There are definitely phases. Managing 20 or 30 people feels a lot different than managing a hundred or more. Up until about fifty, you can keep that family\team

There are definitely phases. Managing 20 or 30 people feels a lot different than managing a hundred or more. Up until about fifty, you can keep that family\team feeling that you're all in it together. You know everyone, and they all know each other. But somewhere a few months after a typical A-round, you start walking through the hall and wonder who the hell these people are? Who hired them? Do they really have the company's best interest at heart, or are they just freeloaders? Probably related to this, around that size you start to get the more toxic kind of politics. You realize people have agendas that they don't admit. The first rule of Fight Club... I think another way of describing what he calls loneliness would be paranoia. People put so much faith in their leaders, and they are so let down when they think you failed them. The term emotional roller coaster just doesn't do it justice. It sometimes feels more like you're in a blender. Strangely enough, I plan to do it again. But I think I'll tap out around that phase change if we're lucky enough to get there. It takes a whole different type of human being to take a company from a few million in sales to something impressive enough to make investors really happy they invested in you. It's certainly not for everybody.