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

Some of us are destined to live a successful life because of the circumstances of our birth. Some of us, like Attorney Bruce Jackson, are destined to live this life, nonetheless. Growing up in New York’s Amsterdam housing project, growing up as a black man in America, and being brutalized on a daily basis, Jackson’s story is ultimately a modest success story. Of course, he went on to study at Georgetown Law School and served as vice president of law at Microsoft before representing some of the biggest names in hip-hop—LL Cool J, Heavy D, The Lost Boyz and Mr. Cheeks, SWV, Busta Rhymes. Consultant for 15 years. But at the end of the day, he’s still a black man living in America with all the baggage that comes with it.

In his autobiography, not far from home (now from atrium), Jackson recounted the challenges he faced in life, which included many: From being falsely accused of robbery at age 10, to witnessing a friend’s murder at age 15, to driving his own car as an adult; working in the entertainment industry for years Afterwards, the shock of navigating among Microsoft’s white workforce, and the end of a loving marriage that his demanding job brought about. While Jackson’s story is ultimately one of triumph, not far from home reveals the emptiness and betrayal of the American Dream in a way no one of Bill Gates’ (and this writer’s) color will likely ever experience. In the excerpt below, Jackson recalls his decision to leave the music industry ravaged by Napster for Seattle and the bleak embrace of the Pacific Northwest.

excerpt from Not Far From Home: My Journey from Brooklyn to Hip-Hop, Microsoft and the Law Bruce Jackson. Published by Atria Books, a Simon & Schuster division. Copyright © 2023 Bruce Jackson. all rights reserved.

“We have to find a way to stop this.”

In the late 1990s, the digital revolution pushed the music industry into a state of constant change. Tony Dofat is sitting in my office, having a stroke, talking about how to stop Napster and other platforms from taking off from the traditional music industry.

I shook my head. “If they’ve already done that, it’s too late. The cat is out of the bag. I don’t care if you start suing people, you’re never going back to the old patterns. It’s over.”

Indeed, the lawsuits spearheaded by Metallica and others, the defensive model chosen in the early days of the digital music onslaught, only encouraged consumers and publicized their cause. Free music for all! Won the day.

These are scary times for artists and industry executives alike. Decades of business models have been built on the premise that recorded music is a marketable commodity.

Artists would put out a record and then go on tour in support of that record. A large portion of a musician’s income (and that of record labels that support artists) comes from the sale of physical products: recorded albums (or singles), whether on vinyl, cassette or compact disc. Suddenly, that model was turned upside down…and still is. Artists earn relatively little from downloads or streaming, with most of their income coming from touring, or from monetization of social media accounts whose numbers grow with the popularity of their songs. (Spotify has publicly stated that it pays artists between $0.003 and $0.005 per stream. Translation: 250 streams will bring the recording artist about $1.)

As a result, music itself has primarily become a marketing tool, used to entice listeners to buy products: concert and festival tickets, and a social media advertising platform. It’s a tighter, leaner business model. Plus, this model changed the notion that labels and producers only needed one decent track to make an entire album. This happened all the time in the vinyl era: an artist came up with a hit single, and an album was quickly assembled, with filler often not up to the standard the single set. Streaming platforms have changed all that. Consumers today are only looking for single songs they love, and for a fraction of what they used to spend on albums. For $10 a month, you can listen to thousands of songs on Spotify, Pandora or Apple Music, about the same as an album cost before the streaming age. For consumers, it was a landmark victory (aside from the part about artists not being able to make art unless they supported themselves); for artists and labels, it was a disastrous blow.

For everyone involved with the music industry, this was a shock to the system. For me, it was provocative to think about what I wanted to do in the next phase of my career. In early 2000, I got a call from a corporate recruiter about a position at 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 required working with content providers and negotiating deals in which they agreed to make their content — music, movies, TV shows, books — available to consumers through Microsoft’s Windows Media Player. In a sense, I would still be in the entertainment industry; I would spend a lot of time working with record industry executives I had relationships with before.

But there are also disadvantages. On the one hand, I’m recently married, have a one-year-old baby and a stepson, and live in a nice place in the suburbs of New York City. When I moved to Microsoft headquarters in the Pacific Northwest, I was in no rush to leave them—or my other daughters—three thousand miles behind. From an experience standpoint, though, the offer was simply too good to turn down.

At a crossroads in my career and deeply conflicted, I sought advice from friends and colleagues, most notably Clarence Avant. If I had to name one person as the most important mentor in my life, it would have to be Clarence, “The Black Godfather”. During a remarkable life spanning nearly 90 years, Clarence has been one of the most influential figures in black culture, music, politics and civil rights. Not surprisingly, the Netflix documentary about Clarence features not only who’s who of music and entertainment biggest names, but also former U.S. presidents Barack Obama and Bill Clinton.

In the early 1990s, Clarence became chairman of the board of Motown Records. Although a noble title, it represented only a small fraction of the intelligence and power he wielded. When Microsoft made an offer, I consulted Clarence. I wonder if it would be a mistake to leave the music business and leave the company I started? Clarence walked me through the pros and cons, but in the end, he provided a steely assessment in a way only Clarence can.

“Boy, go to Microsoft and buy some stock.”