It’s hard to imagine a more surprising path to becoming a top corporate lawyer than the one taken by Bruce Jackson. Raised in a Manhattan housing project by a single mother, he attended a failing high school and struggled to catch up at Hofstra, as the first in his family to attend college. Beginning at age 10, he was periodically hauled into a police station on false or trumped-up charges, and more than once spent time in jail for “driving while Black.”
In “Never Far From Home,” his memoir published by Simon & Schuster in February, Jackson, who moved to Montclair in 2019, credits his success to the support of his mother, aunt and grandmother, who motivated him to never give up, for the good of the family.
At Microsoft, Jackson, 60, is Associate General Counsel and Managing Director of Strategic Partnership out of the office of the President, managing a team of 20 attorneys responsible for $20 billion in global sales, marketing and operation contracts. In the book’s forward, his mentor Brad Smith, president of Microsoft and vice chair of the board, flips the narrative to credit Jackson with giving him advice “not only on legal and business issues, but on what we needed to do to build a more supportive environment for a more diverse workforce.”
Here, we talk with Jackson about his remarkable journey and how he managed to elude the many pitfalls and roadblocks in his path to success.
How important was your Brooklyn childhood in making you who you are?
Your community makes you. I grew up in in Crown Heights, Brooklyn until fourth grade. My grandma, aunt and uncle all lived within three blocks of me. We were a close-knit family and it was a happy childhood. Everyone in the neighborhood was poor, so we didn’t expect anything different. We didn’t have technology, so we were always outside playing street games like hot peas and butter. It was all about human interaction and socialization. We were happy poor kids.
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You were raised by your mother, aunt and grandmother. How did these women figure in your success?
My mother, grandmother and aunt formed the core of who I am today. They had all picked cotton, and it was their past struggles that motivated me. When I was a freshman at Hofstra in the NOAH program (a program beginning pre-college that offers social, financial and academic support for those from lower socioeconomic backgrounds), I called my mother and told her I was going to quit. It was too hard. My high school hadn’t prepared me; I didn’t have much math beyond basic algebra. My Aunt Viola, who’d told me about it, called me back. She told me I didn’t have a choice. No one in my family had gone to college. She said that it wasn’t just for me, it was for my mother, grandmother and the generations of Jacksons to come. Then she hung up. If it was just for myself, I would have given up. But I couldn’t look her in the face if I left.
You enrolled in the co-op work program in high school. How did this help you in your journey?
During high school, I worked part-time through the co-op program (in the New York City public schools), which was for kids who weren’t going to college. My high school wasn’t very good to begin with; then, I was basically going part-time. The other option was to rob or sell drugs. When you live in the inner city and have nothing and see the material rewards, that route is tempting. But I wanted to be legitimate. I worked in the basement of Chase Bank making copies all day. It wasn’t the best place, but it set me on the right path. I learned responsibility, getting up in the morning and to work on time and fulfilling my obligations. I also learned what I didn’t want to do, which can be just as powerful as knowing what you do want to do. I knew I didn’t want to be working in the mail room for the next 40 years.
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How important was the pre-college program at Hofstra to your success?
If it weren’t for NOAH, I wouldn’t be where I am today. This summer “boot camp” got inner city kids ready for freshman year. In addition to remedial work, we were taught Black history and learned about the major contributions African Americans made to the community, which was a huge motivating factor for me. That’s where I learned about Frederick Douglass, who said, “If there is no struggle, there is no progress.” And Longfellow’s words, “The heights by great men reached and kept were not attained by sudden flight, but they were toiling upward in the night.” I learned that what I lacked in knowledge and experience could be overcome by working harder. I had wealthy roommates who would come home after partying and find me still at my desk. When they asked why I was still working, I said, “I’m catching up to you.”
In your senior year of college, you got an offer from a top accounting firm. How and why did you decide to go to law school instead?
The Arthur Andersen recruiter was an African American woman. She explained the package they were offering and asked what I thought. I told her I was considering law school. Instead of pushing her offer, or being annoyed, she actually encouraged me to go to law school and connected me to someone in admissions at Georgetown.
Arthur Andersen was the top accounting firm in the world, and I was poor. It would have been hard not to take the job and the money if she hadn’t encouraged me to pursue law school, and helped me with a connection. She didn’t know me at all, but she understood my story.
From 1992 to 2000, you headed the largest entertainment law firm in the country. What were some of the joys and challenges of this work?
We negotiated all the contracts for the top hip-hop artists including LL Cool J, Busta Rhymes, Jazzy Jeff, and Heavy D. Most of my clients didn’t have African American business managers or accountants representing them. When minority- and women-owned businesses approached me trying to get my clients to use their services, I facilitated it, pushing my clients to give opportunities to minorities and women. It went against the agency structure and people felt threatened by that. It was a risk, but I felt a responsibility to help them. I was trying to change the narrative.
Being in the entertainment sphere, you constantly had people coming after your clients saying they could give them a better deal. You had to make sure you were buttoned up at all times and performing at top level.
A lot of the clients were attracted to me because of my inner city background; they could see themselves in me. And I could identify with them. In many cases, they were a lot younger than me and I played big brother, providing guidance and support. It was dangerous — there was a war between East and West Coast rappers. Some were killed. You had to be careful where you went and who you were with, and be constantly aware. I told my clients, stay focused, you don’t want to be caught up in violence. You’re fortunate enough to be able to make something of yourself, let’s not blow the opportunity.
What prompted you to dissolve the firm and go to Microsoft?
Prior to 2000, the music industry was physical — a record company would produce a hit record, put it on an album and people would buy the album. Then Napster allowed you to buy an individual digital single. It turned the model upside down. They were not selling albums anymore; the means of distribution was digital, and people could choose which song on the album they wanted. I decided to leave and learn the technology, how to marry it with music. The plan was to come back with a competitive advantage, but the music industry never recovered.
Joining Microsoft meant leaving your family in New York to live and work in Seattle. What was that like?
It was lonely. When I started there 20 years ago, I was one of three Black attorneys out of hundreds. Seattle was very white, too. My wife and kids were back in New York. I lived across the street front the campus and kept to myself. There were a group of female attorneys, clients, who sometimes asked me to go out with them. Finally I said yes. We went to a grunge club and I was the only Black person in the club. I wasn’t going to dance — their dancing is different from what I think of as dancing — but suddenly I found myself in the midst of it, jumping up and down. Here I was, this cool kid from the ghetto, who repped top rap artists, in Seattle in a grunge club jumping up and down with a bunch of Caucasian women attorneys.
Shortly after that, I walked into Brad Smith’s office. He’s my mentor and has played a tremendous role in my career. I told him that I’m not trying to negotiate, I’m leaving, going back home. He said, “Let’s figure this out.” He found me a spot with the company in New York. If it weren’t for his intercession, I would have left the company. His support and commitment to diversity and inclusion has changed things in a big way at Microsoft, and for me.
You’ve been pulled over and arrested three times for “driving while Black.” How did you manage to stay calm during these frightening incidents?
You gotta keep calm. I knew the consequences if I didn’t.
In 2014, I was back living with my mom in the Amsterdam housing projects after a fire in my house in Mt. Vernon, New York. I’d just closed a $100 million deal with Microsoft and was headed out to get some crabs and beer with a friend to celebrate. I was in a BMW outside the projects. The cops pulled me over, said my tail light was flickering. When they ran my license thy found an unpaid ticket from when my brother borrowed the car. For that you should get a desk appearance. But they put me in handcuffs and leg irons and I spent the night in jail, until my attorney got me out. It happens all the time for people of color. Even today, whenever I pass a cop, I think, “OK, Bruce, let’s not get arrested. It’s Friday, and you don’t want to spend the weekend in jail.” It’s what you live with, it’s always a possibility.
I was 10 the first time I was arrested. I was on a subway platform and someone yelled, “That’s him!” and pointed at me. I ran. That’s when I learned the lesson that when people run from the police, it’s not necessarily a sign of guilt — they could be scared. I was so scared I jumped onto the tracks in front of a subway train, then hopped over the electrified third rail.
The police took me in and tried to coerce me into admitting I stole something. They told me I could go home if I just admitted it. I really wanted to go home and I came close to saying that I did it. If I had, my life would have been totally changed.
Why did you move to Montclair?
A friend of mine was looking to move here and I went along. I ended up buying a two-family house in Frog Hollow as an investment property. (Frog Hollow is a traditionally African-American neighborhood bordering Valley, Midland and Walnut Streets.) Eventually I bought two more properties and moved here myself with my fiance four years ago. One of my daughters lives here now, too. Montclair was an easy transition from New York City. It’s a combination of suburb and city, that’s the beauty of it. And it has the entertainment scenario — music, theater, the film festival. The vibe for me was right. I feel at home here.
You’re donating all the royalties from your books to nonprofits that service underserved communities like the one you grew up in. What groups are you involved with, and why?
The book is truly a passion project for me. By sharing my story of perseverance, I hope to inspire others to reach their full potential. I’ve always felt an obligation to be an agent for change. Mentoring young people is important, and I can’t forget women — I have three daughters, and was raised by three women who were an instrumental part of my success. I speak to a lot of school groups, and am on the board of the Embrace Girls Foundation, which promotes after-school programs to give girls a head start on success, and the advisory board for the National Association of Minority and Women-Owned Law Firms. I’m also on the board of the Hip Hop Museum in the Bronx and serve on Mayor Eric Adam’s corporate counsel committee.
Before I visit with young people, I change out of the “uniform” I wear at Microsoft, the dockers and the polo shirt. I feel their suspicion. I have to convince them that “I’m one of you. I was you.”