I get what he's saying, but I think he's mixing apples and oranges in some of his examples. In a blog post, you want something eye-catching, so simple and aesthetically pleasing is the way to go. For things like Craigslist, it needs to be functional.

Simpler is not always better, if that was his point. But more complicated can turn people off also. It depends on the audience and the function. Photoshop is complicated. It turns off a lot of people. I've heard many people say they're not willing to learn all of that. Photoshop's audience isn't those people. Photoshop's audience is the people who are willing to learn to make the most of the software for artistic design. Those people are willing to take the time to learn it, and they pay a premium for it also.

Conversely, if Apple had made the iPod as complicated as his second picture, a lot less people would buy it. The learning curve would be too high. Apple made it easy enough to learn with enough back end features to attract a much bigger audience. For a relatively low-cost product, it would have to be very popular for it to be very profitable. The article didn't take into account the business aspects of the functionality very much.

mk (since you linked this article), was any of this philosophy incorporated in the design of Hubski? Is the intention to be more minimal or more functional and how do you know when those two concepts intersect?