#27 A Truck Full of Money: Coding, Mania, Love, Genius: The Life of an American Entrepreneur

Early Ventures

Paul English's entrepreneurial journey began with a unique blend of ambition and unconventional methods. As a seventh grader, he demonstrated his business acumen by turning a small investment from his paper route into a profitable venture selling marijuana, showcasing his early knack for entrepreneurship 1. This drive continued into his adulthood, where he founded multiple companies, including Kayak, a travel search engine that became a significant success 2. Despite his achievements, Paul often grappled with the guilt of success, stemming from his upbringing in a large family where no one was meant to stand out 3.

Someday this boy is going to get hit by a truck full of money, and I'm going to be standing beside him.

--- David Senra

His story is a testament to the complex interplay between personal values and professional success.

   

Kayak's Success

Kayak's success story is a remarkable example of innovation and strategic business acumen. Founded by Paul English and Steve Hafner, Kayak revolutionized the travel industry by serving as a comprehensive search engine for flights, hotels, and rental cars, akin to a Google for travel 4. The company's unique revenue model, which involved earning fees from referrals to airlines and hotels, allowed it to generate significant profits with a lean team of just 205 employees 5.

In 2012, Kayak's revenues came to nearly $1.5 million per employee, one of the highest ratios among all publicly traded companies.

--- David Senra

This efficiency and profitability culminated in a $1.8 billion acquisition by Priceline, marking a high point in Paul's entrepreneurial career.

   

Startup Ventures

Paul English's career is marked by a series of startup ventures, each contributing to his growth as an entrepreneur. Despite facing numerous failures, such as the unsuccessful Netcentric and a software company aimed at creating internet-connected jukeboxes, Paul persisted in his pursuits 6. His resilience paid off with the founding of Boston Light Software, a company that capitalized on the dot-com boom by creating a platform for building websites 7.

It's not about your batting percentage or slugging percentage, but basically one or two successful ideas can pay for a lifetime of other failures.

--- David Senra

These experiences highlight the iterative nature of entrepreneurship, where each venture, successful or not, builds towards future achievements.