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The risks of entrepreneurship: 3 lessons from famous founders

Posted by Carol Mahamedi

December 27, 2022

Looking for encouragement as you navigate the risks of entrepreneurship? These three incredible lessons from famous founders who overcame their own unique challenges will inspire you to study harder, chase faster, and be braver— at every stage of your entrepreneurial journey.

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1. Oprah Winfrey: Always be prepared


Back in the early 1980s, if you had told Oprah Winfrey that her big break was just around the corner, she probably wouldn’t have been surprised. After all, she’d been preparing for it for years!

At the time she was discovered, Winfrey was working at her local news station as a co-host. When a major Chicago TV station came across footage of her hosting, they invited her to audition for a live cooking show.

Though Winfrey had no experience with cooking shows, her practice and dedication throughout her news career prepared her for this lucky break.  After excelling in that interview, the station gave Winfrey her first lead hosting opportunity on the show “A.M. Chicago.”

Within one month, it became the most popular local show in Chicago— and would soon be rebranded as “The Oprah Winfrey Show.” Winfrey went on to become one of the most famous, award-winning daytime television show hosts of all time, earning 47 Daytime Emmy Awards over the course of her show’s 25 seasons.

Between that success and the launch of her Oprah Winfrey Network, she has built a net worth of over $3.5 billionThe lesson in Oprah Winfrey’s success story?

Learn everything you can in every season you find yourself in. Whether your startup is growing or shrinking, early or mature, or still in the ideation stage, the lessons you learn through each of these experiences are invaluable preparation for the risks of entrepreneurship you’ll face in the seasons to come.

“I believe luck is preparation meeting opportunity. If you hadn’t been prepared when the opportunity came along, you wouldn’t have been lucky.”

— Oprah Winfrey

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2. Steve Jobs: Chase what you love, not the money


Back in 2007, at the All Things Digital conference, a member of the audience asked Steve Jobs for his best piece of advice for aspiring entrepreneurs. In typical Jobs fashion, he answered simply: Love what you do. 

Throughout his childhood, Jobs and his father worked on electronics in the family garage. As the two tinkered on dozens of small electronics projects, Jobs developed a love of technology, mechanics, and computer design. Those lessons became the foundation he built Apple on just a decade later. 

Though Apple faced difficult times, particularly in the 1980s when IBM computers outpaced Apple’s original Macintosh, Jobs’ passion for innovative technology steadied the company. The way Jobs saw it, success requires perseverance, and the only way to keep persevering in the long-term is to truly and deeply love what you do.

Creating a profitable business requires sacrifice, time, and focus. Challenges will threaten your success, competitors will narrow your market share, and shifting trends will force your company to continually redevelop.

Complacent, apathetic and unenthusiastic entrepreneurs will be driven to quit. But the ones who chase what they love will push through the challenges because they’re motivated by passion— not money. 

“The only way to do great work is to love what you do.”

— Steve Jobs

3. Barbara Corcoran: The only way to conquer your fears are to push through them


Barbara Corcoran is a best-selling author, Shark Tank host, founder of The Corcoran Group, a real estate brokerage in New York City, and a self-made millionaire several times over. And despite her success, she’s far from immune to the fears every entrepreneur faces. 

By the time Corcoran launched her real estate brokerage, she had held 22 different jobs in a variety of industries, but no job captured her attention. In 1973, she borrowed just $1,000 to launch her first company, The Corcoran Group— which she would later sell for $66 million. 

On the surface, it seems like Corcoran has fearlessly faced every stage of her growth journey. But she’s the first to admit that throughout her journey, fear of failure, fear of judgment, fear of not knowing enough and fear of public speaking nearly derailed her progress.

Instead of letting these fears stop her from pushing forward, Corcoran made a habit of facing each fear head on. When she was afraid of failure, she jumped anyway. If fear of judgment slowed her down, she ignored the voices. Instead of avoiding public speaking, she signed up to teach a real estate class. 

There’s no question, the risks of entrepreneurship are intimidating. But Barbara Corcoran is proof that every fear can be overcome, and the things you dreaded the most can become your superpowers — as public speaking became for her. 

“The biggest challenge in business is not the competition, it’s what goes on inside your own head.”

— Barbara Corcoran

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