking $10 out of my pocket or $20 out of my pocket on a song."
As loyalty goes, there are few in the business who can command it as well as Diamond, many of whose early clients -- including Bareilles, former Verve frontman Richard Ashcroft and his very first client David Gray -- have remained with him for decades. And despite his reputation as a larger-than-life personality, Webman notes that more than anything, Diamond has succeeded by opening his ears.
"Marty's best quality is his ability to listen," Webman said. "To be able to take what that person is saying, and see the bigger picture to it."
But perhaps Diamond's most important asset is his ongoing passion for the work that he does.
"I still love this," he said near the end of the Q&A. "I still get in the car and sing when the radio's on."