I've been reading High Tech case studies now since the 80s – just after I entered the business. Bryan Cantrill from Oxide Computer's podcast inspired me to get all my books out and order them on a rough historical basis. I thought listing them here might be interesting to someone. All of these I've read and there are a ton of lessons for entrepreneurs here. I put rough notes next to some of them in bold after the author name in quotes.

Change Log

  • 2022-06-27 - Added book of the week
  • 2022-06-26 - Cleaned my bookcase and looked for other books in this category and added entries for How Would You Move Mount Fuji (Microsoft category), Go To (Misc / Software Category), Building a Successful Software Business (Misc / Software Category), Side Hustles (Misc / Software Category), Facebook by Steven Levy (Web 2 category), Tim Cook (Apple Category), A Piece of the Computer Pie (IBM Category), In Search of Stupidity (Misc / Software Category), Crypto (Misc / Software Category), Smart and Gets Things Done (Software Category), The Effective Engineer (Misc / Software Category), Creativity Inc (Apple Category), The Chip (Intel Category), Lean In (Web 2 Category), No Such Thing as a Free Gift (Microsoft Category), The Phoenix Project (Misc / Software Category)
  • 2022-06-26 - Added Sub Categories in the Apple Section
  • 2022-06-26 - Added Sub Categories in the Web 2 Section
  • 2022-06-23 - Started adding links, added books suggested on Twitter, Added Gaskins on PowerPoint History; fixed typos (how did I possibly misspell Torvalds; clearly was stupid yesterday)
  • 2022-06-23 - Apologies for where an Audible audio book is linked instead of hard or paperback; Amazon is inconsistent with this
  • 2022-06-23 - Added a bunch more notes from reading these.

Book of the Week

In Search of Stupidity: Over 20 Years of High Tech Marketing Disasters

High Tech Stupidity

View on Amazon

This is an absolute gem of a book. There is a lot of humor here but the best bits, the parts I underline, start on Page 308 where he outlines positioning for a software product. In an extremely telling bit of analysis, he opens the book by looking at software companies in 1984 and then 2001. Even though there were a number of companies both larger than Microsoft or approximately Microsoft's size, in 2001, the next runner up, Adobe, is 1/20th of Microsoft's size. This he attributes to Microsoft being the only company "that never made a fatal, stupid mistake". And, yes, Ashton-Tate is part of the 1984 list. A bit dated but it is also timeless. Recommended

IBM / Mainframes / Super Computers


  • The Ultimate Entrepreneur by Glenn Rifkin and George Harrar; "A fantastic read. Cantrill argues in his podcast that DEC had too many people – and they did – but they grew up in an era where you made everything right down to the cases. That leads to an incredible number of people."
  • Riding the Runaway Horse by Charles Kenney
  • Soul of a New Machine by Tracy Kidder; "The canonical high tech read; I've been re-reading this book roughly once a decade since the 80s"
  • DEC is Dead Long Live DEC by Schein; HAVE NOT READ YET

Internet History

The Phone Company



  • Dealers of Lightning by Michael Hiltzik; "It makes you realize just how bright the PARC folks were; sort of a mini manhattan project for computing"
  • Copies in Seconds by David Owen; "Explains how Xerox afforded PARC. Today we don't realize the power of making copies but it was transformative"


  • The Friendly Orange Glow by Brian Dear; "One of my absolute favorites; everything we do online today happened here first (and then in Lotus Notes by Ray Ozzie but thank the FSM that went away)"

Early Silicon Valley



  • Bloomberg by Bloomberg by Michael Bloomberg and Matthew Winkler; "Makes you realize just how fundamental Bloomberg is"

George Lucas

The PC Era


Apple / Jobs / Pixar / Next

Apple Early


The Middle Years

Steve Wozniak

  • iWoz by Steve Wozniak

Steve Jobs



Take 2: The Return of Steve and Beyond



  • Creative Selection by Ken Kocienda; "This was written by the guy who created the auto correct algorithms on the iPhone and is amazing to understand how that one innovation came to be"
  • The One Device by Brian Merchant

Venture Capital


  • Softwar by Matthew Symonds
  • The Difference Between God and Larry Ellison by Mike Wilson; "This book helps you understand Oracle and how sales people really work. The Go for the Gold program and Oracle's insanity in paying commissions on order receipt not payment of order never left me."


  • The Java Handbook (this is here because of an excellent appendix covering the history of Java) by Patrick Naughton; "Great explanation of the early Java days"
  • Sunburst by Mark Hall and John Barry; "Fascinating. I'm still pissed we lost NEWS in favor of X11"
  • High Noon by Karen Southwick


  • Making the Cisco Connection by David Bunnell; "Sandy Lerner's post Cisco career has to be the best heel turn in the history of the industry"


Open Source


  • Piloting Palm by Butter and Pogue; "We forget how important Palm was"

Netscape / Internet Stuff

Web 1.0 - The Early Commercial Internet



Misc / Software

George Gilder

  • The Silicon Eye by George GIlder
  • Telecosm by George Gilder
  • Microcosm by George Gilder; "A fascinating look at the personalities that makes chips; his discussion of people that make analog devices specifically has always stuck with me"
  • Life After Google by George Gilder; "HAVE NOT READ"


  • Reinventing the Wheel by Kemper; "Sigh. Can't Kamen do something better; what has he been doing since???"

Blackberry & Nokia

Web 2.0 / Facebook / Twitter / Instagram / AirBnB / Etc


Multiple Companies Covered in One Book




  • No Filter by Sarah Frier; "Instagram is more important than we realize and this dives into the why"


The Cellphone Wars


  • Disclaimer: I'm not a gamer and there is a rich lore of game books that aren't here; send me recommendations on Twitter
  • Blood, Sweat and Pixels by Schreier; "HAVE NOT READ YET"
  • Lucky That Way by Fregger

Space 2.0 / Tesla