Funny, reading that, made me think of Bill Gates' book, Business at the Speed of Thought: https://www.amazon.com/Business-Speed-Thought-Succeeding-Dig...

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.

FWIW, there's already a thread on this topic:

http://news.ycombinator.com/item?id=2026716

But to answer the question: I started out with a goal of integrating Apache Shindig[1] into Quoddy[2] to enable OpenSocial[3] support. A very basic version of that is up and working, so now I'm working on refining the account / profile "stuff" in Quoddy and factoring out some common code for use in another project[4].

I'm also trying to get in a fair bit of reading. I had started Googled[5] before the break, and I finished that earlier today. I'd also started Simply Complexity[6], which I finished sometime in the last 24 hours or so (time is starting to become a fuzzy concept to me here). Then I read The Facebook Effect[7] which I just finished up a few minutes ago, and now I'm starting to re-read Bill Gates' Business @ The Speed of Thought[8]. Once I finish that, I'm hoping to find time to squeeze in The Art of Enterprise Information Architecture[9] and - if things go smashingly well - Complexity - A Guided Tour[10].

1: http://shindig.apache.org

2: https://github.com/fogbeam/Quoddy

3: http://www.opensocial.org

4: https://github.com/fogbeam/Neddick

5: http://www.amazon.com/Googled-End-World-As-Know/dp/014311804...

6: http://www.amazon.com/Simply-Complexity-Clear-Guide-Theory/d...

7: http://www.amazon.com/Facebook-Effect-Inside-Company-Connect...

8: http://www.amazon.com/Business-Speed-Thought-Succeeding-Digi...

9: http://www.amazon.com/Art-Enterprise-Information-Architectur...

10: http://www.amazon.com/Complexity-Guided-Tour-Melanie-Mitchel...