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Full transcript: Daring Fireball founder John Gruber on Recode Media

“One of my goals is to be right, all the time. Meaning, correct. And that’s impossible.”

Amelia Krales for Recode

On a recent episode of Recode Media with Peter Kafka, we heard from star Apple blogger and Daring Fireball founder John Gruber.

You can read some of the highlights from his interview with Peter at that link, or listen to it in the audio player above. Below, we’ve posted a lightly edited complete transcript of their conversation.

If you like this, be sure to subscribe to Recode Media on iTunes, Google Play Music, TuneIn and Stitcher.

Transcript by Maya Goldberg-Safir.

Peter Kafka: I think most people know who you are, but in case they don’t, you are one of the foremost Apple experts. You were a pioneer in both blogging and podcasting. Very happy to have you. Welcome, John Gruber.

John Gruber: Thank you, happy to be here.

I didnt really think we were gonna talk about dongles when I booked you weeks ago, months ago, but here we are.

We're talking now about the rumor that the next iPhone will no longer have a headphone jack?


It's weird, the cycle of these rumors with Apple stuff, because that first came out via sketchy Asian supply chain sources months ago —

Right. And then it was initial, "What's Apple thinking?"

Right, and we went through it with the whole thing — "we" being the people who obsessively comment on Apple stuff on a daily basis. And then what happened last week was, The Wall Street Journal reported the same thing. Every single thing Daisuke Wakabayashi reported was all previously rumored. But once the Journal puts their stamp on it, it becomes a big deal.

It’s a fun thing to talk about. It’s also sort of instructive about what you do, and how press works. So the story, again, is that Apple's gonna do away with the standard headphone jack, and replace it with the lightning port?

Nobody knows! That's part of it, all that people know is that the headphone jack is going away. What their proposed solution is for how you're going to listen to audio from your phone, we don’t know yet. Is it gonna be lightning? Is it gonna be all Bluetooth? We don’t know yet.

Right. So we know the old port is going away. This then triggers a bunch of standard reblogging of the Journal. And then there are several angry posts. One of them is written by my colleague at The Verge, Nilay [Patel], very angry! It’s a great rant! Then you respond to the ranters, saying, "I think I know what Apple's doing, although I don’t really know what they're doing." This is both a familiar cycle if you've watched Apple technology and I think it's less frequent than it used to be. I think this stuff used to happen a lot more often, and now maybe there's less of it because there's less surprise coming. Does that sound right?

Yeah, maybe. Something that maybe separates me from other people that follow this stuff is that, I think I'm more calm. I don’t overreact to this stuff. We’ve been through this so many times before. One of the examples I cited was, in 1998, the original iMac didn’t have a floppy drive. And in hindsight, everybody's like, "Well, floppys were so slow and small and you couldn't put anything on them." Today, when you cite that example, everyone looks back and says, "Well, of course they got rid of the floppy drive, they were stupid at the time!" But at the time, people used them for — the colloquial term is a sneakernet, the way we use thumb drives now. But thumb drives didn’t exist then, because USB was like a brand new thing and PCs didn’t have USB. So if you just had like a PC and a Mac in the same building and you just wanted to get an Excel spreadsheet from one to the other, a lot of people would just use a floppy drive.

So there was a period where Apple getting rid of floppy drives was a big deal to a relatively small number of people, and then at some point, I guess really with the iPhone, Apple had become a giant, giant brand, and this stuff seems like it became much more important to more people. It seems like that's waned a little bit. Does that sound right to you?

Yeah, I think so, maybe. Another example would be when they got rid of the CD drive and DVD drive in the laptops — remember? People would say, "Well how in the world am I gonna watch a movie on an airplane?!"

It worked out.

Yeah, it'll work out.

So as someone who participates in this scrum — you're the calmer voice and you can talk about sort of where your role is — when you see people getting really angry about getting rid of the port, do you believe these are genuine feelings they have, or do you think this is sort of theater and this is part of a cycle, that no one is taking that seriously?

I think its a little bit of column A and a little bit of column B. Nilay isn't sensationalizing his opinion, but he’s not downplaying it, either.

Yeah, Nilay’s good at spectacle, I think he would agree with that term. I’m probably crimping that from him, actually.

And he's a good example of someone who does it right. And he's very, very good at it. Others definitely overreact a little bit and especially on the finance side of it. Like when Apple's stock moves up or down a little bit, some of the people who write about these... I have a collection of bookmarks from people who, ostensibly seriously, are calling for the Apple board to fire Tim Cook. Which is crazy!

Right. You can go deep in press criticism at some point, but I think maybe there are different motives? I think if you're in the financial press or if you're a financial analyst, you can either say, "Well, could be this, could be that, not really sure where it's gonna end up," sort of shrug, or you can say, as my old boss Henry Blodget did, "Amazon's going to 400!"


My goal is to identify, if I've made a mistake or I'm wrong about some sort of aspect of what I speculate about, to correct it as soon as I can.

And if you're wrong, you're wrong, and you get a little egg in your face, and you might tease them in a blog post, but really, you don’t really get penalized for being wrong. If you're right, it makes your career. And maybe for both analysts and bloggers, it works both ways. You get rewarded for taking an extreme stance. You generally don’t, I think, now.


You're sort of like "Mm.. eh."

Yeah. Henry Blodget's a great example. I remember the one, he had a headline, probably like 5 years ago, something about "iPhone dead in the water."

Yeah, it’s a very Henry title.

Very Henry. You know, that would drive me nuts because one of my goals is to be right, all the time. Meaning, correct. And that's impossible. Everybody, you know, makes mistakes. And so my goal is to identify, if I've made a mistake or I'm wrong about some sort of aspect of what I speculate about, to correct it as soon as I can. Not to sit there and try to make up phony reasons to say why I wasn't wrong in the first place. But something like that, having a headline like that in my archive, would drive me nuts.

Do you ever lean out and say, "This is what Apple's gonna do, I believe this," where it hasn't been disclosed and you're gonna break news? Sometimes you'll sort of hint...

Sometimes I'll drop hints. I do it less and less as the years go on. ‘Cause I just don’t think it’s productive.

Let’s talk a little bit about what it is that you do, and what you do day-to-day and how you got there. Let's start present tense. So day-to-day, you're writing, your site is Daring Fireball.


And you're producing one podcast, multiple podcasts?

Just one podcast.

One podcast, weekly... ish?

Weekly-ish. I think I've averaged about 40 episodes a year.

And that is your full-time job: Blogging, podcasting?

That is correct.

You run a giant empire staffed by how many people?

I have no employees.

Just you?

No, I don’t even have an assistant.

And I'm assuming there's a contractor here and there who helps you edit or something?

Yes. So the podcast, I have a guy I've been working with for a while named Caleb Sexton, who does the audio editing for it.

But you are literally a one-man media company?

That is correct.

Strangely, you're sort of under-appreciated in the publishing world. There was a period, I think when technology blogging was newer, and you were clearly the best Apple blogger, that was a big deal. There's a bunch of people who are now doing lots of different stuff. But I think there’s a lot of discussion, "Where's media going?" And I think one version of it is, "Maybe people will be their own content companies, and maybe they'll work with Facebook, and what would that look like?" And you're out there doing it. You are blogging, podcasting, that is how you make your living.

That is correct. I started this site in 2002. I've been full time since 2006? So there was about a four-year period there where I was doing it entirely on the side, and went from zero revenue to, "Okay, I think I can actually, maybe, go full time."

I could just tell at a very young age that these were the nicest computers.

What did you start out doing? You were a developer... ish?

I went to Drexel University, majored in computer science. Drexel has a great program, they call it co-op, but its like mandatory to graduate to do internships. I loved it because it helped me figure out very quickly that I didn’t really want to be a programmer.

It disabused you of that notion?

Right, I didnt like it! And I also was very active at the student newspaper, eventually became the editor in chief. That's where I learned graphic design, self-taught, and really enjoyed writing. So when I graduated in '96, I was just kinda lazy. I had the technical skills to build websites —

When that was still a relatively rarified thing.

Yeah, and so I just did a lot of freelance graphic design and web design.

There was a period where you could make a lot of money just building websites, ‘cause no one else knew how to do it..

Yeah and I wasn't ambitious enough to make a lot of money. I just made enough money to get by. And then in 2000, I went to work for a Mac software company called Barebones Software, that people make BBEdit.

And were you always a Mac guy, were you always an Apple guy?

Yeah, always a Mac guy. Always very into computers, especially Apple computers.

What was the thing about Apple that you appreciated, sort of prior to becoming a professional Apple observer?

I could just tell at a very young age that these were the nicest computers, that there's something very different. Put a Commodore, and a Texas Instruments ... at my elementary school, it was sort of like a hodgepodge. Instead of having any kind of system, individual teachers would somehow finagle their way to get a computer —

Someone had a Commodore PET.

Yeah, and so some of them were Texas Instruments and someone might have had a Commodore and then there were a couple of Apple IIes, and it was so clear to me that that was the thing.

So you go to work for this software company.

Yeah, I spent two years there and — I've told this story before but its kind of funny — I'm six years out of college. In the back of my head, what I really wanted to do was be a writer, of some sort. And I could see, like with Jason Kottke and a couple of others... Andy Baio’s web blog...

I was so unhappy! Because I felt like, "I wanna be a writer, but I'm not writing."

Kind of post- first internet boom. People are sort of blogging but not many people are doing it.

And I had a vague sense of, "I could do that." It didn’t seem like I could do it while I worked for Barebones, because what I wanted to do was be opinionated. And being inside of one particular company, it just didn’t seem like... It sounds funny because I think in today's world, that would be fine. But at that point it’s like, you can’t really be criticizing Apple while you work for...

No, and it also sounds like one of those things that someone might say is fine, and then once you start doing, they say, "No no no, it’s not actually good!"

Actually, now that I think about it, I really couldn't do what I do if I worked for another company. But one of their products was an email client, long since abandoned, but it was sort of like a companion to BBedit. I just did all sorts of stuff there, but one of the things was, I would help out with tech support and on the customer mailing lists, and a customer one time wanted to know: "Hey, can somebody help me write an Applescript that would go through my entire Sent Mail archive, and figure out how many words of email I've written? I'm just curious." And so I wrote it. And I was like, "That's interesting." And then I ran it on my own, and I realized that I had written, in the last two or three years, like 200,000 words. And I was like, "Well, that doesn't make any sense." And I checked, and I made sure it wasn't counting the quoted material from old emails. I had this vague ... I was so unhappy! Because I felt like, "I wanna be a writer, but I'm not writing."

But turns out you were.

Yeah! I was! It was just all going onto mailing lists and stuff like that. So 2002, I left Barebones and my now-wife and I, we were just living together, moved back to Philadelphia. And I’d just started doing freelance work again. And I still had a lot of contacts from before, but I started Daring Fireball in August of 2002.

So you start Daring Fireball, you're paying your bills by designing websites and your thought is, "I would aspire to make this a full time job one day."


And how does that happen? How does the finance part of that work?

The first thing I tried was like subscriptions? Not really subscriptions, I think I called them memberships. And a lot of people are doing pretty well with that right now.

I'm a writer first and a businessman second.

But at the time, this was probably, "No one's gonna pay for anything on the internet." The New York Times had tried it and gotten away from it -

Right, and I didn’t want to put my stuff behind a paywall, that was the problem. The problem is I'm a writer first and a businessman second. And my ego was such that I just couldn't bear to not have my stuff public. Like, so people could link to it. And so when I started, I had a poor man's paywall. The first two years I did the site, all I had were feature length columns, like articles. I'd do probably two or three a week.

Who were you writing for? Who do you imagine your audience was?

I've always said, my audience is just me. It’s somebody out there who's exactly like me, and just isn't writing Daring Fireball.

And "you" is someone who's mostly interested in Apple, and there's some things that are tertiary to it, but its very Apple-specific. That's the thing you are most interested in writing about.

Right. It’s just an imaginary version of me that's out there, and I just know that Daring Fireball is his favorite site.

Have you ever thought about, maybe I should ask my readers what they wanna hear about or maybe I should poll them or maybe I should do a survey, maybe I should figure out who's actually consuming me, turns out its not who I think it is at all.

No. Maybe I should, but I've never done that. So all I had were the feature-length articles at first. And then I added the brief ones. Most of what I do now is the links to other people's sites with my little two bits of commentary, but that wasn't there for the first two years! And what I started with the memberships was, I had those set so that they wouldn’t come [up]... 24 hours, they were only for people that had the magic URL.

The links to other people's stuff?

Yeah. And I sold t-shirts. Within two years, it turned into a very nice side project. But nowhere near enough to support a family.

So when did that kick in?

Uh... slowly but surely. So then from 2004 to 2006 I worked at a startup called Joyent and I was still writing Daring Fireball on the side, and I was just miserable! "This is what I wanna do all the time, and I've got all these other responsibilities." And so I thought, "You know, I think that I'm never gonna get to a full-time income until I'm doing it full time..."

"I've got to jump."

Yeah, "I've gotta jump." And we had enough saved up. Joyent paid pretty well, so we had enough.

And your wife or girlfriend, you tell her, "I'm gonna quit my job, that has a salary, and I'm gonna go do this thing which does not have any guaranteed income."

Right and the stupid part about that, I overthought it, and I probably should have done it sooner. It’s not like I was toiling in obscurity, I was making a name for myself in the industry I'm writing about. If it hadn't worked out, I wasn't making it harder for me to get a job in 2007. It only would have been the public embarrassment of admitting that it didn’t work out.

At least doing what we do, failure is not the worst thing. The worst thing that happens is, "That thing didn’t work, I'm going to go do a different thing. You know who I am, I'm going to build on that."


The whole industry went off the deep end at the very beginning of the web.

And so what is the mechanism that eventually turned this into a real business for you? Advertising, right?

Yes. And in particular a format, that I don’t know of anybody who tried it exactly like I do before, where it’s one weekly sponsorship. 52 a year. That's it.

Someone gets the privilege of attaching their name to your site.

Right. I'm also a member of The Deck network which is a very small sort of boutique advertising network, but that's a much smaller portion of the revenue to the exclusive sponsorships that I sell.

The perception of it is that you're one of the people who is interested in making money from advertising on the internet, but has very specific ideas about how that should work.


There's a lot of stuff that goes along with traditional web advertising. You say, "I don’t want any part of that. I'm only gonna do web advertising under these conditions."

Yeah, I've long been very opinionated about it. I really thought that the whole industry went off the deep end at the very beginning of the web, with the way that they went about advertising with pay-per-click and pop-up ads and CPM, charging CPM. It’s crazy! Because in the print world, there's a gating factor on CPM, which is that it’s super expensive to print anything because paper is expensive. There's absolutely no gating factor like that on the web. People don’t really do this anymore, but for years, they would break up articles into little, 250-word chunks and then you'd have to click to go to the next page.

Yeah, BuzzFeed goes us off that finally ‘cause they showed you could do scale, and stop doing slideshows. "We're just gonna give it to you in one giant chunk."

Right. It’s crazy but it’s all just obviously to inflate the number of pageviews. And so my thought was, "Let’s make something exclusive." In the print world, they've been long been very great at it. Like the back cover of a magazine: Super expensive, because you get the full color, you get the best printing, you're on the best paper and there's only one of them. So why not try to do something like that for the web, which would be like, one spot a week, you get to run a spot, you the advertiser write like a 100 words, it will go out on a Monday and then on Friday or Saturday at the end of the week, I'll write a thank-you post, in my own voice, thanking you and I'll hit all the, whatever talking points you want me to hit.

And so that works, that builds, I think your rate card — like $9000 is what you're charging now?

It fluctuates right now. But that’s where it’s been for a while.

And then you started doing podcasting on top of that, and again, same basic idea when it comes to advertising, "I'll do one or two sponsors." I think you're more amenable to sort of the cost per action model that a lot of us use, right — that you're gonna get rewarded if someone does something using your code?

No, I don’t think I've ever done that.

No? I just assumed you were.

No, I think everything is just paid up front.

You just pay you a flat fee, and you promote it. Let me talk about podcasting for a second because these things tie together. There was a New York Times article a couple months ago saying, ‘I'm not sure where advertising's gonna go with podcasting because there's really no way to track this stuff. The ad money is not gonna come until this gets resolved, and also, by the way it’s all bottlenecked up at Apple.’ And you, again, were one of the voices saying, ‘This is a dumb perspective. The idea of adding more targeting, adding more surveying, being able to figure out what people are listening to is, is bogus.’ And that your way, which is sort of a more pure version of that advertising is the way to go.

Yeah, and it’s just like with the web: Be careful what you measure. And if you set something up where there's tracking codes, and the podcast players start doing all sorts of stuff, people are just gonna game the system.

Don’t you wanna know if people are listening all the way through, what they're listening to, when they tune out, wouldn’t you want more data instead of less?

A little bit, but I think it works out in the long run, where obviously people are listening through because I'm getting emails from people talking about things we talked about at the end of the show.

And you do two-hour-plus podcasts.

Yeah, the episode length has gone up significantly over time. And that's part of the reason I feel like I can justify only doing 40 a year, is I feel like the number of hours of material I have is...

It’s a lot of bang for your buck.


But, again — partly devil's advocate but I think I believe this too, I think you would be interested in knowing, "Oh you know what? Turns out, most people tune out at one hour and a half, one hour fifteen minutes." I get that there are diehards going four hours into this but maybe I should just be more efficient?

I guess I wouldn’t say no if I could access that. But I just trust that it’s being listened to in the aggregate.

And podcasting in general — I was talking to Dan Frommer, who you had on recently — he thinks that podcasting is now the bigger business for you. Is that fair? Or accurate?

I'd have to check my taxes from last year. It's close to 50-50, though. Some of it is a little hard to separate, what should I count as the podcast and what should I count as the website, ‘cause I know that one of the things that the podcast sponsors really like is that I always post — a new episode goes to my website, and their links are there too. One time, I just like absentmindedly forgot to include them and I heard from — very nice! Wasn't a complaint, but, "Hey, are you still gonna post the text?" and I was like, "Oh, I guess that is important."

I think I know the answer to this but, do you ever feel like "Boy, this Apple-centric podcast I'm doing is great. Maybe I could do a second one about something else?" Like you're here to see the Phillies play the Yankees. Maybe you do a Phillies podcast or whatever. Do you wanna branch out? Do you wanna diversify?

Maybe. I think if I did right now, doing another podcast would be the way to go because I think it’s around 50-50 in terms of where the revenue is. But it’s absolutely growing. So I would guess that maybe for this calendar year, this might be the year when the podcast surpasses the website.

And so if you expanded, would it be another tech-themed thing? Would it be something entirely different?

I dont know. I haven’t given it enough... An idea hasn't popped into my head that really makes me think, "I should do that."

So this is not pressing for you. You're comfortable with the way your business works, you could keep doing this in perpetuity.

I think so. Yeah, I can't see it stopping.

It is an Apple-centric podcast. I was going to say, "What's your relationship with Apple like?" But its good, because you had Phil Schiller on and you've had Eddy Cue on. Have you always had a good relationship with the people who run Apple?

Its very strange. It was a very slow boil, where when I first started attending, like WWDC, which was like around 2006, I asked my friend Jason Snell, who was then an editor at MacWorld, if he could maybe put me in touch with someone in Apple PR so I could see about maybe getting a press pass for the keynote, so I wouldn't have to get in line with the regular people. And he did! And that was like the first time I really had an official contact with Apple PR. My contact was always more through actual engineers and designers and backchannel stuff.

Right you actually talked to people who worked there, you were reporting. Did you think of yourself as a reporter?

No, not really. I always thought of myself as more of a columnist, but maybe a columnist who does reporting.

So you're going out and there was a period where, it still continues to this day, where a story would get reported out, "I think Apple's gonna do X" and "Apple's gonna do Y." And we'd go to you and you would say, "This is true." Or "this is not true." Or you would have a way of signaling whether you thought it was true. And from afar, I always thought, you're just tied into Apple comms and they're sort of giving you the nod.

No. Especially in the olden days almost nothing came through Apple's official channels. Whatever stuff I had was stuff that I got through actual sources and stuff that maybe wasn't supposed to leave.

Actual reporting!


There was one that always struck me — it’s funny to remember now, but it was a big deal at the time — when Apple basically moved away from Flash.


And Steve Jobs had a memo, basically kicking Adobe in the teeth. And I recall, because it was a time that we were really parsing what you wrote very closely. And you were tweeting in advance of that memo going out, "Oh this is gonna be a big thing!" And it was a big thing. Again, it’s amazing to remember now, probably 2010. And I remember thinking, "There is no way that you know about the contents of a Steve Jobs memo unless Steve Jobs is telling you or his comms people or someone in that structure..." But you're saying that wasn't the case?

No, that was not the case, I can't remember where I got that from, but it definitely wasn't from Steve Jobs.

If you look back at the early years of the site — 2002, 2003, 2004 — I'm a lot more critical. And it was justified.

Again, it’s sort of astonishing, you were talking about Mark Gurman on this podcast with Dan Frommer. I mean, Mark Gurman is able to do this. You are able to do this. And then that's kinda it. There aren't people who are really well-sourced on Apple. Various reporters at the Journal and the Times over the years will get better at it, but then they get sort of cycled out and they do something else. You and Mark are sort of the ones with actual deep contacts within Apple, it’s a very rare thing.

Yeah, and maybe you with the media stuff.

Yeah, but it’s a different thing.

Yeah, it’s sort of a different Apple.

It’s a very different Apple. I mean, let's be frank, the reason I'm able to do that is because the media companies are not in Apple. Right? They're media companies.

Right. I mean, there have long been Apple rumor sites, and that's not what I wanted to write. You know, I wanted to be a columnist. But I've always had an interest in rumor sites and for a while, I thought, how could you do it and be right? And the secret, what I figured out was that, you're not gonna get much. And so therefore, you're not gonna have enough content pushing. That's why they publish so much garbage and it doesn't pan out.

And there's no penalty for it.

Yeah, you gotta feed the machine. Whereas, if I just wrote my regular column, but only drop little hints of things when I had them — I might go 6 months without dropping a little hint... I could do that, and they'd always pan out.

So, again, it’s not Apple feeding you stuff.


This is you out and getting your stuff. The other thing that always struck me was that you — not always, but usually — you had sort of agreed with whatever line Steve Jobs and Apple were pushing publicly. Not that you were doing work for them, but that you were an Apple enthusiast, you also liked the way they were running the company. If you were ever critical of Apple, it was in a very specific way and it was a big deal.

Yeah, and you know, it’s funny, if you look back at the early years of the site — 2002, 2003, 2004 — I'm a lot more critical. And it was justified. Because the early years, I mean I don’t know how long you've been using a Mac, but when Mac OS 10 first came out, it was really slow! And it really had a lot of issues. So there was more to criticize. And then they really hit a roll when the iPods became really popular, and when they switched the Macs to the Intel processors, and they got so much faster and cheaper. And then of course, the iPhone.

Did you ever find yourself sort of strongly disagreeing with something that Steve Jobs, in particular, was pushing?

In the early years, with Mac OS 10, and it’s some super nerdy stuff. Like on the classic Mac OS, we didn’t have to worry about file name extensions. You’d just name your file whatever the heck you wanted to, and when you double clicked it, the right thing would happen. And then all of a sudden in Mac OS 10, it felt like we took like this giant step backwards, where files have these cryptic little "dot txt" extensions.

Right, so these are the complaints that someone who's deeply in love with a product and a company has, right? Most people are literally unaware of what you're even talking about.


I try to pull out the "Let's go back and talk about Steve Jobs again" card as little as possible. But you have to. His personality is so imbued within the company.

Has being an Apple enthusiast, being a Mac enthusiast, being an iPhone enthusiast, has some of the ardor worn off over the years because this stuff is available to many more people? I was just somewhere where everyone had an iPhone. It was a hospital. Patients, doctors, everyone had an iPhone. It wasn't a mark of status or anything else, it’s just what people use. Does that diminish your interest in the product?

No. Not at all. It’s certainly fortuitous, though, for me. I mean, I was gonna write about Apple almost certainly, no matter what. And when I started doing Daring Fireball in 2002, it was such a smaller company and it was such, it was such a smaller audience of people who cared deeply about this. And I certainly didn’t have any inkling that the company would get as big as it has, and that you would see things like, you know, walking down the aisle of a train, and every single person is using an Apple device of some sort.

Right, it’s no longer a marker, right? You don’t have the indie band thing, where I like the band, and now they got too big, and they're playing stadiums, and now I need to move on?

Right, no! And I think I've done a good job of just being honest with myself and not doing that, not trying to be contrary just for the sake of being contrary.

‘Cause it strikes me that, in addition to the sort of the size of the company, and that they've become ubiquitous, that it is a less interesting company to follow and write about. It seems like there's less audience interest, and I associate it with Steve Jobs, and the fact that he's not there. And I think its hard again to remember, but I think if you go back and look at some of the footage, we took for granted that he was a charismatic figure. I mean, he really was a striking person, and there's no... There's kind of Elon Musk, and there's kind of Jeff Bezos, but they're not really the same thing at all. Do you feel that loss, as someone writing about the stuff?

Yeah, I definitely do. And I try to underplay, I try to pull out the "Let's go back and talk about Steve Jobs again" card as little as possible. But you have to. His personality is so imbued within the company.

Right, it’s literally a dead end to say, "Steve Jobs this." He’s not coming back.

Right. Very few comparisons, but Walt Disney is about as close as you can get.

The iPhone really is the culmination of everything the company stands for and has stood for since they founded it.

So when you're thinking about the future of Apple now, what's your take? Do you think it's up in the air, or do you think Steve Jobs has created enough, sort of groundwork, architecture, whatever metaphor you want that this thing is gonna continue being awesome and excellent and worth following?

I've said this before, that I do think that Apple itself, as an institution, is a very Apple-like product, and that it was under-appreciated while Steve Jobs was alive, just how good of a company he created. Structurally, in the way that its organized. And I think that it really is a place where, systematically, interesting new products come out every few years. And I think, I definitely think that the likelihood is very high that that will continue, but it’s so hard to predict more than a few years in the future. You know, it’s like everybody's talking about them making a car, which seems like, if everything goes perfectly and they hit every target they possibly can, maybe like 2020? Or something like that, with all the regulatory stuff they'd have to jump through. And then after that it’s like, you can’t even see past that. So I don’t know.

There was a cycle where they went iPod, iPhone, iPad, and I think we were all trained to think, "Every couple of years, they're gonna come out with a new thing that shifts boundaries and creates a new category, changes the way the world works." And I think the new conventional wisdom is, "Actually, they made one of those, it was the iPhone, and that we've become spoiled by, expecting that every new thing is going to sort of create a new industry and when the Apple watch only sells ‘x’ number of units, and doesn't change the world, we shouldn't look at that as a disappointment." It’s just sort of the way of the world.

Yeah, and I think in some of the ways, the iPhone really is the culmination of everything the company stands for and has stood for since they founded it in 1977 or whatever. It’s truly the most personal computer you can have, it’s with you all the time.

So if they don’t come out with a "new iPhone," is that disappointing to you?

Yes, but not because I expect it or feel like you know, that they would if Steve Jobs were around, just because it would be so exciting. It really was such an exciting thing to see and cover in 2007.

I'm looking at your watch. You are not wearing an Apple Watch. Is that a statement?

No, I do wear it, but it’s like 50-50, and a lot of times when I take a trip like this, like I'm on a two-day trip to New York, and to conserve battery life, I don’t.

Yeah, so do you think that if it were a better watch, a better product, it would be on your wrist all the time? Or it’s just a different thing?

Uh, it’s possible. I just don’t have great affection for it. I do wear it, and I like the fitness tracking stuff. The Watch OS 3 update that they announced earlier this month, really looks like it could make be lot more useful.

I don’t get it, I don’t get why more people aren’t doing this.

What do you do when you're not obsessing about Apple stuff?

I watch movies. I like to watch baseball. And that's about it. And just read, tons and tons and tons.

You've got a sort of monastic approach to this stuff. Your website is sort of very specifically sparse, there's no clutter on it. If you haven't listened to one of your podcasts, and you're listening to this, you should, because it has a very specific cadence. It’s sort of unlike everyone else's product. It seems like it’s very considered on your part.

I would like to think so.

Do you think other people can do what you're doing, create a one-person publishing business, whether its actually websites or podcasts or whatever?

I used to thinks so and the leg up that I had in the early years, and again in 2002, 2003, was my technical background, the fact that I knew how to build websites and publish websites. That was a huge thing, because the way that you’d get started blogging back then was that you would download a blogging package and configure it and then install it on a web host that you were renting.

This was before Blogger.

Before Blogger, before Tumblr.

And so in order to work, in order to write on the web you had to know how to use the web, you had to have some kind of programming, technical...

Right, and for the early years, I just assumed that the reason that there were so few of "us," meaning one-person publishing companies, was that it was the combination of having the writing talent and the technical talent to do it, but then once it became obvious that the technical hurdles were gone and you could just start a site with Blogger or Tumblr or something like that and just you know, click click, and you have a website, and people weren't doing it, I started really scratching my head. Like "I don’t get it, I don’t get why more people aren’t doing this." And I still don’t know why that is.

And ‘cause we're at a wave right now: "Well, maybe that will happen on Medium, maybe Medium will become the tool that people do that." It seems inevitable that Facebook is gonna support those people. Maybe it turns out that writing for a living or talking for a living — can't be that hard, ‘cause I'm doing it! — may be enough to support yourself is a very specific thing...

Yeah and maybe it’s a personality thing, too. There are times where I sort of... I don’t feel lonely, but I crave, or I get jealous of the camaraderie of a small team of people, like you know, to work with someone like Dan Frommer, who's a good guy. To have colleagues that you actually like.

So you are in a lonely Slack by yourself.

Yeah. But I think ultimately, though, my personality is such that maybe I'm particularly suited to working in the, as you said, monastic style that I do. I've never been a very good employee. I think I've left employers on good terms, like friendly, and like, "Yeah, we'd still love to go out and have a beer with you," but —

But this has come to an end for a reason, it’s a good time to move on.

Yeah, and the other thing is, I really hate asking for stuff, I hate to ask permission. And so like, the other thing was like, it was never my goal to parlay the success I had in Daring Fireball into a job at an existing media company. Never even shopped around. I mean, in the early years, sometimes people would send out inquiries to see if I was interested, but I never wanted to.

So, New York Times comes to you, Bloomberg comes to you like with Mark Gurman, Apple comes to you... Someone says, look, you're doing a great job, we want you to keep doing what you're doing, but come work for us. Does that appeal to you?

No, I don’t think so. Apple would be — I can’t see that they would do it, but there is a position that I wish Apple had. I don’t think I would do it now, because I have a good thing going. But I think Apple should have the equivalent to an ombudsman. The New York Times calls it a public editor.

Yeah, it would be great!

... Somebody who works at Apple and gets a blog on but has the independence to write whatever they want. I think it would be so good, and for things like controversial app rejections, have this person look into it and talk to people and figure out what the actual story is.

I mean the one big difference, right — In theory, the New York Times public editor has the ability and the right and the expectation that they can go up to whoever they want in the New York Times newsroom and ask them a question and then report what they say.


Apple is famously secretive about everything. Hard to imagine how it would work, but it would be really cool if it did -

Yeah, it would be really cool.

Have you floated this to Eddy Cue or Tim Cook before?

I don’t know who I’ve floated it to. More people you haven't heard of, though.

Yeah, and whats the reaction?

"That's an interesting idea." Which is something you hear from people at Apple all the time!

I think it’s cool that you're doing it on your own.

Yeah, and that's sort of why I feel like there's no need for it. Like I sort of serve that purpose on my own?

Good. John Gruber, thank you for your time, this has been great.

This has been a lot of fun.

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