Automattic Acquires Day One Journaling App

Automattic has acquired Day One, a journaling app available on iPhone, Android, iPad, Mac, and Apple Watch. The app makes it easy to create journal entries on the go, offers end-to-end encryption for privacy on its paid tier, and has offline capabilities. While most users compose private entries, Automattic’s acquisition announcement promises integrations for publishing to the web:

That doesn’t mean that everything you journal has to stay private, though. When you want to share specific entries – or even entire journals with the world – you can expect seamless integrations with both WordPress.com and Tumblr to do just that. On the flip side of that, importing your favorite content from WordPress.com and Tumblr into Day One is on the near-term roadmap.

In a post on his personal blog, Automattic CEO Matt Mullenweg said he has been a user of Day One since 2016 and spoke highly of the app’s infrastructure:

Day One not only nails the experience of a local blog (or journal as they call it) in an app, but also has (built) a great technical infrastructure — it works fantastic (when) offline and has a fully encrypted sync mechanism, so the data that’s in the cloud is secured in a way that even someone with access to their database couldn’t decode your entries, it’s only decrypted on your local device. Combining encryption and sync in a truly secure way is tricky, but they’ve done it.

A journaling app is a surprising acquisition for Automattic, which has traditionally gravitated towards snapping up publishing-related companies and tools. WordPress is capable of powering nearly every kind of public-facing website, but private publishing has never been its strong suit. Though many have used WordPress in a sort of “private” mode for journaling, or set up local installations, the software is not streamlined for this particular use case. Day One expertly handles this niche that has remained relatively untouched in the WordPress ecosystem.

In explaining the acquisition, Mullenweg also touched on his “vision of making Automattic the Berkshire Hathaway of the internet,” a notion shared by Tiny Capital and often applied to Alphabet and its diverse holdings. One distinction is that Automattic’s acquisitions tend to complement one another technologically, often introducing the potential for improvements that can be shared with other products through open source software.

Day One Community Remains Trepidatious About the Acquisition

Why did Automattic buy the company? Day One customers are curious, as some of them perceive Automattic to be another “corporate giant” gobbling up a scrappy startup, ready to squeeze every possible drop of revenue out of the app’s loyal customers.

Many long-time Day One users have never heard of Automattic and they are understandably leery of seeing their beloved app change hands. Perusing the comments on the Twitter announcement and in the app’s community on Facebook, the news has precipitated a stream of cancellations and exports as users explore alternatives. Numerous customers were disheartened by one particular ambiguous statement in Day One’s announcement, which left the door open for future changes to the privacy of the app:

Rest assured there are no current plans to change the privacy of Day One; safely protecting memories and creating a 100% personal space is the foundation upon which this company was built.

The statement has since been updated to be more reassuring to users, although it still doesn’t explicitly promise no changes. It does contain a hint at why Automattic was interested in acquiring the app:

Rest assured that Day One’s commitment to protecting your privacy remains unchanged. Safely protecting memories and creating a 100% personal space is the foundation upon which this company was built. (In fact, our technical capabilities around privacy are a large part of what Automattic finds valuable in our company).

I have never seen a more engaged community with such a strong reaction following an acquisition. Many are deeply invested, having poured years of their lives and private memories into Day One.

“Oh, great. I find a journaling app I really like and have 10 years of entries invested, and they get gobbled up by a bigger fish,” one user commented in the app’s Facebook community. “What will become of our beloved app? Will the safety, security, and integrity of our data be assured? Time to back up all of my data local.”

Users have concerns about Day One’s updated privacy policy and whether the company might share data with affiliates. Many embraced the app because it was free of any ties with social media platforms. They have sewn themselves into this app in the most vulnerable way, and they are worried about how their private data will be handled in the future. Automattic may have a long road ahead in easing customers’ concerns so that they don’t feel the pressure to export and look for alternatives.

As someone who considered using Day One years ago, I think I would be more likely to use it now, knowing that Automattic is usually in it for the long haul. I passed on Day On at the time because apps come and go and it’s not always easy to predict which ones have the right business model to stay afloat. One of my worst recurring nightmares is that I accidentally throw away my paper journals or that my house burns down with my journals inside. Putting trust in a company to keep your electronic data safe and private is an intensely personal decision.

Knowing that a larger company with more resources is behind Day One, along with leadership that bears a genuine appreciation for its underlying tech, it seems like a safer pick for a journaling app that will be around for the next ten years. The company’s founder and CEO Paul Mayne will continue to lead his same team at Automattic and is convinced that the move will be beneficial for “the preservation and longevity” of the app. Given how passionate Day One’s user base is about protecting the app’s future, I’m eager to see how Automattic handles the challenge of winning their confidence.