Co-founder and CEO of 37signals (Basecamp, HEY); co-author of Rework, Remote and It Does Not Have to Be Crazy at Work.
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5 of Jason Fried's claims fit 4 mental models. Most often: Curse of knowledge, Affordances and signifiers, Design is how it works.
Once you know something, you cannot remember not knowing it. Fresh eyes see what you no longer can: a newcomer's, or your own after time away.
Their wordsThings that look good at the end of the day often don’t look good the next morning.
Their wordsThe end of the day has a way of convincing you what you’ve done is good. The next morning has a way of telling the you truth.
An interface should show what can be done and where, and give people a model of how it works.
Their wordsBig flat toggle buttons under satisfying tension. Clear affordances. You push them down, not in. One click catches, one doesn't. You can use them with bare hands, oven mitts, fingers coated in slippery whatever. Doesn't matter. Plenty of surface area. Outstanding design. It's all been downhill from there.
Judge a design by what it does for the person using it, not only by how it looks.
Their wordsIn some cases, design is what something looks like. In other cases, design is how something works. But the most interesting designs to me are when design changes your behavior. Even the smallest details can change how someone interacts with something.
Do what you are relatively best at and trade for the rest (comparative advantage); it holds until power or change breaks it.
Their wordsThey don't hate technology. But building and maintaining their own critical systems isn't their wheelhouse, regardless of how much faster and easier it's become.