Yury Molodtsov

COO and Partner @ MA Family, where we run communications for tech startups and VC firms.

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I Wish Bear Hadn’t Wasted Years

Bear emerged as the flagship notes app, but then lost its lead because of technical debt. I doubt their latest update makes them competitive right now.

July 20, 2023

Bear 2.0

Bear is a Markdown-centered note-taking app for the Apple ecosystem. It was first released back in 2016 during a very different era. Apple Notes were barebones compared to what they’re right now. They still used IMAP to sync your docs, a protocol designer for email with no support for differential changes! That’s why many people jumped from Evernote to Bear. It was slick, fast and kept your content portable.

Just recently, they released the long-promised Bear 2.0. Unfortunately, I think they lost most of their users along the way. See, the question of when the Bear 2.0 would come out became a meme in r/bearapp. Because it took the development team a few years to make this new updated version, while the original one barely changed.

During this time, one of the clear leaders in the notes space has turned into an oddity, still loved by its core users, but unable to get too much attention. We’ve seen tremendous improvements in Apple Notes and then the rise of the networked-thought like Roam Research and Obsidian, to digital-native document apps like Notion and Craft. And maybe it was largely a fad. But it’s hard not to see how far these apps have progressed.

Bear missed all of the excitement. And this makes me a little bit sad. I was a fan. I used it every day. But it was hard to stay loyal when I saw new shiny apps and everything they could have provided. I moved to Apple Notes, because even they were a bit better at some moment, and then tried a whole bunch of options, settling with Workflowy, until I ended up in Craft, where I’m drafting this post now.

Bear underwent this ordeal to radically rebuild their editor and enable things like tables and extended Markdown. It’s almost a case study on how tech debt might cripple your product. In some ways, they’re still catching up to Apple Notes. It’s great they’re offering a search for text on images, but Apple Notes got it in 2019.

Apple Notes

Comparing them right now, I see that Bear might have a few things going for it. First, links aren’t orange, which is a plus. And I truly love typing things in Markdown, even though it took me a long time to get there. Also, the only way to create a rich preview in Apple Notes is by sharing a link from Safari (which I don’t even use). There are always these weird and useless lock-ins with Apple products.

But at least with Apple, I know they will continue working on their app. In fact, both Apple Notes and Reminders are some of the most-improved apps in the Apple ecosystem (I know it hasn’t been true for all of them). On the other hand, Сraft has so much more to offer (even though it costs only a bit more annually). It’s a native app both on iOS and MacOS. It’s also centered on Markdown. And its pace of innovation has been tremendous. I specifically like the omnibar you can see in most apps right now, which allows you to switch between notes instantly. Or the ability to quickly share a note via a public link (the fact notes already look like beautiful websites helps a lot). To me, this is now table stakes.

Craft raised over $20M from VCs, which helps to employ a larger team. Still, they put themselves on a path of searching for more users and pricier use cases that (hopefully for them) leads to acquisition. I don’t know what will happen next. Evernote was bad before, but seemingly going to a crash after its latest acquisition. That’s why it’s important to be able to export your notes, and Markdown is a great format for this purpose. So many apps and tools can read it. There are two exporters for Apple Notes that allow you to get your content in Markdown, even with attachments. And then you can go anywhere. Worst case scenario, there always will be plain-text apps supporting it, like Obsidian.

Also, I’m not even sure I need to keep all the notes I ever drafted in my current app. As Dan Shipper noted:

It turns out that I am rarely in a position, while writing or thinking, where I want to glance through lots of old notes as a way to figure out what to say or do. Mostly that feels like sifting through stale garbage.

Writing things down is often more important than the act of storing them. I want to preserve my journal or lists of good places to visit in certain cities, but most of the other stuff, personal and work-related, is quite ephemeral. It’s almost like the message history with your friends. You think you want to preserve it, but if you actually scroll to the beginning of your friendship all those years ago, you’ll cringe a little.

There hasn’t been a better time to note applications and your choices are almost limitless. I like how the Bear team built a business around an artisan app for the Apple ecosystem. Not many people try to do it these days. If you want a simple note-taking app, Apple Notes will likely fit your goals, but if they don’t, try Bear.


Things 3, my favorite task manager, has basically the same problem. Its subreddit is filled with questions about the next version, it hasn’t received any meaningful updates, yet still lacks proper support for recurring tasks or attachments. In some way, Things 3 and Bear are very similar, as they have their cult followings due to their uniqueness on the market.

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