POWER MOVE: Oversaw one of the top 10 highest-grossing tours of all time, Madonna’s MDNA tour; has used A&R instincts to build an investment portfolio of new-tech firms and startups.
THE RUNDOWN: Oseary hasn’t actually been a music executive since exiting his role at Maverick in the early 2000s. But in addition to overseeing Madonna’s hugely successful MDNA tour (one of the top 10 highest-grossing tours ever with $305 million from 85 shows, according to Billboard Boxscore), Oseary has been playing an A&R role of sorts to startup companies both individually and with his fund A-Grade Investments alongside partners Ashton Kutcher and Ron Burkle.
During the past three years, Oseary has had a hand in the growth of companies including Groupon, Airbnb, Vita Coco, Pop Chips and Uber, with music companies like Spotify, INDMusic and SoundCloud also on his roster. In all of his moves, he says the decision to invest in a company is no different from the way he spotted talent at a record label.
“Since doing A&R at 17 and 18 years old, I can feel something in my blood, a gut instinct,” he says. “My gut has gotten me into more good things than bad things.”
Though Madonna only occasionally gets involved with Oseary’s investments (A-Grade investments Shazam, Vyclone and Fab all promoted MDNA’s album launch and tour), Oseary credits her for his desire to constantly push the limits. “She never gave me any limitations,” he says. “Others box people into categories, Madonna does not. She only sees endless possibilities.”
Guy Oseary photo by Bryce Duffy