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From Failure to Success: 5 Entrepreneurs Who Overcame Big Obstacles (and How You Can, Too)

  • May 23, 2017
  • Written by Community Futures Saskatchewan

As with any career, the life of an entrepreneurs has its ups and downs. There are times of self-doubt and burnout, and moments where small business owners feel as though there aren’t enough hours in the day (tip: use these productivity-boosting tips and time hacks). Push past these challenges, though, and entrepreneurs can find themselves with profitable companies and fulfilling careers.

Just take a look at these five now-famous entrepreneurs who overcame significant failures! Then, emulate their habits and mental strategies to guide your small business to success as well.


Today one of the wealthiest people in the world, Ellison didn’t start on a promising note. He dropped out of two different universities—one of those occasions due to the death of his adoptive mother—and bounced from job to job before co-founding Software Development Laboratories (later renamed Oracle Systems Corporation).

While the company initially made money, poor business practices nearly resulted in its bankruptcy at one point. Ellison had to resort to putting his home on the line to finance Oracle! The gamble paid off and both he and the corporation are now worth billions.

Key Takeaway:

Even the world’s biggest companies have had periods of intense struggle. However, believing in their ability to bounce back and focusing on helping their customers pulled them through. Understand that challenges are inherent in the process of building a business and don’t let self-doubt sabotage your dream of entrepreneurship.

Tip: Define your mission, vision, and values from the get-go, so you can always refocus on why you chose to become an entrepreneur during tough times.


Though Vera Wang is one of the world’s top fashion designers, early on her dream was actually to become a world-famous figure skater. When she failed to make the U.S. Olympics team, she was forced to find another life path.

After working with Ralph Lauren and Vogue (where she was turned down for the editor-in-chief role), Wang stepped out on her own and began designing bridal wear. She eventually expanded her empire and became one of the most sought after designers for everything from evening gowns to housewares.

Key Takeaway:

Being flexible is a necessity for entrepreneurs. Things are not always going to go according to plan but there is always another way to reach your business goals. For instance, if you’re struggling to find the funding to start or expand your company, contact your regional Community Futures office to discuss a small business loan that is tailored to your specific needs.


You have most likely heard of Dyson vacuum cleaners—that is because Sir James Dyson didn’t take no for an answer. He spent years developing the iconic bagless Dyson vacuum cleaner that would eventually make him famous, even after major manufacturers refused to distribute it. Dyson kept tinkering and opened his own manufacturing company, ultimately developing more than 5,000 failed prototypes before landing on the right design, which became the fastest-selling vacuum cleaner ever made in the UK.

Key Takeaway:

View every failure as a learning experience rather than a reason to quit, and then use that knowledge to make your products or services even better. As Dyson likes to say, “Enjoy failure and learn from it. You can never learn from success.”


The visionary behind the wildly successful KFC restaurant chain, Colonel Sanders had a string of failed business ventures behind him by age 65. He traveled the U.S. attempting to sell his chicken recipe to restaurants, often sleeping in his car. The hard work slowly produced results and in 1964, at the age of 73 years old, he sold the Kentucky Fried Chicken corporation for millions.

Key Takeaway:

Anyone can be an entrepreneur, no matter their age or life circumstances. At Community Futures Saskatchewan, our ELEVATE business program helps youth and adults with disabilities or health conditions start small businesses. Read a few ELEVATE success stories here.


American businessman Dave Ramsey lost millions of dollars by the time he was 26. When his real estate brokerage borrowed large sums on credit and creditors came to collect, he was forced to declare bankruptcy and shutter his company.

The disaster prompted Ramsey to learn everything he could about financial security and led to his later career as a bestselling author, radio host, and motivational speaker focused on financial topics. Today, he spends his time helping others get out of debt and lead financially healthy lives.

Key Takeaway:

Sometimes your biggest weaknesses can become your greatest strengths. In Ramsey’s case, he transformed his experience with mismanaging money and declaring bankruptcy into an opportunity to learn about what he did wrong, later turning this newfound expertise into a profitable career. Follow his model and leverage your weaknesses as well as your strengths in order to become a balanced, successful entrepreneur.

Inspired by these stories to go out and accomplish your business goals?

Download the Ultimate Goal-Setting Guide for Entrepreneurs and get started today!