What Big Venture Capitalists Talk About

I was walking with Al and Skip and we passed a tall black girl that looked like a super model wearing a very tight-fitting white dress. Al whistled. “Thats a tall cool glass of water,” he said about the woman.

Al managed a venture capital fund that had about a hundred million in it. Now, ten years later, it has about a billion in it. All the money comes from unknown high net worths from the Middle East. Skip ran a family business that made $10 million a year. Both were 6’5” and played basketball in college.

We went for dinner.

Skip had a salad. He and Alex were talking about basketball. Then Skip turned to me, “You ever toss a salad?”

“What do you mean?”

“You know,” he said, “eat a girl’s ass?” **


He and Al started laughing.

Al had once arranged for me to get basketball lessons at Chelsea Piers. I was going to play in a charity event. Mark Cuban and Michael Jordan were going to play also. Everyone got to play one on one with Michael Jordan. I had never played basketball before. So I needed to learn. But then it turned out I was too young to play. You had to be at least 40. But I took some lessons anyway. I learned how to run without looking at the ball while dribbling and then jump and shoot. I wanted to be accepted by all the basketball players in my life.

Skip and Al started talking about Bill B, the famous basketball coach. I knew Bill B also. Between Skip, Al, BB, and Yasser Arafat they had about $8 million invested in my company at the time. 

Skip said, “every time Michael Jordan is in town, BB sets him up with hookers. All quiet. MJ’s wife has no idea.”

Al said, “she knows.”

Skip said, “She has no idea.”

Skip said, “whatever happened between BB and your friend Susie.”

I had a crush on Susie. I felt a little jealous.

Al said, “He fucked her that one time but it didn’t work out.”

Skip said, “How come?”

Al said, “BB said she had been with way too many men. He said she had the largest pussy he had ever seen. He said her pussy lips were hanging down like a cow’s.”

Skip and Al started laughing. I laughed also. I wanted to be friends with them. Ha ha.

Skip, Al, and I were walking down 15th street after dinner. “I’m in the penalty box with my girlfriend,” Skip said.

[I ran into Skip’s girlfriend a few years later at Sloane Kettering. She told me she was now married to Skip. She was volunteering to help with kids who had cancer. I was visiting a relative. I’d bring cards and poker chips and we’d play until late at night or until he was tired. Chemo ravages your ability to play poker.]

“How come?” Al said.

“She read some texts on my phone.”

“Shit,” Al said.

I wanted to contribute. I said, “Heck, I’m married and I even keep a password on my phone.”

Skip and Al looked at me. They both laughed. I got the sense it was at me and not with me.

They were both 6’5” and played basketball.

I was 5’8”. And I wasn’t a very good venture capitalist to begin with.

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** Apparently this is a reference to the TV show “Oz”. And although I did the website for several seasons of “Oz” I did not know the reference.

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