Entrepreneurs: Are You a Pretender or Contender?


The data: About half of small businesses fail within the first five years, and two-thirds close their doors within 10 years. Despite those high failure rates and the harsh effects of the coronavirus crisis on the U.S. economy, entrepreneurship boomed in 2020: business startups grew to 4.4 million – a 24% increase from 2019.

The question: Are you a pretender or a contender as an entrepreneur?

Expert’s take: James Webb grew up poor, overcame adversity in business, endured  personal heartbreak and cancer, and ended up as a highly-successful entrepreneur in the medical and fitness sectors. When he wrote a memoir, he gave it the subtitle: A Country Boy’s Journey To Prosperity. “Pretenders may make a lot of money but are one paycheck away from bankruptcy. They can be obnoxious and are not nice to people who aren’t on their income level.

“For contenders, money is no longer an issue. Humility, learning from mistakes, and resilience built from bouncing back all lead to success over the long haul. Contenders recognize where they come from and never forget. And as a result of those experiences, good and bad, they know where they’re going and have a better idea of how to get there.”

Turning point: Webb and his partners opened a string of private imaging centers in Texas, diversified the business’ offerings, invested in services and growth, and the company became well known in the industry. Sixteen years after Webb’s initial $25,000 investment, the company, Preferred Imaging, sold for $94 million.

Webb’s tips on becoming a contender as an entrepreneur:

  • Don’t avoid risk at all costs. “You either step to the plate or watch from the stands. There’s no such thing as a safe investment. Risk is a calculation, and if it comes with a big upside, you can’t be afraid to take a shot.”
  • Don’t misuse your boss role as a power play. “An entrepreneur’s job as boss is to provide their people with the best possible chance to succeed. This is done by ensuring they are in the right job, making the objectives crystal clear, supporting them and rewarding them.”
  • Trust what you know and keep moving. “Persistence is always the way.  Anyone who falls in love with the dream of entrepreneurialism and its upsides needs to also realize the nightmare of uncertainty and fear that go along with it. Don’t beat yourself up for mistakes, and don’t let your successes make you soft.”

James Webb is the author of Redneck Resilience: A Country Boy’s Journey To Prosperity. His career in radiology saw him rise from a technologist to becoming a leader in the industry as the entrepreneur of several companies. After over 40 years in the medical field, Webb focused on the fitness sector, owning and overseeing the management of 33 Orangetheory Fitness® franchises throughout North Texas.

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