I pitched my company to an investor and he wants to date me. What should I do?

I can’t stop thinking about a potential investor who is trying to get me to sleep with him. I live in Silicon Valley and he’s an active angel investor with a great reputation. So, to say I was excited when I got my first meeting with him would be an understatement. He’s personable and immediately seemed interested in my company’s vision.

Our first couple of meetings were all business. Then he started sending me flirty texts. Then he tried to kiss me.

The truth is I want to work with him but I have no interest in sleeping with him. I’m now worried that we’ll never be able to have an exclusively platonic business arrangement because he’s crossed the line with me. I’m also worried that he’ll back out of funding my company or worse yet, potentially poison the well with other investors by saying negative things about me if I don’t go along with it. People around here are so fickle that all it takes is for one “popular” investor to say an entrepreneur is incompetent for that to become accepted in the echo chamber.

So, I feel torn. I either shut him down completely and risk his wrath, or literally “take one for the team” and start sleeping with him in order to get continued access to his contacts and money.

3 replies
  1. Penelope Trunk
    Penelope Trunk says:

    This is unconventional advice, but…

    This is what I would do. Tell him you don’t think you’ll ever get funding from him if you kiss him. He’ll say, that’s not true. Say, okay, wire money to my company’s bank account and then we can talk.

    It is almost prostitution but it’s not. And it’s fine. You can kiss him and do nothing else. You can kiss him and tell him you met another guy you want to date exclusively. Whatever. The whole situation is stupid on his part. So it’s hard for you to make a mistake bigger than his.

    You’ll only have a little time in your life to do this. Most women who had the chance to take advantage of situations like this and didn’t regret it later. Because the situations dry up fast.


  2. Deborah
    Deborah says:

    I’m not the person who asked this question, but I’m raising my hand to say that I love this advice.

    I love that it places the responsibility for creating the situation squarely on the person who actually created it.

    I love its sharp observation that “it’s hard for you to make a mistake bigger than his.”

    And most of all, I love its judo-esque practicality — it uses the attacker’s weight against him to flip the situation to your advantage.

    Love. This. Advice.

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