Hitting the Books: Meet the man who helped Microsoft break into the entertainment business

Some of us are destined to lead successful lives thanks to the circumstances of our birth. Some of us, like attorney Bruce Jackson, are destined to lead such lives in spite them. Raised in New York's Amsterdam housing projects and subjected to the daily brutalities of growing up a black man in America, Jackson's story is ultimately one of tempered success. Sure he went on to study at Georgetown Law before representing some of the biggest names in hip hop — LL Cool J, Heavy D, the Lost Boyz and Mr. Cheeks, SWV, Busta Rhymes — and working 15 years as Microsoft's associate general counsel. But at the end of the day, he is still a black man living in America, with all the baggage that comes with it.

In his autobiography, Never Far from Home (out now from Atria), Jackson recounts the challenges he has faced in life, of which there are no shortage: from being falsely accused of robbery at age 10 to witnessing the murder of his friend at 15 to spending a night in lockup as an adult for the crime of driving his own car; the shock of navigating Microsoft's lillywhite workforce following years spent in the entertainment industry, and the end of a loving marriage brought low by his demanding work. While Jackson's story is ultimately one of triumph, Never Far from Home reveals a hollowness, a betrayal, of the American Dream that people of Bill Gates' (and this writer's) complexion will likely never have to experience. In the excerpt below, Jackson recalls his decision to leave a Napster-ravaged music industry to the clammy embrace of Seattle and the Pacific Northwest. 

Excerpted from Never Far From Home My Journey from Brooklyn to Hip Hop, Microsoft, and the Law by Bruce Jackson. Published by Atria Books, an imprint of Simon & Schuster. Copyright © 2023 by Bruce Jackson. All rights reserved.

“We gotta figure out a way to stop this.”

In the late 1990s, the digital revolution pushed the music business into a state of flux. And here was Tony Dofat, sitting in my office, apoplectic, talking about how to stop Napster and other platforms from taking the legs out from under the traditional recording industry.

I shook my head. “If they’re already doing it, then it’s too late. Cat’s out of the bag. I don’t care if you start suing people, you’re never going back to the old model. It’s over.”

In fact, lawsuits, spearheaded by Metallica and others, the chosen mode of defense in those early days of the digital music onslaught, only served to embolden consumers and publicize their cause. Free music for everyone! won the day.

These were terrifying times for artists and industry executives alike. A decades-old business model had been built on the premise that recorded music was a salable commodity.

Artists would put out a record and then embark on a promotional tour to support that record. A significant portion of a musician’s income (and the income of the label that supported the artist) was derived from the sale of a physical product: recorded albums (or singles), either in vinyl, cassette, or compact disc. Suddenly, that model was flipped on its head... and still is. Artists earn a comparative pittance from downloads or streams, and most of their revenue is derived from touring, or from monetizing social media accounts whose numbers are bolstered by a song’s popularity. (Publicly, Spotify has stated that it pays artists between $.003 and $.005 per stream. Translation: 250 streams will result in revenue of approximately one dollar for the recording artist.)

Thus, the music itself has been turned primarily into a marketing tool used to entice listeners to the product: concert and festival tickets, and a social media advertising platform. It is a much tougher and leaner business model. Additionally, it is a model that changed the notion that record labels and producers needed only one decent track around which they could build an entire album. This happened all the time in the vinyl era: an artist came up with a hit single, an album was quickly assembled, often with filler that did not meet the standard established by the single. Streaming platforms changed all of that. Consumers today seek out only the individual songs they like, and do it for a fraction of what they used to spend on albums. Ten bucks a month gets you access to thousands of songs on Spotify or Pandora or Apple Music roughly the same amount a single album cost in the pre-streaming era. For consumers, it has been a landmark victory (except for the part about artists not being able to create art if they can’t feed themselves); for artists and record labels, it has been a catastrophic blow.

For everyone connected to the music business, it was a shock to the system. For me, it was provocation to consider what I wanted to do with the next phase of my career. In early 2000, I received a call from a corporate recruiter about a position with Microsoft, which was looking for an in-house counsel with a background in entertainment law — specifically, to work in the company’s burgeoning digital media division. The job would entail working with content providers and negotiating deals in which they would agree to make their content — music, movies, television shows, books — available to consumers via Microsoft’s Windows Media Player. In a sense, I would still be in the entertainment business; I would be spending a lot of time working with the same recording industry executives with whom I had built prior relationships.

But there were downsides, as well. For one thing, I was recently married, with a one-year-old baby and a stepson, living in a nice place in the New York City suburbs. I wasn’t eager to leave them—or my other daughters—three thousand miles behind while I moved to Microsoft’s headquarters in the Pacific Northwest. From an experience standpoint, though, it was almost too good an offer to turn down.

Deeply conflicted and at a crossroads in my career, I solicited advice from friends and colleagues, including, most notably, Clarence Avant. If I had to name one person who has been the most important mentor in my life, it would be Clarence, “the Black Godfather.” In an extraordinary life that now spans almost ninety years, Clarence has been among the most influential men in Black culture, music, politics, and civil rights. It’s no surprise that Netflix’s documentary on Clarence featured interviews with not just a who’s who of music and entertainment industry superstars, but also former US presidents Barack Obama and Bill Clinton.

In the early 1990s, Clarence became chairman of the board of Motown Records. As lofty a title as that might be, it denotes only a fraction of the wisdom and power he wielded. When the offer came down from Microsoft, I consulted with Clarence. Would I be making a mistake, I wondered, by leaving the music business and walking away from a firm I had started? Clarence talked me through the pros and cons, but in the end, he offered a steely assessment, in a way that only Clarence could.

“Son, take your ass to Microsoft, and get some of that stock.”