Founders as Insider-Outsider Paradox

"Normally we expect opposite traits to be mutually exclusive: a normal person can’t be both rich and poor at the same time, for instance. But it happens all the time to founders: startup CEOs can be cash poor but millionaires on paper. They may oscillate between sullen jerkiness and appealing charisma. Almost all successful entrepreneurs are simultaneously insiders and outsiders. And when they do succeed, they attract both fame and infamy. When you plot them out, founders’ traits appear to follow an inverse normal distribution:"

"Just as the legal attack on Microsoft was ending Bill Gates’s dominance, Steve Jobs’s return to Apple demonstrated the irreplaceable value of a company’s founder. In some ways, Steve Jobs and Bill Gates were opposites. Jobs was an artist, preferred closed systems, and spent his time thinking about great products above all else; Gates was a businessman, kept his products open, and wanted to run the world. But both were insider/outsiders, and both pushed the companies they started to achievements that nobody else would have been able to match."

"A unique founder can make authoritative decisions, inspire strong personal loyalty, and plan ahead for decades."

"Apple’s value crucially depended on the singular vision of a particular person. This hints at the strange way in which the companies that create new technology often resemble feudal monarchies rather than organizations that are supposedly more “modern.”"