I don't think the article misses the point. He never says Bill Gates and Mark Zuckerberg should never have dropped out. He's just saying that dropping out should be rare. For the vast majority of people, it's not the right thing to do, financially. The "right people" will ignore all the discouragement and drop out anyway. People like Sergey Brin & Larry Page will drop out, with or without Thiel's investment.

"It's better to discourage than to encourage dropping out, so that it's done only for compelling reasons."