To say T.J. Gentle loves football would be like saying Peyton Manning showed promise as a Vols quarterback. It’s not up for debate.
There was even a time when Gentle – a Jasper native who played ball for TSSAA Hall of Famer Ken Colquette of Marion County High School – possibly wanted to become a football coach, he says. However, Colquette steered him in a different direction.
“He said, ‘Be a doctor or a lawyer, but no matter what you do, don’t become a football coach,’” recalls Gentle, 46. “I’ve told him since then that I probably did want to become a football coach. He basically said, ‘For you, that would have been settling, and I didn’t want to see you do that.’”
With Colquette’s advice lodged in his thoughts, Gentle packed his bags, put his childhood home in his rearview and became a Blue Raider. When he wasn’t tearing up the gridiron as a linebacker for Middle Tennessee State University’s football team, he explored the topics of law and medicine in the classroom.
The law “worked,” Gentle says. Just as influential to his future was his stretch at Citizen’s State Bank in Jasper, where CEO Geoff Post nurtured an interest in business in him.
By the time Gentle arrived at the University of Tennessee College of Law, he was keen on learning more about the crossroads of business and the law. The corresponding classes initially reinforced his intentions and later gave them clarity and purpose.
“I realized there are people called corporate lawyers who help other people buy and sell businesses. And, lo and behold, there was Miller & Martin, which had been doing it for 125 years at the time. So I came here to work with a fantastic group of attorneys.”
As Gentle learned the work of a corporate attorney in the early 2000s, he discovered he enjoyed collaborating with clients who were starting and building businesses, he says. Especially satisfying were the times he walked alongside a client as they navigated the peaks and valleys of a commercial enterprise and then stood beside them as they harvested the fruit of their labors.
“My favorite part of my job is to help a client be compensated fairly for what they created. That money often changes their lives and creates opportunities for their children.”
Owning a business is hard work, Gentle says, but helping smart, resourceful and resilient people achieve their goals is rewarding.
“When Ed McMahon gave (Publisher’s Clearinghouse) contest winners those giant checks, those people didn’t deserve that money, but Ed still made them happy. At times, we get to be like Ed, but it’s much more rewarding because our clients have worked hard to succeed.”
In addition to assisting clients, Gentle became involved with various civic endeavors, including co-founding the Chattanooga Technology Council. While serving on the assembly, he met Stephen Culp, a co-founder of Smart Furniture. Gentle later worked with the manufacturer and retailer as it raised its Series A venture capital financing.
After Gentle helped to close the deal, Culp asked him to join the company as an executive vice president. Gentle says leaving Miller & Martin and the practice of law in 2005 wasn’t easy, but he wanted to experience having a hand in running a business.
“I always felt like a bridesmaid and never the bride. I was developing as a young attorney and had the opportunity to work with great partners and mentors on interesting deals, but as each deal closed, I wondered what it would be like to stay involved with the business,” Gentle recalls.
“When working on acquisitions, we often become deeply immersed in a client’s business. For a limited period of time, it feels like you’re a part of it. Then the deal closes, and you must move on to the next one.”
Gentle spent a decade climbing the career ladder at Smart Furniture from EVP to president and then CEO. During that time, his work granted him insight he might never have acquired through the practice of law, he says.
“When I started at Smart Furniture, I had decent business instincts but no practical experience. Working in a venture-backed startup was baptism by fire, and I could make up for my lack of experience only with hard work.”
Fortunately, Gentle adds, he was among people who worked as hard as he did, and their collective efforts resulted in several years of consecutive triple digit sales growth for Smart Furniture.
A decade after joining Smart Furniture, Gentle returned to Miller & Martin and the practice of law to be able to spend more time with his family.
“Running a company is engaging but also exhausting. However, the law creates a predictable schedule, in some respects, and I don’t have to worry about making payroll.”
Gentle laughs but not without a hint of still-lingering relief. He also seems pleased he was able to return to the firm where he started to practice law.
“I had a good relationship with the attorneys at Miller & Martin, and my mentor, Hugh Sharber, would say, ‘You’re always welcome to come back.’ I thought about it and decided to return. I like working with businesses and clients, so it made sense.”
Since 2015, Gentle has applied the business acumen he acquired while working for Smart Furniture to a mergers and acquisitions market he says has had its ups and downs.
Until late last year, most of the deals that reached the letter of intent stage closed, whether a client was buying or selling, Gentle notes. However, late in 2022, the number of deals and the speed at which they proceeded to closing began to slow.
“The debt portion of deal financing started to become more difficult for many purchasers to secure. So, deals that would typically take three or four months to proceed from the letter of intent stage to closing were stalling or were no longer feasible.”
This continued through the first quarter of 2023, Gentle says. However, since April, the number of deals have started to pick up again. Even so, inflation continues to complicate corporate M&A work.
“The pandemic created shortages in the supply chain; these deficiencies caused prices to increase; and inflation prompted the Fed to increase interest rates, which impacted the M&A market.”
All that said, M&A legal work continues to be available due to the size and resiliency of the U.S. economy, Gentle ventures.
“We’ve seen a few clients become more creative in piecing together debt financing alternatives and have noticed some are selling off divisions of their businesses to preserve cash. And when they sell a division, there are often a good number of strategic buyers who are opportunistic.”
As Gentle discusses his practice, he doesn’t speak in a metered manner, or carefully measure his words before letting them loose; rather, he talks fluidly and with a warm and confident tone, as if his thoughts are well ahead of not only his tongue but also any question someone might ask.
While these musings can be engaging, people who stop there while conversing with Gentle will leave shortchanged, as a Google search reveals.
For example, Gentle’s firm profile on Miller & Martin’s website reports that he once sat next to actor Jennifer Lawrence on a flight across the country. Unfortunately, he didn’t realize his traveling companion was the Oscar Award winning actress until over an hour into the trip.
Digging a little deeper, football fans might uncover that Gentle played Blue Raider football alongside Kelly Holcomb, who went on to play 12 seasons in the NFL.
However, the best conversation starter in Gentle’s bio is his 2013 meeting with President Obama, who spoke with him about how a government shutdown was affecting small businesses. By that time, Gentle was CEO of Smart Furniture; his time bending the president’s ear came about through his role on an advisory council in Washington D.C. that consulted with senior White House officials on small business policy matters.
Gentle appearing on the radar of a U.S. president might not be as unlikely as it would seem, as he’s known for his business expertise and his willingness to share it with others. In addition to serving as a board member, adviser and mentor for several entrepreneurial companies in Chattanooga, for example, he’s also served on the board of directors for numerous community organizations.
Gentle also provides business mentoring at The Company Lab, a nonprofit that accelerates startups in Chattanooga.
Come fall, however, Gentle can be found in a football stadium or near a television watching a sport he loves.
His twin 20-year-old sons will be wearing Harvard crimson this fall, and his two younger sons, including Carson, who has committed to play for the University of Tennessee in 2024, are on the McCallie Blue Tornado roster.
With the bone-crunching action of the gridiron now decades behind him, Gentle prefers low impact activities such as golf, hiking and reading. A fan of science fiction, he’s currently tackling the “Expanse” novels, co-authored by Daniel Abraham and Ty Franck under the pen name of James S.A. Corey.
Gentle has yet to watch the “Expanse” television series, however, as his wife, Greta, a private tutor, is a worthy opponent when negotiating which shows they watch together. “We’re more of a ‘Yellowstone’ and ‘1883’ household,’” he says with poorly concealed resignation.
Gentle has nothing to hide when it comes to his enthusiasm for his practice, however. Whether he’s helping a startup to raise capital or in the trenches with a client during a merger or acquisition, he’s passionate about his work, he says, and is looking forward to lending his know-how to others for years to come.