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> 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.

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.

No risk no glory!

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.

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.

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.

Hmm,

Would you like to have coffee some time next week?

I'm in the SF Bay area and my email is on my profile (for now).

Would Tuesday or Friday work best for you?

Great point about value.

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.

   > 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

I've had something very similar go well. Putting yourself into surroundings where you have positive interaction with successful people is a good strategy.

    > You don't have the money to hang with him, you don't
    > have the opportunities to share with him and so on.

Interests might crossover. Re my story - I worked for a small vendor that nobody cared about, but was drinking seriously with a customer. We were talking about exercise. I was a not-very-serious middle-distance runner. After a bottle and a half of red each he convinces me to promise to one day do an ironman triathlon with him. I couldn't swim at the time.

Six months later, I'm into training, and interviewing at another firm. The place I'm interviewing at has several people who are nuts about triathlon.

The job's great, but that aside, so is the new interest. I did Olympic distance this year, signed up for half ironman in 2011. I still swap emails with the guy.

Some people with lots of money don't care about it. If they do, they'll filter you and save you the hassle. People who are capable of helping you are the most likely to be interested in helping you. You're their canvas.

It can work. But there is a cost - you may annoy the guy. See, if you fail, then the guy will remember you negatively. If you succeed, but cannot offer value, you lose also. I believe that's what people try to avoid.

Thanks. OK - yeah you did say "unless you have true value to offer".

Still, you might be psyching yourself out. In your original post you wrote 'hot top model' whereas the original article wrote 'hot girl'. Not the same thing.

I've never asked someone out on a date expecting to get married. Things go where they go. Having it all planned out before you even talk to her seems, well... silly.

Enjoy the moment. Talk to the hot girl or boy; introduce yourself to the celebrity or CEO, or VC or whatever floats your boat. But don't talk yourself out of it because of what you imagine could happen.

Nothing ventured, nothing gained.

I think game theory applies here, similar to the situation played in Beautiful Mind http://www.youtube.com/watch?v=v5jrNoNNtrE and conciously or not, many choose not to get involved, fearing too much competition and bigger chances of loss/rejection.

Same as in business - the bigger the jackpot, less chance of hitting it. Picking up hot girls and doing risky business need a lot of self-esteem. Difference is, in business you often have a lot to lose, while being rejected by a girl doesn't really hurt much.

Generally speaking, though, people are /horrible/ at evaluating their own value. Aside from extremes of ego (in either direction) which by itself could account for massive error bars, you have many other problems. Especially in the dating arena, and to a lesser extent in the professional context, even if you do know your attributes, it's often difficult to know what the other party values.

The long-term vs short-term argument makes sense, I agree on that. If you have nothing to offer in the long-term, then it's probably not going to last. If you just want to ask the hot girl out of your league on a date to say that you did, then yeah, it's probably not going to go very far.

I think the people who actually succeed in going out of their league, or the ones who do have that long term relationship with the CEO, are the ones who have the confidence that they do have some value to offer. And by definition, these people are more likely to take the risk - because there's something legitimate backing it up. Not saying that every confident person who approaches the GS CFO will develop a long term relationship. But the ones who actually attempt are probably going to be the same people who have the confidence in themselves to build a long term relationship - and believe they can offer some real value.

Excellent advice, keep doubting yourself so that people like myself with confidence have an easier time succeeding because people like yourself don't even try, let alone fail, let alone succeed.

I'd take a date with a model or a coffee with a CEO any day of the week. I don't care if the long term outlook is zero, it's worth it just for the experience.

If the article is true, the people like you are upping the chances of people who heed its advice. So, thanks?

I can see your point but I like to think that "even" CFOs of Goldman Sachs are just people - behind every oh so successful CxO is just a human being with often a horrible, horrible personal life due to all the work and responsibilities and politics and bullshit and all the ass-kissing people they have to face each and every day...

So I think if you honestly approach someone as a human being, who knows where it could lead.

If you approach them playing "just a human being" when actually you want to talk business and money, then you better be prepared for the other person to switch to "business mode" as well and yes, then they WILL evaluate you. Because after all then it was just all about business to begin with, wasnt it?

It really shouldn't matter to you what long term value you have to offer her. Being able to take a picture with her and put it on your Facebook albums is worth quite a bit imo.

There's no legitimate excuse not to try to associate with higher value people, you can only go up.