Top 25
Self-Made Billionaires
of All Time

Ran track at the University of Oregon under legendary coach Bill Bowerman. After earning an MBA from Stanford, he wrote a term paper about importing high-quality, low-cost Japanese running shoes to compete with German brands like Adidas. He flew to Japan, struck a deal with Onitsuka Tiger, and started selling shoes from the trunk of his green Plymouth Valiant at track meets. He and Bowerman each put up $500 to start Blue Ribbon Sports in 1964, which became Nike in 1978.

Glen's Take: Knight's memoir Shoe Dog is the best founder autobiography ever written, and I do not say that lightly. His story is pure hustle: selling shoes from a car trunk, almost going bankrupt multiple times, fighting with Japanese suppliers, getting sued by his own distributor. Nike's swoosh is the most recognized brand mark on Earth and it cost $35 from a graphic design student.

Born in the Bayview Housing Projects in Canarsie, Brooklyn. His father was a truck driver who broke his ankle on the job and lost his income with no health insurance or workers' comp. That childhood experience drove Schultz to build a company that gave healthcare benefits to every employee, including part-timers. He earned a football scholarship to Northern Michigan University, then worked at Xerox before discovering a small Seattle coffee chain called Starbucks.

Glen's Take: Schultz did not invent coffee. He imported a culture. The insight that Americans would pay $5 for a latte in a comfortable environment was considered insane in 1987. His decision to give health benefits to part-time workers was moral AND strategic — it reduced turnover to a fraction of the industry average. That is how you build a $115 billion company.

Born in Hangzhou, China. Failed the national college entrance exam twice, finally passed on his third attempt and attended Hangzhou Teacher's Institute. He applied to 30 jobs and was rejected from all of them, including KFC (they hired 23 of 24 applicants, and he was the one rejection). He learned English by giving free tours to foreign visitors at West Lake. He first saw the internet during a trip to Seattle in 1995 and started his first internet company the same year.

Glen's Take: Jack Ma is the ultimate rejection story. Rejected from Harvard 10 times. Rejected from every job he applied to. Failed his college entrance exams. Then he built the largest e-commerce company in the world's largest market. The lesson is brutally simple: the market does not care about your resume. It cares about what you build.

Born in Chaozhou, Guangdong, China. His family fled to Hong Kong during the Japanese invasion when he was 12. His father died of tuberculosis two years later, and Li dropped out of school to support his family, working 16-hour days in a plastics factory. By 22, he started his own plastics company, Cheung Kong Industries. He gradually expanded into real estate, shipping, telecommunications, retail, and infrastructure across 50+ countries.

Glen's Take: Li Ka-Shing is the most disciplined capital allocator in Asia, possibly the world outside of Buffett. He built CK Hutchison into a conglomerate spanning ports, telecom, retail, infrastructure, and energy across 50 countries. He arrived in Hong Kong as a 12-year-old refugee and became the richest person in Asia for decades. His nickname is 'Superman Li' and it is earned.

Born in Busdongo de Arbas, Spain. His father was a railway worker. The family moved to A Coruna in Galicia, and Ortega left school at 14 to work as a shop assistant in a shirt store. He taught himself tailoring, started making bathrobes and lingerie from his living room, and in 1975 opened the first Zara store in A Coruna. He realized that speed — getting runway trends into stores within two weeks instead of six months — was the ultimate competitive advantage.

Glen's Take: Ortega is the most private billionaire on this list. For decades, there were only two known photographs of him. He never gave interviews. He built Zara into the world's largest fashion retailer through pure operational excellence — no celebrity endorsements, no flashy advertising, just the fastest supply chain in the industry. He briefly surpassed Bill Gates as the world's richest person. From a railway worker's son who left school at 14.

Born in Chorwad, Gujarat, India. His father was a school teacher. At 16, he moved to Aden, Yemen and worked as a gas station attendant and clerk for A. Besse & Co. He returned to India in 1958 with 50,000 rupees (about $1,000) and started trading spices and textiles from a one-room office in Mumbai with one assistant and one desk. In 1966, he founded Reliance Commercial Corporation, which grew into Reliance Industries — India's most valuable company.

Glen's Take: Ambani is arguably the most important entrepreneur in Indian history. He went from pumping gas in Yemen to building India's largest company and convincing an entire country to invest in the stock market. His sons Mukesh and Anil continued the legacy (Mukesh is now the richest person in Asia). The Ambani story is the story of modern India's economic transformation.

Born Ralph Lifshitz in the Bronx to Belarusian Jewish immigrant parents. He changed his last name as a teenager because classmates mocked it. He never attended fashion school, never worked for a fashion house, and had zero industry connections. He started by designing wide ties and selling them from a single drawer in the Empire State Building. From that one drawer, he built a $12 billion fashion empire and became the longest-tenured designer in American fashion history.

Glen's Take: Ralph Lauren sold a lifestyle, not clothes. He understood that a kid from the Bronx with no fashion credentials could build the most aspirational American brand ever by selling a vision of old-money elegance that he invented out of thin air. The brand IS the product. That insight is worth $8.5 billion.

Born in a small village outside Kyiv, Ukraine. His family immigrated to Mountain View, California when he was 16. They lived in a small apartment on food stamps. His mother worked as a babysitter. Koum swept floors at a grocery store. He taught himself computer networking from used manuals he bought at a thrift store and returned for a refund after reading them. He worked at Yahoo for nine years, then left to build WhatsApp with $400,000 of his savings.

Glen's Take: Koum's story is the American Dream in its purest form. Food stamps to $19 billion in 17 years. He built the most-used messaging app on Earth (2 billion+ users) with a team of 55 engineers. No ads. No tracking. No bloat. The anti-Silicon-Valley Silicon Valley story. That acquisition photo at the food stamps office is the most powerful image in tech history.

Failed the LSAT twice, spent seven years selling fax machines door-to-door for Danka. At 27, she cut the feet off her pantyhose, liked how it looked under white pants, and realized no one made footless shapewear. She wrote her own patent, cold-called hosiery mills (all run by men who did not understand the product), and spent two years getting doors slammed in her face. She launched Spanx with $5,000 of her own money and no outside investors.

Glen's Take: Blakely is proof that the best business ideas come from personal frustration, not Harvard Business School. She had no fashion experience, no business degree, no investors, and no connections. She had $5,000 and a pair of scissors. The fact that she built Spanx to a billion-dollar valuation with zero outside capital is one of the most impressive feats in modern entrepreneurship.

Born Shawn Corey Carter in the Marcy Houses public housing project in Brooklyn. His father abandoned the family when he was 11. He sold crack cocaine as a teenager to survive and was shot at three times. No record label would sign him, so he and two partners founded Roc-A-Fella Records with $3,000 and sold CDs out of their car trunks. His debut album Reasonable Doubt, now considered one of the greatest rap albums ever, initially sold modestly but built a cult following that launched an empire.

Glen's Take: Jay-Z is the best pure business mind in entertainment history. He understood ownership before the streaming era made it obvious. Roc Nation, the 40/40 Club, his Armand de Brignac champagne, his stake in Tidal, his art collection, his real estate portfolio. He diversified like a hedge fund manager while maintaining cultural relevance for three decades. From Marcy Projects to $2.5 billion. Respect.

Born in Budapest, Hungary in 1930. Survived the Nazi occupation as a 14-year-old by using forged identity papers. He fled communist Hungary in 1947, arrived in London as a penniless refugee, worked as a railway porter and waiter, and eventually earned a degree from the London School of Economics studying under Karl Popper. He moved to New York in 1956 and started the Quantum Fund in 1969.

Glen's Take: A Holocaust survivor who became the most feared currency trader in history. Soros developed the theory of reflexivity — that market participants' biases can actually change market fundamentals, creating feedback loops. He has given away over $32 billion to charity, more than almost any other living person. His actual net worth, before charitable giving, would put him in the top 10 richest people ever.

Immigrated to the United States from South Korea in 1981 with his wife Jin Sook and almost no money. He worked three jobs simultaneously — janitor, gas station attendant, and coffee shop worker — for three years. He noticed that the wealthiest people in LA drove nice cars and wore nice clothes, so he and his wife opened their first clothing store, Fashion 21, in Highland Park, LA in 1984 with $11,000 in savings. The store did $700,000 in its first year.

Glen's Take: Chang worked three jobs simultaneously as a new immigrant and still found the energy to study why rich people were rich. Then he built his own answer. Forever 21 eventually filed for bankruptcy in 2019 after over-expanding, but the rise from janitor to billionaire in one generation is the kind of story that makes America extraordinary.

Arrived in Champaign, Illinois from Lahore, Pakistan at age 16 with $500. His first night in America, he washed dishes for $1.20 an hour. He studied at the University of Illinois, got an engineering degree, and took a job at Flex-N-Gate, an auto parts company. In 1980, he bought the company from his boss and began a relentless campaign to win contracts from the Big Three automakers.

Glen's Take: Khan is the most under-the-radar self-made billionaire in America. He arrived with $500, washed dishes, and now owns an NFL franchise, a Premier League soccer club, and one of the largest private companies in the country. He did it in the least glamorous industry imaginable — auto parts manufacturing. No tech hype, no venture capital, no press coverage. Just decades of grinding execution.

Born in Echo Park, Los Angeles to Greek and Italian immigrant parents. His parents divorced when he was two. He was homeless twice — once as a young adult living in his car, and again in his 20s. He sold encyclopedias door-to-door, worked as a janitor, and pumped gas. In 1980, he and hairstylist Paul Mitchell pooled $700 to start a hair care company. DeJoria went door-to-door selling the products salon by salon.

Glen's Take: DeJoria was homeless. Twice. He started a billion-dollar hair products company with $700 and a lot of door-knocking. Then he did it AGAIN with Patron Tequila. Two separate billion-dollar brands from a guy who lived in his car. If you ever think your situation is too tough to start a business, read DeJoria's story and recalibrate your definition of tough.

Severely dyslexic, struggled in school, and dropped out at 16. His headmaster's parting words: 'You will either go to prison or become a millionaire.' He started Student magazine at 16, then launched Virgin Records by selling mail-order records to fund the magazine. He signed Mike Oldfield's Tubular Bells, which sold 5 million copies and funded the expansion into airlines, telecom, health clubs, space travel, and 400+ other Virgin-branded companies.

Glen's Take: Branson is the most fun billionaire alive. He launched an airline, a record label, a space tourism company, a mobile carrier, a gym chain, and 400 other businesses. He kitesurf across the English Channel, attempted to circumnavigate the globe in a balloon, and runs his empire from a private Caribbean island. He proved you can build a multi-billion-dollar brand on personality and customer experience alone.