He does have a point that if they didn't execute well the first time, that doesn't bode well for the next try. However, that's not a problem with capitalization, that would be a problem with the team.
I was on the Odeo team that became Twitter. We were overcapitalized for a podcasting startup and that's exactly why we ended up with a bigger hit. We had the runway to experiment and the knowledge that we hadn't hit on anything big enough, so we kept trying new things.
In that case overcapitalization wasn't a problem in terms of being successful.