Outliers is a nice collection of marginally related, well written (Malcolm Gladwell, natch), stories that are ostensibly tied together by their ability to disprove the notion of a "self made man".
It's a little difficult to tease out what Gladwell thinks a "self made man" would look like, but we know what he doesn't look like: any existing human being with a family history that influenced his life. You're not a self made man if you were raised in an environment which valued education or entrepreneurship. You're not a self made man if you were a life-long computer nerd in your mid twenties at the dawn of the micro-computer revolution and became successful in that industry. You're not a self made man if you were unfairly shut out of the "best jobs" because of your ethnicity only to end up with a "second tier" job that, because of changes in society, ended up being much more lucrative than ever predicted.
What Gladwell doesn't do it look at the history of similar people with similar backgrounds. Joseph Flom presumably wasn't the only Jewish law student from an immigrant, garment industry family who couldn't get a job at the top law firms. Why was he so successful and not the others? More relevantly, why did some of them become at least reasonably successful, while others gave up (if any did)? What was it about Bill Gates' nature that drove him to sneak out of the house at 3:00am to code in the University of Washington Academic Computer Center that was not the nature of other nearby children?
Gladwell's argument is that Flom and Gates wouldn't have been able to do what they did had a fairly specific set of things not happened in their lives, but he doesn't investigate people for whom those or similar sets of things did happen. In science this is referred to as "survivor bias", and Gladwell is assuredly familiar with it.
"Self made man" is a trite, wince-inducing phrase that anyone should be embarrassed to apply to himself. But let's not pretend that all life is random chance. Or, if you want to make that claim, you have to do a better job than Gladwell does here.
In the end the book works extremely well at illustrating a point that precious few ever doubted: That the exact path of one's life is heavily influenced by family environment and elements of random chance. It that regard it's a kind of "Connections" for the social psychology set. But the stories themselves are best read as enjoyable, unrelated, long form magazine pieces.