https://www.amazon.com/Insanely-Great-Macintosh-Computer-Eve...
And not sure how well it's aged, but I remember "Accidental Empires: How the Boys of Silicon Valley Make Their Millions, Battle Foreign Competition, and Still Can't Get a Date" was a fun, breezy read.
https://www.amazon.com/Accidental-Empires-Silicon-Millions-C...
https://www.amazon.com/Accidental-Empires-Silicon-Millions-C...
...more for fun historical perspective than anything else. Lots of great anecdotes and stories about founders. The book became a PBS series that become a movie with Noah Wiley as Steve Jobs. And useful insight:
"As inventive organizations grow and mature, they often convert themselves into maintenance organizations, dedicated to doing revisions of formerly inventive products and boring as hell for the original programmers who were used to living on adrenalin rushes and junk food. This transition time, from inventive to maintenance, is a time of crisis for these companies and their founders."
Commandos are people who love challenges and hate structure. They'll happily take on missions that other people think are crazy or impossible, because doing things other people think are crazy or impossible is what turns them on. They get you your critical early beachhead by swimming in at midnight with a knife in their teeth and slitting throats till morning.
Infantry are what most people are. Most people are not Rambo; crazy suicide missions don't turn them on. But at this point you have your foothold on the beach, so suicide missions are few; what you need now is lots of people to take that foothold and widen it into a big enough space to sustain yourself on indefinitely. This work is kind of a grind, so it doesn't appeal to the commandos, who start falling away looking for a new beach to storm. But it's critical for turning the company from a proof-of-concept into a real, going concern.
Eventually the fight for the beach ends, and the battle moves inland. But you still need to have some people there to maintain order, which is where the police come in. Police are even more risk-averse than infantry; they're caretakers who see their job less as expanding the market the commandos and infantry have won then as making sure it doesn't fall apart. Commandos and infantry fight to win; police fight to not lose.
All of these personality types are important at varying stages in a company's life, he writes, but the big challenge is making sure you have the right ones at the right stages, and that you manage the transitions between those stages well. A mostly-commandos startup that takes off but tries to still keep itself mostly commandos will choke on its own success. A larger company that still has growth opportunities but phases out its infantry in favor of police too early will miss those opportunities and get ground down by more aggressive competitors. A company that's grown as much as it can grow but resists bringing on police will run itself down launching futile new products that the market isn't asking for. Etc.
Cringely's more recent work has been kind of hit or miss, though.
In high tech this can get really messy, these are frequently inherently more fragile companies. My favorite example is from Robert X. Cringley in this great book: http://www.amazon.com/Accidental-Empires-Silicon-Millions-Co... ; from memory:
One day Intel's yields suddenly went to hell (that's the ratio of working die on a wafer to non-working, and is a key to profitability). And no matter how hard they tried, they could only narrow it down to the wafers being contaminated, but the wafer supplier swore up and down they were shipping good stuff, and they were. So eventually they tasked a guy to follow packages from the supplier all the way to the fab lines, and he found the problem in Intel's receiving department. Where a clerk was breaking open the sealed packages and counting out the wafers on his desk to make damned sure Intel was getting its money worth....
His point is that you can have a Fortune 500 company, normally thought to be stable companies that won't go "poof" without ample warning, in which there are many more people than in previous kinds of companies who can very quickly kill it dead.
https://www.folklore.org/
https://steveblank.com/
https://www.amazon.com/Hackers-Computer-Revolution-Steven-Le...
https://www.amazon.com/Accidental-Empires-Silicon-Millions-C...
https://www.cringely.com/2013/02/04/accidental-empires-part-...
(all the chapters are there)