In 1964, 17-year-old David Bowie released a debut single that was not a commercial success; 33 years later he sold bonds on a decade of his royalties for $55 million up front ...Saudi Arabia

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In June 1964, a 17-year-old musician named David Jones released his first single, hoping to make a name for himself in Britain’s thriving rock scene. The song, “Liza Jane,” failed to make an impression on the charts, and few listeners could have imagined that the teenager behind it would eventually become one of music’s most influential artists.

Thirty-three years later, that same musician, better known as David Bowie, would make financial history by securing $55 million through an innovative deal involving the future royalties from his music.

The contrast was extraordinary, particularly for an artist whose earliest recording had struggled to find an audience. Bowie’s debut single was released on June 5, 1964, under the name Davie Jones with the King Bees. The blues-influenced track was issued by Vocalion Records, but it failed to chart, and the group soon disbanded.

At the time, Bowie was still searching for his musical identity.

Over the next several years, he performed with various bands and experimented with different sounds before adopting the stage name David Bowie in 1966, partly to avoid confusion with Davy Jones of The Monkees.

His breakthrough finally arrived in 1969 with “Space Oddity,” a song that introduced listeners to the fictional astronaut Major Tom and established Bowie as a rising star.

“When I originally wrote about Major Tom, I thought I knew all about the great American dream and where it started and where it should stop,” Bowie later recalled. “Here was the great blast of American technological know-how shoving this guy up into space, but once he gets there he’s not quite sure why he’s there. And that’s where I left him.”

Throughout the 1970s, he transformed popular music with albums including The Rise and Fall of Ziggy Stardust and the Spiders from Mars, Aladdin Sane, and Heroes. His constant reinvention, theatrical performances, and genre-defying songwriting made him one of rock’s most distinctive figures.

By the 1990s, Bowie had amassed an extraordinary catalog of recordings. Rather than simply collecting royalties as they arrived, however, he found a way to turn those future earnings into immediate capital.

In 1997, Bowie partnered with investment banker David Pullman to create what became known as Bowie Bonds. The arrangement allowed investors to purchase bonds backed by royalties from 25 of Bowie’s albums, covering recordings made before 1990. In exchange, Bowie received $55 million up front, while investors collected the royalty income generated by the music over the following decade.

The bonds carried an interest rate of 7.9% and were purchased by Prudential Insurance Company of America. Importantly, Bowie did not permanently sell his music catalog. The arrangement was structured so that the rights would return to him after the bonds matured.

“Bowie was savvy from the beginning — his first recording deal recaptured his masters,” Pullman told Billboard. “When he signed his recording deal, he took less up front and negotiated to get his masters back. What young artist was doing that back then? He was betting that his albums were assets that would be worth more later.”

The deal attracted widespread attention in the financial world and inspired other musicians and entertainers to explore similar arrangements involving intellectual property. For Bowie, it represented another example of the creative thinking that had defined his career.

More than three decades after his first single failed to chart, the musician who once struggled to sell records had turned his existing catalog into a $55 million financial innovation, proving that his influence extended far beyond the recording studio.

Related: Andrew Mellon gave Washington a $15 million art museum in 1937, on the condition it would never bear his name

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