Today I met with a young venture professional who spent far too much time figuring out why thought leaders would even want to meet with him than he actually spent just asking them to meet.  When I asked how many startup investors, for example, he had asked to meet in the last two weeks, he replied, “Well, none.”  Ok, then don’t tell me they won’t want to meet with you until you get turned down. 

This just happens far too many times.  People reach out to the nearest, most convenient people they know in their network, but never really reach out at any kind of scale to build connections.  I can’t tell you how many times I ask a company or a potential hire whether or not they’ve reached out to a certain person and the answer is no.  It’s a bad signal, too—makes the person seem less ambitious, and less willing to take initiative.

Don’t underestimate people’s willingness to share time for a relevant, interesting conversation.  Just ask.