When Ben Olive first entered the legal profession, the setting looked the way most people expect corporate law to look: polished offices, long hallways, plenty of distance between attorney and client. What it lacked, he recalls, was connection. “I worked in a very corporate environment that was not very, in my experience, personal,” Olive says. That realization became the starting point for what would eventually become Olive Judd.
From the beginning, Olive believed there was room for a firm that handled complex corporate matters without feeling institutional. “I thought there was a niche for a corporate law firm that did sophisticated work, but with a more personal feel,” he explains. That belief shaped every early decision, including where the firm would physically live.
Instead of opting for a high-rise address, Olive chose a retail-level space on Las Olas, one that allowed clients to walk in directly from the street. The building itself carried history. Before it housed the law firm, it was home to a linen company that serviced the marine and yacht charter industry, supplying napkins, silver and tableware to vessels moving in and out of Fort Lauderdale. The business had operated there for more than 100 years, long before Olive Judd took over the space 15 years ago.
That choice resonated immediately. Olive notes that “most of our corporate clients really prefer it to going into a high-rise in downtown and going up 24 floors, fighting for a parking spot, fighting for the elevator and having this impersonal reception area.” The experience was simpler, more approachable and more human, without sacrificing sophistication.
When Olive Judd opened its doors 22 years ago, Fort Lauderdale was a far quieter place. Olive remembers that “Fort Lauderdale did not have much of a downtown, had no high-rise condos, [and had] very [few] businesses attached to it.” There was potential, but not yet momentum. As the city grew, the firm grew alongside it, expanding steadily as Fort Lauderdale transformed into the commercial and residential center it is today.
That sense of timing became critical when Olive began looking beyond South Florida. A few years ago, his attention turned west. Tampa, he felt, mirrored Fort Lauderdale’s earlier energy. “Tampa had the feel of Fort Lauderdale 25 years ago,” Olive says, describing “this feeling that it’s about to explode.” The decision to expand was not driven by scale or speed but by familiarity.
Entering Tampa followed the same principles that guided the firm’s original footprint. Olive Judd again chose history over glass and steel, purchasing a building in the Hyde Park area that is more than 100 years old. Located near downtown and close to the water, the space reflects what Olive describes as “very much a local mindset because we want a more personalized, local feel.” While renovations continue, the firm has already established itself in the market, operating with the same philosophy that defined its Fort Lauderdale roots.
The similarities between Tampa and South Florida extend beyond architecture. Tampa’s professional sports teams, major developments like Water Street and an expanding business community signal opportunity. Olive points out that “there aren’t a lot of corporate law firms servicing the business needs of the Tampa community,” a gap that mirrors what existed in Fort Lauderdale two decades ago.
Trust, Olive believes, is built the same way, regardless of geography. “We do things better than our competition,” he says. That confidence stems from a focused structure, a highly concentrated group of attorneys and an emphasis on service. Olive takes pride in “our work ethic and our work product and the level of service we provide that is often missing in a larger institutional law firm.”
Success, however, is not measured solely by numbers. “The law firm’s success is not tied to revenue,” Olive explains. “It’s tied into creating great business relationships and creating new jobs.” Even before moving into the new Tampa office, the firm has already hired four attorneys and multiple staff members, with plans to triple that number once construction is complete.
For Olive Judd, the formula has remained consistent for more than two decades. Do the work well. Stay grounded in the community. Let growth follow naturally. In an industry that often feels distant, the firm has proven that proximity, both literal and figurative, still matters.
