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Editor’s Note: This is the latest installment in a series of one-on-one interviews with leaders of corporate legal departments in the U.S. This month we spoke to Bruce Jackson, who is Associate General Counsel of Microsoft Corporation, the largest software company in the world. Mr. Jackson has spent three decades working with some of the top music producers in the U.S. and is the author of Never Far from Home, a forthcoming memoir to be published by Simon & Schuster’s Atria Books. The interview has been edited for brevity.
Q: Can you tell us a little bit about where you grew up?
A: I was born in Brooklyn, New York, and lived for the first several years in Crown Heights, a low-income and predominantly African American community at that time. We moved to Manhattan when I was in the fifth grade and lived in a public housing project. I attended public schools in New York City and was a good student, but one thing that a lot of my friends didn’t know was that I always loved the arts. I took singing and dancing lessons, joined theater groups, and really loved acting.
Q: Did you ever consider taking a shot at a career in acting?
A: Actually, I did. But you know, growing up in Manhattan, I couldn’t help but notice all of the unemployed or struggling actors working part-time jobs and having a hard time making ends meet. I decided that it was a risk I didn’t want to take and that a more conventional direction—get a good education, find a steady professional career—would be the responsible route for me to help my family. I think about that decision a lot and wonder if things might have been different if I would have bet on myself, but I’m obviously very grateful for how things have worked out in my life.
Q: Tell us about those educational years.
A: I attended Hofstra University on Long Island in New York. I was an accounting major and really excelled at anything involving a company’s finances. In fact, I interned at Arthur Andersen—one of the old “Big Eight” public accounting firms—and was offered a job right out of college by several of the major accounting firms in New York. But the more I thought about my future, I really wanted to go to law school and become an attorney. It was planted in me when I was a kid, watching the injustice in my community and watching old “Perry Mason” episodes on TV after school.
Q: You went to Georgetown Law School in Washington, D.C., an elite school that is not inexpensive. What was that experience like for you?
A: To be honest, I encountered my share of challenges as a law student, especially as an African American who grew up in public housing. But I found a lot of solace in a quote from Frederick Douglass that I replayed over and over in my mind: “If there is no struggle, there is no progress.” I was determined to embrace the struggle and put in the extra work to succeed; I knew that I wasn’t the smartest or richest kid in the class, but I was going to outwork everyone. I’ve always loved that old Longfellow verse, “The heights by great men reached and kept were not attained by sudden flight, but they while their companions slept, were toiling upward in the night.” Those two quotes are what I’ve lived by my entire life.
Q: Where did your legal career get started?
A: I had worked as a summer associate at a tax law firm in Washington, and the partners there noticed that the combination of my accounting knowledge and legal training made me an asset as a tax lawyer. They offered me a full-time job as a tax associate, but I was very hesitant to accept because of an unfortunate incident over lunch, when a senior partner at the firm made some disturbing remarks to me that were rooted in racial prejudice. We had an exchange, and he knew that I would not accept that behavior. In the end, though, I was convinced that it was a great opportunity. Besides, where else would I go? I did not believe that I could escape that behavior, and there were very few African American tax attorneys in any law firm at that time. At this firm, at least I knew who I was dealing with. So, I worked at that firm for two years and then moved on.
Q: How did you find yourself opening your own entertainment law firm while still in your 20s?
A: I was working part time for an entertainment law firm in New York that primarily represented artists, while also teaching tax law and accounting at Baruch College in New York City. It was a great mix of work that really aligned my interests with my skills and expertise. As time went on, I started representing some of the bigger names in the Hip Hop world—such as Pete Rock, MC Lyte and LL Cool J—and those artists and their managers would refer me to other artists. In 1993, I linked up with a few colleagues and we opened our own firm (Jackson, Brown, Powell and St. George) to serve clients in the entertainment industry. It was an amazing and exciting time, and it also taught me an important lesson that I’ve tried to pass on to others: You don’t accomplish anything in life on your own; everyone needs a helping hand from other people to realize their full potential.
Q: The very foundation of the music industry began to shake in the late 1990s with the rise of digital media and streaming technology. How did that shift impact your career path?
A: Our firm was staying very busy, but in 2000 I received an interesting call about a new corporate counsel position they were creating at Microsoft. The executives here were very savvy about the future of digital media and were looking for someone with the right mix of experience to help them bridge the divide between content and platform. They knew the key would be to get the right deals and partnerships in place to smooth the way for format adoption in streaming media. I felt this was a once-in-a-lifetime opportunity for me, so I accepted the job and have been here for more than 20 years now in various corporate legal positions.
Q: Tell us a little bit about your major business responsibilities over those years.
A: I’ve been responsible for negotiating and signing deals with essentially all of the major content owners in the media industry—record companies, music publishers, movie studios, book publishers, you name it. I’ve also had various corporate management duties along the way. I’m now the Associate General Counsel for the U.S. Regulated Industries Group, where I manage a team of 20 legal professionals supporting several of our major businesses that contribute roughly $15 billion in revenue to the company. We are in a unique position to help our businesses reimagine their futures by helping them navigate their digital transformation journeys in a way that is socially responsible and financially profitable.
Q: As you look back on your work during this extraordinary two decades of industry transformation, what stands out to you?
A: Well, it’s important to understand that the digital format was changing the fundamentals of the media industry so rapidly, the content owners were simply not able to move fast enough to adapt their business models to streaming media. So I’m especially proud of the work we’ve done at Microsoft to engage with these companies and artists, helping them transform the way they do business, and putting in place partnerships that enabled them to adopt a new content distribution model that realized fair revenues for everyone involved. I feel very good about that work. In general, I feel good about my work at Microsoft to empower every person and every organization on the planet to achieve more.
Q: You’ve also been very active with promoting diversity and inclusion in the profession, as well as working hard to promote Hip Hop culture.
A: I’ve served on Microsoft’s diversity committee since 2001, and I was really grateful to receive Microsoft’s Diversity Award several years ago. I’m also a board member of the National Association of Minority & Women Owned Law Firms. It is ironic that the legal profession is behind when it comes to diversity. We have lots of smart people, who have solved all sorts of major problems, working on this particular issue for years. They have spent millions of dollars on white papers, training programs and conferences—yet our diversity numbers have still not increased much. We need to stop overthinking and just get to work on hiring diverse candidates and promoting them based on potential.
I’ve never lost my passion for the arts, especially for Hip Hop music and culture. Earlier this year, I had the opportunity to participate in a $5 million gift from Microsoft to the Universal Hip Hop Museum for the creation of its AI for Cultural Heritage program. This is going to be an amazing program that will leverage the power of artificial intelligence to empower people and organizations dedicated to the preservation and enrichment of global Hip Hop culture to inspire, empower and promote understanding.
Q: As we look to the future in the corporate legal profession, do you have any key learnings to share or specific issues that in-house counsel need to be tracking?
A: Cybersecurity is a major issue. The private sector has to work closely with the government to help deal with the problem. In addition, a lesson that I learned and internalized a long time ago is that none of us can operate businesses in isolation from government regulation. In-house counsel simply must be engaged with government regulators every step of the way, working with them to ensure compliance. On that note, I think it’s inevitable that there is more regulation to come surrounding data privacy issues, especially as we see more companies undergo digital transformations. All of us should monitor proposed legislation, but prepare now for this eventuality.