The Main Street Entrepreneur

By Spicer Matthews

The word entrepreneur has been bothering me lately (yes, I know, #firstworldproblems). I have spent almost half of my working life in the tech startup world and the other half in the main street small business world. The tech startup world defines entrepreneurs as individuals with a bright idea who raise money from investors and try to make it big. This type of entrepreneur typically gives up a job at a company like Google to run their own show. But are they really running their own show? I say they are merely trading their managers at Google for managers in the guise of investors and board members. The truth is, a tech startup entrepreneur is not his (or her) own boss. Though the potential payoff for succeeding is enormous, the risks are also great and the tech startup entrepreneur gives up many of the freedoms a main street small business entrepreneur enjoys.

When I was growing up my dad was a main street entrepreneur. He ran his own insurance company in addition to some side businesses. He was his own boss. He attended every one of my soccer games, never missed a parent-teacher conference, and was always there to say goodbye to me as I trucked off to school. And he took our family on several weeks’ worth of vacations every year. He was present, happy, and in control of his own life.

I am not at all suggesting that a main street entrepreneur does not work hard. My dad sure did—but he was in charge of when, how, and what he worked on. It’s not news that we all have days when we do not want to be at work. You might be tired from the night before or distracted by something else, but if you are not your own boss you probably have to just sit there and chug through the day. The main street entrepreneur does not. He can focus on that something else and take care of work when the time is right. He is not lazy—he simply has more options.

Which is to say that all entrepreneurs are not created equal. I have come to realize that the kind of entrepreneur I aspire to be is a main street entrepreneur. Life is short. Spending half of my waking hours (or more) being managed by a boss or toiling for investors does not sound like fun to me. Which epitaph would you want on your tombstone: “He Made His Bosses Rich” or "He Did What He Wanted When He Wanted"?