10 Millionaires Who Lived on the Streets

Everyone loves a rags to riches story, confirming as it does the belief that human ingenuity and hard work can overcome any barriers. Going from a life on the streets to having millions of dollars in the bank is a reversal of fortune that can scarcely be believed — it’s the American Dream in the extreme — but these ten millionaires all spent time without a roof over their heads before they made it.

10. Halle Berry

The Oscar-winning actress has played a wide variety of roles in her time — everything from the wife of a convicted murderer to Catwoman – but before becoming a household name she was a struggling actress, down on her luck and without a place to rest her head. When she was 21 and embarking upon an acting career in New York City, she spent time in a homeless shelter after her mother refused to give her any more money. The two didn’t speak for a year-and-a-half, although Berry claims the experience made her stronger: “I’m actually grateful she did that, because it taught me how to take care of myself and that I could live through any situation, even if it meant going to a shelter for a small stint.” Now she spends her days on Hollywood sets with a cool $70m to her name.

9. “Colonel” Harland Sanders

A man so determined in his campaign against the chicken that he was given a “military” title, Harland Sanders was also homeless not once, but twice. As a child he ran away from home after altercations with his stepfather. But he put that experience to good use when he perfected his famous chicken recipe. He slept in the back of his car as he traveled around North America with his delicious recipe (and wife Claudia) trying to persuade restaurants to pay a franchise fee. The brand that he built netted him $2m (almost $15m in today’s money) when he sold it in 1964 — a feat that can be put down both to his impressive tactics in the war against poultry and the fact that his chicken is just so finger-lickin’ good.

8. “Dr. Phil” McGraw

Dr Phil is American’s most well-known psychologist, with millions tuning in to his TV show and buying his best-selling books, but his success was built on a childhood spent in poverty. Aged 12, McGraw was homeless and living in a car with his father in Kansas City while McGraw senior interned as a psychologist. They eventually scraped up the money for a $5 room at the YMCA, and though it was tough, McGraw says, “I cherish those memories. That was my time to learn how to deal with stress and adversity — lessons I’d never have learned any other way at that age. I learned what it meant to work hard, to stay focused, and to set goals.” Dr Phil is now rich in fame and cash with a net worth estimated at $200m.

7. Christopher Gardner

As detailed in his memoir The Pursuit of Happyness (and as portrayed by Will Smith in the film of the same name), natural talent and a whole lot of hard work brought Christopher Gardner from the streets to the big time. He sold his stake in his stockbrokerage company for millions in 2006, but had a hard road to get there, suffering through the breakdown of his marriage, jail time for unpaid parking tickets, and the struggle to provide a safe life for himself and his young son. Throughout his time sleeping in his office, at a railway station, in homeless shelters and in parks around San Francisco, he kept up an impeccable record at his workplace and cared for his son. He is now CEO and founder of Christopher Gardner International Holdings and has a net worth of over $165m.

6. Jerry Winkler

Jerry Winkler had a hard 28 years of life, with his childhood peppered with trauma. His mother was ill with a brain tumor, and the man he thought was his father took him in — but their relationship was strained and he spent five years in the care system. He became involved in drugs and petty crime before finding out that the man he believed to be his father was not and that in fact he was the only heir of deceased multimillionaire businessman Alfred Winkler. A DNA test confirmed the paternity, and Jerry went from the streets to a palatial house in the center of Amsterdam. He did not forget his life on the streets, however, and used his newfound wealth to set up a foundation to help homeless young people.

5. Richard Leroy Walters

You should never judge a book by its cover, and the case of Richard Walters is one of the best examples of why. In a surprise twist, it turned out that Richard Walters had been a marine, had a master’s degree and made his millions as a jet propulsion engineer for Allied Signal Aerospace before becoming homeless. It seems that he chose to be homeless after being forced into early retirement, as he certainly didn’t end up on the streets due to a lack of funds: upon his death he left $4m to charities including the Mission of Mercy in Phoenix and National Public Radio. While on the streets, he slept on the grounds of a senior center, ate at a hospital and continued investing his wealth, increasing his worth such that he could leave such substantial bequests when he died in 2007. The American Dream in reverse.

4. Michael Parness

Micheal Parness was once a high school dropout who slept rough on the streets. From those less than auspicious beginnings, he set up a sports memorabilia company in New York before branching out into brokerage when bad advice from a broker friend lost him his life savings. He turned $33,000 into $7m within two years and is now a best-selling author on investment and finance who runs an investment advice business.

3. Stuart Sharp

Stuart Sharp spent ten years living rough on the streets after the death of his infant son contributed to the breakdown of his marriage. A “vision” of soothing music took hold of him, and despite an inability to read or write music he composed a 40-minute symphony in memory of his child, described by experts as “genius,” that has been recorded by the London Philharmonic Orchestra. After ten years on the streets, jazz musician Anthony Wade found Sharp sleeping rough outside the BBC Television Center and gave him a place to stay. Sharp turned his life around, making millions in sales and property development, finally allowing him to buy a recording studio and fulfill the dream he had held since his son’s tragic death.

2. Bob Williamson

Bob Williamson sold his company for $75m in 2008, but as a teenager he was an alcoholic, attended 19 different schools, was an intravenous meth and heroin user, carried a .357 magnum and committed armed robberies. However, a head-on car collision and a hospital stay at the age of 22 led him to discover his faith, convert to Christianity and meet his future wife of 40 years. This shock to the system put him back on the straight and narrow, and he set himself up in the art supply business before founding Horizon Software International in 1993. The company monitors and facilitates meals in schools, hospitals, corporations and the military, allowing online payments and meal monitoring, and as of 2008 had sales of $26m.

1. John Paul Jones DeJoria

John Paul Jones DeJoria began working from an early age, selling Christmas cards and newspapers at the age of nine. When he was taken into foster care he was involved with gangs in Los Angeles until a high school math teacher told him he would “never, ever succeed at anything in life.” DeJoria set out to prove him wrong. In his early twenties, following a divorce, he was homeless and living on the streets with his son, but that didn’t stop him from going from a hair care employee to co-founder, with hairdresser Paul Mitchell, of John Paul Mitchell Systems. The hair products company now rakes in a very impressive $900m annually and Forbes rates DeJoria’s net worth as $4bn.

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