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

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a Middle Eastern country, and they told me where they were from. I asked them how they liked Boston. Um, I’m just trying to think if I can say this. They said they like Boston, but all the women are “bitches.” And I said, “Really, all the women?” They said yeah. I said, “You know, if it’s all the women, it might not be the women’s problem.” I don’t think they gave me five stars.

X: What are some ways that driverless cars will change society, besides the obvious and immediate changes?

PE: The thing that I’m most excited about is what it’s going to mean for people who are elderly or disabled or blind, that they’ll have mobility that they [didn’t] have before. When my mom passed away, I became the primary caretaker for my dad, who had early-stage Alzheimer’s. I remember the time I had to take his keys away. He was very early in dementia, but I thought it was a safety issue. My dad was a car guy, and that was really brutal for me to take his keys away and not let him drive. I remember just thinking, it would’ve been awesome if somehow he could drive but have his mild dementia not be a barrier to it.

I have a sibling right now who has a brain injury and has stopped driving. It’d be amazing if he could get around anywhere. My brother—and I have a neighbor who is 91 that I look after—and they do both enjoy Lyft to get them around. But I am excited that self-driving will make it even more accessible [and] more affordable.

I worry about the flip-side of that, when there’s self-driving trucks. I think there are about 3 million truck drivers in the U.S. And driverless [technology] is coming to trucks. There are a lot of people working on it. And in some ways, it’s easier to do a driverless truck than a driverless car, particularly for interstate [highways]. But that’s going to cause a lot of turmoil from a jobs standpoint. We’ve got to figure out what to do there.

X: Does that concern you, that automation potential?

PE: It does. I’m in the camp of people that are both incredibly excited about A.I., but I’m also a little worried about it. Everyone has seen Bill Gates’s proposal to tax robots so that if people raise capital to build something that automates a process and gets rid of human jobs, that somehow that tax … can be used for retraining. I’m not sure if the economics of that will work or not.

There are certainly jobs that I think computers will never be able to do—some jobs around education, healthcare, elder care. And maybe for the jobs that are really excellent at being served by humans, we should teach it to a lot more humans to provide really phenomenal healthcare, elder care, etc. But I do worry about people being automated out of jobs. I think it’s something that we should talk a lot about.

X: Any potential solutions there?

PE: I think retraining is critical. I think it was funny with the last election—and I can’t believe I just brought this topic up because don’t get me started—but the whole thing about coal miners and retraining and concern for the coal miners. And not that I’m not concerned for the coal miners, but I think it’s somewhat of a romantic notion that there’s this industry which is dying and should die, and somehow we can’t kill it because we’re worried about a small set of people. In the case of coal miners, it really is a small set of people.

I think retraining is important. Retraining in some cases to use and take care of A.I., take advantage of A.I. and new tech; in other cases, retraining to do jobs that computers can’t do.

X: Let’s do some rapid-fire questions. I’ll say a word or phrase, and you say the first word that pops into your head.

Let’s start with artificial intelligence.

PE: Breathtaking.

X: Smartphone.

PE: Needs A.I.

X: Amazon.

PE: Extraordinary.

X: Tesla.

PE: World-changing.

X: Ford.

PE: I want them to succeed—hopeful.

X: Kayak.

PE: Optimization stage.

X: Donald Trump.

PE: Next question.

X: Venture capitalist.

PE: I don’t know if I can answer this in one word. I’ll say VCs, I think, have a bad rap for all the entrepreneurs who don’t get funded. But, much like the guys in my Uber that night, sometimes you don’t get funded, it’s not the [fault of the] 20 VCs that turned you down. I think there’s some great VCs in Boston. So, I don’t have a one-word answer.

X: Customer.

PE: Purpose. It’s the reason why companies exist. It’s what the focus should be.

X: Entrepreneur.

PE: Risk-taker.

X: Engineer.

PE: Problem solver.

X: Boston tech.

PE: Thriving.

X: What’s your boldest prediction about new technology in the next 10 to 20 years?

PE: The coolest thing I’ve seen in the last week is I just watched the entire Google I/O conference, and I found the advancement of deep learning at Google has been really breathtaking. And it’s getting better faster than I think anyone at Google expected it to be—Google and other companies.

I thought it was extraordinary how many data scientists Amazon hired to work with the Alexa voice project. Amazon had a vision for that really early on, prior to anyone else.

But the biggest applications I see of deep learning [are] going to be computer vision and computer voice and live translation. Things that were sci-fi a few years ago are now actually happening.

And I think it’s going to change how we use computers. I think smartphones will be not as important because you won’t be typing on glass. You’ll just be talking. I really, really believe it’s going to happen.

X: What’s after voice?

PE: Thoughts.

[Above photo by Keith Spiro Photography.]

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