Tell us your story. What kind of law do you practice? How did you get to where you are today?

I’m a corporate transactional attorney (startup attorney, for lack of a better word), practicing in the areas of securities law, mergers & acquisitions, venture capital and general corporate law. I work primarily with startup companies from their initial organizations and financings to their future acquisitions or exits.

I grew up in Asheville, North Carolina, which, for those of you who don’t know, is a little town tucked in the Appalachian Mountains, and is considered by most as the “Berkeley of the South” for its inclusive and bohemian atmosphere. I went to college at a small liberal arts school and thought about a career in law while there, but I was hesitant to go straight into law school for the fear that I would find out later it really wasn’t my true passion. So, after I graduated, I took a job as a consultant at a major educational publisher.


Like most folks in their early 20s, I couldn’t quite figure out what I wanted to do with my life; but, I figured if I started to narrow down the things I didn’t want to do, I was making progress. My time in educational publishing let me know that career path was not for me. So, I moved onto the next venture, which was a 180 degree turn into the world of investment banking to pursue a career in banking. I also started my first company during this time, which, although it was an epic failure, taught me a lot about the struggles of entrepreneurship. Eventually, however, I decided to give law school a shot as for some reason I kept on feeling drawn back into a career in law.

I took a 180 degree turn and somehow landed an opportunity of a lifetime to work at a venture-backed startup. It was there that I “caught the startup bug” and began learning all things related to tech and the law.


While in law school, I found that my initial interests lied in litigation and criminal law; however, after several internship opportunities, I figured out quickly that a career in litigation was not for me. So, again, I took a 180 degree turn and somehow landed an opportunity of a lifetime to work at a venture-backed startup. It was there that I “caught the startup bug” and began learning all things related to tech and the law. After the startup’s eventual exit, I took a job back in investment banking, working primarily in the prime brokerage and derivatives space, and got my first taste of working with “Big Law”. While I learned a lot in that role, I do not miss the countless number of four eye reviews, quality control checks, and utter lack of creativity in the role.


After a little bit of soul searching and 1,000+ cups of coffee later, I eventually found Fourscore Business Law and took on a dream role as a startup attorney. Looking back at it, I think the experience growing up in an artsy, multicultural, quaint little mountain town helped show me that there is beauty in the odd, unique and non-traditional, as well as encouraged me to always follow my passions, no matter what other folks may think of your choices.

Why did you want to become a lawyer?

Ever since I was little, I’ve always been curious to know and understand how things fit into the big picture. My favorite toy as a kid was Legos®, mainly because I had the creativity to use these simple blocks which, individually, are nothing unique but collectively can be used to design something new and exciting. With that in mind, I guess I could have gone down two paths – I could have literally built things and become an architect or engineer or figuratively built concepts with words and concepts. As I grew up, my interests aligned more in the theoretical than physical space, which is probably why I ended up pursuing a career in law. As such, I’m able to design and create unique solutions for clients using the fundamental building blocks of the law to do so.

I could have gone down two paths – I could have literally built things and become an architect or engineer or figuratively built concepts with words and concepts. As I grew up, my interests aligned more in the theoretical than physical space, which is probably why I ended up pursuing a career in law.


Equally as important, I really enjoy learning about new businesses and ideas. Being a startup lawyer has given me the opportunity to have a diversity in my job I don’t think can be matched in most other professions. Whether it’s accounting for the risks inherent in beehive contracts (yes, this is a real thing) or figuring out disclosures that need to go in a private placement memorandum for a crypto mining startup, I get to learn something new everyday. It’s this opportunity to learn something new daily that makes me proud to say what few folks can - I get to wake up everyday excited to go into the office.

Was it a smooth road becoming a lawyer and getting to where you are now? If not, what are some of the struggles you encountered?

It’s easy to trace back the dots and try to create a linear story about how I ended up as a startup attorney. But, the truth is, my story, much like the clients I serve, has been (and continues to be) anything but a straight, predictable path. In fact, if I were to step back and trace my story, it would look more like a spider web, each line representing a number of successes, failures, and non-sequitur career changes that, when viewed independently don’t make much sense, but collectively seem to fit together.


One of my initial struggles was finding a good fit with a firm that aligns my personal and professional values. I think a lot of lawyers face this same struggle, and most don’t land their dream job coming out of school. It took some time to find a role that I wanted, but the key is to continue striving for where you want to be and be willing to take the leap of faith when you find it.

What are you most proud of as a lawyer? What sets your practice apart from others? What do you love the most about what you do?

I’m most proud of being able to help my clients grow their new ventures from nothing to something. Working for a number of years at large Fortune 100 companies and in Investment Banking made me miss being able to interact with clients on a more personal level. I love this part of my practice and I wouldn’t change it for anything else in the world (professionally speaking, of course).


Many of my clients are some of the brightest, most innovative folks in their respective fields. They took a huge leap of faith to start a venture on their own and an even bigger leap to trust me and the other attorneys at Fourscore Business Law as their advisors as they scale their businesses. I don’t take that responsibility lightly. I remind myself everyday the trust my clients have in the work I perform for them and the responsibility I have to ensure that it’s done in the most efficient means possible.


As such, at Fourscore Business Law, we integrate technology into everything that we do, make the engagement with us as efficient as possible, and create transparency in not only the type of work we do but also how we charge for that work. We’re working on new technology to help clients better quantify risk in their contracts as well as provide insights into the types of work we’re performing for our clients. We provide clients with up front, honest pricing and try to shy away from the billable hour if at all possible. We also work with clients to help them identify valuable investments now, such as creating legal templates and playbooks, so that they can reduce their legal costs in the future.


I love being able to use the skills I’ve picked up over the years as an attorney to be a small part of the reason my clients can grow, succeed, and disrupt.

If you could change, improve or disrupt one thing about the practice of law, what would it be?

I want to make corporate lawyers think and act more like the clients they serve. This means fundamentally changing the way that legal work is performed for clients to drive efficiencies into the practice of law. Other service industries figured this problem out years ago, so why should the legal industry be any different?


The best way to accomplish this is to utilize technology to automate the repetitive tasks, create an open and honest line of communication with clients especially as it relates to legal costs and returns on those legal costs, as well as giving clients tools to make better informed business decisions to mitigate downside risk.

Fortunately, gone are the days of law firms sitting around the conference room table figuring out ways to drive up billing for their clients, which creates friction on both ends of the spectrum. A new wave in the practice of law is coming


I hope that the things we’re doing today at Fourscore will help improve the practice of law to make it a more rewarding and enriching experience not only for attorneys but also for the clients they serve. Fortunately, gone are the days of law firms sitting around the conference room table figuring out ways to drive up billing for their clients, which creates friction on both ends of the spectrum. A new wave in the practice of law is coming – I just hope that Fourscore Business Law will be one of the lucky few able to ride that wave.

What are you doing when you're not lawyering?

When I’m not doing legal work, I enjoy spending time with my wife and new son. We love being outdoors and enjoying nature – whether that’s hiking on local trails or walking around the neighborhood, always accompanied by our lab mix and golden retriever. I also enjoy playing soccer, tennis, golf, and running as well as occasionally drawing and painting.

Wanna get in touch?
Contact
Address
16 W Martin St, Suite 9007, Raleigh, North Carolina 27601
Email
doug@fourscorelaw.com
Phone
828-545-0810
Follow
Instagram
facebook
@fourscorelaw
twitter
@fourscorelaw