From 100 mil to 4 mil - John McAfee is the center figure in NYTimes article:

[Peter Gibbons]

http://www.nytimes.com/2009/08/21/business/economy/21inequality.html?pagewanted=2&_r=2&partner=rss&emc=rss


The United States economy experienced two such bubbles in recent years - one in stocks, the other in real estate - and both helped the rich become richer. Mr. McAfee, whose tattoos and tinted hair suggest an independent streak, is an extreme but telling example. For two decades, at almost every step of his career, he figured out a way to make more money.


In the late 1980s, he founded McAfee Associates, the antivirus software company. It gave away its software, unlike its rivals, but charged fees to those who wanted any kind of technical support. That decision helped make it a huge success. The company went public in 1992, in the early years of one of biggest stock market booms in history.

But Mr. McAfee is, by his own description, an atypical businessman - easily bored and given to serial obsessions. As a young man, he traveled through Mexico, India and Nepal and, more recently, he wrote a book called, "Into the Heart of Truth: The Spirit of Relational Yoga." Two years after McAfee Associates went public, he was bored again.

So he sold his remaining stake, bringing his gains to about $100 million. In the coming years, he started new projects and made more investments. Almost inevitably, they paid off.

[JTGalt]

Seems to be a lot of  that going around.

But you have to be some kind of special idiot to go from $80 Million to $741.00

=====

THERE was a time in the late 1990s when Josh Harris was a king of sorts. A Silicon Alley pioneer, he was flush with millions of dollars made from his first Internet company, and he was spending it wildly on a series of legendary SoHo parties, businesses and social experiments.

He wired a loft with Webcams to broadcast everything he and a girlfriend did (including bathroom visits). He enticed 100 people to live in an underground "bunker," outfitted with a stylized altar, a see-through shower and a firing range. He created some of the first Webcasts through a company called Pseudo Programs.

And now it is all gone.

These days, Mr. Harris sleeps in a friend's pool house in Los Angeles and earns a meager living playing poker at a racetrack.

Last week, in his first extended visit to New York in eight years, he said the $741 in his pocket was all the money he had in the world.

Working for an early online research firm in the 1980s, Mr. Harris realized that computer networks were the next big thing. He founded Jupiter Communications in 1986, which measured online traffic. His stock was worth a reported $80 million at one point.
http://www.nytimes.com/20...shion/30harris.html?_r=2

[Dennis Nedry]

All you really need to do is buy bond ladders, tax free munis, etc.  Avoid corporate bonds, they can go to zero.  (McAfee had Lehman Bonds....doh)

If you have 80 million, and you can get a risk free rate of return of say 3.5%, that's 2.8 million per year, and you don't ever need to touch the principal.
Be happy with the 3.5% and stay away from other investment vehicles.   Buy a nice house or two, and get a hobby.

This is exactly what I'd advise whoever wins the current Lotto, which is like a 200 million payout right now.