Why I’m launching a newsletter

I announced on Twitter that I’m launching a newsletter. It’s called Chad Dickerson’s Fieldnotes (more about the inspiration for the name). I expect it to be roughly monthly starting later this month. Subscribe here. Some people have asked me why so I thought I’d explain.

In general, I plan to be writing a lot more and the newsletter is part of it. My vision for my newsletter is a focal point for all of my writing (on this blog and elsewhere) while aggregating and commenting on some of the interesting things I find along the way. Topics will include business, music, books, culture, what I’m up to, and what I learned as a CEO and CTO. I have a lot to say and I’m excited to be able to say it as a free agent with a high degree of editorial independence.

My time at Etsy was also very profound and there are lots of insights from that experience that I haven’t had a chance to lay out yet. Writing is a great way to process and refine one’s thinking. Very few people have the chance to take on two major executive roles (CTO and CEO) in a company like Etsy from building a team and rebuilding a platform as a startup CTO (the proverbial changing of the jet engine while in flight) to leading a high-profile public company as CEO and Chair of the board. I did that and I’m confident that I took that path in a way that was true to my self and to a set of larger principles. I know other people are trying to do the same thing and I hope some of my writing will give them insight and strength.

Many people reach out to me and want to talk about Etsy as a socially responsible company. I will certainly write about that, probably a lot and in a very pragmatic way. Socially responsible business remains a passion of mine. That business orientation was super important to me in my time at Etsy but I also think the focus on that aspect of Etsy can obscure the sheer improbability of *any* venture-backed company making it through all the stages we made it through at Etsy. In my time there, Etsy wasn’t just special in a cultural sense, it was very special in a pure business sense. If you look at this CB Insights analysis of the cohort of companies who raised seed rounds in 2008-10, only 5 out of 1098 had a $1B+ exit. 3 of those went public and 2 were acquired. These kinds of odds are astounding for any company, much less a spirited and unconventional company like Etsy. We were doing a lot of things that simply hadn’t been done before or even attempted. (Oh, and we also faced down Amazon in the process. No big deal. When the New Yorker visited one day, the headline of their story was “Visiting Etsy, Amazon’s Next Prey” and SNL Weekend Update had a great bit on the competition around the same time — see 2:45 mark in this video)

I wrote a lot while at Etsy and always always loved doing it. A few still take me back to the moment I wrote them as if it was yesterday. Only two weeks into my arrival, I wrote about the massive challenges I immediately encountered as CTO in September 2008. I wrote the first post and the About page on the Etsy engineering blog, Code as Craft. I wrote about my long-term vision for Etsy in May 2012 as CEO when we became a B Corp, dropping a reference to fellow Brooklynite and (I think) Etsy kindred spirit Walt Whitman. When we went public, I wrote a post referencing James Joyce and quoted Ovid. I was never doing this to be a pretentious show-off. My view of the world is just very integrated. Liberal arts, tech, art, business, technology, literature, music — they are all connected and the more we make connections across all of those disciplines, the better we will be for it (side note: who among us isn’t wishing that tech leaders didn’t have a stronger handle on ethics, gender issues, history, and politics?) Expect that to come through in my newsletter and this blog.

So, if you’re looking for business advice neatly prepared into one-size-fits-all hermetically-sealed listicles, prepare to be gravely disappointed. If you want pragmatic insight into business from someone who experienced a lot and you also appreciate the occasional link to a video of the very last Sex Pistols show at Winterland in SF in 1978 or Orson Welles interviewing Andy Kaufman or an illustrated guide to Guy Debord’s “The Society of the Spectacle,” I’m your guy.  (Subscribe here.)

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