Maybe not perfect matches, but a few titles I'm familiar with that you might like:

Dreaming in Code - covers Mitch Kapor's post Lotus effort to build Chandler.

https://en.wikipedia.org/wiki/Dreaming_in_Code

Everyone Else Must Fail - all about Larry Ellison and Oracle

https://www.amazon.com/Everyone-Else-Must-Fail-Unvarnished/d...

Winners, Losers & Microsoft - title says it all

https://www.amazon.com/Winners-Losers-Microsoft-Competition-...

Two books by Bill Gates:

Business At The Speed of Thought

https://www.amazon.com/Business-Speed-Thought-Succeeding-Dig...

and

The Road Ahead

https://www.amazon.com/Road-Ahead-Completely-Up-Date/dp/0140...

Also:

MCI: Failure Is Not An Option

https://www.amazon.com/MCI-Failure-Invented-Competition-Tele...

Already mentioned, but I feel obligated to add another +1 for these three:

The Soul of a New Machine - Kidder

Hackers: Heroes of the Computer Revolution - Levy

The Idea Factory: Bell Labs and the Great Age of American Innovation - Gertner

Also, if you enjoy this kind of stuff, you might enjoy the AMC series Halt and Catch Fire. Yes it's fiction and highly dramatized, but it captures a lot of the spirit of the times from the beginnings of the PC era up through the Dot Com Bubble era.

The strength of path dependence and network effects in the economy is overrated, see the book "Winners, Losers, and Microsoft", http://www.amazon.com/Winners-Losers-Microsoft-Stan-Liebowit... , for a pretty thorough discussion.

Better can be enough, if it's ENOUGH better. The rule of thumb is that something has to be at least twice as good to replace a similar but already functioning system (the real costs of retraining and lost productivity during the changeover can almost never be accurately calculated, that's why there is the rule of thumb). For an academic view, see "The Fable of the Keys" http://www.utdallas.edu/~liebowit/keys1.html about qwerty vs Dvorak; and the version that was expanded into a book about Dvorak, Microsoft, and the internet http://www.amazon.com/Winners-Losers-Microsoft-Stan-Liebowit... .

ADDED: And Christensen in "Innovator's Dilemma" http://www.amazon.com/Innovators-Dilemma-Revolutionary-Busin... shows how slight improvements can gradually replace something that was originally better.