Answer by David S. Rose:
Being a millionaire ain't what it used to be :-). In thinking about net worth, it's helpful to consider everything using a common denominator, such as your potential annual income based on the return that the wealth could theoretically generate. (Because otherwise, if you start spending your principal, you won't be a millionaire very long.)
So, for example, a million dollars put into the safest CD you could find, might, if you were lucky, generate 1% interest each year… which is $10,000!
Even if you had, say, $5 million, and were willing to take a fair bit of risk and put it all in the stock market where it might (with real luck) generate 5% as a sustainable annual withdrawal, you'd still be making "only" $250,000 a year. Take out taxes (being very generous, let's use a 20% rate) and you're at $200k.
That's enough to rent a nice apartment (or pay the mortgage on, say, a +/-$1m house), take a nice vacation each year, and probably pay private school tuition for one or two kids… but you're certainly not going to be flying your own Gulfstream with only $5 million.
Next, if we skip over the run-of-the-mill deca-millionaires and jump to someone with $100 million in assets, NOW for the first time are we just getting to the point where you have a good bit of flexibility.
Assume that with this kind of cash you begin to have access to some good hedge and venture funds, so maybe you'll be able to consistently get 8% on your money. And now that you're in the privileged class, we'll figure you can find some good tax shelters and squeeze things down to a 13% tax rate. This means you'll net out to about $7 million disposable income annually.
At this level you can do pretty much anything you'd reasonably want. Pay the mortgage on a $10m mansion as well as a $5m summer place in the Hamptons, put four kids through Ivy League colleges, fly first class anywhere you'd like, make half a dozen angel investments at $250K each, eat out every night at three star restaurants, vacation on the Riviera, and have a full-time cook, butler, nanny and chauffeur. I expect you'd even tithe $1m annually to good causes, which probably gets you named Man of the Year for a big local charity.
All in all, not a bad place to be! But still no Gulfstream, no $35 million penthouse in midtown Manhattan, no building named after you at your alma mater, no mega-yacht docked outside your Riviera estate, no getting Justin Bieber for your daughter's quinceanera, no 24/7 security detail like the President, no executive-producer credit on Avengers 3, no invitation to the Allen & Co retreat, no mega-trophy-spouse.
All that needs to wait until you get your first billion and put it to work.
Here we'll assume that with enough portfolio diversification you'll finally hit a Google or LinkedIn, and be able to comfortably plan on >10% annual returns from your professionally-managed holdings. And since you're now an oligarch, let's say that your hardworking gnomes will figure out how you can limit your net taxes to <10% (very tough on a big portfolio, but we'll assume your gnomes are really creative.)
This means you'll now have close to $100 million a year after taxes, and FINALLY you can afford all those things you've always dreamed of! While you might not be able to pull off in the same year paying cash for BOTH the $85 million pièd a terre in Manhattan that Russian guy bought for his daughter, AND the $150 million megayacht of the Sultan of Dubai, you'll be in pretty good shape.
However, those constraints DO make a difference when you're playing in the big leagues, so figure that you'll have to step up to the next category, before there really are NO practical limits to what you can do and how you can live.
Once you get above the $10 billion level, all is good, and you can both help change the world (viz. Bill Gates) AND indulge yourself in any way you desire (viz. Larry Ellison and various sultans). From this point on, it's simply a matter of score-keeping in the great Monopoly Game of Life. You'll need to decide for yourself how important your place on the Forbes list is, and whether you care about your standing relative to Mark Zuckerberg ($10 billion), Michael Bloomberg ($22 billion), David Koch ($25 billion) or Warren Buffett ($44 billion).