5 Millionaires Who Started Out Homeless And Broke

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by Pauli Poisuo

Some people start building their professional lives from the bottom. Others start so far down that they don't even get to see the bottom before fighting their way up from life's sub-basements. And then there are these people, who started out without so much as a roof over their heads ... but with a combination of grit, gristle and plain old luck, managed to rogue their way to ridiculous success.

Who's up for some feel-good rags to riches stories? Because man, do we have some.


A Desperate Woman Living In Her Car Turns A Random Weight Loss Program Into A Business Empire

In 1990, 21 year old Dani Johnson was homeless, locked in a downward spiral of destructive party bingeing. To give you an idea of the place she was in, allow her to tell you how her weeks leading up to Christmas went:

"I was stoned out of my mind for two months -- sleeping with eight different guys. I got to eat only by dating all these people. I realized that I had become worse than the family I grew up in and that was devastating."

On Christmas Eve, she attended an "end of the world" party with a coworker from the restaurant she was working in. When she woke up the next day on a mat on the beach, nursing a budding drug addiction and a double scoop of existential terror, she realized that this was a crossroads moment. She had two options: She could either keep sinking further down into the pit, or start clawing her way out by any means necessary. She would later say that she heard a voice that said: "Pick up your mat and walk." Which she did.

During the 45-minute drive back to the beach where she lived (in her car), she made some grim calculations. To get out of her destructive cycle, she had to stop being homeless. The problem was that she lived in Hawaii, where rent was outrageous. With her cocktail waitress job, it would take 4 months to save up the $4,500 she calculated she'd need for rent and deposit. There had to be a better way. An "any means necessary", if you will.

Step 1: Get an awesome jacket with neck buttons.

Suddenly, an idea hit her. On the backseat of her car, among all her worldly possessions, was an old weight loss program she had purchased ages ago. She looked up the manufacturer's details, got on a payphone to see if she could start peddling the product, and ... was immediately shot down, because the manufacturer wanted her to get a license, which required money she didn’t have.

So Johnson got her rogue mode on. With her last quarter, she pay-phoned a small telecommunications company and sweet-talked them into opening her a voicemail service that she'd pay by sending them a check for $15 (that, unbeknownst to them, she did not yet have). Then, she hand wrote a flyer for the program, with the number of the voicemail for orders, and put it up at the local post office.

When she checked the voicemail three hours later, she already had 25 orders. During her first month, she sold $4,000 worth of the diet program. So she called the manufacturer, placed an order (using a local liquor store as a delivery address), and BOOM! She had a business. And what a business it was. She made $250,000 in her very first year and was a millionaire by the second. By the time she sold the business in 1996, she had 18 weight loss centers all over the country. Today, she's a multimillionaire who runs 5 companies and gives generously to various charities.

A Poor Homeless Teenager Messes Around With Library Computers, Becomes A Digital Company Millionaire

In 2007, Mylo Kaye from Wirral, UK was a 19-year-old who had just been fired from his job, trapped in a seemingly inescapable hell. The latter part was because his newly found lack of funds had made him homeless, and he was forced to reside in a cheap hostel. We're not talking about the romantic, movie-esque type of hostel homelessness where you ride your misfortune out in a barren room with suspicious stains on the walls. We're talking about a poorly built place that's full of rowdy Brits who want to fight you. That's half a step up from a particularly seedy prison at most, and even that's debatable because prisons tend to feature far less drunks.

Mr. Kaye described this particular circle of Dante’s Inferno as: "Drugs and alcohol were being abused regularly at the hostel, there were fights among people living there and the police turned up almost every other night. The rooms were small and private but doors would get kicked in by other people and there could be loud music blaring for hours. It was a tough time and every night you feel unsafe. It was a lonely and isolating time."

That ... seems like the kind of place that would drive you insane within a week. Mylo Kaye had to live there for 12 months.

And now he has a tiny dog sculpture. So suck it, universe.

Luckily, Kaye had a hobby to occupy his mind: He liked computers. He couldn't have one of his own in the hostel because even if he could afford one, someone would probably have puked on it within minutes. So he started hanging out at the local library, using its computers to claim his unemployment benefits and pass the time. As his interest in computers deepened (and, presumably, his hatred of his accommodations increased), he started taking local college courses to increase his skills.

As he kept passing his courses easily, he managed to get enough confidence to hit an unanticipated studying groove. This sent him on a self-improvement journey where he eventually applied to and got accepted at a university in Manchester. There, he met a like-minded business enterprise major named Jack Mason. They started spitballing ideas, and within a year, they left the fields of academia to build a company of their own. With a shoestring budget, they started making websites for small businesses and later moved on to mobile apps.

Today, Kaye is a wealthy businessman whose digital company Dreamr has won awards and boasts an annual turnover of over $1.27 million (and even more importantly, they have an official office dog called Chilli). However, he hasn't forgotten his year-long stay at the hostel of terrors: He's an active figure in various charities that fight against poverty and homelessness in the Greater Manchester area.

A Down-And-Out Cancer Patient Makes Himself A Sickbed Promise, Keeps It Like A Boss

Peter Loughrey was a daredevil kind of guy with what he readily describes as "a death wish." He had a dream of becoming a stuntman, because hitting L.A. and sucking up Arnold Schwarzenegger punches for money seemed like the thing to do with this particular mentality. Unfortunately, he soon learned about the sad realities of making movies, such as "waiting around," "safety harnesses," and "10,000 other hopefuls vying for the same jobs." The boredom and lack of work wore him down. Before long, he was homeless and flat broke, living in a van in Marina Del Rey. It was by no means a Dickensian nightmare -- Loughrey mostly lounged at the pool of a nearby apartment complex. Still, it marked an end to his dreams. Defeated, he called his parents, who set him up with a cozy job in marketing.

However, the world wasn't about to let this particular story end quite that easily. Karma is always listening when someone makes boasts of the "Yeah, I'm a crazy dude and I've got a death wish" variety, so his "this didn't work out quite like I planned" cake soon got a generous icing of ... nasty cancer.

As he was being treated for a rare form of lymphoma, Loughrey took a long, hard look at the turd sandwich life had unexpectedly shoved down his throat. He made a solemn promise to himself. If he would somehow defeat cancer, he'd become the best damn art dealer that he could be.

Then, he proceeded to beat cancer and become the best damn art dealer that he could be ... so hard that he became a millionaire.

"You hear that, cancer? Eat. My. Shorts."

To be fair, this didn't exactly come out of the blue. He had some art knowledge, gained from countless exhibitions and galleries his parents had dragged him to as a child. He'd also already dabbled in art business with his significantly less homeless brother, until said brother tragically died of AIDS. But despite death, tragedy, financial woes and memories of an imploded dream career, Loughrey persevered. He got married, invested $20,000 he really couldn't afford on assorted art that he (and only he) had a good feeling about. For years, he bled money to the point where his wife kept coming home and seeing that he had once again sold some of their furniture to keep his gallery running.

And then, in 1999, the Internet happened. Overnight, every kind of art freak across the globe suddenly had access to Loughrey's kooky exhibition. Within the last two decades, he's auctioned a ridiculous $100 million in art.

A Homeless High School Dropout Becomes A General And A High-Powered Executive

"A General, an Accenture executive and a poor, homeless high school dropout walk into a bar," sounds like the setup of a particularly bad joke. In reality, it's a perfectly accurate description of Linda Singh stepping into a watering hole.

Singh's early life had all the makings of a disaster. We're not even going to list all the crap that she had to go through in her formative years -- let's just say that if you can think of it, it probably happened to her (it's all pretty dark, but you can read the links). At the ripe age of 15, she was kicked out of the house by her less-than-exemplary parents. She got herself a job at Burger King and moved into a room. She kept it together at school, getting good grades and playing varsity basketball. However, she soon discovered that working a part-time service industry job wasn’t exactly paying the rent. So she ended up homeless. The combined stress from this and literally everything else in her life wore her down enough that her grades started dropping, adding school trouble to the mix. Finally, the long line of gut punches that had been her life ended with a kick to the head when she found she could not afford to take her SAT test. So she dropped out of high school.

Singh was now 17 and totally without prospects for future, but she had one thing going for her: She was used to juggling pretty much every problem a person can face, so she only needed to remove a few of her most pressing troubles to handle the rest like a boss. She took care of her housing and employment issues by joining the U.S. Army National Guard. And that's when things got a little hectic.

Because that uniform was getting heavier by the month.

Over the next 30 years, Singh focused her energy and finely tuned survivor instincts on ... absolutely everything at once, really. She served in Kosovo and Afghanistan, getting the Bronze Star and rising to the rank of Major General. Meanwhile, she picked up her studies and received a bachelor's degree, an MBA and a master of strategic studies from the U.S. Army War College. She's said to be working toward a doctorate as well. And because she apparently still had some excess energy, she also took up a second career in the Fortune 500 consulting company Accenture, where she worked for over 19 years in assorted high-ranking roles, including Managerial Director.

Because merely cramming three lifetimes' worth of accomplishments in as many decades of dual-careering and advanced studies just isn't enough, she also had to go and make history. Today, she's the Adjutant General of the Maryland National Guard, being the first African American and the first woman to hold the job. You might have heard about her during the 2015 Baltimore riots, which she was put in charge of controlling after just a few months on the job.

All the while, Singh has been perfectly open about her awful background, and freely brings up her past experiences as an underdog as a part of her leadership style. She likes to be pretty compassionate ... unless you're an underling who has been harassing others. In that case, she stomps down hard. In her own words: "I think [my history] allows me to come from a very different place, in terms of understanding what it means from the perspective of the victim. I think it also makes me very non-tolerant. I am not tolerant whatsoever to having that kind of behavior occur."

A Homeless Christmas Card Salesman Goes From Dickensian Poverty To A Billionaire

John Paul DeJoria was as homeless and down-and-out as you can be. We're talking "foster care background, living out of a car, selling Christmas cards door to door just to afford food" stuff, here. Dude was essentially just one Victorian English costume away from being a character in a Charles Dickens novel.

But years went by and he soldiered on. Christmas cards eventually turned into encyclopedias and shampoo. DeJoria learned a surprising amount of the latter while working for Redken and Fermodyl Hair Care, and when both companies ended up firing him, he felt that he might as well start his own. In 1980, DeJoria and his old friend, hairdresser Paul Mitchell, set up a company with only $700 between them. They started peddling their product to various salons and distributors, and ... yeah, well, if you know anything about hair products, the fact that DeJoria's partner was named "Paul Mitchell" might already have tipped you off about how it went for them.

Smoooooooth, baby.

The company was called John Paul Mitchell Systems. Yeah, that John Paul Mitchell Systems. If you've ever taken a shower, chances are that the shampoo that got in your eyes was made by them.

It was such a hit that it became a million-dollar company within its second year, and by 1983, the guys were building Hawaiian farms. In 1989, the company was already a massive player when Paul Mitchell unexpectedly died of pancreatic cancer ... which left DeJoria in charge of the company.

Today, John Paul Mitchell is still doing monster business, and the former homeless Christmas card salesman sitting in the corner office has an estimated net worth of over $3 billion, every bit of it self-made. Don't worry, though -- it doesn't all come from hair care products. It's not that lucrative.

Part of it is courtesy of Patron Tequila, a company that DeJoria also founded.

Like this article? Check out "5 People Who Won Big By Manipulating The System" and "5 Legendary Examples Of People Sticking It To The Man".

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