Why Taking Random Meetings Matters So Much

This evening, just a couple minutes ago, I took a meeting with someone for random reasons. I can’t tell you who or why, because it may be a big business opportunity for me, but I’m going to talk about it here because that’s just how I roll.

For all the black and white reasons, this may have been the worst meeting I’ve taken all year. Here it is, 8 o’clock on a Wednesday, I’m tired, I’ve got millions of emails, and I miss my wife. I went in with below-zero expectations, but I walked out with what might be the next giant step of my career.

So why do I do random stuff that looks like it has no ROI and takes up my time (which is arguably my single most valuable resource)? Because I think life is predicated on serendipity. Because I think life is who you meet. Because I think life is in the gray.

Back in 2009 I met with with a guy by the name of Chris Dessi who reached out to me and wanted to randomly meet. Everything about that meeting pointed to it being a bad use of my time, but it was through Chris that I met Mike Lazrow of Buddy Media, and it was through Mike that I encountered tremendous financial opportunity, even going on to launch VaynerMedia from one of his conference rooms.

Tonight I took a random meeting, and it might have been the most important one I’ve taken in years.

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