DreamHost CEO Simon Anderson is leaving after disagreements with board

In the world of hosting, there are the big players (like EIG and GoDaddy), lots of tiny companies, and a couple of handfuls of companies in-between. DreamHost is a tweener, that’s not huge, but not small, and has a fairly WordPress-centric platform.

Other than knowing that Mike Schroder and Mika Epstein (two important people within the WordPress community) work there, I honestly don’t know too much about DreamHost. I know they’ve sponsored a bunch of WordCamps, and not much else.

Yesterday, it was announced that their CEO, Simon Anderson, was stepping down after 5 years in the job, due to disagreements with the board. Despite this being somewhat of a force-out, or breakup, everyone seems to be on pretty good terms.

I talked to Mike about his CEO leaving, and he says Simon will be missed:

For now, the most I think I can say is that we’ll definitely miss him, and will have a democratic / feedback oriented process for our next CEO, which I think is great.

Looking into the decision, and Simon’s very forward Tweet about the board disagreements, I discovered DreamHost’s policy on what they call Shameless Honesty, which is really cool. From a 2013 interview he did with the New York Times:

You can be sitting in a meeting and you can say, “I’m going to be shamelessly honest here.” Boom. Now there’s respect and it’s not rude honesty. It just gives us permission to have those hard conversations and get to a point where the elephant is not in the room. We don’t have elephants in the room for very long because someone’s going to call it out and say, “Look, I’m not getting this.”


When people talk about culture, they often think that culture is about the lunches and that sort of thing. We don’t really see culture like that. Culture’s a full-contact sport. You’re fighting for what you believe in. Culture is debate. It’s argument. It’s messy, and for culture to be strong, people have to be fighting and challenging each other.

I love that this is a part of the culture at DreamHost.

Simon was also hired under a democratic process, where he narrowly beat out another candidate in an all-employees vote. Their next CEO will likely be brought in under the same sort of process.

I don’t have anything too grand to take away from this, other than I like what DreamHost is doing culture wise. I do, however, wonder if DreamHost is struggling by being squeezed on the bottom end and the top end at the same time. It’s not an easy time to be a middle of the road hosting company. The quality of the cheap options is getting better, and the top end (mostly managed WordPress world) requires a tremendous amount of knowledge and WordPress-specific support capability.

I wish Simon the best of luck in the future; I also wish I knew him better while he was at DreamHost.

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