This great article by Alison Lobron explains so much about the connection (or non-connection) between making friends in the real world and the online world that I felt compelled to share some thoughts it spurred and it urge you to read the whole article. http://www.boston.com/lifestyle/articles/2011/03/13/turning_online_friends_in... For me, it helped explain some of my own behavior that I thought was odd, but now I understand. Example: no matter how much I should know about someone before I meet them, I've always avoided Googling them in advance. I'm not lazy. I just didn't feel like it was the right thing to do. Now I understand why. Instead of creating assumptions built on what I've read in advance, when I actually talk with the person, I'm building a friendship through what we each share. And, as the article points out -- we don't end up having to overcome the awkward situation of "knowing too much." The article provides some great background from one of my investments, now called stomp.io (which began life as SparkCloud.com) Designed by Nick Tommarello, stomp.io seeks to get people to meet in real life, share real life adventures, and let real life take it from there. Nick and I have had many conversations about how different the idea of making real life friends via the Internet is from making the virtual kind. It's refreshing and rewarding to see so many of the things we discussed outlined so clearly in Lobron's article. Recently, another company that I've invested in and worked closely with, GreenGoose, launched at Jason Calacanis' Launch Conference. Things took off fast and soon we had a very notable group of investors. One is Jay Levy from New York. I recently had a discussion with him about GreenGoose, and I had similarly avoided doing my "homework" on Google. We had a great conversation, and I learned what I know about Jay first hand, because he told me. Gosh, that seems like a really great way to get to know someone!