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The theory above is short term (get a date), when there is also the long term consideration (marry her, have kids). If you are an average joe, the chances of you having kids with a hot top model are, very frankly, very low. And we guys know that. In the same way, the chance of us having a nice chat with the CEO of Goldman is fair, but the chance of him maintaining contact with us and being a friend or mentor is pretty low. You don't have the money to hang with him, you don't have the opportunities to share with him and so on. So you can get a date with the top model if you're brave. You can get a coffee with the CEO if you're brave. But I doubt that anything long term will develop, unless you have true value to offer. And people evaluate their actual value and see that it probably is not enough to make it worth their while approaching this person. An example that I'm sure many here can identify with: How many of you have emailed Paul Graham asking him for feedback on your app or whatever? Some brave ones likely have, but how many realistically expect a relationship to develop out of that? |
Cost: Awkwardness, potential for embarrassing rejection.
Benefit: Possible relationship, either short-term or long-term, with the subject of your admiration.
So in my mind, if you can get over the fear of rejection, there's no reason not to at least try. Coffee with a CEO is better than nothing, and may potentially be useful down the road. (Can I have a job? Remember when we had coffee that one time?) Likewise, a date with a beautiful model, even one, is better than eating ramen alone. Well, usually. :)
Also, while I agree with what you said about having "true value to offer", there are many types of value. When developing a relationship with someone like a CEO, you may not be able to offer them direct monetary value, but you might be able to give technical insight, an outsider's point of view or a perspective from a different industry, or even just a like-minded person to talk about basketball with.
My advice is to look hard for the value you can offer. Knowledge that you may take for granted is often quite valuable to others, or at least interesting enough for them to keep you around and ask your opinion.