Oseary started as an independent A&R rep in 1989, at age 17, managing hip-hop performers Hen-Gee and Evil-E, and soon became one of the first employees of Madonna's Maverick record label in 1992, where he eventually rose to partner (alongside the singer's former manager Freddy DeMann). His first major signing was Candlebox in early 1994, at the age of 21, followed by Alanis Morissette -- whose Jagged Little Pill ranks as one of the biggest-selling albums of the 1990s, with U.S. sales of more than 16 million, according to SoundScan. The name Maverick "has been part of so much of my life, and it really says it all," says Oseary. "It didn't come from some executive somewhere. It came from a manager and an artist." More than 20 years later, Oseary is still working with Madonna, whose MDNA Tour was the biggest of 2012 (at $305.1 million, according to Billboard Boxscore) and ranks among the top 10 highest-grossing of all time. And last November, he merged with Paul McGuinness' Principle Management to add U2, whose Songs of Innocence just racked up 26 million free downloads on Apple's iTunes. Oseary has already asked his new Maverick colleague Gee Roberson for input on Madonna's 13th studio album, due in 2015. "What's clear is that this group has huge reach together, and a shared vision. The idea here is for everyone to be better at what they do and for artists to have more opportunities," says Oseary.
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"Bono has always had a vision for a collective of artists who support each other, and I've always liked that idea and have been proactive about starting it. With Michael Rapino's support I began engaging with managers at Artist Nation. Ron Laffitte is one of those managers and he asked me if I still had the name Maverick, and that he'd love to work with me under that brand. It all came together organically."
WHAT MAVERICK ISN'T
"It's not a rollup. I consider it a collective under one brand, with the goal of helping the clients reach their potential."
"There are a lot of people who operate with an outdated mentality, where even though they're fully aware that a certain business is dying and in need of innovation, they're scared of new possibilities. The industry is full of people with a lot of power who don't engage well with innovation. And I wish they had a support group who could be at the other end of the phone when they're confused."
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SIGN OF THE TIMES
"No. 1 albums are selling less than 100,000 units a week. That's not just a change; that's a wake-up call. If you're a manager out there that isn't aware and getting involved in new ways to do things, you'll be left out. You have to pay attention. There are all sorts of new ways to reach an audience."
"I don't know what failure is ... it's the opportunity to get it right the next time. In tech, some of the most successful companies started out by failing. But by pivoting they end up finding their way and are now very successful."
MAKING THE TECH SCENE
Since 2010, Oseary has doubled as an influential tech investor with A-Grade Investments, a fund he started with Ashton Kutcher and billionaire Ron Burkle, and which was valued at $100 million in 2013. Today, an industry source says, that valuation has soared to $150 million. "Not dissimilar to music," says Oseary, "supporting a startup can at times be like supporting an artist. They have to have a voice and a vision so you can back them. It's your job, like in A&R at a record company, to identify the voice and to say, 'That voice speaks to people. Let's get it out there to as many people as possible.' "
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"One day I walked into Ashton's office and he said, 'I was just sent this really cool company called Airbnb.' I didn't know if they had 10 people using it or thousands -- I just fell in love with the idea immediately. We flew out with Ron Burkle to meet with the guys in San Francisco and I pretty much offered to invest every dollar I had in the company. That was the only time I was willing to put everything into an idea. They didn't take everything, but they took enough."
IF I WASN'T A MUSIC MANAGER...
"I would be fully focused on tech. It's everything I'm excited about: disruption, innovation, working with people who want to change the world. The world of startups has the same excitement as when I first started working for Maverick Records."
MYSELF, IN FIVE WORDS (OR LESS)
"Curious, focused, father, Maverick."
MEET THE MAVERICKS: Guy Oseary | Cortez Bryant | Caron Veazey | Ron Laffitte | Adam Leber | Gee Roberson | Scott Rodger | Larry Rudolph | Clarence Spalding
This article first appeared in the Oct. 25 issue of Billboard.