One strategy I've tried throughout my software career is to fail often and fail fast. Any time one of my ideas reaches the point where I seriously consider building it, I immediately think about how much I could sell it for. (And for what it's worth, my second instinct, if it's not a viable product, is to open source it, which I do quite frequently.)
What this means is that over the last seven years I've built quite a few apps - many of which have been formally discontinued or become abandonware. I'm not proud of shutting down products and leaving (truthfully, very few) customers in the dark, but it's how I operate. I'd rather try new ideas and fail quickly, determining which apps work, which ones don't, then be forever afraid to try something new.
This year I'm trying three new things/products...
I'm trying each one for vastly different reasons. And I'm genuinely curious to find out which ones succeed or fail.
For Minion, I realized I was becoming too dependent on VirtualHostX. As I showed in my earlier post, 90% of my revenue comes from one app. If it should get Sherlocked or otherwise disappear, I'd be in serious trouble. So, with Minion, I set out with the goal of creating a new app, for a new niche market, that I could grow and hopefully subsidize VirtualHostX should it ever stop selling.
For Upshot, I wanted to try a new pricing model. All of my previous iOS apps have failed miserably - generating maybe a hundred bucks a month. Like many people, I've come to the realization that the paid app market is dead. If you want to make money, you have to do it with in-app purchases.
I've always steered away from in-app purchases because most implementations are so sleazy. But, after watching what Marco has done with Overcast and its one, simple in-app purchase, I decided to give it a shot.
So, I chose to test the waters by coming up with an app I could build very quickly (less than 40 hours) and sell for free with an in-app upgrade that made sense. That's where Upshot came from. It's a simple app that lets you (very) quickly take a photo, video, audio recording, or text note and upload it into Dropbox. It's a super quick way to capture notes and ideas. There are other apps on the App Store that offer similar functionality but none that do it all. Upshot will be free. For $0.99 you can turn on the ability to share your uploaded files via a short link and view your upload history.
It should be debuting on the App Store next week once Apple approves it.
Finally, I love to write - I double majored in English and published my first book my senior year of college. Although I can't write fiction to save my life, I've always had a knack for explaining things. Because of that, I've been following along the last few years as self-published ebooks, particularly technical books, have taken off on Gumroad and LeanPub.
I knew I wanted to test those waters, but never had an idea. However, literally the night before my wife went into labor on New Year's Eve, I had one walking to my car. I've spent the last year organizing my photo collection and developing a workflow to stay on top of our ever growing photo library. And I've come up with a GTD-based workflow and honed my tools and automation techniques to make it as simple as possible. There's no reason I couldn't put together a moderately long ebook explaining and teaching my process.
So that night, six hours before my wife went into labor, I furiously jotted down into OmniOutliner everything I could possibly think of and everything I've learned about organizing my photo library. That five page outline has since then turned into the book I'm 60% finished with writing and hope to publish before the end of the Summer.
I really have no idea what to expect sales-wise. I'm hoping over the rest of the year to sell 1,500 to 2,000 copies. And at $19 a sale, that could be an incredible addition to my app revenue.
With all that said, my point is you've got to keep trying new things. You can't rely on one past success to last you forever. In my case, that success was VirtualHostX. It's had a tremendous seven year run - and I don't foresee it going away soon - but I have to take measures to be prepared for when it does.