Citigroup banker by day, hip-hop performer by night, Terence Bradford says, "Trust me, it's all the same hustle."
By Julia Boorstin

(FORTUNE Magazine) – IN AN UNDERGROUND hip-hop club on Manhattan's Bowery, a twentysomething crowd grooves to a heavy bass. The emcee introduces the next amateur rapper: "Give it up for Billy Shakes!" A compact 30-year-old in a baggy white T-shirt and oversized jeans takes the stage:

Your coke illegal ever' day of the year.

My Coke I buy legit at $20 a share.

You a gangsta? Then go get your paper.

I'm a paper gangsta getting stock quotes on my pager.

Stocks and drugs both the same in my eyes.

More buyers than the sellers cause the market to rise.

Audience members nod their heads in time to his punchy delivery. "Oh, yeah," says a girl in a Billy Shakes cap.

I know y'all out there really click-clackin' your guns. Hang wit' me I'll have you stik-stackin mutual funds.

Thousands on a whip [car] don't make you a star.

I'm buying options on the companies that makin' them cars.

Come on! Get stocks and bonds.

This is not a parody of Bentleys-and-bling raps that embrace conspicuous consumption. Billy Shakes is a sincere preacher of personal finance to a demographic he believes needs to hear his message. By day he is Terence Bradford, former stockbroker, now an area sales manager for Citi Mortgage. He travels around New York and Connecticut promoting mortgages and giving financial advice to salespeople for Primerica, a division of Citigroup that focuses on low- and middle-income families. The rest of his time he spends writing lyrics and hanging out at rap clubs, performing a couple of times a month. He recently spent $50,000 recording a demo called "Money Back Guaranteed."

"Trust me, it's all the same hustle. It's just that mine is legal," says Bradford as he steps out of his red Lexus onto Queens Boulevard. "Selling mortgages is very emotional. Just like in rap, we're trying to connect with people's hopes and dreams." He has taken out his diamond earrings and exchanged his rapper uniform for a banker's pinstripes and tiny wire-rimmed glasses. He strides into the Primerica office, stands before a folding table, and urges two dozen salespeople to sell more mortgages to improve their clients' lot and their own. "How many of you have a dream but have no plan to realize that dream? Put your hands in the air!"

In both his incarnations, Bradford aims to bring financial know-how to the 'hood he pulled himself out of. "I go back to the projects, and it's always the same. Kids want to dress like rappers, so they spend $300 on a pair of sneakers. People think they'll never have enough money for a house, so instead of saving and trying, they throw their money away."

Bradford was raised in the Bronx by a single mother who juggled jobs as a subway conductor and secretary, and who sent him to a judo club to keep him out of trouble. "There were drugs, violence, and gangs everywhere, and you had to get with a clique to survive," says Bradford. "Judo's discipline allowed me to stay focused on going to college." Bradford had talent; when he was 11, he won a silver medal at the Junior Olympics. In high school he did gymnastics, swimming, basketball, baseball, track, and football. In one football game he ran 95 yards for a touchdown, scoring an article in the New York Times and attracting college recruiters.

He picked Middlebury College in Vermont, where he played football (he never had another black teammate), majored in psychology and sociology, and rapped with friends, performing at open-mike nights. While classmates summered in Europe, Bradford worked as a toll collector at the Triborough Bridge and as a bank teller at Manufacturers Hanover Trust. When he graduated in 1996, he wanted a job on Wall Street, so he started cold-calling brokerages. He sweet-talked his way into an interview at the Boston Group (a stock brokerage that has since gone out of business) but forgot to bring his résumé. "I lied and said I didn't bring it on purpose so I could show what a great salesman I am," Bradford says. He got the job.

After a stint pushing stocks he took a break to try out for the New Orleans Saints, which turned him down. One phone call and ten interviews later, Smith Barney gave him a job as a broker working on commission. "Most people had clients from other careers or rich contacts. I had no rich uncle--I had nothing," Bradford says. He called names out of the phone book until he had 250 accounts with $5 million in assets.

In 2001, Smith Barney moved Bradford to Charlotte to do sales for its mutual fund division. "I didn't know anyone, so I hung out at the clubs and made friends with the deejays," he says. "Everyone in the clubs wanted to know about my job and about Wall Street." As his new friends barraged him with questions, he realized two things: Urban communities are desperate for financial advice, and his experience on Wall Street could differentiate his raps. He began writing lyrics about the similarities between the cutthroat worlds of the street and the Street: You're selling, products have to be worth their price, and clients have to trust you. "I'm not against flossing--buying bling, Bentleys, etc.--I just believe that in order to floss, you'd better have other assets, and you'd better keep your money straight." Bradford's raps won seven consecutive freestyle rap battles on Charlotte's Power98 station. "He can flow with the top dogs, but he's different because of what he raps about," says Power98 disc jockey Mr. Incognito. Bradford took his act back to New York in 2003 when he moved to Citi Mortgage; he's now a semifinalist for the Unsigned Hype Tour, a planned 26-city tour intended to showcase new talent for record labels and fans.

"I want the kids to know that if you don't have a jump shot and don't sell drugs, you can look at me as a role model," Bradford says. He raps about some of the same things other hip-hop performers do--women, his car--but it's his banker persona that sets him apart. He doesn't lecture; he doesn't consider himself a "social rapper." He hopes his lyrics about the cash on Wall Street will entice listeners onto for details on how to invest.

Lately he has been giving advice on a morning call-in radio show hosted by deejay Cipha Sounds on Shade 45, Eminem's channel on Sirius Satellite Radio. The segment begins and closes with a collage of Billy Shakes' lyrics and the tag line "Bringing Wall Street to your 'hood." One recent caller complained about the cost of maintaining his lifestyle --the monthly bill for his T-Mobile Sidekick topped $200. "If you can spend $1,200 on your pager, then you can save $2,000 this year. In 48 years, even if you get only 6%, that's 32 G's!" When another caller complained that his addiction to OxyContin was too expensive, Bradford didn't blink: "Get yourself off the drugs and then use that money to buy some drug stocks, like Johnson & Johnson."

Bradford isn't the only one using rap to promote fiscal responsibility. This summer he participated in the Get Your Money Right summit, sponsored by Russell Simmons's Hip-Hop Action Network, which featured a panel of performers talking about how they failed to manage their money and Suze Orman giving advice. "The No. 1 goal for the hip-hop life is to 'get some paper,' " says Benjamin Chavis, CEO of the Hip-Hop Action Network and former president of NAACP. "So we want to encourage young people to get money the right way." Orman says her fans have sent her raps they have written about her financial advice. Orman will broadcast a TV special on hip-hop and finance this fall, and she's launching a contest for raps about "how to be young, fabulous, and not broke," a play on the title of her recent book, Young, Fabulous, and Broke. "Russell and Billy Shakes are getting this generation more involved with their money," she says. "Hip-hop helps you sneak in through the back door to talk about finance, and now hip-hop has turned them on to my show."

With the king of hip-hop partnered with the queen of personal finance, it's clear that the two worlds are coming together. The question now is whether their message can counterbalance the profligate streak in mainstream hip-hop. Bradford cites a particularly nihilistic rap by The Big Tymers, called "Still Fly":

I can't pay my rent cuz my money spent,

But that's okay cuz I'm still fly ...

Got a quarter tank of gas in my new E class but that's okay cuz I'm still fly.

"That all-flash, no-cash mentality is awful," Bradford sighs. In both his day job and his rap performances, he advocates a longer-term point of view. And he hasn't forgotten about his own financial planning. "If I'm signed to a label, I'll become famous, which will spread my message and help people," he says. "And then I'll become rich."