The Eye, The Imagination, and Two Hundred Million bucks.

During the dot com boom, early on – like 1995, I met a gentleman who sold an online trading system to a large investment bank for $50M in stock. During the dot com boom, the stock ran up to about 200M before his non-compete contract finished, and he cashed out his 200M about a year before the bust. He created his own VC Fund and has been playing with it ever since. I think he was 32 at the time.

My interaction with this fellow was during a non-profit’s fund raising meeting. I was familiar enough with him to ask the following questions:

Me: Holy smokes, life is good.

He: It’s been quite a ride, actually.

Me: What have you learned?

He: What I’ve learned is that my assumptions from the start-up days are incorrect about how wealth would affect me.

Me: How so?

He: Well, when I was in a two-bedroom apartment and cramming out the code and getting everything built, I thought if I could just get 5 or 6 million in the bank, I could live off the interest at about 200,000 after taxes for the rest of my life. You know, set for life. Now that I have many multiples of that amount, I am seeing completely new vistas, new ways that money can be put to use. It turns out it’s not enough for the things I now want to do.

Me: So you could spend it all tomorrow?

He: No problem. Go get a copy of the Robb Report Magazine. These people market heavily to the super-affluent. Buy this island, buy this jet, buy this castle, etc. Their goal is to ignite your imagination.

Problem is, I know these people. They have the yachts, the jets, etc. One looks like a bumpkin to them. Even with 200 million. So I’m trying not to blow it all in one place.

Me: How do you spend your time.

He: I’m learning how to fly.

Me. A jet?

He: Eventually…

I left it there. In other words his point was that the eye is infinitely expandable to meet the income and spend it. Clearly he was not planning to live off the interest. He turned out, in the words of Nassim Nicholas Taleb to be an optimizer, not a satisfizer. Looking for the bigger, better deal. Not looking for ways to be satisfied with what he had. Taleb makes the case that optimizers are less happy with life. Satisfizers find equalibrium, care less about what others think, and use the cards dealt within an economy that does not over extend their resources. He also makes the case that they are better friends (satisfizers) because they are present and available to be friends without being distracted by optimizing their time with you so they can be off doing the empire tweaking.

I think I have no idea which I am. I’m satisfied with so much in life, yet I want to expand my influence.

Hmmm