One of the highlights is a complete gallery of the winners of Pixelpalooza, their open icon design contest that ran from 1997 to 2004. They point out "how much icon design changed" over that time. It's true: at a glance you can see how the tools needed shifted from ResEdit to Photoshop to Illustrator. Early icon design was a pastime, possible with free software; the demands of the Aqua interface turned it into a business (which The Iconfactory excelled at!), requiring a not insignificant budget.
These changes more or less ended my use of custom icons on the Mac. Creating freeware icons became a luxury, and trying to distribute paid icons for personal use was a fool's errand — especially when the way to use them is still to copy and paste into an image well in the Get Info window! And from the user's point of view, forget reliably seeing your icons, given the OS X Finder's propensity to mess up the view settings for a window the second you look away from it.
The Iconfactory survived these changes with a pivot, although not a radical one. They sold their beautiful pixel art directly to companies who included them in their software as interface elements, and they partnered with developers to create apps ranging from design tools to iOS arcade games. They've diversified, and I feel more confident than ever that the factory will run for another 20 years.
For one thing, there's a new wave of customization coming in iOS 10: Messages sticker packs. The sample art used to demonstrate these at WWDC is on par with the complexity of early OS X icons. But in 2016, as opposed to 2001, the casual designer isn't priced out of creating that level of digital art. Powerful graphics tools like Acorn and Pixelmator, which is full-featured on both macOS and iOS, are available for $30 or less. Sell just a few dozen 99¢ sticker packs and you've made back your software investment. If there had been a centralized store for 32x32 pixel, 256-color icon packs on the classic Mac, I probably would have made a few bucks, and I certainly would have spent even more.
I hope that new features in iOS 10 and beyond bring back some of the simplicity and whimsy of digitally customizing our Apple devices. And if Apple gives us the means to support some independent, hobbyist artists along the way, that would be fantastic. That's where The Iconfactory started, after all.