[It really isnt all about money.
I know a lot of people think it is, but Trump sold us on ideas.
Hillary spent plenty of money.]
Meg Whitman spent ~$150m running for governor in CA. She lost. Then again, she did not build Ebay from scratch - she parachuted in to provide adult supervision after the company was already operating. Bloomberg built Bloomberg LP from Day One, to the point it now has 20,000 employees.
And NYC might be overwhelmingly Democratic, but the Democrats habitually run a lot of goofy nitwits and losers in their mayoral elections. Just take a look at the mayor they have now as a perfect case in point.