That said, I like the products JF mentioned, but I think the universe of customers who like the cheeky tone of the companies he mentioned is fairly small. The Saddleback backs cost hundreds of dollars, Woot plays to an educated techie crowd, the farm he mentions is a super local business. You've got this venn diagram of people with a broad liberal education crossed with folks who have large sums of money for big discretionary purchases.
I work in the world of medical devices, specifically diabetes. It is a $130B industry and while some companies try to get conversational, the truth is most don't want a tongue in cheek/casual/authentic tone when it comes to their health. It might be conditioning, but people seem to like the idea of a massive company filled with scientists that seems "robust" if bland. I'm sure its similar in other categories.
I love the Saddleback copy, but it is not universally applicable.