Earlier quoted context omitted.
People have been saying for years that Apple needs to come out with lower end products or they'll die. Their steadily increasing profits (even through the recession) and massive cash reserves say otherwise.
There's a big difference between being successful and being change-the-world successful. I'm sure Apple would love a piece of the latter but given their business model it probably won't happen. I can't imagine Jobs is happy about being just being a billionaire when there are guys like Gates who dwarf his wealth and success (and therefore have the cash to actually saves many more lives and alter world history)
"In Steve's mind, he has the best of everything. Apple software is cooler than Windows will ever be. Palo Alto, where Jobs lives, is trendier than Seattle. Even Jobs' plane, a Gulfstream V, is cooler than Gates' Challenger 604. It goes on and on. Gates has never even considered this latter point, but I'll guarantee you that Jobs has, and he revels in it."
http://www.pbs.org/cringely/pulpit/2002/pulpit_20020110_0007...
So, no, it is not clear at all that Steve believes that Gates is more "successful" than he is. Furthermore, it is no longer insane to imagine that, depending on how long Jobs health holds out, he could presiding over Apple one day with a higher market cap than Microsoft (consider how Apple surpassed Dell in market cap a few years back).