His first startup didn't really get anywhere, he was living at his parents house for the most of it. He dropped out of university for it. His second startup g

His first startup didn't really get anywhere, he was living at his parents house for the most of it. He dropped out of university for it. His second startup got somewhere. His third one became Uber. Still for the first decade for his working life, he was less wealthy than the typical software engineer. He had the advantage of having his parents house to live at and a middle class upbringing, but millions of kids have that in the USA today. Also a 3 bedroom house was probably way more affordable when he purchased it. In the SFBA the unaffordability really only started several years ago, not counting the general real estate bubble.