Gardner did not have many positive male role models as a child, as his father was living in Louisiana during his birth, and his stepfather was physically abusive to both his mother and his sisters.

[1] In one incident, Bettye Jean was imprisoned when Triplett falsely reported her to the authorities for welfare fraud; the children were placed in foster care.

When Gardner was eight years old, he and his sisters returned to foster care for the second time when their mother, unbeknownst to them, was convicted of trying to kill Triplett by burning down the house while he was inside.

Of the three, Henry had the most profound influence on him, entering Gardner's world at a time when he most needed a positive father figure.

[2] Despite both her very unhappy marriage and her periods of absence, Bettye Jean was a positive source of inspiration and strength to her son Chris.

[1] Inspired by his Uncle Henry's worldwide adventures in the U.S. Navy, Gardner decided to enlist when he finished secondary schooling.

Gardner was advised to consider more lucrative career options; a few days before his 26th birthday, he informed his wife, Sherry, of his plans to abandon his dreams of becoming a physician.

With a higher income from his new job, Gardner was able to save enough money to travel to Monroe, Louisiana, where he and his son met his father, Turner, for the first time.

A pivotal moment in his life occurred, after a sales call to a San Francisco General Hospital when he encountered an impeccably dressed man in a red Ferrari.

Bridges organized meetings between Gardner and branch managers at the major stock brokerage firms that offered training programs—such as Merrill Lynch, Paine Webber, E.F. Hutton, Dean Witter Reynolds, and Smith Barney.

For the following two months, Gardner canceled or postponed his sales appointments, and his car amassed parking tickets while he met with managers.

Gardner was apprehended initially for this incident, but an identity check on his car license plate led them to detain him for non-payment of parking fines.

[6][better source needed] He was taken to jail and a judge ordered that he stay there, for ten days, as punishment for being unable to pay $1,200 in parking tickets.

With no experience, no college education, virtually no connections, and with the same casual outfit he had been wearing on the day he was taken into custody, Gardner gained a position in Dean Witter Reynolds' stock brokerage training program.

However, this offered no salary; apart from selling medical equipment that brought in 300–400 dollars a month in the early 1980s, and with no savings, he was unable to meet his living expenses.

Although he was gainfully employed, Gardner and his son secretly struggled with homelessness while he saved money for a rental house in Berkeley.

[citation needed] Meanwhile, none of Gardner's co-workers knew that he and his son were homeless in the Tenderloin District of San Francisco for nearly a year.

Gardner often scrambled to place his child in daycare, stood in soup kitchens and slept wherever he and his son could find safety—in his office after hours, at flophouses, motels, parks, airports, on public transport, and even in a locked bathroom at a BART station.

"[7] His new company was started in his small Presidential Towers apartment, with start-up capital of $10,000 and a single piece of furniture: a wooden desk that doubled as the family dinner table.

Gardner was planning an investment venture there which he hoped would create hundreds of jobs and introduce millions in foreign currency into the country's economy.

[12] Gardner is a philanthropist who sponsors many charitable organizations, primarily the Cara Program and the Glide Memorial United Methodist Church in San Francisco, where he and his son received desperately needed shelter.

[7] He has helped fund a $50 million project in San Francisco that creates low-income housing and opportunities for employment in the area of the city where he was once homeless.

"When I talk about alcoholism in the household, domestic violence, child abuse, illiteracy, and all of those issues—those are universal issues; those are not just confined to ZIP codes," he said.