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Famous Entrepreneurs and What Small Business Owners Can Learn From Them

10-minute read

Emily Thompson

Emily Thompson

10 August 2022

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Here’s an interesting thought. At one time, some of the most famous entrepreneurs were just regular business owners, like you and me. They had a vision, pursued it with drive and determination, and became wildly successful. But none of that happened overnight.

In fact, for many of them, it likely took years of persistence, risk-taking, adaptability, and other key qualities to build their businesses from the ground up. As business owners, there’s a lot we can learn from their fortitude. Here, I’ll share the stories of six of my favorite entrepreneurs — and cover what we can learn from each of them.

How to Show Entrepreneurial Spirit: What Skills It Takes to Run a Business from Famous Entrepreneurs

Sara Blakely Bio, Founder of SPANX®: Persistence

In addition to building SPANX®, a $1.2-billion shapewear business, Sara Blakely was named the 93rd most powerful woman in the world by Forbes magazine in 2014 and in Time magazine’s “Time 100” list of the 100 most influential people globally in 2012. To say she’s successful is a massive understatement. Sara Blakely boasts a rags-to-riches story, having become the world's youngest female self-made billionaire in 2012.

Her roots are humble, however. After graduating from Florida State University, she spent three brief months working at Walt Disney World before becoming a salesperson and sales trainer at the office company, Danka. During that time, Blakely went door-to-door trying to sell fax machines, while sporting her required office attire, pantyhose.

One day, she cut off the feet of her pantyhose, in an attempt to appear more fashionable in open-toed shoes. The end result was a new product — one that would help her figure appear shapely without the discomfort of footed hosiery. And behold, one of women’s most popular shapewear products, SPANX®, was born.

But Blakely’s big idea didn’t get off the ground right away. She spent five long years cold-calling manufacturers and department stores, and receiving “no” after “no” to her product.

Finally, two daughters of a hosiery mill manager saw the light. They realized the need for the product and pushed their father to say yes to manufacturing SPANX®.

Soon after, Sara received her biggest break when Neiman Marcus began selling the shapewear, and Oprah Winfrey named SPANX® her favorite product of the year. Finally, Blakely’s incredible persistence had paid off.

If you’re considering throwing in the towel, even after years of hard work, think again. In interviews, Blakely mentions frequent dinner-table questions with her father about failure. He did this, she says, not to make her feel bad but to show her the motivating power of trying (and not always succeeding) at new things. It became the foundation for her persistence.

Persistence is one of the key skills to entrepreneurial success. To keep your persistence and will to succeed at an all-time high, try these techniques:

  • Skill: Let rejections be a source of motivation. When people say, “no,” they can light a fire within you that pushes you to improve yourself and work towards success. Try to prove your naysayers wrong, and persevere.
  • Skill: Stay committed, no matter what. Sometimes, it’s enough to make a promise to yourself. If you tell yourself to stay committed, no matter what happens, you’re more likely to follow through.
  • Skill: Be creative and willing to pivot. You may need to adjust your idea to be successful. Stay persistent, but be willing to embrace creativity and make tweaks when needed.

The truth is, most great businesses don’t become successful overnight. It takes lots of thinking and hard work from the start, along with determined persistence to handle the rejection and self-doubt. Hang in there and keep pushing ahead. If you have a good idea, and there’s a market for your product or service, your persistence will likely pay off.

Richard Branson’s History, Entrepreneur & Founder of the Virgin Group: Passion

The Virgin Group started out selling records from classified ads and went on to become one of the most influential record labels in the industry with an artist roster that included the Sex Pistols, The Rolling Stones, the Spice Girls, and Taylor Swift.

But since its 1970 inception, Richard Branson has expanded the company to multiple sectors, including travel and leisure, health and wellness, entertainment, telecommunication and media, financial services, and even the space industry.

While every one of Branson’s companies operates differently, a single characteristic unites them all — they were founded with passion.

According to, Branson says, “You need to inspire your staff when you launch a company, and you need to help them believe in your vision for the future. When you believe in something, the force of your convictions will spark other people’s interest and motivate them to help you achieve your goals. This is essential to success."

Branson admits he hasn’t been extremely passionate about every one of his businesses, but he has found a nugget within each of them that ignites excitement and plays to his skills.

For example, Branson doesn’t have incredible passion for the financial industry, but he does care deeply about customer service.

Upon launching Virgin Money in 1995, he felt passionate about serving people and disrupting an antiquated banking industry. This was enough to help motivate his team and bring them together behind a common goal.

While skills are something you can develop, passion is something that comes naturally from within. If you’re not passionate about your business idea now, ask yourself why you’re still pursuing it. Is it to earn money? Achieve fame? Something else?

The bottom line: If you’re not passionate about your business idea, you’ll likely have a long, uphill battle ahead. It may be difficult to manage the struggles and stay motivated during challenging times. Chasing money may not be enough to keep you focused and resilient during challenges.

Instead, look at your current passions and try to find a business idea. Ask yourself:

  • What are you really good at?
  • Is there an injustice that makes you angry?
  • Where does your mind wander when you have downtime?
  • What brings you the most joy?
  • What’s the one thing you’d like to be known for?
  • Is there anything you’d like to change about the world?

These are just starting points for finding your passion, which is a key ingredient of business success. Without passion, you can easily become distracted, unimaginative, or apathetic when challenges arise.

There’s a saying from dogsled racing that the speed of the leader is the speed of the pack. If you’re leading with passion, it’s much easier to inspire teams to rally around your vision.

Facts About Oprah Winfrey, television personality, actress, and entrepreneur: Creativity

She’s an Academy Award winner, 10-time Daytime Emmy Award winner, Golden Globe winner, 12-time NAACP Image Award winner, Peabody Award winner, four-time People’s Choice Award winner, and a recipient of the Presidential Medal of Freedom. Say hello to America’s favorite television personality, Oprah Winfrey.

But how did Oprah build her business?

A true rags-to-riches path, Winfrey landed her first job in radio during high school, and by age 19, got promoted to co-anchor at a local news station. The networks quickly realized her extraordinary personality and directed her to daytime television, where she turned the struggling morning show, A.M. Chicago from the lowest-rated talk show in Chicago to the highest-rated one. It would later become The Oprah Winfrey Show.

She also was one of the first television hosts to place a focus on self-help solutions, literature, and the sharing of one’s emotions. She garnered the attention of millions across the country throughout the 1990s by conducting personal interviews with celebrities and relating to her audience in unprecedented ways.

Winfrey boasts a one-of-a-kind personality — genuine, outspoken, and tender-hearted. In a strategic, but also incredibly creative way, she ties her content back to a relatable human experience. And it has been her recipe for television success. When studying Winfrey, it’s easy to see how critical creativity is for entrepreneurship.

  • Skill: Read and research as much as possible. Read voraciously to gather ideas you find appealing and noteworthy. Save them for reference in a notebook, on a bulletin board, or even on Pinterest. Read your old notes and develop them into fully thought out ideas.
  • Skill: Take a break and brainstorm. Let your mind wander for a bit. Go for a walk and get fresh air. Doing so can rejuvenate your brain and spark new ideas.
  • Skill: Be positive and avoid saying “no.” When you’re first brainstorming, no idea is a bad one. Write down every new idea, and narrow your list down later.
  • Skill: Avoid perfectionism. When you aim for perfection, you don’t give yourself room to be creative. Instead, let go of mistakes or imperfections, and focus on big ideas.

You also may discover you’re more creative when you’re in nature, feeling calm, or doing an activity you enjoy. Pay attention to when and where you’re most creative, and then be intentional about generating more creativity.

Interesting Facts About Jeff Bezos, Founder and Executive Chairman of Amazon: Risk-taking

Back in the early 1990s, the idea to start an online bookstore was crazy, let alone leaving a successful career on Wall Street to do so. But that’s exactly the risk Jeff Bezos took — and it paid off.

Today, Bezos is the third wealthiest person in the world. His company, Amazon, is a global leader and one of today’s most valuable brands. Bezos even funded Blue Origin, allowing him to travel to space in his own rocketship in 2021. Talk about a true risk-taker!

Bezos had many of the entrepreneurial qualities on this list, but he also had tremendous courage. After all, he envisioned an e-commerce company at a time when one didn’t really exist. People weren’t doing most of their shopping online, accumulating box after box on their front doorsteps.

Yet Bezos believed he saw many opportunities where he could create a company that would transform how people purchase products and capitalize on convenience. In the end, he was right. How many of us turn to Amazon first to shop for something we need?

Remember, big risks can sometimes pay off with big rewards. But it can be scary to take a leap or put your savings or even more on the line. Fortunately, there’s a way to take calculated risks that can potentially help your business be more successful and soften the blow if things don’t work out.

For example, try:

  • Skill: List the pros and cons of a business risk. This can help you see if it’s truly worth it.
  • Skill: Manage fear. Prepare for, but try not to focus too much on the worst possible outcome. After all, it might not happen, and your anxiety can hold you back.
  • Skill: Seek advice from others with experience. It’s important to have business mentors. Think of these people as resources you can draw upon, they are people who may have experienced similar success and can help guide you through tough choices. They should be honest and able to negotiate calculated risks with you.

Above all, consider the benefits of taking the right risks. Without pursuing any risks, you’ll have a harder time moving your business forward. Sometimes it’s worth it to dive into the deep end.

Bio of Martha Stewart, Founder of Martha Stewart Living Omnimedia: Adaptability

America’s favorite homemaker has experienced her share of twists and turns. But she’s been able to best each negative experience by adapting and reinventing herself throughout it all. Some of the hardest experiences include serving time in prison for conspiracy, obstruction of justice, and making false statements in relation to insider trading.

Talk about overcoming big obstacles!

Stewart worked a career on Wall Street until 1972, when she moved to Westport, Connecticut, where she purchased and restored a 19th-century farmhouse. Then she dedicated her time to mastering Julia Child’s recipes and creating a successful catering company. Quickly, Martha Stewart, Inc., grew to a $1 million business, hired by large corporations and celebrities.

At this point, Stewart adapted to the growing needs of her customers. She began churning out content related to her cooking career such as best-selling cookbooks and magazines before launching a hit television program in the 1990s.

But Stewart’s success came crashing down in 2002, when she was accused of insider trading. Later in 2003, she was convicted of conspiracy, obstruction of justice, and making false statements.

Stewart served five months in prison, where she mentored other women who learned from her about communication, leadership, and entrepreneurship — talk about adapting to and coming to terms with an uncomfortable situation!

Upon release in 2005, Stewart announced she would launch two new programs, including a daytime talk show and a reality TV series, similar to The Apprentice. Since then, she has continued to grow her brand in varying directions, from magazines to TV appearances to home and lifestyle products.

What can we learn from this controversial entrepreneur and homemaker? Adaptability is one of the key skills to business success. After all, we never know what challenges we’ll face as business owners, so it’s critical to pivot and adjust to whatever situation comes our way.

To become more adaptable, try:

  • Skill: Focusing on learning and personal development. The more you know, the easier it can be to adjust to changing circumstances. Stewart sees this as a key to her success. "You should never retire; you shouldn't even use the word," Stewart says. "It implies going off into the sunset, and who wants to do that?"
  • Skill: Embracing new technologies. To be a successful entrepreneur you have to accept that we live in a world that relies on technology. Get to know the technological solutions in your industry, and see if they can help you gain a competitive edge.
  • Skill: Being open-minded in how you operate. Try hiring someone who’s different from who you’d normally pick. Be open to adjusting your business plan to a changing marketplace. Don’t get pigeon-holed into following the same procedures over and over. Instead, embrace changes and view them as beneficial.

Adaptability is an important quality, not just for your business, but throughout life. If there’s one thing that’s constant, it’s change. The more you’re able to adjust, the better off you’ll be.

Insuring Success

As you can see from the stories of these entrepreneurs, it’s rare to become a business success overnight. More often, it comes after a considerable amount of hard work. And that last thing you probably want is for anything to happen to your business after all that effort and investment.

That’s where business insurance can help. Whether it’s general liability, professional liability, workers compensation, or some other type of policy, having the coverage you need can financially protect your business from a variety of risks.

We know that adding more to an already full plate is not what a new business owner needs. So, we’ve made it fast and easy to get covered.

Just spend a few minutes online, or with one of our licensed insurance pros on the phone, and we can help find affordable coverage from among the nation’s leading insurers. We’re here at 844-654-7272, Monday - Friday, 8am - 8pm (ET).

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Success One Step at a Time

One thing all of these famous entrepreneurs have in common is that they didn’t become famous, or successful, overnight. Adopting these traits and developing these skills is certainly something to consider, but it’s not always easy. If it were, everyone might be a famous entrepreneur.

Opportunities are out there but it takes more than luck to seize them. You must be willing to put significant time and effort into your business, and your own professional growth to help build your vision.

We also get that it can seem a bit overwhelming to try to make big changes all at once. One solution? Choose one characteristic at a time and focus on developing it until it becomes part of how you operate your business.

Self management is key here; don’t be afraid to take some time to stay persistent, find your passion, become more adaptable, or explore taking risks. As these famous business people have proven, it can potentially pay off nicely in the long run.

Emily Thompson

Written by

Emily Thompson

I earned a B.A. in Journalism from the University of Wisconsin at Madison (go Bucky). After realizing my first job might involve carrying a police scanner at 2 am in pursuit of “newsworthy” crimes, I decided I was better suited for freelance blogging and marketing writing. Since 2010, I’ve owned my freelance writing business, EST Creative. When I’m not penning, doodling ideas, or chatting with clients, you’ll find me hiking with my husband, baby boy, and 2 mischievous mutts.

Emily writes on a number of topics such as entrepreneurship, small business networking, and budgeting.

This content is for general, informational purposes only and is not intended to provide legal, tax, accounting, or financial advice. Please obtain expert advice from industry specific professionals who may better understand your business’s needs. Read our full disclaimer

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