BY SUSAN ROSE
Cover Art: Jax Black Car Founders Richard and Theresa Callahan near the Main Street Bridge in downtown Jacksonville. Photography by Chris Weiss.
After a cross-country move, Jax Black Car President & CEO Richard Callahan and Chief Administrative Officer Theresa Callahan seized on the endless opportunities their new paradise presented to them—including an unexpected opportunity to start a chauffeured transportation business.
When Theresa Callahan visited Jacksonville, Florida, while scoping out relocation cities for her family in 2010, she knew she was onto something wonderful. The Sunshine State’s northernmost city, just over the Georgia state line, was a hidden gem (and quite possibly love at first sight) for the Chicago native who was immediately enchanted by the lush landscape; miles of waterfront not only on the Atlantic, but from the bevy of lakes and rivers; luxurious homes and new construction; excellent school system; and thriving family and business community. Two years later, they packed up their lives, dogs (St. Bernards), and headed south.
L to R: Richard Callahan, Connor Callahan, Theresa Callahan, Chauffeurs Edward Madden and Scott Roberts, and Kelly Callahan at the Jacksonville Chamber of Commerce
“I’ve said since I’ve come here that Jacksonville was on the cusp of greatness and it’s absolutely true,” Callahan gushes about the River City she has called home for over a decade now. “I saw the possibilities of what was going to happen. This city continues to rank in the top 25 best places to live, raise a family, or retire in the United States. Many Fortune 500 companies are establishing offices here and real estate is on fire. Not only is the weather amazing, but the people are amazing. It’s just a phenomenal place to be.”
The move was in celebration of her husband Richard’s retirement from the Chicago Fire Department, a chance for the couple to start the second half of their lives in a different—and warmer—locale. At the time, their son Connor was just entering high school, while their daughter Kelly was already out on her own and building a career.
But mere weeks upon returning to Illinois after helping her family get settled in their new digs, Kelly too bid adieu to the Land of Lincoln and reunited with her family in Jacksonville, on Florida’s First Coast.
The luster of the move never wore off, but the appeal of “retirement” quickly did as the couple—who were used to always being on the go—found themselves tripping over each other, literally.
“The thing you must understand about Rich is that he is dedicated to public service. He spent four years in the Air Force, and then another eight years in the Reserves, then in the police and fire departments, and the union. His spirit of service led him to work for St. Johns County, driving school buses. And then before you know it, he’s not only a driver, but a CDL instructor, and then the president of the union,” says Callahan.
One of Jax Black’s Sprinters at TPC Sawgrass, home of the PLAYERS Championship, in Ponte Vedra Beach
Starting a chauffeured transportation company wasn’t on their to-do list, but Richard Callahan’s reputation as a safe and reliable driver didn’t go unnoticed by the locals—especially the legacy families who were willing to pay for private transportation for their children.
Around that time, ride-sharing apps (you know the ones) were becoming popular to some but not so much to a more select group. “Prominent families and high-net-worth individuals in gated communities like Ponte Vedra Beach, a cherished oceanfront vacation destination and home to many accomplished people that tend to have discerning, sophisticated tastes, preferred Richard far and above to be their personal driver. He was someone they could always reach 24/7 and whom they trusted their family with. Accustomed to a certain lifestyle, VIP service, and exclusive access in all aspects of their lives, they embraced the secure ground transportation and concierge service that Richard offered,” says Callahan.
Richard’s enterprise began to blossom into a full-fledged business, thanks to word-of-mouth recommendations, and before long he went from being a sole proprietor in 2013 to an incorporated business called Jax Black Car in 2015.
“He started by driving exclusively for prominent families, and then it just slowly built by referrals. These families trusted him with the inner workings of their lives, their private schedules, and most valued treasure, their children,” says Callahan.
Richard and Theresa looked at each other and said, “You know, we can do this. That’s when we founded Jax Black Car. Our fleet began to expand to include top-of-the-line Volvos, Escalades, Mercedes-Benz Sprinters, and minibuses. We just grew and grew,” says Callahan.
On Callahan’s part, she drew upon her background in corporate sales to tackle the operations and marketing side of the budding business, while Richard focused on catering to his VIP clientele.
Part of a brotherhood: Richard Callahan, retired, Chicago Fire Department, with Eddie Madden, retired, Fire Department New York
At the same time, their daughter Kelly was a rising star at Starbucks set to be a district manager in Florida. Kelly was trained and developed an invaluable skill set in a myriad of crucial business practices including hiring, safety, customer service, even legal issues.
Knowing that Kelly was on that trajectory, Callahan wasn’t sure how the conversation would play out when she asked her firstborn to join the family business, but she was thrilled when she not only accepted but relished the challenge to take on the operations.
“Kelly is brilliant! She has the drive and the knowledge, so it was kind of the perfect storm,” says Callahan. “She has expanded the company beyond what I thought possible—she’s our rock star.”
One of the first things that Callahan did was connect Kelly with Arthur Messina’s Going Global peer group for affiliate managers, an area of the business that they were looking to grow. Callahan says she also brought her daughter to the shows, including the CD/NLA Show, which is where she herself had forged a network of industry mentors and friends over the years. “If I could offer advice to any new operators out there who are trying to get their footing, I would tell them to stick their head in those meetings and learn everything they can at these events. Develop relationships early on with other operators in your town because you will need them if you want to be successful and don’t be afraid to talk to the competition because this industry is very welcoming,” she says. “If it wasn’t for the other women in this industry—Tracy Salinger of Unique Limousine, Diane Forgy of Overland—I probably wouldn’t be here. Kelly went all over the country with Going Global, establishing relationships, learning from other operators, and seeing the inner workings of their businesses.”
While all the major cities in Florida have pockets of wealth and established families, Jacksonville really does stand out from its counterparts, according to Callahan. In contrast to Miami’s sizzling international nightlife and its access to the Keys, or Tampa’s and Fort Myers’ Gulf Coast vistas, or Orlando’s famous kid-friendly theme parks, Callahan says that the Northeastern corner of the state is focused squarely on building strong communities, where businesses and families alike can thrive.
Tourism of course plays an important role in their local economy—opulent resorts of all kinds (including golf) dot the coast stretching dozens of miles from Amelia Island to St. Augustine—but so too does its burgeoning corporate presence. The sprawling metropolis is transected by I-95 from the north and I-10 from the west, with an award-winning airport, many FBOs, and helipads spread throughout—the First Coast is perfectly positioned for Fortune 500 companies, the C-class, traveling executives, and domestic and international tourists eager to enjoy the magnificent coastline.
L to R: Richard, Theresa, Connor, and Kelly Callahan on Jacksonville’s Saint Johns River
That prosperity is also a clarion call for many younger professionals who continue to flock to the destination that has the best of all worlds: strong economic growth, no state income taxes, endless outdoor recreation, and to-die-for weather. Jacksonville gained more than 130,000 people in the past few years (in comparison, Orlando, the second-fastest growing Florida city gained about 50,000) and is nearing 1 million residents.
The influx of new residents has enabled the city to revitalize downtown. Much of the once dilapidated downtown is now being rebuilt and award-winning restaurants with gourmet menus and rooftop bars now stand in their place.
The PGA tour calls Ponte Vedra its home and TIAA Stadium, the home of the Jacksonville Jaguars, was most recently renovated in 2016 to accommodate the growing attendance. Continual development is underway around the stadium: The team’s owner and Jacksonville benefactor, Shad Khan, is working in partnership with the leaders of the city to build a complex of entertainment, hospitality, and sports, and Jacksonville is quickly becoming a yachtsman’s town with a brand-new marina that will offer the best boating, no matter its size, to the legendary waterfront city. And did we mention the weather?
The Callahans are currently on the hunt for bigger and better offices and large enough space to house all their vehicles. “We need space to park the new vehicles we are adding to our fleet. One of the downsides has been the lack of vehicle inventory, but that is changing,” said Callahan. They recently purchased another Escalade and a Sprinter and are set to take delivery on another Sprinter at the end of the month.
“This business community welcomed us with open arms, and we’re really grateful for the different organizations that have embraced us,” Callahan says, which includes chambers of commerce of St. Johns County, Nassau County, and Jacksonville as well as the St. Augustine Visitors and Convention Bureau, to name a few. “It wasn’t necessarily easy, we still had to work very hard to grow our business, but it was a no-brainer. The people and the city of Jacksonville made it very doable, the opportunities are here, and we make sure that we have our foot in every door.”
The pandemic experience in Florida was in stark contrast to the US coasts, which were slower in relaxing the sizes of gatherings and masking. Early on, cruise ships lay abandoned, flights were severely reduced, and even Disney World, which had only shuttered for hurricanes and 9/11, closed for more than four months. But by late summer 2020, most of the state was operating close to normal, even if in a limited capacity (the cruise industry took longer).
“We were very fortunate that our state mostly remained open during much of the pandemic,” Callahan said. “Don’t get me wrong, the bottom really fell out in March 2020. All the events stopped, the hotels laid off thousands of people, and many of my chauffeurs were sent home. It was a tough time for everybody. But we were fortunate to have our Delta Airlines shuttle crew contract—those planes had to fly—and our high-net-worth clients and private aviation partnerships kept us moving. We never stopped answering the phone even when some of our competitors shut down 100 percent. We couldn’t.”
While it felt like the world hit pause, life was still happening despite the virus. “Jacksonville’s prestigious medical community continued to provide lifesaving transplants during this very uncertain time and our private aviation partners who transport organs to the medical centers remained in constant contact with us,” says Callahan. “Patients who were traveling via private jet for these treatments were often terrified. But we made sure that they were comfortable as they were greeted by our professional chauffeurs who transported them to their critical procedures.
“We had commitments and obligations and we had to fulfil them,” she continues. “It was difficult, but we are much stronger today than we were before the pandemic. Our 5-year plan turned into a 10-year plan, but that’s OK, we are in such a fantastic position now, and we are eager to build on this phenomenal foundation.”
Moving in the right circles and making the right connections is certainly an advantageous strategy for any business, but the Callahans have another ace up their sleeves: many of their chauffeurs are retired NYPD or FDNY. Florida is a mecca for retired service men and women, many from the Northeast, and the brotherhood among the network is strong. Most are young enough to want to pursue a second career that offers flexibility and positive interactions with the public, while clients have peace of mind knowing that a highly trained professional is behind the wheel, and they are in secure hands. This is especially true for those VIPs who might have extra security concerns.
“We’re now at the point where our phones are ringing 24 hours a day. Most of the team is part time because they can do it from home, so you can say that we were ahead of the curve on remote work,” says Callahan. “We work with Linda Forde from the Forde Firm; she is our part time CFO and an incredible part of our organization. Philip Hess is our creative director, handling marketing, advertising, and our social media team. I’m lucky to be surrounded by phenomenal, dedicated people.”
This year, a fourth Callahan will be a part of Jax Black Car full time. Their son Connor will also be joining the family business and is following in his father’s footsteps on the fleet side by working toward his CDL.
Callahan says that Kelly, who is now the company’s director of operations and affiliate manager, has developed their affiliate network to a comfortable level while also continuing to expand their local client base.
“When your affiliate partners are asking for your chauffeurs by name, you know you’re doing something right,” says Callahan. “We were given this opportunity by our community to start our business. They came to us because they trusted us, and the city helped us grow exponentially. We earned the trust of our industry partners and today, the dedication and hard work of our entire team is bringing us to the next level.” [CD0422]