I changed a lot at my company. Here’s why beating a big Q1 revenue goal meant so much

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.

Continue reading I changed a lot at my company. Here’s why beating a big Q1 revenue goal meant so much

How to fund small projects as a CEO

One unexpected result of becoming CEO of my own company is that I found myself without a traditional budget line I could pull from.

As we grew our company, we created a budget aligned with core functions. I stepped into a role in which I was overseeing them all, but I didn’t set aside budget for me in last year’s budget for myself. That sparked me to wonder how other CEOs approached giving themselves budgetary space to experiment, explore and trial.

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Lessons on “The Messy Middle” of business from Scott Belsky

You know startups. You know exits.

Most of the work of business takes place somewhere in between the very start and the very end. Yet a lot of media attention focuses on those two iconic poles. So you might know a lot less about the space between the two poles.

We need more guidance on the work stage. That’s the approach in The Messy Middle, a new book published late last year from Scott Belsky. He founded Behance, which sold in 2012 to Adobe for $150 million, and has been an active  investor.

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9 examples of substance from nine years of Technically Media

My thoughtful coworkers brought in to the office a young Ben Franklin impersonator to discuss entrepreneurship and civic good in publishing last month. It was perhaps the most fun celebration of the ninth anniversary of starting what became Technically Media I could ask for.

(For some reason, someone shouted out that we should only have serious faces in the above photo. Believe me, we were having lots of fun.)

Afterward, I did a little Twitter rant I thought I’d save here for posterity.

Continue reading 9 examples of substance from nine years of Technically Media

I am motivated by fear

A version of this essay was published as part of my twice-monthly newsletter several weeks ago. Find other archives and join here to get updates like this first.

Someone asked me recently what was the biggest motivator for me to start a company, and I told him it was fear.

That’s true, if still somewhat self-deprecating.

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