Table of Contents
Most self-made fortunes get boiled down to one lucky break: the right product, the right year, the right buyer. Dig a layer deeper and the luck starts looking suspiciously well-prepared. The seven people below started with a dead parent, a rented room shared with a baby, a few hundred dollars, or a car doubling as a bedroom. Every one of them finished with a nine- or ten-figure fortune, and every one of them took between twenty and fifty years to get there. That last detail separates them from the people who became millionaires overnight and then discovered how fast that kind of money can move.
1. Li Ka-shing: Plastic Flowers and a Bet Against Panic
Li was born in 1928 in Chaozhou, China. When war pushed the family to Hong Kong, his schoolteacher father contracted tuberculosis and died, and fifteen-year-old Li became the household’s only earner. He worked sixteen-hour days in a plastics factory, first on the floor, then selling, and by his early twenties he was effectively running the place.
In 1950 he founded Cheung Kong Industries with roughly HK$50,000 of savings and family loans. The product was plastic flowers, sold to export markets. Eight years later he moved into property, and in 1967, while riots sent Hong Kong buyers running, he used the crash to buy land cheaply. That single decision turned a factory owner into a landlord with real leverage. In 1979 he took control of Hutchison Whampoa, a deal that put him on the list of the wealthiest people in the world and kept him there for decades.
2. Oprah Winfrey: Owning the Show Instead of Starring in It
Born in 1954 in Kosciusko, Mississippi, to a teenage mother, Winfrey spent her early years with her grandmother, wearing dresses sewn from potato sacks. She was reading at three and speaking in church at five. By 19 she had a radio job in Nashville. By 1984 she was hosting a struggling Chicago talk show and pushed it to number one in the market within months.
The financial move came in 1988, when she took ownership of her own show through Harpo Productions. That decision separated her from nearly every other television performer. Instead of collecting a salary, she collected the underlying business. She became the first Black woman to reach billionaire status in 2003, and a 10% stake in Weight Watchers added around $400 million in value in a single day in 2015. It is a very different structure from how even the richest actors in the world actually earn their billions, where the production usually belongs to somebody else.
3. Zhong Shanshan: Bottled Water and Four Decades of Patience
Zhong left school in Hangzhou when the Cultural Revolution shut the classroom doors, then spent years doing manual construction work before talking his way into a reporter’s job at the Zhejiang Daily. He started a health supplement company in 1993 selling turtle-shell tonic, then founded Nongfu Spring in 1996.
His timing was sharp. Chinese households were switching from boiled tap water to sealed bottles just as distribution networks reached the smallest corner shops. He built routes into millions of tiny retailers rather than chasing supermarket shelf space. The Hong Kong listing in 2020 briefly made him Asia’s richest person, with a paper fortune that topped $70 billion at one stage.
4. John Paul DeJoria: Door-to-Door With $700
DeJoria grew up in Los Angeles, joined a gang as a teenager, spent two years in the US Navy, then worked a string of jobs that at one point included collecting bottles for refunds while living in his car with his wife and young son.
In 1980 he partnered with hairdresser Paul Mitchell to sell shampoo directly to salons. They had $700, one product, and a promise to keep going until the money ran out. DeJoria sold door to door and slept in his car between appointments. John Paul Mitchell Systems went on to generate hundreds of millions in annual revenue. In 1989 he co-founded Patrón tequila, a brand valued at more than $5 billion when Bacardi took control. He has since signed the Giving Pledge, committing most of his wealth to charity.
5. Do Won Chang: Three Years of Sweeping Floors
The Changs arrived in Los Angeles from Seoul in 1981. Do Won worked as a janitor, a gas station attendant and a coffee shop employee, often holding several jobs at once, while the couple saved for three years. In 1984 they put $11,000 into a 900-square-foot store in Highland Park and called it Fashion 21.
The formula was fast fashion before the phrase existed: cheap, trend-led clothes restocked weekly. First-year sales hit about $700,000 and the chain became Forever 21, growing to hundreds of stores and more than $4 billion in revenue, with the family fortune once estimated near $5 billion. Then the rise stopped. Overexpansion, larger competitors and thin margins pushed the company into bankruptcy in 2019. Other billionaires have watched the same story play out, which is why fixed costs matter so much in retail.
6. Guy Laliberté: A Fire-Eater With a Government Grant
Laliberté left home in Quebec City at 18 and hitchhiked across Europe playing accordion for coins. Back in Canada he walked on stilts, breathed fire and organised street festivals, then pitched a circus without animals for the 1984 celebrations marking the 450th anniversary of Jacques Cartier’s arrival.
He secured a $1.5 million government grant and a cast of 73 performers. Cirque du Soleil grew from a travelling tent show into a permanent fixture in Las Vegas, with several productions running at once and annual revenue in the hundreds of millions. Selling majority stakes in stages made Laliberté a billionaire. He spent some of it the way a former street performer might: playing high-stakes poker tournaments and paying around $35 million for a seat on a Russian spacecraft to the International Space Station in 2009.
7. Kirk Kerkorian: Eighth Grade, Then Bombers
Kerkorian was born in 1917 in Fresno, California, to Armenian immigrant parents. His father’s fruit farming failed, the family moved constantly, and he left school in the eighth grade. He boxed for prize money, learned to fly, and during the Second World War ferried heavy bombers across the Atlantic for the RAF ferry command.
After the war he bought surplus aircraft and built a charter airline, selling it in 1968 for about $104 million. He then moved into Las Vegas hotels, buying and reselling the same properties more than once, and eventually controlled MGM. By the time he died in 2015 his fortune was around $4 billion, most of which went to charity.
The Habits That Show Up Again and Again
Read enough of these stories and the same operating patterns keep surfacing.
- They sold something people rebuy weekly. Shampoo, bottled water, cheap clothes, show tickets. Repeat purchases forgive a long list of beginner mistakes.
- They held equity, not a salary. Winfrey owning her show and DeJoria owning his brand made a bigger difference than any pay rise could have.
- They bought when the room was empty. Li Ka-shing’s 1967 land purchases and Kerkorian’s hotel deals in soft markets both relied on doing the opposite of the crowd.
- They ran lean for years. One store, one product, a car used as accommodation. Low fixed costs bought them the time to be wrong a few times.
- They gave it decades. Kerkorian was ferrying bombers at 24 and buying hotels in his fifties. Chang swept floors for three years before renting that first shop front.
The uncomfortable part is the arithmetic. None of these fortunes came from a shortcut or a hidden product. They came from a fairly boring idea repeated for far longer than most people are willing to stay interested, with the compounding doing the heavy lifting in the background. Twenty years is not a long stretch in that kind of business. It only feels like one while you are living through it.
