Microsoft made plenty of money between 1998 and 2014. They also basically ceased innovating. I was a child and teenager during Microsoft's glory days from 1985-2000. They were basically unstoppable: if you thought you had a good software-related idea, Microsoft was already doing it, doing it better, and bringing some nasty market-power tricks to bear (much like Google in their glory days from ~2000-2015). I started my career soon after the DoJ consent decree, and Microsoft became a joke. They were the 800 lb. gorilla that sat in the corner milking their Windows/IE/Office monopolies (and eventually losing them) while the web became a bigger platform than Windows ever was.
Losing them? Nearly all the business workspace I know is Windows-only. Maybe not in Silicon Valley or top tech schools, but Windows is the norm for most businesses. It's not a competitive marketplace.
Quite often, I see wealthy, influential members of the tech community speak out against regulatory function citing things like lost innovation, when the reality is that they were pretty financially motivated to disparage government action in the first place. Again, that’s not to say that this executive was lying, but he clearly makes negative statements around the antitrust case and had a clear financial reason for doing so. He’s not a neutral party making an objective observation here.
/r/selfawarewolves
That is not to say it is not worth sending Google through a similar period of moribundity until they find new leadership and markets to pursue.
I’m not suggesting that he’s lying, but it’s important to remember that the anti-trust action likely had a financial impact on him, particularly if he had a lot of comp tied up in company stock.
Here we are 20 something years later and Microsoft looks to be just doing just fine to me.