KAYAK: Paul English

Summary

How I Built This with Guy Raz

Episode: KAYAK: Paul English (September 27, 2021)

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Episode Overview

In this episode, Guy Raz interviews Paul English, co-founder of KAYAK, about his journey creating the travel search engine and several other startups. English, a serial entrepreneur, opens up about his working-class Boston upbringing, grappling with mental health, his path through the Boston tech scene, and the thrill of building creative teams and products. The conversation delves deep into English’s philosophies on business, luck, design, and leadership, concluding with insights on philanthropy, innovation, and managing personal passions.

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Key Discussion Points & Insights

Early Life and Upbringing

• Working-Class Roots: Paul English grew up in a crowded, working-class family in Boston, sharing a three-bedroom house with eight other family members. He reflects on the practicality and simplicity of his childhood.
  • “The brothers, the four boys slept in the attic which had no heat and no air conditioning. The worst part of it was we had one bathroom with nine people… but it was fine. Like we didn't know anything different.” — Paul English [07:43]
• Parents' Influence:
  • Father was a pipefitter for nearly 50 years—charismatic, strict.
  • Mother suffered from a debilitating muscle disorder but recovered through what she believed was a miracle.
  • “My father had really good influence and skills. He was very charismatic and very confident.” — Paul English [08:36]
• Marriage and Family: Married young, had two kids, remained close with them and his ex-wife after divorce.

Academic & Early Technical Interests

• Restless Student: Struggled with classroom settings, possibly had undiagnosed ADHD, but excelled in science and music competitions.
• First Computer: Mother bought a Commodore VIC-20, which sparked his interest in coding and led him to write his first video game, "Cupid."
  • “I 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, this way to make money programming.” — Paul English [14:33]
• First Business: Sold his game to GBA for a brief payday (though the company went bankrupt before paying the full fee).

Early Career

• Diverse Experience: Worked for companies like Data General, wrote software for US Air Force spy planes, and explored different industries while completing his degrees at UMass Boston.
• Interleaf: Found real success here—learned both engineering and, unexpectedly, product marketing after being thrust into new management roles.
• First Startup Miss: Left Interleaf for the startup Netcentric, losing out on stock options, but gained valuable lessons on what not to do in a startup.

Mental Health Struggles

• Diagnosis: In his mid-20s, English was diagnosed as bipolar after experiencing alternating depression and mania—key to both his creativity and his challenges.
  • “I would go between these depressive episodes… and then manic episodes where I couldn't sleep. …I became detached from other people… I had trouble communicating.” — Paul English [23:56]
• Impact on Work: Initial treatment dulled his creative side, leading to cycles of starting and stopping medication for many years.
• Resolution: Found a balance of medication, meditation, and therapy; hasn’t had a major depressive episode in 20 years.

First Major Exit: Boston Light Software

• Bootstrap Beginnings: Founded in 1998, initially focused on e-commerce for small businesses, then pivoted toward invoicing and services.
• Rapid Acquisition: Sold to Intuit in about a year for $33.5 million, walked away with $8–10 million personally after splitting more with his team than originally planned.
  • “It was actually uncomfortable for me to have that money… so I started giving money away. And that began a journey where I spent a lot of hours a week on philanthropy.” — Paul English [34:16]
• Surviving 9/11 by Chance: Was booked on American Airlines Flight 11 on 9/11 but switched flights to save company money—his son later attributed the “save” to his grandmother’s spirit.

Meeting Steve Hafner & Founding KAYAK

• The Meet-Cute: Introduced by venture capital partners; after a lunch (and gin and tonics), Hafner impulsively offers English a 50/50 co-founder split on the spot.
  • “I said, at a minimum, 50/50. Just kind of joking. And he put his hand across the table and he said, done.” — Paul English [42:18]
• Team Assembly: Quickly brings on core engineers from his previous startups, offering much lower salaries but meaningful equity.
• Two-Office Model: Tech based near Boston, commercial in Connecticut—a rarity before remote work tools were common.

KAYAK’s Differentiator: Simplicity & User Experience

• Design Obsession: English focuses on building a "cleaner, simpler, faster" flight search engine—contrasts vivid, distracting competition like Expedia.
  • “The first day Steve and I met… I spent probably 10 minutes on Expedia… and I thought, this is not gonna be hard to beat this because… there was so much stuff going on.” — Paul English [47:31]
• Origin of the Name:
  • Brand agency selected "Kayak" (palindromic, short, evokes freedom).
  • “I liked the letter K… it meant like freedom. It's just like a great word. And it's very difficult in branding to take a word 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.” — Paul English [48:12]
  • Received angry emails from kayakers about “stealing” the word. [49:33]
• Product Launch: May 2004 beta release, public later that year.

Business Model and Growth

• Lean, Profitable: Kayak starts with no revenue, scrapes data without permission, and slowly negotiates deals with airlines.
• Referral-Based Revenue: Instead of commissions for selling tickets, Kayak gets fees for referrals to airline and hotel sites.
  • “Originally Kayak had no revenue. And also we were scraping these websites without their permission…. It took us about a year, year and a half till the software felt really good. And then we started growing rapidly.” — Paul English [52:17]
• Word-of-Mouth and Brand Building: Spent money on Google AdWords, but focus was always on making the product memorable and easy to recommend.
• Team Size: Extremely lean—only 200 employees and $300 million revenue by IPO.
  • “It was one and a half million per employee. We were crazy profitable and fast growing.” — Paul English [56:20]
• Key Metric: Percentage of users coming straight to Kayak’s site—proof of powerful brand ("K" in Google autocomplete was “Kayak”).
• Role and Mental Health: Mania fueled productivity and creativity; had a culture of rapid iteration and was known for sending prolific idea emails, not all of which teams acted on.

Exit & Aftermath

• IPO and Acquisition:
  • 2012 IPO, then acquired by Priceline/Booking Holdings for $1.8 billion by the end of that year.
  • Majority of Kayak employees became millionaires from the deal.
  • “My first thought was always how happy I was for the team. …As far as the fame that came along with it, that gave me anxiety. I'm an introvert by nature.” — Paul English [63:09]
• Transition: Stayed to help transition business, then left; was not comfortable with fame or sudden wealth.
• Philanthropy: Channeled much of his wealth into nonprofit work and thoughtful giving.

Later Ventures & Life Philosophy

• Side Projects: Built GetHuman (customer service directory) during Kayak, runs it still via friends.
• Lola: After non-compete, launched Lola (spent management for business travel), adapting business model during the pandemic.
• Multiple Parallel Projects: Schedules life with a color-coded calendar to balance startups, non-profits, self-care, and family/friends.
• On Being an Uber Driver: Drove Uber to experience customer feedback firsthand and to lead by example.
  • “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.” — Paul English [73:29]

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Notable Quotes & Memorable Moments

• “Many times I'd say, I have to go to detention. I said, I can't. I'm an altar, but I have to go to church. And they wouldn't believe me. …I'm still amazed...who came up with this idea to make kids sit in a chair at a desk for eight hours? It just seems crazy.” — Paul English [12:20]
• "I said, at a minimum, 50/50 [partnership]. ... And he put his hand across the table and said, done. And I thought, whoa, I like how bold this guy is." — Paul English [42:16]
• “We literally got hate mail from kayakers…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.” — Paul English [49:33]
• “Failure is okay. We built a lot of technology at COG that we threw away. …So that happened many times at Kayak.” — Paul English [60:11]
• "To build something simple takes years." — Scott Cook (quoted by Paul English) [61:42]
• “My success leads to maybe three things. I do think work ethic is a part of it. …I think the creativity is a part of it. …And then the third thing, which is probably the biggest: I love recruiting and I love being amazed by other creative people.” — Paul English [72:02]
• "Kayak was tremendous luck...I don't know. Maybe it's those four things. 25% each." — Paul English [72:58]
• “As kids say the most amazing things…my son said Mimi took care of dad to make sure he didn't get on the wrong plane today. And then he fell asleep.” — Paul English [36:22]

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Segment Timestamps

• Early family and upbringing: [07:43]–[15:12]
• First computer/video game business: [14:33]–[16:58]
• College and early jobs: [17:01]–[21:00]
• Mental health and life changes: [23:56]–[27:15]
• Early startups & Netcentric: [21:37]–[29:08]
• Boston Light exit / 9/11 story: [30:25]–[36:49]
• Caretaking for parents, set up for Kayak: [37:13]–[39:54]
• Founding Kayak, team assembly: [41:15]–[46:00]
• Design/user experience focus: [46:20]–[47:38]
• Naming Kayak, public response: [48:12]–[49:45]
• First launch and business model: [50:29]–[53:59]
• Growth, partnerships, profitability: [54:00]–[57:32]
• IPO and sale to Priceline: [62:01]–[65:06]
• Philanthropy and discomfort with wealth: [63:55]–[64:48]
• Later businesses/side projects: [66:06]–[70:00]
• Personal philosophy, calendar balance: [70:28]–[71:40]
• Luck vs. hard work: [72:02]–[72:58]
• On being an Uber driver: [73:09]–[74:29]

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Final Themes

• Creativity > Business: Paul English thrives on imagining, building, and iterating on products—constantly seeking "day one" start-up energy, rather than managing or scaling mature businesses.
• Product Simplicity: True innovation for English is relentless focus on clean, intuitive user experience, even if technical innovation is built atop others’ tech.
• Luck, Team, and Giving Back: Luck, team-building, and sharing success are recurring themes, as English discusses luck’s role in tech, the joy of recruiting, and his philanthropic drive.

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This episode offers a thoughtful, candid look into the mind of an entrepreneurial maker—not simply a manager— driven by curiosity, collaboration, and a passion for making better experiences.

Transcript

[Guy Raz]

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[Paul English]

We hired a top brand agency in New York City named Wolf Olens. The branding project was led by a woman named Carol Costello. Ultimately, her team came up with a list of about 100 names, and kayak was actually our second choice.

[Guy Raz]

All right, so you've bought 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?

[Paul English]

We literally got hate mail from kayakers. From kayakers, 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.

[Guy Raz]

Yeah.

[Paul English]

And use it for something dirty, like a travel site.

[Guy Raz]

From npr, It's How I Built this, a show about innovators, entrepreneurs, idealists, and the stories behind the movements they built. I'm 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 $2 billion. 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 Cuban 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 2004, when Paul launched Kayak along with Steve Haffner, 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 to Priceline for $1.8 billion. 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 his family and they all shared a cramped three bedroom house.

[Paul English]

Yeah, the brothers, the four boys 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.

[Guy Raz]

Wow.

[Paul English]

And so we each had a 15 minute spot slot starting at like 5am 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 5:30am 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 that's how we grew up.

[Guy Raz]

What does your dad do for a living?

[Paul English]

My dad was a pipe fitter. He worked for the Same company for 49 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.

[Guy Raz]

Was he physically imposing?

[Paul English]

It's interesting. I have this one story about my dad. He wasn't like a huge guy. He was probably 6ft tall, 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, you son beat up my son, and 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 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.

[Guy Raz]

Your mom, I guess, was a teacher and a social worker. But from what I read, she spent like the first 10 years of your life actually sick. I mean, do you remember being aware of that and cognizant of her being ill?

[Paul English]

Yeah. My mom had an illness called myosinogravis, which is a debilitating muscle disorder. And she spent much of the first 10 years of my life in bed. But my mom had a miraculous recovery back when I was about 10, 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. 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 seemed like she won.

[Guy Raz]

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

[Paul English]

It was difficult during the 70s and 80s, at the end of their lives. My father ended up passing away 2003. So it's been almost 20 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 ended up well. She looked around the room at 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.

[Guy Raz]

Wow.

[Paul English]

Yeah. They were very different people. My mom was an intellectual. She grew up in a very difficult childhood. And my dad was kind of happy. Go lucky he didn't go to college. He was very charming. He was a good storyteller. But they were very, very different. The last, after my dad retired, I think they actually had a lot of nice times together.

[Guy Raz]

Did you go to Mass every Sunday? Did your mom.

[Paul English]

We did. We sure did.

[Guy Raz]

Did she make you go?

[Paul English]

She made us go.

[Guy Raz]

Were you an altar boy?

[Paul English]

I was. Which my teachers didn't believe me after. 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 I'd say, I have to go to detention. I said, I can't. I'm an altar, but I 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 adhd. Maybe. I'm not quite sure. But I'm still amazed. I think, about if there was any anthropologist from another culture who beamed down, you know, to my schools in Boston or really any school and saw that they kept 30 kids in desks for eight hours. It just seems inhuman. Like, who came up with this idea to make kids sit in a chair at a desk for eight hours? It just seems crazy.

[Guy Raz]

Yeah.

[Paul English]

And 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.

[Guy Raz]

But clearly you were very intelligent because you wound up going to Boston Latin. And for people who don't know, I think it's like the oldest high school in the US and there was an exam, or may still be, to get into it. And from what I've read about you, you had one of the highest admission scores to Boston Latin out of thousands of kids who took the test.

[Paul English]

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 I don't know, I guess I would say I had a lot of diverse interests as a student. I won prizes in art and science and music and math. And as a very competitive kid growing up with all those siblings in one house, I think it makes you both collaborative but also competitive.

[Guy Raz]

Yeah, because you're competing for your parents attention.

[Paul English]

Yeah, that's probably. I mean, I don't know if I was thinking about that explicitly as a kid, but that's probably true.

[Guy Raz]

I mean, this is the late 70s, early 80s. Do you remember when you first got exposure to a computer? Because I'm assuming you couldn't afford to have one at home.

[Paul English]

Well, to my surprise and the surprise of my siblings, one year my mother went out and bought a computer called a Commodore VIC 20. I think it was $300, which is a tremendous amount of money back then. And we were shocked that she would spend that money in a 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 kind of 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, this way to make money programming. And that was pretty cool.

[Guy Raz]

And I guess it was around this time that you actually built a video game which would become like your very first company, I guess.

[Paul English]

Yeah. 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 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, and 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, what the sound effect was.

[Guy Raz]

So this game that you wrote, Cupid, you managed to get the attention of a, I guess a company called gba, which you sold a license to them or something like that.

[Paul English]

Yeah, the deal was it was $25,000 up front and then a dollar revenue per game cartridge, which sounds really great, especially for a teenager. The bad news is I licensed a 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 I went on to the next thing.

[Guy Raz]

Did they pay you? I mean, they went under. Did you get all the 25,000 they paid me?

[Paul English]

No, they paid me 5,000 up front. But then they immediately went out of business. So they never even sent me the rest of the 25,000. So all I really made out of

[Guy Raz]

it was 5,000, which in 1982.

[Paul English]

1980 or whatever. It was a lot of money.

[Guy Raz]

Yeah, it's a ton of money, especially for a high school kid. My God. So for college, you end up going to the University of Massachusetts in Boston. And I guess it became pretty clear while you were there that you were going to pursue a career in computers, probably as a programmer or something like that, because I think while you were in college, you already started to do some freelance work for the nascent computer industry that started to grow in and around in the Boston area in the early 80s.

[Paul English]

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 worked for a mini computer company called Data General in an operations research group. I worked 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 tried to change it up and learn about different industries while I was studying for my undergraduate degree.

[Guy Raz]

Man, in the midst of sort of the early part of your career, because I know one of the first things you did when you had your degrees from UMass was you went to go work for a company called Interleaf, which I want to ask you about in a sec. But you got married really young, like 25, 26.

[Paul English]

Yeah. And Gene and I met at age 18 as freshmen at UMass Boston. And we're married at age 25 and

[Guy Raz]

had kids a couple years in.

[Paul English]

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 their parents. I'm divorced now for 15 years, but I'm very friendly with my ex. We live close to each other. We're still very supportive of each other and we're both pretty close to the kids.

[Guy Raz]

All right, so you really. One of the first 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 must have done pretty well because they eventually promoted you to a management role, right?

[Paul English]

Yeah, I started as a programmer and I loved programming. I worked a million 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 a 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 12 VPs, which is double what we should have for a company of this size. So I'm going to fire half the VPs tomorrow. I want you to run engineering in the business units because 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, you're 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 sales force. 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 it was a really fun job for me.

[Guy Raz]

This is a really heady time in Boston Tech. I mean, I mean, deck Digital Equipment, I think it was. Golf is one of the hottest and would become one of the hottest computer companies in the country. And there are a lot of software companies that don't exist anymore. Including Inner Leaf, right? I mean, I don't think Inner Leaf is around anymore, is it?

[Paul English]

It's not. It sold very successfully. I think it was a billion dollar exit to a company called Broad Vision, which is really hot. During the beginning of the Internet, the beginning of the web.

[Guy Raz]

I Should say, did you have any stock options that you had?

[Paul English]

I did, I did. I made, I made my first million when I was, I have to do the math, but I think I was 29 years old.

[Guy Raz]

Wow.

[Paul English]

But I remember after I had vested half my options, which is a million dollars, I then got convinced by a 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 this crazy startup that imploded a year later. And so I learned quickly how startups shouldn't run.

[Guy Raz]

This is called Netcentric, I think, right?

[Paul English]

Exactly. Yeah. We built software back then. This is back in like 1996, maybe 1996, 1997. There's something called a point of presence, which is where all the Internet companies connected users to the Internet. It routed all the traffic from dial up modems to connect to other servers and businesses. And we built software for these point of presence so you could route faxes through the Internet and the beginnings of doing phone calls over the Internet.

[Guy Raz]

All right, so you go and work for this company called Netcentric, a startup which wasn't going to be. You weren't going to stay there long. But I guess while you were there, you either met or you hired two guys who would eventually become pivotal to the rest of your career. A guy named Bill o', Donnell, one guy named Paul Schwenk. You hired them as engineers. Did you meet them?

[Paul English]

I actually met them at Interleaf. And Bill o', Donnell, or Billow as we called him, and Paul Schwenk, or Schwenk as we called him, turned out to be incredibly instrumental in my career. I've been incredibly lucky to work with those guys for decades. So when I went to Netcentric, 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 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 worked together across several companies over decades and they helped all of my companies be very successful.

[Guy Raz]

So here's, I think, kind of an interesting thing that was going on right on the surface. You were very successful. You had been promoted to an executive position at the previous company. You're at a hot startup. And I think around this time in your late 20s, you presumably went to go see a doctor, a psychiatrist, because you were suffering from things that maybe you couldn't fully understand. Depression and anxiety and sleeplessness. And also. Is that right? I mean, what was going on in your life?

[Paul English]

Yeah. So age 25 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 and just kept looking at the windowsill 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 or longer, and then manic episodes where I couldn't sleep. And the mania or hypomania allowed 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, with my friends, I had trouble communicating with other people.

[Guy Raz]

I mean, a lot of young people first experience some types of mental illness in their 20s. There's some reason why maybe it's a combination of where you are in life and how your brain is developing and just this kind of perfect storm of things happening. How did you get to a point where you said, I've got to go see a doctor?

[Paul English]

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.

[Guy Raz]

And did it?

[Paul English]

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 15 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 20 years now. So I'm hoping, knock on wood, that I've licked that with the meds and with other, with meditation and therapy has helped me with that.

[Guy Raz]

All right, so I think you're in your mid-30s and you were at this Internet startup, Netcentric, and I think you stayed there for what, like a year or even, maybe even less than that.

[Paul English]

Yeah, my, it's funny, my memory of my departure was that I was fired. Years, 20 years after that, I met the founder, the CEO again. His name is Sean O'. Sullivan. He's a wonderful guy. Went on to become a very successful investor. And we had breakfast after not seeing each other for 20 years. And we talked about the fact that we had this fight and that I left. I don't remember the final words that happened. 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 very cheap. We spent very little money on computers and office and everything else. We were cheap as we possibly could. The salaries were cheap, and we're all going to 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, their 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.

[Guy Raz]

When we come back in just a moment how Paul founded and then sold his first major company. And then how 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.

[Paul English]

Have you guys heard about this polar bear? He did the Pepsi Challenge and chose Pepsi Zero sugar. Isn't that right, Mr. Bear? Interesting. So in other words, you now know how much taste matters. Incredible. Do you have any techniques we could share with listeners to help them also accept who they really are? Interesting. So meditation, I think. Or he's hungry. It's hard to read polar bears. Let's give it a go. Go out and try Pepsi Zero sugar today. You deserve taste. You deserve Pepsi.

[Guy Raz]

Hey, welcome back to How I Built this. I'm Guy Raz. So it's around 1998 and Paul English has just left his job at a tech startup and he decides to launch his own 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.

[Paul English]

I spent my savings. I remember I was dipping into my 400k at one point and two of my friends put in a little bit of money. But we were a little company, we had 15 employees and it included my three star engineers, Bill O', Donnell, Paul Schwenk, Jeff Rago, and also my friend Jim Giza 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 store down the street didn't have a website yet.

[Guy Raz]

E commerce, it would still be another decade before it really started to take off. This is 98 and this is right before the dot com crash. Were people just racing to put up e commerce sites?

[Paul English]

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 70% 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. Even like your plumber could send you an email with the bill and you could pay that from the email securely. So we built that.

[Guy Raz]

I mean, I think within a year of launching Boston Light software, you got an offer and then were acquired by Intuit. I mean that's really fast.

[Paul English]

Yeah. I mean, the big tech companies all had a voracious appetite for Internet because the big companies saw what was happening. The Internet was going to take over everything. Desktop software is going to die. And they all wanted to do business with us, which I thought, this is great. Then what 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 good group of people and I'm glad I went there.

[Guy Raz]

Yeah, I mean, you sold. They bought it for 33 and a half million dollars.

[Paul English]

Yeah.

[Guy Raz]

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 manager leading up to. And were you what kind of man? I mean, at this point you'd already had some management experience in your previous jobs. You weren't very successful at it at Interleaf, as you admitted. So presumably you were starting to get a little better at it.

[Paul English]

Yeah, I was reading books about it. It's funny, I don't read business books anymore. I rarely read business books, but because this is going to sound like a funny thing to say for someone who's created a lot of companies is I don't actually like business.

[Guy Raz]

Yeah.

[Paul English]

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.

[Guy Raz]

So when you sold to Intuit, which I think most people know is the people behind TurboTax, right?

[Paul English]

Yep. And Quicken Books.

[Guy Raz]

Yeah, books. When you made that sale. Right. I mean, look, this is 99. So you're, I don't know, almost 40. Right. Years old. Late 30s.

[Paul English]

Late 30s, yep.

[Guy Raz]

And you walked away with 8 or 10 million bucks. I mean, there's taxes and all kinds of things. I have to assume it changed your life in some way.

[Paul English]

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 set up the company was I had 2/3, 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 20 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 20 million, I only made 10 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 where I spend a lot of hours a week on philanthropy, starting in my late 30s.

[Guy Raz]

While you were still with Intuit, because I know you stayed there till around 2002. I heard a crazy story that you were supposed to be on flight 11, the flight from Boston to LA that ended up crashing the World Trade center on September 11, 2001, but you had rebooked on a different flight that was cheaper.

[Paul English]

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 gone on the wrong flight. I think Flight 11 was, if I remember correctly, it was $1,400 to $1,800. And it was a corporate travel department that Intuit had to 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 $343 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 5 years old, my mother had died just a few months prior. And as 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.

[Guy Raz]

And he had no idea what he.

[Paul English]

No. No.

[Guy Raz]

Wow. 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.

[Paul English]

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.

[Guy Raz]

Yeah. So I guess in the period after that, I mean, you were juggling a bunch of different things. You were working with your brother on a company that he had founded and you were doing some work advising nonprofits. But also, I think your dad's health was deteriorating and you started to spend a lot of time looking after him. Right.

[Paul English]

I think the main thing during those years was my mom had died in 2001, 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 and take care of your father. To keep up the good work. Actually, I read as I'm not done yet. 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 at that point. And when mom died, I started spending a lot of time with my dad and then ultimately left into it as his condition worsened and became his primary caretaker for about a year, a 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 that was my main occupation during those years.

[Guy Raz]

Wow. I think it was around 2003 that when you joined the VC firm Greylock Partners as their entrepreneur in residence, and presumably when you were doing that, you were looking around for your next big idea. And I guess this is when you meet this guy named Steve Haffner, who we'll get to in a sec about who he is. But first, how did you meet Steve?

[Paul English]

One of my mentors from Interleaf is a guy named Larry Bond, 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 Haffner. He's one of the founders of Orbitz and he wants to start a new company. Would you meet with him?

[Guy Raz]

Orbitz was a travel website. It is a travel website that he had started.

[Paul English]

He was one of the co founders of Orbitz. He ran marketing there.

[Guy Raz]

That was a pretty big website. Did you know Orbitz?

[Paul English]

Yeah, back in 2000. This was the end of Tucson 3 at this point. And the big travel websites back then was Expedia, Orbitz, Travelocity and Priceline. Those are the big four.

[Guy Raz]

So you knew What Orbitz was. And I did. And presumably like, oh, yeah, I'd love to meet the guy.

[Paul English]

Yeah. And Steve had an idea. He was leaving Orbitz after four years, and he was frustrated with Orbitz, 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, Paul's a good tech guy. Maybe Paul can. Steve can go work together. So the partner introduced us. Steve and I went downstairs to Legal Seafoods in Harvard Square for lunch. I think we each had a couple gin and tonics, maybe. Maybe no. Food. 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.

[Guy Raz]

Wait, just to be clear, because Orbitz, at the time, and Expedia, they were selling tickets on their site, presumably only with partners. Partner airlines.

[Paul English]

Correct. Like they didn't have JetBlue at that point, for example. 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.

[Guy Raz]

Okay, I gotcha. Southwest, JetBlue, whoever. Right. Yeah, right. And there was nothing like that out there.

[Paul English]

Not at the time. There were kind of simultaneous with the creation of our company, there was maybe four or five other companies being created at about the same time who had a similar idea. So it was not a novel idea. The idea of saying, google's a search engine. Why isn't there a search engine just for travel? There were a few people thinking about that. But the funny thing about the meeting was I said, I like the idea. 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 20 chief technical officers. And I said, what are you paying? He said, 4% and a buck 50. Like $150,000 a year.

[Guy Raz]

And 4. 4% equity.

[Paul English]

4% equity. I said, that sounds great. I definitely can find someone for that. He said, why don't you do it? And I laughed and I said, no, I just sold my last company to Intuit. I want to create my own company again. He said, what would it take to have you join Me, as co founder, I said, at a minimum, 50. 50. Just kind of joking. And he put his hand across the table and he said, done. And I thought, whoa, I like how bold this guy is.

[Guy Raz]

He went from 4% equity to 50. 50.

[Paul English]

Yeah.

[Guy Raz]

And just like that.

[Paul English]

In a handshake.

[Guy Raz]

Yeah, Handshake.

[Paul English]

Yeah.

[Guy Raz]

But he didn't even know you.

[Paul English]

Steve and I, we each have a lot of weaknesses. But I will say, probably the superpower that Steve and I have is we're really, really fast reads of people. And I could tell quickly that this guy was crazy bright. And I liked how impulsive he was. And I thought, this guy's a entrepreneur. He's a natural born entrepreneur.

[Guy Raz]

That sounds like the gin and tonics talking.

[Paul English]

Yeah, it might have been.

[Guy Raz]

What? What was it? I mean, this was not in your wheelhouse. A travel website, a consumer? Not.

[Paul English]

Yeah, not at all.

[Guy Raz]

But it appealed to you? Something about it appealed to you?

[Paul English]

Yeah, I mean, I. So I. First of all, I love travel. I think I travel about 100,000 miles a year pre pandemic. And the idea that 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 webpage, that was incredibly fun to me.

[Guy Raz]

So when you agreed to do this, presumably the first step was you had to raise money.

[Paul English]

Well, interestingly, Steve and I went upstairs after having a couple 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 5050 partner, and we're each throwing a million dollars in tomorrow. Which he neglected to mention that to me at the lunch. And then he said, the bad news is I'm tearing up that term sheet because 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 Katis put in 5 million, Steve put in a million, I put in a million. And then we started kayak. And the middle. The middle thing we did, immediate thing we did was start recruiting.

[Guy Raz]

Right, sorry. So you raised some. You raised 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 Schwenk, Jeff Rago. Those guys that Jim Giza who worked with you at your previous companies?

[Paul English]

Yeah. So those are the first four phone calls I placed was to those four guys.

[Guy Raz]

And they all said yes?

[Paul English]

They all said yes. And the interesting thing I'LL tell you about my negotiations with Billo. So he was an architect at Intuit 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 400k a year at Intuit. And I recruited him. I said, I'm starting the company. I want you to come work with me. And he said, what's the company? I said, travel. And he said, how much will you pay me? I said, I'll pay you 100k plus 2% of the company.

[Guy Raz]

Yeah.

[Paul English]

And I remember thinking, is he really going to go for this 100k thing? Because he's probably making 400k. I said, I'd love to work with you. And I have three questions. What do you. What's going to be doing? Travel, how much you pay me? 100k and 2. And then 2%. And the third question was, where's the company located? I was fearing I was about to lose him on the salary issue, so I said, you pick the location. So he chose the first office. It turned out to be a very good financial decision for him to get 2% of kayak.

[Guy Raz]

And the office was in Concord, Massachusetts. Right.

[Paul English]

The original office of the first year was in Maynard, Massachusetts, which I was not happy about.

[Guy Raz]

And meantime, Steve Haffner was going to work out of Norwalk, Connecticut, Is that right?

[Paul English]

Exactly.

[Guy Raz]

Is that where he lived?

[Paul English]

He lived, yes. And we had the tech team in Maynard, then Concord, Mass, for many, many years, where Kai still has an office. So tech was up here just outside of Boston, and the commercial team was in Connecticut.

[Guy Raz]

How come you guys split it up in 2004? It wasn't like today. There wasn't Slack and Zoom and all this stuff that's distributed, remote workplace in 2004.

[Paul English]

Yeah. I mean, Steve and I both had made money before, and I wasn't going to move, he wasn't going to move. So we said, let's try it. And it worked out really well.

[Guy Raz]

All right, so you guys 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. But what about design? Were you focused on the actual user experience?

[Paul English]

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 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 10 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, Expedia was epileptic seizure inducing. It was 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.

[Guy Raz]

And by the way, the name Kayak, what's up with that name? It's just a weird name for a travel website.

[Paul English]

We hired a top brand agency in New York City named Wolf Ohlins. And the project, the branding project, was led by a woman named Carol Costello. 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 going to 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 100 names and we narrowed it down to five. The reason I liked Kayak was I liked the letter K. It's a very valuable letter in branding. I liked it was a palindrome spelled the same backwards and forwards. I liked it was only five letters and it meant like freedom. It's just like a great word. And it's very difficult in branding to take a word 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.

[Guy Raz]

What were some of the other names you thought of?

[Paul English]

I'll go in reverse order. Number five was hive.

[Guy Raz]

Not a bad name. Like a hive where you go and get the tickets and get all your stuff.

[Paul English]

The bad thing about it was the bee sting.

[Guy Raz]

Oh, yeah, yeah. You don't get stung in that hive because then your whole vacation's ruined.

[Paul English]

Yeah. Number four was rice because it's ubiquitous, global and simple. Number three was cake because who doesn't like cake?

[Guy Raz]

I like cake, but not for my travel. I don't want cake in my travel.

[Paul English]

Number two was Kayak.

[Guy Raz]

Okay.

[Paul English]

And the first name, the one we really wanted, which we tried to buy and we could not buy the domain Name was Lola.

[Guy Raz]

Huh, huh. Which would come back to. Which would come back to be part of your life later on.

[Paul English]

Yes.

[Guy Raz]

All right, so you, so you bought kayak. And did anybody get on there initially and say, where are the kayaks? Like, where's your kayak gear? Like, what are you doing?

[Paul English]

We literally got hate mail from kayakers. From kayakers, 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.

[Guy Raz]

Yeah.

[Paul English]

And use it for something dirty like a travel site.

[Guy Raz]

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. 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 $7 million, 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 into out into the world.

[Paul English]

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 2004.

[Guy Raz]

And this is just for friends and family to test out.

[Paul English]

Yes.

[Guy Raz]

And how long before you made that public?

[Paul English]

We made it public, I believe in October of 2004.

[Guy Raz]

All right, now you guys had some working capital because you got investment money, but you were like a nobody among giants like Priceline, Expedia, Orbitz. How are you going to even get the word out about Kayak?

[Paul English]

Well, what I used to say in the early days of Kayak is every company in the world only has 10 smartest people. So Expedia, only 10 of them are the 10 smartest. And even though we're much smaller, we have our 10 smartest people, they have their 10 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 Steve and I were both very aggressive recruiters and we thought we can recruit a really extraordinary first 10 person team.

[Guy Raz]

Well, the business model was going to 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 ticket that company or site or hotel would send you a commission. 50 cents. A dollar.

[Paul English]

Exactly.

[Guy Raz]

But how do you. Didn't you have to manually make those? Because if it was a search engine for the entire travel industry, did you have to individually call JetBlue and Delta American and Hilton and Hyatt? Really?

[Paul English]

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.

[Guy Raz]

How did you grow rapidly?

[Paul English]

Just from word of mouth? I mean, believe it or not, in the early years of Kayak, it cost us about a dollar on average to buy someone to come to our website. From us spending Money on Google, AdWords or 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 the next time they buy travel, will they go directly to kayak.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 70% of the traffic on Kayak was self directed, meaning someone typed kayak.com in their browser. And as soon as that Traffic grew from 0%, 10 to 20 to 30 to 40% and more, then the economics started working.

[Guy Raz]

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, the Marriotts, and said, look, we can show you how people are already going to your site through Kayak.

[Paul English]

Exactly.

[Guy Raz]

And that's how you would convince them to say, okay, fine, we'll pay you 50 cents or a dollar for every time that happens.

[Paul English]

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 Orbitz early on. Steve again was one of the founders there. He was friends with the CEO. We were able to negotiate it with Orbitz to say, when you see a result from American Airlines, we give people the option, click here to go to AA.com to buy it or Click here to go to Orbitz to buy it. And Orbitz would pay us. We base said, we're a little company. We're a new business model with search only. You, Orbit, should participate on this. We'll give you an exclusive. You're the only agency we're going to let on our site. And maybe we're little, maybe we're going to 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 Orbitz. Wouldn't you rather sell them through AA.com and we used Orbitz as a stalking horse to get all the airlines to pay us directly so we could send people directly to the airline sites.

[Guy Raz]

Wow. Did you see Orbitz as a competitor?

[Paul English]

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 literally just a thin search engine. We used on the back end another search engine called ITA Software, which later became Google Flights. And my friends at ITA used to make fun of Kayak. They said, Kayak is a joke. It just sits on everyone else's technology and all. Kayak is a thin UI layer. And my response to that was exactly.

[Guy Raz]

You were the user interface on. You were basically like a skin on top of really sophisticated technology.

[Paul English]

Yes.

[Guy Raz]

That somebody else built.

[Paul English]

But 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.

[Guy Raz]

I mean, that's brilliant. So you didn't actually need to have a massive staff.

[Paul English]

No.

[Guy Raz]

How many people by 2006, 2007 were working at Kayak?

[Paul English]

I think by the time things started growing, we were maybe 50 or 60 people. The best people, like in terms of quantitative people. Stat at Kayak is when we took it public 2012, we only had 200 employees, which is pretty small for public company. And we had 300 million in revenue. So it was one and a half million per employee. We were crazy profitable and fast growing.

[Guy Raz]

Because you were so lean.

[Paul English]

Very, very lean.

[Guy Raz]

All right, 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 around the time you raised that money, that 200 million?

[Paul English]

It was before that. I mean, there were several milestones for us the day 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, 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.

[Guy Raz]

Wow. What about your mental health? How were you doing at that time?

[Paul English]

I think 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 sketchbook with colored pencils and sometimes I'd wake up at 4am and I'd draw pictures of what I wanted Kai to look like, like for a new feature. And I would email them to our head designer, Lincoln Jackson, and then we get a meeting. And so I remember once we took a drawing that I did at 3 or 4am we had a meeting with myself, Lincoln and Jeff Rago, who's our lead developer. And then Lincoln cranked out a Photoshop version 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'd each contribute ideas. And I remember during that time period I felt completely manic. Things are moving very, very rapidly.

[Guy Raz]

I read there was a, 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, because you're just an ideas machine and. Or hey, why don't you try this? And there was a joke among some of the team who were loyal to you, but there was a joke that they would ignore your emails and because they, you would just forget about it over time. And that when you found out about it actually initially it hurt your feelings.

[Paul English]

It did. I'm probably guilty of sending too much email, particularly when I'm in my, you know, creative or hypomanic 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 going to do something unless Paul asks 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 and that I always want to push forward in multiple ideas. But I was both amused by it when I heard this, but also a little bit sad.

[Guy Raz]

Yeah. Because basically 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.

[Paul English]

Yeah, I think so. And I think it's fine for someone to have like nine terrible ideas as long as the tenth one is really big. Failure is okay. We built a lot of technology at COG that we threw 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.

[Guy Raz]

You know what's so interesting is that this insight that you had, because I think previous companies that you had started, I would, and correct me if I'm wrong, but I think that the back end technology was probably more complex 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.

[Paul English]

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 going to know us is we're going to have all the content on one website. That's what we're going to 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.

[Guy Raz]

Yes.

[Paul English]

Oh, that's a site that's really clean. I like that.

[Guy Raz]

Because that's where you invested your money.

[Paul English]

Yeah. And 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. And what he means is to build something simple takes years.

[Guy Raz]

Yeah. I mean, you are a backend programmer who Essentially built a brand. You weren't building a new technology. You were building a brand new.

[Paul English]

Yeah. When I think of the first 10 years of kayak, I think there were three things. Those three things came together. Really good user experience, really good brand, and really good commercial partnerships.

[Guy Raz]

Yeah. In July of 2012, Kayak went public. I think it raised $1.27 billion on the NASDAQ the day it went public. And by the end of that year, it was announced that Priceline would acquire Kayak for $1.8 billion, which basically, Kayak would be under Priceline's umbrella. I think it's. The trading name is bookings.com or something. Or Bookings.

[Paul English]

Yeah, Booking Holdings.

[Guy Raz]

Bookings Holdings. So, you know, Priceline buys out Kayak, and by the time I think all was said and done, the value of kayak was up 2.1 billion or something. In the book that Tracy Kidder wrote about your life, 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 $500 scotch because everyone's like, we got all this. All this money, and you're sitting there at your, like, cubicle at your desk, just, like, quiet. I don't know what was going on in your head.

[Paul English]

It was a little overwhelming. I mean, my first thought was always how happy I was for the team. We had 200 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 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 deal with them for money.

[Guy Raz]

I mean, I had philanthropy, right? Yeah. Right.

[Paul English]

Not just philanthropy. I had someone show up my house who asked me to pay her mortgage. A lot of people asked me to invest in their business. A lot of nonprofits 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 because 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 kind of 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 more thoughtful 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 I definitely have never become really comfortable with the money part of it.

[Guy Raz]

You basically, in your mind, sounds like you knew that you were not going to continue to work for Priceline.

[Paul English]

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 at Intuit. I wanted to build careers for myself and people and learn skills.

[Guy Raz]

Yeah.

[Paul English]

But when I sold Kayak to Priceline, I felt like 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.

[Guy Raz]

I read that the CEO of Priceline was not happy when you told him that you were leaving.

[Paul English]

He was not happy.

[Guy Raz]

Right. Because they were buying you too.

[Paul English]

Yeah.

[Guy Raz]

They were buying your brain.

[Paul English]

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.

[Guy Raz]

I mean, this was the longest you'd worked on one business, 2004 to 2012, right?

[Paul English]

Yeah, 10 years. It was. It was a total of 10 years. 2014. Yep.

[Guy Raz]

We, we will not have time in the course of this episode to get to all the businesses you've done because that, that would take multi part episodes, like several multi part episodes. But there is one I want to 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 phone number. The best time to call.

[Paul English]

Yeah.

[Guy Raz]

And first of all, as somebody who does multiple things also 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, paul, we need you here. Focus on this. Or maybe Steve was like, hey, did it cause tension at times?

[Paul English]

I mean, Get Human became wildly popular. I created it in 2006 and we got massive media the first year. Yeah, I got covered on every national network and magazine and etc. And sometimes I want to come in to a photo shoot or an interview. I tried to schedule all of those to not happen at Kayak off because I was embarrassed about this side project. It's not that I hit it, I just didn't want to see people be working on it. However, I don't think anyone would ever say that I was a slacker at Kayak because I pushed really hard on design and engineering and performance. But yeah, I did have a couple side projects.

[Guy Raz]

Do you still own it?

[Paul English]

Get Human? Yes, it's a very. It's a small company, very, very profitable, run by two of my friends in Boston, Christian Allen and Jeff Welby. And it's an amazing company.

[Guy Raz]

Wow. How does it make money through advertising? Wow. All right, so you do that in the meantime, then you step down from Kayak and you start to do some teaching at MIT and RISD and a few other places at Harvard Business School. I can't get into everything you've done because you've done so many things. One of the things you then created in 2015 was Lola. You went and bought that site.

[Paul English]

Yes.

[Guy Raz]

This is a travel concierge app. First of all, I'm assuming this is geared towards businesses, right?

[Paul English]

Exactly.

[Guy Raz]

Wasn't there like a non compete when Priceline bought it? That wouldn't allow you to get into the travel business again.

[Paul English]

My non compete ended. It was an 18 month non compete. It ended on July 14, 2015. I incorporated Lola on July 15, 2015.

[Guy Raz]

Nice.

[Paul English]

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, we did a major pivot to say rather than selling travel software to CFOs, saying, We'll reduce your cost of travel, we're going to sell software to CFOs that manages all the money their employees spend. So we call it spend management budgets and spend management. Yeah, we basically manage every penny that your employees spend. What are they spending money on? Google, AdWords, 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 fill in expense support, ever. And we guarantee to the CFO that your team will always be exactly on budget. No one will ever actually go above 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.

[Guy Raz]

Is Lola now your primary focus? Would you say it is?

[Paul English]

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.

[Guy Raz]

One is a podcast discovery app called Moonbeam.

[Paul English]

Yep. Moonbeam fm.

[Guy Raz]

You've got a nonprofit called King Boston that focuses on, like, celebrating the work of Dr. King and his wife, Coretta Scott King. Right. In Boston. You do a lot of work in Haiti.

[Paul English]

Yep.

[Guy Raz]

I mean, here we are coming out of the pandemic and you're what, late 50s?

[Paul English]

I'm 57.

[Guy Raz]

Okay. How many more businesses do you have in you?

[Paul English]

I mean, someday 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 VC backed 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 you have to have the discipline to say no because 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 a lot, 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 color for Lola. And that's Mostly Monday, Friday, 9 to 5. Yellow is non profit 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, what to do in the Thursday nights. 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.

[Guy Raz]

When you think about all the things you've achieved. Right. And the financial success, but really more importantly, just the 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 chalk up to luck?

[Paul English]

I don't like to think of myself as intelligent. I will admit to being creative. I think my success leads to maybe three things. I do think work ethic is 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.

[Guy Raz]

And where do you put luck on that scale?

[Paul English]

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 who really transformed the company. I don't know. Maybe it's those four things. 25% each.

[Guy Raz]

One more thing I want to ask you about, Paul, before I let you go. You have been an Uber driver, right? You signed up to be an Uber driver in your Tesla in Boston, right?

[Paul English]

Yes.

[Guy Raz]

Do you still do that?

[Paul English]

I haven't done it since the pandemic, just because I was nervous about people in my car. But now that I think in Massachusetts now we have over 70% of people are vaccinated. I think when it gets up to 80, 85%, I'm going to start driving again.

[Guy Raz]

Tell me the Uber story. Why did you want to be an Uber driver?

[Paul English]

So the first reason I signed up was at Lola. We have 24. 7 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 1 to 5, 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.

[Guy Raz]

Did any drunk kids ever barf in your Tesla?

[Paul English]

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.

[Guy Raz]

Yeah, you know, on a good Uber night. What are you pulling in?

[Paul English]

I think usually it's about $50 is what I make. Just going out for a couple hours.

[Guy Raz]

It's not bad.

[Paul English]

I think my biggest night, I made $100.

[Guy Raz]

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 Shangchi.com. oh, and just in case he needs them, Paul owns more than 200 domain names, including a whole bunch of words. He just likes the sound of words that could work one day inspire his next big idea. Whale Tale, Zarzan, ez, Mighty Stay Tuna Cloakly 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 [e-mail] if you want to follow us on Twitter. We're How I Built this. Or Me Guy Raz. Our Instagram is How I Built this. NPR and mine is Guy Raz. This episode was produced by Farah Safari and Diba Mota Sham, with music composed by Ramtin Arablouei. It was edited by Neva Grant with research help from Claire Murashima. Our production staff includes Casey Herman, Rachel Faulkner, Liz Metzger, J.C. howard, James Delahousy, and Julia Carney. Our intern is Harrison Vijay Choi. Jeff Rogers is our executive producer. I'm Guy Raz, and you've been listening to How I Built this. This is NPR.