Building A Billion Dollar Team Image Credit: Entrepreneur
Building A Billion Dollar Team Image Credit: Entrepreneur

Building A Billion Dollar Team

Paul English sold Kayak to Priceline in 2012 for $1.8 billion. Now he is reentering the industry with Lola, a mobile app that combines AI with human travel agents to plan and book trips. And at both companies, he says, the key to success is the people he hires.

Ashlea Halpern

By texting with Lola agents, users can book hotels and flights, get restaurant recommendations, and get help with itinerary planning. Were you a fan of travel agents back in the day? 

Really back in the day, I used AAA. But I’ve also used a cruise travel agent, Wayland Travel for a safari, and, last year, American Express’ concierge service in Japan. The trip to Tokyo was motivated by the documentary Jiro Dreams of Sushi. I was obsessed with it—not because of the sushi, but because of this whole idea of what happens when a human being commits their life to perfection. Immediately after seeing the film, I got a couple of friends to go with me. One said she could get us a reservation at Sukiyabashi Jiro. Guaranteed. But at the last minute, her attempt fell through. So I called American Express and asked, “What’s the best sushi restaurant in Tokyo?” They gave us a really unique recommendation that I never would have discovered on my own.

How do you vet Lola’s agents for that level of knowledge?

We have one woman who has been to every island in the Caribbean. When we get a Caribbean question, it’s delegated to her. But if a question is too exotic for us, we advise our agents to be transparent. They might say, “I haven’t been there before, but I can do a ton of research for you.”

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