Startup CEO, 2nd Edition

Chapter 44The Importance of Peer Groups

It's often said that being a CEO is the loneliest job in the world. Fred Wilson describes it elegantly in a blog post from 2005:

I often look at a founder or a CEO, see the tired eyes, an anxious twitch in the cheek or a missing beat in their step and think to myself or say out loud to others – he's got the weight of the company on his shoulders.

Being the founder and/or CEO is heavy duty. To use another cliché, it's lonely at the top. . . . Most people, regardless of how well prepared they are for the role, will find being the leader to be a thankless role at times.

Everyone inside the company is looking to you for answers, leadership, direction, and on top of that, they want it with a smile and a pat on the back.

Try doing all that on a day when you find out that the numbers were awful the past month, that your CTO is leaving to do another startup, and your lead investor is giving you a hard time.

Frankly, it's a thankless task most of the time. Because who do they report to? A board, not a person. A board is a lot less likely to provide day‐to‐day management and support. Groups don't do that, people do. Unfortunately, a board is a group, not a person.

A great coach can help with this. So can a great board, acting as a group or as individuals. Quite frankly, so can a great management team or even an informal “kitchen cabinet” inside an organization. With all of those, something is missing. Even the most empathic boards or coaches, ...