Kayak Founder Sold Company for $2 Billion, Drove For Uber, Now What?

By on July 29, 2016 in ArticlesEntertainment

Paul English co-founded travel site Kayak in 2004. How he started the travel search engine is fairly interesting. He was visiting the venture capital firm General Catalyst as they had asked him to assess a company for them. While he was there, he had a chance meeting with one of Orbitz's founders Steve Hafner. An hour later, Hafner and English had decided to each put $1 million into a new company as equal partners. It seems hard to remember now, but back in 2004, there wasn't one single website that showed you all the options you have for flights, hotels, and rental cars. Sites like Expedia and Travelocity only served up listings that paid them a commission. English wanted his site to be more like Google, showing every single hotel on earth regardless of commissions.

He was the travel search engine's CTO. Kayak went public in July 2012. Four months later, it sold to Priceline for $2.1 billion. English made $100 million on the deal and was asked to stay on but opted not to. He had a fear that innovation would be slow at such a big company.

English didn't stay out of the game for long. Last year he founded another travel site called Lola. But before that he drove for Uber.

One day he looked at his calendar and realized that 90% of his interactions with other humans were with people in tech or nonprofits. So he decided to broaden his circle by driving for Uber, in his Tesla Model S, on Halloween, after he hosted a costume party. He drove from midnight to 2am. His customers thought it was hilarious that he was driving around dressed like a vampire in a Tesla. He kept a notebook and wrote down a sentence about every rider.

Driving for Uber helped English understand how people who work in the service industry are rated. English's personal Uber driver rating was 4.97. He wonders which customer didn't give him five stars.

And this all led to English founding another travel booking site. Unlike Kayak, which functions as a travel search engine serving up a multitude of choices, Lola features travel agents who create itineraries for customers. Those customers then rate their experience from one to five. He set Lola up this way to keep his agents competitive. Having ratings inspires people to get better at what they do. English isn't telling Lola's travel agents what the commissions are on the various hotel properties, so as not to influence them. Instead, agents get paid based on customer ratings.

Lola is based in Boston. It is currently in beta and has a waiting list of more than 5,000. The serviceĀ is currently free, but English plans to offer a paid subscription fee in the fall. It is expected that fee will be several hundred dollars.

Since this is the second travel site English has founded, it isn't a surprise that he loves to travel. He's booked seven trips so far with Lola and has another five coming up.

English didn't really have to work again after the Kayak sale, but not to do so wouldn't be in his nature. It actually runs in his family. His brother is also a serial entrepreneur. You might have heard of his most famous product. Ed English built the video game Frogger.

Did we make a mistake?
Submit a correction suggestion and help us fix it!
Submit a Correction