My Start-Up is Bigger Than Your Start-Up...Web 2.0 One-UpsMANship

I was so disappointed to discover that even if I succeed in business by making anything over seven figures, it will all be for naught. I'll only have clawed my way to a new level of insecurity, one where I'll start counting in the tens of millions, and where having a BMW would be slumming it.

Or is that just if I were a man?

Katie Hafner's story today in The New York Times gave us a fascinating glimpse of the lives of Silicon Valley's entrepreneurial multi-millionaires. Apparently they, too, count every dollar when it comes to others' ventures.

Almost anywhere else, Reid Hoffman would be considered a major success. As an early executive of PayPal, he was in the money when the company was sold to eBay in 2002 for $1.5 billion. These days, he runs a new start-up company of his own while investing in others.

But when greater fortunes are made -- as happened recently to three former PayPal colleagues when YouTube was sold to Google for $1.65 billion -- Mr. Hoffman said he could not avoid a twinge of envy.

... Mr. Hoffman, who made enough from PayPal to "retire to a comfortable upper-middle-class lifestyle," said he felt no spite toward peers who later hit bigger jackpots. Still, he said, "there's always components of, 'Wow, you happened to pick the right time,' and that will always lead to some kind of implicit envy."

No spite, of course, that wouldn't be kosher. Just implicit envy.

I understand the conundrum, because you know what they say you can tell about a man by the size of his valuation...

I wrote earlier about the phenomenon of men who slum it until they get their first round of funding. This dyanmic isn't all that different; it's just the next chapter in the Flipper's Guide to Company Building. A number of the featured men were serial entrepreneurs (no women were featured, interestingly; I wonder if it's because of the abysmal proportion of woman-owned businesses that get funding or because Hafner couldn't find any women who claim they compare bank accounts). The product or service in many of these businesses seemed like afterthoughts to the exit strategies.

When he was growing up in Winchester, Mass., Peter Pezaris told friends and family that he planned to become a millionaire by the age of 30 and a billionaire by 40. ... True to his word, in 1999, Peter Pezaris sold his two-year-old business, Commissioner.com, to CBS SportsLine for $46 million, three days after his 30th birthday...

Pezaris, 37, who is now based in Boca Raton, Fla., said he still believed that he had "plenty of time" to become a billionaire by age 40 with his new start-up, Multiply.com, a social networking site.

It hardly matters what the site does; let's keep our fingers crossed for Peter. If he doesn't make it to billionaire status he's a failure.

I don't mean to make fun, but I must confess that we might as well be talking about links and the Technorati 100 and other metrics that women don't care much about. When I'm asked about my goals I refer back to a tattered sheet of paper that I've kept and updated; my list of outcomes that I work my butt off for:

--House: somewhere green and lush. Must have space for gardening;
--Time to read every day;
--Enough $$$ to not have to do work I don't love
--Wine collection
--At least one trip to a new place every year
--At least two trips to see family every year

I know, I know. Where are the metrics? Someone do the math and tell me, because I don't know.

That said, I don't want to give the impression that I don't find money important. Great things can be done with great wealth. And wealth says a lot when women are concerned. I don't know which spot Oprah has on the Forbes list, but just the fact that she's on it says something about women's growing entrepreneurial power. In an earlier post I was clear that I believe women must get over their fear of not speaking up for their worth.

One of the men profiled in Hafner's artic, James Hong, co-founder of Hotornot.com (that site MADE MONEY?) considered himself a pauper millionaire, nowhere near as loaded as his best friend, PayPal co-founder Max Levchin. Realizing that he'd been undermining his sense of self-worth by buying into the ongoing treadmill of one-upsmanship, he succumbed to his own form of freedom--he traded in his Porshe Boxter for a hybrid car.

"I don't want to live the life of a Boxster, because when you get a Boxster you wish you had a 911," he said, referring to a much more expensive Porsche. "And you know what people who have 911s wish they had? They wish they had a Ferrari."

I admire his move to take himself out of the game by rejecting the pressure to constantly upgrade his wealth. It takes a Manly Man to settle for just a couple mil.

I don't condemn men for keeping score; to do so would be to denounce a biologically-linked need to compete with other men. But I would like to point out that, as we get past that first level of Maslow's Hierarchy of Needs--you know, the survival part--there's no imperative to have to keep climbing without looking around. There's something to be said for the view.

As for me, my Jetta will suffice.