Brent Simmons at WWDC: Gruber & Wiskus are Trying to Kill Me!

Each year at WWDC, TMO interviews a few Apple developers who want to tell their story. The result is usually a number of serious insights into the state of mind of the developer community. In our third interview, Dave Hamilton chats with Brent Simmons, currently of Q Branch and Vesper fame.


Dave Hamilton: Brent, you’ve been developing software for a long time, but the Mac was not the first platform you wrote for, right?

Brent Simmons: The Apple II+ was my first platform as a kid. My parents were programmers, and they taught me how to use BASIC on an Apple II+. But, as a professional, the Mac was my first platform.

TMO: So, coming to the Mac was part of a natural evolution coming from the Apple II, like the rest of us?

BS: Exactly. Yeah. I’ve always been an Apple guy. But I did a little Windows programming in the late 90s, just a little. Just enough to hate it.

TMO: [Laughs] Good. Gave you a little perspective. Let’s talk about this new app that you have. Then we’ll move on to some other things. Last week, you just released your latest app called, Vesper [reviewed by TMO]. You did Vesper with a design team that’s been talked about quite a bit, a company called Q Branch, you and Dave Wiskus and John Gruber. But the concept of working together, from what we’ve heard, was your idea…

BS: Yes. Initially, I was looking for something to do as a side project. I wasn’t terribly happy with my job at that point. But then I realized that I couldn’t really do it as a side project. And so I quit my job, and made this my full-time job instead. Which was very much the best decision. I’m so happy about it.

But initially, I thought it would be really cool to work with two of my friends who are very talented and share a lot of the same sensibilities that I do. I thought it would make a great team. As it has been wonderful.

Of course, they’re trying to kill me.

TMO: As designers should!

BS: Right. Their job is to find work for me. Boy, they’re great at their job! But, I wouldn’t trade a second of it. It’s so much fun.

TMO: Is this your first iOS app? Or was it GlassBoard?

BS: My very first one was NetNewsWire for iOS. That was on the App Store, day one. And then I did NetNewsWire for iPad which shipped with the initial iPad apps as well.

TMO: Ok, I had my timing off. I thought you had passed it off to Black Pixel, but that was later.

BS: I also wrote an app for All Things D, Walt Mossberg’s thing. That’s not still on the App Store. The one they have up now is not the one I did. Also, I developed a framework called taplinks, which makes it easy to put together news apps. That’s now owned Joe Pezzillo [also interviewed] and Dan Burcaw.

TMO: Okay, so your entire career has been developing apps, having great success, bringing them to maturity, and then passing them off as you move on to that which interests you next. Is that a fair assessment?

BS: That’s fair. But I worked on NetNewsWire for nine years. But MarsEdit was mine, two years? before I passed it off to Daniel [Jalkut]. And Daniel has done wonderfully with it. So, some things I stick with longer than others.

When your career is long enough, I think it’s kind of inevitable. After awhile, you just have to do something else. Or maybe the need for that app doesn’t exist anymore. Or maybe the app doesn’t interest you the same way it used to. And so you gotta figure out what to do next.

My plan for the future is to sell everything to Marco [Arment], and then have Marco sell it six months later. He wouldn’t even have to write any code, it’s just pure “app laundering.” [Brent is joking here. See, this blog item.]

TMO: App Laundering! There’s a business in that! Just collect the money! That’s it. In all seriousness, though, development is what you love. But are you fully satisfied by Apple’s support of their platforms? iOS and OS X?

BS: Well, there's always more things I would like. But, yeah, I love writing for these platforms. I have no interest in doing something else. Well, the most I might do is a bit of web programming ... but that would be in the service of Mac and iPhone and iPad apps.

TMO: Have you done anything with iCloud? Any frustrations there?

BS: As far as iCloud syncing, I’ve mainly listened to my friends complain about it. At length. Insane length. I haven’t written any iCloud syncing code myself. I know enough to know that it’s just not going to do the job. Which is a shame.

TMO: It seems like Core Data is where most of the problems are, and everything else works ... kinda…

BS: Yeah, but even still, you know, the document syncing didn’t work well enough for Omni Presence, for them to have something really reliable. It’s really those two things, Core Data and Document Syncing. Which is, like, practically everything!

TMO: Has the experience with Apple’s App Store been most positive with you?

BS: I wish the app reviews [approvals] were faster, but that’s about it. However, if something goes wrong, it can be scary if they don’t give you any information. Sometimes, I think of the book, The Trial by Franz Kafka. Where Josef K. is accused by somebody of something, and he spends the entire book trying to figure out what it is. Nobody will tell him. He’s trying to think of what it could be in his mind.

And that’s kind of what happens when you’re waiting for a review. They say: “It’s going to take additional time.” And I’m thinking, “What!? Could it be this? Or this?” And you get no information. It’s a perfect black hole of bureaucracy. But it’s not quite as bad as in Kafka’s novel -- it just reminds me of it.

TMO: Have you ever had any real roadblocks with that or has it sort of worked out?

BS: Things have worked out... The worst case was NetNewsWire lite for Macintosh. That took some extra time because of an Apple bug, but they wouldn’t let it through until they had a workaround for me to use. But it delayed it by three weeks getting in the Mac App Store. That was maddening, insane. Otherwise the process has been good. It works.

TMO: With Vesper, it’s a version 1.0 app. Out for not even a week. Mostly positive reviews. But some people are asking for syncing and this and that. Mostly syncing. Any plans that you want to talk about? Or are of you a singular focus on this? [For example] It is what it is, so enjoy it.

BS: It is a 1.0 app, so it’s a screaming baby. It doesn’t have all the things it’s going to have. I’m not going to comment on specific plans, but I find it very interesting that what people ask for, they say they want syncing, but implicit in that is that they want an iPad version, a Mac version, a web version. What they’re asking for is not syncing but other versions that sync. And so ... we wrote an iPhone app. And your iPhone’s probably in your pocket or your bag or something, and when you need that data, it’s there.

I think it would be an amazingly strange move if we added syncing and everyone said, “But, I only have one iPhone!”

TMO: Anything about today’s announcements that excite you? What do you think of the new iOS layout, especially after having just shipped an iOS app.

BS: It looks like Apple is looking at the same trends in UI design that we’re looking at. And some other people, like Loren Brichter and Icon Factory. And so there’s a fair amount of similarity from what we saw today and whet we’ve seen from independent developers. I love that. I love the new look. I can’t wait to actually hold it in my hand. I think it’s definitely the right way to go. I am so pleased.

Five years from now, maybe it’ll be something else entirely. Who knows?

TMO: I hope it is! Five years ago, we loved iOS as it exists today. For the most part, we loved that up until the last six months or so. But now, we’re ready to move on. It needed to be done. It’s an evolution. If Apple had released, five years ago, what they released today, the OS wouldn’t have worked for people.

BS: I think there’s something to this new style, working best on Retina displays. You really needed gradients and fancy stuff on the old displays just to make them look okay. I think that’s one reason why iOS 7 looks the way it does now. Type is so crisp and beautiful on a Retina display. On the old iPhones, not so much.

TMO: Right. I hadn’t thought about that. We don’t need those edges around text anymore. Cool. Anything else stewing?

BS: Not much. Except, I love WWDC. It’s like Christmas. It’s a fun part of the year. I get to see all my old friends. Make new friends. I love the energy. I come away inspired. I want to go home and get back to work. I see all these people making cool stuff, and I think, I want to make cool stuff, too.

TMO: I know you don't have a ticket for WWDC this year. Is this the first time?

BS: Yeah, this is the first time I've gone ticketless. And odds are I probably won't bother to get a ticket in the future. Just because, hey, I'm 45. I know a lot of stuff. I know a lot of people at Apple. Someone newer and younger than me can use that ticket. Know what I mean?

TMO: Yep.

BS: And then I don't feel guilty if I sleep in!


TMO: Cool. Well, very good. Thanks for taking the time. We appreciate it!