Are you sure H1B visas are relevant here? I would imagine EB-5 (investment) visas would be the more common route for upper class immigrant entrepreneurs coming to the US.
I know this is a very common path.
Regarding the class thing: my grandparents were blue collar workers who never went to high school, my parents were engineers.
Back when Musk would've applied, that wasn't a problem, he would've gotten an H1-B pretty easily.
While you can go straight from OPT to green card, getting an H1-B first is much better since it's dual intent, so you're not prevented from traveling during the green card application (which you would be on OPT).
Professor Norm Matloff presents a detailed critique of the H-1B visa : http://heather.cs.ucdavis.edu/h1b.html ... "The H-1B work visa is fundamentally about cheap, de facto indentured labor."
I'm not sure how lean, garage startups feel about Venture Capital's special access to guest workers for their competing "Billion Dollar Startups". I would guess that their views are little more nuanced than the Wall Street Journal's take on it.
The biggest H1-B employers , are in fact, outsourcing firms : http://www.businessweek.com/table/08/0305_h1b.htm . Their frequent editorials often fail to mention this.