A.I., Uber & What’s Next in Tech: Q&A With Kayak Founder Paul English

Xconomy Boston — 

Technology can’t solve every problem. Sometimes engineers overlook human-driven solutions to the world’s biggest challenges.

That was one of the takeaways from my chat with Paul English at Xconomy’s recent business conference, IMPACT, held at the Museum of Science in Boston. The serial entrepreneur is best known as the co-founder and former chief technology officer of the travel search company Kayak, which went public in 2012 before Priceline acquired it for $1.8 billion.

English is now leading a new travel tech venture, Lola, which combines artificial intelligence technologies with travel agents—bringing back some of the human touch to the travel-planning process that got lost over the last decade with the rise of Kayak and its brethren. He’s also investing his money in several causes, including trying to improve the education system in Haiti.

English says he’s “guilty of having a lot of ideas”—he owns more than 200 Web domain names for potential businesses he’s dreamed up over the years—and he shared a lot of thoughts with our audience at the event. (He’s pictured above, on the right, with me.) Our wide-ranging conversation covered his philosophy on entrepreneurship, his opinion of Uber co-founder Travis Kalanick, his mixed feelings about artificial intelligence, and much more. Here are some of the highlights:

Xconomy: At this stage of your career, after building Kayak and several other companies, how do you think about the impact of your work, both with your companies and outside of them?

Paul English: It’s this progression of impact that I think about. First, is my team really happy and fired up, and then also what’s our mission, why are we here, what are we trying to change. In many cases, the thing you’re trying to change is, in itself, not that laudable from a social impact standpoint.

So, for example, my company Lola, we’re trying to revolutionize business travel, which is great for business travelers, but I don’t know how great that’s going to be for society as a whole. But I still think it’s OK to have a for-profit company that has a particular mission to help a particular set of people. I also think it’s important that the people who profit from such companies do things that are socially good, not just profit-good.

X: You’ve chosen a few causes that you like to give back to—from trying to solve homelessness in Boston, to tackling education and healthcare issues in Haiti. As an engineer, is it hard for you to see those problems and not find an easy solution through technology? What role can entrepreneurs and engineers play in solving some of those bigger problems?

PE: I think sometimes as engineers we’re guilty of looking at every problem as something that can be solved by a piece of software, a piece of hardware. And I’ve seen many, many cases in the work that I’ve done in Haiti, in Africa, in Boston, elsewhere, [where] we’re trying to do social good and technology is thrown at a problem.

A lot of times, as technologists, I want to make sure that we’re not ignoring human solutions, which sometimes can work better than technology. I always enjoy bringing MIT engineers to Haiti to show them what we’re working on. But I want to make sure that they don’t look at everything as a tech problem.

When I first decided to build schools in Haiti and help run schools in Haiti, I first toured existing schools—private schools, public schools, universities, a whole bunch of schools around the country. And I remember going to an elementary school … and they had smart boards at this school. … I remember thinking this is really silly because this classroom [has] no electricity, so I don’t know why someone sent a smart board here.

So, I think that the first thing I would encourage engineers is I want your ingenuity, but first try to think of: Are there humans who can help with the problem you’re trying to solve?

X: After Travis Kalanick resigned as Uber’s CEO, investor Bill Gurley tweeted that “very few entrepreneurs have had such a lasting impact on the world.” Do you agree with Bill’s tweet?

PE: I do. I think Travis, like most leaders, we all have things we’re good at, things we’re not so good at. Clearly, he built a world-changing company.

I think the reason I became disloyal to Uber and shifted over to Lyft was there’s just a litany of bad press and bad PR and bad events happening at the company. I think the thing that was the tipping point for me was the video of [Kalanick’s] road rage against one of his Uber drivers, and just the arrogance and treating his drivers like servants to him personally. And I didn’t think that was a cool way to run a company.

And in this case, I was really happy that there was an alternative that’s, I think, just as good, if not better. So, I’ve become a very happy Lyft user.

X: You actually had an idea that was basically Uber before Uber, called Snapcab. You thought about building it for Kayak, but ended up not doing it. Do you wish that you had? Where would Uber and Lyft be right now?

PE: Ideas are cheap; what matters is execution. And I’m guilty of having a lot of ideas. I [bought] Snapcab.com many, many years ago for the idea of getting a cab with a snap. I probably own over 200 domain names, each one of them a business idea of mine. But it’s worthless unless you pursue it.

At Kayak, we decided not to pursue that idea. We actually built a prototype for a piece of it. My co-founder at Kayak, Steve Hafner, one of his many, many strengths, he was phenomenal at laser focus—we’re just going to do this one thing. It caused us to abandon a lot of projects which we had ideas for. But the good news is when we did focus just on Kayak itself, we made that to be quite a successful company with a small team. And had we done some of the other things that we had started exploring, I’m not sure we would’ve been successful unless we had stopped everything else we were doing at Kayak and focused on that other idea.

X: Do you remember the ideas for all 200 of those domain names?

PE: I remember I had someone, an author, when he heard that I had this many domain names, was really surprised. He got someone to list them out and he sat down with me, and I think it took three hours to go through all 200 of them. He asked me for the plan for each one, and I will say I remembered most of them. But there were some that I would scratch my head and say, “I have no idea why I registered a domain called PurpleTicket.com.”

X: What’s your rating as a Lyft driver right now? [See why English first signed on as an Uber driver.—Eds.]

PE: I got approved for Lyft just recently. I haven’t started driving yet. I’m a happy Lyft passenger. My rating for Uber as a driver is 4.93 [out of 5]. Which sounds good, but I’m really devastated to know who didn’t give me five stars. I actually have a theory.

X: What’s the theory?

PE: I picked up these two guys from … Next Page »

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