Dan Waldschmidt

by Dan Waldschmidt

October 23, 2017

11 Massively Successful People Who Were Homeless Along The Way.

We all have those well meaning friends who, like it or not, always try to make light of our desperate situations. “It’ll get better.” “You have to keep trying.” “You always land on your feet.” “The grass isn’t always greener.” “It could be worse.” “Tomorrow is a new day.”

And you love your friend, but you just want to say, “Hey, do me a favor and take your positivity and shove it somewhere. I’m sulking over here.”

It’s no secret that times are tough. The pursuit of success is no easy conquest. And that journey can be even tougher when you don’t know how you are going to keep the lights on or how you are going to afford to keep the doors of your business open. 

Times do get tough. But not just for you. It is that same way for every successful person. That annoyingly positive friend of yours is right. The only option for you is to keep going. Tomorrow is a new day.

And just in case words of wisdom aren’t inspirational enough, here are 11 people who had it tough, just like you, in pursuit of their dream.

1. Tyler Perry

Everybody loves Madea, but before she came bursting into our hearts with her witty one liners and pistol-toting shenanigans, her creator, Tyler Perry was sleeping in his car and living in pay-by-the-week motels in Atlanta.

He spent the $12,000 he had saved up from working to pay for the production of a play that he knew was going to be a hit. But it wasn’t. He lost all his money and his house. For the next 6 years, he lived like a nomad while he kept making plays. Putting on a play each year and just getting by until something finally took off and created the well known “Madea” series and other hits like “Why Did I Get Married,” and “Meet the Browns. 

Since then, he has generated $774 million in movie sales. 

2. Suze Orman

She wasn’t born a financial guru. Suze Orman worked her way from the ground up, just like the majority of us have to. After college, when she decided to move from Chicago to Berkley, California, the cost of living was more than she could pay–considering she moved to Berkley with her van, but no plan.

Caught in traffic one day, she got out to inquire about the mess and ended up getting back into her van with a job. She would live in the van for a few months while she and a friend saved money to get a place. Within ten years of moving to California, Suze Orman was the Vice President of Investments at Prudential Bache Securities.

And just a few years after that, she started her own investment company. Her financial companies are currently worth over $35 million now.

3. John Paul DeJoria

Founder and CEO of John Paul Mitchell Products and Patron Tequila was not always a billionaire. He went through rough times like a regular person. Having divorced his wife, he found himself living in his car and frequenting restaurants that specialized in $.99 meals — just to be able to eat for the day.

When he decided to partner with the late Paul Mitchell, they were quickly hertbroken when their million dollar investor backed out at the last minute. Believing in their product so much, the two invested the last $700 they had to buy product for their company. The investment paid off. In billions of dollars.

Today, John Paul DeJoria never has to worry about not being able to pay his bills and he’s got plenty left over for the 150 charities he donates to annually.

4. J.K. Rowling

Single parenting and living in a tiny apartment with no “real”  job, JK Rowling found herself living on public assistance and contemplating suicide from the depression that hovered over her daily. Despite her financial discomfort and feeling like a complete failure in life, Rowling kept working on the book idea that came to her a couple years earlier while she was riding the train to a temp job.

After finishing the book, having to scrounge for pennies and meals while she wrote it, JK Rowling sold “Harry Potter and the Philosopher’s Stone.” She has written 6 more subsequent Harry Potter books and made an estimated $1 billion on the series.

5. Chris Gardner

You may have seen the movie based on a small chapter of his life, The Pursuit of Happyness. Before Chris became the self-made millionaire he is today, he spent many nights on the streets and in the local homeless shelter with his three-year-old son, not knowing how he would feed his son dinner. Thankfully, his son had eaten at the daycare he was barely able to afford.

One day, he saw a man driving an expensive Ferrari and asked him a few questions that ultimately landed him an entry-level position at a financial company. He worked his way up and out to open his own company within ten years. You can read more of that story here.

6. Jewel

Making her musical debut 1995, Jewel was one of the first artists to be vocal about having lived on the streets. She lived in her car for the year prior to her big break. She was also very vocal about why. She got fired from her job for refusing to sleep with the boss.

After getting fired, Jewel decided that she would rely on what she loved — and started singing at a local coffee shop. After gaining quite a local following, Jewel made and released an album which quickly gained her 3 spots on the top 100 billboard charts and made her a millionaire.

7. James Cameron

While directing a very low budget horror film in Italy, James Cameron came down with an illness and came up with an idea for a screenplay — thanks to a few feverish nightmares while ill. After the film flopped, Cameron found himself back home in the United States with no home to call his own.

He couches surfed with friends and slept in his car while he was fleshing out the sci-fi feature that would he would eventually sell for a meager $1 just so he could direct it. The film, Terminator, ended up grossing $78 million.

He would go on to create a $6 billion movie portfolio.

8. Oprah Winfrey

Oprah Winfrey spent her whole life in poverty. She was born to a teenage mother who couldn’t provide for her financially — so she lived with her grandmother who was also poor and could not afford to dress Oprah at times. She would have to wear potato sack dresses.

When she was 6, she moved back to her mother. Her mother worked all the time and left Oprah with uncles and other friends and relatives. By the age of 9 Oprah had been molested by more than one caretaker while still barely being provided for.

When she became a teenager, she made the choice to move with her father, where she finished high school, started college and then eventually dropped out to pursue a career in television.

She landed a job at a morning show that didn’t pay very well, but it was a job that made Oprah Winfrey happy. That show eventually got renamed The Oprah Winfrey Show and started Oprah’s uphill climb to the $3 billion empire she has built.

9. Ralph Lauren

Ralph Lauren grew up dirt poor in the city of New York. His parents were both immigrants and his original last name was Lifshitz. He spent his high school days getting made fun of for that last name. So much that he eventually quit school and joined the army.

When he finished his army career he ended back in New York City. He was barely able to pay his bills on the meager salary of the retail job he worked. He had a keen eye for menswear and didn’t understand the drab boring ties that were regularly sold.

He redesigned the men’s tie, sold his idea to Bloomingdale’s and went from minimum wage to making $500,000 in one short year.

10. Hilary Swank

Actress Hilary Swank, best known for her roles in the box office hits Boys Don’t Cry and Million Dollar Baby started her life off meagerly, to say the least. She had dreams of being an actress from the time she was 8 years old. She grew up in a dysfunctional, poor, and unhappy home until her parents divorced when she was 14.

In full support of Hilary’s dreams, her mother loaded up their car and drove her daughter from Washington to California where they lived in the car going from audition to audition and taking odd jobs until they saved enough for an apartment. Hilary landed small acting roles until her big break in Boys Don’t Cry. Hilary Swank is now worth an estimated $40 million.

11. Steve Harvey

Steve Harvey knew in his early thirties that comedy was his calling. Then life came in and swept the funny right out from under him. After divorcing his wife, a couple cancelled gigs caused him to become homeless. Harvey lived in his 1976 Ford Tempo.

He said living in his car for a week was terribly hard. He had to do it for three years. He lived on $75 a week after having to send the rest of his money to his ex wife to take care of his sons.

He would shower wherever he could find running water and sometimes he got lucky and would be put up in a hotel when he had a comedy gig. He finally got his big break when he performed at the Apollo and has been on the big screen ever since and now lives in a 5 story mansion in Atlanta.

Steve Harvey is worth more than $140 million.


Hopefully you won’t have to be homeless to achieve the success you so desperately want for yourself.

But if you do — if that is what it takes — may these people be an inspiration to you.

Rags to riches is an age old story. And if stories are what you need instead of words of wisdom, you only have to look as close as your favorite famous person to find someone who has been where you are or worse.

If they could do it, so can you.

About the author

Dan Waldschmidt

Dan Waldschmidt doesn’t just talk about leveling up. He’s obsessed with it. He's set records as an ultra-runner and been the personal strategist for the leading business leaders of our time. He wrote a book, called EDGY Conversations that accidentally became a worldwide bestseller and continues to share his insights from the stage as a keynote speaker and on the blogs and podcasts you will find here. Most days, you'll find Dan heads-down, working on breakthrough strategies for his clients at EDGY Inc, a highly-focused, invite-only, business strategy execution company based out of Silicon Valley.