Most folks are as happy as they make up their minds to be.
Absent a clear understanding of what specific financial goals one is trying to achieve, one can just continue to chase more and more money, never knowing what the finish line should be. Many founders have made their dreams come true—at least those they might have articulated years ago. Not following the advice they give their clients, many don't periodically reevaluate how their desires and their wherewithal actually stack-up. They've started and grown successful firms, they've given careers to many people, and now they sit with an opportunity to monetize the value that has been created, through an internal equity succession or an external transaction. That opportunity for “enough” is easy to miss. Failing to genuinely assess what is, in fact, enough can lead to always wanting more. Randy Webb, CEO of Signature, uses a great analogy: “Everything has a goal or a limit. Businesses and financial wealth are like trees. They can grow, but they eventually have some limit. Trees can't grow into space.”
Consider the extraordinary wealth of Warren Buffett. In 2014, according to Forbes's list of the world's richest people, he was worth $73 billion, but he was not the richest person in the world. There can be only one person with the most money: his friend and sometimes bridge partner, Bill Gates. So Warren is either already satisfied with his capability to do ...