Mark Shuttleworth earned a fortune in the dotcom era, then became the first African in space. Now he has to find other sources of excitement, so he's paying bounties to finance open-source development. One of his first projects is SchoolTool, an open-source platform for school administration. It's written in Python, and seems quite ambitious.
There are parallels here with Chandler, although SchoolTool is more of a traditional open-source project, with dispersed (mostly) volunteer labor.