Fraser Speirs on Nice Software (he was kind enough to include SuperDuper! in the list):

...I also think it’s much harder to impart that serious ‘weightiness’ in something that doesn’t really have a physical aspect beyond the CD it comes on. Actually, the product packaging can play a part in my attitude to software. If the box looks serious and has the right texture and weight, I’m already better disposed to it.

He’s absolutely right: it is harder to give a product “presence” these days, especially when you’re “just” selling licenses on the Web. With Shirt Pocket, I’ve tried to concentrate on usability and support—key differentiators in the software market.  I also try to make our products do one “pocket-sized” thing, and do it exceptionally well… and that means a lot of time spent polishing the software and the documentation.

These are all things I did in my previous companies, too, but we would also spend an enormous amount of effort—not to mention money—on the packaging of that content.

BRIEF, for example, had two enclosed Wire-O bound manuals, on paper of significant weight, along with a tri-fold Quick Reference Card, all packaged in a nice slipcase. The graphics were printed using a high quality process, and sealed with a matte plastic film: we knew the documentation was going to be used, and we wanted to make sure it held up well, and looked good in an office. As I recall, this cost us a huge amount per-product. But we were able to charge $195 a seat, and wanted to deliver $195 of value to the user. And —whenever they picked it up—our users got a “nice” feeling from the quality materials and presentation.

The same went for Track Record, although the size of the documentation made a slipcase impractical. Instead, we used the same kind of enclosed binding in a “candy box”, with a separate “How Do I?” guide that was designed with individually cut-back pages that acted as an “index”. Less expensive to produce, but still very “nice”. (Interestingly, when we were acquired, one of the first things Compuware/NuMega did—other than remove the space between “Track” and “Record”—was cut back on the quality of the materials… and raise the price.)

It’s something I miss, actually: the physical embodiment of the work we all put into our software. A giant box full of air and a CD just doesn’t do it for me…