John Gruber’s Dithering podcast with Ben Thompson was the original inspiration for Crossword’s 15-minute format. Five years later, John joins Luke and Jonathan for a wide-ranging conversation covering open versus closed platforms, the history and impact of Markdown, and a missed opportunity in WordPress. Luke goes on about the good old days, Jonathan starts thinking about a rival platform, and John makes a prediction for the ten-year follow-up episode.

Transcript#

Jonathan: Our guest today is John Gruber. He’s an Apple journalist, a podcaster and a prolific blogger on DaringFireball.net. Now in terms of Apple, John is the foremost speaker of what we’ll call Cupertinoese. He’s also the inventor of Markdown, which we’re going to talk about a bit later.

John, when you and Ben started Dithering about five years ago, you kept each of the episodes to 15 minutes. And when Luke and I started listening about five years ago, we were like, “hey, we should do that too.” So from season two, of Crossword onward, we’ve done the same. It never really occurred to me to ask up until now - why did you guys originally decide to it for 15 minutes?

John:
That’s a great question. I think part of it is it was Ben more than me who drove the creation of Dithering. And Ben is a good friend and he had been a friend for years before that. And I’ve always been relatively open to expanding the John Gruber media universe, but also as as anybody who has followed, for example, the graphic design of my website, I’m relatively conservative about changing anything, because I would like to if I would do something new, I would like to be willing to say yes, that’s something I can commit to for a very long time. And hey, what? ⁓ Boy, I actually do forget whose idea it was that we would go 15 minutes, not a second more, not a second less.

But I think maybe it was Ben who at least initiated the general idea. And I was like, hey, I could do that because my podcast, The Talk Show tends to run long and I wouldn’t have the bandwidth to do that. I find my podcast, the talk show, to be mentally exhausting. And I try not to make that come across on the episode. I think they come across as very casual conversations, but I find afterwards, oh, my God, I’m done for a while and doing 15 minutes twice a week. It was like, oh, I could do that, even though originally when we first started during COVID in 2020, it was three times a week. But I do remember that we started thinking, hey, let’s do three times a week in COVID because we had nothing else to do with our time. But the idea from the start was once this COVID pandemic thing settles down, we’ll go twice a week. the idea was, I guess that’s the long answer.

The short answer is it would be the other extreme of my other podcast. My other podcast is about as long as a podcast could be. 15 minutes seems about as short as a podcast could be. And the extremes are always the most interesting to me in the media.

Jonathan:
I like it.

Luke:
Yeah. And that’s recording it on your time, but we’ve heard from people a lot that they love the 15 minute cutoff.

John:
Yes, absolutely. And it would appeal to a different sort of audience. Anybody who likes a two hour podcast a couple of times a month would also have time for a couple of 15 minute episodes a week. But also a different sort of audience who never has time for a two hour podcast might be interested in a 15 minute podcast a couple of times a week.

Luke:
So you said that your website hasn’t really changed much over the years. I think it’s maybe one of the famous websites of the ones that haven’t really changed. You’re not on Instagram. You’re not doing a YouTube video for every post - it’s not that influencer style thing. And you’re not a news site filled with images and ads and tracking pixels.

Daring Fireball is a blog. I love it because I love blogs, but it almost seems a little, I guess like anachronistic, you know? If you started again today, do you think you’d create a blog or is blogging kind of dead?

John:
It’s a good question.

I think for most and, you know, just to put the context in there, I started Daring Fireball in August 2002. So heading up on 23 years. For most of those 23 years, I would probably answer I would try to do the same thing. And today, if I were the same age, which was, geez, I was 29 at the time.

I doubt it, right, because I just don’t know that I would have the confidence. I wish I would like to say I would try to do the same thing, but I think I wouldn’t have the confidence that it would stick. And I think there is the room for it. And, you know, I’m not going to say that my audience skews crazily young and that I keep picking up young readers, but I pick up enough of them.

The basic idea is: do you want to read or do you want to listen or do you want to watch? Those are the three ways to consume media and they’re all valid. And I participate as a consumer in all three ways. But as a producer, even though I have the talk show, which is a big part of my revenue and income and the business and Dithering, which is the biggest new way that I - well, five years old, so it’s not that new. But fundamentally, I think of myself as a writer who also podcasts. And. I think that even if I were younger, I would still see myself that way and I’d have to figure it out.

But it’s tough because you don’t see many new “this is a thing you read” sites. But on the other hand, there’s the whole Substack thing, which I think we could and should get into, which sort of emphasizes that maybe there is still an appetite for something you want to read.

Luke:
Right.

Jonathan:
Yeah. One of the behaviors that surprised me in myself is that I continue to read Daring Fireball on a regular basis and your content’s great. But part of it is it’s one of the few sites that I don’t even think anymore about how non-optimized for mobile it is. I pull it up on my iPhone and I’m squinting. I’m not really, I have great eyesight, it’s just fine.

I’ve heard rumors that you’re thinking about a redesign at some point in the future or have been for a while. Is that the case? And part of this for me is like, it does work.

John:
Yeah, that’s the worst part. I’m kind of embarrassed about it because honestly, it should be mobile optimized so that when you pull it up on a phone, it should look perfect on a phone. You shouldn’t have to double click to get in on the text column. And at this point, it seems like a schtick that I’m pulling that it hasn’t changed at all. And you kind of get a desktop layup that with with one main column that when you do double tap or just two fingers zoom to zoom in on actually kind of does look mobile optimized.

Like once you get it to the right column width and scroll up and down, it actually does, you know, which is not exactly automatic and was something I set up in 2007 when the iPhone came out and it was like, oh, you know, this is pretty good.

It would have been better if the HTML plus CSS was such that there was no way to get to that and forced me to do it. And it’s a perfectionist streak in me that I would like to, you know, the adage is measure twice, cut once. And for me, it’s more like measure a hundred and twenty times cut once. At some point there will be and I don’t even want to call it a redesign, but just call it a refresh.

I don’t want to excuse, though, the way that it is. It’s not right and it should be better.

Jonathan:
Well, and you’ve been making improvements. Like you’ve updated the logo recently, you’ve had little flourishes to it. What would you prioritize then in like a redesign effort? Is mobile optimization the top priority?

John:
Yeah, because as it stands, mobile devices are the number one devices that reach the site. that’s the. ⁓ And again, and all that stuff is so hard to measure nowadays. And I don’t know if you guys want to talk about it or look at it, but I dropped Google Analytics years ago for privacy reasons, and I was like, I’ll replace it with something else. And it turns out I replaced it with nothing.

Luke:
Man.

Jonathan:
Yeah, same.

John:
And I’m like, you know what, this is fine. And I do run the whole domain through Cloudflare, ⁓ which, A, is primarily because it’s the easiest way to do SSL, and B, occasionally I do see things that I think you might want to qualify as a denial of service attack.

You know, there were a couple of things in recent years that Cloudflare claims came from Russia, where there were tens of thousands or maybe more per hour coming from Russia. And I don’t think they were like anybody trying to bring my site down, but just, I don’t know, weird bursts of traffic. And Cloudflare makes it so that you don’t even have to think about it. I only notice them because every once in a while I do go to Cloudflare and by nature of what it does, Cloudflare gives you some form of analytics. And then they’re like, you know, put like a little red icon next to the security tab. And I’m like, what’s that? I go and it’s like, you know, at six in the morning, you ⁓ had 4,000 hits in 10 minutes from Russia. And it’s like, what? And I didn’t even do anything, you know. I didn’t have to protect against it.

Luke:
Man, yeah. That’s awesome. I love Cloudflare for that.

John:
But just because the site’s been around for a long time that not why I’m not changing it. It does seem weird that the number one device that reaches my site has to do like a double tap or a zoom or something to get a good view. But on the other hand, it is kind of a schtick like, you know, until I change it to make it just perfect, ⁓ you know, it’s not too bad.

Luke:
Yeah, maybe we’ll all be optimizing for the Vision Pro. BUut don’t get me started on analytics though, John, like I’m, I think it’s a bit of a waste of time due to the amount of people who use ad blockers or ad blocking browsers and, then Cloudflare because it’s not cookie based. You’re going to get different proportions because you’ll get people hitting your RSS feed, you’ll get people on mobile and then if I’m on my phone hitting different towers, different IP addresses, all of it.

John:

And in the last few years, it’s very clear. And again, I’m not even passing judgment, but the A.I. companies are clearly hammering websites in a way that nobody else did. Like Google. Say what you want about Google, but they were very and continue to this day to be very respectful of individual websites, server infrastructure in terms of how often they hit.

And in fact, we could get into the whole thing about how that kind of led me to the business model of the weekly sponsorships because I had this idea circa 2005 or six to have paid access to full RSS feeds. Then when Google Reader became a thing, the idea was every single reader who subscribed to my site for 20 bucks a year would get their own custom URL with a, you know, 20 character unique string at the end. And Google Reader wouldn’t really handle that well because the idea of Google Reader was they’ll hit your feed once per hour and serve it to if you have 500 readers or 5000 readers or 50000 readers, they’ll hit your feed once per hour and feed that to everybody. But if everybody has their own URL, that doesn’t really scale to them.

But then in some ways, and that led me to the business model of, hey, what if I just sell a once a week sponsorship and put a post from the sponsor in my RSS feed? Then I could give the full RSS feed to everybody for free, which was great and has actually worked out very well for me. But at a fundamental level, I was never mad at Google for that because it was very respectful to the website that they didn’t want to hit it many times. Whereas the new companies coming up are like, “We’ll hit your website 60, 70, 80,000 times a day. No problem.” And it’s like that kind of throws off your stats, but also is very disrespectful. How much work is your website doing to service these sites or services?

Luke:
That’s interesting. Yeah, I mean. There’s some sort of connection in with Google AMP there as well. Like, is it doing you a favor by serving your website? Or is it, yeah.. But anyway, so that’s interesting that you’re saying that’s what inspired the ad-based model. And really like 2005, 2006, these are like the heydays of blogging, you know, this was like the golden era.

We’ve come a long way since then. This is what you sort of said that we should touch on earlier, right? Is blogging these days, it’s more of a subscriber model for the most part, right? People using Substack, Ghost is a big one. Oftentimes it’s not on WordPress for these models. There’s no real great, simple solution within WordPress to have this sort of subscriber model with payments and automatic emails and things like this. Do you think that this is like the natural evolution of blogging?

John:
I don’t know that any of it has been natural. Well, or I would say…

The natural era was the 2000s, meaning 2000 to 2009 or so. And that since then and again, part of it is the phones. Part of it is the ads. Part of it’s everything else. I don’t know that it’s natural. And I’m glad for Substack and even though I would discourage anyone from actually using Substack itself, I really would. And we can get into that.

Luke:
Well go on, get into it.

Jonathan:
Yeah. Yeah, why was that?

John:

Well, I think Substack is a trap. I really do. And because at one level - and again, there are exceptions, but I think they make those exceptions at the very edges. But for the most part, don’t you guys agree that you can tell if I sent you a link, if I said, “Hey, here’s a good article about something.” And I pasted the article into a group chat with the three of us. And you went there. For the most part, you’d tell right away, that’s a Substack site, because a lot of them, you know, they use that one weird font that. Yeah.

Jonathan:
I can totally tell, yeah.

Luke:
Mm-hmm.

Jonathan:
… And they’re all gonna ask me to give me my email address again.

John:
Especially once you scroll two paragraphs down and it’s like, you know, most Substack sites are whatever the name is, substack dot com. It’s right there. They put the Substack part first. And I don’t think that’s in the interest of anybody in independent media. And I think if you look at anybody who has succeeded independently in this online media racket for more than 10 years, which I hold up as a number. It’s rather arbitrary. But just as a number that says you’ve withstood multiple trends, right? 10 years is sort of across a couple of trends. The ones who are standing for more than 10 years ago tend to be fiercely independent, including in their technical stack. You know, there’s me, there’s Kottke.org, I love that site, Taegan Goddard’s politicalwire.com, which I think runs on WordPress with Memberful as the sort of gating thing.

But anybody who’s done it for more than 10 years has a technical stack and there’s no correlation between what we’re using in terms of which CMS or which gating interface, but that it’s something that whatever we are using, it allows us to be fiercely independent technically.

Jonathan:
So I see a chicken and egg problem here, John, because part of the allure of something like Substack is it lowers the barrier of entry to jump in and get started, right? But I agree strongly. Like there’s this, I always question like, okay, what are the incentives behind the scenes? I’m like, what are the private equity incentives or whatever the case may be, whether Substack has that or not. But for me, I can see someone, who just wants to write. They don’t want to go and figure out the stack, right? They don’t want to have to figure those things out. So in my mind at least, then it’s like, well, maybe the ideal here is to say, “Start on Substack, that’s great.” But like, let’s change the conversation to be more of: be aware of your options and recognize that there’s a point of graduation. And then what does that look like? But to me, it’s a bigger topic about open versus closed.

Luke:
It doesn’t have to be Substack though. You know, there are other options. Ghost actually ghost is a great one.

John:
All right. Yeah. And well, and again, I’ve written about open versus closed in so many different ways about platforms and stuff. And at the same time that I am fiercely independent about sticking to openness in terms of what I do, you know, Daring Fireball itself, RSS as my distribution at Daring Fireball and podcasting with The Talk Show and even with Dithering where Dithering is a paid podcast. Right? And you have to pay five dollars a month or be a subscriber to the whole Stratechery package.

But what you get when you pay is an RSS feed of podcast episodes that you can do whatever you want. You can subscribe to that feed in any podcast player. And if you want to write your own thing that sucks in podcast episodes, from RSS, it is a bog-standard RSS feed that you get from being a subscriber. It’s not open in terms of being free of charge, but it’s completely open in terms of once you pay what you get is an open standard. And I think when you look at Substack and where they’re pushing and where their efforts are going, it’s pushing everything towards their app, wch is the Substack app for mobile devices, which is to me way too many things at once, where it’s like an RSS reader for the actual newsletters you paid to subscribe, but it’s also a Twitter thing where, know, or whatever you want to call short form posting. A Twitter like thing like Mastodon or Blue Sky or Things or X or whatever else you want to call it.

But ultimately, and they really want you to use that instead of the newsletter thing. And when you look at the company, it is a company that has raised a lot of money. They’ve had a raise. Ana Marie Cox. I didn’t link to it yet, but I’m going to from Daring Fireball. But, Anna Marie Cox, who has been blogging since around when I started, had a good post where she actually just like looked up and documented it, where they had like a weird fundraise two years ago that obviously wasn’t going to work. They weren’t going to get nearly what they wanted. And then they kind of did like a sort of like a Kickstarter where they raised some money from people and it’s just all really it just reeks of they’re spending more than they’re making. And there’s no reason that they shouldn’t be making money for what they do at a technical level.

Like if it was you two guys who made something like Substack, you’d be way in the black. But they’re not. They’re way in the red because of red flags that people should be raised. And the other thing that I think Substack has and it’s, you know, I say people should be aware of it.

It’s not inherently wrong, but they’re they’re playing on the fact that they’ve established a certain je ne sais quoi brand for Substack itself that appeals to a certain mindset of, for example, I’ve never met him. I wish I did because I would chew his ear off and beg him to switch to Ghost or WordPress or something. But like, Paul Krugman, who had written for the New York Times for over 20 years, one of the most astute political and economic commentators of my lifetime. He parted ways with the New York Times, and now he’s got a personal thing on Substack. But I think to someone like Krugman, there is a certain mindset of I would like to be part of a bigger brand.

He went from The New York Times and now he’s at Substack. And if you do video, maybe you were at CNN for 20 years, but now you’re at MSNBC. But it’s still you’re on TV and you’re on this thing as opposed to just opening your own channel on YouTube all by yourself. And again, YouTube is kind of different because you’re actually not independent, you’re part of YouTube.

But the advantage of writing versus video is you don’t have to do a thing like YouTube, right? It’s it’s a little different. You really could do your own thing on Ghost and nobody needs to know you’re on Ghost except CMS nerds like us. And you’d get this 95 percent of the same audience. I don’t think Substack actually drives more audience.

I think Paul Krugman’s audience would follow him no matter where he went. I think if he hired a nerd to just write him his own CMS and create his own thing so that it was the Paul Krugman CMS, he would still have 95 % of the audience that he has now.

Jonathan:
John, do you think in Paul’s case that it is more like the clout that he’s after? That’s what I’m wondering because did it not occur to him to like, and maybe, because what I’ve seen too, because I have a background in publishing, what I’ve seen too with folks is they get overwhelmed with the idea of finding that nerd, if you will, or like, who do I go to?

John:
I don’t think he thinks about it, right? That’s the thing.

And I think there’s a there’s a traditional mindset. Books are another great example where when I was younger, self-published books were the realm of kooks. They really were like if you wrote a book..

Jonathan:
Yeah, yeah. You need a legit publisher.

John:
Yeah, and it could be small publisher. It didn’t have to be one of the big five. But you want you wanted a real publisher and a real publishing editor and stuff. A self published book was a sign that you were a kook and you know fair or unfair but I think it was in practice mostly fair isn’t true in the modern age right there are great great ebooks that have been written and self published you know if I ever wrote a book an actual publisher would have to offer me extremely good terms not for me to self-publish it.

But that mindset is there for people of a certain age. And I’m in that age, you know, I’m not passing judgment, but it’s sort of like if self-publishing your book is a sign that you’re a kook and you’re self-publishing your online writing.. and again, Paul Krugman shouldn’t have any doubts at all. He’s, you know, he’s one, one of goddamn - and rightfully so, a fully justified Nobel Prize in economics. You know, one of the great political commentators of the last 20, 25 years. But I think that’s just sort of baked into his brain that you don’t want to just go out on your own because then you look a little flighty and kooky. Whereas I think to me, no, that’s exactly where you want to be, because then you don’t have to answer to anybody.

Luke:
Let’s pick up on that open versus closed thread that we left a little while ago. In my early career, I was in my twenties, and I had like all of these big heady ideas, maybe naive ideas of like championing the open web and like open source technology stacks fighting against closed platforms. Kind of seems like these days that that’s like a lost battle, you know.

My wife, for example, she’ll look for businesses on Instagram and WhatsApp for group chat. People get their news from Facebook or Twitter or Apple news for news, maps. If you’re trying to like look up everything, it’s got an app and sometimes I wonder whether the web is sort of, if not for nerds like us, right. But in the popular imagination has the web kind of lost. I don’t know, sounds a bit down, but sometimes on my bad days, you know, what do you think?

John:
Huh. You’d think I’d think about this more often. I think that practicality has reached a middle ground that when you examine it on particular issues, zigs and zags, right? So instead of being entirely red, let’s just assign red to closed and blue to open.

The world is very purple. But when you look at it individually, well, this or that, there are parts that are very blue and parts that are very red. And the overall situation, though, is kind of purple. I do think that in 2025, the overall Internet media landscape is more closed than I then I wish it were and certainly more closed than I thought it would be 20 years ago because of platforms like all of these all of these successful platforms. Instagram, everything meta does. They’re all a bit more closed than I thought the world would be. And, you know, and then there’s Mastodon, which is very open in the whole Fediverse and isn’t as popular or as usable and I think has some fundamental design flaws. But overall openness seems to be holding its own at like the core levels, right?

Jonathan:
Sometimes it just takes a moment as well. Because if I think back to where WordPress sort of got its kickoff, there was, what was it Six Apart? Six Apart, there was Movable Type, right? There was this, ⁓ and well, you’d know the history better than I would, but there was a big exodus from it with everyone except John Gruber leaving Movable Type. Just a couple of folks remained.

John:
All right, well. Kottke’s still there.

Jonathan:
But when I think about proprietary for a moment, something like Substack, I can just look to the future and see a moment where there’s a revolt, right? Like Etsy, for instance, was just really just gobbling up all the market of the indie artists. And now when I go to like farmers markets and other places, there’s a bit of a revolt because the fees have gone way up. People are looking for alternatives.

John:
Well, and I would even say that looking back at the Six Apart / Movable Type versus WordPress in a way that WordPress just sort of took over the CMS world as quaint because whatever you wanted to argue about how closed Six Apart was approaching the licensing of Movable Type, it was still a thing that you installed on your own server and you ran your own database. And once you installed it, you had a perpetual license, at least to the version you were running and you could keep running it on your server, which is way more open. Again, not open source, you know, but compared to publishing everything you do and the way that there are entire influencer brands that run entirely on YouTube entirely on Instagram or whatever you want to say, way more open, right? Like from their perspective. So it’s all relative. ⁓

But I do think, I think it was un, not, not, I think a wise enough person would have said somebody’s gonna figure this out. And I didn’t. I thought, man, I just remember thinking in the early days of the web, this is so great because we had this we, meaning anybody, meaning any freaking kid, anybody who could just freaking get to a keyboard on a device that was connected to the internet, we, like the friggin’ world, could…

Luke:
I think at the time it was called the blogosphere.

John:
Yeah, but it was even bigger than that, though, where you could just write, you know, even a little bit before that, where people had finger files, right? John Carmack used to write these crazy updates on his finger. And there was just this idea that anybody who could get to a device connected to the Internet and get an account in some way on a server that was connected to the Internet could have a presence that anybody else could reach.

And you could just sort of put your shit out there in any format you want. Meaning like, you know, just down to the character levels where it’s like, is it RSS? Is it HTML? Is it just plain text? You know, you’re just putting text files out there, but that you could just put stuff out there and people would find it if they wanted to and read it.

Luke:
Yeah, what a time.

John:
But at the same time, the thing that was amazing at the time and that made it seem like it was sustainable and would be the future was we weren’t asking, we meaning not anybody who was doing this, we weren’t asking to run software on your device. What we were saying is we’re gonna put this thing out here in a publicly accessible URL.

It’s a string of text that you could access from any device anywhere in the world. But if you knew the URL and you did a GET on that URL, you would you would literally GET - which is a great verb - the text of that content on your device. So we weren’t asking to run software on your device, which is a huge ask.

And a huge security risk and, you know, but it was this idea that you could distribute your content digitally without asking or requiring to run software on the devices asking. It was “Here’s my stuff. It’s in this format. You get it in that content format and do what you want with it.” And I thought that was the future of media. And it still is the present of media to some way, but it’s not the only present. And the majority of media consumed today is consumed through proprietary client software. And I think that sucks in some ways.

Luke:
Yeah. I wonder how much of that is like a trick of just technology not being good enough too, because you’re talking about text, but the reality is that most of us can’t really afford to be serving videos and even audio.

John:
Yeah. it’s still to this day, to this day. I started podcasting with Dan Benjamin in 2006, 2005. I forget when. But when we started the original run of The Talk Show, it was a real stretch to distribute MP3 files of hour long podcasts. You know, those were very big media download files. And I forget how we - I think I’d remember. It was one of those things where I was like it was like part of the deal “Dan, you figured it out” and he figured it out. But it was a huge deal. Just the audio only. Video was like, forget about it. You know, but it was a huge deal that we could distribute whatever and I think those early episodes, if you find them on the Internet Archive, they are pretty good quality audio wise.

But it was a big deal. We couldn’t just put them on our web servers the way I do if I post an image to Daring Fireball. They were way too big and you would pay significant money if you went over your download limit.

Luke:
Yeah. So, that was like 2007, right?

John:
Yeah, and video was like off the charts. And even to this day still is. Nobody, almost nobody distributes video from their own website. It’s incredibly expensive.

Luke:
Look at us. I feel like an old man already just sitting here reminiscing on the good old days of the Internet. But you know, that was the same time that we got the iPhone and actually the very first iPhone as ⁓ you know, as I’m sure you know, didn’t even have any apps on it. We still were using the web browser for all of those apps. And we had like this sort of, it was web 2.0 peak man.

It was all about web apps and responsive design. Even though that’s not a term you’re familiar with, optimizing for mobile..

John:
I am familiar with it. Very familiar with it. I hear about it from readers all the time.

Luke:
..So my question then is: obviously Apple stepped away a little bit from that and they’re all about apps. How much does Apple and even like given its stewardship of WebKit, how much does Apple still care about the web?

John:
Oh, that’s a really interesting question. I think they care a lot and I think it’s really interesting the way that multiple factors came together to make the iPhone possible. And one that I think is largely overlooked is the creation of WebKit and Safari, which I forget exactly when they started it, know, 2001, 2002, I don’t know, Ken Kocienda’s Creative.. I forget the name of his book now, Creative Whatever..

But, and you know, and Tim Cook to this day - there’s this idea of called it the Cook Doctrine and the primary tenet of the Cook Doctrine is that Apple, based on some quotes from Tim Cook back then, that Apple needs to own and control the primary technologies that they use to create their devices.

And the idea that a web rendering engine and web browser would be a primary technology that they need to own and control is a very interesting idea that when Safari first came out in 2002 or three or whatever year it was, it wasn’t seen as something Apple needed to do because there was Internet Explorer that was native for Mac OS 10 and bundled with Macs and it was good enough.

But and there were things like.. what was the version of it was sort of an offshoot of Firefox, but but optimized for the Mac. I’m forgetting the name. What was the name of that? ⁓

Jonathan:
Yeah. It was some other creature, if I’m recalling correctly, but I don’t remember.

John:
Yeah, yeah. But it was kind of interesting because it used things like native cocoa buttons for if you just had a push button in a form on a Web page, it actually looked like..

Luke:
Camino.

John: Camino. That’s it. That’s it. And ⁓ Dave. ⁓ geez. What was his name? Camino. And his name is Dave.. Dave Hyatt.

I’m pretty sure Dave Hyatt is actually still at Apple and Dave Hyatt back then used to blog extensively. He’d blog like every week and then like he learned his lesson, which was, you know what? I’m going to disappear from public life. I haven’t seen Dave Hyatt in many, many years, many, many years, but I’m pretty sure he’s still at Apple. And it’s kind of a shame that the way that being public about your work kind of led people to be like, you know, maybe it would be easier if I just did my work without writing about it publicly.

Camino. Camino was amazing in some ways because it had flaws. But in other ways, it was like, yeah, but if you just had like a generic form tag and a form, you know, just all the generic HTML standard tags for a form, put them on a web page, loaded it up in Camino.

Luke:
Mm. You get those beautiful aqua buttons.

John:
It looked like a native app and it was like, oh, that’s kind of neat. And Dave Hyatt at the time, who was the man behind Camino, was like, yeah, this was really hard to do. Camino is sort of the wrong route to do this. And it’s no surprise that Apple recruited and hired him to help build WebKit and Safari to like do the same thing the right way.

But in addition to the fact that Safari debuted in 2002 or 2003, as in my opinion, right out of the gate, the best web browser for Mac OS 10. It laid the groundwork because a WebKit, for the iPhone in 2007, where they owned and controlled and fully understood and had super talented engineers to do everything you needed to do so that when Steve Jobs stood on stage at Macworld Expo in January 2007 and said, hey, this isn’t the baby web app web for mobile phones. What was it called back then? Like there was like a stupid name where, you know, for like the you know, if your site was like big company dot com, you’d have m dot big company dot com and it would load like a like a little. Yeah, and it was, you know, it really did suck. And it was like, no, you were just going to go to the real New York Times and load this. But it WebKit in 2007 had to do a lot of really weird things from the perspective of a desktop PC browser to make it look right on a little tiny 3.5 inch touchscreen with finger zoom and owning and controlling that was a huge part of what made the iPhone the iPhone. It was it was no surprise if you go back and watch, you know, I’ve watched that keynote more than probably any other that Apple’s ever done.

It was a huge part of it. It really was. They knew it was a big part of the appeal. It turned out it really was a big part of the appeal. And I think to this day, they appreciate that to the point where it almost excuses some of the things everybody complains about, what they do through the App Store, because they’re like, hey, if you don’t like it, go to the go to Safari and ⁓ do your thing on the Web. You know, and it’s great on the iPhone, you know, and it really is.

Jonathan:
Yeah, it really is.

So John, I want to touch on WordPress a bit here, but connect it to it because I remember for me it was a couple of keynotes back during WWDC that I got to see the WordPress logo in a keynote for the first time. I’m curious, and it was just a reference to the WordPress app, right, that you can use to publish on your iPhone to your WordPress install. Where did WordPress, like when and where did WordPress first come onto your radar?

John:
I don’t remember exactly, but it was after Daring Fireball had launched in 2002. And what was the thing that WordPress was forked from? remember that one?

Jonathan:
B2.

Luke:
B2.

Haha.. Look at us both here with our trivia. “We got it! I got it! I know the answer!”"

John:
I remember Greymatter. I know, do you remember Greymatter? Which was more like the predecessor to Movable Type.

Jonathan:
I’m curious especially about your early impressions of WordPress. When it first came onto the radar, like what was your impression?

John:
My early impression was just, hey, that’s another cool new CMS, you know, that people, you know, like Movable Type, like Greymatter, like B2, like whatever, whatever, where you could download the thing in a zip file and then you would upload it by FTP to your web server. Follow some instructions for setting it up.

Everybody at the time pretty much used MySQL because, and again, I think the world would probably have been a slightly better place if SQLite had been a few years ahead of itself..

Luke:
Yeah, that’s interesting idea.

John:
Because, well, I think an entire database server was and still is overkill. I run Daring Fireball with a backend with still I have a MySQL backend for it. I don’t need it, but it’s because that’s what Movable Type defaults to. It is sort of overkill, right, to have this whole online server for it. Whereas SQLite is incredibly I mean, it’s just it’s actually more efficient than file system in so many ways.

Jonathan:
I wonder though, and this might be a question for you Luke, like I wonder with the decision to have MySQL, John, it’s part of WordPress today, one of the things that might surprise folks to know who didn’t is that it’s the biggest ecommerce platform. If you just take WooCommerce, which is a plugin, right? And it’s like, is that a byproduct of it having overkill in terms of the database, even though that’s one of the biggest areas that’s faulted as a weakness today, but that overkill, if you will, opened up this.

John:
Without question, right. Yeah.

Jonathan:
People creating these entire applications, like within this WordPress context, and ecommerce became the of the runoff success.

Luke:
So I actually don’t think we’ve talked about the fact that your blog isn’t on WordPress. I don’t think we called that out explicitly. You use Movable Type, if I’m not mistaken.

John:
All right. Correct.

Luke:
And that’s actually that’s one of the few blogging platforms that’s sort of still around. That’s sort of still around that that out dates WordPress even. So my question would then be like, why have you stuck with Movable Type all these years? But also what can the WordPress community, what can the WordPress project learn from the fact that you decided not to switch?

John:
I think it is, and again, it’s almost detrimental to the mindset where there’s this whole new thing, and again, it’s not even that new at the point in 2025 we three are talking about static site generators, right? But that’s how I use Movable Type, and that’s how Movable Type, in its early days when I first started using it. It eventually grew to - I think in I think clearly in response to WordPress - grew to have a - and again it sounds technical but in practice it actually had a fundamental difference where the original version of Movetable Type which is basically how I’m using it. It’s a Perl programming language series of CGI scripts. ⁓ But it’s effectively, in modern parlance, a static site generator. I update or create a new post, and it emits files in the file system on my server that Apache serves. And I could delete Movable Type from my server and daringfireball.net would continue to function 100%.

Because nothing that the public reaches touches Movable Type. It is just the files that have been emitted that run. And that makes sense in my head as a way to create a website. And I understand and understood all along that the dynamic nature of WordPress out of the box where, if you change things, there’s nothing on the server. You know, everything is sort of cached and it’s just a different way. It’s just a different way of looking at it. And I understood how that sort of dynamic, if we change something, we don’t have to rebuild the whole site. We’ll just change it. And then everybody who hits these URLs will get the new thing makes more sense to people.

And then Six Apart, as you know, changed Movable Type or added a whole PHP replication of, know, there were effectively towards the end of Six Apart as a company, as an independent endeavor. You could get Movable Type in two different ways. The Perl version that ran as a static site generator through CGI scripts or the PHP version of the same thing accessing the same database.

That was like WordPress, dynamic. Every time you hit it, you get the current update of everything.

Luke:
Yeah.

John:
I get that, but it just fits the way my view of how to publish on the web. But the thing that gets me is that all of the things that call themselves static site generators now, at least all the ones I’m familiar with, they all work on the command line and they’re on your computer and then you sync them to a server through Git or whatever and you do like this publishing thing, you have like this, you know, publish acts. Yeah, there’s a whole workflow. Whereas the way Movable Type worked is you just go through a CGI script and whatever you do is live on the server as you change it. See, there is no publishing workflow. It’s actually, the way Movable Type worked, if people understood it, would appeal to a lot more people than they think today. I’m not endorsing them to use Movable Type itself and download an old version of this, but I think the basic way that it works is sort of a lost art.

Jonathan:
Man, one thing that’s interesting too, and I want to hand it over to Luke in a moment to ask you about Markdown, but one thing that’s interesting about ⁓ everything that you said about static site generators, and I’ve been playing with Eleventy on a redo of my own personal site recently, WordPress is actually going more that direction in terms of the cutting edge to how do you, like we’re talking a lot within WordPress about composable and this idea of like having WordPress be a part of an overall stack and sort of what that looks like.

I’m curious, John, as an observer and outside of it, like what do you think about the WordPress ecosystem as a whole? It gets grown like crazy and there’s pros and cons of that, but like what’s your perspective on the ecosystem itself?

John:
My perspective has always been, I’ve always been a fan. It’s just never been from me. And it’s because the whole thing is so complex. And I have to admit that Movable Type itself, it’s internals, even though Perl is my natural programming language. And I know that dates me and isolates me off the mainstream today. Even though it’s all written in, yeah, you know, kind of am.

Luke:
You can be best mates with John Siracusa.

Yeah.

John:
Yeah, I kinda am best mates with John Siracusa. I find that Movable Type is written in a flavor of Perl that is very odd to me. It is to me non-idiomatic, but the APIs they published are very idiomatic to me. like in terms of actually modifying parts of the CMS or the CMS files itself.

I’ve looked at them for various reasons at various times. And I’m like, this is literally looks like Greek to me. Ben Trott, who wrote most of it wrote his Perl in a way that to me is obfuscated, but they had these API hooks for things like they call text filters, which is, hey, the body of a blog post could go through a text filter before it gets emitted to the static file. And that’s where Markdown hits.

The API for that was super easy. You know, like, this is exactly what I think it should be. I think WordPress overall, I think the reason for its decades long success is that overall, it’s way more friendly to, hey, if you want to look at the source code and you want to hook into this at a certain level and you want to see the way it works is way more open and friendly to that.

And it’s not for me, but I’ve always, I’ve never been surprised by the success and continuing success of WordPress for that reason. That it’s like, you can kind of see how it works. And yes, it has a bunch of historical cruft in some ways, but it’s like, man, it does kind of do everything you want.

And when you hear seemingly preposterous numbers about what percentage of the web runs through WordPress. It doesn’t seem preposterous to me because it seems to me like, yeah, but basically it offers so many things you want in what you want to do to create a custom website. And in a language that is approachable and understood by so many people, PHP, and with these hooks for things like themes and it’s like, here’s the definition of a theme and how you package it and stuff like that that have always been very developer friendly and very just the nature of the open web. Like, hey, we’re going to write really good documentation for how you make a theme and stuff like that.

Luke:
All right, so you touched on Markdown. Wow. You know, when you’re 100 years from now, when people are reading or having AI summarize the Wikipedia article for John Gruber, they’re gonna see that he was an influential journalist on Apple, but right alongside that is gonna be the inventor of Markdown. It’s had such a huge impact. Did you realize at the time when you were putting it together?

John:
I don’t know that that’s going to happen. I honestly think that 100 years from now it might be forgotten who created Markdown. And I’m not complaining, but it seems like and it’s a tiny little thing. And it annoys me, probably annoys nobody else. But in the last, would say three or four years, I’ve noticed more and more that a lot of places where they’re like, it’s a brand new thing and you can use Markdown.

They don’t uppercase it. It’s just a lowercase markdown. Plain, the way you would say, you can just enter plain text and you wouldn’t capitalize plain text. They say you can just type it in “markdown” and they enter, they write the word in lowercase.

Luke:
Right.

Jonathan:
Interesting. It’s becoming.. it’s changing its way in the vernacular. Yeah.

John:
I don’t know what.. it’s like a generic thing and people think it’s always been there. I am very proud of it. And I did create it and invent it and, you know, I mean, I’ll take all that.

Jonathan:
Ha.

Luke:
But I’m curious about the genesis, you know, like, is this like a, is this like a weekend project that you’re like, “wouldn’t it be cool if…”, or is it a long term?

John:
No, well, hmm.

So basically the timeline - and, again, I don’t want to be a downer, and there’s this whole sort of sidetrack thing where it’s like, that actually Aaron Schwartz was the co-creator of Markdown, which is not true. But he was the one beta tester of Markdown who got it right from the start and was the one who gave me the best and most feedback. He was effectively, you know, boiled down to me making it, thinking I’ve got something here. And Aaron being the beta tester who was like, “Yeah, you’ve got something here. Keep going. You know, you’re almost done.” And then it’s this whole tragedy unrelated to Markdown where, you know, he got caught up in this whole thing with the federal government about blah, blah, blah. And he killed himself. He’s fucking dead. You know, and it’s a tragedy. And I love the guy. And I think the world is such a worst place. And what am I going to say when there’s people who are like, hey, Markdown was a co-creation of Gruber and Aaron Swartz. And it’s like, I don’t want to.

Jonathan:
You’re like, what? Wait a minute. Yeah, no, you don’t want to be an ass, right?

Luke:
Ha ha.

John:
Yeah. And I’m like, yeah, it was actually me. But but it was me. And if he were still around, he would I swear to God, I know that he would be like, yeah, it was him. He just wanted to sing the praises of it when it came out. And I’ve got all the emails, but I don’t want to look at them even all these years later, because I don’t like looking at emails from a friend who’s dead.

But one of these days I have to do it because it’s like, Jesus, enough years have gone by. But the basic idea was the first year or so that I wrote Daring Fireball, 2002 to 2003, Movable Type had two built in options for what they called text filtering. Just raw HTML, I forget what they called it, but it was effectively whatever you put in in terms of per character would be exactly what got filled in for the body tag in a post, you know, and I think whatever CMS you use, you understand what I mean, you know, that there’s there’s like a tag you put in your template for the body of a post. And here it goes. And if you typed and open angle bracket and blah, blah, blah, and close angle bracket, that’s exactly what went into the tag.

Luke:
Yeah, yeah. It would be escaped in the output?

John:
No, there would be no escaping, right? That was, you know, was like you were responsible for all the escaping. That was one of the options. And then they had another one called… probably still there probably. I’m sure it’s still there, but it was like, ⁓ basically it just was like added paragraph tags, p tags to blank lines, you know, that was it. And those were your, yeah, those were your two options. There was, there were, and there were no others.

And so I used the raw HTML version and I would write my posts in a text editor, BB edit, the longer they were, the longer I’d wait to mark them up in HTML, but then before publishing, would put all the HTML tags in, including paragraph tags, everything, and then paste it into movable type, and it was more or less using Movable Type as a way to just paste in the article part in an HTML document.

And… I don’t know. It didn’t take too long before I got the shits of that. And I was like, this is a pain in the ass. And where it really became a pain in the ass was when I realized how much of blogging was fixing typos, adding things, you know, like the initial writing. I wouldn’t have to have it in fully marked up HTML. I would have it in something that looked a lot like Markdown.

But then once it was fully marked up, then it became more and more of a pain in the ass to go back and figure out how to fix it. Spelling mistake or, yeah, the italics runs too long here or whatever. And Dean Allen, who at the time wrote, again, who sadly is dead now, but wrote the great website Textism and was the the creator of rival to WordPress, Textile. ⁓ Or no, what was the name of the CMS? Wasn’t Textile? Textile was the rival to Markdown. ⁓ Well, whatever it was, - Text Pattern.

But he had Textile, which was sort of a proto Markdown, but a little bit more. Now, anybody listening can just go Google Textile text formatting syntax and you’ll see what I mean. But it was a little bit more like writing a man page where you’d have like equals H1 before a header.

And it was good. And then somebody came out with a plugin for Movable Type where you could use Textile in Movable Type very quickly. And I never used that, but I thought about it. But I don’t really want to write in that either. But I knew Dean and Textism, his blog, had started a bit before Daring Fireball, but he was very encouraging to me and wrote me some very nice emails, you know, when I got started about my writing. And so I knew him and I started sending him feedback on Textile as to how I thought it could change. And he was he just wrote me an email the one at one point. It was like, this is great feedback, but it’s really sort of a different thing. You should just make a thing that does this.

Luke:
Cool.

Jonathan:

That’s awesome.

John:
And I was like, ⁓ shit, you’re right. And then I could free myself of all this other stuff about Textile that I didn’t like either, but was fundamentally like, can’t really complain about that because that’s sort of fundamental. I was like, yeah, I could do that.

And just sort of looked around and I did this survey of all these things that are vaguely like Markdown, you know, that are just formats for like, how do you, you know, say this is italic, this is a header, this is a link.

And I stole..

Jonathan:
Appropriated, appropriated.

John:

..from everything I could steal from and yeah and including from Aaron Schwartz his thing which was called it’s very little known now but if you Google Aaron Schwartz ATX I forget even what ATX stands for but it was a it was like Markdown but it only had like three or four features and I stole a couple features from it. And so I knew Aaron, and I knew Aaron otherwise, and I was like, I bet Aaron will like this because this is like ATX but does more, covers more things.

And I made it as a Movable Type plugin, the file itself could also work as a standalone command line script, which is how Aaron was using it, because he wasn’t using Movable Type.

And I started writing at about a year. So I started Daring Fireball 2002, started writing Markdown and at the end of 2003 and started, you know, had the beta and pre beta versions running on my server. So for like three or four months at the end of 2003 into early 2004, I was writing during Fireball using Markdown before I had announced it.

And every time I’d make a change, it was really just me and Aaron. Me as the creator and the person creating it, and Aaron as my one beta tester who really believed in it. so I wasn’t afraid to make breaking changes, but I would make these breaking changes and I’d have to go back and edit like the last six posts in Daring Fireball to change some of the syntax because I changed the rules for how this character worked or whatever.

But by early 2004, I was like, I think this is really something. And now I feel like this is how I want to write for the Web. This really feels natural. And Aaron was like, yeah, this is it. This is it. I’m never going to write for the Web in any other way. You’ve got it. You should announce this. You know, don’t stop shitting around. Put this out there. Yeah. And then I did. And, you know, some people took it up.

Luke:
Mm. And he was right.

John:
But it was so such a slow uptake for a couple of years where I was I wasn’t depressed about it because I wasn’t trying to make money or anything from it really. But it really the first few years after I announced Markdown, it really didn’t take off. And I was like, I don’t get it. And people were still announcing new things that use Textile. And I was like, why?

Luke:
Mm.

Jonathan:
That’s interesting.

John:
This is my thing, it’s so much better than textile. I know it is. I know. You know, no offense to Dean, but I know that it’s better. This is better. And then it started to take off a couple of years later. I was like, finally. But I didn’t change anything. It just famously, you know, like I wasn’t fucking around with it. I was like, this is what Markdown officially is. If you want to make like a slightly different version, go ahead.

But this is Markdown. But then three, four years later, it started getting somewhat popular. And then five, six, seven years later, it’s like, hey, it’s kind of popular. And then all of a sudden, like 10, 11, 12 years later, it’s like, hey, wait a second. This is too popular. You’re using Markdown in ways that are inappropriate. Typical users shouldn’t be exposed to this. You should give them a WYSIWYG interface, not this.

Jonathan:
What, you don’t think John, that we should be teaching people how to make tables in Markdown?

John:
No, I do not. I really don’t.

I think it’s become too popular, which I guess is a good problem to have. But I really do think that it’s more popular than it deserves to be at this point.

Jonathan:
That was where it crossed the line for me. I was editing some GitHub documentation and I’m like, creating a table in Markdown is not my favorite thing. It’s doable, but it felt like too much.

John:
No. Well, and my official 1.0 Markdown doesn’t have tables. And I worked with Michel Fortin, the creator of PHP Markdown, on the original spec for tables in Markdown. So I had a hand in it.

One of these days. You know, again, it’s sort of like the mobile optimized version of Daring Fireball. One of these days, there will be a Markdown 1.1 that I release that includes the table syntax. But part of the reason that I didn’t include tables was it all falls apart so easily, you know, with table complexity.

A I kind of like the things that are in my Markdown, the official 1.0 markdown on Daring Fireball. Everything is like “if this is all you need, it’s perfect.”

And that that was the thing with tables. It’s like tables are a real thing. I include tables in articles all the time. I get it. But it’s like if they’re not perfect and if they fall apart easily, I don’t know if they should be. And that was the sort of if I’m very, very selfish about what goes into official Markdown and only put in the few things that can be expressed perfectly.

It’s a very - it’s not a spec. I know that’s what so many technical nerds, you know, that there’s no specification and that there’s all sorts of ambiguities based on the definition of it. But if you just look at the human readable version of it, it’s like, well, there’s headers, there’s italics, there’s bold, there’s links, there’s images and that’s basically it. And you can kind of do all that and all of that works perfectly.

Luke:
So, do you like GitHub’s checklists? That’s a nice one too.

Jonathan:
The checklist is nice.

John:
yeah, I do. And again, you know, that’s been a source of it. I don’t think of it as controversial at all. I actually think of Markdown less as a spec or a single thing and more of an idea. And GitHub flavored Markdown is to me my second favorite Markdown in existence after mine. And the fact that there are flavors of Markdown, I think is a success story, not a failure.

There’s a technical nerd who imagines that there could be one true Markdown spec that makes everybody happy. And I’m telling you, I guarantee you there is not. There is no feasible way to make one flavor of Markdown for everybody because the contexts are so different. GitHub’s Markdown is amazing. It’s fantastic. And I think that the hands-off attitude that I’ve taken to this has encouraged the blossoming of Markdown’s use. GitHub’s Markdown is example A, B, and C in that argument. It’s truly great.

Jonathan:
I think there’s a good parallel to that all the way to the back of the original start of this conversation in reference to Substack. There’s something about having our own individual flavors when it comes to building on the web, right? And where it’s like, hey, yours is gonna be different than mine. That’s gonna be different from Luke’s. And there are things though, like Markdown to me is a great example of something that actually makes the creating process ⁓ easier and more enjoyable, right? When I’m trying to format something, I don’t have to write HTML if I don’t really want to and I can incorporate it.

John:
Yeah.

Jonathan:
My last question for you, John, is when you think about the WordPress ecosystem, the project specifically, is there anything that you’d like to see more of from WordPress when you think of it within this context of encouraging more people to create their own things on the web?

John:
I don’t know how to answer that exactly because I, and I wish..

Jonathan:
Let me couch it this way. It’s because of WordPress’s influence and the momentum that it has, right? Like it has..

John:
But I wish that I did, because I feel it’s like when you know that there’s an answer, you know, here and you know here and you know there’s an answer in between. But I can’t tell you what it is. But there is something that tells me in my gut that Substack in particular should not have had the room to grow that it has, because WordPress should have occupied that space and didn’t.

And I don’t know what that is, though, in terms of practicality, like exactly what whether it’s Automattic as a company or WordPress dot org as an open source thing. But somewhere what WordPress aims to achieve and fill in, Substack filled that gap and in a way that I think if you have me on the show again in 10 years, I think we’re all going to say, yeah, I remember when everybody was on fucking Substack and that blew up. You know, I don’t do not think Substack is here to stay. I really don’t. I think WordPress will outlive all of us. And, you know.

Luke:
You know, we were talking about about exodus before. WordPress isn’t immune from that either though. You know, I’m sure you must’ve heard of some of the controversies that are sort of wrapping up really over the last year.

John:
I don’t follow it closely and I know Matt Mullenweg personally, I would go so far, even though I haven’t seen him in a while, I would go so far as to describe him as a friend. So I’m not an unbiased observer. And so I’ve observed this and I’ve been more than anything, though, confused by it. It just doesn’t seem right. It just sort of feels off.

Like, I can’t tell you exactly why. And I think probably most people listening to your podcast, listening to us talk will sort of feel the same way where it’s like, I don’t even know exactly what it is about this whole conflict that rubs me the wrong way. But it rubs me the wrong way in terms of it should never have existed. And I’m not even absolving Matt from it. Like, I do think that he’s responsible for at least part of it.

You know, that it could have been avoidable. But there’s something about it that it’s like this whole thing just isn’t right. You know, I don’t know how to say that. But, you know, and again, and I’m a little biased because I’m his friend, but I would love to take him aside and be like, what the fuck is really going on? You know?

Luke:
A lot of us would, yeah, I think that default position of grace and saying something’s not quite right. And not immediately making Matt out to be the villain is a good one.

John:
Yeah, but there’s something.. there is the spirit of WordPress, it’s still there. And again, I’m not just saying it because I’m on your podcast, but it’s still there where it is. Hey, you don’t have to give us money, you know, to build a great website using our technology. Right. Like that’s the whole idea in that we can thrive and build a great business, a great, big, thriving business based on our technology while still letting people use our code in a truly open source way, with no relation to us financially whatsoever.

I think that’s still there, but it has a bad smell to it that it never had before. Like a little bit of a bad smell, like some of the stuff in your fridge needs to be thrown out. Not that the whole, know, you need a new refrigerator, but I don’t know - there’s a couple items in there that that got to go.

Luke:
Yeah. I like that.

Jonathan:
That’s a good take, John. I think that there’s something about that too. And you got me thinking more about Substack as well. So it’s gonna be interesting to look back and reflect on this because there, to me, like there’s a momentum to WordPress that you just can’t count out. And the question is, how do we guide that in a way that’s helpful to the bigger long term goals?

John:
Right. I honestly think that the whole WP Engine thing though is a distraction. I’m not saying it’s not real and people shouldn’t be concerned, but I think it’s a distraction from the fact that the whole Substack thing kind of creeped up on the WordPress community in a way that if WordPress were really killing it, not just Automattic as a company, but the whole community, Substack shouldn’t have existed. I really do believe that.

Luke:
Mmm.

Jonathan:
That’s got me thinking. That’s going to be worth some additional thought and follow up.

John:
And I do think there’s a thing in there where, again, I don’t think we should let this go, where Substack launching as a newsletter platform really did kind of creep up on people in terms of, hey, that shit that you read in your web browser is annoying as hell because it’s popping up things like, “Hey, subscribe to this, subscribe to that.” And when you get an email, you just, space bar, space bar, space bar, read to the bottom and you’re done.

And Substack kind of creeped up on that in terms of, hey, we’re not gonna go through your browser, we’re gonna go through your email client. And when we go through your email client, we’re not gonna annoy you at all because once the email hits your inbox, you just space bar, space bar, space bar to the bottom and you read the whole thing and you’re done. And people really like that because you just read and you’re not annoyed.

And it’s not WordPress’s fault that people build WordPress sites that have annoying features. It’s not their fault, but it’s true that a lot of WordPress sites are much more annoying to read than Substack sites.

Jonathan:
Yeah, there’s something there and part of the challenge is when you’re not gonna force people.. Like you have the freedom to do whatever you want and today, in the current state, there’s a lot of poor practices that are being implemented.

John:
Let me apologize to you guys. Every single podcast I’ve ever been on in my entire life has gone long.

Jonathan:
Well, it’s been our pleasure.

Luke:
Ha

John:
Maybe I talk slow. I think slow. I am very sorry. I know this went long. You don’t have to apologize to me. I think it’s my fault.

Jonathan:
It’s been a lot of fun.

Luke:
John, we are both huge fans, so we’d be happy to sit here and talk to you all day, I’m sure.

Jonathan:
John, this has been a lot of fun. I’m looking forward to seeing where this evolves and look forward to a mobile optimized version of Daring Fireball within the next decade maybe.

John:
And a Markdown spec with tables, right?

Jonathan:
Exactly. John, thank you for joining us.

John:
Thank you guys for having me. I really enjoyed talking to you guys.

Transcript generated via Riverside and edited by Jonathan, who accepts responsibility for any mistakes.