My Complicated Relationship with No Longer Being CEO

It’s been 22 months since I stepped down as the CEO of Moz and turned over the role to my longtime Chief Operating Officer and close friend, Sarah Bird. Since then I’ve recovered from depression, traveled to and keynoted dozens of events, started (and now nearly completed) a new product with a small team at Moz, and kept up my…

The False Narratives We Tell Ourselves

I carry a story around in my head. It’s not a true story. But it’s a story that’s hard to escape. It goes something like this: I started a company with my Mom when I was in my early twenties. We made lots of mistakes and went deeply into debt. We didn’t tell my Dad about that debt, so we…

On Being Wrong and Not Knowing the Answer

There’s the naive view of expertise – the one that we all have as young people – where we think that Eddie Vedder must know absolutely everything there is to know about rock music and Peyton Manning must know more than anyone else about the game of American Football. And then, there’s the more nuanced view of expertise we all…

A Long, Ugly Year of Depression That’s Finally Fading

Yesterday morning I woke up early to speak at the Business of Software conference in Boston. It was my first time there, and it’s an exceptional group. Then, after some meetings, I spoke in the afternoon at Hubspot’s Inbound conference (thankfully just across a long skybridge that connects Boston’s World Trade Center from its Convention Center). This morning, I woke…

Elite Privilege, Ivy League Schools, and Uncommon Advice for Building a Network

Geraldine and I don’t have kids, but for some reason, the last few months, I’ve spent innumerable conversations talking to our many friends with children about the tradeoffs of public vs. private schooling. As is my nature, I couldn’t help but research the topic on the web. And in nearly every piece I read, the same few messages emerge: Private…

The Dichotomy of My 2013 Told Through 29 Photos

As I write this, it’s New Year’s Day. It’s a holiday, and I shouldn’t be working. I should be doing things that make me happy and bring me peace and joy. I’m in Palm Springs, California with Geraldine and Sarah and Eric (and their 2 year old son). We rented a house with a small pool out back, and have…

Can’t Sleep; Caught in The Loop

During the worst weeks of this year, I’ve had this weird mental cycle that, despite being incredibly exhausted, keeps me awake. In my head, I’ve taken to calling it “The Loop.” (photo credit: Geraldine in Paris) The Loop starts out with something small. I’ll be lying awake, in bed, trying to fall asleep, and thinking (as I do most of…

Swapping Drivers on this Long Road Trip Together

2013 has been a really hard year for me. In many ways, it’s been harder than even the 2002-2006 era when my Mom and I went deeply into debt and worried about paying the rent and being chased by creditors. Some of that is attributable to the less-than-what-I-hoped-for results the business achieved (mostly because we artificially constrained our acquisition funnel…