How the head of Obsidian went from superfan to CEO

0:01Welcome to Decoder. This is Casey Newton, founder and editor of Platformer and co-host of the Hard Fork podcast. I've had a lot of fun guest hosting a few episodes of Decoder while Neelai is out on parental leave this summer. And if you listen to either of the last couple of Monday shows, you know I've been doing a series with founders who are focused on productivity. This is my third and sadly last time joining the show this time around. But I'm really excited about this episode because today I'm talking with Steph Ango, who is the CEO of Obsidian. Obsidian is a note-taking and productivity app that fits into a similar second brain space to Notion, whose CEO I interviewed here on Decoder last week.

0:47But Obsidian differentiates itself with a really unusual approach to its business. It still wants to be your entire personal knowledge base, so holding all of your notes and links and files and other information, but it works in a really different way. In Obsidian, files are markdown-based, they're stored locally on your own devices, and it's completely free to use. You'll hear Steph say he doesn't even know how many users Obsidian has or how sticky the software is, which is more or less unheard of among the startups I cover. Obsidian does charge a subscription fee for access to certain features, including cross-device sync, version history, and the ability to publish your notes to the web.

1:31But it's still a model that feels pretty old-fashioned for software that's trying to keep up with the modern world. And so I wanted to ask him about those decisions. Steph's role as CEO is also unusual because although Obsidian is still a very young, very small, and very flat organization, he's actually not one of the founders. He joined in 2023 when co-founders Shida Lee and Erica Hsu brought him in based on his experience with his former startup, Lumi, and he was also a huge Obsidian fan. So I really wanted to ask him about that, too, because I suspected the answers to the big decoder questions about organization and decision making were going to be really unusual for a decoder guest.

2:14And in one final interesting twist, I asked Steph why, when so many of his competitors seem to be racing to stuff their productivity products with AI features, doesn't seem like Obsidian is all too eager to follow suit. I thought his answer here was pretty illuminating. So that's Obsidian CEO Steph Ango. Here we go.

2:47stephano you are the ceo of obsidian welcome to decoder thanks casey i'm glad to be here what is obsidian how does it work and who is it for i guess obsidian is a note-taking app if you want to really boil it down. A lot of people use it for writing their thoughts, journaling. A lot of people are students who like to track their progress through school, do their research notes. There are authors, book writers, big fans of RPG games love to use it. It's kind of the idea that makes Obsidian unique is it sort of works like Wikipedia in that the core unit is a link between your notes. So if I was to write my experience today in my journal, I'd say, today I was on the Decoder podcast with Casey.

3:37And each time I mentioned something, I might form a link. So I might just say Decoder as a link. And it's okay if that link is not pointing to anything yet. But later down the road, I might create a note for Decoder because I want to track some of the interesting interviews I've listened to on that podcast. And so over time, your web of knowledge becomes greater and you have more different nodes in your Obsidian. But fundamentally, when you open the app, it works a lot like Apple Notes or Evernote or Notion or any other kind of similar apps out there. When you joined the company in 2023, you said, I can't overstate how life-changing Obsidian has been for me.

4:17It has fundamentally improved the way I think. I want to see what happens if more people gain that superpower. What do you feel like is the superpower that Obsidian gave you? and why did you feel like no other products had been able to make you feel quite the same way? Yeah, I mean, I've been writing notes, journaling for, I don't know, over 20 years and I've used a lot of different apps over the years. I think this idea of thinking of the world like your own personal Wikipedia was really powerful. And so I had kind of cluched together a few different apps to make something that kind of worked that way.

4:56There's a lot of wiki-based software that already existed, but most of it was designed around publishing a full wiki to the web as opposed to using it for your own personal notes. So as soon as it came out, the founders of Obsidian, Hashida and Erica, they had already kind of put in the level of polish to it that was not there in this kind of glued together prototype that I had. So it was instantly something that made sense to me. It made sense also because the way that the data is stored is in this very durable format that people can own, which is called Markdown. You get super fans of Markdown and people who've never heard of it before.

5:41So in the audience, I'm not sure who... I think we probably have a lot of Markdown users in the Decoder audience, but for those who maybe have not seen it yet, how would you describe it? Basically, the oldest kind of files that we have going back to the 60s are plain text files. And Markdown kind of takes that idea of a plain text file, which is just raw text, and allows you to add basic formatting to it. So if you want some text to be bold or some text to be a heading or a table or a list, it allows you to essentially use simple characters like punctuation marks to indicate what's going to be bold or italic, for example.

6:25But the power of that is that the data is stored in this very, very simple format. So we kind of have this view around your data that if you want to be able to hold your data for a long time and be able to read it maybe 100 years from now, or your kids' kids, your legacy, whatever it is, maybe none of their notes matter at all. Maybe they'll be curious. But what if that data could be preserved over the long term? we think that going back to some of the simplest formats that exist that give you that control over your data is going to be something that's more likely to persist over time. So that's one of our philosophies around that.

7:07Right. So going back to your question, yeah, I was really excited about kind of the principles, all of those different things coming together. and to the point of how it made me think differently, I think once you kind of have this concept of links and ideas that can be networked together, you can start to form more complicated or complex or interesting thoughts than you otherwise could. Because I don't know other people, but I can only have like two or three different ideas in my mind at once. But if you can start to create these little building blocks of ideas, you can combine them in interesting ways, and your ideas become like these little Lego blocks that you can interchange and mix together and start forming some really interesting and complicated thoughts.

7:53I would love to hear about an example of when you feel like you were able to do that in Obsidian. You've written online about your note-taking practice. You described it for us a minute ago, talking about how you sort of keep a daily journal, and as new characters and ideas come in, and you'll sort of link them, and those will kind of build over time. I'm curious about that next step of, is there a time when all of that added up into something that let you make something that maybe you wouldn't have otherwise? Definitely. There's things along the lines of projects I'm interested in. For me, even though I'm the CEO of Obsidian, I kind of see it as a means to an end.

8:31So I like to write. I write a lot of short essays on my blog, and a lot of the essays came from just sort of marinating in obsidian where I can kind of debate with myself whether an idea is good or not so I have this essay that I wrote called pain is information I was going through like a pretty tough time a few years back and I read this book by Murakami what I talk about when I talk about running and it's sort of this autobiographical story about running. And in it, I came across this quote that was, I'm just trying to remember this on the fly, but it's something like, you know, when you sign up for a marathon, you know that you're signing up for pain.

9:16But then the question is like, pain is inevitable, suffering is optional. So that idea was really interesting to me because I was going through quite a painful time. And I I was thinking about when you touch your hand on a stove, that gives you a signal that that's probably a bad idea, but that's information. And so I was starting to kind of think about information and pain and the relationship between those things. And you can see how like these ideas are just forming and kind of out of thin air, out of different inspirations that I'm going through. What I like about Obsidian is it gives you this place to approach it in a very freeform way.

9:55and connect different concepts that you might be thinking about. Now for me, it's kind of in this like philosophical realm, but for other people it might be biology or language learning or something else. My partner speaks Chinese and I've been wanting to learn Chinese and so I'm starting to kind of like bring together these different ideas. Or in my other hobbies, I'm into woodworking and I'm always learning new skills and new details, you know, new tools that I might want to use and I'm doing research about that. And all of those things can coexist inside of this like digital place, which is kind of weird because now you could have a connection between a woodworking tool and, you know, a city that I went to in China and the concept of, you know, that Murakami was describing.

10:44Like all those things are just ingredients in this soup and you could start to come up with ideas that are, you know, pretty, you know, that you just wouldn't have thought of otherwise. And maybe that's enlightening. It seems like something that a lot of people value about Obsidian and other apps like this is that they can be engines for serendipity, where you gather a bunch of string in the manner that you just described. And then in the process of clicking back through your notes or using other tools inside the app, you revisit ideas and they sort of spark new ideas or you see connections that you might not have otherwise.

11:20Yeah, definitely. And I think that one of the benefits of this approach that I'm describing is it's quite freeform. Like, I think what's difficult, what I run into when I've used other tools or other approaches in the past, whether it's like a physical journal, you're quite constrained by the fact that a physical journal is pieces of paper and you have to kind of flip through them. It's like got that, you know, limitation of being this like 2D surface or a lot of apps kind of have a concept of folders or tags. Whereas here, you don't have to know what something is going to be about until later when the connections form between each other.

12:00And you're free to have 700 tabs open inside of Obsidian and be doing this crazy, you know, it's always sunny mind mapping with the red thread everywhere. It allows you to do that in a way that It's something that has a more top-down hierarchy, makes it more difficult.

12:23We have to take a short break here. We'll be right back.

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14:13Tick-Tack. Refresh your good vibes.

14:21Welcome back. This is Casey Newton, and I'm talking with Obsidian CEO, Steph Ango. A lot of the CEOs running productivity companies like Obsidian are still founder or co-founder CEOs, but not Steph. He came in just a couple of years ago, and I really wanted to ask him about that.

14:41So you're not a co-founder of Obsidian. You were brought in as CEO in 2023. How did that come about? And what were you brought in to do? The app came out in 2020. And I found out about it pretty much in the first version. So it was right at the beginning of the pandemic. And I think all of us were going stir crazy. and I think that there was this moment in time where a lot of interesting tools popped up because everybody was like, all right, what am I going to do with all this extra free time and I'm hanging out at home? I started using it right away for the reason I described before, which was just like it made sense.

15:20And Obsidian is super customizable. So you can make plugins, you can make themes, You can modify it in really significant ways or small ways. So I was just starting to put all these community things out there. I was running a different startup at the time. And I was just putting these things out there because I was making them for myself. And people really started using them. Shida and Erica are amazing engineers who met at University of Waterloo. And they're geniuses in terms of engineering and community management. I think what I was bringing to the table as a community member was a sense of design and product that they maybe had a little less of.

16:06Because of how the community of Obsidian is so strong, some of the things that I was making were getting a lot of adoption and I was collaborating with other people in the community. And they found out about that and, you know, wanted to put a quote from me on their front page. So we started chatting and then we started talking about business and they started telling me about the business model and some of the challenges that they were dealing with. We just kept talking for a couple of years and I was using Obsidian all the time. It was just like the main app that I had. And so when I sold my previous startup, Lumi, I started to think, you know, what would be my next thing?

16:46I was thinking about building something else, you know, starting a new company. and I just was spending all my time in Obsidian using the app. And I was like, this is, I just have so much fun using this tool. So basically I pitched to them, you know, what if I could come on board and help you guys? At first it took the shape of just contract work, working with them, kind of advisory and working on the 1.0 release that had this new design that I built. And And eventually, they were really more interested in continuing, like Shida is an incredible engineer, one of the best I've ever worked with.

17:26And he just wants to focus on that. It created this nice balance. We're a really small team. I mean, we are seven full-time people. There's something nice about the balance of different strengths that we all have. Everyone can kind of do everything, but at the same time, each person has their core strengths. And I think for me, it's around design, kind of consolidating what is the true essence of Obsidian and trying to communicate it out to the world. And then a long tail of random, because we're only seven, a lot of hats to be worn, whether it's accounting, legal, all these random things. And I had a lot of experience kind of running a few startups.

18:10So that I think was helpful. You mentioned the ecosystem of plugins, and it seems to me that plugins have been one of the main ways that Obsidian has grown, both in its feature set, but also in building features that have attracted new users. So what was the origin of plugins, and how have they fueled the company's growth? Well, in a way, plugins is what allows us to stay small because, you know, there are so many capabilities that people want that are fairly narrow, that will only be useful to 1 % or less of our user base. And you see this all the time with apps that have been around for a long time, where the feature set just keeps growing and growing and growing.

18:59And then the app becomes uploaded and slow and hard to use. And there's just too much functionality in there. And for new users, it becomes extremely confusing. So I think initially, it was kind of this defensive move against having to implement all these features and just basically say, here, you go do it. And because it's built on web technologies like JavaScript and CSS, a lot of people know those languages and know how to build things for it. So you don't need to know Swift or like you don't need to be a cross platform app developer to know how to make a plugin. You can make something really simple, you know, in a matter of minutes or hours, depending on your level.

19:44So I think the initial reasoning was this will allow us to not build everything ourselves. But then just how many creative things people came up with is always pushing the envelope of what our API should be able to support and how can the platform allow even more flexibility. Because now it's just obvious that, I mean, out of a few thousand plugins that exist, there's only a small proportion that really makes sense to be in the core app. And some of them do end up becoming something we notice, 80 % of the user base is relying on one plugin. For example, right now we're working on this thing called Bases, which allows you to view your notes in a database-type format.

20:34And there are a number of plugins that do something like that in the Obsidian community. So it's a signal to us that actually this is really important, and it should come into the core app. What are some other plugins that have just been really, really popular or maybe took the app in unexpected but successful directions? Some of the most popular ones are very simple. They're things like someone who's on the team now today, Tony Grissinger, wrote this plugin called Advanced Tables, which was just a way to simplify making tables in Obsidian. So, I mean, we're just talking about something very basic, but rows and columns, it was kind of difficult to do earlier on.

21:15And especially if you're someone who wants to live completely in the Markdown world, they're kind of tricky to make. So we ended up hiring Tony and he built that functionality alongside Matt. It was another basically everyone who we've hired or work with was once a community plugin author or team developer. So it makes it really easy for us to start bringing the right people who are passionate about Obsidian on board. But yeah, there are plugins that are about deeming, styling, changing fonts and colors. A lot of people enjoy that customizability and they want to be able to make this journal space their own.

22:00There's a lot of plugins that have to do with integrations with other services. So if you want your calendar in there or something like that, you can do that. There's integrations into a million different apps and things out there. if you want to be doing your tasks and to-do lists in Obsidian, there's a whole bunch of plugins that help you with that. The cool thing about that is if your interest in Obsidian is because you want to do world building for your RPG tabletop, like DM group, you can do that. And you don't have to have like the entire calendar functionality inside of your Obsidian. You can just use the plugins and things that have to do with that.

22:44Plugins, I think, were really the first thing that brought Obsidian to my attention. I'd been using Roam Research, which I do give credit for inventing a lot of the current note-taking paradigm. But thanks to plugins, Obsidian just developed much faster. And I'm curious what you did to attract those first developers. Was it as simple as you just had a really good API that was available quite early on? Or what is it that the company did? Yeah, I think it's a combination of things. I think, one, like I mentioned, the languages and framework we use is very simple for anyone to use. Anyone who's done any kind of web development would pretty much know how to build a plugin.

23:26So it's very accessible to a lot of developers. the values of Obsidian, just as a pure note-taking tool, are very aligned with what developers like. So we have just a lot of developers who use Obsidian as their note-taking app of choice because it's private and because it has this markdown format as the core way that you write text. Because it's so customizable, it attracts developers. And then developers are using it all day long. we have APIs that pretty much allow you to do anything with the app that are published and like there's a lot of documentation about that so it's kind of that combination of a lot of developers are using it it's easy to make the plugins we have we added the API very early on and so if you have that itch you can just like scratch it very quickly if obsidian is not working the way you want you can pretty much change it you know very fast however you might want it recently I interviewed Ivan Zhao, the CEO of Notion for Decoder.

24:29You mentioned Notion as another product in this space that sometimes people might choose to use over Obsidian. And it strikes me that while your products do some of the same things, they're designed very differently. Notion is about pixel perfect polish and these beautiful interface elements. Obsidian, by default, can look a little bit more like a terminal. You take notes and markdown, this markup language, it has more of this DIY, almost hacker ethos. Is that intentional? And do you think it affects the kinds of users you attract? Well, I think the most fundamental difference between Obsidian and Notion is that Notion is a cloud service.

25:07So it's an app that interfaces primarily with a software as a service type cloud service. So you have to either be in your browser or on an app and you connect to a source of truth that's in the cloud. Whereas with Obsidian, all your data is local. So if you're not online, if you're on the plane or something like that, you always have access to your data. And that difference essentially shapes a whole bunch of other things. For example, it would be really hard for Notion to add plugins because they can't really make it's so easy to run arbitrary code in their cloud-based platform, whereas for Obsidian, it's pretty easy.

25:54There's kind of this fundamental split that occurs because of the way the apps are architected. Same with things like theming and design and how much customizability there is as far as the user interface is concerned. I don't know if this will make sense to anyone who's listening, but the first thing that I ever did when I was like 11, 12 years old is when Winamp was coming out, Winamp 2. And I was all about making, you know, themes and things for Winamp back then, which was like a music player that you could customize. It really whipped the llama's ass. I have to say that. Yeah, absolutely. And, you know, I think there's a little bit of that flavor in Obsidian.

26:38Obsidian is quite popular with a lot of younger people. And I don't know what it is. Like at that time, you have the energy and the desire to just kind of have control over your digital space. And Obsidian makes that easy. And so in that sense, we're maybe a little bit less prescriptive about what the interface should look like. Even though I will say, I think in general, we're trying to make it a little bit more approachable so that we still retain that kind of infinite depth. It's like you're going to the beach. We want to make the shallow waters a little bit more accessible for people who are coming into it.