Tim Draper has more money than sense, particularly political sense based on his political failures to date. However, the ballot measure does have a certain appeal You can download the PDF copy of it here. His measure designates six states by counties to be in the six new states. But it allows the counties to decide to be in different states if they so desire.
The smallest of the new states by population is Jefferson with slightly less than a million people. The next smallest one has 3.5 million and the remainder are much larger.
The problem is that the measure combines counties that do not have anything in common. Draper's proposal uses horizontal divisions of the north part of the State which fly in the face of geology, geography, demographics, political orientation, etc. However, it wouldn't be too bad overall if most of the Coastal counties in North California and Jefferson were combined with Silicon Valley and the inland counties in North California were combined with Jefferson, reducing the number of new states to Five.
It all depends on Congress approving the proposal if the California voters approved it. I won't hold my breath.