Most of the successful entrepreneurs I have known—including the guy I look at in the mirror—have a tendency to overrate their personal skills and wisdom. One of the great benefits of meeting confidentially with a group of peers is learning how much you don’t know—month after month, year after year.
All too often, entrepreneurs are experts at one or two things, but they don’t have a clue about the rest. Creating and growing a business requires a broad set of talents and skills. Those who dare to do it without plugging the holes in their skill sets are only increasing their already high odds of failure. Some of us learned this lesson the hard way, while others were lucky enough to make good hiring choices along the way. The smartest among us acknowledged our weaknesses at the outset and made sure we had a team in place whose talents made up for them, even before we launched our companies.
Over the course of Pete Settle’s career, he came to recognize that he was not a happy administrator. “Everybody is defective in some way,” he notes. “The best thing I did as a leader was finding people who could complement my weaknesses, which are many.”1 Pete managed his family’s school bus company and then worked as a top executive for the large public company they sold it to. When he started his own company, the first thing he did was hire his older brother Mike as his chief operating officer.
“We have very complementary skill ...