Ah...but I wonder if there is a different lesson here when the whole story is put in perspective.

First, some context from Robert Cringley:

"These roles changed over time, of course, and what clearly precipitated the change was Paul Allen’s health. He contracted Hodgkins Disease, a form of cancer, in 1982 when Allen was in charge of the development of MS-DOS 2.0 ...

During one of those last long nights working to deliver DOS 2.0, I am told that Paul Allen heard Gates and Ballmer discussing his health and talking about how to get his Microsoft shares back if Allen were to die ....

Paul Allen, who never returned to Microsoft, and over the next eight years, made huge efforts to secure his wealth from the fate of Microsoft. He sold large blocks of shares on a regular basis no matter whether the price was high or low."

For me, there are two conclusions about the Paul Allen story:

1. The old joke, "How do you make a small fortune on Wall Street? Start with a big one," is funny, but for most folks, true.

2. I think this is the myopic type of article only a New York financial paper would write. So Paul lost a ton of money. He still has $15B, more money than can be spent in many lifetimes.

But more importantly, as a cancer survivor, he gets to live his one life any way he choses. He has true economic freedom.

And most importantly, he has been able to separate himself from the type of people who would ever have such a conversation.

And I am sure, that is all Paul Allen cares about. These theoretical financial losses are meaningless in the context of what is truly important, and makes the Bloomberg article kinda silly. (And I say this even as a greedy entrepreneur myself...)

1) In all fairness to Allen, if anyone held $30 billion in stock in any single company, you would have to diversify -- just so you could sleep at night. Its one thing for a few $100,000 or even a few million to move up and down; What if every tick cost you a few million dollars? Who the hell needs THAT?

2)Once you acquire your first billion dollars, there's really nothing on the planet not available to you. Every billion over that is merely scorekeeping;

3) What could be more fun then blowing billions on (and I quote) fast cars, planes and women?

Hey Barry -- I don't totally disagree, but, put differently, Allen would have done better in almost any diversified investment than the one he chose. You name it, it would have beaten him.

Wrt profligate consumption of fast cars, planes, and women, I'm hard-pressed to imagine how you blow more than a half-billion, but maybe I lack imagination :-)

Actually, according to Bloomberg markets, Paul Allen's net worth is more like $8 billion. $12 billion or so in assets and $4 billion liabilities. Mr. Allen might possibly have lost more money than anyone else in history, outside of losses in founder's stock. Larry Ellison has lost of a lot of money from Oracle's peak, too.

Allen should possibly consider not managing the money by himself. The article itself was curiously congratulatory to his new investment managers. They are "classically-trained investment managers," according to the Vanessa Bailey, a headhunter who works for Vulcan, Allen's investment organization. So when did mid-level investment bankers with no operating experience constitute a good group of people to trust your money to for the long-term?

What's very sad is that Allen's money is welcome at of the top investment management shops of the word. Nothing is closed to him. Had he put his money with a KKR, ESL, etc... he would have been much better off than with his own in-house investment team.

As much as that article lauds the team, all I see is a group of mid-level finance jockeys with no track record. The author of the Bloomberg article appears to be biased.