Staff writer Cindy Rich can be reached at crich@washingtonian.com.
Kwame Jackson was at his desk at Goldman Sachs when his best friend, Dave Smith, e-mailed him about The Apprentice.
"Thanks," Jackson replied, "but I've got rich people to call."
Jackson liked working for the financial company, but things weren't going the way he'd hoped. It was March 2003–Jackson's third year into what he calls "the worst years in the equity market since the Great Depression."
Smith, who was working at JPMorgan, kept pushing. He thought a spot on a business-strategy show starring Donald Trump had to lead to something good.
"He made a decision with imperfect information," Jackson says. "That's what they teach you in business school."
Jackson didn't fill out the ten-page application. So Smith got a casting associate on the phone and told her about their credentials. He convinced her the network would want one of them. He thought he was too shy to do well, so he was rooting for Jackson.
Smith, Jackson, and the casting director soon were meeting in New York–about 215,000 people had applied–after the deadline had passed.
"We said, 'We know there's a one-black-guy rule in reality television,' " says Jackson. "He started laughing because he knew it was so true."
When Jackson asked for a leave of absence from Goldman Sachs to do The Apprentice, his senior managers told him clients wouldn't take him seriously. "They didn't see the vision," Jackson says. He quit.
Now Jackson, 30, is his own boss. In August, soon after 40 million viewers watched him on the Apprentice season finale, his real-estate development company landed a $3.8-billion deal in Prince George's County. The 500-acre property, called Rosewood, will include homes, offices, restaurants, and stores.
When Jackson took a spot on The Apprentice, he told producers he had his own agenda. They would use the cachet of his Harvard MBA to help market the show, and he would use them back. What he calls his "15-episode Kwame commercial" would be his platform to turn celebrity into capital.
During 61/2 weeks of filming in New York and New Jersey, other contestants argued and micromanaged. But even when mistakes by teammate Omarosa Manigault-Stallworth helped cost Jackson the job with Trump, he kept his cool.
"It's all about what you want to broadcast," he says. "I'm smarter than NBC. They didn't like that."
After the show, Jackson, Smith, and their friend Erik Moses formed Legacy Holdings, which includes Legacy Development Partners and Legacy Communications Group.
For Jackson, the company's name symbolizes "a lasting legacy of African-American entrepreneurism and wealth-building."
Jackson used to sell candy and bubblegum on the school bus in Charlotte, North Carolina.
"I turned $2 into $6, $6 into $12, $12 into $24," he says. He was ten.
He had moved there after spending his first eight years in Washington. His mother had gone to Howard University on a scholarship. Her own mother had answered phones and cleaned houses; her father couldn't read.
Jackson's parents divorced when he was a baby. His stepfather was a surgical resident at Howard, and his mother was the university's controller. They lived in DC's Woodley Park, moved to Silver Spring, then relocated to Charlotte. Jackson's father, who stayed in DC, saw him during holidays and vacations.
In high school, Jackson worked at McDonald's, where he supervised employees older than he was; the experience reinforced his desire to go to college. His mother died of cancer when he was 15. He took advanced-placement classes and put himself on the college track.
Jackson chose the University of North Carolina at Chapel Hill after his stepfather told him Howard cost $8,000 more and Jackson would have to cover the difference. He used money from his mother's life insurance to pay for college.
He became friends with Dave Smith through the Kappa Alpha Psi fraternity. After graduating in 1996, Jackson took a sales and marketing job with Procter & Gamble and bought a house in Charlotte, where Smith rented a room. Jackson hoped to own a company. Smith was interested in entertainment production.
Jackson left for Harvard in 1998 and joined Goldman Sachs in Manhattan after getting his MBA. Smith was just starting his MBA at Wharton. They looked forward to six-figure salaries on Wall Street.
"We both hit it at the wrong time," says Jackson. "We looked at each other like, 'What the hell is this?' "
Jackson left Goldman Sachs at 3 on a Friday in September 2003 and started taping The Apprentice that night. He went from living alone in an apartment to sharing what he calls an "Austin Powers-ish," 1970s-style Manhattan loft with shag carpet–and 15 people vying for the same job.
The cameras were never turned off. Phone calls were recorded. Jackson, who's six-foot-two, had trouble fitting in his bed. But he had more privacy than most: His roommate, who snored, was the first person Trump fired.
After each task–Jackson's assignments ranged from running a lemonade stand to organizing a Jessica Simpson concert–the candidates endured one- to two-hour boardroom meetings.
Jackson says the show's editing was accurate. The women were catty; the guys weren't. The men settled their problems quickly, despite the occasional temptation toward physical fighting.
"The people who complain gave garbage footage," says Jackson. "If you give garbage footage, they're going to make you look like garbage."
He laughs when he hears people say that Trump was behind the Rosewood deal. "People think he held a real-estate seminar," says Jackson, who hasn't talked to Trump since the finale. Outside of the boardroom, he and Trump had only a few short conversations.
Jackson never felt intimidated: "Everybody puts on their pants the same way I do."
At the end of October, Jackson knew he was one of the final two candidates, but Trump's decision would air live in April. If Jackson won, he'd run one of Trump's companies for a year; if he got fired, he'd start Legacy with Smith.
While he waited, Jackson worked as an associate casting director for the MTV reality show Room Raiders. (He had a connection.) He hosted lavish Apprentice viewing parties at clubs in New York. He couldn't tell anybody he was a finalist.
At a party a few hours after the season finale–Jackson lost–billionaire businessman Mark Cuban was waiting to greet the runner-up with a job offer. Jackson said he'd think about it. Soon he was getting about five offers a day. Senior managers at Goldman Sachs called to congratulate him.
Jackson stuck with his plan. "It's betting on yourself," he says. "It was never about 'How do I get to work for Mr. Trump?' I'm not trying to work for Trump–I'm trying to be Trump."
A few weeks later, fraternity brother Erik Moses approached Jackson about Rosewood. Moses, a lawyer who lives in DC, was working for AOL and had done some small-scale development. Jackson liked the idea of coming back to Washington and considered Prince George's "a hidden gem." He and Moses soon met with the Rosewood City Group, community leaders, and others to talk about their vision for Rosewood. About three months later, they had a deal.
Jackson divides his time between New York and Washington, where he usually stays with Moses. He likes to hang out on the Georgetown waterfront–a Sequoia restaurant employee offered to cover his $120 check in exchange for an autograph–and at Republic Gardens lounge on U Street.
Fans recognize Jackson wherever he goes. At the White House Correspondents' Association dinner in May, where he met Secretary of State Colin Powell, tennis star Serena Williams approached Jackson and told him she avoided playing on Thursday nights so she could watch the show.
Jackson spoke at a sixth-grade graduation in Harlem last summer and at the Howard business school in November. He's writing a book that will include lessons about breaking into corporate America.
Legacy is in negotiations with CNN to coproduce a business talk show hosted by Jackson, which his company hopes would be taped in Washington. The company is considering film and TV proposals, including one for a documentary about African-Americans elected to Congress during Reconstruction.
Legacy is also fundraising for Rosewood, which is named for an African-American community in Florida destroyed by fire during a terror spree in 1923. The groundbreaking is scheduled for 2006.
"These are all seat-at-the-table projects," Jackson says. Legacy, he adds, is "not about making our fortune now. It's about the monster we've created five years from now."
