Meet the Maestro of South Florida: Billy Cunningham, Unconventional Leader of the Starboard Group
In the fast-paced world of South Florida real estate, Billy Cunningham stands out as a dealmaker who turned his extensive network and entrepreneurial drive into a thriving real estate enterprise. As founder of The Starboard Group, Cunningham has crafted a unique approach that combines high-end development deals with a commitment to community building.
His entry into real estate wasn’t conventional. After running successful valet and marketing companies, Cunningham got his real estate license alongside someone he was dating at the time. While that relationship didn’t last, it sparked something bigger.
Billy Cunningham’s breakthrough in real estate came through an unexpected connection at the hotel where he operated his valet service. A longstanding client mentioned they were looking for a dry boat storage facility, and Cunningham saw an opportunity. Instead of just passing along the lead, he took action, methodically knocking on doors from West Palm to Deerfield Beach.
When a friend gave him a tip about the Pennell Marina and its owner, Cunningham’s entrepreneurial instincts kicked in. Walking into the marina, he faced initial skepticism from the owner, Mike: “Man, I got a lot of people that say that they got buyers for this,” Cunningham recalls him saying. But Cunningham took an unconventional approach. “I like, listen, I don’t need a listing, all I want is a commission agreement,” he says. The owner agreed, and Cunningham moved fast.
The very next day, he had the owners of Seagate arriving in their McLarens to view the property. The quick mobilization of serious buyers impressed the marina owner, who had been skeptical of brokers seeking traditional listings. The deal went under contract, and over the next couple of years, moved through the entitlement process before finally closing. While Cunningham notes he’s lost track of its current status, he believes it’s either being joint ventured or sold to another major development group for vertical development.
This marina deal became the catalyst that transformed Cunningham from a residential broker into a development dealmaker. Learning the intricacies of the entitlement process and large-scale development opened new doors, leading him to his current projects: a 498-unit development on a 17-acre site in Boston and a 750-unit project in West Palm Beach. As Cunningham puts it, “That Pennell deal kind of pushed me into understanding a different sector of real estate… Now that I’m doing this type of project, it’s a different wheelhouse.”
What sets Cunningham apart is his approach to relationship building and value creation. “I think when you do business with somebody, they should also be able to bring some substantial value,” he explains. “If that means introductions or other business – you make me money, I’ll help you in another facet that you might need.”
This philosophy has helped The Starboard Group evolve into what Cunningham calls a “full-service” operation. His team functions as a one-stop shop, combining residential and commercial expertise with development capabilities. The name itself has meaning – inspired by Cunningham’s Navy veteran father who suggested “starboard” (the right side of a ship) for one of his son’s first LLCs.
Looking ahead in 2025, Cunningham has ambitious plans. Beyond targeting $150-200 million in real estate sales, he’s focused on growing his own investment portfolio from 14 to 50 units. “My main goal for myself and my team is personally over 50 units,” he says. “If you want to get into real estate, you should be investing in real estate.”
The Starboard Group has also launched a non-profit foundation focused on financial literacy for kids. What started as a holiday toy drive has grown into a larger community initiative, with plans to expand their impact through affordable housing projects and community events.
For Cunningham, success in real estate isn’t just about transactions – it’s about being deeply embedded in the community. “When you remain humble and really understand the market where you’re at – not only know the neighborhood but know the restaurants to go to, the people to talk to when you need certain situations – being really involved in the community. I think that’s a really big piece of being a successful real estate agent.”
His outlook on the market remains optimistic, particularly for development. “I don’t think development’s ever going to stop because as things get old, they have to be replaced,” he notes, pointing to ongoing redevelopment opportunities in aging properties across South Florida. With multiple major projects in the pipeline and an expanding team, The Starboard Group appears well-positioned to continue its growth trajectory under Cunningham’s entrepreneurial leadership.
