> people evaluate their actual value and see that it probably is not enough to make it worth their while approaching this person.
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.
A related point: if you know someone big/important is going to be at the event you're attending and you want to meet this person for whatever reason, it's well worth researching him/her beforehand so you can ask an intelligent question that shows you've done some homework and are not just out for yourself.
Be interesting, be memorable, do not be desperate (never attractive). And don't wear out your welcome, especially if you know other people are hovering (so they can make their own move on cool person) or if cool person clearly wants to duck out/away.
This chance to prepare, btw, is a key difference between meeting a big shot and hitting on a hot woman you happen to see at a bar.
There is also cost of your time for the coffee and whatever may follow, as well as material costs (potentially high when dealing with upper-echelon), so it is not an outright win situation.
Only the ones that are willing to fail repeatedly are the ones who deserve to win. What I'm trying to imply here that taking risks while maximizing your odds is also a skill.
A super hot woman (or GS executive) both appreciate confidence and candor. They don't want to be treated as "different" - to return to that hot woman - she doesn't want to be treated as special. Looking into mirror is enough to get her depressed. She wants to feel ordinary, to be appreciated for being a woman or at least not a freak.
I know a founder of one of the top silicone valley start-ups.
He's a great guy and when I happen to see him it's fine to chat. He's very busy so I don't see him very often.
This relationship gets me zero, zilch, practical benefits.
It's fluke that I know him. Would I expend a lot of effort to get ten relationships with similarly well-connected people? No, because it would rather insincere and would get me ten times as much practical benefits (ten time zeros). The people who I happen to meet and are cool people, I'll be friends with. The stunningly beautiful ballerinas I've chatted with are nice also but not the best material for personal relationships...
In other words, the glory of knowing COOs and dating models also over-rated. And if the models are feeling truly neglected, I'm sure they won't have a problem introducing themselves to cute guys at bars if they want "glory".
Silicone valley? Is that where all the hot models hang out?
More seriously, you might not have realized any huge benefits from this relationship with your founder friend, but that doesn't mean there aren't some significant potential benefits to your relationship.
Say you just happened to have a wonderful new product that your friend's company could use. A short chat with your founder friend about this product could be worth quite a lot.
Likewise, if you needed or wanted some advice from him, the advice of a founder could be worth a lot, as could any introductions to his peers that he might be willing to make.
Just think about it a bit, and I'm sure you could come up with dozens of other potential benefits.
Of course, such a relationship shouldn't be one-sided. There's a great book called "One Phone Call Away" by Jeffrey Meshel, who's main point is that the best way to network is to help people without expecting anything in return. Highly recommended.
Are you of any benefit to your founder friend? My personal strategy is that I constantly work on maximizing myself as benefit to others. This gives me an edge - where I can actually pick such partners that return appropriate value. Increasing demand is actually really simple - just offer better (sought after) goods.
As far as the poor pretty girl that needs to hit on guys. Unfortunately it doesn't work this way. Its got a lot to do with guy's and girl's insecurities.
1. Hot woman hitting on a guy - The natural reaction of the said guy is "It's a trap!".
2. Having to hit on guys is awful for this woman - since less pretty girls don't need to do it. Which starts spinning up in a persons mind that you must be some sort of freak since a) mend don't hit on you and b) when you try to hit on men they run away ("It's a trap!").
Oh and the glory thing is just a parable for success.
We all make choices - maybe I wouldn't want to invest much of my precious time in having Coffee with the CEO of Goldman Sachs. Let's say I don't work in finance and have no interest in it.
As for hot women, it depends on what you want. For a real life example, let's say I am married and have no intentions of cheating on my wife. So I will certainly chat with a hot woman, maybe even flirt with her, but I'll certainly not put a lot of effort into pursuing her as I have no interest in sexual relations with her.
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.