The thing I remember Derek the most for is CD Baby and the grand switch from PHP to Rails which was cancelled after two years; causing great controversy.
His entrepreneur philosophy has beauty to it, but he was totally off track about the whole PHP/Rails thing. Of course it'll take forever to rewrite an entire company (practically) in a different framework. Don't do that. If you want Rails, switch over incrementally to avoid a Big Bang and use it for new projects.