Jen Gregory didn’t have time to think about the life changes she’d have to make as she plummeted 12 feet from her mother’s attic toward the concrete floor below. She barely had time to register what had happened as she stepped onto what she says looked like solid wood in the dim light of the roof space but was merely particle board.
The following months, however, afforded Gregory that opportunity in spades.
Above all, Gregory, 46, says she was grateful her injuries weren’t worse. This might sound like an odd claim for a person who has a titanium rod in her left leg – and who endured several surgeries and months of excruciating physical therapy in the wake of her bone-shattering drop – but she didn’t blink.
That’s because Gregory knows things could have gone even farther south than they did.
“My surgeon said a lot of people who have similar falls wind up paralyzed,” Gregory says. “I’m truly fortunate.”
No one has argued that point with Gregory. But people have expressed that it’s unfortunate that her diminished mobility at the time forced her to leave a profession she loved.
Food fight
Nothing says love like a tattoo. Just ask anyone with someone else’s name branded on their skin. Or ask Gregory, who loves the restaurant industry and has the ink to prove it.
A self-professed wine geek, Gregory has a tattoo of a giant corkscrew on her right arm. The implement is so big, it could open a 55-gallon drum of wine if it were real. Stretched across the lower half of the arm, the tattoo declares in no uncertain terms that Gregory loved her job.
“I was in the food service industry for 25 years,” she says. “I loved the hustle and the sense of community.”
A Chattanooga native, Gregory filled several managerial roles during her years in restaurants, which included stints at Mellow Mushroom, Hair of the Dog, Easy Bistro and other local establishments.
Gregory also supported her food service colleagues through various volunteer efforts, including founding the local chapter of the United States Bartenders Guild and launching the Chattanooga Service Industry Fund at the onset of the COVID-19 pandemic. The latter granted $24,000 to 200 local restaurant workers who had no means of support after COVID shuttered places of business.
“These were people who made their money on a daily basis and couldn’t budget even a week out for food. All of a sudden there was no work, and many of them couldn’t put couldn’t put food on their table or pay their rent.”
Gregory was working as the sommelier at Easy Bistro in 2016 when she crashed through the rafters of her mother’s house while retrieving Christmas decorations. She was unable to return.
Fortunately, Gregory had experience working in another industry in which being in an aircast or on crutches would be less of an impediment: real estate.
Starting over
Gregory plunged into real estate at a time when the land was flowing with milk and honey. In her case, the land was Florida and the river from which she drank was the real estate boom of the mid-2000s.
It was a time of abundance. Gregory took a job with a title company after moving to the panhandle in 2004 and later aimed to uncork her earning potential by becoming a licensed Realtor. Upon receiving her credentials, she worked for a developer who built luxury mixed use projects. Gregory’s average sales price during this bonanza was $1.2 million.
Gregory also assumed a management role at her office. She says the position felt familiar to her despite her status as a relative tenderfoot in the industry.
“Restaurant management prepared me to lead a real estate office,” Gregory recalls. “It taught me how to manage personalities, which is what we do in real estate. Whether you’re leading an office of 450, managing a team of 12, or are in charge of only yourself, you’re managing personalities. That comes naturally to me.”
People who are familiar with the history of the real estate industry could likely predict what happened next. However, it bears mentioning because the housing crash impacted every agent in a personal way.
When the bottom dropped out of Gregory’s business – in what one could contend was a bit of foreshadowing – she retired her license and returned to Chattanooga to lick her wounds.
“It was a humbling life lesson,” Gregory says. “It taught me about being fiscally sound.”
At the same time, real estate had provided Gregory with a foundation on which she could stand again if she ever needed it. And as she recovered from her injuries, she needed it.
That said, Gregory didn’t return to real estate only because she needed it. She might not be sporting a tattoo of a house or the logo of the National Association of Realtors, but much like she loved serving diners and her fellow food service employees, she loves serving homebuyers and sellers, too.
“I returned to real estate partly out of necessity and partly because I missed it,” she explains. “I was in several different aircasts and used crutches for over two years, so I wasn’t going back to food service, but I could show a house. At the same time, I missed being in this world.”
Gregory picked Keller Williams as her brokerage to take advantage of the ample resources the company pours into its agents’ businesses, she says. Out of the local offices, she chose to hang her license at Keller Williams Greater Downtown Realty because its female leadership (which includes team leader and CEO Hope Brazzell, operating principal Jennie Brockman and others) inspires her, she adds.
“Strong female leadership is important to me.”
And business is good again for Gregory. She’s among the top 20% of producers at the office – which boasts the largest collective of agents in the Chattanooga area – and she’s tallying about $8 in annual sales.
That’s enough business to keep Gregory busy, although it’s not her focus, she says.
“I don’t love the obsession with numbers in this business. Real estate is a people business. I’m doing well, but my most important measure of success is whether or not my clients are happy with the decisions they’re making.”
Entering public service
As Gregory eyes the future, she’s seeking to add herself to the roster of local female leaders. Like Chattanooga Realtor Sabrena Smedley, who served on the Hamilton County Commission from 2014-2022, Gregory is aspiring to serve in public office.
Gregory is one of four candidates (as of Jan. 23) whose names will be on the ballot in March to fill the vacant District 6 seat on the Chattanooga City Council. The seat, which encompasses the Hickory Valley, Silverdale and Tyner Hills neighborhoods, was emptied with the death of incumbent Dr. Carol Berz in December.
Like her opponents – which include Kitchen Incubator director Mark Holland, real estate appraiser Christian Siler and Jenni Berz, daughter of the late Dr. Berz – Gregory wants to help the city of Chattanooga address its most pressing issues. She says these include the lack of sufficient affordable housing, the need for better health care advocacy and more.
Gregory’s bid for office also stems from a desire to teach her nieces to not place any limits on their ambitions.
“I have three young nieces,” Gregory smiles. “I want them to know that everyday people can do these kinds of things. You don’t have to be a perfect person or have experience in politics to run for office. You can figure it out like everyone else.”
Gregory has aided two female candidates in their quests for public office – with mixed results. In 2016, she managed the District 5 campaign of Katherlyn Geter, who squeaked past 14-year incumbent Greg Beck with 15 votes.
Gregory also managed attorney Melody Shekari’s campaign for a seat in the Tennessee House of Representatives in 2018. Shekari placed second in a field of five candidates and went on to become the executive director of the Women’s Fund of Greater Chattanooga.
Now it’s her turn to try, Gregory says. Although she insists she’s a people rather than a numbers person, she quotes a few statistics in an effort to encourage more people to vote than in past elections.
“District 6 is home to 20,000 people. Of those, 12,000 are registered to vote. Yet only 10% of those voters turn out for municipal elections. That’s 1,200 people. We can do better.”
In the meantime
Gregory has been sitting in a lounge at her brokerage on a chilly and wet Saturday morning in January. In stark contrast to any weekday, the office is empty and therefore quiet except for her voice.
While Gregory claims she generally doesn’t notice the titanium in her leg, the wintry weather is making it hard for her to ignore the implant. Regardless, she’s looking forward to the afternoon, as she and a client will be touring several houses in their search for a home.
When Gregory’s work for the day is done, she’ll return to her home and her two “very vocal” dogs. If it were any other season of the year, she might take them for a hike or go kayaking or seek out good food and even better wine.
Gregory is thankful for this life. Although she misses restaurant work, she enjoys real estate and has a mission to complete.
“It’s been a long road since the accident,” Gregory says. “I’m delighted to be at the end of it and at the start of another one.”