He makes a huge deal about how he killed MySpaceSupport.com by rewiring the URLs, etc and how this eliminated all his revenue, permanently, so that he sold it off in 2008. I'm sure it was a major factor, but I think the changes in the economy, the popularity and demographics of MySpace, and the rise of more popular social networks may have also mattered.
It's not clear whether he just made the basic mistake of not 301 redirecting the old Urls, or was it that he did but still lost places anyway? Perhaps there is more too it than just a new set of Urls (in terms of search engine rankings)