I met Craig, of craigslist.com fame, once. It was at a Software Development Magazine Conference somewhere around 2002 (I think). I was a judge for the Software Development Jolt Awards, and Craig was the keynote speaker at the awards ceremony. After the event, everyone was standing around talking geek-talk (as we will do) and Craig was there standing by the stage. I walked up to him and complemented him on the bag he was carrying…it seemed like a practical and stylish accessory. He asked me what I really thought and “if it looks dumb.” His honesty and insecurity was so refreshing to me and I’ve been a huge fan of his ever since then. This is the guy who started Craigslist, but, he asked me for my opinion of his man purse!
Craig Newmark’s title at craigslist has always been “customer service representative” and he actually did (probably still does) the work of a customer service representative long after he could afford to pay many other people to do that job. He gave away his craigslist equity to charity. Today, he signed the “billionaire’s pledge”, on his birthday, vowing to give away all his money before he dies.
I emailed Craig again a couple years ago to tell him that he’s my hero and to thank him for being a real person (or something to that effect). I told him about the “man purse” incident. I shouldn’t have been surprised (but I was) that he wrote back. He said he still carries a man purse, and that it’s currently “a cheap Lululemon knockoff” and that he’s still asking if it looks dumb.
If you aren’t paying attention to and following Craig Newmark, I encourage you to. He’s not getting covered in the media the way that other very rich people in tech are — he doesn’t seem to want attention — but he’s making a difference and he serves as a reminder that powerful and rich people can choose to be nice too.