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Guy Oseary: The First Yes: Four Decades of Betting on the Right People, from the Music Business to the Frontier of Technology
Paperback
Business BiographiesMusiciansPop/Rock
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Publisher: Independently Published
Published: Jul 12 2026
Pages: 234
Weight: 0.70
Height: 0.49 Width: 6.00 Depth: 9.00
Language: English
On September 9, 2014, half a billion people woke up to find a U2 album on their phones that no one had asked for. The backlash was instant and global, and the man who told the outraged world to simply delete it was not Bono. He was a soft-spoken manager most people had never heard of, a former intern who had talked his way into the music business as a teenager and never left the side of the most famous people alive.
His name is Guy Oseary, and his story is one of the strangest success stories in modern business.
An immigrant kid who faked an address to get into the right high school, Oseary became Madonna's manager and stayed at her side for more than thirty years. Then he did something almost no one in entertainment has ever pulled off. He became one of the earliest backers of Uber, Airbnb, and Spotify, built a billion-dollar venture firm, and placed some of the biggest early bets on the companies building artificial intelligence.
How does one man go from signing rock bands to funding the machines that may remake the world? THE FIRST YES argues there was never more than one skill at work. Oseary does not bet on companies or songs. He bets on people, spotted early and held for decades, and he has been running the same play his entire life.
From the collapse of a record label to a securities lawsuit that put him in the crosshairs, from a thirty-year partnership with Madonna to a fortune built on backing founders before the world knew their names, this is the propulsive, clear-eyed story of the quietest power broker in the room, and the single instinct that made him indispensable in every arena he entered.
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