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...
The Mythical Man-Month: Essays on Software Engineering - https://www.amazon.com/Mythical-Man-Month-Software-Engineeri...
Hackers: Heroes of the Computer Revolution - https://www.amazon.com/Hackers-Computer-Revolution-Steven-Le...
The Cuckoo's Egg: Tracking a Spy Through the Maze of Computer Espionage - https://www.amazon.com/Cuckoos-Egg-Tracking-Computer-Espiona...
Where Wizards Stay Up Late: The Origins of the Internet - https://www.amazon.com/Where-Wizards-Stay-Up-Late/dp/0684832...
Open: How Compaq Ended IBM's PC Domination and Helped Invent Modern Computing - https://www.amazon.com/Open-Compaq-Domination-Helped-Computi...
Decline and Fall of the American Programmer - https://www.amazon.com/Decline-American-Programmer-Yourdon-1...
Rise and Resurrection of the American Programmer - https://www.amazon.com/dp/013121831X/ref=sr_1_1?dchild=1&key...
Accidental Empires: How the Boys of Silicon Valley Make Their Millions, Battle Foreign Competition, and Still Can't Get a Date - https://www.amazon.com/Robert-X-Cringely/dp/0887308554/ref=s...
Softwar: An Intimate Portrait of Larry Ellison and Oracle - https://www.amazon.com/Softwar-Intimate-Portrait-Ellison-Ora...
Winners, Losers & Microsoft - https://www.amazon.com/Winners-Losers-Microsoft-Competition-...
Microsoft Secrets - https://www.amazon.com/Microsoft-Secrets-audiobook/dp/B019G2...
The Friendly Orange Glow: The Untold Story of the PLATO System and the Dawn of Cyberculture - https://www.amazon.com/The-Friendly-Orange-Glow-audiobook/dp...
Troublemakers: Silicon Valley's Coming of Age - https://www.amazon.com/Troublemakers-Silicon-Valleys-Coming-...
Hard Drive: Bill Gates and the Making of the Microsoft Empire - https://www.amazon.com/Hard-Drive-Making-Microsoft-Empire/dp...
Masters of Doom: How Two Guys Created an Empire and Transformed Pop Culture - https://www.amazon.com/Masters-Doom-Created-Transformed-Cult...
The Supermen: The Story of Seymour Cray and The Technical Wizards Behind the Supercomputer - https://www.amazon.com/Supermen-Seymour-Technical-Wizards-Su...
Bitwise: A Life in Code - https://www.amazon.com/Bitwise-Life-Code-David-Auerbach/dp/1...
Gates - https://www.amazon.com/Gates-Microsofts-Reinvented-Industry-...
We Are The Nerds - https://www.amazon.com/We-Are-Nerds-audiobook/dp/B07H5Q5JGS/...
A People's History of Computing In The United States - https://www.amazon.com/Peoples-History-Computing-United-Stat...
Fire In The Valley: The Birth and Death of the Personal Computer - https://www.amazon.com/Fire-in-Valley-audiobook/dp/B071YYZJG...
How The Internet Happened: From Netscape to the iPhone - https://www.amazon.com/How-Internet-Happened-Netscape-iPhone...
Steve Jobs - https://www.amazon.com/Steve-Jobs-Walter-Isaacson/dp/1451648...
The Idea Factory: Bell Labs and the Great Age of American Innovation - https://www.amazon.com/Idea-Factory-Great-American-Innovatio...
Coders - https://www.amazon.com/Coders-Making-Tribe-Remaking-World/dp...
Dreaming in Code: Two Dozen Programmers, Three Years, 4,732 Bugs, and One Quest for Transcendent Software - https://www.amazon.com/Dreaming-in-Code-Scott-Rosenberg-audi...
The Pentagon's Brain: An Uncensored History of DARPA, America's Top-Secret Military Research Agency - https://www.amazon.com/Pentagons-Brain-Uncensored-Americas-T...
The Imagineers of War: The Untold Story of DARPA, the Pentagon Agency That Changed the World - https://www.amazon.com/Imagineers-War-Untold-Pentagon-Change...
The Technical and Social History of Software Engineering - https://www.amazon.com/Technical-Social-History-Software-Eng...
Also...
"The Mother of All Demos" by Doug Englebart - https://youtu.be/yJDv-zdhzMY
"Jobs vs Gates" - https://www.amazon.com/Jobs-Vs-Gates-Hippie-Nerd/dp/B077KB96...
"Welcome to Macintosh" - https://www.amazon.com/Welcome-Macintosh-Guy-Kawasaki/dp/B00...
"Pirates of Silicon Valley" - https://www.amazon.com/Pirates-Silicon-Valley-Noah-Wyle/dp/B...
"Jobs" - https://www.amazon.com/Jobs-Ashton-Kutcher/dp/B00GME2NCG/ref...
And while not a documentary, or meant to be totally historically accurate, the TV show "Halt and Catch Fire" captures a lot of the feel of the early days of the PC era, through to the advent of the Internet era.
https://www.amazon.com/I-O/dp/B00KCXJCEK/ref=sr_1_1?crid=U6Z...
And there's a ton of Macintosh history stuff captured at:
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.
The best tech startup book I've read, by a founder of a company that came up with a unique semiconductor device. They had to create their market (it had great advantages but they had to convince EEs to do something unconventional), they had to discover what made them money (selling parts or services (consulting)), etc.
If your company is going to have a lot of people and has repeatable processes (i.e. you're not developing software) The E-Myth by Michael Gerber or I suppose its revision (which I haven't read): http://www.amazon.com/E-Myth-Revisited-Small-Businesses-Abou...
He suggests that you build up any company of this nature as if you're going to franchise it.
He also has a lot of other good advice; one that comes to mind is to make sure that there's a head for every "hat", i.e. make sure every critical function is the responsibility of someone, don't let anything fall through the cracks simply because of oversight.
At the other end of the spectrum, it's no accident that Robert X. Cringely's Accidental Empires: How the Boys of Silicon Valley Make Their Millions, Battle Foreign Competition, and Still Can't Get a Date is still in print: http://www.amazon.com/Accidental-Empires-Silicon-Millions-Co...
Read/skim it if for nothing else but the lesson of how Intel, after it had gotten quite big almost died due to the innocent well intentioned actions of one man. He makes the point that high tech companies, even if they enter the Fortune 500, aren't like "normal" ones.
There's the conceit that when a company gets big enough, no one person can kill it. His example is only one of many you can find where screwing up at the technical level can with frightening speed put a high tech company on a terminal path (see the recent "When the elves leave Middle Earth" HN item for another example of this: http://news.ycombinator.com/item?id=1007750).
Accidental Empires http://www.amazon.com/Accidental-Empires-Silicon-Millions-Co...
Go To http://www.amazon.com/Engineers-Scientists-Iconoclasts-Progr...
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)