Skift Take
Travel startups take a dramatically different idea, creativity, exuberance, focus, money, connections, a dedication to team building, and a helluva lot of hubris. Depending on the moment, Kayak and Lola co-founder Paul English has all of the above in ever-changing quantities.
Paul English met his soon-to-be Kayak co-founder Steve Hafner in December 2003 almost by chance in the offices of General Catalyst in Cambridge, Massachusetts. Over a 45-minute lunch at nearby Legal Sea Foods, they agreed to go 50-50 on the Kayak travel-search engine while each of them chipped in $1 million of their own money to have skin in the game.
English, a coder and entrepreneur by trade who had hacked his grade-school computer teacher's password years earlier to get access to more commands on his "dumb terminal," turned his $1 million Kayak investment into $120 million when the Priceline Group acquired Kayak for $2.1 billion a decade later in 2013.
Paul English, and the CEOs of TripAdvisor, Expedia, Booking.com, and More Are Speaking at Skift Global Forum 2016. Join Us.
A new biography of English, A Truck Full of Money: One Man's Quest To Recover from Great Success (Random House), written by Tracy Kidder, details this meeting of then-soon-to-be Kayak co-founders, and provides a fascinating glimpse into the rigors of software coders, entrepreneurs, venture capitalists, team-builders, recruiters, and sometimes-slightly-mad creative types.
The takeaways about love, life and business — pimples and all — for people involved in all facets of the travel industry and elsewhere are nearly ever-present in the book, including at the food and drink fest at Legal Sea Foods that led to the creation of Kayak.
It's Not Just About Having A Good Idea
Unlike Kidder, the book's author, English did not graduate from Harvard but attended commuter school UMASS Boston in Dorchester starting in 1982 after graduating high school at the lower rungs of Boston Latin, and he thought en route to night classes in college that he probably was going to become a musician.
Nearly a professional lifetime later, by 2003, English was an entrepreneur in residence at venture capital firm Greylock, and visited General Catalyst's offices that day of the Hafner meeting to offer feedback on an investment that General Catalyst was pondering.
English, as the book explains, was introduced to Hafner and told him over lunch that he would help Hafner find a chief technology officer for Kayak until Hafner convinced English to co-found the startup with him. The book notes that Joel Cutler of General Catalyst, which had already committed $5 million to the venture, and Hafner, who was a Cutler friend and on the founding team of Orbitz out of Boston Consulting Group, had come up
