It’s Sunday morning and I’m reflecting on my failures. A few minutes ago I removed Magpie from the App Store, bringing to an end yet another in a long series of experiments that validate the hypothesis: Does Aaron know how to fail?

Oh hells yeah, Aaron knows how to fail.

On my podcast last week we received a question from a listener, which was essentially, “why does nobody talk about their failures? Why do we only hear about the success stories?” My answer at the time, glib though it may be, is pretty accurate. Nobody wants to bring attention to their lack of success, for fear of letting slip the idea that you aren’t good at what you do.

On the other hand, I’ve had so little success bringing attention to my products, I have little fear of letting the news of my failure reaching too many ears. So here’s what I want to do: lay out the failures I’ve had over the years, and describe in quick terms why I thought they failed. If you’re into failure, this is going to be a goddamn clinic on it.

Let’s go in order.

Macinsite Magazine

When: 1999
What: I thought a magazine for Canadian Mac users would be the best thing ever. As an experienced newspaper editor, and coming out of a master’s degree in publishing, I thought I could make this happen. I put together an editorial team, sold ads, and published issue 1 on July 1, 1999.
Why it failed: Pure and simple, there was not nearly enough money. While we sold 1600 copies of the first issue, advertisers didn’t come back for issue 2, and I couldn’t afford to print it. It was an ugly and embarrassing episode that saw my name mocked in the pages of Masthead magazine, an industry journal which has also since died (hey, magazines are a tough biz).

In the intervening years between Macinsite and the Aaron you know and love as the nerd-programmer, I got married, worked for The Man, and then learned to program. And then…

Code: Source Code Viewer

When: 2010
What: This was my first shipping iOS app. I was lured in by the size of the App Store market, and the stories of small developers striking it rich. An HTML source code viewer, I thought, would appeal to mobile developers, and bridged a gap missing in mobile Safari. I charged $1.99.

Why it failed: Even in 2010, there were too many apps in the store. I did the usual stuff announcing my app, sending out press releases to journalists and talking it up to everyone I knew. It sold a handful of copies. Ultimately, I didn’t even use it that much, and it was a first-time app; it honestly wasn’t that good! So it was with some relief that I removed it from sale a couple years ago.


When: 2011
What: I really felt that Code wasn’t a good-quality app, and with more practice I could write something better. I had the idea for Tiberius watching Star Trek VI: The Undiscovered Country, where Kirk’s personal log is used as evidence against him. I really admired the UI of that log, and sought to emulate it in an app. You can see more about Tiberius on my resume page. I made the app free, and charged $.99/month for an online service that let you store and share your log entries.
Why it failed: Again, getting the word out was tough. There was no specific audience for this app, except perhaps Star Trek fans. But even those I could identify didn’t seem to be that interested, so I imagine the appetite for people creating selfie videos in a futuristic interface was lower than I’d imagined. And guess what: I rarely used the app as well. I pulled the app after a few years, and nobody noticed.


When: 2013
What: App.Net was an alternative to Twitter meant to be more open, and had gained a following. As enthusiastic ADN users ourselves, my friend Adam and I agreed to write a Mac app that brought the capabilities of the iOS app Whisper (alas, nothing remains to link to about this terrific app!) to the desktop. Adam brought his wonderful design sensibilities to the app, and I coded it up. I charged $4.99 for the app.
Why it failed: In the early going it really felt like this one had legs. I ran a beta test, got terrific levels of interest and feedback. The launch went pretty well also, and early sales were substantially non-zero. But then this happened — App.Net was essentially shutting down. Overnight sales of ThreadOne died, and people left the service. It was like a giant pair of scissors snipping through the cord. It was over, no question. Lesson learned, kids: don’t build your shit on other peoples’ services.


When: 2015
What: Essentially, think of a read-it-later service like Instapaper, but made for web video. Just the ease with which I could communicate the idea made it feel like a winner. Who wouldn’t want that? Who, dammit? So I built my most ambitious app yet: one for iOS, for Mac, later for Apple TV, and a small web service to support it, all based on Apple’s Cloud Kit. A lot of moving parts, and it worked. You could readily save a video on many web pages to view later in a native video player. This was especially interesting because it scratched an itch that I had; I used, and continue to use Magpie regularly. I charged $4.99 for it on Mac and iOS/AppleTV.
Why it failed: Who wouldn’t want it? Everyone. Turns out the biggest problem with making an app for “everyone” is that you can’t just tell “everyone” anything. I’m pretty sure there are 100,000 iOS users out there who would pay $5 for this app, but I have no way to reach them. Instead, I was selling five copies a month.


When I think about this streak of mine, I can see clearly the line of thinking, the progression of ideas that are getting refined over time. As of August 2016, I have distilled the question of “what makes a successful app?” down to these bullet points:

  • Something for a niche, so you can reach them with your marketing message;
  • Something that pays via subscription, so you don’t need to sell to everyone, but rather a smaller group;
  • Something that relies on your own web service, so you control your infrastructure; and
  • Something that you need yourself, to sustain interest and drive continual improvements

Of course, this list isn’t complete without the usual standards of quality development, a novel, useful idea, and the drive and care to make it, which are intangibles and difficult to describe.

However, my next idea currently under development, ticks all these boxes. We’ll see if that makes any difference.