So, I said he'd be considered rational in all cases except hold/fail. That's because people will take his success as evidence that he knows what he's doing, and if he sells then he's doing what 'everyone else' (i.e. > 99.9% of the world) would do, so even if it doesn't work out that way they'd probably give him some slack.

Also, I think it's rational for him to diversify, but it's not a bad idea for him to maintain significant holdings.