Now, the legendary Silicon Valley investor is making headway on a longtime and perhaps unrealistic effort to split California into three separate states: Northern California, California (new), and Southern California.
California's secretary of State will officially certify the initiative to be included in the General Election ballot later this month.
The proposal would make California the L.A. area, Northern California and Southern Cal would be the other two new states.
Southern California would take in San Diego as well as San Bernardino, Orange, Riverside, Mono, Madera, Inyo, Tulare, Fresno, Kings, Kern and Imperial counties.
If the plan was approved by the voters, it would need to be approved by both houses of the California legislature, an unlikely prospect.
If passed by a majority of voters, it would kickstart a years-long legal battle between local and federal authorities and would eventually find its way to Congress.
Dakota, Virginia and Carolina could soon be joined by California. With its 55 electors in the Electoral College, California has always been a stronghold for the Democratic Party.
Not many Californians are on board thus far, however.
Critics of the initiative say having three Californias would actually diminish the power of Democrats.
Under the proposal, each state would have about one-third of the state population.
The CAL3 initiative has gathered 600,000 signatures, 235,000 more than required to qualify for the ballot.
You might have heard the buzz around CalExit - efforts to have California secede from the nation. He says splitting the state would lead to improvements in infrastructure and education while lowering taxes: "States will be more accountable to us and can cooperate and compete for citizens", he told the Los Angeles Times in an email last summer.