Not to take Reddit's / spez side, but to clarify, that's not actually what he got in cash - what he got in cash on 2023 was something around 600k.
Those 193mil was in stock. Which kind of explains his drive to monetize users and kick out third-party apps: that piece of paper is only worth that much as long as he can keep the stock value afloat.
Thing is, ME as an idea made sense. Win2K wasn't targeted to consumers, XP was in the pipeline for that, but they needed an interim version until it was ready. It looked like Win2K, but ostensibly compatible with the Win9x line. They just fucked up the execution on the internals, so it was terribly unstable.
Windows 8 had the opposite problem: it improved on Win7 internals, so it was solid, but had a terrible UI that no one asked for.
One could argue that the reason ME failed was very possibly because it was rushed. Win8, on the other hand, looks very much like designed by comitee with either very misguided designers or marketing people at the helm. Because of that, Win8 feels like a much worse failure to me.