What Big Venture Capitalists Talk About

venture capitalists

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.

  • Steven L Goff

    You know what sexual position the “rusty trombone” is dont ya?… It’s related to salad tossing….lol…Google it!   here let me >

    Rusty trombone is a euphemism for a sexual act in which a man stands with his knees and back slightly bent, with feet at least shoulder width apart in order to expose the anus.Tate, Jordan. (January 9, 2007) The Contemporary Dictionary of Sexual Euphemisms.

    The Dutch rudder and the Double Ducth Rudder is also comical!

    • Fortunately I left my Dutch dictionary at home.

      • Steven L Goff

        get a girl to do the rusty trombone…..that how ya know she loves ya!…..LMAO

    • Steven L Goff

      a man on all fours with a girl behind him lickin’ his butthole while she is also jerking ya off at same time….hence rusty trombone!

  • Steven L Goff

    What Is The Dutch Rudder?



  • Title bothers me, it doesn’t apply to post – sample size of two.  I have a few VCs as close personal friends, none are like those two.  They treat people and friends very well.  How’s this title for the post: “Conversations with douchebags,” which I find rather humorous and more interesting.  Judging, I know.  But that was my response on those two after reading the post.  At no time did I think that was a reflection of VCs, though.  

    • Yeah, i guess i was making a play on the fact that they were “big” and at that time i was feeling so uncomfortable in my own skin, my own company, etc. Different world for me now.

    • It pretty difficult not to judge something, or someone, that literally goes against every hope you have for humanity. 

  • Matt

    So basically they’re just like me and you except really rich

  • James-

    It’s actually not form Oz.  It’s from a special HBO did about Riker’s Island.  If you ever have the chance to watch it, it will give you enough ideas to never have to talk about chess, yoga or the stock market again!


  • Nikita Tovstoles


  • Perhaps you’ve never witnessed the resulting orgasm? 

    That said, the idea itself holds no appeal to me. Had I not been surprised by it one evening I would never in a million years have had a desire to try it. And I’ve never asked for it because I haven’t reconciled myself to the notion of reciprocation. 

    • Seanasheppard

      ok..that’s funny

  • It would seem they talk about the same shit everyone else talks about. Men anyway. 

    Women have their own version of this. And it does involve penis size. (Sorry guys.) 

    • Ha.

    • willywonka

      You must be a nasty whore Brooke, because all men do not talk like this.  Birds of a feather flock together.

  • Jake

    It’s a shame….sad really. This kind of conversation takes place everywhere at every level, from school cafeterias to the white house. What’s the point? “Fun” from de-humanizing of “others” I suppose. No wonder we’re so messed up.

  • Anonymous
  • They tell me I am not qualified to be a VC.  6’5″-check.  Hooper-check, Can talk about women in demeaning terms-check(I was a pit trader for cripes sakes)  Must be because I haven’t tossed salad.  Thought they only did that in prison.

  • Jim

    I am a fan of your blog, but this post is pretty terrible. Not terrible in that it’s offensive, but terrible because it’s terribly boring… Wow, some venture capitalists talk like many other men? You don’t say. 

    Why would you feel the need to repeat specifics, anyway? I feel this post has only served to remind those around you to keep things quiet lest it end up on a blog

    • Maybe you’re right, Jim. I guess it just reminded me of a time when I was feeling pretty inferior and this scene sort of did it for me. But perhaps you’re right. I don’t know.

  • Anonymous

    I can’t tell you how sorry I am that I read this post.   Beyond reguritation!   Salad will never be the same, my diet is destroyed.