This seems odd to me, given that he looks (from the outside at least) to be one of the most ambitious CEO's around. E.g. Building a fulfilment network to compete with Amazon.
From the inside, he has an ego like Elon and focus like Dorsey. Several of his executives are very good at managing him, but he lives in and broadcasts from a white void detached from reality.
Can I ask what your source for this is? Perhaps you're an ex-employee?
I never worked under Tobi directly (or even close), but I was almost always thoroughly impressed with his communication and direction. I think I have a totally different take than the one you stated. The only axis I could see Elon & Tobi both sitting on is being members of the tres comas club.
Externally he has a personal writer whose whole job it is to make him seem smart. He's the darling of the Canadian tech industry, which badly needed a win since the implosion of Nortel, so he has a ton of advantages. In SV he would be a mediocre wannabe founder but in Ottawa he's hot shit.
That seems disingenuous at best—the man helped create Ruby on Rails & founded a mutli-billion dollar tech startup that has been wildly successful. Is there really any ground to question his intelligence, or rather, whether or not he's smart?
