I don't have enough energy today to write something more elaborate, so I am just going to recommend this essay.
Here is a fragment:
We could choose from any number of tech success stories as our case study in bad quest selection. But perhaps the best example of an alumni-network “random-bad-quest-generator” is Facebook.
In 2012, Facebook had one of the highest-profile IPOs in history. Overnight, dozens of its executives became simultaneously wealthy and famous. The question of the day was what they would do with all of their newfound social capital and leverage. Would this be a sequel to the Valley’s legendary PayPal Mafia, in which the founding team of a paradigm-altering technology company continued on to found and fund an entire generation of paradigm-altering technology companies?
It would not.
Despite the rare and precious opportunity to embark on ambitious second acts, almost everyone in the Facebook Mafia played it safe. Most alums started venture capital funds (i.e. Slow Ventures), or worked as GPs at existing funds (Kleiner Perkins, or General Catalyst). Alums who started new companies nearly all built derivative software products. Such quests would never be remembered. Today, even the name “Facebook Mafia,” once in vogue for all of its potential, has nearly been forgotten.