What it feels like to be Rich

After losing over one million a week, cash, for the entire summer of 2000, I was forced to sell my apartment.

So one day in 2002, all the boxes were packed, the apartment was empty. We had two moving trucks waiting downstairs to move us an hour north of the city.

It was like an exile. My self-esteem was gone, my apartment was gone, I hadn’t slept a full night in almost three years, and other things I can’t even talk about.

My ex-wife, my two toddler girls, and Lynne, a close family friend who was helping us move, were taking one last look around. “Oh. My. God,” Lynne said. “This is really it.”

It’s been a decade and a lot has happened, good and bad (mostly good). Someone on quora yesterday asked the question, “what’s it feel like to be rich?” I figured I’d answer based on my pre-2000 experiences. I’ll save 2000-2010 for another time.

A lot of people started answering the quora question with “I was able to buy this, or that, or ‘this and that’. “ Money was never about that for me, then or now.

There’s never been anything I wanted to buy (other than the next ipad!) I have minimal material possessions.

If you know me you’d see I dress like crap and the edges of all of my pants are frayed. I don’t own a suit. I don’t have a drivers license so fancy cars are out.  I like comic books more than paintings. I don’t like to fly or sail. And I don’t drink wine or eat out a lot.

So what did it mean for me back then:


I finally felt good enough about myself to pass on my genes and have children.

I never wanted to have children before that. There’s apparently some evolutionary reason that we feel a strong urge to pass on our genes.

I had never felt that before but somehow having a significant amount of money gave me permission to want to have kids.


For the briefest of moments, I felt “safe” – like nothing could harm me and I could live forever.

In 1999 I visited the Chairman of a company I was a shareholder of. I was in LA and he picked me up at the hotel in his latest Porsche. We drove to his enormous house and he gave me a tour. When we sat down he told me, “I don’t even have to do this anymore. I have so much money now that nothing can touch me.”

I know it sounds unbelievable and a cliché but a year later he came down with cancer. After battling with cancer for years he was given worse and worse news about the outlook until eventually he shot himself and his kids found the body.

I heard about the news when his wife called everyone in his address book. This is not meant to be a lesson. Money has its benefits but immortality is not one of them. (Although, if you must –  How To Live Forever).

Another example. A friend of mine was running a prominent gaming site and wanted to maybe sell it or do something with (it was 1999, so why not?)

I introduced him to a successful guy I knew on Wall Street. I couldn’t even find the guy’s office. I had never been down as south as Wall Street.

My friend and I sat there while Shlomo (not his real name, but you get the drift) said, “look at me! Ten years ago I was a shlub. Now I have 100 million dollars. Only in America, right?”

About two years later Shlomo was in the center of a massive FBI sting involving a currency brokerage he had started that had been simply pocketing investors money since the 70s.

He went to jail. Even my orthodox friends turn away and refuse to talk about him whenever I ask if they knew him.


My feelings of safety and immortality quickly gave way to scarcity.

After all, I thought, if I could make 10 million dollars  then it must be too easy.

In fact, I honestly thought, everyone else had probably already made 11 million dollars. So then I felt poor again. I now needed 100 million dollars to be happy. I drove in a car with a friend of mine and his wife. I said, “everyone has 10 million dollars now.” She quickly said, “not everyone.”


I lost some friends. Then I made some new friends.

By the time I was going down in the elevator from my apartment that one last time, 100% of those new friends were destined to never speak to me again (at least through January 12, 2011).

My new friends said things like, “Mark Cuban is a stud” or “Fuck him. Take away all his shares” or “Good luck. Have a nice life” or “of course its legal!”

(one of many paintings I bought)

The value of money

I realized (too late then, but I learned) that I never knew the value of money. I had never even been aware of money before. My prior goals had been playing games, making fun websites, or writing novels.

Now my only goal was money, money, money, and more money. I told my therapist at the time, in 2001, “its like losing a loved one” and she said, “sweetie, sounds like you’ve never really lost a loved one before.”

Money is a great thing. It’s the payoff on hard work, great luck (which is often earned luck) and you can do amazing things with it. Build new businesses, create  jobs, buy your independence and freedom from corporate America. But first you have to climb many hurdles, of which earning the money is only the first.  Very few things are better than earning a lot of money.

But money finds a home only in places where it’s appreciated. I didn’t appreciate the money. So it left me.

When we were in the car, driving to our new home back in 2002 it was in the middle of a snowstorm. I wanted to cry I felt so bad about what was happening. But it was too much to think about. So for a brief moment I watched the snow and remembered what it was like to be a kid. Tasting the first snow of the year on the tip of my tongue.

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