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 prett…
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.