Never say never: 6 entrepreneurs who failed before they succeeded

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I was talking about starting businesses with a friend of similar age recently and they were sharing about feeling defeated. They explained that they had a goal of starting a business in 2017 but failed at a certain aspect of it and feel that it’s too late in the year to start now. I discussed with them how we are only about one-third of the way through the year and that even if we were at the end of the year, that it is never too late to start. We also discussed how failure is a part of life and of business and that we learn, make corrections, and move on.

This conversation reminded me of many entrepreneurs who failed but didn’t let it stop them. The entrepreneurs learned from their failure, made changes and kept moving forward. Failure doesn’t define people, it’s how we respond to it that matters.

Jay Z is a phenomenal success but it wasn’t always that way. When he started, no major record label would give him a deal so he and a friend started selling his CDs out of his car. He is now one of the reigning kings of rap, owns his own record label, clothing line, and movie production company. He didn’t let the nonbelievers win – he kept going no matter the odds.

Mark Cuban – known mostly as the owner of NBA’s Dallas Maverick’s and as a “Shark Tank” investor, (the show’s only billionaire judge) – has had many failures. In an interview with Entrepreneur Magazine, Cuban says that he’s gotten fired from “more jobs than most people have had.” He also recounts failing to close several key sales deals, having had his credit card rejected and cut up while on a date, and that he has opened and closed more businesses than he can count.

Simon Cowell, the former American Idol judge, speaks of his many failures, including the failure of his record company. He told The Daily Mail that his biggest failures came when he believed his own hype. Cowell talks of signing bands that didn’t work and his record company going bust. But even after momentous losses, Cowell picked himself up and has become one of the biggest forces in reality television and his X-Factor format has resulted in discovered artists selling over 150 million records worldwide.

Steven Spielberg, who brought us such movies as Jaws, Shindler’s List, E.T., Indiana Jones, Jurassic Park, and Saving Private Ryan, and companies such as Amblin Entertainment and DreamWorks, was rejected by his first-choice film school, University of California, (USC), School of Cinema Arts, twice. The school apparently didn’t see potential in the young Spielberg, which is okay because he still got to show it to the world because he never gave up.

Bill Gates, founder of Microsoft and who is said to be the richest person in the world, had his first company fail. The company, Traf-O-Data, had the objective of reading the raw data from roadway traffic counters and create reports based on the information. But the first demo didn’t work, which ended the company’s bid to sell the processing service. Paul Allen, Gates’ business partner, says that the failure actually prepared the pair to make Microsoft’s first product. Neither Gates nor Allen gave up and because of it Microsoft was born.

Richard Branson, founder of the Virgin Group, failed to get good grades in school, (he was considered a pretty bad student and did poorly on standardized tests), because of dyslexia. After constantly struggling with his studies, Branson dropped out of school at the age of 16. Instead of letting his Dyslexia or failures define him, he started his first business, a youth-culture magazine called Student. From there he began a mail-order record company called Virgin to help fund his magazine. The business grew to a record shop, a recording studio, and eventually a record company, which struggled financially so was sold in 1992. Even after the failure of the record label, Branson continued to move forward and his group now holds more than 200 companies in more than 30 countries.

These are just some of many examples of people who have not let failure define them and that have actually used it as a motivator to become better and do more. Anyone can become successful at anything they choose no matter their age, life experience, circumstances, or past failures. With passion and hard work, anyone can be successful, so let’s make the rest of 2K17 count!


Raymondnative and former Manchester resident Brian Chicoine is co-founder of UrbanRebel 1636™, a Rhode Island-based art and design way of life start-up. A 1990 graduate of West High School, Brian attended college in the city before moving to Rhode Island to complete his undergraduate degree. Brian’s original plan was to “learn and leave” but fell in love with both his now wife, Jackie, and the state so decided to stay beyond graduation.

After they were married, Brian and Jackie lived in New Hampshire for about five and a half years, during which time their two boys were born. Brian and Jackie then returned to Rhode Island with their two boys and eventually started UrbanRebel 1636™. Brian and Jackie have recently realigned the company’s strategy and are developing an exciting new product line that will be introduced in time for the 2017 re-launch.

Brian has merged his passion for entrepreneurship and innovation with his love of new and bold ideas to bring the reader a fresh perspective on the people and products helping drive the economy. Brian and Jackie live in Providence with their two boys and their cat.

About this Author

brian-chicoine

Brian Chicoine

Brian Chicoine – a New Hampshire native – first moved to Manchester from Raymond in 1980. Brian lived in Rhode Island from 1997 to 2004 then again from 2009 to 2017, coming home to Manchester between the two stints. Brian returned home to the Queen City with his family from their most recent, (and last), Rhode Island adventure in mid-2017. Brian and his family are excited to be living in Manchester and are focused on contributing to their community. Brian merges his life experiences with his passions for community and innovation to develop his articles. Brian and his family live on the West Side.