I recently read Fred’s post about his fifteen years of blogging and tweeted about why I admire Fred’s blog:

I think of Fred as an “old school” blogger, and that’s a compliment. He prioritizes writing regularly over polish. His writing is idiosyncratic. Some posts encapsulate decades of hard business lessons, some posts are about deeply personal milestones, and some posts are about last night’s Mets game. Occasionally, Fred just posts a video. Some posts are mundane and some are revelatory. I like this style of blogging because it gives you a broad sense of the actual person behind the blog, not a lopsided view based on a specific professional agenda or personal interest. I wish more people blogged this way.

I realized after reading Fred’s post that I, too, had been blogging for 15 years in one place or another and writing publicly for 17 years, and that got me thinking about the critical role of writing generally and blogging specifically in my professional career and personal life. (This is a long post because I had never really thought about it in totality!)

2003-2005: My InfoWorld column and the dawn of blogging (for me)

Most people know me through my work at Etsy (and maybe even Yahoo!) but before all that, I  had a “real” writing gig. I joined InfoWorld in April 2001 as CTO doing actual CTO work but when they noticed I had an English degree and decent writing skills, they asked me if I would write a column for CTOs. At the time, the CTO was their prime target audience. I signed up to write a weekly column at InfoWorld called “CTO Connection” (somewhat still findable via Google) that ran from June 2001 to August 2005.

I had never done anything like it before. For 4+ years and 200+ columns, I had a strict weekly deadline to deliver 580 words to the copy desk — strict word count and deadline because the column was published in print (it had to fit on the printed page) and the presses rolled at a certain time whether you were ready or not. (I never missed press time because you simply did not miss press time!) I came up with the topic every week based on what was going on around me and never really lacked for topics to write about. The words came easy some weeks and some weeks were excruciating. I built a passionate reader base at the time and regularly got fan mail and a good dose of hate mail (one known trick for creating a fury was to criticize Apple). My boss was occasionally cc’ed on the emails, particularly the ones where a reader said my column was so off-the-mark that I should be immediately fired both from my writing gig and my operational CTO gig. The feedback was constant and I learned a lot from it, not the least of which was how to handle constant, sometimes aggressive critique from the outside world while staying focused and keeping my head on straight. This came in really handy later in my career.

My real blogging career began in January 2003 when I launched a blog at InfoWorld (part of IDG) as a way to break out of my word count restriction, respond to points raised in reader mail, talk about random things of interest that popped up, and connect to the CTOs who were reading my weekly column.  Remnants of it are available at the Wayback Machine. I jumped right into blogging with no fanfare or even recognition that I was blogging. My first post was about benchmarking Apache. My second post was about a redesign we did and how InfoWorld was now running on Linux on cheap Compaq DL360s (and I mean really cheap — we bought them for pennies on the dollar from the partly-IDG-funded Industry Standard when it imploded not long before. I personally unloaded them for our sysadmin’s van.) Notably, those first two posts were on a Saturday and Sunday, which was truly radical for what had been a weekly print publication: no gatekeepers, no copy editors. The words went straight from my head to the blog. (Incidentally, Blogger was acquired by Google just a few weeks later, so it was a heady time for blogging.)

I continued blogging and even started a podcast at the very end of my time at InfoWorld (around spring 2005) though it only ran two episodes before I left for Yahoo. In the two episodes I produced (I did all the recording, production, and editorial), I would talk to a working CTO about their work and then some unique interest, often shared. With my friend Jon Williams (then CTO at Kaplan Test Prep), we talked tech and a little about playing guitar (here’s the mp3). And in the second episode with Mike Dunn (then CTO of Hearst Interactive), we talked about surfing (though this episode is sadly lost to history). I developed a lot of productive and fun personal relationships with CTOs in every industry during that time, from startup CTOs to Fortune 50 CTOs, and I still keep in touch with many of them. None of that would have happened without the writing gig. I learned that writing publicly can help build long-term relationships.

2005-2008: A special time at Yahoo! and finding the love of my life

When I joined Yahoo in summer 2005, I announced it on my new blog on my personal domain. One of the things I learned from my time at InfoWorld is that owning your own domain was the only way to truly own your voice forever and my new personal blog was the recognition of that. Yahoo! also had an astoundingly liberal personal blog policy (PDF) that was more or less “anything goes” at a time when a big media storyline was “Person gets fired from company for blogging,” like this one. While I was at Yahoo, I ran the Yahoo! Developer Network and posted on that blog, too. Even in my corporate blogging, I tended to obsess over both the content and the headlines (like this one: “Smells Like Dunkirk Spirit” about the travails of a Yahoo Hack Day in London that was weirdly interrupted by storms that caused it to actually rain indoors). Still, my personal blog output dwarfed what I put into the corporate blog. My fairly regular personal blogging from that period turned out to be a nice historical archive of some really interesting times at Yahoo. What seemed like mostly a side hobby then has become a treasured record of a special time for me, professionally and personally. I’m grateful that I took the time to do that, and on my own domain. When a book came out several years back that featured a detailed chapter about that time at Yahoo! and my and others’ roles in it, those posts also came in handy to help me recall some of the best stories and anecdotes from that period. And during that period I captured the two best stories of all: getting engaged and ultimately married to the then and still love of my life.

2008-2011: Moving to NYC and being CTO at Etsy

In 2008, my friend Caterina Fake (herself and “old school” blogger) introduced me to the Etsy team and, long story short, I announced I was leaving Yahoo! and going to Etsy to be their CTO in July 2008. You can see my excitement at moving to NYC, an excitement that has not waned even a little in the decade of being here (as I quoted John Lennon in that post: “what a bad-ass city!”) There was a companion post on the Etsy blog (then known as the Storque!) and a couple of weeks after I started in September 2008, my first communication with the Etsy community as CTO was also on the blog (executive summary: things were in bad shape and we had a lot of work to do). It’s easy to look back at Etsy today and see its success as obvious and pre-ordained but it certainly didn’t feel that way when I wrote that post. The site was crashing more or less daily at the time. In the macro world, Lehman Brothers infamously collapsed into bankruptcy just the day before that blog post. I had been in NYC for two weeks and had just stopped sleeping on an air mattress when my boxes arrived from California. There was a part of me that thought I had truly terrible timing — why did I move to the center of the collapse of the financial system for this? My memories of that time were less of the “I’m so excited about this challenge!” variety and more “what have I gotten myself into?” Reading that first post today, I can feel the underlying anxiety of the time — how many incoming execs use a “ticking time bomb” metaphor in their inaugural posts to their customers? But I was glad to have a blog where I could tell the truth and start to get to know the community. The blog was a great vehicle for that kind of writing and blogging was a really natural form of direct communication to me at that point.

We had a big rebuilding job to do at Etsy and blogs came to the rescue in another way. We used a blog called fix.etsy.com to communicate during outages, which were very frequent when I first arrived. Ironically, the first major outage happened the day after my “ticking time bomb post” and fix.etsy.com itself was down so we had to bring that back up quickly to even be able to give updates on the main site outage (this moment is preserved in the Wayback Machine). Thank goodness that one of the beautiful things about a blog is you can get it up and running and start publishing almost immediately. I was at a bar with an important recruit during that first outage and was excusing myself regularly to manage the situation from the bathroom. (The recruit must have thought I had a medical problem giving how much I was going to the bathroom.)

In my first year or so, we had to take the site completely down for 4-6 hours per week almost every week to fix some core issues (as mentioned here), and fix.etsy.com was the critical line of communication. The tone of fix.etsy.com was very much “just the facts” (“8:00am: Etsy is currently unavailable and we’re working on it”) but I felt genuinely bad about what the community had to endure during that period so we tried to make the pain at least a little more entertaining. Back then, Hulu had a bunch of free movies you could embed on web pages and I noticed The Godfather trilogy was available, so I once raised the idea of offering parts 1 and 2 on the “we’re down for maintenance” page for the simple reason that they had an almost even six hours run time. We had a lot of time to fill while we did the work and people get bored waiting. We smartly decided that Etsy seller videos on a loop made more sense. Even this simple status blog had a community feel. When one of our key ops engineer’s wife went into labor, we had to cancel scheduled downtime and posted the news and a baby photo on the blog. The Etsy community of sellers could be tough but always with an underlying sweetness and I remember this moment being celebrated. (Celebrating the birth of a baby on an announcement about site outages somehow so perfectly captures the Etsy ethos of the time).

As engineering started to gain momentum, the constant firefighting started to recede into history and we had more interesting things to talk about than just keeping the site up. In February 2010, we conceived of and launched the Code as Craft blog (still running strong) when I published the first and second posts along with the About page. In the early days, I acted as kind of an editor-in-chief and encouraged engineers to write the kinds of posts they wanted to read and I promised we wouldn’t put it through a PR filter. Every engineer had a distinct voice and I wanted to bring it out. I was also being very pragmatic. I knew the blog could be a great recruiting tool and that engineers can smell bullshit 1,000 miles away. We kicked off the Code as Craft speaker series later that year with Fred Brooks, one of the legends of computer science. The work we were doing, the blog posts with the voices of real engineers, the amazing speakers, and the work itself was a key driver of the recruiting flywheel we built at the time. The Code as Craft talks sold out in minutes, people had fun and learned a lot when they visited the office, and everyone we interviewed seemed to come in knowing what we were all about just by reading the blog. Code as Craft turned into a very strategic recruiting tool for the company. It was also really fun and a badge of honor and rallying cry for engineers on the team. When I left my CTO role to take on the CEO job at Etsy, I passed the engineering torch to Kellan and John on the Code as Craft blog and entered the next chapter.

2011-2017: Being CEO at Etsy during a time of massive growth

Enter blogs again. When I made the transition to CEO, I announced my new role on the Etsy company blog with a story about Mary Haggerty, an Etsy seller I met in an unlikely place. Then I continued to post various updates throughout the years that mark key moments of my six years as CEO — a period where Etsy grew immensely by every qualitative and qualitative measure you can think of. Etsy used to publish a “weather report” with key company data so I’m able to see in the archives that in my first month as CTO at Etsy (September 2008), everyone was excited about breaking the $300,000 sales mark in a single day and $7.93 million in goods were sold that month. By the time I left in 2017, our run rate was ~35x that. During that period, I wrote a guest post about recruiting and culture for Fred’s “MBA Mondays” series on his blog. Generally, though, I found it harder to write as regularly as a CEO, but I did find a little time to write, like this post where I had a key insight about Peter Drucker and culture change that was just dying to get out. And once you’re leading a public company, your communications as a CEO and duty to a variety of stakeholders make any communication from you potentially fraught (just ask Elon). That made the off-the-cuff, no-gatekeeper style of blogging that I enjoyed much more difficult so my personal blog went largely dormant at the time.

When my time was up at Etsy, I wasn’t able to say any final words via Etsy channels but the archive remains and I’m grateful to be able to look back and remember how the company developed and grew in the nine years I was there, from my “what have I gotten myself into” early days of intense tech pain to leading a publicly-traded company (its own kind of pain but I think of it as perhaps more noble “pain at scale.” Ha. Sort of.) It was an extraordinary time in my life and every day I think of some new reason to appreciate my time at Etsy.

2017-present: Going solo. . but not really

Post-Etsy, I was professionally unaffiliated for the first time in my working life. The most common question I got was “what are you going to do next?” My blog had been largely dormant but I had still been maintaining the domain. I realized that the blog gave me a means to (in more traditional PR terms) “put out a statement” to answer the “what’s next?” question once rather than answer it a bunch of times in email. So I wrote a blog post and tweeted it out. It felt good to have no gatekeepers again. Then I updated the post in September as my sense of what the next stage of my life was going to look like came into focus. I haven’t really been “solo” during this period as much as I’ve been working differently, i.e. not just for one organization but for many. Since my “what’s next” post I have developed a nice coaching practice working with Reboot and have been enjoying being closely involved at Cornell Tech (got some interesting stuff brewing there – stay tuned). I’m more active in my non-profit board roles at St. Ann’s Warehouse and The Jalopy Theater and School of Music. I have been able to spend time doing the deepest thinking and reflecting of my life and have a backlog of things to write about. I started a newsletter last year that went dormant when the coaching business suddenly took off so I might get that going again. We’ll see.

So much of online writing today is about short-term “hot takes” and pursuing claps and virality but I’ve learned over seventeen years of writing publicly that one of the key benefits of writing online is that it supports your own memory.  A blog post provides a contemporary voice — yours — from a specific moment that doesn’t generally allow you to either glorify or denigrate lived history any more than it deserved at the time. It’s life as it happens. Blogging is also a way of laying the groundwork for the path ahead and creating virtual checkpoints to later reflect upon to get a sense of the progress you’ve made. That’s a long way of saying that I think I’ll be doing this for a while longer.

Writing this post made me realize again how valuable archive.org is to the Internet, so I made a donation. If you feel the same way, here’s how to donate.