Which billionaire was homeless?

Becoming a billionaire is an incredible feat that few people achieve. However, some of the world’s richest people actually came from very humble beginnings, including experiencing homelessness. Rising up from difficult circumstances to become immensely successful is an inspiring narrative. So which famous billionaires were once homeless? Let’s explore the rags-to-riches stories of some remarkable individuals.

Jack Ma – China’s richest man

Jack Ma is the founder of Alibaba Group, one of the world’s largest e-commerce businesses. With a current net worth of over $25 billion, he is regarded as China’s richest man. However, Ma grew up in poverty and suffered hardship early in life. Born in 1964 to a poor family in Hangzhou, China, he struggled academically and failed his college entrance exams twice before finally being admitted to Hangzhou Teachers College. After graduating in 1988, Ma applied to dozens of jobs but was rejected from all of them, even KFC. In 1995, on a trip to Seattle, Ma was introduced to the internet for the first time. Inspired, he launched China Pages, one of the country’s first internet companies. The success of this venture laid the groundwork for Alibaba’s launch in 1999. But before finding success, Ma endured extended periods of homelessness and poverty.

In the late 1980s and early 1990s, Ma worked as an English teacher. With a salary of just $15 per month, he could not afford an apartment. Instead, Ma rented a tiny apartment with several roommates and would wake up early each morning to use a free hotel breakfast coupon so he could eat. When he could not find a room to rent, Ma slept in a university dormitory hallway and washed up using the school’s bathrooms. The future billionaire recalled, “For 10 years I never had a cent in my pocket, I couldn’t even afford to buy a Coke.” But Ma persevered through these tough times and went on to build one of the world’s most valuable companies.

Howard Schultz – Starbucks CEO

Howard Schultz is known for taking Starbucks from a small Seattle coffee roaster to the global giant it is today with over 32,000 stores worldwide. As CEO and Chairman of Starbucks, Schultz presided over one of the most impressive success stories in business history. At one point, he held a net worth of over $3 billion. However, life was not always so comfortable for Schultz. He grew up poor in Brooklyn housing projects and had a difficult childhood. In 1972, Schultz left home at age 18 after clashing with his father. Unsure of where to go, he rode aimlessly on the subway for a couple of hours. With no one to turn to and just $3 in his pocket, Schultz was essentially homeless at the time.

For the next couple of years, Schultz drifted between jobs and states, working when he could and crashing on friends’ couches. In an interview with CNBC, Schultz reflected that “I literally was on the streets at 18 years old with no place to live and no job.” His big break came in 1975 when Schultz was working as a salesman for Xerox and noticed the popularity of a small coffee shop in Seattle called Starbucks, which bought its coffee equipment from Xerox. Schultz soon joined Starbucks and became part of its expansion before leaving to found his own coffee company, Il Giornale. He bought out Starbucks in 1987 and grew it into a ubiquitous global brand. Despite starting from nothing, Schultz’s vision and tenacity made him a billionaire.

Oprah Winfrey – Media Mogul

Oprah Winfrey is one of the most influential women in the world, having built a wildly successful media empire. Born into poverty in rural Mississippi in 1954, Oprah experienced trauma and abuse as a child. At age 13, after suffering sexual abuse, she ran away from home. With no place to stay, Oprah slept on the streets and in strangers’ homes. She was sent to live with her father in Nashville, but he was strict and made her sleep on the porch as punishment when she broke his rules. Oprah reflected on this period, “I was homeless, but I always knew where home was. I think nobody actually realizes that they’re homeless.”

The next few years remained challenging for Oprah as she bounced between family members and continued her education. But remarkably, by age 19, Oprah had turned her life around by working in media. She got her first TV job as a news anchor for CBS in Nashville in 1971. This launched her broadcasting career. In 1986, The Oprah Winfrey Show was launched nationally and became the highest-rated daytime talk show ever. Oprah’s company Harpo Productions would go on to produce countless successful shows. Despite being a young homeless girl just years earlier, Oprah’s perseverance paid off and she is now worth an estimated $2.7 billion.

John Paul Dejoria – Patron Tequila and Paul Mitchell Hair

John Paul Dejoria is the billionaire co-founder of tequila maker Patron and hair care company John Paul Mitchell Systems. His current net worth is estimated at $2.6 billion. But before achieving massive success and wealth, Dejoria experienced poverty and homelessness firsthand. Born in 1944 in Los Angeles to immigrant parents, Dejoria’s father left the family when he was just 2 years old. He was raised by a single mother in Echo Park and East L.A. As a child, he would often accompany his mom picking up soda bottles for recycling money. When he was 9, his mother could no longer afford their apartment and they lived in a hotel, a car, and even slept on parks benches.

As a teenager, Dejoria joined a street gang for income and protection. He later worked any odd jobs he could find, including being a janitor and insurance salesman. However, Dejoria never gave up on his dreams of making it big. He and Paul Mitchell co-founded John Paul Mitchell Systems in 1980 with just $700. The hair care company took off and made Dejoria his first fortune. In 1989, he co-founded Patron tequila which also became incredibly successful. Despite a turbulent childhood marked by poverty and homelessness, Dejoria overcame the odds and became a highly successful entrepreneur.

Kenny Troutt – Founder of Excel Communications

Kenny Troutt is a self-made billionaire who built Excel Communications, a long-distance phone company. At one point, Troutt had a net worth of over $1.5 billion. However, he grew up poor and worked hard jobs from a young age. Born in 1948 in Illinois, Troutt grew up with an alcoholic father. As a 12-year old, he started selling newspapers for income. Troutt said his father would take his newspaper money and spend it on alcohol. “I learned what it was like to be poor at a very early age. I made the decision that poverty was not for me,” remarked Troutt.

When he was 15, Troutt dropped out of high school and left home. He was homeless and slept on the beaches of Florida and California. To get by, Troutt took up golf hustling. He would approach golfers and bet that he could beat them in a round. Hustling golf games helped earn him a little money as a homeless teen. In 1968, Troutt enlisted in the U.S. Army and served a tour in Vietnam. After returning from the war, Troutt became a successful stockbroker and then founded Excel in 1988, growing it into a $3 billion business before selling it to Teleglobe in 1998. Despite a difficult childhood and being homeless, Troutt achieved tremendous success as an entrepreneur.

Ralph Lauren – Fashion Icon

Ralph Lauren is an internationally renowned fashion designer known for brands like Polo Ralph Lauren. As chairman and CEO of Ralph Lauren Corporation, his net worth is estimated at $7.2 billion. However, Lauren came from humble beginnings. He was born Ralph Lifshitz in 1939 in Bronx, New York to Jewish immigrant parents from Belarus. As a teenager, Lauren attended a high school for troubled boys and dropped out at 16 years old after being accused of stealing the keys to the headmaster’s car. With no degree or direction, Lauren took odd jobs like selling gloves and ties at a department store.

At one point, with no stable housing, Lauren crashed at the dealership where he was working part-time as a salesman. He slept on the floor of the showroom to get by. In an interview with CNN, Lauren recalled, “I never considered myself homeless, but I didn’t have a home. So I guess I was relatively homeless.” The aspiring fashion designer used the showroom’s restroom to clean up and get ready for work each morning during this period. Despite the hardship, Lauren persevered and built a fashion empire that made him a billionaire.

Jim Cramer – Host of Mad Money

Jim Cramer is known for his bombastic television personality as host of CNBC’s Mad Money and other financial shows. He is also a former hedge fund manager. With an estimated net worth of $150 million, Cramer lives a comfortable lifestyle today. However, it was not always this way. Cramer grew up in a middle-class family in Pennsylvania. He graduated magna cum laude from Harvard in 1977 with a degree in government. But his career was slow to take off in those early years.

After graduating, Cramer tried working as a journalist in Florida but was homeless for nine months between jobs in the early 1980s. With just $150 left in his checking account and unable to afford an apartment, Cramer lived out of his car and showered at a local gym while continuing to search for work. He took on freelance projects and eventually got hired at the L.A. Herald Examiner in 1982. This launched Cramer’s journalism career, leading to television and finance jobs where he made his fortune. Despite living in his car, Cramer’s tenacity paid off.

Steve Jobs – Apple Founder

Steve Jobs developed Apple from its humble origins as a startup in his parents’ garage to one of the world’s most valuable technology companies. As Apple’s visionary leader, Jobs revolutionized personal computing and mobile technology with products like the Macintosh, iPod, iPhone, and iPad. At his peak, Jobs had an estimated net worth of $10.2 billion. However, life was not always glamorous for Jobs. He was given up for adoption as a baby and grew up in Mountain View, California after being adopted by Paul and Clara Jobs.

After dropping out of Reed College in Portland in 1972, the 18-year old Jobs was unsure what to do with his life. He returned to the Bay Area but lacked direction. For several months, he would sleep on the floor at friends’ homes, in dorms, or even just in local parks when he couldn’t find a place to crash. Jobs referred to this as his “dropout period.” He picked up occasional work at places like Atari and developed his interests in technology and design. By 1976, Jobs and his friend Steve Wozniak started Apple Computers and both became billionaires as the company grew explosively over the next decades. Jobs overcame early life struggles to leave an immense legacy.

Suze Orman – Personal Finance Guru

Suze Orman is famous for dishing out financial advice through popular books, television appearances, and podcasts. She developed a unique straight-talking personal finance philosophy that made her a New York Times bestselling author. Despite sharing her wisdom with millions of people, Orman struggled financially in her early life. She was born in Chicago in 1951 and grew up on the city’s South Side. After finishing college at the University of Illinois in 1976, Orman moved to Berkeley, California and worked as a waitress. Hoping to transition to a career as a writer, she instead ended up homeless and sleeping in her van.

In an interview with Business Insider, Orman reflected, “I was sleeping in my Ford Econoline van. I couldn’t get a job anywhere.” She lived like this for seven months, using money earned waitressing to occasionally get a hotel room for a night. Orman credit this rocky period with teaching her important lessons about money and not taking financial security for granted. She eventually became a stockbroker and financial advisor before shifting to full-time writing and television. Orman overcame homelessness and built a successful brand as America’s most prominent personal finance guru.

Halston – Fashion Designer

Roy Halston Frowick, known mononymously as Halston, was an American fashion designer who rose to fame in the 1970s and 1980s. His minimalist, clean designs made him a go-to designer for America’s rich and famous. Halston dressed notable clients like Jacqueline Kennedy Onassis, Elizabeth Taylor, and Liza Minnelli. At the peak of his success, he built a fashion empire that made him a multi-millionaire with an elite celebrity clientele.

However, Halston came from very little and faced substantial adversity on his road to fame and fortune. He was born in 1932 in small-town Des Moines, Iowa. His father worked as a milkman while his mother did sewing for wealthy local families. When Halston was still a young boy, his father left the family. Halston and his mother were suddenly impoverished and ended up homeless, living in cars and makeshift shelters for several years. During this time, Halston’s mother continued doing sewing work that helped inspire her son’s future fashion career. Despite homelessness and his family’s struggle with poverty, Halston was determined to make it in New York’s high fashion world.

David Geffen – Music & Film Mogul

David Geffen is a billionaire media mogul who founded Asylum Records and Geffen Records and co-founded DreamWorks SKG film studio. With an estimated net worth of $11 billion, Geffen has been incredibly influential in the American entertainment industry since the 1970s. But before becoming a legendary music and film producer, he faced hardship. Geffen was born in Brooklyn in 1943. When he was a young teen, his single mother moved the family to Brooklyn. She worked in the garment district in Manhattan.

However, over time Geffen began having conflicts with his mother and stepfather. At age 18, he left home and was homeless in New York City for months. To survive, he would sneak rides on cruise ships going to Florida and work odd jobs there. Geffen reflected on being homeless saying, “It was wretched. I cried every night. I was terrified.” It was on a cruise ship trip that Geffen met a woman who inspired him to move to Los Angeles and get into the entertainment business. His determination during homelessness led Geffen to become the powerbroker he is today.


The rags-to-riches stories of these billionaires show that homelessness and poverty do not have to be permanent obstacles preventing success. Hard work, perseverance through struggles, and vision can ultimately transform difficult life circumstances. From humble, destitute beginnings, these individuals rose to the greatest heights of fame, influence, and wealth. Their stories reveal that the American dream of opportunity and upward mobility is still attainable for the most disadvantaged people with the right mindset and determination.

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