Drawing a blanket conclusion from a single comparison of only two samples is a hasty generalization. Downvoting somebody out of comfort for your fallacy is kind of assholish.
When you look at that pivotal moment when MS and DR were sent off on completely different trajectories by the 800 pound gorilla that IBM was at the time, it's unquestionably the headstart one. While Kildall was just trying to get a good price for their product/expertise (solid middle-class thinking at its best, nothing wrong with that), Gates was already playing the high-level game, brokering between IBM and SCP by merit of a foot in the door via family ties.
It seems unreasonable and uncharitable to imply that people are building their worldviews off of the stories of Gates and Kildall alone.
Edit: how rude of me to ask for evidence!
Moreover it’s kind of missing the forest for the trees...yes, pedigree might not have literally been the differentiator between these two specific entrepreneurs. But do you have any meaningful critique to the basic idea that people with better than average starts in life have better than average outcomes? That is what is primarily under discussion here, not Bill Gates in particular.
IBM knew about Gates, and went to Kildall first (in fact, Gates suggested Kildall to them). Why would they have gone if "pedigree" was what they cared about? Kildall had what they wanted, Gates did not. It dropped in Kildall's lap, and he botched it. IBM went back to Gates, and Gates didn't need to be asked twice.
Even if that network wasn't actively involved at all (e.g. by notifying Bill of the opportunity to supply BASIC, I think it is highly unlikely that it want involved at least that amount), the buyers at IBM would definitely have been aware of his family ties and unconsciously or not have awarded more default trust than to a random stranger. It is also not unlikely that Microsoft was given a chance in hope of currying favors with a certain person high in their own org chart or in fear of negative repercussions. Both the hoping/fearing and the favors/repercussions don't even have to happen voluntarily or consciously, it's hard enough to suppress those effects when you become aware of them and don't want to be that kind of person.
IBM was looking for microcomputer software. Microsoft was the biggest player in that field at the time. Why would IBM not have contacted Gates?
The fact is IBM passed over pedigree Gates and went to Kildall FIRST and Kildall was offered the deal FIRST. All Kildall had to do was say "yes". The notion that one had to be born wealthy to get that deal is simply false.
Kildall was not some ignorant yokel from the backwoods. Besides, titans of the computer industry do deals with yokels all the time.
In fact, Kildall did later make a deal with IBM to sell an IBM branded CPM/86 for the PC. Consumers had a choice between IBM PC-DOS, and IBM CPM/86. The former was $40, the latter $240. People (like me) chose the cheaper one, because nobody could explain what was better about CPM/86. And the rest is history.
Maybe that is the misunderstanding that kept this discussion alive for so long: I'm not trying to privilege-shame anyone, just questioning the claim that it did not make a difference at all. (Actually I think that privilege-shaming is a really stupid concept, it won't ever achieve more than make its targets bitter or cynical, if it has an effect at all. It's not wrong to take an opportunity, just don't force it through improper means)
(Now I'm off to reminisce about GEM)