The idea of “enough” is not a common notion in American culture. From an early age we are taught to strive for, accomplish, and acquire more. Endless comparisons to our neighbors are rampant, and we are always trying to “keep up with the Joneses.” Our successes are never enough—“I sold my company but only made $1 million from it—I’ve really got to go for it the next time.” Our cars are not fancy enough; our toys are not the newest, best ones; and our house can always use a bigger something.
The first entrepreneurial success is a defining moment for many entrepreneurs and their partners. While some entrepreneurs grew up with financial resources from their families, many didn’t. They start their first company with no money, sleep on a mattress, drive a car that barely works, and save every dime they can for when they might need it if things don’t go well. A first-time entrepreneur’s life is exciting and intense, but rarely extravagant.
While many entrepreneurs toil away for many years before having a financial success, when it happens, it often happens fast. One day you have no money in your bank account, have plenty of debt, and are often shuffling around small bits of money to make ends meet. Then your company is acquired, and overnight you have a bank account with seven, eight, or even nine figures in it.
It’s disorienting. Previously, you spent no time with money managers—even going to an ATM generated some anxiety that there wouldn’t be any money available, ...