Over the years I've watched this exact conversation play out, dozens of times. I personally was inspired to leave Sun by a guy I know who worked there, and seemed like a complete idiot, who joined a startup and subsequently got reasonably wealthy [1]. The other bit of experience I brought to the table was growing up in Las Vegas Nevada where money was a sort of 'quantum' thing in that sometimes you had it, sometimes you didn't.
The Facebook story is definitely not "a single guy with a computer," which the movie The Social Network should have made abundantly clear, but it does reflect Zuckerberg's singular dedication to his vision of what it should be. Not surprisingly I know other CEOs who have carried that same sort of singular vision in companies right into the ground. That Facebook is IPO'ing today is great, but its story is at least as much luck and circumstance as it is the story of the CEO and his ideas.
What is also true is that human nature involves evaluation of self, and that evaluation is done most strongly against peers. Many people experience it at their first significant High School or College reunion. It goes like this:
"Hey Bob, wow, its been 5 years since Alma Mater U, how is it going?"
"Hi Alice, well I'm really excited because my wife and I just bought a plane! Can you believe it?! You know I've always loved flying and well when I sold Foobits I had some extra cash and its been great! It's surprisingly economical to fly up and down the coast rather than driving for flying commercially ..."
Now if Alice hasn't been as 'successful' as Bob and she feels like she left Alma Mater U with the same 'chances' as Bob did, she might feel any number of negative emotions, anger, shame, jealousy, Etc. Contrast that with the second scenario:
"Hey Charlie, wow its been 5 years since Alma Mater U how is it going?"
"Hey Alice, well its going alright. I managed save up enough to get a house but with the big crash that's underwater. The downturn hit my industry pretty hard and so I've been consulting and what not but now I'm looking into a way to strategically exit my house without having to have a foreclosure or a bankruptcy on my record, but I know its pretty hard everywhere, how about you?"
Now if Alice in this scenario isn't looking at a personal bankruptcy before the age of 25, and is gainfully employed, she might naturally feel like her talents combined with the equivalent experience at Alma Mater U has given her an edge over folks like Charlie. She feels good about her choices.
But what is really happening is that the first 10 years 'out of the gate', starting with the last year of college will show huge variations in 'success' across your peers. Some will prosper quickly, some will spiral into poverty, some will vanish into the fabric of 9 to 5 life and others will quietly end their lives, the whole range of outcomes both good and bad.
And all during that time/process people will be trying to sort out how much of the success or lack of success of their peers reflects on their own success or lack of success. As folks work through that process they sometimes become enlightened, sometimes bitter, often cynical, and ideally wiser.
[1] "Reasonably wealthy" in this context means one could live off the proceeds with a middle income lifestyle without further employment.