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Slightly diminutive at 5-foot-7, Brown talks big — dresses big too. It's the casual-Saturday ensemble of middle-age black men everywhere: pristine white slacks and a short-sleeved, button-up silk shirt, with a line of bulbous gold rings parked on his fingers.
He's tried his hand at just about everything that's caught his fancy. He's sold cars, and before that, ice cream. He worked as a deejay. He performed stand-up comedy, and took up with a local wrestling federation, first as a manager, a pimp character called Iceberg Cool, then as a bonafide wrestler.
At an early age, Brown and his siblings were indoctrinated into the family tradition of entrepreneurship. Brown's father, Roy, worked for Ford Motor Co. by day, and ran a janitorial service at night. Preston and his brothers were the crew.
"He was very fair about it," Brown recalls. "He'd negotiate the contracts, and he'd let us keep the money for whichever place we were assigned to."
At age 19, Brown announced to his parents that he was engaged. He'd graduated from Highland Springs High School in 1972, where he met Elsie, the woman who would become the first ex-wife. They were divorced within a year. Brown had lasted only four months at Norfolk State University before dropping out. He wasn't interested in books, only entertaining, recalls his older brother Otis.
That's not quite right, Brown says, clarifying: "I was interested in money, and most everyone I knew who had a degree was broke."
Then he announced that he was moving to Hollywood. It wasn't that much of a shock to his parents, Brown says. "If they saw an airplane going across the sky, and someone told them that I was flying it, they'd believe it because they knew that I'd try anything," he says. "I was just bold."
To be happy, Brown says he needed more than a house and his menial job moving around barrels of tobacco at a Philip Morris packing plant. But he says Elsie disagreed.
And so Brown departed via bus to Hollywood. He arrived four days later, significantly more broke than before he left Virginia. A stop-off at a casino in Las Vegas had drained his finances, leaving him with just $20 to navigate Los Angeles.
By the time he returned to Richmond, having tried and failed to break into acting, he was more determined than ever not just to live, but to make a fortune and "live big."
Thus began a long career of entrepreneurship, starting with an ice cream truck. Unlike some other operators, he drove into public housing projects after dark, when residents poured out into the courtyards to escape the heat. With the market cornered, Brown says he made a fortune.
Then there was the arcade he opened in the mid-1980s. But like before the money, which always seemed to flow downhill in his general direction, flowed back out just as quickly.
By 1993, at age 39, Brown was in debt and four times divorced. "It was a time when you couldn't say the word bankruptcy to people without them judging you," he says. But he filed for Chapter 11, and then during the course of 18 months began the slow trek back into financial solvency.
In the ensuing months, he decided to quit a job selling cars and strike out on his own. Driving through the South Side, he saw a for-sale sign in front of a small building near 32nd and Hull streets. In the wake of the bankruptcy, he found himself unwilling to work for anyone but himself. So he stopped and approached the owner, James Goodman, about buying the property to convert it into a car dealership of his own.
Brown says he eventually persuaded Goodman to let him have the property for a $500 down payment, having negotiated the price down from $10,000. "I'll pay you before I pay anyone else," he told Goodman, who accepted. "The little Dealer with the Big Heart" reads the copy of his very first newspaper ad. In it, he's pictured with glasses, his hair a mass of glistening Jheri curls. It appeared first in the Richmond Voice, Brown says, after publisher Jack Green extended him a line of credit.
While struggling to get the business started – in other words, scaring up enough capital to buy used cars to stock his lot — Brown slept on a sofa in the back room.
"People never realized that I was broke," he says. "Because I would always carry myself like I had a little something."
In the 18 years since, Brown has sold a few hundred cars — mostly to poor folks — extending thousands of dollars in credit, only to have customers renege and default. "I've seen it firsthand," he says. "The people that come to me, some of them don't have jobs, they're on welfare, they stop getting Social Security benefits, then they can't pay you back after you've agreed to finance them."
"It's a high-risk business," he says.
With the money he made, he was able to afford a lifestyle that allowed him to become partial owner of two community radio stations and open various restaurants, the latest of which is run by his fifth wife, Judy. They have a blended family, with six children between them, four from Brown's previous marriages.
But the dealership's business model wasn't recession-proof. In 2009 Brown filed for Chapter 13 bankruptcy to reorganize some $1.4 million in personal debts. "When the economy hit everybody, it hit poor people too," he says. "Poor people are my clients."
Brown says that when the economy tanked, 102 of his customers declared bankruptcy. Brown financed most of his clients using his money. So when his customers defaulted, so did he. His bankruptcy reorganization since has been dismissed, so he's stuck paying down the personal debt on his own.
Like so many candidates for political office, Brown says he was called to run. "I wasn't interested in being no senator," he says. But he'd spent years prior toying with the idea of running for political office.
In 2004 he was among a pack of local politicians vying for the chance to challenge Reva Trammell for the 8th District seat on City Council. That honor eventually went to Jackie Jackson, and Brown never made it onto the ballot.
Political life still beckoned, while he began sprinkling in political commentary with the soul and gospel tunes on his weekly radio show. Ultimately, though, it was his wife, Judy, who convinced him to act. She said, "You're just one person," he recalls. In order for people to really listen, she advised, he needed to run.