How the Head of Obsidian Went From Superfan to CEO  ## Metadata - Author: [[Decoder with Nilay Patel]] - Full Title: How the Head of Obsidian Went From Superfan to CEO - Category: #podcasts - URL: https://share.snipd.com/episode/9320d159-1f55-4d79-906a-064ba4ffd645 ## Document Notes ## Highlights - **Notes As A Linked Personal Wikipedia** - Obsidian treats notes as networked 'Wikipedia-like' nodes linked together to form a personal knowledge web. - This link-first model encourages connecting ideas over rigid folder hierarchies. Transcript: Casey Newton How does it work? And who is it for? Steph Ango 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. And 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. ([Time 0:04:47](https://share.snipd.com/snip/7825441f-92dd-47b0-8c5b-bb1de547981b)) - **From Patchwork Tools To Durable Markdown** - Steph used Obsidian to replace a glued-together set of tools and found its Markdown-based durability and polish life-changing. - He immediately adopted it because it solved his long-standing personal workflow problems. Transcript: Casey Newton You joined the company in 2023, you said, I can't overstate how life-changing Obsidian has been for me. It 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? Steph Ango 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. There'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, ([Time 0:06:03](https://share.snipd.com/snip/e672b773-f099-4ddd-b5bd-87e6f4eb26b7)) - **Markdown For Durable, Portable Notes** - Markdown stores notes as plain text with simple formatting, which maximizes longevity and portability. - Steph argues plain-text Markdown increases the chance your data survives long-term and remains accessible. Transcript: Steph Ango 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. But 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. ([Time 0:07:45](https://share.snipd.com/snip/b8e2cc5b-e45c-4fe6-9fed-afc73627fb80)) - **An Essay Born From Linked Notes** - Steph described writing an essay 'Pain is Information' that grew from linked notes and a Murakami quote during a tough period. - He credited Obsidian's freeform linking for allowing ideas to marinate into publishable essays. Transcript: Steph Ango 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. So 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. But 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 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 free-form way and connect different concepts that you might be thinking about. ([Time 0:10:15](https://share.snipd.com/snip/7f7028fc-751a-4cae-9126-e1dffca79f04)) - **Favor Links Over Folders** - Use Obsidian's freeform links instead of rigid folders to maximize serendipitous idea connections. - Keep many notes open and link liberally to discover unexpected combinations. Transcript: Steph Ango Yeah, 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. And 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. ([Time 0:13:13](https://share.snipd.com/snip/4a578798-1f44-4c5a-9759-e985db286c02)) - **From Superfan To CEO** - Steph joined Obsidian after building popular community plugins and advising the founders following his startup exit. - He started as a contractor and later became CEO, blending community, design, and product work. Transcript: Steph Ango 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? 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. And 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. Of how the community of Obsidian is so strong some of the things that I was making we're 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 like from me on their front page and we 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? I 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. ([Time 0:17:50](https://share.snipd.com/snip/87a5d53a-f358-4d8d-8dfe-20547fd96612)) - **Plugins Scale Features Without Bloat** - Plugins let Obsidian remain small while supporting niche, specialized features that only subsets of users need. - The plugin ecosystem drives innovation and signals which capabilities merit core integration. Transcript: Steph Ango 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, and then the app becomes bloated 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. So 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. ([Time 0:21:34](https://share.snipd.com/snip/e9355bd6-aee1-4943-afca-24b6514bb624)) - **Plugin Fix Led To Hiring** - The Advanced Tables plugin, written by Tony, solved a basic Markdown pain point and led to hiring him. - Obsidian frequently hires active plugin authors to bring valued features into the team. Transcript: Steph Ango Of the most popular ones are very simple. There are things like someone who's on the team now today, Tony Griesinger, 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. And 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, who's 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. ([Time 0:23:53](https://share.snipd.com/snip/b0ee7709-1525-49fe-b4cf-8551091acccb)) - **Local-First Design Shapes Everything** - Obsidian's local-first architecture (files stored on devices) fundamentally enables plugins, theming, and offline access. - That architecture attracts developers and power users who value control and customizability. Transcript: Steph Ango I think the most fundamental difference between Obsidian and Notion is that Notion is a cloud service. So it's an app that interfaces primarily with a software-as 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. Like, for example, it would be really hard for Notion to add plugins because they can't really make it so easy to run arbitrary code in their cloud-based platform, whereas for Obsidian, It's pretty easy. There'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 themes and things for Winamp back then, which was like a music player that you could customize. Casey Newton It really whipped the llama's ass. I have to say that. Yeah, absolutely. Steph Ango And, you know, I think there's a little bit of that flavor in Obsidian. Obsidian 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. ([Time 0:28:00](https://share.snipd.com/snip/a13d4634-0a33-440f-8ecf-acf212d9bab5)) - **Privacy Means Fewer Product Metrics** - Obsidian intentionally collects no analytics and doesn't track users to preserve privacy and trust. - This privacy-first stance means the company lacks traditional metrics like active-user churn data. Transcript: Steph Ango Actually don't know how many users Obsidian has. We don't know how sticky it is in a lot of ways because we don't have any analytics. It's very privacy-oriented, so we don't track anything about our users. We don't know what suddenly causes someone to churn or whatever. Those are things that we prefer not to track. We also, the data doesn't have to be exported. If someday Obsidian went out of business, you would still have the app on your computer. But even if you chose not to use it, you wouldn't even have to launch the app. You don't have to export anything out of it. And this is one of the big issues people had with other tools out there that have either gone out of business or been acquired by private equity firms and different things where they kind Of start tightening the screws and increasing the pricing over time and you just kind of feel like you're locked in and you can't do anything about it so with obsidian your data is there And i think that the feeling that that gives you of kind of freedom and security paradoxically is quite sticky because even though you have all your data you could just i mean i personally With my vault, my Obsidian files, I'm constantly editing my Obsidian files, not in Obsidian. Like I will use code editors and other tools to do like mass modifications to hundreds of files. You can run Python scripts on your data. Like you can kind of do anything because it's just files at the end of the day. ([Time 0:30:53](https://share.snipd.com/snip/97a2161b-3163-44b8-a85c-6f35828adf9c)) - **Disable Notifications To Preserve Focus** - Avoid apps that design for engagement metrics which nudge you back in with notifications. - Disable notifications and pursue restorative offline activities to keep note-taking healthy. Transcript: Steph Ango I think they can sometimes be designed with anti-patterns that are explicitly about that. Some companies have metrics that they track, like number of active users and how do they define active. And so now they're sending you notifications so that you're reminded to come back to the app so that you do whatever the thing is. That's part of the reason we're not interested in having any of this data, we don't really want to be tracking our users in this way or incentivized to create usage where none is needed. If your use of Obsidian is throughout the day, you have these like random ideas and you just want to pop in and drop a note like inside of your daily note or something like that, you should Be able to do that and not get, you know, sucked into this thing that's like trying to engage you. There are a lot of people who keep trying new apps and nothing sticks for them and or get caught up in the organization or beautification of their notes. And I think that can happen in any app. I mean, I hear about this from just in general, and I think I don't know what it the cause is. My sense is it has nothing to do with the apps unless they're like literally trying to engagement bait you in these weird ways. I think it's just sort of an affliction of like the digital age where these things are so malleable, it scratches an itch that we have in our brain to like optimize. And for certain people, if you're someone who loves solving puzzles or like doing Sudoku or something, it's just like it's kind of addictive in a way that might not be the most healthy. And I'm not exactly sure how to solve that. ([Time 0:34:35](https://share.snipd.com/snip/1b60fd22-6eb6-4d06-8b51-8b0adad7faa3)) - **Sustainable, Minimal Monetization** - Obsidian makes money via optional paid services like Sync, Publish, and donations while keeping core usage free. - A small team plus these revenue streams has kept the company profitable since early on. Transcript: Casey Newton Well, there's a few different revenue sources that Obsidian has. Steph Ango One is our sync product. You know, you probably want to use Obsidian on multiple devices. So if you have a phone or iPad, computer, because the files are local to your device, you need a way to keep those versions in sync. You can totally sync your files using Dropbox or iCloud or Google Drive. There are many different services out there, but we make one that is our Obsidian Sync service. We think it's the best one because it's totally integrated into the app and it has a few extra features like around version history and, you know, it's end-to encrypted. So by default, it's like much more secure than a lot of the other options that are out there. That is one of our major revenue drivers. Publish is our other service where you can take your notes in Obsidian, make a website out of it. And then we also have a couple, essentially donation programs, which are catalyst and our commercial license, where we have users who want access to the beta versions or want to support Us, you know, because they believe in what we're doing. And so they can essentially send us money. So those are the main ways that we make money. Then we have like merch, but it's actually all breakeven. So we don't really end up making any profit from that. But, you know, the thing is, because the team is small, it's, you know, we don't need mountains of cash to pay for that. And it's just us and some computers. So it's not like there's a big amount of expense. So it works. Is it profitable? Yes. ([Time 0:42:57](https://share.snipd.com/snip/43e72d1e-d3c0-4d4a-ac9f-61025dd633d9)) - **Community And Manifesto Drive Decisions** - Obsidian uses a manifesto and active community signals to prioritize work rather than top-down investor deadlines. - The flat team structure enables rapid prototyping and self-motivated projects. Transcript: Steph Ango Yeah. Well, so we have this manifesto that you can look at if you go to obsidian.md I think that is in a way the most powerful driver of what are we doing because it describes our values, which Are to make this app that's super private, super customizable, and durable around this kind of idea of these files that hopefully you'll be able to own for the rest of your life. I mean, the community is always driving us towards the next big thing that's a problem. So, for example, last year, one of the big things we started working on was Web Clipper. A lot of other apps have something like that. I think it was, you know, Evernote was probably the first one that did a really good job with this back in the day. Then, you know, there's services like Pocket that has shut down recently. And so a lot of people in the community were saying, hey, you know, this is like a major hole, a gap for Obsidian. All these other apps have great web clipping tools. And so we built one. I think that whether it's through plugins or through just general complaining that we're hearing from the community, we kind of know what the biggest gaps are. So we always have generally an idea of what we want to work on next but I think there's also a self-motivated aspect to it which is because our team we're using it all day we we also someone Will become an advocate or a champion for something so I'm for example I'm always using the iOS app and I'm always coming across edge cases where I feel like there's too much friction. And it, you know, there's other people on our team who use Android or who use Linux and like, or who use Obsidian in a slightly different way. And it kind of becomes your mission internally. This is not really that different than other companies, I don't think, but it kind of becomes your flag to raise with the rest of the team and kind of convince the rest of the team it's an Important problem that we have to work on now. But because the organization is so flat, we can make decisions very easily or it's very easy for one person to just go off and like prototype something for a few days and show it to the team And say like, hey, I like kind of solved this problem, like help me get this polished in a way that we can release it. So that makes it really, really fun. And because we don't have investors or any kind of like top-down pressure telling, like forcing any deadlines or anything like that, it's very self-motivated. ([Time 0:45:03](https://share.snipd.com/snip/78f8a7fa-c54a-41e1-8a65-3bc9b095e82e)) - **Bring AI In Only If It Respects Privacy** - Prioritize privacy when adding AI: do not route user data to third-party servers without consent. - Rely on the plugin ecosystem for experimental AI features rather than forcing built-in LLMs. Transcript: Steph Ango On AI and productivity tools? Will you add features like that? So far, there's no AI options that are built into Obsidian except in Web Clipper, which is intentional because it sort of lives outside of Obsidian itself. We have a feature called Interpreter that allows you to, at the time that you're capturing a web page, basically put in a bunch of prompts or questions. Like if you want to fill in metadata about that page and you want to say like, who is the author? Or let's say you're saving, I don't know, products because you're doing research on, you know, what podcasting microphone you need to buy next. You could grab all the metadata and specifications automatically just by putting in this prompt and it will kind of save all of that. But that's like living outside of Obsidian. And it's not about replacing your thinking. Fear that I have when it comes to AI is I don't want in my own use to replace my thinking, the insights that I'm going to gather with a summary generated by AI. Now, there are tons of people using AI with Obsidian. Like because of the plugin architecture, AI is by far the most popular category of like new and up and coming plugins right now. There's a lot of plugins that people are making using AI. A lot of the LLMs are very knowledgeable about Obsidian and its API. So you can just go into Cloud or whatever and just say, hey, make me an Obsidian plugin that does this or that. And that's a big challenge for us because we're like, there's like a mountain of plugins that is growing really quickly that we need to review. And it's like happening faster than we can keep up with because of AI making it so easy to make plugins. So AI is definitely being used. I think our philosophy as far as how it would ever make sense to be put into Obsidian is it has to fit with the principles that I described that are in our manifesto on our website, which Is it would have to be private. So whatever options we build in, we're not comfortable with the idea that our users' data could be stored in Open AI servers without their consent. You know, I think a lot of tools out there are just kind of defaulting to this feeling of, hey, there's this arms race, we got to put AI into everything, let's put a little magic button everywhere. I don't think that that's us. Like, we want to give users confidence that their thoughts are theirs, things are not going to be used in terms of training the next LLM. That being said, I do think AI can be really powerful for certain uses. The question is, in the long term, do we end up giving an API to the plugin community so that they can more easily build those types of functionalities. Right now, we're not working on it. We've just kind of been holding off and watching what's going on. ([Time 0:48:10](https://share.snipd.com/snip/def65824-256d-49a8-bd1b-d08536d48e2c)) - **Bases Turns Notes Into Databases** - 'Bases' is a beta feature turning note metadata into table, card, and Kanban-like views built from existing notes. - Steph reported bases exceeded expectations and will be iterated on based on user feedback. Transcript: Steph Ango Now, it's this feature called bases. The idea is that in Obsidian Notes, you can store properties, metadata about the current file. So for example, if I have a note about decoder, I might put the name of the host and like a list of episodes and for each episode that I'm listening to and want to take notes on, I might write Down which guests were on there, what date it came out, what was the episode number. And what BASIS allows you to do is kind of visualize your notes of a certain kind as a table or as little cards, eventually things like a Kanban view or other types of views. So it's like a visualization layer on top of the data that you already have. And we just make it really easy to create that database from the bottom up. So it's kind of like a backwards database because all the data is already in there. You're just like looking at it by saying, show me all notes that have the tag books, for example, or a link to Casey. And then I get a table and then I have all my metadata and I can edit it. So it's quite powerful if you're someone who enjoys tracking the books that you read or the movies that you watch, the places that you go, articles you've read. You can very easily create these structures or do project management. So we're really having a lot of fun with that. It's been way more popular than we expected. It's currently in beta. ([Time 0:53:45](https://share.snipd.com/snip/ce864fa8-67cf-477b-a55f-bb2ccc9c83d9))