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The man behind “The Man Who Sold the World” was the first recording artist to go to Wall Street to tap the future earnings of his music, paving the way for a thriving market for esoteric securities backed by everything from racehorse stud rights to commercial washing machines.

David Bowie, who died from cancer at age 69 on Sunday, sold $55 million of bonds in 1997 that were tied to future royalties from hits including “Ziggy Stardust,” “Space Oddity” and “Changes.” Following his example were singers James Brown and Rod Stewart and the heavy-metal band Iron Maiden. Securities backed by royalties allow artists to raise money without selling the rights to their work or waiting years for payments to trickle in.

“Bowie’s bonds were as groundbreaking as his music,” said Rob Ford, a London-based money manager at TwentyFour Asset Management, which oversees 5.3 billion pounds ($7.7 billion). “Not only were they followed by a number of other artists, but they set the template for deals backed by a whole range of assets.”

The so-called Bowie bonds were sold privately to Prudential Insurance Co. of America. The securities were initially rated A3 rating by Moody’s Investors Service, the seventh-highest investment-grade rank. In the 2000s, Internet piracy led to a drop in sales and Moody’s cut the rating in 2004 to Baa3, one level above junk. The decline in worldwide recorded-music revenues slowed in 2014 as more people subscribed to streaming online services.

The Bowie bonds were paid off after 10 years and the ratings withdrawn, said Moody’s spokesman Thomas Lemmon. The New York-based company has also rated a music royalty transaction from the songwriting duo Ashford and Simpson, as well as a bond secured by a portfolio of Miramax films, including“Good Will Hunting” and “Bridget Jones’ Diary,” Lemmon said.

John Chartier, a spokesman for Prudential in Newark, New Jersey, declined to comment on the performance of the notes.

“David was extremely savvy and got things instantly,” David Pullman, the Los Angeles banker who arranged the Bowie bonds securitization, said in a phone interview Monday. “He heard what we were discussing and said why are we not doing this already?”

Underwriters in the U.S. led by Guggenheim Partners have helped expand the market for unusual securitization financing, which can provide issuers a lower cost of funds and achieve higher credit ratings than issuance of comparable company debt.

The market for securitizing intellectual property, which Bowie started, now includes film rights, pharmaceutical patents, restaurant franchises and the “Peanuts” comic strip.

It hasn’t always gone smoothly. Brown, “The Godfather of Soul” whose life and career was featured in the 2014 film “Get On Up,” sued to get out of his securitization arrangement in 2006, a year before his death.

Sales of esoteric securitizations made up 21 percent of all U.S. asset-backed issuance last year, and the sector grew faster than more traditional issuance, according to Barclays Plc data. Esoteric deal volume in the U.S. rose 16 percent to about $40 billion through November from a year earlier, Barclays analysts said in a November year-ahead outlook, forecasting at least $45 billion in sales in 2016.

While sales of esoteric deals have increased, they remain a small part of the wider asset-backed securities market. And bonds like Bowie’s remain limited by the number of artists able to reach the London-born singer-songwriter’s degree of success.

Bowie “changed the way people think about art and commerce,” Pullman said.

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