If I may play devil's advocate for a moment,
Ramit's advice was good for the majority of people, those of average talent. It's safer, and while it precludes true success, it decreases the likelihood that he'll know of anyone sleeping on the streets directly due to his advice.
Particularly, since your financial situation seemed so dire (from your own emphasis), and you had a dependent that you were "fully financing" (ahem, that makes it sound like I'm talking about a new car), I would say defaulting to very conservative advice is appropriate.
It's just that conservative advice is rarely glamorous and never leads to the type of stupendous results your talent resulted in.
If I had to guess, Ramit probably didn't respond because he didn't know what to say. He could give you a lecture on results-oriented thinking being a fallacy, maybe use the analogy of gamblers at poker wining with a bad hand and thinking that means they are good...but it wouldn't matter, and probably wouldn't apply in your case anyway. That is more of a concern for the talentless hack who gets lucky. He could congratulate you on your success, but may not want to be quoted or interpreted as supporting the high-risk, high-reward route.
Or, he could just be annoyed and knows better than to say anything negative. =)
good observations. yeah, it would work for most, i suppose. There's nothing conventional about my mind though.