"The companies and people we all compare ourselves to are the ones who won, and who are winning. The Googles of the world. The Dropboxes. Ev & Biz & Jack. We compare ourselves to some of the most outrageous successes in the history of the world. We compare ourselves to the winners and the survivors."John is absolutely right. The survivorship bias is one of the main reasons entrepreneurs are so vulnerable to imposter syndrome.
Yet simply avoiding survivorship bias isn't enough. Comparing yourself to others is one of the main ways the humans make themselves less happy:
"In one of the Stanford studies, Jordan and his fellow researchers asked 80 freshmen to report whether they or their peers had recently experienced various negative and positive emotional events. Time and again, the subjects underestimated how many negative experiences ("had a distressing fight," "felt sad because they missed people") their peers were having. They also overestimated how much fun ("going out with friends," "attending parties") these same peers were having. In another study, the researchers found a sample of 140 Stanford students unable to accurately gauge others' happiness even when they were evaluating the moods of people they were close to—friends, roommates and people they were dating. And in a third study, the researchers found that the more students underestimated others' negative emotions, the more they tended to report feeling lonely and brooding over their own miseries."Nor is this limited to Stanford freshmen (presumably the founders of tomorrow!). I've been around long enough to know where the bodies are buried. Many of the people that Silicon Valley founders think are "successful" are frantically paddling to stay afloat, just like everyone else. I put myself in this same category; to repurpose Twain, the rumors of my success are greatly exaggerated.
The best answer isn't to be more realistic about your comparisons, it's to focus on the things that actually matter. True happiness and fulfillment come from within, not what others do, say, or think of you. Because while motivating yourself through envy and ambition might bring financial success (though I doubt it brings more success than simply striving for its own sake), it will never bring you happiness.