Guy was Apple's chief evangelist in it's earliest days and has been involved in several successful tech ventures since. His blog is at http://blog.guykawasaki.com/ and covers a huge variety of topics.
Tony Robbins is one of the most successful figures of the self-help industry. His trademarks include the infomercials he uses to promote his products and the firewalking that occurs at his seminars. His blog is at http://training.tonyrobbins.com/
Milano blogs in addition to tweeting: http://alyssa.mlblogs.com/
We don't know for sure that Jordan Mechner is a millionaire, but it sure seems like a good guess. In 1989, Mechner programmed a little computer game called "Prince of Persia" for the Apple II, one of the earliest personal computers. 21 years later, Prince of Persia is a multi-million dollar gaming franchise with upwards of 14 titles. Those character royalties must be worth quite a bit.
Mechner's blog is made up mostly of his drawings: http://jordanmechner.com/
One of the oldest user-generated content websites on the internet is http://hotornot.com/, which allows users to post photos of themselves and be rated on a scale of 1 to 10 by other users. In fact, the founders of Youtube's original plan was to create a video version of HotOrNot. Over a decade after its launch, HotOrNot has made millions in profits and is still going steady--but the guy in the upper right part of that photograph gets comments numbering in the low single digits, if he's lucky: