JOHANNESBURG, South AfricaMonica Faith Stewart always identified herself as an African-American. But that was only until she moved to Africa.

When the former state legislator began promoting Illinois‘ trade interests in the continent’s southernmost country, she found herself in a place with a huge black majority. But South Africans, perhaps because they were beset by years of segregation, didn’t see her skin color, only her nationality.

“I had always referred to myself as African-American. But when I met people here, they said, ‘Oh, you’re an American,’” she said. “I had to come to Africa to feel like I’m an American.”

Ms. Stewart, an official observer in the 1994 election of former South African President Nelson Mandela, has been here for more than a decade. An energetic personality with a business bent, she now sells hair-care products throughout South Africa, hosts trade missions from Chicago and serves as a minister in a local church.

She came to South Africa along with a wave of black businesspeople and entrepreneurs following the country’s democratic transition in the mid-1990s. The 40-year apartheid era had officially ended with the election of Mr. Mandela, the longtime activist who had been imprisoned for 27 years for his efforts opposing the segregationist policy. He used his newfound power to peel back discrimination and reconcile the oppressed with their oppressors.

Before that, black people couldn’t vote, drive cars or own businesses. These more modern injustices were stacked on 400 years of bitter disenfranchisement at the hands of Dutch and English colonists who at various times warred over the land and the precious metals and minerals beneath it.

Talk to the thriving subculture of black Americans who now call Johannesburg home, and it’s obvious that they identify with the plight of black South Africans, but for most, moving here was more about opportunity than activism.

Brad Jackson, a New York native who grew up in Florida, is one of many American businesspeople in South Africa who have ties to Atlanta through enterprises, education or family.

He’s the president of the southern Africa alumni association for Morehouse College in Atlanta, where he got his bachelor’s degree in business administration. He followed that with a master’s in finance at Clark Atlanta University.

He moved to South Africa in 1998, following his father, who had been in the country for two years working for Vodacom SA, one of the country’s largest cellular phone service providers.

“In 1998, the opportunities in South Africa were astounding. It was all against the backdrop of Nelson Mandela’s new democratic society,” he said. “Being 26 years old, I felt an urge to leave the mundane, structured lifestyle of a corporate banker to seek a more fulfilling and adventurous life in Africa.”

Mr. Jackson bought five Subway sandwich franchises in the suburbs of Johannesburg and sold them after a few years to pursue property development and agribusiness interests. He has now settled on a consulting role with Global Reach Development, a 6-year-old firm that works primarily with government agencies and could soon start helping American companies enter the South African market.

A friend calls Mr. Jackson a “lost American,” but the 37-year-old seems to have found his place in Johannesburg. His South African wife, who also works with the consultancy, will give birth any day to their second child.

Still, to hear Mr. Jackson tell it, business in South Africa is a bit like working on one of the gold mines on which Johannesburg was built: The reward only comes after tough digging.

Aside from dealing with red tape from the government, which accounts for much of the spending in the country, Mr. Jackson said the entrepreneur faces many cultural challenges in South Africa. Polygamy is widespread, corruption is an issue and violent crime is an everyday reality. HIV/AIDs is a huge problem, with some organizations estimating that up to 40 percent of the population is infected. These facts can be off-putting for the uninitiated, and Mr. Jackson is still learning some cultural cues more than a decade into his journey.

“The way we grew up as Americans, they know nothing of it,” he told GlobalAtlanta. “I don’t always agree with the way they do things here, but we’re in their context now.”

Learning this context is Delwyn Ray‘s mission for the next four months. Mr. Ray is a graphic designer for Decatur-based Brown Town Marketing, which helps small and medium-sized companies craft their branding strategies and marketing materials.

Mr. Ray arrived in Johannesburg in March and is living in a local guest house run by another American until August. His visit will span the FIFA World Cup, which will draw thousands of soccer fans to the country beginning June 11.

He’s laying the groundwork for him and his girlfriend and business partner, Ly Eldridge, to kick-start their business in South Africa, fulfilling the pair’s long-held desire to live and work overseas.

“We’re taking it really slow and really trying to put our feet on the ground, make some headway, understand the culture of work and really see” what opportunities exist, Ms. Eldridge told GlobalAtlanta.

Mr. Ray has already made some connections, including a friendship with Courtney Priester, a Chicagoan who is a central connector in a tight-knit community of black Americans. Easy-going and quick to smile, Mr. Priester landed in South Africa by chance. A restauranteur back in Chicago, he followed his wife, Clara, who went to South Africa as a national marketing manager for McDonald’s Corp.

Sixteen years later, the Priesters see South Africa as home, though they maintain strong ties to the U.S. and to Georgia in particular. Mr. Priester’s parents and brother live in the Atlanta suburb of Powder Springs, and his business is tied to Atlanta. He sells the Isoplus brand of hairsprays, conditioners and relaxers imported from plants in Georgia and elsewhere in the U.S.

Mr. Priester is also president of the South Africa chapter of Democrats Abroad, a group that aims to boost absentee voter participation from expatriate members of the Democratic Party. The group has more than 500 members, and there are others who haven’t yet joined. His work in 2008 earned him a call from newly elected President Obama, despite the fact that Mr. Priester had campaigned against Mr. Obama while working on city and state elections back in Illinois.

Mr. Priester has kick-started a few enterprises in South Africa, including a creole restaurant and jazz bar he called Mzanzi Orleans. He shut it down after a three-year run when repeated late-night break-ins made the property more of a liability than an asset.

The experience didn’t sour him on owning a business.

“Entrepreneurship is instinctive,” he said, adding that he’s looking for ways to improve his current business. Most of his work is filling orders, but he’s itching to build a less reactive sales approach. Instead of chasing one-time buyers (South Africans are sensitive to the product of the moment and very loyal to brand-name items), he wants to educate the market and create a base of return customers who know the product’s real value.

Not all black entrepreneurs who came in the aftermath of apartheid’s collapse have met with success, said Kenneth Walker, who runs Lion House Communications, a Johannesburg firm that helps companies deal with crises and manage public relations campaigns. Many businesspeople—black, white and otherwise—came in thinking they could make a quick buck, introducing a particularly American brand of coarse arrogance at a time when South Africans were just beginning to shed an era of humiliation, Mr. Walker said.

Having lived under outsiders’ thumbs for so long, South Africans are particularly wary of such brashness, and those who show it are usually sent packing, said Mr. Walker, who hails from Washington and served as National Public Radio‘s chief correspondent in South Africa from 1999-2003.

“They came in with that ugly American attitude, that ‘I know what’s best for you,’” he said. “Who the hell wants to hear that?”

The keys to success in the country are to stay humble and work hard to earn the trust of your customers and acquaintances, Mr. Walker said.

“That’s how you do it anywhere,” he said.

As managing editor of Global Atlanta, Trevor has spent 15+ years reporting on Atlanta’s ties with the world. An avid traveler, he has undertaken trips to 30+ countries to uncover stories on the perils...