Serious question: How can someone find the time to be CEO of two companies? I can't imagine even being a full-time engineer at two companies.
Also the above commenter's point, talking to people 16 hours a day does not mean you're working. An engineer's work is quantifiable, so they can be held accountable when they claim they work 16 hours a day. Not so for a manager. Their effect (good or bad) is far more difficult to quantify.
Then again, somehow he's doing it.
edit: Alternatively, he could live in the mission and then walk between the 2 offices during the day, they're right next to each other.
The Tenderloin's on the opposite side of city hall.