Five Americans Who Started With Almost Nothing and Built Something Extraordinary — and the Strange Roads That Got Them There

There's a version of the American success story that gets told so often it's lost most of its texture. Rags to riches. Hard work pays off. Anyone can make it if they try hard enough. The clichés aren't entirely wrong — but they flatten the reality into something almost useless, stripping out the accidents, the pivots, the specific weird decisions that actually made the difference.

The five people below built significant wealth or influence from genuinely improbable starting points. Their stories aren't templates. They're too strange and specific for that. But taken together, they suggest something real: that in America, the odd path has historically been the great one.

1. John Paul DeJoria — From Homeless to Billionaire, One Shampoo Bottle at a Time

In 1980, John Paul DeJoria was living in his car. He was thirty-six years old, had been fired from multiple jobs, and had a young son he was struggling to support. He'd worked as a janitor, sold encyclopedias door-to-door, and bounced through the beauty industry without much to show for it.

With a $700 loan, he and hairstylist Paul Mitchell mixed up their first batches of professional shampoo in a small facility and started knocking on salon doors. Most of them said no. DeJoria was turned away so many times that he developed a near-philosophical relationship with rejection — he later said he expected nine out of ten people to say no, and simply needed to find the one who'd say yes.

John Paul Mitchell Systems grew slowly, then quickly, then enormously. DeJoria eventually co-founded Patrón Tequila, which sold to Bacardi in 2018 for roughly $5.1 billion. His personal fortune has been estimated at over $3 billion. He's given away hundreds of millions to charitable causes.

He was living in his car less than fifty years ago. The math on that is genuinely staggering.

2. Sam Walton — The Depression-Era Dropout Who Rewired American Retail

Sam Walton grew up during the Great Depression in rural Missouri, in a family that moved constantly to chase whatever work was available. His father traded farms, sold mortgages, and repossessed property from struggling families — not because he was cruel, but because that's what there was to do. Young Sam milked the family cow and sold the milk to neighbors. He delivered newspapers. He understood early that money didn't just appear; it had to be worked for, carefully, and kept even more carefully.

He dropped out of his early retail management path more than once, made a catastrophic early business mistake — signing a lease on his first store that allowed the landlord to reclaim the property once he'd built it into something profitable — and had to start over from scratch in his mid-thirties.

What he built instead, from a small variety store in Bentonville, Arkansas, was Walmart: the largest private employer in the United States, a company that fundamentally reshaped American commerce, supply chains, and small-town economies in ways that are still being debated. By the time Walton died in 1992, he was one of the wealthiest people in the world.

He drove an old pickup truck until the end of his life. He ate at the local barbershop lunch counter. The fortune was almost incidental to the problem he'd spent his whole life trying to solve: how do you get good products to people who can't afford to pay much for them?

3. Liz Claiborne — The Self-Taught Designer Who Built a Fashion Empire Without a Business Plan

Liz Claiborne never finished high school in the conventional sense. She studied art in Belgium and France, learned to sketch and sew through sheer persistence, and eventually talked her way into the New York garment industry in the 1950s — an industry that was, at the time, almost entirely male at the top.

She spent nearly twenty years working for other people, climbing slowly through design roles while developing a precise understanding of what American women actually wanted to wear to work — as opposed to what the industry assumed they wanted. When she launched her own label in 1976 at the age of forty-seven with $50,000 in personal savings and a small group of partners, the premise was almost radical in its simplicity: affordable, mix-and-match separates for professional women entering the workforce in large numbers for the first time.

The timing was exact. The product was right. Liz Claiborne Inc. became the first company founded by a woman to make the Fortune 500, and by the late 1980s it was pulling in over a billion dollars annually. She'd spent two decades waiting for the right moment, and then built something the industry hadn't seen coming.

4. Do Won Chang — $200, a Dream, and the Store That Became Forever 21

In 1981, Do Won Chang arrived in Los Angeles from South Korea with his wife Jin Sook and less than $200 between them. He worked three jobs simultaneously — at a gas station, a coffee shop, and a janitorial position — and noticed something: the people who drove the nicest cars all seemed to work in the garment industry.

That observation became a business plan. In 1984, the Changs opened a small clothing store in Los Angeles called Fashion 21. In its first year, it brought in $700,000. They reinvested almost everything, opened more stores, and eventually renamed the brand Forever 21.

At its peak, Forever 21 operated over 800 stores across 57 countries, employed tens of thousands of people, and was generating nearly $4 billion in annual revenue. The Changs built one of the most recognizable fast-fashion brands in the world from a standing start, with no industry connections, no formal business education, and almost no starting capital.

The brand filed for bankruptcy in 2019, a cautionary chapter in a story that remains remarkable for everything that preceded it. Do Won Chang arrived in America with less than the cost of a nice dinner and built something that dressed a generation.

5. Ursula Burns — The Kid From the Lower East Side Who Ran Xerox

Ursula Burns grew up in a housing project on the Lower East Side of Manhattan, raised by a single mother who took in ironing and watched other people's children to make ends meet. Her mother, by Burns's own account, was ferocious about education — she sent her daughter to Catholic school on money she didn't really have, because she believed it was the one lever she could pull.

Burns was brilliant at math. She earned a scholarship to study engineering, got her master's degree from Columbia, and took an internship at Xerox in 1980 — the kind of internship that was supposed to be a summer job and turned into a forty-year career. She rose through engineering and operations, made herself indispensable, and in 2009 became the CEO of Xerox.

That made her the first Black woman to lead a Fortune 500 company in American history — and the first woman to succeed another woman as CEO of a Fortune 500 company. She ran Xerox through one of the most turbulent periods in the company's history, navigating a massive restructuring and a split into two separate public entities.

She grew up in a housing project. She ran one of America's most storied corporations. The distance between those two points is the kind of thing that makes the phrase "only in America" feel less like a cliché and more like a statement of documented fact.

What These Five Lives Tell Us

None of these stories followed the expected script. The homeless shampoo salesman, the Depression kid with the bad lease, the self-taught designer who waited until her late forties, the immigrant with $200 and a notebook full of observations, the girl from the projects who became the most powerful executive in American corporate history.

They didn't succeed because the path was clear. They succeeded because they kept moving when it wasn't. That's not a formula — it's a pattern. And it shows up, again and again, in the lives of the people who end up mattering most.

The odd path, historically, has been the great one.