KAYAK: Paul English

Hey everyone, a quick thing before we start the show. How I built this is doing its annual survey to better understand our listeners and how you use podcasts. So please, please, please help us out by completing a short anonymous survey at npr.org slash built survey. That's all one word, npr.org slash built. Built survey. We'd really appreciate your feedback. We really do need it. So again, npr.org slash built survey. And thanks. We hired a top brand agency in New York City named Wolf Owens.

The branding project was led by a woman named Carol Costello. Ultimately her team came up with a list of about a hundred names. And Kayak was actually our second choice.

Alright, so you've butt kayak and Did anybody like get on there initially and say, Where are the kayaks? Like Where's your kayak gear? Like what are you doing? We literally got hate mail from kayakers. Yeah, from Kyakers, yeah.

Who said this was terrible that we took this over and this is like a blight on the internet, you know, that someone would take over their precious hobby. Yeah. And use it for something dirty like a travel site. It's how I built this. a show about innovators, entrepreneurs, idealists, and the stories behind the movements they built.

Guy Raz and on the show today, how a totally chance meeting in a Boston restaurant. Led Paul English to launch his fifth business. Kayak. And how he and his partner grew it into a popular travel site. Then sold it.

For nearly two billion dollars. Starting a business is full of pain and frustration. No matter which path you take There will always be an obstacle. Something trying to prevent you from solving the problem.

And then A new problem will crop up. A supplier who can't fill your order until after Christmas. A letter from a state or local agency that hasn't received your permit application, even though you filed it months ago. A distributor who forgot to put your product on the store shelves.

All of these things and many more Are usually reliable sources of high blood pressure. But there's a certain type of person who thrives on these challenges. Someone who is almost addicted to the stresses of starting again and again and again. And that person Is a serial entrepreneur.

For them. The money side of business is almost an afterthought. It's the process side that makes them feel alive. And we've seen that on this show in entrepreneurs like Richard Branson and Mark Cubin and Marcia Kilgore. Founders who every two or three years pretty much have to start a new business to stay fulfilled and energized. And all of this goes for Paul English as well.

The co-founder of the travel website Kayak, and seven other companies, plus three philanthropic organizations, and several other side projects. Back in two thousand four, when Paul launched Kayak along with Steve Hafner, He had already founded or co founded at least four successful companies. And yes, the concept behind kayak, a clean and simple search engine for plane tickets and later hotels and car rentals. All of that was appealing to Paul at the time, but as you'll hear,

What really appealed to him was the sheer joy of looking at another empty whiteboard and filling it with the building blocks of yet another brand. Which eight years after launch? Wound up selling the price line. For one point eight billion dollars. And you might think that somebody with the incredible drive and instincts to build eight companies

might come from an entrepreneurial background, but No, not really. Paul grew up in a working class family in an Irish, Catholic, and Italian neighborhood south of Boston. There were seven kids in this family, and they all shared a cramped

Yeah, the brothers the four boys l slept in the attic, which had no heat and no air conditioning. I mean the worst part of it was we had one bathroom with nine people. Wow. And so we each had a fifteen minute slot starting at like five AM or something. And if you missed your slot, you'd be going to high school smelly, so That was that was tough getting up at five thirty AM or whatever the time was. But It was fine, like we didn't know anything different.

And I never felt like my house was crowded. It's just that it is what it was. And um that's how we grew up. Wha what was your what did your dad do? For a living. My dad was a pipe fitter. He worked for the same company for forty nine years. And he really ran the household.

And probably all of us were like just a little bit afraid of him. Maybe probably more so Dan and I than the others. My brother Dan and I were the ones who acted out probably more than the others. Was he physic? It's interesting. I have this one story about my dad. He wasn't Like a huge

Probably a little bit thin as I remember. And there's this one scene where I had gotten a fight with someone, a kid down the street. And His father

Came over to our house and banged on the door. I remember him bang, bang, bang and my father opens the door and there's this huge guy And he said, Your son, beat up my son and blah blah blah blah. And my father put his finger on the guy's chest and said, Don't you ever Bang on my door again.

And somehow the way my father communicated it to people, this guy melted. And I remember watching my dad do that and saying, How does he do that? My dad had really good influence and skills, he was very charismatic and very confident. Um, your your mom, I guess, was was a teacher. and a social worker, but um

From what I read. She spent like the first ten years of of your life actually sick. Um I mean d do you remember Being aware of that and and And cognizant of her being ill?

Yeah, my mom had an illness called myosina gravis, which is a debilitating muscle disorder. And she spent much of the first ten years of my life in bed. But My mom had a miraculous recovery. Back when I was about ten.

That she was healed by a Catholic faith healer and My mother was very religious. I'm not. If anything I might consider myself Buddhist because

I read a lot of Buddhism and I'm very interested in following a few Buddhist teachers. But I'm not sure. That this priest healed her.

Or Her belief in the priest healed her. Yeah. And I think there is this magical thing that can happen when someone really, really believes something. They can will it to happen and they can will their brain to rewire. And something happened to my mom that day and she started healing. It wasn't a night and day switch.

But she started fighting the disease. And my mom even started jogging back before jogging was a thing. Yeah. She started playing tennis. She became very strong at the end of her life. So I think the doctors told her she could never get rid of the disease, but somehow She fought it. And it seems like she won.

It's amazing. What do you remember about your parents' marriage? Well What was it like? It was Difficult

During The seventies and eighties at the end of their lives. My father ended up passing away two thousand and three, so it's been almost twenty years. since both my parents passed away. But

I'll tell you kind of a funny scene. Literally on my mother's deathbed. With her seven children around her. This is Kind of a sad thing to hear, but She looked around.

The room. In each one of us. And I can't believe she said this, but she said All my life. I knew my marriage to your father was a mistake.

However. I look around the room. I look at each one of you. And then she paused and she looked at each one of us. And she said, I can see what each one of you got from him.

And what you got from me. And I know now that my marriage was very successful. Wow. Yeah. They were very different people. My mom was an intellect

She grew up in a very difficult childhood. And my dad was Kinda happy go lucky he didn't go to college. He was very charming, he was a good storyteller, but they were very, very different. Uh the last after my dad retired, I think they actually had

A lot of nice time together. Did you go to Mass every Sunday? Did your mom We did. We sure did. Did she make you go or She made us go. Were you an ultra boy? I was. Which my teachers my teachers didn't believe me. After I'd many times I get, you know, set up to go to detention after school because I was a bit of a Wise guy in school, I was bored.

And I would get in trouble And many times did they have to go to detention. I said, I can't, I'm gonna ultimately have to go to church and they wouldn't believe me. Yeah, the classroom was not a good place for me. I guess today you would say I had eighty H D maybe, I'm not quite sure, but I'm still amazed. I think about

If there was an anthropologist from another culture who beamed down you know, to my schools in Boston or really any school and saw that they kept thirty kids in desks for eight hours, it just seems inhuman. Like who came up with this idea? to to make kids sit in a chair at a desk for eight hours. It just seems crazy. Yeah.

And um I couldn't do it. I struggled with that. I did like performing intellectually and so I worked really hard. at music and science, things like that, but my grades were terrible. But but clearly

Uh, y I mean you were very intelligent. Because you wound up going to Boston Latin and Uh, for people to don't know this is I think it's like the oldest high school in the US and there was an exam or may still be uh to get into it. And from what I've read about you, you were like one of the you had like one of the highest admission scores to Boston Latin Uh

Thousands of kids who took the test. Yeah, the way I looked at it was I tested well. I felt like I had this trick. That in classes. I was fast on exams and I could guess things really quickly. But um

I don't know, I guess I would say I had a lot of diverse interests as a student. I won prizes in All right. And science and music and math and

I was a very competitive kid growing up. with all those siblings in one house, I think it makes you both collaborative but also competitive. Yeah,'cause you're you're competing for your parents' attention. Yeah, that's probably I mean, I I don't know if I was thinking about that explicitly as a kid, but that's probably true.

I mean this is the late seventies, early eighties. Do you remember when you first got Exposure to A computer'cause I'm assuming you couldn't afford to have one at home. Well

To my surprise and the surprise of my siblings One year. My mother went out and bought a computer called a Commodore Vic twenty. I think it was three hundred dollars, which is a tremendous amount of money back then. Yeah. And we were shocked that she would spend that money on the computer and I still don't know why she bought it. When she she must have seen an ad somewhere and thought this could be a good way to entertain the kids.

And I kinda selfishly took it over. And I learned everything I could. I learned how to code. I wrote Software. I wrote a video game and

That to me taught me like Whoa there's way to make money programming. And that was pretty cool. And and I guess it was around this time that you actually built a A video game. Which would become

Mm. But like your very first company, I guess. Yeah, I um So I called my little company Speed Games. It's funny to call it a company, because I don't think I was incorporated, but the f game that I sold was called Cupid.

And It operated maybe a little bit like a Pac-Man, but There was a player that would race across the field, Cupid's arrows would shoot, you had to avoid the arrows. And then my most proud thing about the game was I designed all the music And

sound effects and all the graphics and I really put A lot of energy. into what happened when Cupid's arrow would hit you, like what happened to your shape. So this game that you wrote Cupid.

You managed to get the attention of a I guess a a a company called GBA. Which you you sold a license to f t to them, or something like that? Yeah, the deal was it was twenty five thousand dollars up front and then a dollar revenue per game cartridge. Which sounds really great, especially for a teenager.

The bad news is I license the game to them. And they immediately went out of business. And then the question is Why didn't I then go contact every other game publisher to try to find someone else to license it. But

Like a lot of things, I would jump from thing to thing and I felt like I had mastered the game and then I was on to something else. So I wasn't really motivated by money. The money was very cool as a teenager getting a big check. But um I went on to the next thing. Did they pay you? I mean they went under did you get all the twenty five pay. No, they paid me five thousand up front. But then they immediately went out of business. So they never even sent me The rest of the twenty five thousand. So all I really made out of it was five thousand.

In nineteen eighty two. Nineteen or whatever. There was a l there was a lot of money a lot of money. Yeah. It's a ton of money, especially for a high school kid, my God. So for college you uh you end up going to the University of Massachusetts. uh in Boston. And I guess it it became pretty clear while you were there that you were

gonna pursue a career in in computers pr probably as a programmer something like that, because you you really I think while you were in college you you already started to do some freelance work for like the the the sort of the nascent computer industry that started to grow in and and around in in the Boston area in the early eighties. I don't remember how I got my first job, but

I worked mostly full time during college. It took me five years to get my bachelor's degree and another two years to get my master's. But I did everything from I work for a mini computer company called Data General in an operations research group. I work for the US Air Force writing software for spy planes. That was super cool.

I worked for a medical device company writing Device driver software for blood machines. So I really try to Change it up. and learn about different industries while I was studying for my undergraduate degree. Man.

Um In the midst of of sort of the er early part of your career,'cause I know one one of the first things you did when you when you had your degrees from UMass was you went to go work for a company called Interleaf, which I won't ask you about in a sec, but You got married really young, like twenty five, twenty six. Yeah, and Gene and I met at age eighteen as freshmen at EMS Boston. And we're married at age twenty five.

And uh had kids um a couple years in and we had two kids. Yeah, I have a son and a daughter. My daughter's Nicole, my son is Michael. And they both live in Boston and they're super close to both the parents. I'm divorced now for fifteen years, but I'm very friendly with my ex. We live close to each other. We're still very supportive of each other. And um We're both pretty close to the kids.

Alright, so you really one of the first r professional long term jobs you had was with a company called Interleaf, and I guess they were like an early Content management. software company and you were a program there and you you you must have done pretty well because they eventually promoted you to a a management role, right? Yeah, I started as a programmer.

And I love programing. I work a miljan hours a week. I worked weekends, I worked late at night, I was there early in the morning. I just became obsessed with programming But it's true that after a couple or few years they talked me into management, which I was really perplexed by and didn't like at first. I ran engineering there at one point and then my last year there I actually ran product management and marketing, which is kind of a crazy story. The company lost a lot of money one quarter and the board fired the CEO and appointed myself

and another executive as an office of the president. We had to go recruit another CEO. So we recruited this guy to come in as CEO. And on his first day He said to me, Okay, we have twelve VPs, which is double what we should have for a company of this size. So I'm gonna fire half the VPs tomorrow. I want you to run engineering and the business units,'cause I was running engineering at the time, or I can have you run marketing. I said, I don't know anything about marketing He said, Congratulations, your VP of marketing and

I mean, props to this guy for shaking it up. And I didn't really know what marketing was, but I figured, okay, we had a direct salesforce. I wanted to learn how to sell software. Because if I could design it and I could learn how people sold it, then maybe I could figure out what marketing was. And um it was a really fun job for me. This is a really heady time in Boston Tech. I mean I mean DEC, digital uh equipment I think it was called was one of the hottest and would become one of the hottest computer companies in the country. And there there are a lot of software companies that that don't exist anymore, and including Interleaf, right? I mean I don't think Interleaf is around anymore, is it? It's not.

It sold very successfully. I think it was a billion dollar exit to Um a company called Broad Vision, which is really hot During the beginning of the internet. The beginning of the web, I should say. Did you have any any stock uh options that you ha had? I did. I did. I made um

I made my first million when I was I have to do the math, but I think I was twenty nine years old. Wow. But I remember after I had vested half my options, which is a million dollars. I then got convinced by a l very gregarious recruiter in Boston.

To leave my big fancy job at Interleaf to go work for some unknown internet company. So I walked away from half of my options. And then worked really hard at at this crazy startup that imploded a year later. And so I learned quickly how startups shouldn't run. This is called net centric, I think, right? Exactly. Back then, this is back in like nineteen ninety six, maybe, nineteen ninety si nineteen ninety six, nineteen ninety seven. There's something called a point of presence, which is

Where are the internet companies connected users to the internet? It routed all the traffic from dial up modems to connect to other servers and and businesses. And we build software for these point of presence so you could route faxes through the internet.

And we s the beginnings of doing phone calls over the internet. All right, so you go and work for this company called Netcentric. I'm a startup. Which w wasn't gonna be you weren't gonna stay there long, but I guess while you were there

you either met or you hired two guys who would who would eventually become pivotal to your the rest of your career, a guy named Bill O'Donnell, one guy named Paul Schwank. D did you you hired them as engineers. Did you meet them there? I actually met them at Intrelief and Bill O'Donnell or Billow. as we called him and Paul Schwank or Schwank as we called him.

turned out to be incredibly instrumental my career. I've been incredibly lucky to work with those guys for decades. So I when I went to Net Centric, I hired them as engineers. And then there's another guy that I hired that I had not met before, named Jeff Rago, who also turned to be instrumental to my career. Really those three guys And a lot of

Being successful in tech is luck. Right. And a lot of it is picking the right people to work with and I felt lucky that I met these guys early on. And we developed a close friendship. And we work together across several companies over decades.

And they help All of my companies be very successful. So here's I think kind of an interesting thing that was going on, right? Uh uh on the surface, you were very successful. You had been promoted

to an executive position at the previous company, you're Um, you know, at a at a hot startup and I think Around this time in your late twenties, you know. You um Presumably went to go see.

a a doctor or a psychiatrist because you were suffering from things that maybe you couldn't fully understand, depression and anxiety and and Sleeplessness and also Is that right? I mean, is that w what was going on in your in your life? Yeah, so age twenty five was a big year for me. In one month

I had four big life changes. So I got my master's degree. I started a new job. I got married and I bought a house. And

I was working really hard. full time while I was going to grad school at night. And then switch. to a different company. And I was alternating between

Extreme depression. And panic attacks where I couldn't leave my bedroom. And I remember just Begging the sun to come out.

I just kept looking at the window sill for the first signs of light, and somehow when the sun came out It would calm me down a little bit. But I would go between these depressive episodes which lasted weeks A longer. and then manic episodes where I couldn't sleep.

And the mania or hypomania. Allow me to be Creative. But I also

Things would move so fast for me that I became detached from other people. Yeah. Like I was very irritable. And I had this perception which

I learned later was just grandiosity with it, everyone became too slow for me. But it just felt like I was separating from people at work. in my marriage uh with my friends I had trouble communicating with other people.

I mean People. First experience. Uh some types of mental illness in their twenties. There's some reason why. There's maybe it's it's a combination of where you are in life and where you're

how your brain is developing. Um and just this kind of perfect storm of things happening. Um How did you get to a point where you Where where you said I've gotta go see a doctor.

I didn't really know what a psychiatrist was, but I knew I needed to see someone who could help balance me. And I went to see a psychiatrist at Newton Wellesley Hospital. They had diagnosed me as bipolar. I had never heard of bipolar before. But it made me feel good because I thought, okay, if there's a name for it.

Maybe someone knows how to fix it. So They put me on lithium. And I remember I felt This is great.

If something can balance me out a little bit. But I was also afraid of the drugs because I thought it would cut into my creativity. And did it? Well

Put it this way, when I Started taking lithium. One of my Managers at Interleaf a guy I was very close to

pulled me aside one day and said, Is everything okay for you? I said yeah. He said. You seem like you're not yourself recently, like you don't have your energy. And I stopped taking the drugs.

After he said that because I thought This is terrible. I can't lose my energy. I can't lose my creativity. But then I went through cycles for years of taking the drugs, not taking the drugs. It took me. Probably Another fifteen years of

On drugs, off drugs, on drugs, off drugs. Until I found something that worked well for me. And I have not had a depressive like a full on depressive episode in twenty years now. So I'm hoping knock on wood that I've licked that with the meds and with other

Uh with meditation and therapy is helped me with that. Alright, so I think you're In your mid thirties, and you were at um this internet startup.

Yeah. And I think you stay there for what, like a a year or or or even Might maybe um even less than that. Yeah, my it's funny, my memory of my departure was that I was fired Years later.

Twice after that I met the founder, the CO again. His name is Shana Solomon, he's a wonderful guy. Went on to become a very successful investor. And we had breakfast after not seeing each other for twenty years. And we talked about

The fact that we had this fight and that I left I don't remember the final words that happen, but we we left over a big disagreement. I was hiring engineers at ridiculously low salaries. Like he really had this religion. He developed this cult.

of all of us were were very cheap. We spent very little money on computers and office and everything else. We were cheap as we possibly could. The size were cheap. And we're all gonna become millionaires on stock. Meanwhile The friends of my

engineer colleagues were all making big money at other companies. And so we had this agreement that the first time we shipped a server And we got revenue from a major network partner. we would increase the salary of the engineers. I remember I had a printed out spreadsheet with their existing salary with a new salary. I had the CFO literally sign it because I wanted evidence of these approved. And then I told the engineers you're getting a raise and Sean and I got a huge fight over it.

His memory was that I quit, my memory is that he fired me. and I ended up leaving the company because of it. Why don't we come back in just a moment, how Paul founded and then sold his first major company. And then have a chance meeting and a couple of gin and tonics? led him to an even bigger business.

Kayak. Stay with us, I'm Guy Raz, and you're listening to How I Built This. From NPR. Hey, welcome back to How I Built This. I'm Guy Raz. So it's around nineteen ninety eight.

And Paul English has just left his job at a tech startup. And he decides to launch his own business. Boston Light Software. It's kind of an early version of Shopify, helping e commerce companies set up their own websites. But of course, to do that. Paul has to find some money.

I spent my savings. I remember I was dipping it in my four okay at one point. And two of my friends put in a little bit of money. But We were a little company, we had fifteen employees. And um

It included my three star engineers who Bill O'Donnell, Paul Schwenk, Jeff Rego. And also my friend Jim Geeza and Carl Berry, that was sort of the core group that built Boston Light. And back then, this was early, early days in e commerce. I mean, Amazon existed and there were some big sites. But

You know Your average Stored on the street. Didn't have a website yet. E commerce.

It would still be another decade. Before it really started to take off. This is ninety eight. And this is right before the dot com Crash.

W was I mean were people Like just Racing to to put up e commerce sites? Most people didn't get it. We did a lot of individual selling where I literally went store to store.

And people looked at us. Like We were crazy people. Like why would a little bookstore create their own website shouldn't make sense to them. It's like that's not for us. That's for big companies. Little companies don't have websites.

And we learned That I think it's seventy percent of small business in the US. A service based business is not product based. And so then we did this pivot. We said, Okay, instead of just focusing on selling products

We should focus on selling services. And doing online invoicing. and online payments. So even like your plumber. could send you an email with a bill and you could pay that from the email securely. So we built that.

I mean I think Within a year. Of launching Boston Light Software. You got uh an offer and then we're acquired by into it. I mean that's

That's really fast. Yeah, I mean the the big tech companies all had a voracious appetite for internet because the big companies saw what was happening. The internet was gonna take over everything. Desktop software is gonna die. And they all wanna do business with us, which I thought this is great. Then when it turned out is the more time we spent with them, they actually all wanted to acquire us. They just wanted the talent. They wanted the engineers. And I made the decision to go with Intuit because

I like the culture, I like the values. I just thought it was a a good group of people. And I'm glad I went there. Yeah, I mean you sold it they bought it for thirty three and a half million dollars. A year, about a year after you launched it, which you basically signed a contract, presumably, and worked there for a couple years and became a a manager leading up to and and Were you what kind of man I mean, at this point you'd already had some management experience in your previous Jobs. Um You weren't very successful at it at Interleaf, as you a admitted.

Um, so presumably you were starting to get a little better at it. Yeah, I was reading books about it. It's funny I don't read business books anymore. I rarely read business books because this is gonna sound like a funny thing. to say for someone who's created a lot of companies is I don't actually like business. Yeah. I mean to me creating a company It's just the vehicle.

Where you can get a bunch of really fun people together and design products. Do something creative. Yeah, so it's just the business side of it's just a way I can get creative people together. The business just happens to be the way to do it. So When You sold to Intuit, which uh I think most people know is the

people behind TurboTax, right? Yeah, um. When you made that sale, right? I mean, look, this is ninety nine, so Your I don't know, almost th uh almost forty, right?

years old, late thirties. Late thirties, yep. Um, and you walked away with eight or ten million bucks and there's taxes and all all kinds of things. Um I have to assume it. Changed your life in some way.

It did. It was actually uncomfortable for me. To have that money. I actually originally I had a part time co founder, Carl And the way we originally started the company was I had two thirds, he had a third, and then we started giving stock out to all the engineers. So I think on paper originally I would have made twenty million. But

When we didn't We didn't expect to sell it that soon. When we sold it that soon, I felt bad the engineers didn't make enough money. So Carl and I canceled half our stock and just gave it to the engineers. So instead of making twenty million, I only made

Ten million. But then I also Wanted to figure out how to give away the money because It almost felt unsafe for me to have all that money in the bank. I thought it might disappear one night. So I started giving money away and that began A journey.

We are I spend A lot of hours a week. on philanthropy. Starting

In my late thirties. While you were still uh with Intuit, um because I know you stayed there till around two thousand two. Um I heard a crazy story. That you were

supposed to be on flight eleven. Um the flight. from from Boston to to LA that that ended up crashing the World Trade Center on on September eleventh, two thousand one, but you had Rebooked on a different flight that was cheaper.

Yeah, I don't tell that story often because I know people that actually died that day and I just had You know, maybe I would have gotten on the wrong flight. I think Flight Eleven was, if I remember correctly, was fourteen hundred to eighteen hundred dollars. And it was a corporate travel department that intuitive book flight, so it wasn't my money.

But I grew up frugal and so I didn't want to spend that much of the company's money. So I found a flight through Manchester, New Hampshire that was three hundred and forty three dollars and had a layover. But I felt proud that I saved the company money, so I switched to that flight. The interesting thing is when I put my son to bed that night, and my son was five years old My mother. Had died just a few months prior. And it was Kids say the most amazing things like just as they're falling asleep.

And my son said he used to call my mother Mimi. He said. Mimi took care of Dad to make sure he didn't get on the wrong plane today. And then he fell asleep. Wow.

Yeah. And He had no idea what he No. No.

Well. It's it's so crazy how Things happen. Like that. It really makes you think about

Things like fate and Why certain things happen to certain people. Yeah. Hopefully. What people come away with.

is to realize just the whole concept of impermanence. And There's something actually beautiful about acknowledging impermanence. It actually frees you. And it frees you

To live in the present moment. So hopefully I'm fully present today because none of us know what our future is. Yeah.

So uh I I guess in the in the period after that, um I mean you were juggling a a bunch of different things. You were uh working with your brother on a company um that that he had founded and Uh you were doing some work Advising nonprofits.

But also I think your your dad's health was And and you started to spend a lot of time Looking after him, right? I think the main thing during those years was my mom had died in two thousand and one

And literally on her deathbed as she was saying bye to each of us. The thing she said to me was keep up the good work. The keep up the good work actually

I read as I'm not done yet. Like I haven't won over my parents said, I need to keep working. And then she said, Take care of your dad And my dad had Alzheimer's early stage Alzheimer's that point. And when mom died, I started spending a lot of time with my dad and then ultimately left into it to as his condition worsened

And became his primary caretaker for about a year, year and a half. And I would feed him three times a day, bring him to all his doctor's appointments, try to entertain him And um that was my main occupation during those years. Well. Yeah.

I I think it it was around Uh, around two thousand three that w when you joined the V C firm uh Greylock partners as their entrepreneur and residents. And and presumably when you were doing that you were looking around for

And and I guess this is when you m you meet this guy named Steve Hafner. who who we'll get to in a sec, uh about who he is. Um but f but first, how did you meet Steve? One of my mentors From Interleaf. It's a guy named Larry Bonn.

And He's a partner. At General Catalyst in Harvard Square. And he had reached out to me to ask me to go look at a company for him. So I went to Cambridge To meet with a startup.

And then as I was leaving one of the other partners there had seen me. and said, What are you doing here? I said, I'm looking at a company with Larry And he said. There's a guy here I want you to meet. His name is Steve Hafner. He's one of the founders of Orbits, and he wants to start a new company. Would you meet with him? Orbits was a travel website. It is a travel website.

That he had started? He was one of the co founders of Orbits. He ran marketing there. Yeah, back in two thousand this was the end of Two Saine three at this point. And the big travel websites back then was Expedia, Orbits, Travelocity and Price Line. Those are the big four. So you knew what Orbit's was and uh presumably and presumably like Oh yeah, I'd love to meet the guy. Yeah. And Steve had an idea.

He was leaving orbits after four years. And he was frustrated with Orbits. And he had an idea of a different way to do travel, but he was looking for a CTO, a chief technical officer. And This other partner at General Catalyst thought

I don't know, m Paul's a good tech guy, maybe Paul can Steve and go work together. So the partner to do stuff, Steve and I went downstairs to legal seafoods in Harvard Square uh for lunch. I think we w each had a couple of gin and tonics maybe, maybe no food. And he gave me the pitch and he basically said

I want to create a search engine for travel. a search engine that has the stuff from everyone else's website. And I said, I think that's a brilliant idea. And we talked about it. He gave me his thoughts. I gave him some feedback. We went back and forth. Wait, just to be clear, because Orbits at the time and and Expedia, they were selling tickets on their site, presumably only with partners. partner in life. Correct. Like they they didn't have Jet Blue at that point, for example. The they didn't have all the content. They had a limited set of hotels, a limited set of airlines. And Steve said, Why don't we create a website that you can't buy anything?

All it does is search, but it searches everyone. Everything. Okay, I got ya. Southwest, Jet Blue, whoever, right? Yeah. Right. And There was nothing like that out there. Not

At the time there were Kinda simultaneous with the creation. Of our company. there was maybe four or five other companies being created at about the same time. quite a similar idea.

So it was not a novel idea, the idea of saying Google's a search engine, why is their search engine just for travel? There were a few people thinking about that. Yeah. But the funny thing about the meeting was I said I like the idea. I c he said he's looking for a CTO. I said I'll find someone for you. I run a group in Boston called Boston CTO. It's like twenty chief technical officers And I said, What are you paying? He said four percent and a buck fifty, like a hundred fifty thousand dollars a year. And four percent equity. Four percent equity. I said, That sounds great. I definitely can find someone for that. He said, Why don't you do it? And I left and I said, No, I just saw my last company to Intuit.

Um, I wanna create my own company again. He said, What would it take to have you join me as co founder? I said at a minimum fifty fifty, just kinda joking. Yeah. And he put his hand across the table and he said, Done. And I thought, Whoa I like how bold this guy is. He went from four percent equity to fifty fifty. Yeah. And and and just like that. And a handshake. Yeah. In a handshake. Yeah. But but he didn't even know you.

Steve and I We each have a lot of weaknesses. But I will say probably the superpower that Steve and I have. Is were really, really fast reads of people. And

I could tell quickly this guy was crazy bright. And I liked how impulsive he was. And I thought this guy's an entrepreneur, he's a natural born entrepreneur. Yeah, it might have been. Ha ha ha.

What what was it I mean this was not in your wheelhouse, a travel website, a consumer product, yeah. Not at all. Uh, but it appealed to you. Something about it appealed to you. Yeah, I mean I li so I first of all I love travel. I think I traveled about a hundred thousand miles a year pre pandemic.

And the idea that we're going to be able to do I could be in charge of designing a new travel site. and have ideas about how travel actually what it should look like on the web page. That was incredibly fun to me. So when you agree to do this

Presumably the first step was You had to raise money. Well, interestingly W Steve and I went upstairs after having Couple couple of drinks. Back up to general catalyst. That's right. Yeah.

And The partner, Joel Cutler. said to Steve, How did it go? And Steve said. Well

The good news is Paul's my fifty fifty partner. And we're each throwing a million dollars in tomorrow, which he f neglected to mention that to me at the lunch. And then he said the bad news is I'm tearing up that term sheet'cause I'm worth a lot more now that I have a CTO. And he was just I think he was joking a little bit. But anyway, General Callis put in five million, Steve put in a million, I put in a million.

And then we started Kayak. And the immediate thing we did immediate thing we did was uh start recruiting. Right, sorry. So you raise some you raise some money. A little bit from you, a little bit from Steve. Some general catalyst.

And do you dip into your team, those guys, Bill O'Donnell, Paul Schwank, Jeff Raygo, those guys that Jim Giza who worked with you at your previous companies? Yeah, so those are the first four phone calls I place was to those four guys. And they all said yes. They all said yes. And the interesting thing I'll tell you about my negotiations with Billow. Um

So he was a an architect added to it because he again, he and I worked together for decades. So he was at Boston Light. We sold to Intuit, he became an architect at Intuit. I'm guessing by memory he was probably making four hundred K a year into it. And I recruited him. I said I'm starting the company, I want you to come work with me. And he said, What's a company? I said, Travel.

And he said, How much will you pay me? I said I'll pay you a hundred K. Class. Two percent of the company. Yeah. And

I remember thinking, is he really gonna go for this hundred K thing?'Cause he's probably making four hundred K. Said I'd love to work with you and I have three questions. What do you count what's the company doing, Travel? How much you pay me? A hundred K and two and then two percent. And the third question was, Where's the company located? I was fearing I was about to lose some of the salary issue, so I said you pick the location. So he chose the first office. Um it turned out to be a very good financial decision for him to get two percent of kayak. And the f the office was in Concord, Massachusetts, right? The original office of the first year was in Maynard, Massachusetts, which I was not happy about.

And meantime Steve Hafner was gonna work out of Norwalk, Connecticut. Is that is that right? Exactly. We have where he lived? He lived yes. And we had the tech team. in Main and Concord Mass for many, many years, where Kike still has an office. So tech was up here just outside of Boston and the commercial team was in Connecticut. How come you guys split it up? In two thousand four, it wasn't like today, there wasn't Slack and Zoom and all the stuff. Like that that's that's distributed remote workplace in two thousand four. Yeah, I mean Steve and I both had made money before.

And I wasn't gonna move, he wasn't gonna move, so we said, Let's try it. And It worked out really well. Alright, so you guys uh have these two offices and you've got Some working capital.

What did you want your role to be? I mean Obviously you know how to You know how to build these things, you know to code, you know how to run engineers. W but what about design? Were you focused on the actual user experience? Yeah, I mean going back to Interleaf

most of my work at Interleaf was on the user interface and that's what my obsession was. And even going back to my first program I'd ever written, the the video game back when I was in high school, I focus on the user experience. I've always been interested in that. And so for The travel company

I wanted to build something that was unlike any other travel website. I wanted something that was cleaner. And simpler and faster. The first day Steve and I met In Cambridge. I went home that night.

I spent probably Ten minutes on Expedia. just to see what the market leader looked like to remind myself. And I thought this is not gonna be hard to beat this because to me expedient was epileptic seizure inducing. I mean, it's really terrible. There was so much animation and graphics and so much stuff going on the website. I thought we can build something dramatically simpler than this. And but by the way.

The name Kayak, what's up with that name? How did It's just a weird name for travel website. We hired a top brand agency in New York City named Wolf Olens. And The project, the branding project was led by a woman named Carol Costello.

Yeah. And Steve and I met with her weekly over maybe a six week process. What's the brand identity? What do we want people to think about when they hear the name of the company? what's life gonna be like before our product and then after people use our product. Spend a lot of time talking about those things. Ultimately her team came up with a list of about a hundred names.

And We narrowed it down to five. The reason I liked kayak was I like the letter K. It's a very valuable letter in branding. I like that it was a palindrome spelled the same backwards and forwards. I like that it was only five letters. And it meant like freedom, which is like a great word.

And it's very difficult in branding. to take a word to mean ch which means one thing and change it to mean something else. But if you're successful And you own that word. It's incredibly valuable.

What were some of the other names you thought of? I'll go in reverse order. Number five was Hive. Not a bad name, like a Hive where you go and get the tickets and get all your stuff. The bad thing about it was the beast thing. Oh yeah.

Yeah, you don't get stung in that hive'cause then your whole vacation's ruined. Yeah. Number four. was rice because it's ubiquitous, global, and simple. Hm. Number three was cake,'cause who doesn't like cake? I like cake, but not for my travel. I don't want cake on my travel.

Number two is kayak. Okay. And the first name, the one we really wanted, which we tried to buy And we could not buy the domain name. was Lola.

Ha. Huh, which would come back to um Which would come back to be part of your life later on. Yes. Alright, so you c so you've butt kayak and

Did anybody s like get on there initially and say, Where are the kayaks? Like where's your kayak gear? Like what are you doing? We literally got hate mail from kayakers. Out Yeah from kayakers, yeah. We said this was terrible that we took this over and this is like a blight on the internet. You know, that someone would take over their precious hobby. Yeah. And use it for something dirty like a travel site.

when we come back in just a moment. how Paul found out that the much resented name for his new business was becoming one of the more popular search terms. on the internet. Stay with us, I'm Guy Raz, and you're listening to How I Built This.

From NPR. Hey, welcome back to how I built this. I'm Guy Raz. So it's 2004, and Paul and Steve have just come up with seven million dollars. A small team of engineers and a name for their new travel website. Kayak. And it isn't long before they put their first product

out into the world. So believe it or not, we released The first Beta. which is limited software that we don't promote yet, but we had a functioning flight search.

On cinco de Mayo, two thousand and four. And this was just for for friends and family to test out. Yes. And um how long before you you made that public? We made it public, I believe, in October of two thousand and four. All right, now You guys had some working capital because you got investment money, but you're f you were you were like

a nobody in a in uh among giants like Priceline Expedia Orbits, how are you gonna even get the word out about kayak? Well What I used to say on early days of kayak is Every company in the world only has ten Ten smartest people.

So Expedia, only ten of them are the ten smartest. And even though we're much smaller, we have our ten smartest people, they have their ten smartest people. I think my team can out design them. And we were just, you know, it was a little bit of arrogance. Hopefully we had some humility as well. Like we knew we were small. We knew that no one heard of us.

But we Steve and I We're both very aggressive recruiters. And we thought we can recruit a really extraordinary first ten person team. the business model was gonna be different because Expedia, you know, they would get a commission on the ticket sales. Your model was for every referral you made where a person booked a a ticket.

that company or site. or hotel would send you a commission, fifty cents a dollar for Exactly. But how do you how didn't you have to manually like make those 'Cause if it was a search engine for the entire travel industry, did you have to individually call Jet Blue and Delta and American and Hilton and Hyatt? Really? Yeah. It took us

probably two years to get those deals. So originally Kayak had no revenue. And also we were scraping these websites without their permission. It's one of these things sort of Ask for forgiveness, not permission. We're just moving as fast as we possibly could. So we just scraped websites. It took us about

A year, year and a half till the software felt really good. And then we started growing rapidly. How did you grow rapidly? Just from word of mouth. I mean, believe it or not. In the early years of kayak, it costs us about a dollar on average to buy someone to come to our website from us spending money on Google AdWords or uh other websites.

We made on average 20 cents per user, so we were losing 80 cents a transaction in large numbers. We were losing a lot of money very quickly. But if you build a really amazing website and you pay to have them come here. Will they remember this word kayak? And then next time they buy travel, will they go directly to cock dot com without having to go to Google first? Yeah. And it worked.

And people told their friends about it. And so it got to the point where Seventy percent of the traffic on kayak. was self-directed, meaning someone typed kayak.com in their browser. And as soon as that traffic grew from zero percent ten to twenty to thirty to forty percent more. Then the economics started working.

So Basically You would take the data. Presumably, like you would take the data of people booking through kayak and go to the Deltas, the Americans, the Hilton Hotels of Mary's and say, look, we can show you how people are already going to your site through kayak. Exactly. And that's how you would convince them to say, Okay, fine, we'll pay you

fifty cents or a dollar for every time that happens. Yeah, and for the airlines, originally kayak was flight only. We didn't have anything except for flight, no hotels, no cars. And we did Manage to get a really good deal with Orbits early on. Steve again was one of the founders there. He was friends with the CEO We were able to negotiate it with Orbits to say

When you see a result from American Airlines We give people the option to click here. To go to A.com to buy it. Or click here to go to Orbits to buy it, and Orbits would pay us. We both said We're a little company, we're a new business model, we're search only. You orbit should participate on this. We'll give you an exclusive. You're the only agency we're gonna let on our site.

And maybe we're little, maybe we're gonna grow fast, but you should get in on day one. As the e commerce behind kayak. Which they did. The nice thing is we then called American Airlines, we said, We're selling your flights all day long. But we're selling them through Orbits, wouldn't you rather us sell them through AA dot com?

And we use Orbits as a stalking horse. To get all the airlines to pay us directly. So we could send people directly to the airline sites. Wow. Did you see Orbits as a competitor? Well

They were different flavors than us. They were a merchant. But we used to say search with us, book with them. We didn't have customer support if your plane was late. Call the airline, don't call us. We were just We're literally just a thin search engine.

We used on the back end another search engine called IT software, which later became Google Flights. And my friends at ITA used to make fun of Kaik. They said, Kyke is a joke. It just sits on everyone else's technology and all Kike is is a thin UI layer. And my response that was Exactly. You were the user interface on you were basically like

a skin on top of a uh really Sophisticated technology. Yes. That somebody else built. But that that's where I wanted to be. I wanted to be the front end. And I thought that's where the innovation needed to happen.

mean that's that's brilliant. So you didn't actually need to have a massive staff. No. How many people By two thousand six, two thousand seven, we're working a kayak. I think by the time things started growing, we were maybe fifty or sixty people.

The best people Like in terms of quantitative people stat at kayak. is when we took it public two thousand and twelve. We only had two hundred employees, which is pretty small for public company. And we had three hundred million in revenue. So it was one and a half million per employee. Wow. We were crazy profitable and fast growing. Because you were so lean.

Very, very lean. Alright, so I guess Three years in, three and a half years in, December 2007, you raise a big fundraise,$200 million. Sequoia leads that round, Sequoia Capital. And that means you can really get you can now like do things like acquire other companies and

you know, launch a big advertising campaign. When did you feel like you were now? A player in this space. Was it Was it W around the time you raised that money, that two hundred million?

It was before that. I mean there were several milestones for us. But J The number we looked at that I looked at most carefully is what percentage of our traffic was self directed. And as that number started growing, my confidence started growing because I said, if people come back to us, if they remember our name and they tell their friends about us, things are working. One of the biggest milestones in the history of kayak.

is when you went to Google and you typed the letter K, the first word that came up was kayak. I thought that was cool. Wow. What about your what about your mental health? Were were you H how are you doing at that time? I think

I at that point I had pretty much controlled the depression, so I had Little to no depression during kayak. But the Manic episodes continued. I would go through waves of sleeping very little.

I always have a um A sketchbook. With Colored pencils. And sometimes I'd wake up at four AM and I'd draw pictures of what

I want a Kai to look like, like for a new feature. And I would email them To our head designer Lincoln Jackson. And then we got a meeting. And so

I remember once we took a drawing that I did at Three or four a.m. We had a meeting with myself, Lincoln, and Jeff Rego, who's our lead developer. And then Lincoln cranked out a Photoshop version of what I did, but he pretty much ignored my drawing. He did something completely different, but it was inspired by my drawing. And then Jeff wrote the code and Jeff ignored Lincoln's Photoshop and did something that he thought was even better. And we just had this relationship of really rapid iteration where we would each contribute ideas.

And I remember during That time period. I felt completely Manic. Things are moving very, very rapidly. I read there was a there there was sort of a joke that used to go around that You would send a lot of emails like

Hey, I have an idea,'cause you're just an ideas machine. And um or hey, why don't you try this? And there was a joke among Um some of the the team who are loyal to you, but But there was a joke that they would ignore your emails and Uh because they they you would just forget about it.

over time and that when you found out about it actually initially it hurt your feelings. It did. Um I'm probably guilty of sending too much email. Particularly when I'm in my you know creative or hypermanic states. Yeah. Yeah. I can be prolific on email. I mean I can send hundreds of emails a day.

And so my team was always like, Whoa It's like we can't handle All these different things like try this, try this, try this. And so sometimes there was this private joke that we're not gonna do something unless Paul asked us to do it twice. Unless the next day he still wants to do that thing. And I've heard this criticism of other entrepreneurs as well. So I don't think I'm unique in that. Yeah. And that

that I always want to push forward on multiple ideas, but I was both amused by it when I heard this, but also a little bit sad. Yeah,'cause basically w it confirms that You are an ideas machine. You're a little bit manic, and that's with that comes a lot of ideas and a prolific outpouring of ideas, but if every single idea was acted upon it would be chaos.

Yeah, I think so. And Um I think it's fine for someone to have Like nine terrible ideas as long as the tenth one is really big. Failure's okay. We build a lot of technology at COC that we throw away.

We pursued some ideas which turned out to be stupid ideas that We worked really hard at them, no one used it, we threw it away. So that happened many times at Kayak. Yeah, what's so interesting is that this insight that you had because I I think you previous companies that you had started I would

And and correct me if I'm wrong, but I think that the back end technology was probably more complex than than it was for kayak, that actually your insight was, look, the technology is out there. We don't have to make it better. We just have to make the user experience better. That's right. It's interesting. When we created the company, Steve and I both thought If we make it big, the way people are gonna know us is We're gonna have all the content on one website.

That's what we're gonna be known for. It's not actually what we became known for. The way people talked about kayak wasn't that, oh, that's the site that has all the content. Which we were hoping they would say. But what they did say was oh yeah, that's a site that's really fast.

Yeah. Oh, that's a site that's really clean. So I like that. Because that's where you invested your money. Yeah, and it was it was a huge investment. Becoming fast is not easy. Becoming simple is not easy. Scott Cook at Intuit used to say, It's very easy To build complicated software. Mm-hmm.

And what he means is to build something simple takes years. Yeah, I mean You are a a backend programmer who essentially built a brand. You weren't building a new technology. You were building a brand.

Yeah, when I think of the first ten years of kayak, I think there are three things. Those three things came together, really good user experience, really good brand, and really good commercial partnerships. Yeah. In July of twenty twelve, kayak went public. Um, I think it it raised one point two seven billion dollars on the Nasdaq. Um

That Um and By the end of that year. Uh it was announced that Priceline would acquire kayak for one point eight billion dollars.

Which basically to kayak would be under Priceline's umbrella. I think it's ca the the trading name is Bookings dot com or something or bookings. Bookings holdings. So You know. Priceline buys out kayak and

by the time I think it it it all was said and done. but two point one billion or something. Um in the book that Tracy Kitter wrote about your life, he he there's a scene where

You know, the news breaks inside of kayak's headquarters, people are so excited, somebody's passing around a bottle of five hundred dollars scotch,'cause everyone's like, We got all this all this money. And uh you're sitting there at your like cubicle at your desk just like Quiet. Um I don't know.

W what was going on in your head? It was a little overwhelming. I mean, my first thought was always how happy I was for the team. We had two hundred employees, over half of them became millionaires that day. It was great to see them celebrate the IPO, it was great to see them celebrate the acquisition. It was really an exciting time for people.

As far as the The fame that came along with it. That gave me anxiety. I'm an introvert. By nature.

I do not like being center of attention. there's certain advantages to it, like it helps me raise money, it helps me hire people, but I'm a little bit uncomfortable with it. And when We started getting a lot of press after the IPO and after the

acquisition I started getting a lot of incoming requests. And I didn't know how to do it with them for money. I mean I had philanthropy, right? Yeah. Right. Not just philanthropy. I had someone show up my house who asked me to pay her mortgage. lot of people ask me to invest in their business. A lot of nonprofits.

Uh hit me up. And it was overwhelming because It's tough for me to say no. I've had to learn to say no simply because I cannot afford to write checks to all the nonprofits who email me every day'cause I want to have a focus area. But

Just the amount of money that I made in the sale. was a little overwhelming. And I kinda had this instinct of getting rid of it, like giving all of it away immediately, which I'm glad I didn't do that because I've been able to be be more thought about my giving over the years and I've now started three nonprofits that are all doing well.

So that's been really meaningful to me and hopefully we've helped a lot of people But um I definitely Have never been. become really comfortable with the money part of it.

You basically in your mind sounds like you knew that you were not gonna continue to work for Price line. I mean the main thing I wanted there, it was unlike when I sold my little e commerce company to Intuit. I wanted to work it into it. I wanted to build careers.

For myself and people and learn skills. Yeah. But when I sold kayak to Price Line, I felt like Um I had a very senior team. At kayak. I literally felt like they could run it without me. They didn't need me as much anymore.

And I think I spent a year with Priceline transitioning and getting everyone set up for success. So I felt very good about it on the day that I left that they were in a really, really good position, and kayak continued to thrive. I I read that that you that the CEO of Price and was not happy when you told him that you were leaving. Yeah, he was not happy. Right,'cause they were buying you too. Yeah. They were buying your brain. Yeah.

I don't know what to say about that. Part of it was probably the wealth thing. I wanted to be in the shadows after that. I didn't want to be public face at that point of this. You know, this guy with all this money, I wanted to hide for a little bit.

Also, I mean, this was the longest you'd worked on one business, two thousand four, two thousand twelve, right? Ten years. It was it was a total of ten years, two thousand fourteen, yeah. We we will not have time in the course of this. episode to get to all the businesses you've done'cause that that would take uh multi part episodes, like several multi part part episodes. But uh there is one I wanna touch on which is In the middle of kayak.

You launched a new company, co founded a new company called Get Human, which is still around, I think. It's a database of customer service information. So like if you want to find a human customer service rep, you could find their a phone number. Uh the best time to call. Yeah. And First of all.

As somebody who does multiple things Also um I have a lot of appreciation for that, but it causes tension sometimes and I have to imagine that it caused tension. There were people who were like, you know Paul, like we need you here, like focus on this. Or maybe Steve was like, Hey, you know, I I I mean, did it cause tension at times?

I mean get human became Wildly popular. I created it in two thousand and six. Yeah. And we got

massive media the first year. Yeah. I got covered. on every national network and magazine and et cetera. And

Sometimes I want to come in and do a photo shoot. Arn of you. I tried to schedule all of those to not happen at Kayak Office. I was embarrassed about this side project. It's not that I hit it. I shouldn't want to see people be working on it. However I don't think anyone would ever say that I was a slacker.

a kayak because I pushed really hard on design and engineering and performance. But yeah, I did have a couple of side projects. Do you still own it? Get human yes. It's a very it's small company, very, very profitable.

run by two of my friends in Boston, Christian Allen and Jeff Welpe, and it's it's an amazing company. Wow. H how does it make money? Uh through advertising. Um, wow, all right, so you do that in the meantime. You st then you step down From Kayak.

and you start to do some teaching at MIT and and RISD and a few other places at Harvard Business School. Um, I can't get into everything you've done because you've done so many things, but one of the things you you you then Created and twenty fifteen. was Lola. You went and bought that site.

This is a travel concierge app. First of all. I'm assuming this is g geared towards businesses, right? Exactly. Wasn't there like a non compete w when Priceline bought it that wouldn't allow you to get into the travel business again? My non compete ended it was an eighteen month non compete. It ended on july fourteenth, twenty fifteen.

I incorporated Lola on july fifteenth, two thousand fifteen. Nice. But I have to say, Lola has evolved. Like when the pandemic hit a year and a half ago and business stopped, like travel stopped, I mean. Um, we did a major pivot. To say rather than selling travel

software to CFOs saying we'll reduce your cost of travel. We're gonna sell software to CFOs that manages all the money their employees spend. So we call it spend management. Budget and spend management. Yeah, we basically manage every penny that your employees spend. What are their sp They're spending money on Google AdWords or

Amazon AWS or they're buying lunch for a client, or they're ordering supplies for the office. Anything they spend, if they spend it using a Lola card, we actually issue cards like a Visa card. If you use a Lola Card And you just tag it at the time you swipe at the restaurant.

You never have to film expense support ever. And we guarantee to the CFO That you're team will always be exactly on budget. No one will ever actually go about budget because the credit cards that we supply are tied to the budget of sales or marketing, whatever your department is.

So it completely changes the way finance people work. Is Lola now your primary focus, would you say? It is. It is, very much so. I mean I work on Lola five days a week. I have it's a little crazy, but I'm running three nonprofits. And then I have two other small startups that I run on the weekends. One is call is a podcast discovery app called Moonbeam.

Yeah, Mom being done a fam. You have got a nonprofit called King Boston that focuses on on like celebrating the work of Dr. King and and his wife, Coretta Scott King. Right in Boston. You do A lot of work in Haiti. Yeah. Um

I mean Here we are. Coming out of the pandemic. And you're Right.

Late fifties? I'm fifty seven. How many more businesses do you have in you? I mm some day I will move on past Lola. Lola's my day job right now. I think for the rest of my life

Rather than doing a V C back company. I think what I might do Is just have fun with these creative outputs and try to crank out. Like two to three or four companies a year. Because the most fun for me in starting companies is like day one.

But It's all a matter of um You have to have the discipline to say no,'cause it could be like too much stuff to work on. And you have to just be very choosy about the stuff you do work on. So like I have an incredible assistant, Eliza. and we color code my calendar. Everything is one of four colors.

And every Monday and Friday we look at my calendar two weeks in advance. And we make sure there's a balance. So purple is Lola, which is that's the brand colour for Lola. And that's mostly Monday, Friday night to five. Yellow is nonprofit work, which is about eight hours a week.

Green is self improvement, which is going to the gym or going to therapy or going to my Buddhist class, which I do on Thursday nights. Uh and then blue is everything else, sort of friends and family. And if I have a balance of those four colors, life feels really good to me. When you think about all all the things you've achieved, right, and and You know?

the financial success, but but really more importantly the Just that Innovations that you've been part of And the people that you've been able to work with and the teams you've been able to empower. How much of that do you attribute to your intelligence and hard work and how much

Do you chuck up to luck? I don't like to think of myself as intelligent. I will admit to being creative. Um I think my success leads to maybe three things.

I do think work ethic's a part of it. The frugality and effort. I think the creativity is a part of it. And then the third thing, which is probably the biggest thing. is I love recruiting and I love being amazed by other creative people.

And I put a lot of effort into that. So with each of my companies and organizations They thrive only if I'm able to attract really great people to work on them. And where do you put luck on that scale? Um, kayak was tremendous luck. I mean, it started with luck. I mean

Just by chance I happened to be in that office when Steve was there. And then luck along the way of hiring certain people to really transform the company. Um I don't know, maybe it's

Maybe that's those four things twenty five percent each. Okay. Uh w one more thing I wanna ask you about, Paul, um before I let you go. Um You have been an Uber driver, right? You signed up to be an Uber driver in your Tesla in Boston, right? Mm-hmm.

Yes. Do you do you still do that? I haven't done it since the pandemic just because I was nervous about You know, people in my car. But now that

I think in Massachusetts now we have over seventy percent of people are vaccinated. I think when it gets up to Eighty, eighty five percent I'm gonna start driving again. Tell me the Uber story. Why did you want to be an Uber driver? So the first reason I signed up was At Lola.

We have twenty-four seven customer support, and we it's really the front of lola is we want to have unbelievable customer service. But at the end of every interaction in the Lola app, when you've talked with one of our service people, you get to rate them, like on a scale of one to five, how well is the service they did for you. But before I inflicted that upon our customer service people, I wanted to show that okay, I'm happy to get rated. I want to see what it feels like to get rated. Being an Uber driver was the easiest way to do that because you get Real time feedback in the driver app, you get feedback every day about how your rating is.

Did any drunk kids ever barf in your Tesla? Thank God no. I had a rule that when I would drive at night As soon as I got the first drunk, I would stop driving. I didn't want to take that risk. Yeah. You know, and a good on a good Uber night. What are you pulling in? Um I think usually it's about fifty dollars is what I make.

Just going out for a couple hours. I think my my biggest night I made a hundred dollars. Nice. That's Paul English, occasional Uber driver. and founder or co founder of among other things Kayak.

Lola.com Moonbeam. Intermute. Get human speed games, Boston Light Software. And the online Chinese chess site.

Shangxi.com Oh, and just in case he needs them. Paul owns more than two hundred domain names. Including a whole bunch of words he just likes the sound of. Words that could one day inspire his next big idea.

Whale tails, Zarzan, Easy Mighty. Stay tuned up, Cloakley, Elephant Games, Road Wars, Down Dudley. Hey, thanks so much for listening to the show this week. If you're not a subscriber to the podcast, please do subscribe wherever you get your podcasts. You can write to us at hibt at npr.org. If you want to follow us on Twitter, we're at how I built this or me at guy. Our Instagram is at how I built this NPR and mine is at guy.Roz. This episode was produced by Faris Safari and Deba Motasham with music composed by Ramteen Arablui. It was edited by Nebu Grant with research help from Claire Murashima. Our production staff includes Casey Herman, Rachel Faulkner, Liz Metzger, JC Howard, James Delahousey, and Julia Carney.

Our intern is Harrison VJ Choi. Jeff Rogers is our executive producer. I'm Guy Raz and you've been listening. To how I built this. This

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