Bob Cringely
(This book gets mentioned in Founders At Work... I think one of the Lycos guys had read it?)
Book -> Cringely -> Digitizing job -> VC -> VC -> funding or something like that.
Altho that tell-all on the Segway (Code Name Ginger) was pretty cool for all the flaws it pointed out.
Where the Wizards Stay Up Late was a book I did an interactive presentation on in 7th grade, so it always has a special place in my heart. In retrospect, it's not fun to read, but at the time, I devoured it. It's boring and nothing really happens, which really is a good metaphor for the most exciting technical change.
Ooh, and "The Dream Machine: J.C.R. Licklider and the Revolution That Made Computing Personal." Especially if you're into UI and unsung heroes.