Something fun happened today. A reader reached out who had been digging through my early-2000s and 2010s posts trying to understand the history of the software industry. That immediately got my attention because I love people who study history. It’s the best way to understand the present. And a great way to avoid repeating the mistakes of those who preceded you.
So I’m always happy when someone wants to talk about software history.
His specific request was interesting: he was looking for case studies or books that were popular at the time — something that would help him understand how people in the industry were thinking back then.
I decided to do him one better. In my view, the real canon of books that shaped enterprise software thinking was largely written before 2000. So I assembled the following reading list: a set of 1990s-era books on software, strategy, marketing, and the industry itself that many of us were reading while the enterprise software industry was taking shape.
Think of it as a reading-list stroll down software, and Silicon Valley, memory lane.
1990s Era Tech Marketing and Strategy Books
High-Tech Marketing
- Marketing High Technology — William Davidow (1986)
- Crossing the Chasm — Geoffrey Moore (1991)
- The Gorilla Game — Geoffrey Moore, Paul Johnson & Tom Kippola (1998)
- The Regis Touch — Regis McKenna (1985)
Positioning / Marketing Foundations
- Positioning: The Battle for Your Mind — Al Ries & Jack Trout (1981)
- The 22 Immutable Laws of Marketing — Al Ries & Jack Trout (1993)
- Ogilvy on Advertising — David Ogilvy (1983)
Technology Strategy / Innovation
- The Innovator’s Dilemma — Clayton Christensen (1997)
- Competing for the Future — Gary Hamel & C. K. Prahalad (1994)
- Only the Paranoid Survive — Andrew Grove (1996)
- The Discipline of Market Leaders — Michael Treacy & Fred Wiersema (1995)
Product Marketing Culture
- The Macintosh Way — Guy Kawasaki (1990)
Enterprise Sales / Go-to-Market
- SPIN Selling — Neil Rackham (1988)
- Solution Selling — Michael Bosworth (1995)
Economics of Software / Networks
- Information Rules — Carl Shapiro & Hal Varian (1998)
Enterprise Technology Industry Case Studies
- Softwar: An Intimate Portrait of Larry Ellison and Oracle — Matthew Symonds (2003)
- The Ingres Papers: Anatomy of a Relational Database System — Michael Stonebraker et al (1985). Technical background on Ingres that provides useful context prior to reading Softwar.
- The New New Thing — Michael Lewis (1999)
- Hard Drive: Bill Gates and the Making of the Microsoft Empire — James Wallace & Jim Erickson (1992)
- Accidental Empires — Robert X. Cringely (1992)
Software Engineering
- The Mythical Man-Month — Frederick P. Brooks Jr. (1975)
Classical Strategy
- The Art of War — Sun Tzu


I know this risks muddying the waters, but it seems to me that the business context of the time had a role, i.e. the big books that the customers were reading — Michael Hammer and Reengineering the Corporation (actually a good reread with AI process rethinking in mind — “don’t pave the cow path”!), and Good to Great by Jim Collins jump to mind? (even if the latter did get solidly debunked by later results!)
True and thanks for adding. Re-engineering and Y2K arguably built SAP after all. And Good to Great was a fun disappointment but I do omit it because of the debunking issue (other than that, Ms. Lincoln, …)
I have a feeling Dave just looked at his bookshelf and/or the required reading list of Business Objects marketing in that era. Speaking of which, what about this one:
e-Business Intelligence: Turning Information into Knowledge into Profit
Nice add!
Can I request you to compile a reading list for today’s age?
I’ve read some of these – loved Hard Drive