(1) Terra Firma’s acquisition of EMI, $4.7 billion (2007)
Even Guy Hands admits he made a colossal mistake on this one. One of the last super-leveraged buyouts before the bust, EMI has now become a $4.7 billion-plus toxic mess for Terra Firma.
(2) CBS’ acquisition of Last.fm, $280 million (2007)
Scrobbling is cool and all – and this is still a very cool site – but few would “recommend” this deal today. Amidst predictable ad monetization challenges, the company has since switched to pay-only in certain European countries, outsourced full-length videos, and bid adieu to the original founders.
(3) Bertelsmann’s investments in Napster, $100 million (2000-onward)
In retrospect, Bertelsmann was the forward-thinking maverick. But in the moment, that stance created a legal sinkhole for the company, accused of facilitating widespread infringement by keeping the P2P alive. The in-fighting lasted years before expensive settlements torpedoed Bertelsmann with hundreds of millions in losses.
(4) MP3.com acquisition by Vivendi, $372 million (2001)
Before MySpace was even conceptualized, MP3.com was setting huge records for IPO valuations, label lawsuits, and band profiles. Problems quickly followed the inflated purchase, and the site was quickly dumped by Vivendi Universal in 2003.
(5) The Robbie Williams 360-Degree Deal, $160 million (2002)
Williams loves being able to walk the streets of Los Angeles without being recognized. EMI, which structured the pricey deal, is somehow less thrilled by that freedom.
(6) The Sony BMG Joint Venture (2004)
The 50-50 JV was like “tying two sinking rocks together,” according to one executive, and this seemed like a dead weight from the beginning. Bertelsmann walked away, and the combination was ultimately purchased by partner Sony Music Entertainment by 2008.
(7) WMG’s Investment in Imeem (2009)
“We do not intend to make more digital venture capital investments,” WMG chairman Edgar Bronfman told investors after suffering a $16 million write-off on Imeem in 2009. MySpace subsequently scooped the property for well under $1 million.
(8) WMG’s Purchase of Bulldog Entertainment, $16 million (2007)
Bulldog Entertainment Group was best known for coordinating tony concerts in the Hamptons. The company eventually cratered with estimated losses of $30 million.
(9) Any Deal Involving PlaysforSure…
This was a mistake that caused endless suffering, for music service (Yahoo Music, MTV Urge, Wal-Mart), player (Sony, SanDisk, Samsung), and consumer alike. In fact, even Microsoft bailed on its DRM-heavy solution with the launch of Zune.
(10) Best Buy’s Exclusive on Chinese Democracy…
Some comebacks are better than others, and Best Buy was left carrying a truckload of Guns N’ Roses CDs. That did little to kill the big box exclusive, however, as plenty of big-name artists have used the concept to shift serious tonnage.