You are quite smart and you guessed right. Start-ups are not a guarantee to win the lottery. PG makes money with people being interested in start-ups, so he tells you about as much of the advantages as possible. And it is not like he's lying or hiding something. From all the facts he just emphasizes the ones that he thinks favor his own situation most. Both "smart hacker" and "working hard" can be interpreted in different ways. Not much of a surprise, isn't it?