Distinctively Southern Gentlemen
- YOUR Williamson
- 2 days ago
- 13 min read
By Webster’s standards – a gentleman is broadly defined as a chivalrous, courteous or honorable man. The term's meaning has evolved over time, ranging from a historical social class of the landed gentry to a modern descriptor for someone who exhibits high standards of propriety, kindness and good manners. That being said, it isn’t hard to find such a distinguished man in our midst here in Williamson County. In both business and personal life, our 2026 Distinctively Southern Gentlemen, fulfill all of those characteristics and more in their everyday. You know them from their well-known local businesses, but perhaps you didn’t know much about the men behind the business. Well, let’s learn a bit more, shall we, about just what it means to be a southern gentleman here in our community.
Special thanks to our Gentleman Clothiers who dressed our fellas for their photos featured in this issue:
Franklin Road Apparel Company
508 West Main, Suite B
Franklin, TN 37064
Oak Hall
4020 Aspen Grove Drive, Suite 130
Franklin, TN 37067
Carmine Grassi
Ford Lincoln of Franklin
For nearly four decades, Carmine Grassi has built his life and career around a simple philosophy: treat people the right way, work harder than anyone else and never stop learning.
As the owner of Ford Lincoln of Franklin and Infiniti of Cool Springs, Carmine has become known throughout Williamson County for his passion for leadership and his commitment to building exceptional teams. While the automotive business has given him incredible opportunities, he believes his greatest accomplishment isn’t measured by awards or sales – it’s helping others discover their potential. Watching employees build successful careers, provide for their families and accomplish goals they never thought possible is what continues to inspire him every day.
After leaving school in the tenth grade, Carmine entered the automotive business with determination, a willingness to learn and an unwavering work ethic. Those experiences shaped the leader he is today and instilled in him a deep appreciation for perseverance, humility and personal responsibility. His journey is proof that where you begin in life never has to determine where you finish.
Outside the dealership, Carmine values family above all else. He treasures time spent with his daughters, grandchildren, family and the people closest to him. Whether supporting local charities, mentoring young professionals or simply enjoying all that Williamson County has to offer, he believes success carries a responsibility to give back.
For Carmine, leadership is about much more than running a business. It’s about setting an example, earning trust and treating every person with dignity and respect. He believes reputation is built one decision at a time and that character is revealed by what you do when no one is watching.
For Carmine, success has never been about what he achieves for himself, but about the lives he helps improve along the way.
OUTFIT DETAILS:
Oak Hall
Tie
Ferragmo
Pocket Square
Brackish
Cufflinks
Brackish
Jeremy Scates
111 Motorcars
What began as a vision has evolved into one of the most unique automotive experiences in the country. From the outset, Jeremy believed that everyone –- especially car enthusiasts – deserved more than a traditional car dealership experience. His goal was to create a true concierge-level automotive destination, one that could serve every type of automobile, whether it was a reliable daily driver, a prized collection, a family heirloom or even a world-class exotic.
Today, that vision is fully realized through an Automotive Resort that is now home to both 111 Motorcars and the 111 Motorclub.
At its core, 111 Motorcars offers a carefully curated sales experience built around transparency, expertise and personalized service. Every client receives the same level of attention and care, regardless of the vehicle they are buying or selling. It is a commitment that guides every interaction and has helped establish lasting relationships with clients across the country.
That commitment extends across the six-acre campus, offering a solution for everything your garage could ever need or want. Whether it is routine service, performance upgrades or specialized attention for high-end automobiles, clients know their vehicles are being cared for by people who genuinely understand and appreciate them.
For collectors and enthusiasts seeking peace of mind, 111 also offers premium vehicle storage and collection management. Designed to protect and preserve an automobile's highest value, the storage program provides owners with a secure, custom-tailored environment, ensuring their vehicles remain polished, charged and ready to enjoy at a moment's notice.
Perhaps the most powerful expression of Jeremy's original vision is the 111 Motorclub. Created to bring people together through a shared passion for cars, the club has become a thriving community where members can connect, attend exclusive events, enjoy unique experiences and build lasting relationships. The experience is further elevated by a beautifully designed private clubhouse featuring a full-service bar and dedicated event space.
Together, sales, service, storage, events and the Motorclub create something far greater than any one business. They form a complete automotive ecosystem built around the enthusiast, but for the benefit of every family and every car we serve. What started as Jeremy's vision of a concierge-level experience has become a reality – one that continues to redefine automotive ownership at every level while establishing itself as a national destination for the automotive community.
OUTFIT DETAILS:
Franklin Road Apparel
Quay Cuban Collar Shirt
Peregrine’s
Vigo Trouser in White
Closed
Creator Evo Sneaker in Blue
LAVAIR
Alan Looney
Castle Homes
For more than three decades, Alan Looney has built a reputation as one of Middle Tennessee’s most respected design build firms. As President of Castle Homes, Alan has dedicated his career to creating homes that are as enduring as the relationships he and his Castle team builds with clients, trade partners and the community.
Founded in 1993, Castle Homes has become synonymous with luxury custom homebuilding throughout Nashville, Brentwood, Franklin and Williamson County. Known for exceptional craftsmanship, thoughtful design and an unwavering commitment to quality, Castle Homes approaches each project with the belief that a home should be more than a place to live. It should be a family heirloom.
What truly sets Castle Homes apart is its client-focused design build process and commitment to transparency. Alan and his team carefully guide homeowners through every phase of the journey –from vision and design to budgeting and construction. A hallmark of the Castle Homes experience is its guaranteed pricing model, which provides clients with a detailed, fixed project price before construction even begins. In an industry often marked by uncertainty, this approach offers peace of mind and reinforces the trust that has become the foundation of the company’s reputation.
That commitment to integrity, service and craftsmanship has earned Castle Homes numerous industry accolades and the loyalty of generations of homeowners.
While Alan’s professional accomplishments are significant, those who know him best often speak first about his character. He leads with integrity and believes success is measured not only by what you build, but by how well you treat people. Guided by the philosophy of continuous growth, Alan invests in his team by encouraging ongoing learning, professional development and the pursuit of excellence. His leadership style reflects traditional Southern values–humility, kindness, hard work and a desire to serve others.
Beyond the homes he builds, Alan is deeply invested in the Middle Tennessee community. Through charitable involvement, mentorship and support of local organizations, he continually seeks opportunities to give back. Whether meeting with a prospective client, mentoring a young professional or greeting a trade partner on a jobsite, Alan approaches every interaction with authenticity and grace.
For Alan Looney, being a Southern Gentleman is not about recognition or titles. It is about honoring your word, treating people fairly and leaving every person and every place better than you found it. Those principles have guided his life, his business and the lasting legacy he continues to build through Castle Homes.
OUTFIT DETAILS:
Oak Hall
Sport Coat
Canali
Shirt
Eton
Alligator Belt
L.E.N.
Jeans
Teleria
Shoes
Peter Huber
Tom Sullivan
Covey Rise Properties
Tom Sullivan spent most of his career in the corporate world before pivoting to land and farm sales in 2019 with Mossy Oak Properties. He suffered a failed business setback and a non-compete clause that forced him to start a whole new career in his mid-forties. Tom always says, “You fail your way to success.” He knew that if anyone could lose so much financially and go into a straight-commission career, it would be him. Tom had his wife Kate and two kids, Huck and Savannah, to support, so failure wasn’t an option. He earned Agent of the Year for highest sales volume in both 2020 and 2021.
In January 2022, Tom founded Covey Rise Properties, a boutique firm specializing in land, farms and estates across Tennessee. Covey Rise quickly became a premier marketer of high-end and unique properties, setting the brokerage apart with immersive lifestyle videos from its Short Film series and magazine-quality photography.
Some of Covey Rise's shoots are three full days of sunrise-to-dark footage, shot with three different camera operators shooting simultaneously, to create a four-minute video. His clients trust him to sell an asset ranging from five million dollars to a current listing of thirty-five million dollars. They have one chance to maximize their profit on that asset, so they deserve the best possible marketing and salesmanship. It baffles him to see cell phone photos of a multi-million-dollar property.
Tom’s corporate background instilled in him an understanding and a commitment to be a good steward of both the land and his clients’ money. After losing so much, he always looks at the exit strategy first for his clients. It may be their forever place, but they may, or someone in their family, may sell it someday. Property with acreage, especially here in Williamson County, is arguably one of the safest investments one can make. Tom tells people that he can’t promise them a double, a triple or a home run, but he can unequivocally say you won’t lose.
Tom’s job security comes from selling a finite resource. Mark Twain said it best: “Buy land, they’re not making it anymore.” He says to people, “We could be meeting right now in your 20,000-square-foot mansion, and that’s great, but this house can be built in any state in America.” You can’t reproduce land.
Tom has been fortunate to list some of the most beautiful properties in the Southeast, which has translated to over $375 million in sales. He currently has 115 million dollars in active listings and about fifty million dollars in off-market. Finding those off-market properties is something that he has become skilled at. In 2025 alone, he did thirty-two million dollars in off-market transactions.
Tom is very proud to have grown Covey Rise Properties into what it is today.
OUTFIT DETAILS:
Franklin Road Apparel
Hammer Straight Denim in Brown
Kato
Deon Check Shirt
No Nationality
Native Ankle Boot in Tan
ROAN
Matt Watson
Cocktail Carriage
Cocktail Carriage specializes in crafting bespoke mobile bar experiences. They're a fully mobile cocktail service dedicated to elevating your parties and events with craft cocktails and genuine hospitality. Cocktail Carriage offers full event customization, tailoring every detail of their beverage service to your unique vision and theme. They bring the craft cocktail experience directly to you! Forget the stress of stocking your bar for a party or hiring individual bartenders; they handle every detail, allowing you to relax and enjoy your celebration.
Cocktail Carriage operates on a premium “dry hire” model, meticulously designed to provide their clients with maximum flexibility, control and a detailed beverage experience for their events. A ‘dry hire’ model separates alcohol procurement from bartending services. This approach empowers you, the host, to have complete control over your budget and brand selection. They will consult and recommend options for you to purchase the spirits, wine and beer directly from local providers. They take care of absolutely everything else required to deliver a full-service, luxury bar experience.
Founded by Matt Watson, Cocktail Carriage is the culmination of years of dedicated service within the hospitality industry. After nearly a decade of honing his craft in fast-paced environments, Matt recognized a growing need for a more personalized, premium approach to event beverage service. He stepped away from the traditional restaurant scene to build something unique: a service that brings genuine hospitality and craft cocktails directly to you.
This cultivated passion was built through key leadership roles within the cocktail industry. Matt served as the General Manager of an esteemed cocktail lounge in Cleveland, and after moving to Nashville, he sharpened his management skills as a beverage manager at a 325-acre luxury, farm-centric resort and wellness destination in Franklin, Tennessee. Matt's experience in these demanding environments allowed him to refine his craft and deepen his commitment to exceptional service.
Matt, using his expertise, founded Cocktail Carriage with a clear vision: to deliver a premier mobile bartending service. He believes that a meticulously crafted cocktail, paired with genuine hospitality, serves as a catalyst for connection and creates truly memorable occasions. His commitment is to provide a fully customizable and sophisticated beverage experience, ensuring an unforgettable event for the clients and their guests.
OUTFIT DETAILS:
Franklin Road Apparel
Wrench Dobby Stripe Shirt
Kato
Hammer Straight Selvedge Denim
Kato
Chelsea Boot in Copper
Red Wing
Zane Martin
Renasant Bank
With a history dating back to 1904, Renasant Bank has built its reputation on a tradition of relationship banking, community involvement and local decision-making. Founded in Tupelo, Mississippi as The Peoples Bank & Trust Company, the institution has grown from a small community bank into one of the Southeast’s leading regional financial organizations. Throughout more than a century of service, Renasant has remained committed to helping individuals, businesses and communities prosper while maintaining the personal approach that has defined the bank since its earliest days. Today, with operations across multiple Southeastern states, Renasant continues to honor its heritage by investing in the communities it serves and fostering long-term relationships with its clients.
That commitment to community and relationship-driven banking is reflected in the leadership of bankers like Zane Martin. A native of Arrington, Tennessee, Zane grew up in Williamson County and graduated from Page High School. He went on to earn his bachelor’s degree from the University of Mississippi before completing his M.B.A. at Middle Tennessee State University. With more than twenty years of banking experience, Zane currently serves as Senior Vice President and Commercial Relationship Manager at Renasant Bank’s Downtown Franklin office on Columbia Avenue.
Throughout his career, Zane has focused on helping businesses achieve their financial goals while building trusted, long-term partnerships. His approach aligns closely with Renasant’s longstanding philosophy that successful banking begins with understanding the unique needs of each client and community.
Beyond his professional accomplishments, Zane has demonstrated a deep commitment to civic leadership and community service throughout Williamson County. He has served as Past President of the Franklin Noon Rotary Club, Past Vice President of the Next Gen Heritage Foundation and a Past Board Member of Franklin Tomorrow, Friends of Franklin Parks, My Friend’s House, Friends of Williamson County Animal Center and several other community organizations. He is also a proud graduate of the sixteenth Class of Leadership Franklin.
Zane’s dedication to service, leadership and community engagement reflects the values that have guided Renasant Bank for more than 120 years. By combining local roots, professional expertise, and a passion for strengthening the community, he continues the tradition of relationship banking that has made Renasant a trusted financial partner throughout the Southeast.
OUTFIT DETAILS:
Oak Hall
Gray/Blue Check Sport Coat
Castangia
Sky Blue Dress Shirt
David Donahue
Surge Performance Trouser
Peter Millar
Bit Loafer
Ferragmo
Belt
Torino
Hem Stitch Linen Pocket Square
Sheridan
Zach Reeser
Cool Springs Upholstery
Cool Springs Upholstery has been part of Middle Tennessee for thirty-three years. What started as a small family shop founded by Zach Reeser's grandparents – who moved south from a farm in Central Illinois with a set of values that still defines the business today – has grown into one of the region's most capable upholstery operations, serving residential clients, interior designers, commercial spaces and some of Nashville's most recognizable venues.
Zach grew up in that shop. As a kid, he answered the phones. As a teenager, he rode along on deliveries with his grandfather. Even after graduating from Franklin High School, attending the University of Tennessee, and building a fourteen-year corporate career – more than a decade in management, six years in executive sales, marketing and leadership roles – he kept finding his way back to the shop whenever he was in town. Three years ago, he came back for good.
He came back to carry the torch of a business he'd grown up around, to give his family more of his time, and to apply what he'd learned across fifteen years of corporate leadership to a small business doing meaningful work in an age when so much furniture is built to be replaced rather than restored. "Furniture creates the spaces that hold the memories of our lives," Zach says. "We get to help people make those memories - and keep them."
Today, Zach co-owns Cool Springs with his aunt Amy Reeser Freese and uncle Jeff Reeser, who shepherded the company through years of growth before he joined. Zach serves as CEO – driving the company's vision and growth - while Jeff leads the commercial side. Together with their team, they've modernized and systematized a thirty-three-year-old craft business so it can do more of what it has always done well - for more people. The shop handles custom residential upholstery and designer collaborations, full commercial fit-outs, custom-built furniture, fine repairs, cushions, pillows and draperies. From a single heirloom dining chair to an entire restaurant's seating, it takes the work on at scale and at standard.
Most Williamson County residents have probably sat on a piece Cool Springs has done without ever knowing it – at a favorite restaurant, a downtown venue, a corporate office or a friend's home. Being a quiet part of those moments is, for Zach, one of the best parts of the job.
Outside the shop, Zach coaches little league, leads at his church, and founded DadCard – a membership for the men who show up, built to connect the dads of Nashville with each other and with the local businesses around them. Whether it's a piece of furniture, a team of kids or a family counting on him at home, the philosophy is the same: do the work, do it right and show up for the people depending on you.
OUTFIT DETAILS:
Oak Hall
Blazer
Castangia
Five Pocket Pants
AG
Knit Polo
Bugatchi
Suede Sneaker
Bugatchi
Johnny Weber
The Weber Bros. Hospitality
Raised in Anadarko, Oklahoma, Johnny Weber learned the value of hard work, hospitality and treating people right from an early age. Inspired by the example set by his parents, he developed a passion for serving others and creating places where people feel welcome – values that continue to shape every business he owns today.
An entrepreneur, investor and hospitality-driven business leader, Johnny has built a growing portfolio of businesses across the Southeast through Weber Bros., creating brands that bring people together, create opportunities and leave a lasting impact on the communities they serve.
Johnny's entrepreneurial journey began in 2008 with Sport Clips Haircuts, where he grew from a single franchise owner to developing more than 180 locations across multiple states. That experience laid the foundation for Weber Bros. and established the people-first leadership philosophy that continues to guide his business ventures today.
While his portfolio spans multiple industries, Johnny's true passion lies in hospitality and preserving places with character, history and a strong connection to their communities. His brands include The Country Boy in Leiper's Fork, a beloved Tennessee landmark established in 1968, and The Tornado Room, a swanky speakeasy tucked beneath the historic restaurant that blends vintage charm, craft cocktails and a one-of-a-kind guest experience. He is also the owner of Hogwood BBQ, an Oklahoma-inspired barbecue restaurant built around authentic smokehouse traditions, bold flavors and genuine hospitality.
At Zolo's Italian Restaurant, the focus is simple: exceptional service, incredible red sauce and the kind of Italian dining experience that keeps families coming back for generations. Franklin Juice Café reflects Johnny's commitment to health and wellness, offering fresh, nourishing options designed to help guests live healthier lives. His portfolio also includes Davis General, a restored 1928 gas station turned gathering place, and Gray's on Main, one of Franklin's most iconic historic destinations.
Johnny's entrepreneurial vision also extends beyond Tennessee through ventures such as Red Phone Booth in Miami, Prime IV Hydration & Wellness and the expansion of 7 Brew Coffee throughout Georgia.
Today, Johnny works alongside his father, Eugene and his sons, Cole and Tanner, continuing a family legacy built on hospitality, hard work and service. His vision extends beyond business success – it's about preserving meaningful places, developing great people and creating experiences that bring communities together for generations to come.
OUTFIT DETAILS:
Franklin Road Apparel
Knitted Polo
Les Deux
Linen Trouser in Deep Truffle
No Nationality
Venetian Slip-On in Steel
John Varvatos
