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EDIT: The other thing is, it's important to have a good idea about what your employment opportunities are at the other end once you have the Ph.D, and whether or not this is a material improvement. I'm not well informed on the subject of economics, but I'd imagine that about the only thing having the Ph.D will allow you to do that you couldn't before is be a professor. And while that's fun and all, it's HARD to become a professor at the kind of institution that you'd like to be a professor at. I read a great quote that was something along the lines of "brilliant undergrads who decide to try and become professors on the basis of their Nobel laureate faculty are making a decision no more sound than the teenage girl who sees Britney Spears and decides to become a musician."
It's hard to hear this stuff - I wish I'd paid more attention to it.
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Or he could end up with opportunities like
this guy.
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Yes, he could be like that guy. How likely is it? How much competition will there be? And are there comparably good opportunities without the Ph.D? Pointing to single examples of guys with Ph.D's and saying "you could do that" isn't really the most firm foundation to make the decision on. Five years in the workforce, with promotions and raises, seems like it will probably be as good or better for many jobs where the Ph.D won't be necessary.