Chris Gardner tells 20/20 how he worked to move himself from a life of homelessness to a successful life as a businessman.

　　Gardner is the head of his own brokerage firm and lives in a Chicago Townhouse--one of his three homes with a collection of tailored suits, designer shoes, and Miles Davis albums.

　　His path to this extraordinary success took a series of extraordinary turns. Just 20 years ago, Gardner was homeless and living, on occasion, in a bathroom at a Bay Area Rapid Transit station in Oakland, Calif.

　　Gardner was raised by his mother, a schoolteacher. He says he never knew his father while he was growing up. But his mother had a way of keeping him grounded when he dreamed of things like being a jazz trumpeter.

　　Mothers have a way of saying things, Gardner said, She explained to me, Son, theres only one Miles Davis and he got that job. So you have to do something else. But what that something else was, I did not know.

　　Gardner credits his uncles with providing the male influence he needed. Many of them were military veterans. So, straight out of high school, he enlisted in the Navy for four years. He says it gave him a sense of what was possible.

　　A Red Ferrari and a Turning Point

　　After the military, Gardner took a job as a medical supply salesman. Then, he says, he reached another turning point in his life. In a parking lot, he met a man driving a red Ferrari. He was looking for a parking space. And I said, You can have mine. But I gotta ask you two questions. The two questions were: What do you do? And how do you do that? Turns out this guy was a stockbroker and he was making $80,000 a month.

　　Gardner began knocking on doors, applying for training programs at brokerages, even though it meant he would have to live on next to nothing while he learned. When he finally was accepted into a program, he left his job in medical sales. But his plans collapsed as suddenly as they had materialized. The man who offered him the training slot was fired, and Gardner had no job to go back to.

　　Things got worse. He was hauled off to jail for $1,200 in parking violations that he couldnt pay. His wife left him. Then she asked him to care for their young son without her. Despite his lack of resources, Gardner said, I made up my mind as a young kid that when I had children, my children were gonna know who their father was. Although a broker finally helped him enter a training program, Gardner wound up with no place to live. He was collecting a meager stipend as a brokerage trainee, and, like many working poor in America, he had a job but couldnt make ends meet.

　　The Kindness of Strangers

　　When he could afford it, he stayed with his son, Chris Jr., in cheap motels. When they returned home at night, Gardner says, he received help from some unexpected sources. The ladies of the evening were beginning their shift. And they would always see myself, this baby and the stroller.

　　So they started giving him $5 bills. Without their help, Gardner said, there would have been nights when he couldnt have fed his son. The Rev. Cecil Williams, founder of Glide Memorial Church in San Francisco, remembers the first time he saw Gardner, who had gone to the church with his son to stand in a meal line. He said, I wondered, What in the world is a man doing with a baby?

　　Even to Williams, it was an unusual sight. The Urban Institute estimates that children make up 25 percent of the nations homeless population, but most are living with a single mother,not the father.

　　Chris Gardner tells 20/20 how he worked to move himself from a life of homelessness to a successful life as a businessman.

　　Gardner is the head of his own brokerage firm and lives in a Chicago Townhouse--one of his three homes with a collection of tailored suits, designer shoes, and Miles Davis albums.

　　His path to this extraordinary success took a series of extraordinary turns. Just 20 years ago, Gardner was homeless and living, on occasion, in a bathroom at a Bay Area Rapid Transit station in Oakland, Calif.

　　Gardner was raised by his mother, a schoolteacher. He says he never knew his father while he was growing up. But his mother had a way of keeping him grounded when he dreamed of things like being a jazz trumpeter.

　　Mothers have a way of saying things, Gardner said, She explained to me, Son, theres only one Miles Davis and he got that job. So you have to do something else. But what that something else was, I did not know.

　　Gardner credits his uncles with providing the male influence he needed. Many of them were military veterans. So, straight out of high school, he enlisted in the Navy for four years. He says it gave him a sense of what was possible.

　　A Red Ferrari and a Turning Point

　　After the military, Gardner took a job as a medical supply salesman. Then, he says, he reached another turning point in his life. In a parking lot, he met a man driving a red Ferrari. He was looking for a parking space. And I said, You can have mine. But I gotta ask you two questions. The two questions were: What do you do? And how do you do that? Turns out this guy was a stockbroker and he was making $80,000 a month.

　　Gardner began knocking on doors, applying for training programs at brokerages, even though it meant he would have to live on next to nothing while he learned. When he finally was accepted into a program, he left his job in medical sales. But his plans collapsed as suddenly as they had materialized. The man who offered him the training slot was fired, and Gardner had no job to go back to.

　　Things got worse. He was hauled off to jail for $1,200 in parking violations that he couldnt pay. His wife left him. Then she asked him to care for their young son without her. Despite his lack of resources, Gardner said, I made up my mind as a young kid that when I had children, my children were gonna know who their father was. Although a broker finally helped him enter a training program, Gardner wound up with no place to live. He was collecting a meager stipend as a brokerage trainee, and, like many working poor in America, he had a job but couldnt make ends meet.

　　The Kindness of Strangers

　　When he could afford it, he stayed with his son, Chris Jr., in cheap motels. When they returned home at night, Gardner says, he received help from some unexpected sources. The ladies of the evening were beginning their shift. And they would always see myself, this baby and the stroller.

　　So they started giving him $5 bills. Without their help, Gardner said, there would have been nights when he couldnt have fed his son. The Rev. Cecil Williams, founder of Glide Memorial Church in San Francisco, remembers the first time he saw Gardner, who had gone to the church with his son to stand in a meal line. He said, I wondered, What in the world is a man doing with a baby?

　　Even to Williams, it was an unusual sight. The Urban Institute estimates that children make up 25 percent of the nations homeless population, but most are living with a single mother,not the father.