LESSON 22Think Bigger

When you ask the entrepreneurs in Tiger 21 how they became so successful, typically they shrug and say, “I got lucky.”1 I got lucky too, but if you create great companies, you’ve got something more than just luck going for you. Getting a better answer for what separates great entrepreneurs from the rest of us is one of the reasons I wrote this book.

“They always want to do one more deal, open one more branch—to go one step higher,” says Cal Simmons of Washington, DC. “Most people are content to be successful with just one step.”

I often seek out Cal for advice because, as an entrepreneur who created two companies and sold them while simultaneously branching out as an investor, he has a unique perspective on wealth creation. In many ways, he’s a classic entrepreneur, a self-made man from a middle-class background who had a paper route as a kid and was a good-enough tennis player to make spending money giving lessons. In college, he started a publishing company. The day he graduated, he started Washington Tennis Services, which took a management fee for scheduling lessons with tennis pros at indoor tennis centers. Three years later, with a stable of teaching pros working in 30 states, Cal sold the company. He was 25.

“Business was easy for me,” he explains. After dabbling in real estate and publishing for a year, Cal figured that he could combine his urge to travel with his love of business by opening a travel agency. He rented space in a busy neighborhood. ...

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