Lessig seems to forget that this country is not, nor has it ever been, a "democracy". This nation has always been a Republic.
The rules in place that he describes as "fixed" are an attempt (however feeble) at preventing the balance of power from being held by any one part of the country. Who would really enjoy it, for example, if California got choose presidents all by itself, simply because they had more people than most other states? (Yes, I'm quite aware that a few other states on the East Coast also have a lot of people, but at this writing, California has more Representatives in Congress, and therefore more Electoral votes, than any one of them.)
Besides that... His choices for VP would be Elizabeth "Hoaxahontas" Warren and Bernie "Socialism or bust" Sanders? Please.