Facebook founder and CEO Mark Zuckerberg should have learned that lesson when definitive reports came in showing his $100 million donation to the Newark Public Schools had been largely wasted by the unions, lawyers and consultants who infest the system. Sadly, he doubled down on the same mistake last week with another $120 million donation to Bay Area public school systems. The fate of that money won't be much different.
But Zuckerberg's big mistakes are not all that different than the money his peers have lost in their efforts to back political candidates. They too will see more failures, but eventually a Silicon Valley millionaire/billionaire will win a key elected office.
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The one ingredient Silicon Valley candidates really need, besides a little more experience, is candor. Silicon Valley's leaders should talk more openly about how they're the beneficiaries of some of the freest market capitalism in the world today. And they should talk about how that economic freedom would be a good thing for everyone in terms that go well beyond Google's almost laughable "Don't Be Evil" credo.
These superstars need to explain that the tech sector still enjoys relative regulatory freedom while so many other American industries have been strangled by regulations, taxes and high labor costs. Silicon Valley's biggest winners should promise to re-introduce their kind of economic freedom to other sectors of the economy and disparate regions of the country.
That's the kind of "spreading the wealth" message all voters can get behind.
So Silicon Valley's foray into campaigns and elections is still clearly in the beta testing stage, and that means there's more trial and error to come. But like all oil, real estate, and banking millionaires who came before them, they'll eventually break through on election day.
Commentary by Jake Novak, supervising producer of "Street Signs." Follow him on Twitter