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.

“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 unbelievable. He is very personable and can remember everyone’s name from even 30 years ago! The women at the events love him,” Rosa points out. “Once you get to know your customers, they become like extended members of your own family. When we started, we served the grandmother, then the daughter and now Chauntel is serving their grandchildren,” explains Cary.

Rosa’s Greek Boutique is the third oldest vendor in America. “It’s important for us to be minority family business owners. I don’t know many like us. We worked very hard and put so much time and effort to keep this in the family,” says Rosa. Through Rosa’s Greek Boutique, the Smiths encourage young Black women to get involved in businesses with a special scholarship fund.

Chauntel was only a 3-year-old when Rosa’s Greek Boutique launched. Growing up exposed to the business, she naturally got involved starting as a little girl helping her parents pack goods, sell merchandise at events and fetch lunch. Despite being immersed in the family business from day one, Chauntel never thought she’d choose it as her career. Instead she followed another one of her mother’s footsteps and went down the educational path.

“I got a B.A. in elementary and special ed, and my masters in curriculum and instructional. I taught kindergarten for eight years,” says Chauntel, who is (naturally) also an AKA. It was the birth of her son that inspired Chauntel to join the family business. “I got married and I had my son, and I wanted more flexibility as a mom. The opportunity arose to work in the company full-time, so I took it.” In 2006, the Smiths launched Transportation Unlimited, a private transportation company that transports homeless and displaced students to and from school every day.

In addition to the stress of taking over as CEO of both companies, Chauntel was in the midst of a divorce. She was married for six years, and shares that her ex-husband wasn’t supportive of her success. He wanted her to take over the company entirely and kick her parents out. “That was out of the question,” says Chauntel. She put all her energy during this rough patch into managing the companies.

“The divorce made me who I am today in my personal life and in my business life. I believe I can overcome any obstacles,” she says. While Chauntel takes the lead, her parents are still actively involved in the company today, playing a supporting role. “Eighty-five percent of what I know about running a business is what I picked up watching my parents do it,” explains Chauntel.

Similar to her parents, Chauntel has had to work long days and nights in the name of the businesses. “An entrepreneur will put in a 60-hour week to not have a job where you put in a 40-hour week. You give up a good portion of your life to run your own business,” says Chauntel.

As for her 6-year-old, Xavier, Chauntel wants him to decide whether he wants to continue this legacy. “I don’t want him to feel like he has to do it.” She tries her best not to let her busy work schedule keep her from spending quality time with him. Finding that balance between work and motherhood can be very challenging. She passed up on a profitable show last week to attend her son’s T-ball game. “I’m not gonna keep him from his activities because I have to work. I want him to have a normal life,” says Chauntel, “It may seem impossible sometimes, but it’s important to us as a family to work at it. My parents did it and now it’s my turn.”

Alexandra Phanor-Faury is a Haitian-American writer living in Brooklyn, New York with a slight (OK, major) addiction to fashion and pop culture. When she’s not up in the middle of the night filling her online shopping carts and catching up on style blogs, she’s writing about fashion and entertainment for a number of websites and her blog, Fringueuse.