Regarding their jobs, I'll just list them by their initals. A. Promoting, Organizer, Black Hat SEO for a while. B. Freelance Computer Repair, programs PHP. Wants to build a business once he's 18. D. Computer Sales "Afilliate" proably hits it closest. Then some other gigs he didn't (want to) tell me about. D. Drug Dealing, lower-mid distribution chain. He did it in highschool because it was easy money. J. Marketing in an ad-agency, and for some reason he quit biomed to become carpenter. J is an outlier.
I have to say though that only 3 of them are Americans.
On self esteem, I've spent considerable time with this group, and I'm relatively sure that they've got high self esteem, regardless of whether they were marketing or not. It's generally hard to judge a persons self esteem acurately. You can generally guess it after spending some time with the person, seeing such things as their general confidence (which is expressed through body language more than you might think), and how they react when encountering opportunities and obstacles.
Also, about your little case study -- 1000 people constitutes a large enough swath of 300+ million Americans, so I don't have a problem with 5 people that actually exist being a good enough case study.
A guess as to your observation: Do you know what kinds of jobs they've had as teens/young adults? Many of the starter jobs are related to sales, in some form or another (best buy, verizon, places teens know something tech related might work, even places like carwashes, etc), and (just spitballin here), I think the role of a silver tongued deal-maker is very popular in many upper to lower middle class and even lower class groups. Marketing seems like a natural extension of that. Also, I've always thought of marketing as the attractive, relatively business-minded person's liberal arts degree (but maybe that's just me).
Also, on self-esteem, it's sometimes something you can't tell from just looking. It's kind of their job as marketers to have very very high self esteem. If you get a pitch from a marketer, and they look like they have even the slightest doubt that their plan will fail and NOT bring in piles of cash, then you're dealing with a bad marketer.