Why the founder of Kayak took his Tesla and became an Uber driver

Paul EnglishPaul English dressed up as a vampire while driving for Uber.

On Halloween, Paul English dressed up as a vampire. Then he sat down behind the wheel of his $100,000 Tesla Model S and turned on the Uber app.

English didn’t become an Uber driver because he needs extra money. A decade ago, English co-founded the flight-finding website, Kayak. Priceline bought the site for around $2 billion two years ago, and since then, English opened a $20 million startup incubator in Boston and has been driving for Uber.

Like other tech billionaires, English found that being an Uber driver is a great way to do research for his new company, Lola.

With Lola, English wants to bring back the travel agent industry — an industry that Kayak helped kill — by making accessing a travel agent as easy as opening an app.

“Fast forward 10 years later, I’m trying to figure out how to reinvent the travel agency and make humans more valuable than the machines and where can humans help you get the perfect trip,” English said.

An executive assistant for everyone

He was initially going to build a competitor to Zirtual, the virtual assistant company that went bust overnight and laid off its 400 employees via email. But it was a tough business to be getting into, and his investors had a great idea: he should just focus on travel first.

“Just like in business travel, a lot of executives have executive assistants who book all their travel. And good executive assistants can be amazing in terms of simplifying your mind as a business traveller because they already know which airlines you prefer, what seating you prefer,” English said.

“We’re trying to make travel that simple. That you have this person in your corner who knows all your preferences and will do all the research and booking for you.”

That’s when English turned to Uber. He started driving a few months ago because he wanted to feel how it was like to be rated.

“In the app, you get to rate your travel agent on a scale of 1 to 5, just like you’d rate your Uber driver. I wanted to know what it felt like to get rated and how it changed the dynamic between Uber and the driver,” English told Business Insider.

It turns out he’s slightly less than perfect — he has a 4.95 out of 5 — but he has no idea what he did to deserve a lower rating.

“I think sometimes if you’re just kind and you talk to people, they appreciate it and you end up getting a good rating,” he said. “Probably because they like the car and hopefully they like talking to me.”

For now, Lola users will be able to rate their travel agent, but not the other way around. One of the most interesting things English has learned since driving for Uber is how many passengers the company boots off the system for unruly behaviour or a low rating.

He doesn’t have plans to let agents boot customers from Lola yet, but it’s not off the table either.

As for the travel agents, the first group will be based entirely in Boston and work full-time, so Lola’s engineers can sit next to a travel agent and figure out what can be built to help them.

English hopes that by treating its travel agents well, while keeping the rating system as a check, Lola can be as big as Kayak one day.

“Uber believes if you take care of your drivers, then ultimately they will provide take best care of their passengers. And we’re going to do something similar with travel agents,” English said. “We believe if we take great care of our travel agents, they will take best care of our travellers. “

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