I like Matt, he's both a caring guy and a sensitive guy. As a sensitive and caring guy myself who tried the CEO thing, I think sadly, those are not particularly useful "top qualities" for that job.
I very specifically used the words "top qualities" - I'm not disputing they are quite important, but being overly caring about certain things or overly sensitive about certain things are not what should be number 1 or 2. In all the CEO's I've invested in over the years, I find when they get in sticky situations, it tends to be they're over expressing these two qualities in a situation, they are caring tooo much about something or being overly sensitive about something. I think right now, he is caring too much about something about being too sensitive about others, and having seen matt thru the years and dealing with Automattic at DigitalOcean, can't say I'm surprised. Like I said, I like matt, he's just not always the most.. level headed dude in my experience.
