Gotta live in the bay area to start, that alone is a challenge unless you're already wealthy. Gotta know who to talk to and how to talk to get money. Gotta have a degree. Gotta have friends who can be your co-founders/early employees or connections. Gotta know how to look right to the angel investors and the VCs.
The idea that the average invested company represents anything more than a group of people with an in and a talent for schmoozing is easily refuted just by observation. Sure some of them have solid fundamentals, but most are bullshit.
There was a tweet, since deleted, a while ago by Ben Dreyfuss (son of Richard Dreyfuss) who is now a writer at Mother Jones. He was attempting to explain how everyone assumes his parents carried him and related the story of being given 140k by his mom to try to make it in Hollywood, after three years he ran out of money and gave up. That story, along with Trump's "small loan of a million dollars" is really not so different from the typical SV startup story. There are countless small companies who are given "small loans of a few million dollars" based on who they know and generally seeming like they aren't complete morons. And yet few in that system would draw a parallel to the sort of privilege and wealth of Trump's ilk, though substantially there are many similarities.
The folks in SV tend to dress down and avoid excess signs of luxury until they've "made it" proper, but it's not as far removed from rich parents giving their spoiled children cushy jobs in the family business as most people would hope.
A lot of what you said is based on truth, this isn't.