Changelog Interviews – Episode #492

Two decades as a solo indie Mac dev

with Jesse Grosjean from Hog Bay Software

All Episodes

This week Jesse Grosjean joins us to talk about his career as a solo indie Mac dev. Since 2004 Jesse has been building Mac apps under the company name Hog Bay Software producing hits such as WriteRoom, Taskpaper, and now Bike. We talk through the evolution of his apps, how he considers new features and improvements, why he chose and continues to choose the Mac platform, his business model and pricing for his apps, and what it takes to build his business around macOS and the driving force of the App Store.



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Notes & Links

📝 Edit Notes

Editor’s note: Technically Jesse has been doing Hog Bay Software for 18 years (since 2004). We rounded up to 20 years (2 decades) for the title’s sake.


📝 Edit Transcript


Play the audio to listen along while you enjoy the transcript. 🎧

So we have Jesse Grosjean here, who has been running Hog Bay Software since 2004. Jesse, welcome to the Changelog.

Hi, thanks for having me.

Happy to have you, Jesse. I think I’ve been on your mailing list for years, but I think you emailed me for the very first time in years a few weeks back, with the launch of Bike.

Yeah. I’m a one-person-do-everything kind of business, and I like programming a lot, and everything else - I kind of like visual design, and after that, it goes downhill quick. And my mailing list, once I send it out– in one week, I sent two newsletters, but the last time I think was 2018, so it’s up and down.

Yeah, which speaks to the challenge of any Mac developers, but we’ll get into that, of course… But that is the ups and the downs of one-person shows.

Yeah. Sometimes you have news and sometimes you don’t.

[03:59] It’s kind of nice though when you sign up for a newsletter and you’re like, “I’m interested in this, but I don’t want to get weekly updates on what’s happening.” And it’s like, when I hear from Jesse, pay attention, because he’s got something to say.

And he sure did this last time around, which was nice.

Good, good, good. Yeah. I always hope that– again, when I’ve done my little research on newsletter writing, they’re always like, “Send that once a month or everybody will think it’s spam.” And so I try really hard to make it no flashy graphics all this, but I still get spam reports of people saying, “You’re horrible”, and I’m like, “Ugh…” But I try.

“I never signed up for this. What’s Hog Bay Software?”


“Get out of my inbox!”

“I signed up for this in 2018.”

Yeah, “Come on, man. Email me more.” And I appreciate that sentiment though, Jerod, that you said, because sometimes I feel like you – especially when you sign up for a new service and they opt you into all the emails, that’s like the worst tactic ever.

And then you have to go un-opt in. I never did in the first place.


Just because I sign up doesn’t mean I want all your emails. And then they email you way too often with updates that are just not important to you. And then they become noise, not signal, and it’s actually negative to their brands. You’re like, actually, now I see the warts in your software more because all software has bugs, of course. And then you scrutinize their validity in your life, as we do with software.

We were just talking about like, I’m a user of past of WriteRoom, and I was like, “Oh man, Hog Bay software, I know this. I know WriteRoom”, and I had to remind myself. And then we’ll probably talk about iA Writer, and different things have happened in the writing app world in Mac, and I’m like, “I don’t use it anymore.” And it wasn’t because you sent too many emails, so kudos to you for not doing that… But there’s some software you scrutinize because they talk to you too much, they badge you too much, and they become noise and not signal, either in their actual software or in their emails. It’s like, “You know what? Just leave me alone already.”

Right. Yup. Although one of my resolutions here is that I send this newsletter more often than once every couple of years now that – I’ve got it all planned out now. I’ve actually got some big features, so watch out. It could be two months you might get another mailing.

Oh, boy. Oh, boy. Well, there’s one thing that I think people do enjoy, especially from Mac app developers, and dare I say, even indie Mac app developers. They tend to be indie more than they are mainstream. It’s just the way of Mac apps… It’s knowing the story, knowing - not so much like the day to day of Jesse’s life, so to speak, but why do you care so much to write Bike? Why do you care so much to put the work in, be a solo person? Why does that matter to you, and the details of making that work. I think the audience that you sell to could care about the story, and there’s a lot to a story that I think people often underestimate. When they go solo, like you are, and they have less people involved, a story can be more of a salient point than just simply the software you write.

Yeah. And I definitely think I probably don’t do that well enough, although… It sort of goes back and forth. Again, one-person show, everything’s a bit quirky. And so the newsletter, I said I get bad responses back. Mostly, I get lots of people saying, “Oh, I’m so glad you wrote. It’s been so long.” And so some people hear some about me that way and form an opinion and I’m fairly active in– I have user forums, but that’s pretty hard to keep track of. But for story, I did think of that. And my About page is updated more than a paragraph. I have pictures on it now. I have a dog in the background here…

They’re not clickable though. I can’t click them and see the sizes. I want to get into the details of your dog and your family…

I know…

…and this mountain that you’re hanging out on, but I can’t see the bigger version of them.

I’m sorry. Yeah. I thought about it, but–

It’s a step in the right direction.

It’s a step in the right direction, but you know, the kids and everybody… Who wants their photo on the internet?

Right. True.

Iteration. Well, they’re there at least. You do have kids. It is true.

You’ve been to a mountain before. You live in Maine, which I believe you have some mountains there. Hey, I’m a mountain biker and I want to go to Maine someday in my life to ride the hills you all have there/mountain you all have there, because here in Houston, Texas, it’s pretty much flat, it’s very trail, not a lot of downhill. So I look forward to going to Maine one day to mountain-bike there.

[08:26] Yeah. Well, I think depending on where you live, we have mountains or we most definitely don’t. We have got Katahdin, and that’s very mountain-like, although it doesn’t show up against Rockies and things, but it’s quite a hike.

I also tend to blend Vermont and Maine together, despite my awareness of geography. So forgive me.

Don’t offend him… Well, Jesse, the one story that I’ve known about you, not really through your writings or your About page, just through watching you write software over the years, from a distance - I don’t have a microscope out or anything… But if we look at the apps that you’ve written, all Mac native apps, we’ve got TaskPaper, which is plain text to-do lists, you’ve got WriteRoom, which Adam referenced, which is like distraction free writing, and now your new app, Bike, which is really a simple outliner… There seems like there’s some throughlines - the philosophy, maybe your viewpoint of what good software is. Plain text seems to be at the heart of it, some sort of focus or distraction-free or simplicity… Can you talk about some of the virtues in the kind of software that you like and why you like that kind of software? Why do you like to make that?

Yeah. So let’s see… So I wanted to do cool computer things in high school. That was my goal. And I was interested in graphic design mostly, because I liked Mac for some reason, I’m not sure why, and I wanted– Photoshop was the top of the… I graduated high school in 1995, so that’s the timeframe. And then I went to college and did computer science and studio art. Studio art was a minor, and more I like to draw and stuff, but… I like looking at visual things, but I’m not too much of an expert beyond that.

And anyway, so then after college, I did – again, interested in cool computer stuff as being visual, fancy buttons on the screen, not so much server algorithms, or things like that. I want to put things on the screen that I can click. And I went to a startup that was doing visual things. And then after a year of that I went and worked at the University of Maryland in their Human-Computer Interaction Department as a programmer, a research assistant kind of person. And that was neat in that it was lots of interface design kind of things. And in particular, they were doing zooming user interfaces where it’s a two-dimensional surface that you zoom into smoothly.

And so all of that was neat, and lots of experiments and cool demos, but in the end I also have this interest in taking notes on things, and I came to the conclusion that it’s really hard to get a zooming interface or any other fancy interface to be generally as productive as just like a plain text editor. If you put that information that you’re visualizing - and there are tons of exceptions, but I’m just talking about for a day-to-day, an average person. Well, let’s see… I put my grocery list in this text editor, and it looks just as good and as easy to manage as some fancier tool. And so that realization - which wasn’t immediate - that I came to, and I especially came to it with WriteRoom, where that was kind of just a fun idea that I did in a week and it got more attention and applause and money than stuff I’d worked on for years. So that got my attention, I was like “Hey, well…” So I wonder why that is, and stuff.

[12:20] One thing that I have come to think is that computers are magic. Maybe this is old news, but especially for like 1995, they’re the magic new thing. And I think that the real magic is pretty simple, in a lot of ways. For some use cases, it’s just like you can edit this text without retyping it, which is dumb and 50 years old, but that’s the big difference from paper. And all these things that we add on top of it are valuable, but if they get in the way of these core little things, like I can copy and paste text, or something… It’s always a trade-off and it’s taking away.

And so that’s been my assumption for a long time, is that for the kinds of things I’m interested in that are text-based, just a basic text editor is the foundation, and try to expand on that idea, but be aware that anything you do is going to have a plus and a minus, and that you might just be losing. It might be better to go back to the text editor.

You’re talking to the choir here. Jerod is a Sublime Text user. He will code in it and he will make his lists in it. He’ll write Markdown in it. He prefers it over any app that will give him extras on top of it. Jerod, you can speak for yourself, of course, but that’s the basis… And he kind of goes back to that every time. Like, I’ll use Notion, I’ll use things, I’ll use other apps, but it’s always text-based for Jerod. And I like that too, of course, but he seems to gravitate towards that first and always, versus move around different apps.

And I think you could save yourself a lot of time by doing that. Although for a programmer like me, it would be boring, because I want to try new things, right? So I’m trying to beat that text editor, but it’s hard, right?

And so anyway, with TaskPaper – I did WriteRoom. That was sort of a phenomenon, interesting, but if you add any feature to it, it’s no longer it. So it’s, at least for me who’s not interested in doing the marketing, at least not able to do the marketing, maybe I’d like it to be super popular and rich again, but… I sort of reached an endpoint where if I touch it anymore, I break it. And so TaskPaper was taking that idea and saying, “Okay, text is nice, because it’s this universal interface. What are a few basic things I can add to make it a little bit better for managing a to-do list?” And so I don’t know if people don’t know, but TaskPaper is a plain text to-do list that does some very basic syntax highlighting. For example, if you type a line and end it with a colon, it makes it bold. And that’s about all Virgin 1.0 did; very basic things, if you’re like a programmer listening to this podcast. Sorry…

It’s alright.

But I iterated on that for a while, that basic idea, but putting a model behind it so that it’s scriptable and you can write plug– not really plugins, but automate aspects to it, and style sheets and all that; trying to keep the basic, simple text part, but then allow people to extend it with their ideas. So that’s where I am with my apps now. I try to make very simple things that just have a few ideas, but then other people can extend them. And usually, the other people’s like the 1% of programmers, I think, but it’s the people who I interact with in my forums, and that’s kind of where I am and where I have the fun.

[15:51] Some of the features in Bike - and Bike is your new tool, it’s an outliner… The features that you list for Bike are things like opening files is fast, and scrolling is fast. And it’s 2022, and yet I read that and it kind of speaks to me, and I’m like, “Yeah, I want that.” And that makes me wonder, or kind of consider the bigger picture of maybe the macOS platform, or software in general, maybe the practices of the community… I don’t know what it is, but it seems like so much that we use isn’t fast, it’s bloated, or it’s laggy or it’s - pick your adjective - and it’s not fast. And so your features, which you wouldn’t think that– I would think today that would be table stakes, but it’s kind of like, “Hey, Bike has this”, and not everything has that. So I guess a two-part question - why do you think that is? And then maybe go into some of the things that you had to do in order to make Bike so fast.

Well, a few things. First, I’d ask people to test it out themselves, because there’s different ways to say fast, right? And so Bike is not a programmer’s text editor that can open a 100 megabyte log file. It should be possible, I need to change some things on the backend, but it isn’t now, sort of in the name of simplicity. But it’s fast for user-sized data. I use Moby Dick as my text file, because it’s bigger than anything I ever do. And that’s one thing; it’s fast for what it is, not necessarily Sublime.

For macOS, I think that a lot of text– I mean, the whole text system, it comes from 30 years – I don’t know, whenever NextStep was. They have a really hard job of supporting everything that was there and evolving it forward, and I can’t imagine trying to do that. So their standard text component that most applications are built on has legacy things that it has to support. And in particular, Bike is a fast outliner, and I’ve actually just been discussing with some people in some forums, “Well, why – is it really fast?”, everything. Text edits are super-fast on my computer already. And in many cases, text edit is fast, but using - go back to my other app - TaskPaper, which is based on NSTextView, which is the core component for macOS - basic scrolling is fast, but there’s all kinds of little weird things that happen. For example, if you resize a document in the middle, all of a sudden, it’ll get jumpy, and it might place– you resize the document, you place your cursor and it jumps to a different position. And so it’s little details like that that I’m trying to get right in Bike, which is– there’s lots of editors that get it right, but it’s some work to do, too.

And so I guess the question was, why is Bike different? I got rid of legacy. And then there’s two aspects of fast; there’s how big of a file can you open? And Bike is okay at that. It’s not great, but it’s good for pretty much anything people are going to use it for. And then there’s also scrolling performance and animation performance, and there, Bike is particularly– I’ve been careful. It’s using core animation, which is, I don’t know, since the iPhone, it’s been around… But most text editors aren’t built on that. And so I just do some basic things, like I only draw what’s visible in the text area, and I don’t lay out everything at once. I do estimation, and so that makes scrolling a bit tricky to implement, because if you’re scrolling up and your estimates are off, the whole screen is going to bounce around. So those are the areas where – I try not to do dumb things, and I don’t have to deal with legacy. And those are the two things that Bike is good at.

Legacy being like older versions of Mac? How do you describe legacy in this case?

Well, I’m just saying, compared to NSTextView, which is the standard - they have so much extra work to support that… I’m sure they know all these techniques just as well as I do, but to get it all to work on the current version and then 20 years of application API support is the trick.

[20:11] Yeah. One thing you mentioned too on the Bike page in terms of speed - and this conversation we’re having here is this Moby Dick Workout, which - you mentioned Moby Dick in your description there, but…

This is me marketing right now.

Moby Dick, yeah.

Not bad. I mean, there’s a GitHub repo for it, so you can actually encourage others to leverage your repo and use the zip files you have to do it on their own, basically.

It’s available out there. But you mentioned opening the file - it wasn’t fast. This is like, here’s the test, essentially. Scroll to the end, resize the windows - is it still fast? Scroll to the middle, resize the windows - is it still fast? Select all, cut-paste, undo, redo - app still standing? Okay. And I do those things. You make a list, you want to take it somewhere else… Because, hey, the app is very simple. You want to move it to an email, or you want to share it with somebody, because your app doesn’t really do sharing.

Like, I can’t share my Bike file with Jerod and we collaborate, so I’m going to want to eject and text my wife my list for our packing thing, or whatever, share this idea outline I’ve made with an outliner. So I’m going to want to cut it and paste it and redo and do different things. And so these are things that are common, everyday tasks when you use an outliner. And so you want to see if it still stands if it’s a big list, if I got a big idea or a small idea. So that totally makes sense. But this Moby Dick Workout is pretty interesting, to give your userbase a tool to say, “Okay, is this thing still working? It’s a new app, whatever. Help me troubleshoot.” And that’s smart.

Yup. Well, it has been – I don’t know when I… January or something, I was like, “Alright, what am I going to do here?” I was wondering… The real reason I made that it is because, previous to Bike, I worked from 2017 till last August on a big Rust project text editor where I did all the algorithms, everything to make it load gigabyte files, fancy, fancy… But I could never quite get it all done. And so Bike was, “Alright, what’s the simplest thing I can do?” And Bike right now, for the list of paragraphs, is just a flat array, which is a dumb data structure if you’re trying to make it performant. But actually, it does Moby Dick fine, so that’s why I made the Workout, because I was like, “Do I really need to be able to load a multi-gigabyte outline? Well, it would be extra work. Let’s try this for now and then I’ll add that later.”

What was the Rust app that you did? What’s the back-story there?

That I failed that– yeah, it’s…

Well, I wasn’t going to say failed, but you did. Okay, that’s fine…

Yeah, someday maybe… But another text editor, but with a workspace attached. I’ve been working on plain text for a long time, like you said, and that’s been the foundation. I always think, “Alright, plain text.” And so this was just the neck – and I’ve made TaskPaper and I made another app called FoldingTexts that are trying to allow you to have plain text, but extend it with other formats that… You know, how do you have your contacts in plain text, or something like that.

So this was a workspace where you could have supported different syntaxes, so a database. You have a whole bunch of plain text files, and then it would read the syntax from them and parse out a database and make it live, so you could have live queries of all these interesting things. All interesting, but I was going through huge amounts of work, extra work to support the plain text aspect, right? All these extra formats and syntax highlighting, and it still always looks kind of programmery at the end, right?

[24:00] And so Bike is not plain text. Bike is HTML-based or OPML-based. It’s a Markup Language-based. And I’ve decided that for me, selecting some text and making it bold just looks so much better, and I can think better with that than adding Markdown syntax or some other syntax, which I have advocated in the past, but it just–

I started taking notes on the iPad, just a little bit, in the notes program. And I was always sorts of notes being when I’m thinking through a design, and I was like, “Wow, these are easier to read than what I’m doing in my other tool, where I see all this formatting, and links…” Or FoldingText - I did a lot of work to hide that formatting, but it still makes everything complicated. And so Bike was just like, let’s get rid of that and just make something that’s easy to parse, but you don’t have to see all the syntax everywhere.

And you want to see what you get, the WYSIWYG , right? You want to see the actual end result, not the ** before a word and after.

Right. I mean, and it’s a trade-off, both ways.

Right. And it’s the audience really who you cater to, because there’s a certain audience who appreciates the visual aspects of Markdown, and what it gives them the ability to translate into, and maybe potentially the simplicity of it, but then there’s a whole different audience that is like, “What is that?”

“That makes no sense to me. Let me Cmd+B maybe”, because maybe they don’t even know keyboard shortcuts; they’re just like, “Let me select that and push the B button, or whatever. I don’t know how you get to bold.”

Yeah, I imagine, alright, in 10 or 20 or a 100 years, if you’re the perfect tool for thought - are you really going to want to have this syntax on the sides, or is there going to be some of… I just feel like there’s a huge trade-offl, I understand, but for me, I’ve been on one side of it for a long time and I’m really happy now with Bike that I’m on the other side of it, because it makes a lot of things easier… And not just for the end-user. Also, if you’re a programmer, you can extract the information much more easily from HTML than from Markdown. I think it’s a different thing, but it’s not necessarily a decision that is better or worse for programmers or for end-users and stuff, but we’ll see how it goes. But that’s my current thinking.

I’m just sitting here thinking about WriteRoom, because it’s been a while since I’ve used it. I assume it’s similar in nature to iA Writer, which was Markdown syntax, visual-first, not HTML bolding first. It leaned towards the side of like “Give me two stars before and after a word”, and that made it bold. And that was what you actually saw in the UI, which is where he began and now he’s anti-that, really, in Bike… Which is just almost a paradox. Almost. [laughter]


For example, people send me documents often, like something’s a bug or something like that… And the one big advertisement for plain text is that you can read it in a text editor, any text editor… But one thing I’ve found is that you can’t. It’s almost any large Markdown document that hasn’t been written for neatness in a plain text editor to start with. Like, if you’re writing it in a tool like iA Writer that wraps it, if you haven’t been really careful to take your links and make footnotes out of them and really make it clean, it’s almost impossible to decipher. The links are everywhere.

So that’s where I started to really wonder, “Huh, are my tools making plain text look good?” And it’s also selling the idea that it can look good in any text editor, but really, it’s tool-specific often. And so if you’re in Sublime and you’re writing Markdown, you’re probably very careful to soft-wrap the lines, make it look good, and then it looks good in Sublime, all the time. But if you’re in a tool like my FoldingText, it would do that automatically for you. So it looked good in FoldingText, but if you open it in Sublime, it’ll be a mess. And that’s one thing that I had with Markdown and plain text in general, is it’s somewhat tool-specific.

[29:59] So handwritten Markdown is portable, if I’m understanding you, because you wrote it by hand, and so it’s readable to you, because you wrote it… Maybe with some tooling help where you hit a link button and it turns a thing into a link, or like it pre-populates the Markdown for you… But you’re writing it by hand, like I do often, inside Sublime Text. But tool-generated Markdown is not as portable, because the tool is just generating the syntax, which is flexible enough that it might not look good in another tool, or to the human eye. And so you think you’re getting this great– I can read it like plain text, but oftentimes, you’re not. Is that what you’re saying?

Yes. That’s my opinion. I’m not saying it’s 100% true, but that’s–

…what I believe. I feel like if you’re working in a plain text editor, you can make it look really well, but there’s some work. If you’re writing Markdown in Sublime, you probably don’t do an inline link that fills half the paragraph, whereas that’s always what happens, unless you’re carefully curating what it looks like.

I think that’s fair, yeah. And I would say that HTML as a programmer is a pretty grokkable language itself, especially the simplicity, so far at least… I haven’t imported your Moby Dick, but I have put a couple of my outlines into Bike and edited and done things and then right-clicked and opened up the file in Sublime Text to see what the .bike file looked like… And it’s very basic HTML. It’s like an unordered list, with a bunch of list items in there, and they all have unique IDs. That’s pretty easy to work with, programmatically. So I think it’s portable, and I think it’s a good choice for this.

Does that hold true whenever you export? So as a quick test, I just went to my iPhone, which I happen to have – I was telling Jerod in the pre-call, “Let’s prep for this”, like “Oh, yeah, WriteRoom. I remember that.” And I use iA Writer, and what kept me there– I don’t use it daily, but I use it really infrequently, because I have old notes there. So it’s mainly because it’s on iCloud. It’s old notes that still matter to me, that I reference every once in a while. I don’t use it daily. I’m not taking my ideas and putting them there. So I’ve sort of abandoned it, but I have been a user of it. And I went and exported just some random thing from there. And I pull it up, it gives me a Markdown export, oddly enough, as a .text file, which - explain that to me; I don’t know why. Give me a Markdown file, but .text in the end. It is Markdown, and I’m opening it up in an editor and it doesn’t look bad, right? So I guess that might not be a good example, because it kind of is Markdown in the beginning.

Yup. And I guess I would say - there’s two things. One, really where this is coming mostly is TaskPaper. That’s the most of the files that I see from people, which is a nested list where if you don’t do text wrapping, then it’s – if you don’t wrap it into a nice block, then it streams around and it’s really bad. But for Markdown - I don’t know, I put links in a lot, and that’s where it really… The link ruins it. And again, ruins it is strong, but–

…that’s a big weakness I see. And so if you don’t have links and if you’re using pretty simple formatting, but as soon as you’re doing longer paragraphs of stuff that wrap, that are lists, it’s where it is bad.

Well, the nice thing about Markdown and HTML is that Markdown renders to HTML, and you can also take HTML, parse it and output Markdown. And so going from file, which is an HTML file, if you wanted Markdown out of that - well, you’re a programmer, you go and write a little utility that puts it back into Markdown. And maybe there’s an extension, because like you said, Jesse, you’re building a lot of these things as extensible. It seems like the things that you like are focused, plain text and extendable. And what’s interesting is TaskPaper kind of has an outliner in it.

[34:15] Yeah, it’s very much– it’s an outliner, but with plain text.

Right. It’s like a to-do-list, but it’s like your to-do’s are often outlined, right? Like this, and then these three things, and then go back. And so that makes me wonder, why Bike in the first place? Why pull the outliner out? Or why start afresh with just an outliner, which seems like it’s less capable than your existing product, which people already like, and are buying, and stuff?

Yup. Because TaskPaper, I think the first release was 2007 - and I haven’t been working on it full-time every day since then, but it’s gone through three major releases where the foundation changed. But TaskPaper is a plain text file format which is parsed into a model, and then that’s what the editor edits. And so the file format is essential to the app. You don’t want to change that.

And so for example, one feature that people want is to be able to bold text. And so the answer to that would be to add Markdown style formatting, right? And they also want to hide links behind – but with the other product that I’d done, FoldingText did all that stuff, but I did not like the end result.


And so if I wanted to push TaskPaper forward, I would start having to change some fundamental things if I wanted those things to be rich text. And also with Bike, I really want– one thing we haven’t talked about, it’s performant, but it’s also very animated, and like I say, fluid editing, which means that everything is very smoothly animated. And that requires that I write my own text editor, and that all of a sudden requires that I break– it would be impossible to turn TaskPaper into what I wanted to explore with Bike without also alienating and breaking TaskPaper in fundamental ways.

[36:16] Gotcha.

Yeah. You’ve got some foundation there that you just cannot avoid if you want to explore new ideas, essentially. So that basic question then - when you think about Bike and where you wanted to go with it, where did you begin? Was it a tool you wanted, or was it a tool that the users of TaskPaper said, “Well, I really want this”, and TaskPaper couldn’t be that for them, because they thought it could be, but it wasn’t? How did you begin to even think about what Bike could be? How do you design software?

Well, when I was– let’s see… So I talked about this big Rust text editor that I worked on, and I had some of these animation– basically, the performance part of the text editor and the smooth animation part of the text editor was from that project. But it was not an outliner, it was more a text editor. And so I had that that I’d been working on for quite a while, but I could see it, all of a sudden, as I was moving away from plain text in my mind, thinking it’s not carrying its weight for where I want to go; I was trying to look back through all my other project ideas and stuff and say, “Alright, what am I going to do with all this?” And so the Atom text editor, a while back - I don’t know when it was, 2014 or something, I made a test outliner in there that was very animated, was quite structured, meaning it was a traditional outliner, in that it had… Well, let’s see… I’m trying to remember what it was exactly. But what it was is I liked it a lot.

It was 2014, so…

Yeah. I liked it a lot, but when I said, “Hey, everybody, look at this”, I got a whole bunch of negative reaction from TaskPaper users, saying, “Eh, it’s too structured.” TaskPaper is an outliner, but there’s no rules. You can indent as much as you want, unindent as much as you want. The structure is derived from the text, instead of the text being locked into the structure, and this other animated one was not that. But I still liked the way it felt a lot. But anyway, I stopped working on that, since everybody said they didn’t like it. But Bike is that idea. It’s got all the fluid animation of that project, but it also has the complete flexibility of TaskPaper, where you’re not tied into the outline structure.

Yeah, the movie you have on the Bike landing page does do what you’re talking about justice. So listeners in the show notes, we’re going to link out to the landing page… The movie - just take a minute, pause even, and go watch it. You’ll catch up, essentially, visually how fluid and animated this thing is. It seems very fast, based on the movie. I’m assuming you’re just recording your screen and sharing a version of that out. It’s not like taking into after effects or something else to make it cooler than it actually is, right?

Nope. I’m not that fancy; just a screencast.

Right, it’s the real thing. It’s the real thing. This is Coca-Cola as a movie for an application you can use. So it’s super fluid, it’s super fast, and you can see how it works - indenting, outdenting, very, very fast and very animated.

Yeah, it kind of makes it fun to do. We’re just over here indenting, outdenting as we talk… What strikes me about Bike at first was kind of like - you’re talking about it being more fluid and less rigid, and yet because it’s like actually an outliner, for a while… I’ve only been using it for a few days, but for a while I thought, “I’ve got to put outlines in this thing.” And the way that I kind of scratch-paper my thoughts, which really this is, as you said, a tool for thought, it outlines very much that, right? …is you want to be able to think, and move around and dive in, dive out etc. And I just have a bunch of random crap a lot of times. I call it like a scratch sheet. is usually where it lives. And I have outlines in there, but it’s not all one, big outline. It’s not like I have this big, organized thing. It’s just like, I’ve got some outlines, and then I’ve got some words…

[40:14] Right. Yeah, my files are definitely full of crap.

Yeah. Well, it’s interesting, because as we’ve been going, I’ve been realizing, actually, you don’t need to outline everything, Jerod. Just throw some crap in there, and it works just fine. It is a lot more freeing now that you’ve kind of given me permission to just write at the top level every time. Because when I see the over-arrow - in the top of an outline it’s got the sideway triangle… I think like, “Okay, I’ve got to put a bullet point here”, but Bike doesn’t require that. It was just me that was thinking that it did. You just treat it like a piece of paper and then start indenting when you want to. So that’s nice.

And are you using the focus commands? You have to get comfortable with those.

No, I’m not. Teach me. Help me.

So what is it - Option, Command, Right Arrow maybe?

Oh, yeah. Oh, I just did it.

And so that’s how you focus on an item. So basically, my file, I just– and that’s where you get the nice… You slide in and it hides everything else. And that’s how I use my file.

Oh, wow. Yeah.

If you have a random idea, you start typing it and you get everything else out of the way, and then it’s there.

Yeah. So that’s cool. Thank you for teaching me that.

What makes that interesting is it’s like lists within lists. It’s almost like an application that’s much more rich, maybe even Notion level, where you have a page and a whole different idea. It lets you have the same feeling, without the complexity.

Yeah, like you leave this section and now I’m in this sub-section.

And I think all those apps are inspired by outliners. They’re like the next thing. And I think that’s good.


There’s all those tools - log, sequence or something, and then there’s some… I can’t remember the name of anything; I have a horrible memory. But all these tools for thought that are being talked about now are outliners, plus. And this is a native, small, little outliner just. But also, I hope to add – you know, right now it’s extensible through AppleScript on the outside. I also hope to add a plugin system on the inside, so you’ll be able to do things a little bit more like Notion, or these other tools. But my thought is that the outline editor will stay very much as it is, but then maybe you can have another view where you parse out and re-represent the data in some other form. So maybe you have context. I don’t know that actually anybody wants to store that in their outline, but you could store that in your outline structure, just like a text edit, but then you have it nicely formatted, with little rounded corners in another view, very much like how Markdown has text and then you generate a view. This would be structure, and then you generate a view. Anyway, that’s far ahead, but that’s where I’m thinking of going.

That’s interesting. One thing that’s missing - maybe it’s there and haven’t seen it yet - if you just added checkboxes, then you just get rid of TaskPaper altogether, right? Because that’s pretty much what this is. I mean, I don’t want to limit TaskPaper. It’s got a lot of features. But my point is, if I can just mark it off as done, now I’ve got a to-do-app, right?

Yup. I’m sure they’ll get in there eventually, but… [laughter] I’ve gotta release this thing.

So now you’ve just rewritten TaskPaper under a different name. Good marketing. You say you’re not good at marketing. That’s good marketing right there, because you can sell Bike as its own thing. You can start fresh.

Switch the foundation.

[43:52] Well, not many people are buying – I’m no good at charging for upgrades. So TaskPaper, the last thing I charged for was 2016, and this time I’m doing a different pricing model, which is exciting to me, because upgrades are always very painful to… You know, I think I’ve only – so from 2004 I think I’ve charged maybe three upgrades ever, because it’s just such a headache of trying to decide, “Alright, what’s going to be in the 2.0 release that I can finally charge and upgrade for?” etc.

And so Bike is doing subscription on the App Store, which I don’t really think that’s – I wouldn’t want to buy subscription, but that’s the way things work nicely on the App Store. But on my website, it’s doing the model where you buy it, you get free updates for a year. What you have continues to work forever, but if you want to get another year of updates, you pay some– it might be 70% or 50% of the price to get the next year’s updates. And so that’s really freeing when I think about it, is now all I need to do is generate value and I hopefully will continue to get customers without having to figure out all that other stuff of how to charge them.

Will that change things for you with something like WriteRoom though, where– I don’t want to go back to it necessarily, but that you feel like you can’t really add things to it? And then I guess the flip side of that would be - with TaskPaper, I noticed that in the footer you could buy it in the Mac App Store, obviously, and then also through Setapp. And for those who may know Setapp, it’s like a marketplace of many apps, where the user, me, pays one price, I believe it’s monthly… I forget what the subscription exactly is, but it’s based on – I believe, you get paid on essentially metering.

How often do I use your app. And then they take my monthly and then give you a portion of that. I’m just curious if you could speak to that aspect. Does Setapp make it easier for you to get paid as an app developer?

I mean, all of these things - it’s hard to know, because if I directed all my traffic to Setapp, then it would probably be different than how I have it now, which is I have it at the bottom of the page. But Setapp does generate some money for me definitely, but not– I don’t know, $500 a month, I think, I get. So it’s nice, but it’s not the final answer for me. I wouldn’t want to direct all my traffic to them just because who knows what happens.

I’ve had a great experience with them, but you don’t want to do that. And so I’m trying to sell from my website, where I can get the most percent of what I’m selling.

Right. You want to be indie. Obviously, you’re an indie Mac developer from the get, so you want to have control, you want to have ownership and say. And then giving that to Setapp, whether they’re great or not, kind of ejects you from that process. I’m curious, in that world, could you swap TaskPaper out? So to Jerod’s note, if you add checkboxes here soon and you pretty much create TaskPaper within Bike, can you easily swap out TaskPaper on Setapp and rinse and repeat or whatever, and just kind of keep– is that even possible? How much friction is it in the process of like– since we’re talking about selling and making money…

Yeah. I think that adding checkboxes to Bike still would not make it TaskPaper.

A lot of people use TaskPaper for the plain text aspect, and that’s the big thing I don’t want to support. But from an end user’s perspective, it kind of depends, right? But for the people who are hacking away at TaskPaper, I don’t see Bike as really a direct replacement. It’s a very similar idea, but it’s a different thing.

[47:55] But I would say that Setapp would be happy if I add Bike, and I may, in a couple months, I don’t really know, I can remove TaskPaper right away. There’s no super long-term agreement, I think. I’m not sure about that, but they’re happy to have it in, or happy to have both apps in, or happy to have it removed. I think that– they’re very nice. I’m happy with them.

Yeah. So they’re flexible…

Yeah, yeah.

…which is good for, I guess, you. It’s got to be a challenge for them, because if part of their lure to users would be, “Well, we have TaskPaper. Well, we don’t have TaskPaper. Sorry about that.”

It’s not so much a bait and switch necessarily, but it’s like, “Well, we thought you did, and you’ve got old screenshots that say you do, and now you don’t”, because the fluidity of the relationship is good, but challenging to retain.

Yup. And I haven’t paid super– it’s very possible that maybe there’s some agreement that you have to have it in for a year, or something. I’m happy to have it in for however long. I haven’t looked into that very much.

So while we’re talking the business end of what you do - you’ve been doing it for a long time, you have these three apps… I would love to hear what life is like as an indie Mac dev who’s obviously very good at what you do, has kind of put your stake in the ground of the kind of apps you like to build. Don’t love marketing, don’t think that you’re very good at that end of it. That’s a common sentiment, I think, amongst devs, indie devs as well.

We’ve seen stories of like the iOS store. You have your [inaudible 00:51:43.00] and you have your Flappy Bird people who blow up, but we know that on iOS it’s really tough to make a living as an indie dev, even as a small company, unless you’re in games or unless you get lucky or hit a home run. You can do it, but it’s not easy. I wonder if that’s the same on the Mac side. I wonder how your career has gone as an indie developer. Just give us the lay of the land. What’s it like to be a Mac dev?

[52:11] So again, I started– maybe like 2002 I started messing with it, because I knew I wanted to sell shareware; that’s what I was thought it was. And I was just also still working a full-time job, and then moved to Maine in 2004. That’s where I’m from. And so my wife and I moved back and she went to the university here for an extra thing, and I said, “Alright, Maine’s cheap. Let’s see if I can do full-time shareware stuff.” And from like 2004 until maybe 2012, every year it was up a bit, or a lot. And for a couple years, I hired some other people - I’m also not much of a manager, or a marketer - and it all went up, up, up, and then all of a sudden, I don’t remember the exact… Maybe 2012 or ‘13, it went down, down, down, and it turned into just me again, because there wasn’t enough money. And then it kept on going down, down, down, and it sort of… The dates are– they’re were within five years.

Sure. Plus or minus

Yeah. But anyway, up, up, up, down, down, down, and then just sort of low holding pattern. I could definitely make more if I was working as a programmer for a company. But gosh, it’s painful for me to do that, because I am really interested in exploring my own ideas. And I have done some contracting, and now this is the first– like I said, I’m not very good at business or marketing or whatever, but I haven’t released a new big app since 2016. I just do little updates to TaskPaper. And so that might be part of it, right?

Yeah, that’ll maybe do it.

Yeah. So yeah, I try, but it’s hard to– I’m more interested in exploring the idea and trying to get something. And when you have a product that in the end you fall out of love with, it’s tricky. So with Bike, the launch, looking back at history, it’s been good, similar to what I had when things were going well. And now that I have a solution where I don’t have to plan upgrades ahead and do all that, I’m hopeful that I can keep going. And since I kept going without a product that was new, things should be good, right?

[laughs] There you go.

My wife works. We have our house paid for.

We have expenses that aren’t too big.

So when you go to purchase Bike, it’s sold on your site. It’s not through the Mac App Store.

Although it’s both, but yes.

Oh, is it? Okay. I didn’t see that it was–

It’s there, but he promotes his own, because I’m sure you get the bigger cut and you get the better model that way, right?

Does that mean then the Mac App Store follows where you have like multiple versions on the Mac App Store, and you don’t put a new version there until, I guess, the year of free updates is over, or something like that? The question I’m trying to get to and the point I’m trying to make, just for the listeners’ sake, is that the license when you purchase it, it says it’s for one year of free updates. After one year, Bike will continue to work, but you must renew your license at a discount, in parentheses, for future updates. So you’re paying roughly $30 for a year of– it’s essentially yearly, based upon that.

A year of updates, but you get that software as it works forever.

You get that version of it for perpetuity, but if you want the new stuff as it comes out, beyond the year, you’ve got to pay–

Once a year.

…probably $30 or maybe a discounted version of that.

50% to 70%.

[56:00] And so on the Mac App Store, you can’t do that sort of model; at least I don’t know how. That’s why on the Mac app store, it’s just a subscription model, a monthly or yearly subscription. And I’m not super-comfortable with that model as a buyer, that’s why I’m generally pushing my website one. But I think it’s the best answer.

Is it the same price, or do you have the price things differently?

I mean, I don’t know. I’m making it up. I looked around at what some other apps were charging and I read some long time ago that it’s better if you charge more than less. And so on the Mac app store it’s $2.99 (maybe) a month, or $19 a year. And so my thinking is that, well, if you’re just doing it a month, you’re just trying it out…

…so you try it out for three bucks and decide if you want it. And then $20 a year, I figured it should be less than when you buy it from my website.

Right. So you don’t actually take 30 divided by 12 necessarily, or you kind of do almost–

Yeah, the monthly one’s different, but the yearly one is two thirds.

Gotcha. I see. So it says even when you go– I mean, we’re in the details here, but we’re just curious on how the… You know, when you’re a developer, you obsess over the experience of your users. And when you have to– when the hurdle is “Where do I buy it from and how do I buy it? Okay, do I love the software? Can I try this software?” All these steps in between you and the user actually enjoying all your toil, all work, and how you even maintain the indie aspect of your life - solo developer, that’s how you like it; these are the hurdles you have to deal with. And that’s why we’re in the details of this. Because even when I go to the app store, the thing I’m presented with, if that’s my way I like to buy software on a Mac, which is probably pretty common, right? That’s why people buy Macs. They have the store, and you can go there, and their security, or whatever the reasons are they go there, I’m presented with not a price, but the button that says “Get”.

And then next to it, it says “In-app purchases”. So I don’t even know how much it costs, so I might get into it and be like, “What is this monthly crap?”, you know?

Yeah. Yeah, the subscription stuff– but one thing about Bike is it’s fully functional without getting a license on either place. Fully functional. You can use it to load, save, edit… There’s just some preference settings that aren’t enabled and you can’t use AppleScript with it, but everything else works. And so it’s not a crippled app in the sense that it doesn’t function until you buy something. You can try it and use it as long as you want. And then if you decide, “Okay, I want to script this thing” - I don’t know how many people decide that, but then, okay, you need a license. Or, “I want to change the colors.” Arbitrary little things, but if you’re going to use it all day, every day, you might want those things, then that’s when you have to buy the license. So it’s not a crippled thing that you have to pay for it. It’s a free thing, but if you want to do certain things, you’ve got to pay for it.

You could potentially go– I’m pulling up Sublime Text a lot in this conversation, just because they have some good ideas. They did the deal where it was like shameware, where you could just use it in perpetuity, but like every 50th save or something like that, they’d be like, “Hey, you’re using this app a lot. You want to buy it?” Or whatever they said.

That seems like another way of just nudging people, but not – like, don’t cripple it. Don’t make it unusable, but just remind them, “You’re using this. It’s not a free app. It’s a paid app. You’re using it. You don’t have a license yet.” Just a little bit of shadeware, maybe. Just throw some shade at them.

Yeah. And that’s pretty much what Bike does. If you open it – because I looked at Sublime Text, and actually, Bike, if you haven’t licensed it, it shows a little unlicensed button in the top corner.

Unlicensed in the corner. I noticed that. Yup.

[01:00:04.28] You don’t notice it now though, right? But I mean, you did, right?

Well, I’m still on my trial. I just got it the other day.

And so I decided to do that, instead of showing up the dialogue on Save every once in a while, just because I thought– but I very much copied that idea from Sublime Text.

It makes you wonder, though, the choices an indie Mac App developer has to make… Like you said, Jerod, you’ve got your games and different things that have success on iOS. I just wonder if Apple has put in the thought to design the system to work well for indie Mac App devs. It doesn’t seem like it is. You don’t have a lot of choice.

I think it’s designed to work well for Apple–

…and hopefully, everybody else. And I think they’ve made steps slowly in that direction. I’m sure Jesse can speak of this, because he lives there, whereas we just observe. But I’m sure there’s things– even you, you don’t want to do a subscription. You’d rather apply the model that you prefer in the Mac App store I would assume, versus the subscription model, but that’s just the choice you have.

Yup. And it’s definitely– I don’t know. There’s a lot of people who know a lot more, and have opinions on the Mac App Store than I do. I would say that for me, the two things I really hate about it is getting my darn app approved. For example, with Bike, you submit it ahead of time, they review it. They say, “Okay, you’re good.” And then to do something like change a screenshot, you need to go through the process again. But since it was already approved, I’m like, “I’m good.” And then a couple of days before I changed the screenshot, and then whichever reviewer saw it next gave me like a list of - I think it was only two, but it felt like ten; it was like this doesn’t work, and I was like, “Oh…!” And so that kind of thing is frustrating.

If I was them, I can see why they made a lot of these decisions, and not necessarily just to benefit them, but just… I don’t necessarily think it’s all just Apple trying to be good for Apple. It’s a weird, hard situation, but parts of it can be very frustrating. I can assure you of that.

What would you change about it?

Well, that’s the problem where I don’t have a good answer, and I’m not really tuned– like I said, there’s a lot of people who have opinions about it. I use it, but really, thinking about the Mac App Store is very low on my list of things that I do. I am interested in my app, and then I’m like, “Alright, let’s see if I can shove it through and get it onto the Mac App Store.”

The changing part - I really don’t know. I wish they would support a different pricing model that would– this automatic pricing model. There’s a lot of apps that do it now, and I think it’s really fair to the user and unfair to the developer. And I also think it can make better software, because the developer is not always having to scheme, “How can I get people to pay an upgrade?” It’s just, “How can I scheme to make my software better over time?” So I would love it if they would support that model, but that’s my only thing that I’m sure would be pretty nice.

It’s a shame though, because obviously, the purchase is very much part of the relationship, and any Mac App dev is going rely upon the relationship between them and the end user. It’s the software, sure, of course, but there’s a relationship there, and you just said you don’t like to do it… And so if you don’t like to do it, then you’re not going to get necessarily as many sales as you could, or help as many people enjoy your software.

And so I feel like there’s just a bit more work to make someone like you - not so much love it, but like it more than you do currently.

[01:03:51.12] One, it would benefit the Mac platform, and it would benefit you, and it would benefit Apple financially as well if they would just listen more. So I’m sure there’s somebody in Apple that listens to this, they’re a developer, they’re somebody listening… Like, if you could give some advice on that note, what could they change?

I guess listen more, care about indie Mac App devs, I don’t know… Enable more relationship? I don’t know.

Yeah. I mean, I don’t know. I really don’t have too much opinion. I will say, I said the thing that I hate is when you go through the app review process. Well, if you’d asked me a couple years ago, I would’ve said that, and I would’ve said– what do they even call it? Getting the encryption right on your app was always a nightmare process, and would always break. And well, that works now for me. I’m sure every once in a while it breaks, but they automated some things. So they are listening somewhat. Another thing, recently they did– and actually a reason why I’m doing subscription is because previously they would only pay you 70% of profit. If you do a subscription, you get 85%. So that’s another nice thing that I am happy about.

Oh, right up front?

I have no idea. I don’t get it that detailed.

Because I know there was a real change when they went from 30 to 15, but you had to have a year. So it’s like the second year.

Oh, yeah. No, I think now it’s upfront.

Right up front.

Especially for somebody– if an indie developer… I think I’m under some program. I make less than a million in a year. And so I think I’m–


…under something.

So what percentage of sales for Bike? I know it’s early days, but what percentage would you say the Mac App Store is, compared to direct? Is it 10%, 30%?

2%. I don’t know. It’s very low.

2%. So then it’s like, “Well, why do I even worry about this thing?”

So that’s kind of the position you’re taking. If it was 40%, “Now I’ve got to think more about the Mac App Store”, right? But it’s less of a factor.

Yup, and I’m very surprised. I guess the thing is, all the traffic– I had a couple of… Like, the whole launch process– I am not an expert at the launch process. I got lucky and Hacker News liked me. And the same day I did Product Hunt, which I thought, before I’d had traction there like five years ago before… And Product Hunt - nobody cared, and it drove hardly anything. And so just complete luck. Anyway, all that traffic went to my website, and then I have a mailing list, and all that traffic went to my website. So that’s what generated all the sales outside the Mac App Store. In the Mac App Store I’m still mystified that it’s not getting– it’s featured on their Discover page, which is really nice, and I’m happy about–

What is?

…but it’s– I don’t know, maybe it had 1,000 downloads or something like that, total, which…

That’s kind of embarrassing for them, honestly. You’re featured on the Mac App Store and you’ve got 1,000 downloads?

Yeah, I don’t know.

I mean, is anybody using the Mac App Store? Maybe just no one uses it.

And that’s not sales either. That’s just downloads.

Right. So that is not good. One thing I always see a lot of in the Mac community, which I appreciate, is there’s a very passionate blogosphere, if we might still call it that. There is a lot of people who are covering–

Blogosphere. Yeah!

Yeah. The blogosphere in the Mac world is nice. There’s a lot of productivity people, MacRumors etc. iMore, which I think covers more than just Mac… But you know, gadget people. Did you go out and reach out to reviewers? You know, the Jason Snells of the world, and say hey Six Colors.

Yeah. My memory is terrible, and I’ve had a whole fire hose of email and stuff. So I can’t remember the exact ones that reviewed, but Bike did get reviewed. Sometimes a short, little “Just reposting it here.” I remember Mac Stories did a nice review of more in depth than the pluses and the minuses. I remember that one in particular. There was lots of other blog post kind of things, but I don’t want to start listing because I’ll then forget.

[01:08:11.16] But I have a list in TaskPaper of people who I contacted ten years ago, and so I tried to send out those emails again. Many of them still work. That was good.

You said embarrassing, Jerod. I think that’s embarrassing, too, that 2% of his audience is going through the Mac App Store.

And let me say, 2% is completely made up, but it’s–

Roughly. Yeah, I mean, it’s a good arbitrary number.

It’s anecdotal, of course.

Yeah. I mean, it’s like a single digits percentage-wise.

Yeah. I wouldn’t worry about 2%.

I wouldn’t optimize for 2%, you know?


So there there’s no encouragement. The point I’m trying to make is less about dwelling on the number and more like - you have no incentive to optimize for the Mac App Store on arguably the best computing platform for consumers. That boggles my mind.

Right. Let me give another perspective on that. TaskPaper, for example - that does about 50%-50%. So right now, things are skewed pretty high by the fact that I got a lot of traffic sent to my website.

You just launched.

Okay. So maybe over time, maybe a year from now, it’s a better number.

Because, I mean, why do you want to be on the Mac App Store? It’s because of Discover, right?

Unless you don’t want to do any of your own payments, which clearly you’ve already done all that work, that’s what it saves you, I think. It’s like, “I don’t want to do my own payments and I don’t want to do my own “marketing”. And so I want to be on the Mac App Store for Discovery, so all those Mac users can just find me, and Apple can handle that, and Apple can handle the customer relationship with the payments.” And if neither one of those things are doing it for you, it’s just not even worth it. Now, I think we should withhold some judgment, because you just launched, you got a whole bunch of direct downloads and purchases…

…and maybe over time, that Discovery engine churns and churns inside of the App Store and it moves up. But man, I mean, after a year, I’d be surprised if it’s 15%… I mean, sitting at 2%. Come on, Apple…

Well, since you mentioned 50-50 for TaskPaper, how then is the business model different? I see that when I go and search for TaskPaper, it’s $24.99 to purchase through the Mac App Store. I’m assuming that’s–

A flat price, versus subscription?

And so that very much might be a part of it, is that Bike is selling for subscription. But even the download numbers, like I said, are somewhat– I mean, I don’t know what good numbers are. I have no window into what real apps do, but 1,000 for the launch week is what I’m getting.

And TaskPaper - things definitely are skewed by the fact that I got a huge amount of traffic of people who already know about me and want to buy outside the App Store. So we’ll see.

So one thing I wanted to touch on with you, which probably should have been done earlier, but here we are and I still want to ask, is that you’ve been very supportive of open formats, of extensibility, of letting people extend and play with your software, and export, and share, and I’m curious if you’ve ever considered going full open source, considering that most of your purchasers are not going to be compiling and running it. I don’t think there’s a huge business downside for you on an open source – maybe even on your older apps that you’re not working on anymore. Have you thought about doing that, maybe you get some community built around that side, too?

I mean, I definitely have thought, “Wow, that would be neat”, but I don’t really dare. It’s kind of the thing where… Bike, for example - would I want to open source it? Oh, I have all kinds of visions of – you know, I’ve got this nice outlining text component that could be plugged into all kinds of more specific scenarios. I would like to do that, but I can’t really risk it. If somebody more energetic than me all of a sudden has a program that does everything mine does, I become less interesting really quick. And so that’s where I am right now.

[01:12:08.13] Too risky. Not so much on people not buying it, like compiling it themselves, but on people putting it in their indie Mac apps.

Right, right. Yeah, the buying aspect. And I have in the past– did I do shared…? I don’t know. I feel like I’ve shared source code with users sometimes, but it’s like the 1% of the 1% who actually want to change the app. I’m not real strict about that. I’m very make-it-up-as-I-go with all that kind of stuff. But just as far as making it open source completely - yeah, I don’t know…

What about WriteRoom or TaskPaper? These are done.

Right. Maybe. But again, they’re generating money. A little bit makes a big difference.

And I still– I mean, well not with TaskPaper. With WriteRoom, I have visions of a new one that does have some more features, but that’s still way down the road, and maybe it will never happen.

Yeah. If you open sourced it, it might remove your ability to make those future possibilities possible.

And probably WriteRoom– it’s a very simple app that has 1,000 clones. I didn’t invent the idea of a full-screen writing thing. I invented the idea of a small one that only did that. There’s other apps that were doing it before. So probably its biggest feature is the fact that it’s called WriteRoom, and it had its day in the sun. If I was going to make a new one, I wouldn’t want the source code to this old one. I would just start with something – it’s a simple enough app, I would start on my own anyway.

You’d keep calling it WriteRoom? Same name?

Oh, if I was going to make a new one - yeah, I probably would, just because that’s what people like.

Name brand.

Yup, something…

So since you said to WriteRoom how it sort of got to a place where if you added more to it, it kind of– I think I’m paraphrasing what you said, but it kind of went against its virtues, or however you described it…

Let me say I– it’s WriteRoom 3, which is the current one. I did add, but when I look back, everything that I added, I wish I could take away.

Okay. [laughter]

And so–

You should have released WriteRoom 4, but it’s actually just WriteRoom 1.

Right. Exactly. I could see myself doing that.

Many people would be mad.

[laughs] But you’d be happy.

Would you consider iA Writer a competitor to WriteRoom? Which came before? I don’t recall the history.

WriteRoom came first, but I do not compete with them. I think I am a small little bug on the windshield.

In comparison?

Yeah. I mean, I have very few sales. WriteRoom, I’m just keeping it as is.

Apple, right after I made version three, they cut a technology that it’s based on, so I have to rewrite it anyway. It was garbage-collected objective C, which probably if you’re a smart person, it would take you a week to fix it all, but I’m less smart, so it would take me a month… And it’s just sort of “Why bother?”

I was going to ask you your opinion on iA Writer. Since you have strong opinions about a simple interface like that, do you agree with the direction they’ve taken, iA Writer? Because this started out pretty simple too, very similar.

Not so much the same, but similar, simplistic virtues as WriteRoom. And obviously, it’s gone to iOS, and beyond to Mac, and iCloud and tagging, and folders, and all sorts of stuff.

[01:16:01.12] I mean, I think it’s well done, definitely. And I even use it sometimes. It’s one of those things where I tried it out for a while, like you, and then I don’t use it, but I have stuff in it. So I want to go back and look at it. I do very much have this feeling of really liking 1.0 apps. And then if you launch the old version compared to whatever the current version is, you’re like, “Ah, that was nice.” Again, I’m not super-familiar with what they’re doing now, but I think they have a file side thing, and I dislike that. Although, that’s the only reason why I have it anymore, is because I have files in it, so it makes sense of that.

Yeah. It’s less to talk crap about somebody, but more like this– the reason why I asked your opinion was less to say what do you do and don’t like about them, and badmouth them, or even praise them necessarily, but more this idea– because you said I have to add value to kind of get new sales, to get you to give me another year’s of your money, I have to keep adding value. And you start from a simple place, but yet to add that value, you have to add complexity, because I mean, features come and they add complexity, and things like that… And so you’re almost forced, just by way of making money, because - I mean, you can’t add users; maybe your total adjustable market might not ever grow, because it’s a pretty simple app. The Mac is only so big in terms of a user base, and there’s only so many people who need WriteRoom, TaskPaper, iA Writer, Bike. I mean, at some point, you’re going to run out of an addressable market. It’s just interesting how you take something very simple that you love, like you said, version one, and you get to version four, five or six or whatever the number is, and you’re like, “It’s kind of bloated. It’s kind of like, I don’t like this app anymore.”

And iA Writer for me was very much like that. I still like the app, I still think it’s amazing. The team behind it still amazing. It’s a beautiful, well done piece of work, nothing wrong with whatsoever, but the complexities just drive me away, really… But I go back because I have things there, you know?

Yup. And I don’t have a good answer. One idea that I’ve fantasized with Bike is, like I said, the core outliner part is just a text editor, and that’s pretty much the app right now. And I very much have been conscious of the fact that I always love my 1.0 apps. And then you’ve got to fix bugs, and then you’ve got to support some features, and you do that for a couple of years, and all of a sudden it’s not the 1.0 app anymore.

And so one idea - and I do not know at all that I’ll do this, but it’s something I wonder about - is to make other apps based on that that are using the same license. So right now, your people are either paying a subscription or they’re upgrading once a year. How do I add value to that outliner without ruining the outliner? And so one idea might be to make a bigger– this is where it gets hard, because each time you make a new app, it’s complex, and you have to make a new name, and all this stuff. But for example, make an outliner that’s dedicated to calendaring; but since I’m just a one-person show, I can do it under the same license, and so you won’t have to pay again. You’ll be getting new features, but you won’t be having the diversion ruined.

With Bike, I still have a lot of basic things to do that I do not think will bloat it. But once I start pushing up to those features where I’m like, “Uh, that might be one approach I take”, I don’t know at all if I will, but I kind of like that idea.

One killer feature for document tools, which Adam mentioned earlier, that certainly bloats it technically, but doesn’t have to bloat it in the UI necessarily, is collaboration. And it seems like that’s where a lot of things go, is collaboration. And to a certain extent, the web has made this really feasible, and has kind of been a killer app for people.

[01:20:06.11] We’ve just had Zach Lloyd on the show a couple of weeks back and he’s building Warp, a modern, futuristic terminal, and they want to bring collaboration to the terminal. He worked at Google on Google Docs for a long time. And just like the fact that that shareable URL that you can just pass to somebody and then instantly be collaborating on a shared document was so awesome with Google Docs that we just didn’t care that everything else kind of sucked for a long time… And to this day - I mean, it’s slow in the browser, for me at least. And I’m curious what your thoughts, because you seem to be very counterculture in that way. You’re very much like personal software for you, on your Mac, stored on your documents folder…

Now, I know Apple has provided some stuff, and they’ve started to– I can share a note in Notes app, with my wife, and we can both edit at the same time. Apple is bringing collab to native apps. They’ve struggled to do that. It doesn’t always work. I know there’s some frameworks stuff, but what are your thoughts on that as kind of like a big piece that is probably missing in the long run, but could potentially ruin the app if you don’t do it very well?

Yeah. So not my skill set… To do collaboration right now, I would have to run a server, and it would vastly complicate the application. I did think about it ahead of time, but for example my Moby Dick Workout thing - maybe Google Docs can handle it. But with me, I tried a number of these “they do all the work for you” frameworks for collaboration, and it did not work, and it bloated the memory from 50 megabytes to 500, or something like that. And so it–

It slows it way down. Yeah.

I would have to focus on that. I’m sure I could learn it, but it would require a year of work, and then I would have a server that I have to manage, which–

Maintain and scale.

Yup. And so I just think it’s–

Did you try Apple stuff, like CloudKit or whatever it is, like their “first-party” stuff?

No, I didn’t and I don’t know very much about them. I would say that, for example, hopefully, I will get around to doing a Bike for iOS 1, and they do have a Dropbox like iCloud. And that, together with Bike documents, are unique ID’s, so you could do some pretty intelligent merging. And so that would be how I handle that, is just a file service and then merge on conflict.

Big undertaking; it can definitely slow down the app, I know. Even in, my shared notes tend to have little things where the text disappears and then comes back, or the cursor hangs where it didn’t previously… So once a note becomes “shared” inside Notes app, which is Apple’s probably best crackpot team of programmers working on Notes app - even that gets slowed down. Therefore, you lose what makes Bike Bike…

The fluidity, the animations, the instant response and the locality of it all go out the wayside if you don’t execute perfectly. And you got network problems, which are never going to be perfect.

Right. Yeah. I mean, it’d be interesting to know – I’m sure there’s lots of one-person companies that run a website app, but I think trying to do a native app and a website service that all syncs it - too hard for me. I don’t know.

I was just thinking here as you were sharing that, Jerod… And Jesse, to your point that you said before, since you’re the holder of the license, you can create a brand new app. Maybe a future version of Bike might be called Buddy Bike, and the tagline for it isn’t “Tool for thought”, it’s “Tool for thinking together.” And so maybe the future version of Bike could be Buddy Bike, where it’s a collaborative version of Bike; it’s a whole separate app, but Bike stays Bike.

It’s got a different tagline… You can use either.

And it’s like, “Hey.”

What are the names of those multi-chair bikes where you can put like three people on them?

They’re tandem. They’re called tandem bikes.

Tandem bike. There you go.

I think the chance of it happening - it’s very, very, very tiny. [laughter] The collaboration – what I would like is… The other thing with these collaboration services is all of a sudden, the truth– I mean, I think there’s different, but generally, the truth is in the cloud, and it’s in some file format that is not… You know, your data is not an XML file on the disk, it’s the sequence of instructions that you’re sharing back and forth, right? And so another thing that you get with Bike, which you don’t get, I think, with most collaborative services, is hackability. The people in my forums are interested in, “Alright, I’ve got this Bike file. How do I generate a website or a Markdown or extract something from it?” And if all of a sudden the truth is on the web service… It’s possible, again, by writing APIs and stuff, but it’s different. It’s not right there, that you can touch.

Sure. Yeah. Those kind of folks in your forum that want a script - how big are they in comparison to the addressable market for Bike? Are they the one percenters, the two percenters that want to script and do unique things like that? Or is it a majority, or a small minority?

I have no idea. I don’t know how I would research that.

Because it’s new, right? You don’t know yet.

For me, they’re probably the ten percenters of people who comment in my forums.

But how many people comment in my forums, I have no idea, compared to the actual people using it.

Is that who you’re making Bike for, those kind of people who want to script and do unique things with–?

Because it’s a simple outlining tool, and at some point, the tool doesn’t do more than it could, because it’s just an outline, right? So you eventually want to take this thing and do something else with it.

Yeah. I’m trying to, one, create something for myself that is visually and behaviorally very elegant in what I’m trying to create. And then I’m trying to answer questions in the forums from people, and often the best way to answer it is– so I’m trying to meet them where they are. And so those are the two main factors.

I’m not very good at thinking about an everyday Mac App Store user who downloads it and what their experience is going to be. I hope I cover most of that under what I want the tool to be, this simple tool that just works, but I never talk to them. I don’t really know what they want.

[01:26:56.12] We’ve asked you a lot of questions, we’ve gone deep into the business side of things, how you think about software, why you keep your team very small - which is one person - how you actually make it sustainable… I guess we’ve grokked, to some degree, through the tea leaves, whether you like it or not, because you keep doing it… We haven’t asked you directly if you like it or not. It seems so.

I do. Yup.

Either that, or you’re sadistic, as you keep going… But we haven’t asked you– what have we not asked you that you can share? Is there anything else on your mind you want to share before we tail off the show?

I wish there was, but I don’t think so.

I guess try Bike, maybe?

Yeah. Yeah, try Bike.

He’s not good at the marketing part.

Yeah. Yeah. Some day. Some day. Try Bike.

[laughs] I’ve got one last topic that’ll be real fast.

One of the things that’s great about Mac apps are the cool icons, and you have a very cool Mac app icon for Bike. It’s bright yellow. It’s a silhouette of a head with a bicycle in the head. When you said you’re visual and you like art and stuff, I’m wondering - did you make this yourself? Did you contract it? Tell us the story, because that’s a lot of what the branding and what the feel of an app is, is like when I Command Tab over and I hit Bike, that has to have a certain look and feel. I think it’s a pretty cool icon.

Let’s see… I bought two pieces of clip art, and then I jammed them, and I actually…


You jammed them together.

Well played.

Yeah. I think I actually traced over them. They weren’t quite right, so I had to maybe redraw them, but using the two pieces of clip art as the template. But that’s pretty much– I’m glad you like it. I make most of my icons, and then sometimes people take pity on me and submit better ones. Although this one - I think I like it as well. I did intentionally try to make it flatter… It looks different than a normal Mac icon.

It does.

I’m trying to harken back maybe to make it a little bit old-fashioned-looking.


Yeah, vintage. That’s what I’m looking for. Yeah.

I think it’s cool. It definitely stands out in my list of apps. I think Mac apps have gotten less and less interesting, as Apple has, in their guidelines, made them very kind of uniform. Even Apple’s own apps have gotten more and more uniform over the years, to where you’re kind of like, “Is that the Slack app, or is that the Photos app? I don’t know. They’re both the same shape and have similar colors.”

Yours stands out, man.

On iOS, I will often click on my Photos app versus Slack. I mean, it happens all the time.

They’re darn near identical.

Yeah. That and like Google Maps. Google Maps, Photos and Slack are pretty similar. It’s like, “Am I going somewhere? Am I talking to somebody? Am I looking at my photos? What am I doing here?” Gosh.

What am I trying to do…? Yeah. Well, the old smash the clip arts together - that’s both good work, and the frugal way of doing it…

You really are a solo show. You just do it all.

Yup. That’s how it works.

Awesome. Well, Jesse, thanks very much for sitting down with us and sharing so much, being open with all that you’re doing, and… I think it’s cool. You’ve got your niche, you’ve got everything that you care about and that you love, and you’re willing to make some money, or make less money and just do that, because that’s what you’re interested in. I think that’s pretty cool.

Cool. Thank you.

We’ll put links in the show notes, everybody, to get Bike. Check it out, try it out, watch the video, at least, pause the show back when I told you to pause it and go check it out; links are in the show notes. Jesse, I appreciate you. Thank you for your time.

Thank you.


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