Microsoft’s Bruce Jackson on Removing Barriers, Achieving Potential

Bruce Jackson
2024 Feature Nominations

In the weeks leading up to the release of his memoir, “Never Far from Home: My Journey from Brooklyn to Hip Hop, Microsoft, and the Law,” Bruce Jackson sat down with us to discuss his life and career. Jackson is the current associate general counsel for Microsoft and a former entertainment attorney, who represented hip hop royalty including LL Cool J, Heavy D, Busta Rhymes, M.C. Lyte, Jazzy Jeff and Little Kim.

“You have to be vulnerable to write something like this,” Jackson says. He looks at the memdoir as his chance to “reveal everything” to inspire people who are struggling to break through despite their circumstances.

His Career

Jackson was the first in his family to attend college. He says his aunt encouraged him not to do it for himself but for the generations before him – like his grandmother picking cotton – who couldn’t, and the generations that would follow him.

“She told me, ‘If you go to college, I’ll do all I can to take care of you.’ She was on public assistance and offered to share her food stamps and the little money she was receiving so I could survive,” Jackson says. “She told me I was changing the lives for the Jackson family going forward.”

Like many of the lawyers we’ve spoken with over the years, Jackson was first called to the law by Perry Mason. “I’m not sure how realistic it was for a kid in the inner city to become a lawyer. Reflecting back on it now, it was not very realistic considering my circumstances and resources. The goal of me being a lawyer was to inspire others – in my family and outside my family – who are in similar situations. I don’t really look at myself as a real accomplishment. I look at what others are doing to really break through barriers and that gives me great satisfaction now.”

Once out of law school, Jackson started out practicing accounting and tax law. “I just found I had a passion for it,” he says.

His transition to entertainment lawyer began with the desire to run his own business. “My college friends and myself understood that wealth is built by owning your own business and real estate, so we decided to stop working for someone else and to start working for ourselves.”

They started an entertainment management company, and Jackson stepped in as the legal counsel.

For Jackson, this was a chance to live a life-long dream. “While growing up, in addition to playing basketball, I would sneak away to take dancing, singing and acting lessons,” he says. “When I graduated high school, I had to make a choice between pursuing an entertainment career and attending college. At that point, I chose college, not because I didn’t have a passion for the arts, I did. It goes back to what you believe you can achieve. I saw a lot of people trying to become an artist working in restaurants. I couldn’t afford that risk. I took the safe bet.”

“My passion for entertainment law was derived from my passion to be an entertainer,” he adds. “My highlight was representing a lot of African American entertainers and making sure they got a fair and equitable deal.”

And while Jackson loved the clients he worked with in the entertainment industry, he knew he had to be strategic about his career. When the digital transformation hit the music industry in 2000 with Napster, Jackson made the decision to move to a tech company.

“I always tell people, you have to look at history, look at where we’re at today, and take a look at where you think we’re going in the future,” he says. “I knew it would be advantageous to move to the tech industry.”

Enter Microsoft.

When Jackson was onboarded, Microsoft seemed ideal. He had to transition from running his own business to operating as a cog in a corporate machine. Within Microsoft, however, he was given the support to succeed, but the trust to operate without micromanagement.

Two years later, he was ready to walk away from Microsoft and Seattle.

“I was the third African American Microsoft hired in the legal department,” he says. “I was based in Seattle, which in 2000 didn’t have a huge African American population. After a while, it just wore me down, the sense of loneliness.”

He was ready to walk away, but Brad Smith, now Microsoft’s vice chair and president, intervened. He worked with Jackson to find a solution, part of which, was relocating back to New York.

“I wouldn’t be here today talking to you as a Microsoft employee if it hadn’t been for him,” he says. “He understood the diversity problem and worked with me to help improve it.”

Since that decision, Jackson has received Microsoft’s diversity award, participated in Microsoft’s law and corporate affairs’ diversity efforts, helped launch Microsoft’s Elevate American Veterans Initiative, and worked to develop its diverse recruitment pipeline all while handling billions of dollars of commerce as an associate general counsel.

On Diversity

Over the course of Jackson’s career, he has been a consistent advocate for diversity and inclusion. “It has been at the forefront of everything I’ve done,” he says.

As a private practice lawyer, he encouraged his law firms to hire more diversely and to spend more with diverse vendors. He continued that practice when he started his own business.

“There were a lot of African American entertainers in rap and R&B, but there were very few lawyers. I tried to encourage others to join the legal ranks as well to give my clients visibility to other individuals – women and minorities – who served as accountants, money managers, and business managers. I exposed them to that, so they’d have a broader choice to choose from.”

Looking at the progress the legal and tech industries have made in their diversity efforts, Jackson acknowledges there has been some progress, but not enough.

“We spend billions of dollars on white papers and training on diversity collectively,” he says. “We have some of the smartest people in the world solving some of the most difficult problems in the world, but we can’t get this diversity thing right. I think we should just hire diverse candidates. They’re out there. Let’s hire them, and stop trying to figure out why we’re not doing it.”

Looking ahead in his career, Jackson is excited to start a dialogue about diversity and inspiring the next generation of lawyers. “I still get the adrenaline flowing when I close a billion-dollar deal, but I’m happy helping people to see the obstacles some face in this world and how we can help shape that collectively. Let’s start the dialogue, let’s amplify it.”

Inspiration & Removing Barriers

When writing the memoir, Jackson saw the readers as people who grew up in neighborhoods that looked like his, but in talking with his peers at Microsoft they helped him realize that his book is so much more. They saw how his words could inspire immigrants, women, the LGBTQ community – anyone who faces obstacles and can achieve more.

“I want people to look at this book and realize they too can achieve greatness,” Jackson says. “Really this is about inspiring a group of people to reach their potential. But it’s also about inspiring people who are privileged. I hope readers who are fortunate will read it and get proximity to the struggles people face and become empathetic, and help us break through these barriers to create a system where the barriers are removed.”

He sees his story as universal. “I want people to know they’re not alone with these challenges. If I can do it, you can do it. You can move obstacles, right? You have to bet on yourself. There will always be naysayers, you just have to outwork them. Be patient with yourself and give yourself grace. Dream big and bold.”

“Never Far From Home” is now available for purchase. All royalties will be donated. “This story is derived from the community,” Jackson says, “so the community should benefit. We can’t afford to leave generations of people behind anymore. I hope we can inspire as many people as possible.”

Caitlin Keniston

Caitlin Keniston is the editor-in-chief of Attorney at Law Magazine. She joined the team in 2012. Since she has written several features on prominent lawyers, CEOs and political candidates. She has also worked closely on editorial with lawyers and contributors to the magazine. She earned her bachelor's degree, summa cum laude, from Arizona State University.

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