This book is partially a biography of Paul English and partially the story of the companies he founded, including Kayak.com. One way in which this differs from many accounts of contemporary startup success is that it takes place almost entirely in Boston instead of Silicon Valley. This is partially due to the author’s familiarity with the area and its computing industry from his previous book, The Soul of a New Machine.
This raises the question of why Boston fell behind Silicon Valley as the center of software entrepreneurship. One key reason was that California does not enforce noncompete agreements, while Massachusetts does. This makes it easier for employees in California to move between companies or start their own. This plays into the book as well, when one of Paul’s early employees rejects a strict noncompete agreement.
The title comes from a saying of one of Paul’s early associates: “one day that kid is going to get hit by a truck full of money, and I want to be standing beside him when it happens.” English acknowledges that he has been “obscenely lucky” both in business (he sold one startup at the peak of the Dot-Com bubble) and in life (he was originally booked on one of the flights from Logan that flew into the World Trade Center on September 11, 2011, but rebooked to a cheaper option).