Negative Maintenance

I had a fun email exchange with an investor I’ve worked with for almost 20 years in response to something a CEO send out from a board we are both on. I said “fucking awesome.” He said “that’s an understatement.” I said “CEO is such a delight.” He said “CEO is negative maintenance.” I loved this. So I’m going to use this post to think through the idea out loud and I’d love your feedback since it’s still a messy / blurry concept in my mind. ...