One of the reasons that VCs and angel investors often get swelled heads is the fact that people kiss our asses all day. It feels good to have smart, talented people speak glowingly of your wisdom and plead for your help.
But the dark side of having money is the doubt it creates. If entrepreneurs want me to invest in their company, they have every incentive to flatter me, deserved or not.
Having money definitely gives you influence over others, but it also prevents you from knowing if you'd have any influence on your own merits.
Certainly, there are plenty of investors who lack the self-awareness to recognize this; they blithely barrel through the world, convinced of their own genius. Yet I suspect that even many of these people feel doubt gnawing at the edges of their unconsciousness.
Harry Potter author JK Rowling recently made news because it was revealed that she had written her latest novel under a pseudonym, Robert Galbraith. After being "outed," Rowling admitted that she had published under a pen name so that her work could be judged on its own merit, rather than as "A new novel from the creator of Harry Potter."
Rowling's gambit worked; her novel, "The Cuckoo's Calling," won extremely positive reviews...and sold a miniscule number of copies.
Sadly for the successful of Silicon Valley, it's much harder to start a company or make an investment under a pen name...but the idea might be tempting to some.