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Nate, I answered this on your blog, but here's copy-pasted response:

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Nate, design is not binary. I am a big fan of well designed sites, but at the same time I think design needs to serve a purpose.

First, In the case of DrudgeReport, people go there for hand-picked content, probably learning about the site through referrals. Although design would make things look prettier, it wouldn't attract more readers, in that case.

Second, good design doesn't mean pretty things. Imho, for most products, user-experience is more important than fancy graphics. People need to want to use your site, and then they need to be able to use your site!

Lastly, it all depends on your business. If you're building something where your content is judged by the looks of your site, then by all means go ahead and make something really sexy. However, if your site is judged by the content, make sure the usability is top-notch and you can apply a sexy skin later.

p.s. All that said, if you're releasing a new product that needs to capture attention from a wide audience or you need to stand out among competitors, then yes, you need to make sure your design (among other things) is the best on the market. After all, you want to be noticed!