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I find it odd that a freemium model was never considered by Tumblr. It has worked for WordPress.com, which is very similar.

http://en.support.wordpress.com/upgrades/

http://vip.wordpress.com

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Wordpress is used by people managing professional identities and business related content, Tumblr is predominantly young people wasting time on the internet.

Tumblr seems to have toyed with this idea a bit in their paid/premium themes section: http://www.tumblr.com/themes/tagged/premium

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