Silicon Valley Failures

I'm starting with one of my absolute favorite books about startups — I distinctly remember checking out boo.com (a site to sell high fashion) soon after it launched and thinking "wow, this is one of the worst web sites I've ever seen." Well, wait until you read the story of the narcissistic founders, the insane amount of money they burned through, the crazy parties... it's really beyond belief. A terrific snapshot of the absolute peak of the Internet bubble.

The Newton was burdened from the start: saddled with poor battery life, a high price, and (most notoriously) wildly inaccurate handwriting recognition, it's remembered mostly as a giant flop. But when you look past the surface, the story of the Newton's creation is actually quite remarkable, and this book does a great job showing the enormous technological hurdles surmounted to create the first true popular hand-held computer. (And you know what? I owned one, and the handwriting recognition wasn't as bad as everyone thought. :-)

This terrific story of the rise and fall of Go Computing is one of the best technology books I've ever read. Go was devoted to making the first pen-based tablet computer (before the Palm Pilot and Treo) and Kaplan tells the story with verve and style. The scene in the boardroom, where he throws down a legal pad and helps the room of VCs imagine that it be the computer itself, is mesmerizing, and captures the essence of how startups create a vision — and try to translate that pie-in-the-sky vision into a tangible product. A real page-turner.

This book is the story of a company that created a piece of software to build web pages which was subsequently acquired by Microsoft and renamed "FrontPage." (Perhaps you've heard of it...) What I like about this novel is its total lack of restraint; the author isn't afraid to really tell it like it is and "name names." Fun gossip about some of the most famous technology people and companies mixed with good business startup story.

This is Michael Wolff's personal story about getting swept up in the Internet revolution and his quest to make business happen in a world of half-baked ideas and way, way, way too much money being thrown around. I remember those days well, and how nearly every week brought up a big business deal that often didn't seem to make a lot of sense. (The PR spin on some of these deals was always good for a laugh!) Wolff helps place you in the middle of the action by describing some of the other major events of the time such as the founding of Wired magazine, and lots and lots of deals with America Online (remember them?).

A terrifically-written personal story about a Boston Globe reporter throwing out his old career to plunge himself into the world of the Silicon Valley entrepreneur, replete with a new business partner, VCs, crazy launch parties, last-minute money problems and an easy-to-remember dot-com brand. Really pulls you in.

For anyone who remembers the old web site F-d Company (written by the irascible "Pud"), you probably know what to expect from this book: the same explicit language and spot-on analysis of some of the dumbest moves of the dot-com heyday. If you never saw that site, you're in for a treat. Massive displays of stupidity are held up to the light for ridicule and hilarity.

Finally, I'm including this strange, silly little book — it's not about the company Pets.com, per se; it's a series of photos of the (famous!) puppet with witty captions. Though the company failed, the sock puppet ad campaign was a stroke of marketing brilliance, and this book is a testament to the campaign's wit and fun, as well as a perfect memento of the go-go Internet bubble of the late '90s.