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A legal education from Maryland Carey Law prepares students for a wide range of career paths. Meet three graduates who are using their JDs as entrepreneurs.
Ahead of the Curve: Ethan Caldwell ’95
As a young assistant state’s attorney on Maryland’s Eastern Shore, Ethan Caldwell ’95 planned to enter the world of politics but changed course when opportunity knocked in the form of a Seattle-based technology startup.
“The opportunity was not far removed from the stereotypical image of a group of engineers setting up shop in a garage,” says Caldwell.
While his trusted friends and mentors thought the risk was too great and advised against taking the job, Caldwell forged ahead. “Not realizing I was demonstrating a classic entrepreneur trait, I went against the grain, took the risk, and accepted the job,” he recalls.
So began Caldwell’s journey as a serial entrepreneur.
The startup, go2net, was a web portal he joined and managed—with its fast-track initial public offering (IPO) ultimately merging with another public Seattle tech company in 2000.
In 2002, Caldwell co-founded Marchex, an ad tech company, which also undertook a fast-track IPO.
Some 17 years later he and his family moved back east to their favorite city, Charleston, and he joined one of his startup investments, MixMode, a California-based cyber security company.
Caldwell credits Maryland Carey Law for preparing him for his professional path. “Today, nearly 30 years since graduating, it is clear to me the analytical and critical-thinking skills I developed in law school have been foundational to my entrepreneurial career,” says Caldwell. “Start-up businesses are multi-faceted, requiring founders to have exceptional problem-solving abilities.” He notes how law school students are challenged under pressure to learn to identify issues and assess solutions—a perfect alignment with the demands of an entrepreneur.
Lawyers, he adds, are essential in the tech world—to facilitate commercial transactions, assist with mergers and acquisitions, intellectual property management, corporate governance management, as well as state, federal, and international regulatory compliance.
“The legal knowledge and problem-solving skills Maryland Carey Law provides its students uniquely prepares them to succeed in demanding and fast-paced technology companies,” he says. “Having worked with many lawyers nationwide, I can attest, our graduates can add tremendous value in entrepreneurial ventures. Landing positions will take determination, persistence, resilience, and a little luck, but these are fundamental traits of all successful entrepreneurs.”
Caldwell encourages Maryland Carey Law graduates to be new technology early adopters and to build and maintain law school connections, both face-to-face and through digital networks. He also advises aspiring entrepreneurs to embrace that failure is continual and around every corner. “Competition in the tech industry is mindbogglingly fierce,” he notes. “Evolving legal and regulatory environments must be continually monitored to ensure effective compliance and risk management, and entrepreneurs are challenged every day to find fast solutions that balance business needs with dynamical risks.”
Today, Caldwell is experiencing a new learning curve at MixMode, which he says fits the bill of a disruptive technology capable of grabbing market share in a crowded digital space. His previous companies were built largely through the incorporation of technologies acquired through merger and acquisition transactions. “MixMode's cyber threat detection was developed in-house, under the direction of one of the world's leading artificial intelligence (AI) experts,” says Caldwell. “Helping to build and run a product-focused, high-growth tech company with homegrown technology is new to me and represents a departure from my bottom-line-focused prior technology companies.”
Caldwell believes the coming wave of AI innovations will contribute to greater business and consumer transformations than any prior tech period, offering incredible opportunities for entrepreneurs with legal backgrounds. “The problem-solving skills and versatile skill sets of Maryland Carey Law graduates are ideal for entrepreneurial ventures,” he says, “and I am excited to see the leadership roles our alumni play in the upcoming AI-led innovation wave.”
An Enterprising Spirit: Toni Gilliard ’01
Toni Gilliard ’01 is no stranger to the challenges faced by immigrants to the United States. As the stepchild and grandchild of people from Barbados, her early family experiences sparked an interest in immigration law.
“Maryland Carey Law offered me the chance to build my own map and pursue my dreams,” says Gilliard. “My end goal was never to work at a large, corporate law firm but to start my own firm.”
That’s exactly what she did.
Gilliard hung out her shingle and practiced immigration law for 17 years before transitioning to a career in real estate. “It was a natural fit for me as I often worked with immigrants seeking retail space for new ventures.” Through the years, Barbados was always top of mind, especially after completing a study abroad program there her 1L summer. A brief vacation to Barbados in 2018 solidified the foundation for her latest entrepreneurial venture Tipsy Lady, Inc., a premium Caribbean-inspired canned cocktail company.
For more than 20 years, friends and family had been impressed with Gilliard’s rum punch concoction, a favorite at get-togethers. During her 2018 visit to Barbados, she watched the work ethic of the women shop owners and women who owned rum factories in action. “I witnessed the trajectory of women in power in the spirits industry,” recalls Gilliard, pointing to the female master distillers for Appleton Estate and Mount Gay Rum as examples.
A year of research and development followed her trip, during which time she perfected the formulation for a ready-to-drink rum punch. “I wanted the drink to reflect my culture and be authentic, using premium spirits and spices in Caribbean-inspired flavors,” says Gilliard. “I also wanted to strategically align with partners who reflect cultural diversity within their communities.”
Throughout the product development process, Gilliard says her law degree gave her much-needed credibility in a predominantly white male industry. “In conversations about contracts and negotiations, I could leverage my degree and experience,” Gilliard describes. “Maryland Carey Law gave me the background to research permits and understand the laws that govern the industry and related agencies, including dealing with the Alcohol and Tobacco Tax and Trade Bureau under the Department of Treasury.”
Gilliard thinks some people, including herself, are born with the entrepreneurial bug. “I always had a side hustle, beginning with selling a variety of food items with my grandmother in Harlem as a young girl in the summertime,” she recalls. “And my great-grandfather was a real estate investor. I believe it is how I am wired.”
Law school, she observes, can serve as an important step in transforming that entrepreneurial spirit into a profitable business. Gilliard advises aspiring entrepreneurs to tell their stories in creative and compelling ways to differentiate their brands and to confidently use skills built in law school to negotiate advantageous terms and deals with both clients and competitors.
One way she is differentiating her own brand is through her company name, Tipsy Lady, which is more than a lighthearted reference to the drink’s alcohol content. The moniker, Gilliard explains, also addresses the idea of tipping the scales—as they relate to company ownership and women of color—in the alcohol industry. She is firmly committed to building a business to pave the way for future entrepreneurs. “The goal for me is to give back to other small businesses and youth programs that support entrepreneurial endeavors,” she relates. Gilliard has also expressed an interest in funding affordable housing in small communities.
With three flavors selling at stores in South Carolina and Florida and through online sales at tipsyladycocktails.com, Gilliard says her greatest challenge now is growing the business and expanding the product line. The next step is to seek venture capital funding. To accelerate her options, Gilliard incorporated Tipsy Lady in Delaware. “I had the legal knowledge to navigate that process,” she says. “I know where I have to be if I want to sell the business in the coming years.”
Health Influencer: Jason Brooke ’10
Jason Brooke ’10 hadn’t planned to attend law school. “I wanted to be a physician who designs medical devices,” remembers Brooke, who holds a BS in biological resources engineering from the University of Maryland, College Park, and an MS in biomedical engineering from Johns Hopkins University. He began his career as a research scientist/engineer in the medical device industry, designing algorithms for pacemakers and implantable defibrillators, but realized that reaching his goal to be chief executive officer of a small medical device company, required additional skills.
Skills he would gain at Maryland Carey Law.
In law school, Brooke increased his understanding of the medical industry as he pursued a Health Law Certificate and on the staff of the Journal of Health Care Law & Policy, a forum for the interdisciplinary discussion of leading issues in health law, medicine, and health policy. He further developed his policy acumen and boosted his management skills as the journal’s editor-in-chief, leading a team of nearly 40 journal staff members.
The Socratic method of teaching, which requires quick critical thinking, is used in some doctrinal courses at Maryland Carey Law. Brooke says those rapid-fire dialogs were also great training for his career as an entrepreneur. “We constantly must answer questions on the fly, provide immediate strategic advice, and think critically on our feet regarding issues of substance,” says Brooke. “I also learned time and team management and how to prioritize the steps required to solve any problem.”
Following graduation, Brooke applied his diverse background as an attorney at Epstein Becker & Green—a national health law firm—and subsequently as chief executive officer and general counsel at Vasoptic Medical Inc., an early-stage medical device company developing an innovative vascular imaging technology for various applications, including early detection of diabetic retinopathy and augmented reality neurosurgery. Brooke grew the company he founded to the point of product commercialization and beyond.
“Over time, I came to realize there is great potential as a lawyer and adviser to medical device companies,” says Brooke. “Leveraging a law degree and engineering and medical device experience, I was well positioned to assist companies in bringing their products to market.”
In 2012, Brooke turned his entrepreneurial attention to his legal and advisory firm, Brooke & Associates, where he and his team advise clients of all stages, sizes, and clinical, therapeutic, and technological domains on issues critical to the medical device, digital health, and digital therapeutics industries, with a particular focus on software medical devices.
Among his clients are startups developing radiological imaging analysis software and wearable sensors for vital sign monitoring at home to academic medical institutions developing augmented reality/virtual reality diagnostic and therapeutic solutions for neurological disorders to publicly traded companies developing artificial intelligence/machine learning-enabled software for diagnosing and managing depression, respiratory diseases, and life-threatening cardiac events. Brooke & Associates provides legal counseling and advisory support to innovators. They ensure compliance with regulatory requirements for medical devices, including advising on and implementing optimal strategies for obtaining FDA market authorization and managing enforcement actions; developing, auditing, and remediating quality systems in compliance with regulatory requirements; and handling post-market surveillance activities.
The bonds forged with fellow students during law school have served Brooke throughout his career. He recalls, “When I was at Maryland Carey Law, faculty always emphasized how important law school friendships would be in the future. I could never have anticipated my interactions with former classmates would be so valuable.” He continues to rely on those relationships, working with former classmates who specialize in complementary legal domains.
Brooke is taking a critical role in the industry and has a proven history of influencing regulatory policy in the medical device and digital health space. As co-chair of the Digital Therapeutics Working Group of the Consumer Technology Association, he leads organizations in the digital health industry in the development of standards for companies creating innovative "digital therapeutics,” the next wave of medical devices.
He attributes much of his success to his Maryland Carey Law education. “Without the legal foundation established during my time at the law school, I would not be where I am today,” Brooke says. “The exceptional faculty, particularly in the Law & Health Care Program, and the talented and diverse student body created an environment where my skills could grow and flourish.”
The above stories were originally published in the 2024 Maryland Carey Law magazine. Written by Nancy Grund.