The Soul of an Entrepreneur


You won’t learn a great deal about how to start a company, how to raise money or how to go public (a subject totally missing from Tracy Kidder‘s new book A Truck Full of Money: One Man’s Quest to Recover from Great Success).  But Kidder’s a great writer  with a real eye for telling detail and an ear for dialog.  I remember being totally immersed in his earlier work The Soul of a New Machine years ago.

Unlike Soul, which was all about hardware engineering, Truck Full is all about software and ecommerce and a software engineer, Paul English, who hit it very big by selling his startup, Kayak, for almost two billion dollars.

The book’s a bit of a pastiche of stories of Paul English’s life and times, sometimes seeming like a cut and paste job from Kidder’s three years of following English around. But it’s packed with fascinating portraits as well as an engrossing look at what it’s like to struggle with bipolar disorder.

I did have the experience of meeting both Kidder and English a few years ago when Kidder was just beginning the process of following English. We pitched English on investing in PopSleuth and our arts and entertainment app, Endorfyn. Tracy Kidder sat in on the whole meeting. English wasn’t interested in investing, though he had some useful general advice about the business.

However, he did seem interested in hiring our CTO, Andreas Randow. But that interest wasn’t reciprocated.

So if you’re more interested in biography, Greater Boston’s tech scene and psychological matters than the nuts and bolts of building businesses, this a great read. I finished it in one sitting. Just don’t expect a manual on how you too can build a unicorn company, go public, and cash out for millions of dollars.

I’d still like to know why Kidder totally skipped over Kayak’s IPO process in favor of expending so much ink on its sale to Priceline.

Author: Mentorphile

Mentor, coach, and advisor to entrepreneurs, small businesses, and non-profit organizations. General manager with significant experience in both for-profit and non-profit organizations. Focus on media and information. On founding team of four venture-backed companies. Currently Chairman of Popsleuth, Inc., maker of the Endorfyn app for keeping fans updated on new stuff from their favorite artists.

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