First off, I wouldn't mind being a world-famous billionaire. I know a couple of world-famous billionaires, and their lives are pretty darn cool. But such a goal is easier set than achieved.
Until that time, my happy and optimistic brain has tackled the easier task of finding the good side of not being a billionaire. The funny thing is, there actually are some major advantages!
1) You get to choose when to attract attention.
It may sound like fun to be at the center of every party, or to be approached by worshipful fans wherever you go, but judging from the reactions of many celebrities, it's not.
It's fun when you're in the mood to be "on," but not so fun when your kid work you up in the middle of the night, you didn't get enough sleep, you have a cold, and you really don't feel like spending an hour chatting with fans, all of whom have Twitter accounts and camera phones.
A life of quiet desperation isn't a good thing, but a life of quiet is.
2) You don't have to say no all the time.
For a people-pleaser like me, this is a heck of a benefit. I hate to say no or disappoint people (which is why it's ironic that I'm an angel investor--I have to reject 99% of the entrepreneurs I meet).
People instinctively rein in their requests when talking with a normal person, but these restraints go to the wind when you're a billionaire.
Your friends would probably borrow a buck to buy a McDouble off the $1 value meal, but they'd never ask you for a $100,000 investment.
Yet this is exactly what happens to billionaires. Even I, the poorest angel investor I know, am inundated with requests.
If you have $10,000 in the bank, you probably don't hesitate to lend a friend a buck. That's just 0.01% of your net worth. The equivalent percentage for someone with a $1 billion net worth is $100,000.
In other words, a billionaire looks at BMW prices like you look at the Taco Bell $0.59/$0.79/$0.99 value menu.
That probably sounds like fun. But it's less fun when all your friends and relatives come to you for money.
3) You know your relationships are real.
I've saved the worst for last. Entrepreneurs sometimes ask my why VCs are so arrogant. I tell them it's a matter of circumstance, not personality flaws. "Imagine that every day, 10 strangers came to you and told you how brilliant you were. Pretty soon, you'd believe them."
Sounds fun, right? And the effect is even stronger when you're a world-famous billionaire. Who's going to say no to you?
That's the problem. Positive Psychology's founder Martin Seligman tells us that caring relationships are one of the five critical factors to our happiness. But massive wealth and fame make it much harder to find these authentic relationships.
We often make fun of famous athletes like LeBron James who maintain an entourage of old high-school buddies. But in his case, it's a rational move. He was on the cover of Sports Illustrated as an 18-year-old. His nickname was "The Chosen One." His family and old teammates may be the last people in the world whom he can be sure developed a relationship with him for him, and not for his wealth and fame.
People act differently around the rich and powerful, even me. Since I've had the privilege of spending time with a lot of rich, famous, and or powerful people (sheer accident, in most cases), I've seen how people act around them, and how even my behavior can change, despite my self-awareness. And that's even true of folks I knew before they were famous.
Hollywood's child stars are notorious for self-destructing. It's not that they were bad kids; rather, they were forced into dealing with the challenges of wealth and fame before they had the wisdom to handle the attention, deal with favor-seeking from friends and family, and worst of all, before they had a chance to develop a decent number of strong and mutually caring relationships.
So while you may lament your life as an obscure thousandaire, look on the bright side. You're building up the skills that will serve you well when the spotlight comes calling.