Microsoft founder Bill Gates had been a billionaire for over a decade before he bought his first private plane. In 1998, after years of legendary coach travel out of Seattle’s Sea-Tac Airport—“That guy back there with the blanket over his head is Bill Gates!” people would whisper—he finally broke down and forked over $21 million for a Bombardier Challenger 604, an aircraft that seated nine or 10 people and had a 5,000-mile range. The official word from Microsoft was that travel had become so frequent for the world’s richest man that it made sense, but “he doesn’t think the company should be paying for it,” affirmed a spokesperson at the time, as if to absolve Gates from the sin of flying private.