5 Incredible Entrepreneur Success Stories That Will Inspire You to Hustle

You’re working hard trying to build your business every day…

But are you hustling?

Dreaming up a killer business idea is one thing. Putting that idea into action is a whole different story.

The entrepreneur’s journey can feel discouraging and lonely at times. Most people can’t relate to the uncertainty that comes with building something from nothing. Sometimes it’s hard to stay motivated when your friends are out having fun… while you’re grinding it out day after day, year after year until your efforts pay off.

Is it worth it?

Financial freedom, calling the shots, and being able to work on projects you love? Absolutely.

There will be highs, and there will be lows. As you’ll see in the inspiring stories below, how you navigate them is more important. It’s about hustling…and refusing to ever give up!

Rising from the Bottom to the Top

No matter how bleak your financial situation seems right now, you can turn things around.

You can rise from the ashes…and come out on top.

Don’t believe me?

Other incredible entrepreneurs have done exactly that. They’ve conquered obstacles like money problems, self-doubt, family drama, and anything else you can think of. If you’re willing to hustle and chase your dream relentlessly, there’s no reason why you can’t join them.

Check out some of these incredible rags-to-riches entrepreneur stories. They’re loaded with insights you can take and apply in your own business.

Get fired up. Get inspired.

And get ready to hustle.

5. John Paul DeJoria

John Paul DeJorgia of Paul Mitchell

When you’re so low that you look up and see ants walking over you, you can only go up.

John Paul DeJoria is the epitome of hustle.

He used to be in a street gang. He lived out of his car for a few months. He sold encyclopedias door to door and even picked up discarded bottles to cash in, because he was desperate to feed himself and his young son.


He’s a billionaire entrepreneur who founded John Paul Mitchell Systems hair products and the Patrón Spirits tequila company.

He came a long way from showering at a public pool every day and scrounging for the cheapest meals he could find at Los Angeles Mexican restaurants.

DeJoria built his empire from scratch by going door to door to beauty salons and persuading them to offer his products. He had no real connections… and only about 700 bucks. Now, Paul Mitchell Systems brings in about $900 million a year and Patrón brings in even more!

Key Insights for Your Business

  • Don’t be afraid of constraints. DeJoria started his hair products company with $700. And not just that. He did it in 1980, in a horrible economy where inflation was 12.5{583bae29b9e65f7174051f7da2852cce5e9273a6224d9fff4fde8e4359066c4c} and interest rates were 20{583bae29b9e65f7174051f7da2852cce5e9273a6224d9fff4fde8e4359066c4c}. This forced him to really pinpoint the essentials and bootstrap his business. He focused on just a few products and proved they were viable before trying to grow too quickly.
  • Remember the people who help you on the way up. DeJoria sometimes got free food from a Mexican food restaurant he went to all the time in the early days. They knew he was broke, and sometimes would give him free entrees. When he started making money, he went back and tipped them extremely well. Now he channels his generosity mostly through charities and other philanthropic organizations.
  • Get used to rejection. DeJoria overcame a ridiculous amount of rejection by sticking it out in door-to-door encyclopedia sales for 3.5 years, when the average employee stint was just 3 days. His advice: just keep knocking on doors. And smile just as enthusiastically on the 100th door as the first.

4. Sara Blakely

Sara Blakely

Photo Credit: Gillian Zoe Segal

My fear of regret is stronger than my fear of anything else. It gives me courage.

Sara Blakely’s success story had a humble beginning:

The year was 1998. She was selling fax machines door to door in Florida. At work, she struggled to eliminate annoying panty lines whenever she wore light-colored slacks.

Eager to solve her problem, she decided to cut the feet off pairs of pantyhose and wear them under her pants. That’s when the idea for Spanx was born. Blakely started working nights and weekends visiting manufacturers, researching patents, and developing a prototype.

Spanx exploded in 2000, when Oprah Winfrey (more on her in just a second) said she liked them better than regular underwear. Then Blakely appeared on a reality show with Richard Branson in 2004, who became a mentor and friend.

Since then, Spanx has developed into an Atlanta-based “shapewear” company of slimming and toning garments. The product line has expanded to over 200 items, including yoga clothes, jeans, and even undershirts for men. Blakeley’s company does about $400 million in annual sales, and in 2012 she became the youngest self-made woman on Forbes’ billionaire list!

Key Insights for Your Business

  • Solve your own problems first. The genesis for Blakely’s company came from solving an annoying problem – a problem that millions of women face. The focus wasn’t on coming up with something that would make a lot of money. That came as a byproduct of developing an effective solution. If you can be a problem-solver, you can be a money-maker too.
  • Face your fears head on. Blakely admits she hates flying and public speaking, which is really rough for a billionaire entrepreneur who has to travel all around the country. But she overcomes these fears by being grateful for the opportunity, by remembering all the other people who didn’t have the education or upbringing she had, and presses on.
  • Visualize your success. When she was selling fax machines, Blakely kept a journal and wrote how she wanted her life to change. She even wrote about how she wanted to invent or create a product she could sell that would be her own and make people feel good. When the idea came, she took it and ran with it.

3. Matt Mullenweg

Matt Mullenweg

Photo Credit: Chiku chu

It’s really hard not to be distracted by the things you think you should be doing, or that you see other businesses doing, and focus in on what actually matters to your chosen business day in and day out.

Matt Mullenweg went from a barbecue-loving college dropout in Houston to a founder of a billion-dollar San Francisco tech company, Automattic. His company developed WordPress, a free and open-source content management system (CMS) used by more than 60 million websites today.

Oh, yeah…

WordPress was initially released when Mullenweg was just 20 years old!

Mullenweg laid the foundation as a teenager, when volunteered some of his time coding for B2/cafelog (another open-source blogging platform used on a few thousand blogs at the time). One day the lead developer disappeared, and Mullenweg decided to jump in and fill the gap.

Today, WordPress powers around 19{583bae29b9e65f7174051f7da2852cce5e9273a6224d9fff4fde8e4359066c4c} of the top 10 million websites worldwide, including the New York Times, BBC America, and Tech Crunch.

Insights for Your Business

  • A relentless focus on growth. 99.9{583bae29b9e65f7174051f7da2852cce5e9273a6224d9fff4fde8e4359066c4c} of us would be thrilled if we created a platform used by millions of top websites across the Internet. But not Mullenweg. He’s obsessed about the others, and how to get them to give his platform a try. A philosophy he lives by: there’s always room to grow.
  • Focus on projects that align with who you are. Mullenweg describes how he eats, sleeps, and breathes WordPress. It’s not something he built; it’s who he is, and he couldn’t not work on it. That’s why it’s so important to pursue something aligned with your core values – the contributions you want to make to the world.
  • Follow your instincts. It’s easy to get wrapped up in the endless stream of business advice. Ultimately, it’s up to you to follow the beat of your own drum. Mullenweg makes decisions because he feels they’re right for his company… instead of worrying so much about what “everyone else” does. This led him to make WordPress open-sourced (the code is free to be developed by anybody who wants to contribute).

2. Oprah Winfrey

Oprah Winfrey

Photo Credit: hang_in_there

The big secret in life is that there’s no big secret. Whatever your aim, you will get there if you’re willing to work.

The deck was stacked against Oprah Winfrey from birth…

She was born into poverty in Mississippi to a teenage single mom. This began a string of tragedies when she was young. Winfrey was abused often – even raped – until she decided to run away from home.

Things got even worse from there. Winfrey got pregnant was she was 14, and her son died when he was still an infant. Nothing turned around until she got a job in the radio business. That led to an anchor gig for the local evening news when she was 19, which led to a daytime talk show. Once her talk show went national, Oprah was well on her way to building her own media empire.

Forbes went on to list her as one of the first African-American women billionaires in history.

Insights for Your Business

  • Be authentic. As a child, one of Oprah’s favorite things to do was to ask her dolls questions. She also loved to ask questions to the crows that sat on the fence of her family’s property. Winfrey was born to be a talk show host. You probably know, deep down, what you were meant to do too. Now’s the time to do it.
  • Surround yourself with the best people. Many people who associated with Oprah, like Dr. Phil, went on to become incredibly successful in their own right. Winfrey is very selective about whom she surrounds herself with because she believes they influence her successes (or failures) greatly. She looks for people who will stick with her whether things are good or bad.

1. Mark Cuban

Mark Cuban

Photo Credit: b_d_solis

Work like there is someone working 24 hours a day to take it all away from you.

It all started when Mark Cuban was 12 years old.

He wanted a pair of new basketball shoes more than anything in the world. But his dad refused… with one condition: if Mark worked to earn the money, he could get whatever he wanted.

Cuban didn’t need to hear it twice. He started selling garbage bags door to door shortly after, and his path as an entrepreneur was set.

Cuban sold his first company, MicroSolutions, for $6 million in 1990. He sold his second,, to Yahoo for $5.7 billion before deciding to buy the Dallas Mavericks. Now, he writes books, owns a film distribution company, and even has a gig on the reality show Shark Tank.

It wasn’t always easy. Cuban went through some very stressful times – even eating ketchup and mustard sandwiches (gross!) at one point when things were really tough. His solution? When things got tougher, he just worked harder until his effort paid off!

Insights for Your Business

  • There are no shortcuts. Cuban was always laser focused on what he could control: his effort. He suggests knowing your business and industry better than anyone else, loving what you do, and always be hustling to make things happen.
  • Be wary about borrowing money. Cuban thinks that 99{583bae29b9e65f7174051f7da2852cce5e9273a6224d9fff4fde8e4359066c4c} of businesses today can be bootstrapped and started without outside financing. It’s a matter of control. Staying debt free keeps you at the wheel. But when you take on too much debt, you have to worry about pleasing lenders and investors more than the people who should matter most: your customers.
  • Stop worrying about the risk. Just pay the cost of success. Massive success comes with a massive price tag to match in the form of time, effort, and other sacrifices. To Cuban, there’s no reason to worry about the risk because, if you want it enough and keep working to get there, you’ll find out how to get it.

Your Turn

Every entrepreneur faces unique challenges along their path to success. Your journey might be smoother than the massive successes above… or even rockier.

One thing’s for sure, though. If you want it badly enough – if you pay the price of success – you’ll find a way to get it.

It’s time to stop daydreaming and worrying, and start doing something about it.

It’s time to do what the most successful entrepreneurs in the world do: