8: Steph Ango - Tools for Amplifying Our Light

[00:00] Welcome to Dialectic Episode 8 with Steph Ongo, aka Kapano, as he's known on social platforms. [00:07] He's a designer, writer, entrepreneur, toolmaker, [00:11] and CEO of Obsidian. [00:13] Obsidian is one of my favorite products I use every day. [00:17] It's a robust note-taking and thinking tool that uses bi-directional linking and an extensive plug-in system. [00:24] to become one of the most powerful and extensible tools around. Steph's background is in biology and industrial design, [00:31] But he's one of the most dynamic and multifaceted creatives and designers I've ever met. [00:36] He's worked across software and hardware to supply chain and packaging with a former company called Lumi.

[00:42] He's an amazing writer. He's worked with wood and furniture. [00:46] He innovated in printing styles with a former company called IncoDye. [00:50] He's created his own custom color schemes and design systems and other forms of web and open source systems. He's made podcasts and videos. He truly is a polymath. And this is one of my favorite conversations I've had so far. [01:04] More than anything, he sees himself as a toolmaker. And I think you'll see that in our conversation and the way he sees the world and designs for removing friction, making creativity more possible.

[01:16] We discuss many of his ideas and talk through several of his short essays, [01:20] which really pushed my thinking. [01:22] We talk specifically about design and software. [01:26] learning and agency, how to use constraints in style. Steph is truly wise. He is so energizing to spend time with, and he is prolific creatively. [01:38] He's an amazing Twitter follow as well, and I would strongly suggest reading his writing after you've enjoyed the conversation. I believe this conversation pushed me and will hopefully challenge you to be more creative, agentic, and optimistic.

[01:51] Here's Steph. [01:53] Ready to rock. [01:54] Let's go. I'm really glad to be here with you. [01:57] I want to start on a theme across your work and writing that seems to be one of the main reasons [02:04] I experience you as being very opinionated and [02:07] Good way. Hmm. [02:09] And the theme that seems to run across and maybe enable that is... [02:13] you really are thoughtful about constraint. [02:17] whether that be professionally, creatively, in writing and design, [02:21] I think this applies to stuff like Obsidian's company structure and some of the ideology and principles behind it.

[02:27] your writing and your brevity, but also, frankly, just across your design thinking. [02:31] I'm curious why... [02:34] constraint is empowering to you. [02:37] Yeah, that's interesting. I don't know when I... [02:41] started imposing constraints on myself. I feel like constraints just naturally occur from [02:48] you know, the... [02:49] Like if you're writing a tweet, there's so many... There used to be at least so many characters that you could write. [02:57] Or... [02:57] If you go to my projects page on my website, some of my oldest projects are Winamp skins from like early 2000s or something like that.

[03:08] And we're talking Winamp 2, which is before they let you do whatever you want with shapes. So [03:14] You had to, like, work within a certain number of pixels just to... [03:19] even do a volume slider. You had... [03:22] so little that you could do [03:24] But yet that's where all the creativity came from. [03:28] I would look at some people who I thought were amazing Winnempskin artists back then, and I was like, how did they figure out how to, like... [03:35] put this entire little animation in like [03:38] you know, [03:39] movement of 12 pixels and that would fascinate me and I you know I would just like think about that and try to come up with something myself so [03:48] I think maybe that's where it started, like just out of necessity, those constraints, you know, shaped the way that I design things or think about things.

[03:57] But then over time, [03:59] I had... [04:00] eras where I had less constraint, like, you know, my previous startup before Obsidian, [04:06] We went down the VC path. We had a lot more money than any other project that I had ever done before. And in a way, [04:14] I missed having those constraints or the lack of constraint. [04:19] in certain cases [04:22] let us down decisions that [04:26] were not as good as if we would have those constraints. And so now I'm always looking for how I can add forceful constraints into [04:34] my own process and [04:37] pick good constraints that I think I can live with and I can have fun with and that becomes a canvas to experiment within.

[04:45] Yeah, it seems like... [04:47] Obviously, you've done a lot of work in the physical world, too, but in the digital space... [04:52] It's funny you bring up the earlier 1A example where digital space, [04:55] video games, software, all over the place. Tons of constraint. And basically the [05:00] last 20 years has been a [05:02] Removal [05:03] continuous removal of constraint or at least a continuous expansion of what you can do [05:08] So I find it particularly interesting that some of your clearest forms of constraints [05:12] are almost like purely fake or imaginary not fake imaginary or self-imposed yeah [05:19] Short writing is a simple example.

[05:22] Most people, I think, outside of Twitter, the only reason to do writing outside of Twitter would be long form, and yet you're doing shorter form. [05:31] Is that something that [05:33] Requires discipline? [05:34] Or is it actually just like, oh, I know the freedom or the... [05:39] I don't know, the way it's empowering on the other side, that it allows me to show up more consistently. [05:45] Yeah, well, it's definitely self-imposed, like, but then it's the element... [05:51] of a style. Basically, I think you want things [05:55] in general to be [05:58] recognizably you and to become [06:01] easier and easier for you to do [06:03] like, [06:04] It can become...

[06:06] Writing is difficult if you have no constraints like if you know that okay, I'm gonna try to fit in this idea in 500 words then I [06:13] you know the kinds of things that you're probably not going to write about. [06:18] A lot of my essays have no... [06:21] reference material like there's just like no footnotes there's no nothing it's just like I'm I'm stating things [06:27] Like, [06:28] This is my opinion, and... [06:30] you know, I... [06:33] Well, when my essays in particular, I'm like writing to a younger version of myself is who I have in mind.

And I'm like, let's imagine that the only thing I can pass on to like this younger version of myself is like X number of words. Like, here's the most concise way I can like communicate this across time to this like younger version of myself. [06:53] So the... [06:54] The conciseness comes from the fact that I know that I wouldn't want to read something long ago. [06:59] Back then, especially. Probably most of us still. Yeah. One of the cooler things when I was reading a bunch of your... [07:06] rereading about your stuff, I was like loading it into a read it later app.

Hmm. [07:10] And there's something with the rendering or however it worked where... [07:14] Occasionally, I would get... [07:16] presumably what was an older version of one of your older pieces. Oh, okay. Yeah. And I could see the culling. Like I could see little... I removed some words. Yeah. It was really cool. I am not... So see, this is one thing that is kind of weird about my blog is I just will edit old pieces all the time and not... I don't know. I could put like a last edited or versions or something like that, but I just...

[07:39] don't care about the continuity of it. I am trying to make each one really good. And oftentimes what happens is I'll write a new essay, [07:49] And I try to link very profusely to other essays because they all kind of build up on each other. [07:54] And when I link, I'm like, oh, I wrote about this, and I'm making a link. And then I go to that essay, and it's like 10 years old now, and I'm like, damn, this is... [08:01] I could have done this way better. [08:02] And I'll just most of the time it's just too wordy and I can I can simplify an idea or there's like this connective tissue that has no.

[08:10] A lot of the words I remove are just connective words that [08:14] They're just... [08:14] unnecessary they don't actually have any like calories in there and so like i i'm trying to get rid of that [08:22] And then, you know, recently... [08:24] At some point when... [08:26] Twitter, stop letting you link to things. I started putting screenshots of all my essays, and I wanted the screenshots to have a certain feel to them so that people, when they saw it, would think, oh, hey, that's... [08:38] from Kapano, and [08:40] they would just instantly notice that it's like it feels...

[08:43] like one of my essays. [08:45] So I came up with this color scheme, and the color scheme has... [08:50] basically nine colors. And now I've been using that color scheme for all kinds of stuff. Lately I've been like teaching myself piano and I've been using these colors to [08:59] make these little tools for myself to help me [09:02] kind of bridge synesthesia with, uh, [09:06] the way my brain works like i'm trying to like connect colors to notes so that i can learn them more easily amazing um [09:13] But I have this set of colors, so now it's like, okay, I'm just going to use those colors, and then by default, it's going to fit into everything else that I did, and so...

[09:22] it just becomes a sort of signature thing [09:25] It's a little scary. I remember always wanting to do something like this, but I was afraid that [09:33] that I'd have to stick with something that I would eventually... [09:36] Something like this being the brevity or the color scheme? Yeah, like the color scheme that that or even like the design of my website or something like that, that it would... [09:46] The continuity was so important to me. I felt like I had to get it right because otherwise then I'm stuck with something that I don't like.

[09:52] So the same reason that I would – it's really hard for myself to imagine myself getting a tattoo because I'm like – [09:59] I would have to like feel really great about it. And then I've, you know, known people who have lots of tattoos and they're like, Oh yeah, this one sucks. But [10:05] It reminds me of a different time or whatever. And I like that notion too. [10:09] Yeah, that ironic. Yeah, it's an easier... [10:12] it's easier to relate to your digital self in that way. There's less permanence.

The, the, [10:18] I think the other thing that's so powerful about having consistent visual language online is [10:25] but also brevity, all these things that you discussed is in a world where increasingly... [10:30] Think about old Twitter. Somebody followed you. They were pretty likely to reliably get your content because they opted into it once. Yeah. That's not really how, certainly not how TikTok works. Increasingly, it's not how Twitter works. And yet. [10:41] You're almost hacking the, like, you're giving people, before we turned the mics on, we were talking about, like, [10:47] using not your face as an avatar.

And there's a similar thing there, which is it's a little mental visual cue for somebody to kind of, oh, I've seen this before. Oh, I like that guy. Oh, that guy with a little beige face. He had interesting ideas. Oh, I read a short, [11:01] screenshot essay from him. And that compounds in a way that I think is actually [11:07] the way to build [11:08] a following or a brand on the modern internet where every incremental piece of content needs to almost earn its place [11:15] Yeah, it's like when someone that I've been following for a long time changes their avatar, it's like they have to start...

[11:22] Who are you? Your friend had super long hair and they got a crazy haircut. Yeah. We have to start all over from scratch now. Yeah. I totally agree with that. Yeah. I mean, you've done the same with your color scheme. I know when I see that little pink circle, I know that's you. But to the tattoo point or whatever, it's like, now, if I ever want to change it, am I undoing everything? Yeah. [11:43] B. [11:44] This is the other thing I respect about you a lot is you're someone who is so thoughtful about this stuff, but also...

[11:49] doesn't default to weight, at least from my vantage point, you're so generative, you're so prolific in how much you create. [11:56] And yeah, I'm curious how you balance that. [11:58] very concrete style, very constrained, but also is just like [12:02] I don't know, you put out something today or yesterday about your piano thing. It's just constantly happening. [12:09] Okay, so... [12:10] Yeah, the thing is, if you look at the... [12:15] at my website and you look at the, um, [12:18] timestamps on the essays. [12:21] they're [12:22] There's like one a year.

[12:24] Like... [12:25] I started my first blog in 2005. So there's a lot of stuff. The oldest one on there now, I think, is 2012. Yeah. I found the oldest one under like the linked favorites. [12:34] Yeah. [12:35] Yeah, that's pretty old, I guess. But I have some older stuff that I just... [12:40] you know, I'm calling things over time. There might be some good stuff that has been removed that might deserve to be back on there, but... [12:49] Yeah, so there was a long period of time where I basically wrote a blog all by myself, like to myself.

[12:56] for like 10 years. [12:57] So or just no one knew about it. No, just I. [13:01] What I did was I made a blog and I had it in like private mode because I wanted to like [13:09] uh kind of set up the visual language and start writing and i wanted to have like a few good posts before i launched it and then i just never launched it so i just wrote and then i kept writing and then that became like my note-taking app in a certain way wow um [13:23] this private blog that I was like writing to no one.

[13:27] But then... [13:28] At some point, like a few years ago, I thought, okay, I really should start publishing stuff. [13:35] I just had this archive of like 10 years of drafts. And like, then I was just like looking at all my drafts and some of them were really good. And I still felt good about them. [13:44] So... [13:46] I think a lot of the process is just like planting seeds and, and, [13:51] waiting for those things to just sort of like reach a certain maturity where I can look back at them.

[13:57] a year later, five years later, and I'm like, I still agree with myself. Therefore, I should post this. And by that point, I have like a clear idea of what the thing is. [14:08] So I do use social networks like Twitter to [14:11] to kind of just like put the messiest stuff up and see if people disagree. [14:16] Um... [14:18] and then I get some good kind of friction from that, which [14:22] I used to [14:23] kind of catalog [14:25] you know, [14:28] arguments against what I'm saying or try to refine my language.

And that just goes into drafts. And then sometime later... [14:37] Something happens and I'm like, it's time. Like that idea just came back and I have like all the context necessary to just like spit it out in a very short burst. Right. Right. And so. [14:48] I... I... [14:50] it's really hard to like, [14:52] It's one thing that's nice about getting older. It's really hard to do that. It's very frustrating when you're younger. [14:59] I had the similar thing with [15:00] I created the series... [15:04] off a blog post called, the blog post is called Buy Wisely.

[15:09] And it was just... [15:10] Basically making the argument that you should buy more reliable, durable things that will last you for a long time and that the extra cost of it will end up being worthwhile. [15:20] And so I made a few recommendations of products that fit that description to me. [15:26] And when I was doing that, I did a bunch of [15:28] kind of self research on things that I've owned for a long time, how many times I've used them, how much did they cost me at the time.

[15:36] and try to understand the cost per use. So I did this whole spreadsheet and looked into all of these objects that are still with me. [15:44] And there's some new things that I've owned for one or two years where I feel really good about. [15:49] you know, how they will last. But I feel like it's too early to say so like I have to have like my rule for anything that I'll share is like I'm still using it five years later. [15:58] Share as in recommend? Yeah. Got it. Yeah, exactly.

And so... [16:03] it takes five years for one like new post to be added to that. And so it's like, it's, it's kind of frustrating in some ways. It's a filtration system. Yeah. Because I'm like, [16:13] I have some things that I... [16:15] you know, have incorporated into my life in the last couple of years, but they're not allowed in my constraint system because... [16:22] I haven't had them for five years yet. But it's a really cool blend of... [16:28] a baseline generativeness or generativity around creating things about [16:34] liking things trying things [16:36] that has maybe its insulation, whatever it is that you need to both [16:41] Keep enough distance from it that you can evaluate it.

[16:44] Maybe not objectively, but... [16:46] a little more objectively. [16:48] but also have the freedom to create. [16:50] I think like even going back a little bit, like the idea of having a private blog or something like that, like I think people get caught on one end of that spectrum a lot. They either are like, [17:01] sharing constantly sharing everything there's no filter there's not a lot of signal or they're hesitant to share anything [17:08] And it seems... [17:08] maybe somewhat [17:10] deliberately and someone [17:11] accidentally you've created an interesting kind of

[17:15] amorphous filtration system that allows for all the good on both ends. The creating, like, I don't know, the, like Rick Rubin, create something for yourself and then share it with the world. That's like, [17:24] It's like okay advice, but it's hard advice to take, and it feels like in some ways you're [17:28] You're manifesting some of that in a cool way. And then by the way, [17:32] I have experienced this where you go back and read something you didn't think was very good. And you're like, wow, I actually see I see the part.

[17:38] The wisdom there, like that is it's one of the other ideas I love of yours that I think about a lot is that is the like audience of selves stadium of past and future use. Yeah. And it's your this is sort of like you creatively negotiating with all of those and working together to kind of like figure out how to get to the best stuff over time. [17:59] Gosh, yeah, that idea is basically if you think of yourself... [18:05] as you know, [18:06] let's say you live 80 years. I forget what I put in the essay.

You had it in days. Yeah, but if you live 80 years and each... [18:15] New Day is one person, it would fill up a stadium. You know, it would be... [18:19] however many 50,000, 60,000 days in [18:22] in that stadium represents 60,000 people. And so you're [18:26] your [18:28] Current self, today's self, is on stage. You're in the middle of the stadium and all of your past and future selves are sitting [18:37] in the audience so there's like baby you like you're just like a one day old version of you all the way to like [18:42] 80, 90-year-old you.

[18:44] And they're all sitting. And I don't know, in my... [18:46] stadium I don't know how they're seated I think they're at random but I've talked about this with other people and they're like oh yeah in my in my mind stadium [18:54] They're all sitting in like chronological order. So there's like a baby section. [18:59] There's an old me section. Um... [19:02] I like that. You can imagine looking to the part of the stadium. I'm appealing to my five-year-old self. [19:08] Yeah. In this moment, all 360 of them. Yeah, and I think that's, yeah, basically...

[19:15] anything I've ever really tried to create was for a version of myself. And that makes it a lot easier in a way because... [19:25] The more I've... [19:27] gone in that direction, the more I find that people actually respond to it, like other people respond to it, that like I'm [19:35] The point that you're referencing about this piano thing, I have a real problem trying to learn musical notation. It's like it doesn't make sense to the way my brain works. I want to get good at sight reading. [19:46] And for some reason, the musical notation is something that really is problematic to me.

So I'm trying to figure out. [19:54] solutions [19:56] to help. [19:57] me with that and I've been posting some ideas and then other people are like oh yeah that's cool like you know that [20:02] That would help me [20:03] people [20:05] are also in the same situation that I am, or they're teachers and they're trying to teach students how to sight read and they're like, oh, I could use this with my students. [20:14] and [20:15] Thank you. [20:16] I don't know. I mean, this is like not this is just a trope at this point, but it's like, yeah, make something that you would enjoy.

And then other people, you know yourself well and. [20:28] You're unique, but then a lot of people have the same problem that you have. So if you understand the problem well, then... [20:34] Other people will probably enjoy whatever solution you come up with. [20:37] Yeah, the making of something for yourself, [20:40] I think is an obviously empowering constraint. Maybe what's so... [20:45] powerful about the way you talk about it is [20:49] by orienting it around past selves or future selves. [20:54] There's like a separation that allows you to. Sometimes it's like, oh, make something right.

What do you mean? What is. Yes. [21:00] I almost have back to the idea of being able to go back to something you wrote in the past and reduce it and make it even more clear. It's almost like the older, wiser version of yourself going to that young self who is... [21:13] energetic and had the idea and wanted had so much to say about it but didn't quite have the words and you can almost imagine that person like the older you like putting your hand on the shoulder and saying like oh here love me [21:22] Let me help you word this.

Right. It's a really beautiful metaphor that I think is... [21:27] still anchored around that constraint of the audience of one, this pretty common idea. Yeah. But it's a cool tweak on it that I think is cool. It's helpful. And also the thing is that, you know, people... [21:39] People ask this question, like, what piece of advice would you give to your younger self or something like that? And it sounds so grandiose. But, like, some of my things are just, like, this is the kind of shaver you should buy. Or this is, like, so basic.

I went through a bunch of pain to learn this for you. Yeah. And it's not. [21:57] It's not that grandiose. It's like, this is... [22:02] how you should meal prep or something like that if you want to like not be hungry at, you know, 1 m. on a workday. Like these are not like really... [22:12] Like, you know... [22:13] big problems of society. They're just kind of things that [22:18] helped me [22:19] becoming an adult. [22:21] learning how to [22:24] be me I don't know but often the writing from other people that we all find so useful ends up being kind of shaped like that yeah it's just really [22:32] really basic stuff sometimes.

[22:34] On the topic of removal, [22:38] You wrote a piece I liked a lot about when you talked about the invisible. Removal is often invisible. It's like people cleaning up a beach. Right. Right. [22:46] And it made me think of the Steve Jobs idea about focus isn't about... [22:51] just choosing what to work on. It's about saying no to a thousand good ideas. So you can work on the things that are really, really important. Yeah. Yeah. [22:58] And I'm... [22:58] Whether it be, again, going back to an old piece and you're figuring out how to shorten it by 25 words to make it more clear...

[23:06] or in design and product and building the business. [23:09] How do you say no? I struggle with this in writing as an example, maybe in editing podcasts and all the other things I do and how I spend my time. How do you say no? [23:19] to the good stuff. [23:20] So you can... [23:22] Spend your time on the really good stuff, especially as someone who's so prolific. [23:26] Thank you. [23:26] Thank you. [23:27] Um... [23:28] Yeah, so the idea of what can we remove is... [23:33] Thank you. [23:34] It's just a question.

[23:36] that hopefully is useful [23:38] for a group or for yourself when you're working on something. It's just... [23:45] remind yourself to ask that question. [23:47] What can I remove? What can we remove? What's like not contributing to the thing and oftentimes [23:53] you know when you're writing an essay or you're building a [23:56] an app or you're working on something [23:59] some of the prior [24:00] like first draft stuff. [24:02] ends up sticking and staying [24:05] into the to the final thing. And so [24:08] That's one of the things that I like about giving myself like [24:11] a long pause before I publish.

[24:14] is that then I can see, oh, yeah, that was just like, [24:17] this weird old cruft that was there from like an early version and like a [24:21] you get kind of [24:23] stuck. [24:24] keeping it around because you're just in a flow and you have like a memory of your [24:32] past self from an hour ago when you started writing this essay, like it still makes sense. You needed it to get there almost. Yeah, you needed it to get there. [24:40] And so you have this... [24:43] Yeah, I mean, it's like, again, classic wisdom from writers.

I forget what it's like. [24:49] uh... [24:50] kill your darlings or something like that. It's like, you know, it's a classic thing, but having that gap where you come back to something with fresh eyes and you're like, oh... [25:00] That's so obviously like [25:02] unnecessary now. I was holding on to this an hour ago or a year ago or whatever. Yeah, and so there's a... Part of it is one tool that you have is the ability to just like... [25:13] come back to it the next day or... [25:16] you know, a year from now?

Is it actually urgent? You know, maybe you're working on a [25:20] you're you're doing some work and you can't that's not how they work you have a job to do you have to ship something tomorrow [25:26] Um... [25:27] So. [25:28] We have this all the time with Obsidian. You know, we're working on... [25:34] a [25:36] new release of Obsidian every... [25:38] you know, every few months we have like a big new release. And so, [25:42] There's always a point, every single release has it, where it's like, do we want to add this other feature or bug fixer thing, or do we want to ship what we have?

[25:52] and [25:54] An earlier version of myself, like in my younger days, would always choose, like, let's make it as good as possible and then ship it. [26:01] But now I'm always just like, let's ship something and cut. [26:07] Everything that we can cut [26:09] so that it's good enough to ship on this particular day. [26:13] And once you... [26:15] change your mindset to like, I know that I want to put it out there tomorrow or in a week or a month. [26:22] it just forces you to trim anything that's not necessary.

So that's another tool that you can... [26:28] You just... [26:29] it's another form of constraint like one constraint is a time-based constraint just wait a year and see how you feel about it another constraint is just tell yourself i gotta put it out tomorrow yeah so therefore i gotta cut everything yeah but that that that that like zigzagging between those two ends of the spectrum is actually you know a very common thing that i do it's it's [26:48] It's like attacking in [26:51] Tacking is like how you move against the wind in a boat.

Oh, huh. If you're trying to go straight against the wind in a boat, [26:58] you have to basically zigzag your way. So you go all the way, you know, 45 degrees left and then you go 45 degrees right. [27:04] And you're making like forward progress, but you're doing it in his exact fashion and you're like bouncing back and forth between. [27:10] left brain, right brain, [27:12] Long-term, short-term? [27:14] you know, you know, maximalist, minimalist. Most of us are stuck in the middle. Yeah. Hold on both sides all the time. [27:20] Yeah.

[27:22] Only there's this quote, I'm like, this comes up all the time with my partner, this quote from S. Eliot, which is, [27:28] only those who are willing to go [27:31] too far can possibly find out how far one can go. [27:34] And so it's just like, let's [27:36] remove everything let's add everything let's like like let's just see what happens like for science and and and then you're like actually half of this stuff was not necessary and [27:47] So, and... [27:49] it kind of depersonalizes the [27:52] your attachment to whatever you're doing.

[27:56] And I think that was like fundamentally the point about that, that what can we remove essay was like, [28:01] we get attached to the things that we can see, [28:04] But like when you come to a, to a, [28:07] beach that's totally, you know, [28:09] pristine you don't know who was there before like picking up all the trash right and if you're walking around that beach and you see a piece of trash you should pick it up so that the next person has the ability to like [28:21] Enjoy a pristine [28:22] beach, but they will never know that you were like, they will not [28:27] they will just enjoy the pristine beach.

Yeah. It's not even that they're not thinking about who cleaned it up. They're probably not even thinking about the fact that they had trapped. The reason, and maybe there are other metaphors that are better examples, sometimes interior design or whatever. It's like, it's actually what's not there that makes the space so great. And so it's the subversion or this, [28:45] Yeah, wow. That's powerful. [28:48] The last constraint-related idea that I wanted to ask about is [28:52] you've written extensively about, which would be [28:54] highly principled, if not ideological approach to making software and building a company with Obsidian.

[29:02] This, I think probably the most famous instance of this that you continue to write about in different forms is file over app. This idea that we should have. [29:09] Plain text. [29:10] usable data and files independent of the tool, [29:16] I'm curious just... [29:17] very practically, maybe we talked about some of this, but like how does having a [29:22] philosophically driven approach [29:24] affect the day-to-day of building and also how does it affect you over the long term? [29:30] Even maybe something as simple as like, [29:32] how often we can ship an update and what goes into an update.

[29:36] Is it easier to remove stuff because of the principles? Is it harder to remove stuff? Is it harder to add stuff? [29:44] Okay, so there's like really two totally separate topics here. One topic is file over app, which is like really... [29:51] a political statement and it's like it's like I think that [29:57] This is societally important, like civilizationally important. It's like a rejection of like how big tech and a lot of companies are [30:07] built in the software ecosystem these days. [30:12] or have been for a long time.

So that's kind of like a more [30:16] it does then become a constraint within what we do at obsidian and like we we try to you know respect that constraint but [30:24] We wrote a manifesto that is very short, very simple, that has... [30:30] five things that we're focusing on. [30:33] and [30:34] Those are the constraints that we use, and they're pretty simple things. One is we want to stay independent. We want to be 100% independent. [30:41] user supported so all of our funding comes directly from our users we don't have investors [30:46] And we don't want to grow the size of the team.

So like that kind of is just like, [30:51] a value that has to do with independence and [30:55] Part of the reasons [30:56] that particular set of values, that's one of them. There's privacy [31:03] There's durability of [31:06] the files [31:07] You can go to like md slash about and you can read the whole thing. [31:11] But... [31:13] a lot of those came from [31:15] the founders of Obsidian, Shida and Erica, who for some reason were like naturally just like genius about like the values and other things came from my personal experiences, having gone through.

[31:28] the process of building companies every possible way you can. [31:32] I did a Kickstarter campaign. My co-founder went on Shark Tank at one point. We raised money through VCU. I've done all the different ways that you can raise money and build companies. [31:42] companies [31:43] And I just like the kind of like Ocean's Eleven model the best. It's just like it's the most fun to have like a very small team. [31:53] where you just, I love making stuff myself. I don't really enjoy being a manager. I've done it in the past a lot, but I just want to be...

[32:03] designing and coding and writing and interacting with me. [32:06] the users directly. And that's just what I like. Other people might really enjoy working in a big company or being a manager or other things. It's not like a prescription for everyone. It's just [32:16] the way that we enjoy [32:18] building obsidian and yeah it has a lot of limitations we [32:22] In the previous company that I ran, Limi, [32:26] whenever we had a problem, it was like, who can we hire who is like an expert on this problem? Right.

[32:31] And we'll go find the best person, hire them, and then like empower them to solve this problem. [32:36] Now if we have this problem, like hiring is off the table. We basically don't hire. We have seven people full time. [32:42] we've kind of given ourselves a buffer like in our [32:45] you know, kind of internal [32:47] It's not listed specifically in the manifesto, but it's like an internal limit of like 10 to 12 people that we don't want to. [32:54] Grow Pass. Currently, we're [32:56] seven and a half or something like that because we have some people working part-time.

[33:02] But yeah, like we just, if the problem comes up, [33:05] And... [33:06] We have to either figure out how to solve it ourselves, [33:08] Or we just decide it's not a problem we want to solve at all. [33:12] So that, you know, [33:14] happens all the time. [33:15] We can't [33:17] parallel process on 20 different things at the same time we can only do like one or two things at the same like at once [33:23] companies [33:25] are these amazing kind of like symbiotic, like super intelligent like organisms that are capable of doing really complicated things, you know.

[33:35] Amazon has like a million people working there, you know, so they can do like so many things at the same time. [33:41] I don't want to... [33:42] run Amazon. I just want to have fun building stuff. And so... [33:48] I think having an understanding [33:51] and shunning [33:52] this sort of like [33:54] Having an understanding of yourself and being... [33:59] you know, [34:00] Thank you. [34:01] Thank you. [34:02] Mm. [34:03] Brave enough to, like, brave sounds... [34:07] to just reject like this like [34:11] sales pitch that is often given.

Maybe even a default in certain worlds or contexts. That you have to raise money or you have to do things this or that way. You should just do what feels right to you. [34:22] And it's still possible to be very ambitious within that. [34:25] framework like [34:26] Obsidian probably, I don't, we actually know how many users we have, but we probably have like three or four million users and we're seven people and like that's pretty crazy. It's definitely possible to. [34:36] to do something like that. [34:38] Within within that. [34:40] especially on the ambition note.

[34:43] Even the set of constraints and ideals you just talked about, some of them are more political. Some of them are about how you and the co-founders want [34:50] to live your lives and run the company, [34:52] Some of them are enabling from a [34:55] Truly like a principled standpoint. Right. [34:58] As an example, [34:59] I think the file over app piece, and particularly digital archival, the idea that [35:04] our data is actually usable in not only 10 years, but 50 years, 100 years. [35:08] That is something that is almost mission driven, right?

Right. [35:11] How does that balance? And maybe this is a false... [35:17] Maybe this isn't actually in contradiction or isn't mutually exclusive. [35:21] But you can imagine a world where the mission is weakened or getting to the mission is [35:27] on the timeline or at the scale you hope to, [35:29] is weakened by the fact that you guys don't want to manage people. Is this an overly simple example? Could be, yeah. And there's a world where... [35:36] 20 years from now or 50 years from now, the world is different. Maybe I'm assigning too much credit or ambition or whatever, but like these are...

[35:44] Maybe some of them are more just theoretical, but some of them could actually be very practical. [35:49] things where you're [35:50] core principled constraints end up running up against each other. And maybe, yeah, you don't need to raise... [35:56] $100 million in venture capital. [35:58] But, [35:59] having 20 people could help obsidian get [36:02] much more materially or much more quickly to its mission [36:06] Yeah, so you're saying file over app is this big idea that could have more [36:11] influence in the world if there are more people [36:13] working on it.

I don't know that. No, no, I think that's definitely a... [36:19] Fair point, it's probably true to some extent. [36:23] I think that... [36:27] I don't know. I would argue that even as seven people... [36:30] building this thing that is kind of like an example of what we mean by file over app has had more impact than if we had had like a million people working on it. Yep. [36:40] because [36:42] What we've seen over the last couple years is the biggest companies like Microsoft just put out like, [36:48] basically a new tool that converts all these old files, [36:52] Word and PDF and every kind of file format that is not that is proprietary and not open [36:59] to, you know, open format Markdown.

They're doing it, I think, mainly because it's the best way to ingest, like, a whole bunch of data into, like, AI. Yeah. Pretty surreal, though, for you guys. Yeah, it was cool. It was cool. And I can think of about, like, 10 different startups that have started based on file over app. And they're like, we're doing file over app for accounting. We're doing file over app for this or that. [37:23] And... [37:24] It's almost like a... [37:25] you know, requests for startups that YZ does. It's just like, file, like... [37:30] Sometimes I'll, yeah, I'll [37:32] post on social media, it's like, [37:34] we need a file over app of

[37:36] this category and then people are like oh i should go build that you know there's people doing cad file over up people are doing you know video they're they're taking that and expanding in other directions and if we thought a file over app as like a proprietary idea that only you know we should be the ones focusing on it would be less powerful it's better for everyone to have [37:57] if the idea is powerful enough and it's, [38:02] you know, and enough people agree with it, they can just go take that and run with it and build in their area.

And now it becomes like there's a shared ownership of that idea. [38:12] And I think that's in a way more powerful than trying to do it all ourselves. [38:17] But it requires us to be... [38:19] to like give it away and be alive. [38:22] communicative about like, hey, everyone can do this. [38:25] Maybe even more simple than that or more foundational might just be [38:31] the most important part of anyone's work is like staying in the game. And on some level, [38:36] Yeah, that's true. You are doing it in a way that allows you to do it.

For a long time, yeah. Not to mention, if you were managing a bunch of people, maybe you wouldn't have had time to write file over app. I didn't. Back when I was doing Lumi, I didn't have time to write because I was managing people. And like... [38:51] It's funny. [38:52] It's like, I'm... [38:53] still probably one of the like top [38:56] Obsidian users like I use Obsidian all the time and I love using it and so like [39:01] I am, if I'm not working on it, I'm using it probably like [39:06] actively at least an hour a day, but I have it open constantly in the background.

So I'm like bouncing back and forth. And sometimes I'll just literally spend five, six hours, eight hours in a single day just writing in there. I write my essays in there. I publish from there. [39:20] I work on like my side projects like this piano thing we were talking about a lot of my planning or [39:25] Sometimes I'll be building plugins like [39:28] I think if someone who is like a user of Obsidian were looking at the way that I spend my time in a day, they would be like, [39:36] You could be spending more of your time like [39:38] building Obsidian instead of using Obsidian.

Some people are like, where's this bug fix that I've, you know, requested, like, [39:45] two years ago or where's this feature? [39:48] you're spending too much time using obsidian and not building obsidian. [39:52] That's kind of what people are saying in a certain way, not in those words necessarily. But I don't think I would be building Obsidian if I wasn't using it. To me, like, actually... [40:02] The company is secondary to my personal goals of actually using the tool that I want. The reason I'm making it is so that I can use it, not the other way around.

[40:12] If I wasn't using it, then Obsidian the tool wouldn't be as good as it is. [40:17] So it's like, yeah, that's a powerful paradox in a way. And that's something that I didn't enjoy as much working on my previous startup, which was like, we were a B2B, you know, supply chain tool. And by the thing that we were making, we were not using ourselves. [40:32] And because we couldn't, we were busy building the software that [40:36] you know, was like a manufacturing and logistics platform. [40:39] I think that... [40:41] Going back to the earlier topic of like building something for yourself.

[40:46] If you really care about that, you have to make sure that it remains true, even as the thing grows. It's really hard. It's really hard to keep working on it. [40:55] Like, just think about any startup, like, that... [40:58] you use their product, like how many of them like are actually using the thing that they make all the time? Well, they probably started out using it or they had that problem. I mean, presumably you guys had that problem with me and that's what, yeah. Yeah. It's a, [41:10] It's almost a craft in and of itself.

[41:13] to [41:14] set things up in a way and maintain them in a way that allows... [41:19] for you to keep playing the game you want to play. Well, and you have to have... [41:23] The stamina... [41:24] Again, everything I'm saying is not a prescription. It's just this is what I enjoy doing. [41:29] If you enjoy, like, if your whole... [41:31] Life is like... [41:33] enjoying [41:34] making things for others and being in service of others. Like there's amazing, you know, entire professions and things that are all about that. And that that is amazing.

[41:44] I think that if you're interested in building something that you... [41:48] want to use? [41:50] And you also... [41:51] You also imagine yourself doing this for a long time, which is not a prescription whatsoever. [41:57] Lots of great companies get [41:59] built and then they get sold and then [42:02] People move on. [42:03] I often wish that I could, I've often had ideas of like, [42:08] writing books or comic books or making movies and like the allure of that is so appealing because like you make a movie it's done and then you make another movie you do a new thing and it's over you work on it for [42:18] Three years.

Yeah, but, you know, you work on it for three years or five years or ten years, but then you're done with it, and, like, that artifact is complete. But software is never complete. It's, like, always evolving, you know? It can't be because there's no firm ground to stand on. Like, the operating system is changing. Everything's changing under your feet. So... [42:41] If you're someone who really likes that idea of being able to move from one thing to the next, [42:46] Then... [42:47] maybe software is not the right category for you.

It's ironic given how much faster it is than other mediums, but I think that's right. [42:54] I was at Sundance this weekend, and there's something... [42:58] You can see I'm like [43:00] Maybe I'm projecting, but... [43:02] There's the sense of the filmmakers are doing the Q&A. [43:05] there is this crazy level of like, whoa, it's out, it's done. Maybe there's still work to do, but like the last five years have all come in. And software is a totally, if not inverted shape, a very different shape. Theoretically, you could work on Obsidian for 50 more years.

[43:20] to... [43:21] Yeah, I guess so. I mean, I think it's weird because... [43:24] I'm pretty sure like software is going to be different. The, [43:28] like, [43:29] in a major way. We might not be using computers in the same way that we do today. [43:33] Certainly, many of the... I don't know if we're going to have... [43:38] JavaScript and CSS and the way that we build apps... [43:42] Yeah, like the way that we build things... [43:45] change a lot or [43:47] There's so many things. It's so... [43:49] unpredictable you know what might happen we're all just going to be connected into the to the supercomputer well that's the unique thing about software too is people were making movies 100 years ago who's going to be typing with their fingers into a thing 50 years from now or even what is the oldest like computer or piece of software that anyone uses it isn't heavily heavily abstracted yeah huh [44:10] Okay, I want to shift gears a little bit and talk about design.

You are... [44:14] Again, when I said you were prolific earlier, and I really enjoy your writing, but I think from a design standpoint, that's kind of more what I meant, just given that. [44:22] When it comes to showing up with a strong point of view in many different forms, [44:27] even just chatting with you and hearing more about other things you've spent time on, you bring a design-focused approach and a really strong point of view to [44:35] most of the ways you show up in the world. So as a super basic kind of initial question, [44:40] What makes for good design?

[44:42] Wow. [44:44] And if you want to take a second part, what has made you a better designer? [44:49] I mean, constraints is what makes design great. [44:54] Gosh, this is a topic I've thought a lot about, but I haven't written that much about. And so I feel like my thoughts are not... [45:01] as organized as they could be. [45:03] You know, the way that... [45:05] I thought that I was going to become a biologist. When I was going through high school, I really focused my studies on physics, chemistry, and biology.

[45:15] decided I wanted to become a biologist and that I was gonna like [45:19] specifically become a zoologist or evolutionary biologist and then I spent some time that's when I went to school in in [45:28] college for [45:30] Then at some point I realized, like, I had been doing a lot of artsy stuff on the side. I had been making... [45:36] Winnempskins, I had been painting, photographing things, [45:41] I kind of dabbled with every medium at some point, just as it [45:46] as a hobby. [45:48] And I realized I kind of discovered design.

[45:52] like late because I think I was... [45:55] 20 or something i was in china i was at a muji store in singapore and i was like wait a minute [46:01] Someone has decided [46:03] what the diameter of this pencil should be. Like, it just sort of like dawned on me all of a sudden that [46:08] People had been making these decisions about all the objects that are around me. Did creative things become more serious when you thought about it as design? [46:16] Well, I just had never really thought about design as a profession.

I always kind of just had been... [46:23] messing around as like I didn't realize that it was people's full-time job to do this kind of thing. Right. [46:29] And this was like... [46:31] 2005 I want to say um and and suddenly it was like neo in the matrix like everything I was like just looking at everything all around me I was like oh someone made that decision and that decision and [46:41] this material and that diameter. And I was like, I could do that. I have opinions about what diameter something should be.

And so... [46:49] Then I decided to shift and try to become an industrial designer. [46:55] I [46:56] I lived in the Netherlands and I like... [46:58] Worked at it. [47:00] industrial design firm there. I went back to school [47:02] and study industrial design. [47:04] And then I met my good friend, Jesse, who became my co-founder for 13 years across two different companies. And we... [47:12] turned [47:14] you know, the things that we were passionate about in industrial design into software and like, how do we actually help other people manufacture things?

[47:21] Thank you. [47:21] I'm skipping a lot of steps, but you know, [47:24] All along the way, it was exposure to [47:28] having this other lens on the world where you look at things first from a biological standpoint, you know, when I'm like, [47:34] I have the choice to either study what nature has created and surrounds us with or like study what humans have created. [47:43] And [47:44] the human path seemed more appealing because I could actually contribute something as opposed to just like studying something that was already made. Right.

[47:52] I mean, in theory, I could have gone down like the genetics route or something. Maybe there's a hybrid of those two or like wetware or something like that. [48:01] I thought it would be more interesting to kind of apply my own process of natural selection to objects and interfaces and things like that. Cool. And then just by... [48:10] Coincidence? [48:12] This, you know, when I shifted into design, that's when the iPhone launched and it was like, you know. [48:18] just a total game changer in terms of what you could do with UI.

[48:22] and like, [48:23] the touch screen was so powerful because it really [48:28] created that connection between physical and the physical hardware and the software. Like you could literally make buttons that you can touch in EYs. [48:36] So that was really exciting and kind of [48:38] pushed me down that software path, but [48:42] Along the way, it's like, [48:44] You know, I... [48:45] I took [48:47] classes in typography and, you know, woodworking and UI and [48:52] studied things like just by going to like [48:55] the view source or inspector like [48:58] So I've just always had this curiosity about how things...

[49:01] how things are made, how they look, why they look the way they do, what is the structure of things. [49:07] I've had just like a lot of like curiosity. And then you kind of start to see... [49:12] patterns more you see patterns in nature and you're like oh it's again the question of constraints like uh [49:19] how do you know fibonacci sequence type of stuff like you look at how plants grow and how how they work and they're all like working within these constraints so [49:28] I don't know if I'm answering your question, but like the...

[49:32] Ultimately the things that make a system feel [49:36] appealing to [49:38] use [49:40] ergonomic intuitive understandable [49:43] beautiful [49:44] they tend to [49:48] find a way to distill what this thing is for into something that is... [49:56] easy to understand and the things that are easy to understand tend to somehow be [50:01] simple or understandable and so like that that's like the thing that i'm always searching for is how to make something understandable [50:08] And what's extraneous? What can be removed? [50:12] If you... [50:13] It's almost like if you reverse that.

[50:15] Story. [50:17] you would have a strong case for why so much of great design is so obvious, intuitive, or even invisible. Yeah. Yeah.