A Conversation With the Creator of the iPad Magazine App, Letter to Jane

pimpmyridelogoSurprise (I know I am): This is a positive post about a “magazine app” for the iPad. The app was not developed by a gigantic media company, but was created by someone you’ve probably never heard of. In my opinion, he has provided a welcome alternative to a lot of the assumptions that have gone into the well-publicized apps you’ve likely heard about over the past few months. This is a very long post (at around 5,700 words, perhaps the longest post ever on this blog) and most of it is very positive, but I thought I should catch up those who may not have been following my rants on this topic.

My earlier posts about early “magazine apps” being launched by major media companies have suggested they were too influenced by 1980s CD-ROM design, and not influenced enough by how people are actually using iPads to, uh, well, read — something I have typically associated with the magazine medium. I have observed that the design and development considerations driving these big-media apps are hell-bent on loading in as much additional media (or, as I call it, “bells and whistles”) as possible to justify asking people to pay more for a bloated CD-ROMish iPad app than they are already paying to read the magazine in print, or, for free, on advertising-supported websites.

To me, the resulting product of this first-generation app development strategy seems to bear a striking similarity to the end-products created on the MTV program “Pimp My Ride” — the only thing these apps are missing is the “kitchen sink” feature. As an iPad (and earlier, Kindle) user, what I’d prefer to the pimp-my-ride approach is the  “enhance my ride” or “add understanding to my ride” or “provide context to my ride” or “plan my ride,” or, as what the focus of this post is, merely “simplify my ride.”

Last week, after my third attempt to download just such a bloated magazine app, Virgin Media’s Project Magazine app, I reached my threshold of tolerance for such “magazine apps” and posted some rather opinionated observations. Apparently, that post resonated with lots of people as it has generated more traffic, tweets and back-channel email than I can recall in a long time.

Included in that email, was a message from Tim Moore, the creator of a magazine app called Letter to Jane that hit the iTunes App Store about the same time as Virgin’s Project magazine app.

There is Another Way to Design a Magazine App

If Tim were a media company and not a young photographer in Portland, Oregon, I’d say that the blog, “Letter to Jane,” is the foundation of his brand and his iPad app is his first brand extension. I don’t think such considerations really matter, in this case.

As I admitted to Tim, I wasn’t familiar with his blog or, frankly, any of the people or topics he writes about. However, Tim recognized in my post last week, that I might find his design and development decisions more in-sync with what I believe many people who actually use iPads want (vs. those who don’t use iPads, but want to pimp-out apps).

He was correct. Despite its apparent emphasis on a visual aesthetic, here are some of the obvious user-friendly features the app has, features that practically none of the magazine apps from major publishers thought to include: 1. An option to read any article in a format that is book-like (think, a page on Kindle or a display of an article using Instapaper). 2. “Copy and paste” text. 3. Hyperlinks that launch the iPad’s Safari browser.

While Tim’s app launched in the midst of the hoopla about Virgin’s Project and rumors surrounding a new News Corp iPad daily “newspaper,” an amazing thing happened last week: Tim’s app, a magazine app that is free from the clutter and bloat of all those big media, heavily hyped apps, landed on the “Top Ten” chart of the iTunes Store’s “Lifestyle Apps,” out-performing, at least for a period of time, such magazine apps as Oprah’s.

My Conversation with Tim Moore

As I found what Tim is doing a welcomed relief from the bloated magazine apps getting all the attention, I asked if he would follow the style of his app and answer a few questions from me. I opened up a shared document on Google Docs, and we had the following discussion over the weekend.

[A word of caution: The following is quite long and will be of interest to a small group of people who are designers or iPad App developers.]

Tim, Thanks for recognizing from my previous rants about the absurdity of bloated big media-backed “magazine apps,” that I should take a look at the approach you’ve followed. You are correct in thinking I’d want to point to it as an example of a better approach for early-generation iPad magazine apps.

Before I jump into the questions about your app, I’ll have to admit up front I know little about the topical focus of Letter to Jane — both your blog, and the app — so can you tell me about its origins.

letter-janeFirst off I just want to say thanks for this opportunity. I started with the blog in 2008, just after I graduated college. I am a photographer and I was trying to figure out how to share my work with people in the traditional forms I could think of: publications and galleries. Letter to Jane was just this little personal blog where I could share cool new things I saw as well as my love for classic films. Film is my biggest inspiration and the name Letter to Jane comes from a small documentary from the 1970’s by Jean-Luc Godard and Jean-Pierre Gorrin. The documentary is basically just an essay of Cold War rhetoric, but the format of the film, having a discussion about the Hanoi Jane photo, really felt like the most “blog like” film I knew of. So that’s how the blog started and a couple months later I started to get frustrated with how much free time I had on my hands in between freelance photography jobs. It was right at the point when the realization of the recession hit and work was few and far between.

I confess, when I saw the term, “Letter to Jane,” it was a new one on me, so I googled it and read the Wikipedia and IMDB entries. I was going to say I thought it clever of you to connect the idea of a documentary about a photograph with the idea of a blog that is not only a collection of visual images, but is a discussion with creative people associated with those images. At first, I thought your blog and the app were about film, but I realized that your passion for film — including everything from classics to film techniques in music videos — is what seems to be the foundation of what you’re doing.

I was inspired by the directors who made film essays, so now I try to reverse that by making the magazine follow the same principles of film making. I look at the magazine as a small personal collection of conversations. The photo essays are discussions with images, and the interviews are discussions with text. I wanted to ask some professionals who I respect about how they got their break and just how the business worked. So one day I sent an email to my favorite band at the time No Age and just said, “I’m a big fan and I’d love to talk some time and do an interview.” A month later I got a reply that said, sure let’s do it and that’s how the magazine really began. In the interview I asked probably the most honest questions I have in an interview, just because I am really interested in their creative process and I was very eager to learn from them. After that interview it was easier to get more and all of them follow that same format. Just a discussion with people I really admire. I don’t like to editorialize or edit them too much, just let creative people I like talk. I’ve seen probably every clip of the Dick Cavett show I could find and he’s been a big influence on me.

Dick Cavett? That’s fascinating. I would have guessed James Lipton. Cavett is much more witty — so, good for you. Let’s talk about your app. How did you get from blog to magazine app?

The magazine started as a PDF that I released for free last Christmas. Then when I got my hands on an iPad last April, I really fell in love with the device and started to spend countless nights learning how to program in Xcode. The first was just a port of the first issue and my skills were minimal but I really just wanted to minimize mistakes rather than try to do something outside my means. With Late Autumn (note: the name of the current issue that’s available as an app) I really took a long time at trying to figure out a way to make a magazine experience that felt like a native iPad app and as little UI (user interface) as possible so in many ways I feel that Late Autumn is my first real attempt at an iPad magazine.

Before I jump into asking you about some of the design and interface approaches you took on the app itself, let me ask about its development. Had you done any programming before?

I had never really programmed anything before. I tried to make some simple Visual Basic games that they teach in high school, but programming was never anything I even thought about doing.

I think there are some people who will read this, who that statement might inspire, so I’m going to have to ask what inspired you this time, if you’ve never even though about programming before.

I remember when the App Store first came out on the iPhone, I was reading an article about this guy who had quit his job and made a business off a simple iPhone game, I think it was called iSniper or something like that, and that really inspired me. So I downloaded Xcode and tried some tutorials and failed miserably and gave up.

Now that’s a story people can identify with, so I can’t wait to hear the finish.

A year later when the iPad came out I got inspired again and found some Youtube tutorials and completed maybe 5 of them and felt like maybe this was something I could grasp, so I registered as a developer (which at $99 a year is easily the cheapest part of any creative endeavor) and started to keep making simple test apps. With the first app, I tried to picture what the magazine would look like independent to how I would program it, and then I started to learn independently the kinds of skills I would need to make that possible. Then I began to integrate the two down the line. With the most recent app, I flipped that around because I learned from mine and other magazine apps, how important it is to grasp that you’re actually holding the art, and interacting with so it has to feel very natural, and that’s kind of what drove the latest project.

I think you’ve just inspired some would-be programmers. By the way, if you haven’t done so already, I’d recommend you read Douglas Rushkoff’s Program or be Programmed. Let’s turn to the app itself — and some questions about the choices you took as developer, not as a designer (although, I’d be the first to argue that the best lesson in your app comes from you approaching it as both). First off, Why a native iPad app and not a web app?

Well with the first iPad issue in May, my thought was that a web app would be the way to go. I’m not that great with HTML, but I certainly was more comfortable with it than Objective C at the time, so I basically made a web app and put it in a shell program. I soon realized that with the current generation of hardware, that tablets don’t have the right specs to do a web app magazine properly — or at least the way I think is proper. The small amount of memory is probably the biggest issue. A magazine has too much media to load all at once, so you have to break everything up and that creates load times which kill the experience. I’m sure the possibility to do a web app magazine perfectly will be here very soon; how quickly it will be adopted I’m not sure.

Well, you just answered a question I’ve wondered about — why an iPad-friendly web app isn’t a better approach than a native app. What about some of the third-party magazine app development tool-sets; what not use one of those rather than learn programming?

After the first issue, I kept waiting for Adobe or someone else to release some tools to integrate into my inDesign workflow, and they never came so I finally gave up on them, and started to work more and more on my coding skills. This is one spot where I think the legend of Apple’s strict policies helped my learning experience, because I never focused on learning how to do something “cool” in Xcode, but instead I just wanted to learn how to make better code. The main advantage to making a native app is that the iPad is optimized to handle big graphics. So before I made Late Autumn, I spent a lot of time learning how to make an app that used as little memory possible at any given moment so that I could make a smoother experience than last time. I’m actually still working on making things smoother. I’ve spent most of this weekend going through the app and finding areas that I can clean up and tweak to improve performance. I guess that is the main advantage over a web app, there are lots more tools to refine the “feel” of it at your fingertips. [Continued below image.]


Okay, let’s get into some of the decisions you made that I think display a lot more understanding of a “magazine app” than the bells & whistles developers. For example, you have two format options for a reader to view text. One option presents the text (in your case, interviews) in a conventional print-design format while the other option lets users read the article in the way that seems, to me at least, a more natural and native way one reads an article on an iPad or with an ebook reader like Kindle. I immediately think of Instapaper when I see that user-friendly display of text. What was your benchmark or influence for including that?

Readability is such a big deal to me, because I don’t mind being judged as good or bad based on my content, that’s fair, but I don’t want to hear, “Well I liked it but it sure was hard to navigate” because then I’ve lost a potential supporter over a technical mistake. I’ve had an iPad since they launched and tried every reading app their is. I noticed that I glanced once, maybe twice, through the magazine apps, I skimmed through most of the newspaper apps, and I spent most of my time reading in Safari, the Kindle app, and Instapaper. I think the Kindle app and Instapaper are amazing and one of the best experiences on the iPad. They’re clean, simple, and they don’t distract you while still giving you the options you want. They were definitely my main influence. Like I said earlier, discussions are a big focus of what I’m doing so I knew I had to follow in the Kindle’s footsteps and less in the magazine apps example.

featuresThe plain text mode is probably the thing I am the most proud of about this app, because it’s the simplest part of the app and yet it solved so many problems. As soon as I came up with the idea for the text option, I knew I wouldn’t have to worry about the way the main body looked. If someone found it too hard to read then they could hit the text button. Also, the majority of the reading we do online is presented vertically. So if someone feels more accustomed to reading blogs than books then I could accommodate them this way as well. Another reason for a simple reader version, was that there are no pages in this app, the text scrolls over images, and I was afraid some would have trouble reading without having a black text on white background presentation..

Here are a couple of other “think like a user” features in your app that big-budget magazine app developers seem to be going out of their way to avoid: The hyperlink and the ability to “cut and paste text” feature. It’s easy to assume why media companies are trying to ignore the web and viewing their app as an island. Or am I just not seeing the enlightened magazine apps?

After everything I just said about the plain text presentation, it honestly came about just because I was trying to figure out how to let people copy and paste, the rest was all just icing on the cake for me.

I try to read every review that comes out about these flagship iPad magazines apps, and a complaint from a lot of tech journalists that kept coming up was that they couldn’t copy a quote they liked and share it with their friends on Facebook and Twitter. Not only did I agree that this was a necessary feature, but it’s potentially a simple way to have people promote your product by letting people share pieces of your magazine with their social graph. So I started to research how to do this and I found out why most magazines don’t have this function. All magazines rely on nicely formatted text, and those options really are not found in Xcode. There are some basic type tools if you make a text label but for scrolls of text, the options are almost non-existent. If you want a magazine to look like a magazine you either have to load a webpage or use images. I’m still a new developer so I may be missing something, but if I am it’s pretty well hidden.

The plain text mode is actually the area I’m still working on the most. I haven’t really gotten enough feedback yet to find out if people want pinch and zoom functionality in that mode, so I’m holding out on it. I didn’t include that feature because I found out a neat little trick that if you do the pinch or zoom gestures on the text you can quickly select and copy the text. I find it an easier way to select a quote rather than holding your finger over the text for a second and then highlighting the proper area.

I’ll have to try that, however, that’s an example of you knowing more than the user — and having a feature that’s not intuitive.

The links idea was the most elegant way I could think of for incorporating the web into the app at the time. I remember all those horrible CD-ROM experiences and restricting information to a select few who buy my app was quite a disgusting thought. People buy apps for experiences and content should be easy to share and to search for. I took my inspiration from how I read on the internet. I click on a story, read it, and then if I want to know more, I click on a link to learn more about the subject; the app works the same way. I didn’t incorporate a browser into the app because as I said, people buy apps for experiences and since the app was built around these simple gestures, having a browser pop up, would take you out of that experience. Also most in app browsers don’t have as much functionality as the Safari app. I know it’s much easier to share bookmark, etc. if you just do it in Safari instead of in app. I wanted to work with the iPad’s natural way of doing things instead of building my own layer on top of it. Now that there is multitasking I look at it as working with the iPad and not trying to be my own island. This, like the text option, is something that I am open to changing if user feedback demands it.

A lot of my complaints regarding iPad magazine apps deal with what I think is some belief among the designers that they must “re-imaganeer” the entire way people interact with software and with magazines — as if those conventions had not developed over time. Can you share what some of your thought process was about navigation as your app reflects a desire you seem to have to balance both a certain aesthetic while, at the same time, not bringing attention to the navigation or user-interface. In other words, like anyone picking up any magazine, should know how to get from page to page, you’ve at least recognized the need for such consistency. Magazine app developers are all over the place on something as simple as “the swipe” — up-and-down means different things in different apps.

The most annoying magazine app navigation’s to me are the Adobe apps because even though I know it works on this column approach where you read vertically and then swipe horizontal to go to the next story, I still find myself constantly getting lost. I think the Adobe tools could produce something cool once they get it into people’s hands, but at the moment almost all these big companies are trying to sell us over priced tech-demos, and I honestly find it a bit insulting.

When it came to the navigation of the magazine I again went back to the apps that had the best feel, which in my mind are the Kindle and Instapaper apps. Also from the beginning I really made it a priority to not have an instructions page. My thinking is that for games or productivity apps it’s fine to have instructions, but a magazine with instructions on how to read is a failure in my eyes. I mean think about it, we actually have people who think we need instructions on how to read, one of the most basic functions of everyday life. If that doesn’t scream out bad design I don’t know what does. I’m pretty picky when it comes to print magazines as well though. I hate it when a magazine has a bunch of inserts you have to unfold to get the content. Things like that have a cool factor for about 3 seconds and then become annoying for the rest of the time it’s in my possession.

As I’ve said, if you have to include instructions on how to use a magazine app, you’ve failed — and you shouldn’t call it a magazine app. But, I think most people don’t understand that one of the most difficult design or creative challenges is to make something drop-dead simple.

Over the last couple of days I’ve had a couple people tell me that they don’t get what’s so special about this app, it seems so simple to them. I, for the most part, take that as a compliment of sorts. I make no claims that this is revolutionary, I just say that I’m trying to do things different, and by different I mean by using the methods we already know and use everyday and present a new digital element to that. Reading is one of mankind’s oldest skill sets, I don’t really see a need to reinvent it.

I think there’s a belief among media company executives that “reading” is dead — that video is what the future is all about. Which reminds me: You’re obviously someone who loves film and video, yet your app has none embedded. Why?

That is a great question and I’m surprised no one has really made that connection before! It all boils down to that I had plans to but I was never happy with the results. Through my blog I get sent a great deal of video and the current state of the medium from and indie standpoint is rather boring to me. The get bored very quickly with the semi-clever Canon 5D film student technique, and none of it really fit the style of the app so it didn’t go in. Most of the interviews are done over the phone or by email, so I didn’t have the opportunity to shoot video of them. In fact the reason I don’t include photos with the interviews is that I was so annoyed of having to use press photos in the last issue. They were all a different style and they stuck out like a sore thumb, even more so if they were included in Late Autumn. My compromise on this was that I included links to their videos and photos, so that you click the link and you can see the multimedia. This will certainly change in the next app although I’m not sure how, I’m trying a couple different ways. I have to say that while not perfect, I think The Times Eureka app has done the best job with how they incorporate embedded video because the majority of it is opt-in and not forced on you like it is in Project.

I wanted to make a 3 minute short film for this app that was in the same style as the app, but I again was never happy with the results. My current idea for the next issue is maybe not so much have a lot of video in each feature and still keep the articles fairly clean of bells and whistles, but maybe feature some one’s short film or produce my own. In other words don’t mess things up by integrating everything together but giving it it’s own space. The idea of featuring young filmmakers really interests me because I think devices like the iPad are where indie filmmakers really should be focusing more of their time. Most of them spend tons of their own money to make films that are intended for big screens, and the truth of the matter is that their film will get played at a couple festivals and then that’s it and it’s back to the small screen. There is a huge market to make smart movies for handheld devices now and it’s only going to get bigger.

What has the first version of your app taught you about what you’re going to change in the second one?

The great thing about all of this is that I’m learning something new every day and that’s always going to result in a better product. At this point I’m fairly confident in my own sense of taste and aesthetics that I know I won’t go overboard with the next issue. Issue 01 for iPad was technically bigger than Late Autumn is but Late Autumn is a much better app, because it has much more thought put into it. I think the biggest part of the process that I’m still coming to grasp with is the fact that when you read a print magazine you’re interacting with the paper and when you read an iPad magazine you’re actually interacting with the design itself. I think that could be why so many magazine apps are going overboard, because that interaction is so exciting to them. I’m more concerned with the responsibility (that may be the wrong choice of word) this new interaction brings. I know that I can design it so that if a user touches an object the page does a cool animation, but again I know cool only lasts for 3 seconds. I’m looking to find what kinds of interactions are beneficial to the reader. I really want to be more social and build a more web friendly app, but in ways that actually bring benefit to the user. Ya Flipboard’s Twitter integration is great, but when you look at say a TechCrunch story in Flipboard all the Twitter comments are just retweets of the story, there’s no useful interaction there. I have a lot of exciting ideas that I’m working hard to learn how to do, but right now I’m just trying to learn from the community. Rupert Murdoch has all the money in the world to try and fail and I have the benefit to learn from his trial and error for free.

I’m sure some people are wondering how you’ve been able to get your app noticed in the crowded App Store. Can you talk a little about how you spread the word?

I just want to preface what I’m about to say by stating that I feel I’m a competent artist, but I’m not a businessman. I helped start up a small music label before and then with getting talent and interviews for the magazine I’ve learned how to get contact and how to get through to them, but I still can’t say I know how to do any promotion effectively. All I can say is that I made the best product I could at the moment, and I’ve spent every waking minute I have promoting it, some responded, some didn’t.

I must say I have been amazed at the response to Late Autumn. The release of this issue was a huge frustration to me. I submitted the app at the end of October, and since I built the app using iOS 4.2, when 4.2 got delayed, I got delayed. So my app finally came out on the week of Thanksgiving, which means no one is in their offices so there’s no chance for me to get any press. Then the next week Richard Branson comes out of nowhere and takes up all the headlines, so I had come to the realization that maybe this app was DOA, and I should just try again next time. I remember I was watching a podcast, I think it was Macbreak Weekly or iPad Today, and they’re talking about Project and talking about what they don’t like about it and I’m just screaming to my computer, “but MY app does that!” But almost the next day things started to turn around. I must have sent out 60-100 emails a day to journalists, newspapers, review sites etc; all original, I hate to send out mass emails, and finally some of them started to pay off. I got some nice reviews from some app and design sites, and literally overnight I went from #186 in the Lifestyle section to #6 and stayed there for a while, last I checked I was at #10, but still an amazing turn around, which I am very grateful for.

I mean if I can paint it more clearly, I am just one kid with this little project trying to get some traction and then I wake up one day and I’m ahead of magazines like Esquire and GQ, with only Oprah and Martha Stewart ahead of me was something that is a bit hard to comprehend. It’s one of the weird things about today’s world where I’m having to sell my car to my dad to cover the next couple month’s rent, and at the same time I’m in a serious (well serious to me) competition with the likes of Oprah, Richard Branson, and Martha Stewart. If I was a better businessman I could take better advantage of this opportunity.

The problems I’m now facing is that it’s still hard to tell what market to promote this too. Late Autumn is not a general interest glossy. It’s a small art quarterly and it’s being thrown into competition with cooking books, big magazines, wine guides, etc. It’s really hard for me to gauge where my audience is. Tech journalists of course want to cover the tech and demo off bells and whistles, and I’m not sure if people who are really into the content I make have iPads yet. It’s obvious that I’m reaching people, but I’m just not satisfied until I’ve found a more effective method to get content to the people who want it.

You said you’re a photographer but the recession wasn’t great timing for launching such a career. Since you’re now also an iPad app developer, are you going to follow that path?

Yes, I couldn’t really ever see myself moving away from photography, but how I use it, will change. With this zine I’m working in a lot of areas where I’m learning on the fly and so my confidence is sometimes low. I’m not a trained journalist, a trained graphic designer, a trained programmer, but I have to incorporate all of those skills to make this project happen. If I make a mistake in those areas it’s visible to all, but in college I was able to make my mistakes with the art and really get comfortable. I studied photography and art/film history so I’m very comfortable in those areas. They are kind of the anchor that gives me the confidence to explore other skills. If something fails I at least know that I can bring it back to a place I feel more comfortable. That said Letter to Jane can start to feel like a bubble some times. I really would like to work with other publications and collaborate with other creative types. I feel at this point I have Letter to Jane in a position where it’s there when I have the need to get out my ideas in the most pure form possible, but all my work doesn’t have to be in Letter to Jane. I am constantly trying to learn from others, and sometimes it is a joy to just be a photographer and not photographer/designer/interviewer/blogger/editor/etc.

Thanks, Tim. I think this will be one of the longest posts ever to appear on my blog, but I’m going to post the un-abridged version as you’ve covered lots of helpful ideas and insightful lessons.

Thank you Rex