Why I sold Doorkeeper

この記事は日本語でもお読みいただけます。

I can pinpoint the exact time when I decided to sell Doorkeeper, the event management platform I helped launch in 2010, incorporated in 2013, and made profitable in 2016. It was a Friday morning, and I was looking after my two-year old who was home sick from daycare with a 40°C fever.

A sick toddler isn’t an exceptional event. The PagerDuty alert that I received that morning thankfully was. One of Doorkeeper’s Kubernetes masters was acting up, and needed my attention. Two of my very different kinds of children demanding my attention at once, it seems comical in retrospect, but at the time it was overwhelming.

I got through the day, resolved the issue before it impacted any of our customers, and my kid went back to daycare the next week. But it left me thinking that once my second (human) child was born this kind of thing was only going to get more common.

Running my own business has given me incredible freedom. That I could take time off from work to look after my sick toddler in the first place, without having to get approval from anyone else, is an incredible privilege, and I’m grateful to all the Doorkeeper customers who helped make it possible.

If Doorkeeper was my only business, it would be a no-brainer to continue on through the tough times, and reap the many benefits of owning a profitable product. But on top of all this, I have another business, TokyoDev. Much like Doorkeeper, it started as a side project, just a personal blog about life in Japan. But over the years, it’s morphed into a job board that’s been very successful at helping international developers get jobs at Japanese companies. Not only has it grown to the point where it alone would be enough to support me financially, but it’s also been incredibly rewarding to be able to see the very real effect it’s had on people’s lives, with many developers getting their first job in Japan because of it.

Of the two businesses, TokyoDev seemed the more sensible one to focus on given my current stage of life. I’ve designed it to be as technically simple as possible. No servers, just a static website. Nothing that can break unless AWS’s S3 or CloudFront goes down, in which case I think I’m entitled to go down too. A relatively small customer list, but one where I can provide high value to each one. Pretty much the ideal bootstrapped business.

An exit from Doorkeeper seemed an attractive way of simplifying my life. Who’d have the desire and capital to purchase it, and the technical knowhow to run it though? There was one name that I’d had in the back of my mind, Jonathan Siegel.

The first time I met Jonathan, we didn’t get much of a chance to talk, but it was still pretty memorable. It was at an event I helped to organize in 2013, Tokyo Ruby Kaigi 10, which happened to be hosted on Doorkeeper. If I recall correctly, he was here on holiday, and decided to check out the local Ruby community. He’d always loved the language, using it to build his own business, and then later acquiring the businesses of other Rubyists.

When Jonathan moved to Tokyo, he continued his entrepreneurial activities, including co-founding an e-signature product focused on the Japanese market. I met with him a couple of times, including regarding sponsorship of a Tokyo Rubyist Meetup event I organized. During our lunch, he very casually offered to buy Doorkeeper from me. So casually I wasn’t actually sure if he was serious. Nevertheless, I wasn’t interested in selling the business at the time, so it didn’t go any further.

Now that I had the motivation to sell though, going back to Jonathan seemed natural, so I sent him an email. Two days later, we had a Zoom call, which ended with an offer. A couple days later we had a signed letter of intent. A month later we had closed the deal.

Everything went as well as I could have hoped for. Part of me kept waiting for there to be some catch, and us getting into conflict with each other. But that never happened, and his side was reasonable throughout the whole process.

Jonathan has told me that a big part of why he invested in the acquisition of Doorkeeper was to become more involved in the Japanese entrepreneurial and technical scene, and make further inroads into the Japanese community. Given my experience with him and his team so far, I believe that’s an honest sentiment, and that Doorkeeper is in good hands.

Going forward, John Cross will be the new General Manager of Doorkeeper. He’s been my main point of contact throughout this acquisition, and I have also had a great experience working with him. A Fukuoka resident, he’s happy to talk with any of Doorkeeper’s users about the future of the product. You can reach him at [email protected].

After having Doorkeeper be such a part of my professional identity for so long now, you might think selling it would be bittersweet. It’s not though, as I feel that it was unequivocally the right decision, both for me personally, and the future of the service. I’m excited to see what John and his team have in store for Doorkeeper, and look forward to watching my child from afar as it continues its life independent of me.