The parsimoniousness of even incredibly successful wealth creators used to leave me a bit dumbfounded until I realized how central the trait of frugality is to the psychology of the entrepreneur, rooted in their capacity for self-discipline. (You see this much less with second- and third-generation inheritors of wealth.)
A few years ago, I flew to Washington, DC, to check in with Tiger 21 chair Cal Simmons (Lesson 22). Cal was late. “Sorry,” he said, as he hustled into the room. “I just can’t stomach the $20 valet parking fee. I was driving around looking for an empty meter.”
“Why?” I asked, wondering to myself whether he had any idea how valuable each of our time was.
“I grew up in a household where pennies were kept in a jar,” he explained. “I’m not alone in the group in being this way. So many of us have worked so hard to make our money that we really don’t like to spend it.”1
Cal had reminded me of something that is easy to forget about Tiger 21 members. If you put forth the question, “Who in this room is middle class?” the majority of members would raise their hand. No one is looking for sympathy, but most our members are self-made men and women who, psychologically, remain rooted in poor, working-class, and middle-class backgrounds.
George Heisel (Lessons 2 and 5) comes by his frugality naturally. His father ran a family business and remained frugal to the day he sold it. George got nothing from the windfall, but he was hardly surprised. ...