Richard is a tremendous hacker, but he's a lousy salesman. I'm not a big fan of salespeople in general, but guys like DHH have proved that it's not enough to be a great hacker if you want your code and ideas to flourish. You need to understand that marketing really does matter.
Glad to hear he's lightened up a bit over the years, though. Maybe GNU will finally see a rebranding. GNU is such an ugly logo.