About a year ago, a colleague invited me to meet one of his mentors, an executive at an Asset Management firm. When I met the mentor, he was with 3 of his friends, also in fairly senior positions at various firms. We hit it off immediately, but after 2 drinks, my colleague said we had to go meet the rest of our team at another bar, and invited the MDs to continue at the new location. About half an hour later, I saw the MDs make their way through the crowd at the new bar and initially mostly ignore my colleague and me. Then, after another drink or two, and very suddenly, the mentor turned and walked towards us with a big, malicious, grin. He stopped right in our faces and said "I'm gonna get you guys laid." And so, our night escalated very quickly.

We followed this man from one attractive woman to another as he opened up conversations with different groups, then followed up with the most attractive ones and introduced me to them. I took down the numbers of the women I liked the most, and after he went through the whole bar rather thoroughly, he insisted on a change of venue. As we followed him through 5 more bars that night, he basically repeated what happened at the first bar. His friends got involved whenever they felt interested, but mostly stayed on the sidelines and pointed out their keen interpretations of the various social situations we encountered. Finally, the older guys started leaving, until the last of the MDs turned to us and said to make sure that our leader was in a cab and on the way home to his wife by 2am.

Around 1:00am, a woman stood beside our mentor and introduced herself. He acknowledged her, and before she had a chance to do or say anything else he said, "Look, all I really care to know is whether my friend over here can fuck you tonight." She giggled and said that she's married. To which he replied, "Then what the fuck are you doing talking to us?" He repeated his directness a few times, but never got a slap, only a polite "I don't know your friend" or "Maybe some day," but never a direct rejection. At that point I had my epiphany. I pictured Alec Baldwin saying "ABC! A, Always, B, Be, C, Closing!" That's all our mentor ever did all night. He systematically found potential clients, assessed what they were interested in, followed up, and proposed a mutually beneficial transaction. He was always charming, and even when he went straight for the close, he sounded respectful and direct. While he did his rounds, his mostly-disinterested friends were providing situational intel and a bigger picture. Of course, most women were only interested in a small transaction, an exchange of numbers. Also, I was not interested in sex that night, and generally bad at escalating anything.

At 1:30am, we were all sloshed, and I hailed a cab. Our mentor looked a little disappointed in our inability to close, something he could have done 10 times for himself that night. Before he got in the cab, he showed us a list of about 25 phone numbers from the night and asked "Do you want any of these, because they gotta get erased." I said said I did alright for myself and got a bunch for myself." He nodded, said "okay, goodnight," hit erase, closed the cab door, and took off.

I later found out he was happily married and had a young kid. The whole point of the night for him was the chase. Even while partying, he was practicing his craft and his salesmanship. Perhaps this is obvious to some, but he showed us that you can get away with saying a lot more than social norms would have you believe, and he showed us that you don't have to close every time, and that you won't close very often, but doing volume means that you will close with somebody eventually, and while you're trying, you will get better through practice. He also showed that having observant posse and respecting their opinion is very important in getting a broader perspective on life and your business. Keep grinding.