Microsoft provides the default OS for the vast majority of corporate machines + corporate suites on top of that. I think being a more creative underdog yet still being a similar size is quite impressive.By that measure, he would be even more impressed that Microsoft is a 3.8 trillion dollar company today.
That said Tesla's apparently the most valuable company in terms of market cap because investors still think it can dominate the entire EV market. I question why given the market's now over-crowded, they're no longer the default option and they've alienated their key demographic.
Things can flip very quickly! Intel's probably an example of that (as is Nvidia).