14 different positions since 2001? Unless we are talking yoga, please provide details because I see something very different on his LinkedIn page. No - being a graduate student does not count as a position in my mind so I'm trying to understand the math here.

Speaking of his LinkedIn page, what I notice is a steady increase in responsibility and/or position prestige (either in role or company) along with a strong analytical & financial overlay. The ambition he has is evident in his career path imo. Let this be the cream of the crop. No qualms here when context (something your post lacked) is considered.