[jimbokun]

Cringely has an interesting take on the relationship between Gates and Jobs and how they perceive each other.

"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).