“I'M A RECOVERING LAWYER,” Anthony Vittone, R’90 and L’93, sometimes quips when he introduces himself.
The phrase speaks to the unconventional trajectory of his career — from law school graduate to executive vice president and chief operating officer of DroneUp, one of the nation’s leading drone delivery startups. But to view Vittone’s story as a simple transition from law to business would be to miss the nuanced interplay of legal expertise, entrepreneurial spirit, and technological innovation that has defined his professional journey since leaving Richmond Law.
Vittone has always had entrepreneurial and creative streaks alongside his legal interests. In his days as an undergraduate at Richmond, he made and sold pen-and-ink drawings of campus buildings in the campus bookstore and at Arts Around the Lake. “I did anything I could to make money,” says Vittone, who met his wife, Katherine Salley Vittone, B’91, on campus. “[Her] engagement ring — I paid for that out of selling artwork on campus.”
He has combined these instincts with his legal training to build a career outside of traditional law practice but still on the foundation of his training at Richmond Law and experience as a lawyer.
A TRADITIONAL START
After earning his law degree in 1993, Vittone began his legal career in a conventional manner, joining the law firm of McGuireWoods as an associate. He gravitated toward the firm’s burgeoning intellectual property practice, drawn to the creative aspects of the work. “I’ve always had this sort of creative bent,” Vittone says. “The intellectual property department gave me that outlet of working with people who are creating things, whether it be inventions or artistic works.” After a few years there, he moved to Mezzullo & McCandlish, where he focused on corporate law.
Even at this early stage of his career, he was starting to bridge the gap between legal considerations and business objectives.
“When you’re in a law firm, you’re really just looking at a transaction based on [the legal] issues,” Vittone says. “It’s not your job to think about whether it’s a good business transaction for the company, but I always had thoughts about that.”
Vittone’s musings became his focus and responsibility with his next professional step. In 1999, he took a position with a privately owned gaming company called Decipher, which specializes in licensed card and board games. As both general counsel and vice president for business development, Vittone found himself negotiating deals with entertainment giants like Lucasfilm and Paramount Pictures. “It was fascinating,” he says. “I grew up in the time when Star Wars [first] came out, and here I am negotiating with people that work with Lucasfilm.”
The Decipher role marked a pivotal moment in his career evolution. “This is where I first began getting involved on the business side as well as being a lawyer,” he says. “I could have conversations about the economics of the transaction and the business justification. What I loved was working out ways for both companies to say, ‘You give me this, I can give you this. It makes a better deal for you, makes it a better deal for us.’”
This ability to understand both business implications and legal considerations has been key to his subsequent professional endeavors. At DroneUp, it informs every aspect of his work, from regulatory negotiations with the FAA to strategic partnerships with retail giants. “My first instinct when I come to a business deal or business discussion is to look at it from the business side,” he says. “Then I’ll layer on the legal afterward.”
EMBRACING THE STARTUP MINDSET
The path of Vittone’s journey from traditional legal practice to a gaming company to drone technology was anything but linear. It required a willingness to learn new industries and technologies and embrace the uncertainty of startup culture. This shift in mindset developed significantly during his tenure at Swimways Corp., which hired him away from Decipher in 2004. He would spend the next 14 years there in an ever-expanding role.
Vittone was first hired to set up the company’s internal legal department. Once he did that, his responsibilities grew consistently. “Every year to year and a half, the CEO would ask me to take on another department,” he says. “I really started to think of things in a business context.”
At Swimways, Vittone’s purview expanded to include global operations, product development, and strategic initiatives. He opened offices in Hong Kong and Guangzhou, China, establishing manufacturing and sourcing operations. He created an inventor submission program to fuel product innovation and established a product integrity department. “I learned a lot,” Vittone says of his time at Swimways. “It became a core business experience for me in the sense that it was something completely outside of the legal realm.”
“I’ve always had this sort of creative bent. The intellectual property department gave me that outlet.”
Up to this point in his career, his business acumen had been decidedly DIY — keeping his eyes and ears open, finding mentors and advisers, and learning from mistakes and near-misses. The CEO at Swimways, recognizing Vittone’s growing potential, encouraged him to pursue an MBA on the company’s dime. Vittone enrolled in the MBA program at the College of William & Mary, attending classes every other weekend while working full time, an experience he said significantly strengthened his business skills and decision-making. He finished the program in 2011.
“There’s something about going back to school when you’re older,” Vittone says. “Every class was just fascinating. It really rounded out my self-taught business learning and gave it a more formal structure.”
Another professional turning point for Vittone came when Swimways was acquired by a larger public company in 2018. The bureaucracy of the new environment clashed with his entrepreneurial instincts. “I’m used to making five different decisions before lunch,” he says. “Publicly traded companies are like, ‘Submit five different decisions to 10 different committees for them to maybe make a decision in two months.’”
After helping through the transitional period, he started looking for new options. Vittone joined DroneUp as its first full-time employee in 2018, eager to return to a more nimble environment. The fledgling drone company offered the opportunity to leverage both his legal expertise and his business acumen in an emerging industry.
“Not only is it a startup, but it’s a startup in a startup industry,” Vittone says. “If you create a T-shirt company, you might be a startup, but you don’t have to explain to anyone what a T-shirt is. We have to explain to people what drones are and all the different ways that they can be used because we’ve only just scratched the surface of what this technology can do.”
SHAPING THE REGULATORY LANDSCAPE
Perhaps nowhere is the value of Vittone’s legal background more evident than in DroneUp’s efforts to navigate and shape the complex regulatory environment emerging with commercial drone operations. As a new technology, drones present unique challenges to existing aviation regulations. Vittone has been at the forefront of efforts to educate regulators and lawmakers about the potential of drone technology while ensuring safety and privacy concerns are addressed.
“A lot of our regulatory efforts have been giving the FAA the assurance that we can do this and do it in a safe way,” Vittone says. He played a crucial role in DroneUp’s efforts to obtain Part 135 Air Carrier certification from the FAA. DroneUp is the sixth carrier in the nation to receive the certification. “It’s a big accomplishment for us,” Vittone says. “It basically certifies us as an air carrier to carry goods for other people and to carry them beyond line of sight.”
Vittone’s involvement has extended to helping shape federal legislation. He was a key voice from the industry providing input for the 2023 FAA Reauthorization Act. In particular, he spearheaded an industrywide effort to achieve bipartisan support for expanding “beyond visual line of sight,” or BVLOS operations, a regulatory update that is essential for the industry’s future. This demonstrated the unique value his legal background brings into his emerging industry. “I think that a law degree gives somebody a lot,” Vittone says. “You cannot operate a business in the United States without lawyers. It becomes a good basis for running a business, and you get exposed to a lot of different issues and things that lots of people don’t.”
As chief operating officer at DroneUp, Vittone is not just navigating the current landscape of drone technology and its regulatory environment — he’s actively shaping where it is headed. “Drones are going to get to the point where they’re going to be incorporated into everybody’s business,” he predicts. “It’s just a question of how and when that comes.”
Vittone envisions a world where drone delivery is as commonplace as traditional shipping methods. He sees potential applications far beyond retail delivery, including emergency medical supply transport, infrastructure inspection, and environmental monitoring. However, he’s also mindful of the challenges that lie ahead, from public perception issues to regulatory frameworks needing to evolve further.
LESSONS FOR LEGAL PEERS
Vittone’s trajectory speaks to the breadth of opportunities a law degree can open up. When he was in law school and then practicing early in his career, Vittone didn’t hear much about options beyond traditional law firms or public interest work. “There wasn’t enough attention put on the fact that you can go to law school, but you don’t necessarily have to go be in a law firm,” he says. “You can go into a company and be in-house, or you can also go into a company and not even be in the legal department, but just use the law degree as a jumping-off point into a larger career somewhere else. Your law degree can take you to places you might not expect. Be open to opportunities that might not fit the traditional mold of a legal career.”
Embracing entrepreneurial thinking and seeking out diverse experiences have been key to his professional path, he says. “Every role I’ve had has taught me something valuable. Don’t be afraid to take on new challenges or step outside your comfort zone.” ■
Photos courtesy of Anthony Vittone.