The only way to win is not to scale. Most of the problems discussed by PG and in this post revolve around scaling company culture, and the associated management style, as the company grows the number of employees. Unfortunately, my feeling is that there really is no great solution to communication problems after a company scales to 20, or 50, or 200 (choose your favorite) people. Modern tools are helping more and more (GDocs, calendars, meeting transcription, ...), but after you get past 15-25 people, you go from everyone knowing everything to something less good. There's no reason that companies "need to scale". You can make millions of dollars without scaling up, and you can avoid many of the problems that kill companies at the same time -- investment overhang, cultural changes, management challenges, and the need to expand your customer base.
This might be the misuse that Graham warns us about when he said "as soon as the concept of founder mode becomes established...".
Sure, let's turn a complex subject into some formulaic process of applying superficial lessons from one small experiment relating to documentation and "trust". That's super easy. Is there a for dummies book?
Cantrill's reputation isn't relevant here. It is what it is, and there are no big-scale Apples's or AirBnb's in it. A decent technologist, I'd say. His advice is "almost" specific, and not in the least way actionable without the bits that are left out.
One cannot teach charisma, or leadership at that level. The exceptional founder, doing whatever voodoo they do, can convince others to follow him, or her, up the hill, with discipline, succeed, and not get everyone killed. That isn't a science; it's not an art; it's a gift. That's why they're special, and why it can't be reduced to a set of mechanical rules. This post was "five easy pieces for founder mode".