A version of this essay was published as part of my monthly newsletter a couple weeks back. Find other archives and join here to get updates like this first.
Nobody wants to follow someone who made General in peacetime.
I’ve been thinking about that concept a lot lately (Ben Horowitz calls its Peace/War Time CEO). In 2017, after eight years of informally leading the tiny community journalism organization I cofounded, I named myself CEO. Up until that point, my cofounder Brian and I had survived together. We’d always find a way to last a bit longer, growing slowly and thoughtfully as we navigated treacherous waters.
That survival approach was rational for growing a local news company in the early 21st century, a time in which consumers maintain very high expectations for free and independent journalism but have not yet been fully trained to actually pay or otherwise support its work in a post-advertising world.
But in early 2018, as I was finally feeling the great responsibility of the CEO title, I took stock of where my company was.