The Members Forum

That Jeff Lebowski was one cool dude.

Aside from the fact that he actually referred to himself as "The Dude," the iconic character from The Big Lebowsk ijust had something about him — a kind of pure coolness that's hard to describe.

His secret? He didn't try.

Tech companies, on the other hand, try with all their might to come across as cool. Sometimes, they succeed — Apple's "I'm a Mac" ads managed to project an air of coolness that stuck for years--but equally often, their attempts to connect with consumers make them look more out of touch than Mr. Magoo at a Megadeath concert.

Ultimately, it all comes down to something I call "The Dude principle of coolness": If you're actually trying, odds are, you're failing. And the harder you try, the greater those odds become.

Here are 10 times when tech companies' attempts failed miserably.