
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.
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 Iāve also used a cruise travel agent, Wayland Travel for a safari, and, last year, American Expressā 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, āWhatās the best sushi restaurant in Tokyo?ā They gave us a really unique recommendation that I never would have discovered on my own.
How do you vet Lolaās 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, itās delegated to her. But if a question is too exotic for us, we advise our agents to be transparent. They might say, āI havenāt been there before, but I can do a ton of research for you.ā
You identify as an introvert. How did you learn to be extroverted for work? Do you have to flip a switch in your brain?
I have 50 people in my company. Sometimes itās comfortable for me to sit in front of my computer and do email and Slack all day. But if thatās literally all I do, itās sucking energy out of the room. People want to engage with me. I need to force myself to get up. Itās a lot easier to transmit energy face-to-face than to transmit it electronically. I always keep my calendar open for breakfast, lunch and dinner. So at the last minute, I can just grab a few people I havenāt seen in a while. Sometimes we have an agenda, but mostly itās just socializing, which is really important. Thereās efficiency to Slack and email, but without that human connection, it goes flat.
Much of your work goes back to this āhumanā element. At Kayak, you made your coders field phone calls for customer service issues. How come?
Weāre doing it at Lola as well. Only humans can have compassion. If you donāt put them on the line together, you build layers of buffers between customers and engineers: customer support managers, product managers, designers, quality assurance engineers, engineering managers ⦠By that point, the customer is so far removed from the engineer, the engineer has no compassion for the customer. By forcing the engineers to talk directly to the customers, they can design software to better address their problems.
What are some other lessons you learned at Kayak that helped you with Lola?
The most important thing any entrepreneur can do is focus on the team. When I interview people, there are two things I look for. One is their GSD — āget shit doneā — score. Do they have technical chops? The other 50 percent is: Are they energy amplifiers? Are they someone whom people enjoy being around? A lot of what I focused on at Kayak and what Iām focusing even more so on at Lola is playing the role of coach or organizational psychologist. I observe interactions, debug them and make sure weāre set up for success.
What is your debugging strategy?
If I have two people who donāt work well together and I just separate them, Iāve lost the ability for those people to give each other positive energy. So when something is dysfunctional, I talk to each person individually and then bring them together and say, āYouāre both extremely valued here, but youāre not clicking, and I want to know what we need to do.ā Sometimes itās just a matter of being open and naming a problem.
Thatās very hands-on. Many managers hate dealing with personnel issues. But you obviously see it differently: Without these one-on-ones working, the whole company wonāt work.
Yeah, and it wonāt work well. Iām not interested in running a āsuccessfulā company, Iām interested in running an exciting company where people love their job.
You once hired a guy whoād earned an Olympic medal in rowing. You said, āThis guy is hard-core, and I bet that translates.ā In that instance, you were right. Have you ever been wrong?
Iāve made the mistake of hiring someone whose style is so radically different from the team that it just didnāt work. So the trick there is, I want diversity of style, but not too much diversity. Thereās a fine line.
Youāve talked about having bipolar disorder and your own hypomania and OCD tendencies. Do you become fixated on prospective hires?
My friends call it my pedestal complex. When I meet somebody who has a skill I donāt have, I put them on a pedestal and worship them. And my friends are like, āOh, God, here he goes again.ā I probably fall a little in love with everyone, in some way. But Iāve seen this movie enough times to know how itās going to play out, so I try to manage my own expectations. Like, thereās a guy I just hired who is developing the user interface of the next version of Lola, and heās unbelievably strong. Iām trying to temper myself so I donāt focus too much on him, because what if he disappoints me, like, a month from now and heās not as fast a coder as I think he is? Iām attracted to shiny new objects.
In Tracy Kidderās new biography of you, A Truck Full of Money: One Manās Quest to Recover from Great Success, he explores the idea of whether your manic spells are responsible for your entrepreneurial confidence, or whether you succeed despite them. What do you think?
They definitely played a role. Thereās this romantic notion about the intersection of art and mental illness. But I do a lot of work with homelessness in Boston, and there are a lot of bipolar and schizophrenic people on the streets — and let me tell you, itās not very romantic. Mental illness can be very cruel. But if youāre just touched with some type of mental illness and it makes you look at the world differently than most people and you happen to be creative and/or bright, it can be a wonderful thing. My manic phases last weeks and sometimes months. I have enormous energy, I get by with little sleep, Iām always excited and Iām always excitable. I can lead a team when I have that kind of manic energy. So in that sense, itās useful.
Philanthropy has been important to you throughout your career. But a lot of entrepreneurs, especially those who are just getting started, pour every penny back into their business. At what point should people start thinking about others?
If I could have only one word on my tombstone, Iād want it to say ākindness.ā I want to be known as someone who cares about other people. Maybe I give to a particular 501(c)(3), or organize a group function at a food bank, or Iām kind to an old lady I meet on a bus. All of us need to be thinking about kindness. One, because itās the right thing to do, and two, if youāre kind and you care when other people are in pain, itās going to give you really good skills as an entrepreneur. Successful entrepreneurs invent services that make things easier for people.
Youāve taught classes on entrepreneurship at MIT and elsewhere. If your students learned just one thing from you, what would you want it to be?
If I had a class of 50 students and wanted to predict by the end of the semester which one would create a billion-dollar company, I think it would be the kid who can energize a team of five. So, my one lesson is: Can you energize a small team and lead them and listen to them and care about them and motivate them and get them to work out disagreements and get them unified in one direction? I believe that is a skill that can be learned.
Source: entrepreneur.com