Doesn't only one of those companies actually make any profit so far? And even then, its stock price still regarded as likely over-valued given the P/E ratios of any of its peers?

And the only thing that seems to be ruining him is the pure software play (Twitter)

When you change a mostly-working product, failure is probable. Especially when you attempt to monetize and politicize in a space that is diametrically against those goals.

Well he only went into these after making his fortune on paypal.

For every success story, there are 9+ failures.