To clarify though, I believe the success he's had is most certainly NOT luck but rather hard work and merit. My comment was referring just to that specific article.

Did you read the very last line of his post? "I’m not sure what the lesson is here."

I don't see him giving advice to anybody. I see him recounting some rather... debatable decisions early in his career.

Yeah, but if you're recounting what has worked well for you in your career, you're giving advice - even if you qualify it at the last minute with a totally wishy washy ending like that.

Also, if you've followed Kaplan since his (awesome) "Fucked Company" website you'll know that the man is no babe in the woods. IMO he has too good a grasp on the nature and consequences of risk to be "not sure" what the lesson is here.