The Coolest Black Family in America, No. 28: The Smiths

Meet the Smiths, Coolest Black Family no. 28!

Control, security, trust and working with loved ones are some of the key benefits the Smiths point to when discussing their family businesses, Rosa’s Greek Boutique and Transportation Unlimited. Nevertheless, when it came time for entrepreneurs Rosa F. Smith (59) and her 61-year-old husband Cary Smith to pass their down ventures to their 33-year-old daughter Chauntel two years ago, the family dynamic revealed its own set of challenges in the workplace.

“The transition year was very rough,” explains Chauntel, who is now CEO of both successful companies. Assuming a leadership position in her family’s business wasn’t easy, especially when her parents were resistant to change and reluctant to let go of the reins.

“It was essentially a battle between the young and old,” says Chauntel. She eventually gained her parents’ trust by presenting them with a persuasive ultimatum. “I showed them how I played a key role in the growth of the companies, and then it was pretty much like, ‘this is how we are going to do things from now on,’ ” recalls Chauntel. Her confident, strong approach is what convinced Rosa that her daughter could “handle hers.” 

“I’m glad she came to us that way,” says Rosa. “It showed me that she was willing to stand in the mud and do whatever she needed to get the job done. A part of me always knew it, but I had a hard time stepping back. I ran these businesses for so long that they were like my babies.”

Mrs. Smith gave birth to Rosa’s Greek Boutique after she attended a regional conference for her sorority (Alpha Kappa Alpha) in Pennsylvania. “They were saying’ ‘let’s go see the vendors,’ and I was like, ‘what are vendors?’ ” Vendors’ booths sold AKA paraphernalia, everything from umbrellas to coffee mugs. “I was amazed at how many women were lining up to buy items and how compulsive they were. These vendors were selling out. I knew right away this was something I should get into,” says Rosa.

She returned home to Dover, Delaware, convinced this was a no-fail business opportunity. She asked Cary if she could use their $1,000 tax refund check to launch their company. “I doubted the idea and thought she would make no money,” Cary admits. But when Rosa went to her first sales outing in Philadelphia with $700 worth of merchandise and returned home with $5,000, Cary was on board 101 percent.

The Coolest Black Family: The Smiths

The Coolest Black Family in America, No. 28: The Smiths

“She can come up with great ideas and make them happen. Everything she touches turns to gold,” Cary says now. ”I knew she always was very intelligent since back when we were dating.” 

It was 1971 when Cary first met Rosa in Dover. He was in his second year in the air force, and Rosa was a junior in high school. She and her girlfriends were driving to a club on the air force base where Cary was stationed when they stopped to ask him directions.

“He said he wanted to see the driver. I stepped out of the car and got back in. I think I gave him my number, so he could leave us alone. I thought he would never call,” reveals Rosa, who was interning that summer at the air force base chapel across the street from where Cary lived. “I was dating my high school sweetheart, and then we broke up.” 

 

“One person’s lost is another person’s gain,” says Cary. “She was very attractive and petite. We went out to lunch and one thing led to another.” The couple dated for two years before tying the knot. The wedding was held at Rosa’s parents’ home.

“We were so poor I couldn’t afford to rent a tuxedo for the wedding, so I wore my military service uniform with a white shirt and a bow tie,” Cary says. Rosa wore her white senior prom gown. “Never in my wildest dreams would I think we would be living so well [now],” says Rosa.

The journey to becoming successful business owners and financially independent wasn’t easy. Rosa, who worked as a computer science teacher and later a school administrator, juggled a full-time job (Rosa retired in 2008), raising Chauntel and running Rosa’s Greek Boutique while her husband was away stationed in the U.S. and abroad.

“It was very hard. I would work all week and travel to shows to sell my merchandise on the weekends. I always brought Chauntel with me and she would be sleeping under the table,” says Rosa. In 1991, Cary retired from the military and Rosa’s Greek Boutique became his priority too. Between 1991 and 2000, the company experienced tremendous growth and became a household name for Black Greek paraphernalia. Their customers include the Divine 9 Greek organizations and social organizations such as The Links Incorporated and Jack and Jill.

The tight-knit Smiths credit their personalized service for their success. “Cary’s networking skills are