A Puzzling 'A Truck Full of Money' from Tracy Kidder

Please disagree with this critical review.

September 27, 2016

A Truck Full of Money: One Man's Quest to Recover from Great Success by Tracy Kidder

Published in September of 2016

The fall book that I was perhaps most excited about is Tracy Kidder’s A Truck Full of Money.  I read Kidder’s The Soul of a New Machine when I was in 8th grade - and I credit this book as one that influenced me to pursue a career in and around technology.

A Truck Full of Money tells the story Paul English, a lifetime Boston resident and co-founder of Kayak.com.  The “truck full of money” in the title refers to $1.8 billion dollars that Priceline paid for Kayak in 2012.

This should be a great story.  Kayak is an incredible technology company success story.  Paul English is a colorful entrepreneur and technologist.  The Boston technology world has been under-explored in comparison to the Bay Area tech scene.

The puzzle of A Truck Full of Money is that Kidder never dives deeply into the world of Kayak, or that of technology startups.  We learn very little about online travel space.  We get almost no glimpse into the technical and business challenges of building and running Kayak.  Nor do we gain much insight into the role of technology - or the technology business - in our larger culture.

The descriptions Kayak’s technology are desultory and simplistic.  Surely there is a great story in big data challenges of finding optimum travel routes.  The role that technology has played in blowing up the travel industry surely has connections to how other industries have been disrupted - I’m thinking education and journalism - but these connections and lessons go unexplored.

Ultimately, Kidder seems to be more interested in the psychology of Paul English than in telling a story about how the technology industry has changed over the past 40 years.  The problem is that as interesting as Paul English may be - and he is quite a character - it is never clear as to why knowing his story is important for knowing anything about anything bigger.

It may be that telling a business story about how technology changed the travel industry - or a technology story about the challenges in building a site like Kayak - were simply too big for an outsider like Kidder.  While reading A Truck Full of Money I kept wishing that Kidder had spent less time talking to English, and more time talking to everyone else about how the technology industry is changing.

Perhaps Kidder came to the story too late - and it was not possible to reconstruct the business and technical story of Kayak.  In that case, I wish that Kidder had taken some more time - and followed English’s new company Lola - a startup that seeks to bring back the classic services of a travel agent through an app.

This pains me to write this review - as I’m such a huge fan of Kidder.

Perhaps my expectations for a book about technology - and the business of technology - were unfair?

Would you be willing to give A Truck Full of Money a Chance, and argue with me about this review?

What are you reading?

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Joshua Kim

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