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.