Sign of the Times (And Tequila!)

When Andrea Chaires took charge of the Rosepepper Cantina, following the death of her father in 2014, it was not an easy transition. “I spent the first two years just being terrified,” she says. “I walked into a place and was the boss of 50 employees, having never served a table in my life. I didn’t know anybody’s name or what was on the menu.”

Despite lacking experience, Chaires did have a deep family connection to the restaurant business. Her grandfather, Vincente Chaires, was a partner in El Taco, Nashville’s first Mexican fast-food restaurant chain. In 1970, he went solo with Es Fernandos, at the corner of Gallatin Pike and Haysboro Avenue in Inglewood, personally overseeing the beloved neighborhood taqueria until his son, Ernie Chaires, purchased it in 1994.

“My dad was relentlessly ambitious,” Andrea Chaires says. “He learned the restaurant business from my grandfather and then moved our family to Los Angeles to become the operations manager of a Taco Bell franchise. When he bought Es Fernandos, we stayed in California and he moved back to Nashville. He had an apartment in the attic of Es Fernandos with a tub and sink, but no toilet, so he had to go downstairs to use the restaurant bathroom. He would commute between Nashville and L.A. every few weeks. We would visit him here occasionally, so my parents stayed happily married and he was always super present in our lives.

In 2001, Ernie Chaires opened his dream restaurant, the Rosepepper Cantina, in the former Joe’s Diner building that was severely damaged by the 1998 tornado. Even though most of the structural damage had been repaired, Chaires threw himself into reshaping the location to fit his long-held personal culinary vision. The Rosepepper quickly became an anchor business in the revitalization and transformation of the East Side dining scene.

“My mother was in real estate in California,” Andrea Chaires says. “Dad financed the Rosepepper with his credit cards and some money he borrowed from my mom’s business partner — that was it. My mom always had faith. She’d say, ‘Whatever your father’s doing, I’m sure it’s going to work out.’”

Ernie Chaires personally managed Rosepepper, along with Es Fernandos, until its closure in 2007. Around the same time, he launched the popular neighborhood watering hole and music venue Foobar (now Cobra), which he sold in 2012.

Even a 2010 fight with lymphoma failed to deter Chaires’ ambitions, but when the cancer returned in February 2014, it proved to be his last battle. Ernie Chaires passed away on March 23, 2014, at the age of 62.

That’s when Andrea Chaires left her career as an in-house attorney for a Los Angeles marketing firm to become the guardian of her family’s business and her father’s dream.

“I’ve always been super independent, and without a doubt the most like my father — definitely ambitious and driven,” she says. “We butted heads like nobody’s business, but when he got sick the second time, that changed. I was sitting with him at the hospital one night, and he looked at me and said, ‘If this doesn’t work out, you’ve got to promise me you’re going to take care of the family and the business.’ I said, ‘Yeah, I got it. I’ll figure it out.’”

Moving to Nashville, Chaires leapt into her father’s business. Taking shifts as a food runner, hostess, waitress, and bartender, in addition to managing the finances, she learned every aspect of the restaurant business from the ground up. While the learning curve was steep and sometimes overwhelming, she soon discovered a way to utilize her wit, creativity, and marketing experience.

“When our social media manager had her second child and needed more time to herself, I took over some of the social media channels,” Chaires says. “That’s when I asked where the letters for the sign were kept. Someone brought me a dusty old box of letters and I thought, ‘This, I can do.’”

In short order, the Rosepepper’s front marquee made the jump from drink specials and holiday wishes to an ever-changing parade of quips and topical humor. “I didn’t text you, tequila texted you.” “Tequila — because election 2016.” “We love margaritas as much as Kanye loves Kanye.”

“I started cracking jokes on the sign and it resonated really quickly,” Chaires says. “We went from 1,500 Instagram followers, to 5,000, then 10,000, and now we’re over 30,000. It was just me on that ladder, between food running and hosting, putting up jokes as I thought of them. It was a way to escape from being terrified all the time.”

Chaires’ witticisms gained extra traction online when native Nashvillian and Oscar-winning actress Reese Witherspoon shared a photo of the sign, leading to shares and comments from other celebrities, including LeBron James, Octavia Spencer, and Halle Barry. Four years after Chaires took command of that box of dusty letters, Rosepepper’s sign has spread around the world, been emblazoned on T-shirts, and transformed a favorite neighborhood restaurant into a destination for visitors to the Music City.

“You never can tell for sure if the sign directly increases business,” Chaires says. “But the first time the sign went viral, within one to two days we saw a spike in business. And that’s continued every time someone with a million followers or more shares it, without fail.”

In addition to increasing sales, Chaires implemented small improvements to the restaurant — adding more lights to the back parking lot, enlarging the restrooms, and improving the kitchen. She’s also overcome a large portion of her initial fear, while keeping her father’s dream alive and thriving.

“I’m not trying to reinvent the wheel,” Chaires says. “My dad invented the wheel here, and it works, and it’s great. I’m in business to take care of my family and keep my promise to my father, and this is the most important work I’ve ever done. I take a lot of pride in that, but the sign is the fun part for me. The sign is just me, out of the shadow of my father. I love my dad, and I love this business, but it’s really nice to have a part of it that’s just me.”

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