Last Updated 04 Jul 2021

The Benefits of Repeat Entrepreneurship

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Imagine that you’re in your car, getting ready to drive to a place that you’ve never been before. Sure, you might have a map pulled up on your phone, but wouldn’t you feel a bit better if you’ve made that drive before?

The same principle applies to other types of ventures, including entrepreneurial ones.

Entrepreneurship doesn’t come with helpful signposts or a GPS. There are books that you can read and websites that can offer some great insights and tips, but it’s hard to beat the benefits of previous experience. Dennis Mortenson, founder and CEO of , a cutting-edge technology company that provides businesses and individuals with digital personal assistants that set up and schedule meetings, knows this well.

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Here are three ways repeat entrepreneurship can help you reach success.

1. Knowing the entire path is invaluable.

There is a beginning, middle, and end to every entrepreneurial venture, and your level of familiarity with each of these stages will likely determine your confidence in navigating your way through the journey. According to Dennis, if you haven’t seen the middle or the end of an entrepreneurial path before, it can be tough to know if you’re headed in the right direction or to feel comfortable taking certain steps. This sort of familiarity and comfort with multiple stages of the entrepreneurial path may be even more valuable than technical skills, he believes. “It’s certainly much easier to imagine the road ahead if you’ve seen the road before,” affirms Dennis, “I certainly feel quite comfortable about where we’re at today and where we’re headed.”

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2. Every “failure” can teach you something.

You don’t need to be an immediate success to be able to gain necessary experience and knowledge. Even a failed venture offers entrepreneurs wisdom on what to do differently in the future. “Of the four prior ventures we've done, we've been fortunate enough to have three good assets and one that didn't work out,” Dennis remembers. “That one that didn't work out was a little bit less data-centric and we actually didn't own the data.” That’s a mistake that he says that he will never make again.

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3. Entrepreneurship is a skill.

While many see entrepreneurship as a calling, Dennis believe that entrepreneurship itself is a skill that you can improve over time. “You can become a better entrepreneur over time,” he says. He should know -- a veteran of five different ventures over the past two decades, he’s honed his entrepreneurial talents and gained a lot of experience in running successful businesses. By traveling the path multiple times, he’s had the opportunity to battle-test his skills in a number of different situations, and learned what works and what doesn’t.  Anyone can become a better entrepreneur with enough effort and experience, he says.

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