How I Got Here: Why this startup lawyer picked a career representing tech companies

In Pittsburgh, Frost Brown Todd Senior Associate Derrick Maultsby, a 29-year-old Pittsburgh native based in the South Side, acts as a business advisor to startups and Fortune 500 companies alike.

Maultsby works in the firm’s Data Digital Assets and Technology Practice Group, Corporate Law Practice Group and Intellectual Property Practice Group. Looking back, he said, he chose to practice this brand of law because innovators and founders spend their time problem solving. As someone with immense respect for people doing things in unconventional ways, Maultsby liked the idea of assisting those brave enough to roll the dice by starting their own companies.

In his free time, the 2023 RealLIST Connectors honoree and Pittsburgh advisory board member for Venture for America unwinds by playing basketball, hiking, traveling, and enjoying theater and film.

But by day, he provides guidance and insight to the companies he represents. Here’s a look at how Maultsby navigates the world of corporate law and what keeps him in the field. This Q&A has been edited for length and clarity.

How would you describe your job to a kindergartener?

I solve people’s problems so that they can run their companies legally.

What are your tasks and responsibilities in your current position?

My day-to-day really is just working as a go-to individual for my clients, who are predominantly in the technology sector. Acting a lot as outside general counsel and serving to provide insight, guidance [and] advisement on their day-to-day business operations, transactions, … fundraising, intellectual property protection, etc. And ensuring that I provide efficient and effective legal counseling.

What excites you the most about your current role?

What excites me the most about my current role, honestly, are the founders and the investors that I get to work with daily. I love the relationships that I have that I get to build with these folks.

More than anything, on a day-to-day basis, that’s what I’m excited about — getting to work with really cool people.

How would you describe the work environment and culture at the place you work at?

Law firms are collaborative environments. It takes multiple lawyers, I think, to be successful in getting clients where they need to be. A company needs so many different things, from employment law to intellectual property law, to potentially immigration law, to maybe real estate — and so I love the collaboration and getting to work with my colleagues to help my clients.

And it’s a competitive environment. We’re judged by numbers and then output. But the nature and business of a law firm is going to always be competitive and collaborative.

Who are some of the people in your field you look up to?

[Lightship cofounder and CEO] Candice Matthews Brackeen, who is a great friend, mentor, and supporter of mine and is such an inspiring figure, and somebody that I look up to, and I’m so glad to have a professional and personal relationship with.

Also, Representative John Lewis, who’s no longer with us — his quote, you know, “good trouble,” I have it tattooed on my arm here. It really inspired me to always do what I believe is right, even if it’s not the popular thing to do.

But I think in corporate America, there’s a lot of room for good trouble. And you can’t be afraid to get into a little bit of it.

What are some of the biggest challenges you feel you’ve encountered in your career so far?

I think when you are … young and Black, and having big ideas and ambitions and conviction in what you believe in, is very difficult, because I think that the legal industry, the tech ecosystem, and the greater corporate America structure want you to follow a certain thing. “There’s a way that you do this, there are rules to this game.” And when you buck against those rules and you try to create your own path and your own lane and try to do things in a way that is authentic to you, oftentimes, people don’t necessarily care for that — and will actively, at the worst, sometimes even passively, try to derail you, and try to throw roadblocks and barriers in your way.

And that’s difficult. Being a minority in the tech ecosystem is also difficult. It’s not necessarily a place where there are a lot of Black faces. Some people are just going to try to stop that progress or to stop you from succeeding. And so those have been the biggest hurdles so far.

But I’ve been super fortunate to have great support and great mentors, great endorsers, great sponsors, who have shepherded my journey, or supported my journey along the way, and have made it possible for me to be where I am today, and will make it possible for me to be where I am 10 years from now.

What’s something you’ve done in your career so far that you’re particularly proud of?

I think the thing that I’m most proud of is that I have clients that are truly people that I care about and that, beyond dollars and cents, I value as people. And so to be in a position in my career, where I’ve built relationships with my clients, and with community partners, that are true friendships is very important to me.

And it’s something I’m really proud of because I think, at the end of the day [when] you strip away our titles and you strip away our jobs and you strip away our companies and all those things, the fact that we are able to build relationships with people on a human level and you care about each other on a personal level, I just think it’s so important. And I’m just really proud to be able to have those relationships.