trye, but the importance of the two criteria aren't weighted the same.
plus he isn't doubling down on the same bet: he's changing the new bet to be more in his favor, so the additional 100,000 is actually worth less than the original 100,000. (not monetary value, but rather the money's value as representation of the strength of his belief that the bubble won't pop before 2020).
'This bet is open to the first VC who would like to take it' http://blog.samaltman.com/bubble-talk
Any bets taken beyond that would be a relaxation of the 'you weren't here in time' criteria which would have excluded all other gamblers.