5 Wildly Successful Entrepreneurs Who ALMOST Gave Up on Their Dreams

In any business venture, you’re never going to get every decision right. You’re going to make mistakes, lose money, and experience setbacks. No one said entrepreneurship was easy.

But we’re here to tell you that while it’s not easy, entrepreneurship can still be an incredible avenue for you — failures and all. In fact, failures can often teach us the most important lessons that set us up for greater future success.

Don’t take it from us — take it from some of the incredibly successful entrepreneurs that have been featured on The School of Greatness. Every entrepreneur we’re highlighting today has had to overcome adversity at some point in their career, but they’ve found ways to adapt, overcome, and ultimately meet and exceed their professional goals. James Altucher, Nicole Lynn, Dan Lok, John Paul DeJoria, and Jamie Kern Lima are all successful entrepreneurs who have inspired, educated, and demonstrated how to overcome failure, and today, we’re taking a look at each one of their amazing careers so you can hear how to learn from your failures.

James Altucher: In Order to Succeed, You Must Fail

If anyone can teach us about the importance of failure in entrepreneurship, it’s James Altucher. This man is a LEGEND. Today, he’s a hedge fund manager, venture capitalist, prolific author (he’s published 20 books), and self-made millionaire. He’s a successful business owner living a life of financial freedom we all dream of, and as if all that weren’t enough, he’s a podcaster too!

But he wasn’t always so successful. Before becoming the titan of industry he is today, James lost everything. He started 20 companies, but 17 of them ultimately failed. He lost nearly all of his money; at his lowest, he had less than $200 in his bank account. He entered into a mental health crisis. Depression, anxiety, suicidal thoughts — James experienced them all, but he didn’t get defeated. 

We want to be clear — if you’re experiencing any of the mental health issues we just mentioned, of course, you should seek help. Counselors, therapists, and psychiatrists can make a world of difference when you’re battling mental health issues. However, with appropriate help, you can overcome your mental health problems and your worst failures to prevail in business like James did.

From his experiences with failure, James learned not to equate his self-worth with the amount of money in his bank account. It was a tough lesson — he’d worked hard and earned a lot of money, so it was a crushing blow when it all came tumbling down. But when James realized that money is just one aspect of this life and not the true source of his worth, he learned to approach business in a different way. He got creative, invested in companies he trusted, and built his bank account back up to where he wanted it to be.

In business, you will experience moments where you lose money, but that’s okay! The bottom line dollar amount your business is worth does not define you as a person. Instead, you are defined by your talents, relationships, and your actions. If you, like James, can get creative with your money and focus on using it toward your ultimate mission — your passion and your purpose — you can overcome any failure or loss.

Nicole Lynn: Your Purpose Is Your Superpower

When it comes to identifying your purpose and pursuing it with everything you have, there’s no one more inspiring than Nicole Lynn. Nicole has an epic purpose, which she calls her “super power” — representing young athletes in the NFL. Nothing lights her up more than helping new NFL draft picks find their way to success in the wide world of the NFL, and she is good at it. As a result of her incredible work, she is the subject and executive producer of a currently-in-production STARZ original series about her life as well as a successful author. But before you go thinking that Nicole’s living a charmed life, let us tell you — she has definitely overcome her share of failure and adversity.

As a child, Nicole’s biggest concern was whether or not she would have food for dinner. Money was hard to come by in her family, and Nicole spent her teenage years working and saving to afford the bus fare to attend the nearest magnet school. As a result, Nicole developed a lot of fear and anxiety around money — she worried about saving enough and achieving financial security.

Later, when she decided to launch her career as a sports agent, that fear carried over. In fact, for years before becoming an agent, Nicole worked as a lawyer because she felt it was the best path to financial security and she feared taking that risk to start a new career. Eventually, however, she knew she had to take a leap.

Nicole could have given up on her dream. She could have chosen to forget all about helping young athletes and instead stuck with her lawyer position, but she knew she had a purpose, and she chose to pursue it despite her fear. And we’re so glad she did! Nicole is serving and creating a massive impact on the world, and we know she wouldn’t have it any other way.

Dan Lok: Overcoming Imposter Syndrome

Have you ever heard the term “imposter syndrome?” Even if you’ve never heard it, we bet you’ve felt it at some point in your life. Imposter syndrome is when you feel like you don’t belong, or that you don’t deserve to succeed. It’s when you feel like you’re “faking it,” even though you’re working hard to reach your goals.

Dan Lok definitely knows what imposter syndrome feels like. As a young Chinese-American entrepreneur, he started company after company — 13 in a row — and watched them all fail. He lost money, time, and a lot of self-confidence, and suddenly he didn’t feel he belonged among the millionaires and successful businessmen and women he spent his time around. Even as Dan finally started to progress and build more and more financially successful businesses, he continued to feel a sense of imposter syndrome. That is, until he had a key realization:

As long as you’re comparing your financial success to those a step or two ahead of you, you’re never going to feel like you measure up. But when you realize that everybody is at a different stage of their entrepreneurial journey, imposter syndrome melts away and you’re free to keep striving toward your goals with confidence.

Think about when you experience imposter syndrome — who gives you that feeling of not being good enough? Has that person simply been in business for a little bit longer? If so, choose to focus on what you can learn from them instead of comparing yourself to them. You’ll be amazed at what you can discover when you push imposter syndrome out of the way and strive for greatness.

John Paul DeJoria: The Billionaire Mindset

You’ve probably heard the term “millionaire mindset.” It’s a popular buzzword, and it demonstrates that your mindset is one of the most essential tools you have for creating and building wealth and that it’s important to cultivate the mindset of a millionaire along every step of your entrepreneurial journey. However, this next fearless businessman inspired us to push that one step further.

John Paul DeJoria, co-founder of the Paul Mitchell line of hair care products as well as The Patrón Spirits Company, challenged us to surpass the millionaire mindset and go right to the billionaire mindset. As a self-made billionaire himself, we think he knows what he’s talking about.

Mind you, John Paul DeJoria wasn’t always in a position to be giving so much away. At the beginning of his career, John was literally living in his car and going door to door selling shampoo bottles. But even at that low point, John realized that the name of the game was service — he strove to provide his customers with such a strong product that they would want to come back for more.

That mindset has taken John far. Today, he owns multiple billion-dollar companies, and he’s one of the wealthiest individuals in the world. 

We encourage you to ask yourself — what is your mindset about money? Are you constantly worried about saving every penny? Do you toss and turn at night over your investments, afraid you’ve made a misstep? Or are you focused more on giving? Do you use your money and talents to serve others? According to John Paul, the billionaire mindset is all about what you give away.

Jamie Kern Lima: What to Do When You Hear the Word “No”

Jamie Kern Lima knows a thing or two about that word “no.” She’s heard it more times than we can count. On her journey to launch one of the world’s top makeup brands, countless retailers and investors turned her down. For years it seemed her small business would never take off and make it big-time, and Jamie experienced moments of self-doubt and worry that she would never succeed.

But did she give up? Of course not!

Over and over and over, Jamie persevered in the face of “no.” She got back up every time she found herself knocked down and she kept trying. We think it must have taken tremendous courage to keep going, but Jamie did it.

Jamie showed up every day for over three years, and finally, she heard her first “yes.” her products hit the shelves and her company took off in a big way. Eventually, Jamie sold her company, IT Cosmetics, for $1.2 billion, making her one of Forbes’ Richest Self-Made Women. We’d call that a success, wouldn’t you?

We understand how tempting it can be to give up in the face of another “no.” Once you’ve heard it enough times, it’s easy to feel like a failure. But the truth is, you’re only a failure when you decide you’re a failure! That means that even when you hear “no,” you can always choose to stand up, hold your head high, and keep striving for that life-changing “yes” that will launch you to where you want to be.

Is there a dream that you’ve given up on? Have you been working to launch a product or business or program that just hasn’t taken off yet? We want to encourage you to keep trying. Keep striving and showing up for yourself, your dream, and your passion every day. Just like Jamie, you’ll eventually hear your “yes,” and we’re sure you’ll be amazed at what new heights of success you’ll be able to reach.

You — Yes, YOU — Can Learn from Your Failures

It may sound crazy, but the incredible entrepreneurs we’ve talked about today aren’t so different from you. They’re normal people. They make mistakes, face challenges, and overcome adversity in many forms. However, they also keep striving for greatness, and they never give up in the face of failure. Rather, they learn what lessons they can and move on stronger, smarter, and better than ever before.

What’s your biggest, wildest dream? Do you want to start a business? Do you have an idea for a new invention? Are you ready to become an author, singer, athlete, or investor? Take the first step today, and even if you fall, commit to getting back up. With enough passion, perseverance, and purpose, you can be great, too.