Wondery Plus subscribers can listen to how I built this early and ad-free right now.
Join Wondery Plus in the Wondery app or on Apple podcasts.
Listening on Audible helps your imagination soar.
Whether you listen to stories, motivation, or expert advice, any genre you love, you can be inspired to imagine new worlds, new possibilities, new ways of thinking.
Find the genres you love and discover new ones along the way.
More bestsellers and new releases, plus thousands of included audiobooks, podcasts, and originals that members can listen to all they want, with more added all the time.
Audible makes it easy to be inspired and entertained as part of your daily routine without needing to set aside extra time.
There's more to imagine when you listen.
I just listened to an Audible original from Keegan-Michael Key called The History of Sketch Comedy, and it taught me so much about an art form that I've always been fascinated by.
For an Audible member, you can choose one title a month to keep from the entire catalog, including the latest bestsellers and new releases.
New members can try Audible free for 30 days.
Visit audible.com slash built or text built to 500 500.
That's audible.com slash built or text built to 500 500 to try Audible free for 30 days.
Audible dot com slash built.
There's no distance too far for the perfect trip.
Hi, checking in for… Or the perfect table.
Hey, where are you? Coming!
And when you get access to Resi Priority Notify with your AmEx Platinum card… Hey, this looks amazing!
I'm so glad you made it. And travel benefits at fine hotels and resorts booked through AmEx Travel?
It's worth the trip. That's the powerful backing of American Express.
Terms apply. Learn more at AmericanExpress.com slash with AmEx.
Take your business further with a smart and flexible American Express business gold card.
It offers flexible spending capacity that adapts to your business.
You can also earn up to $395 in annual statement credits on eligible purchases at select business merchants.
That's the powerful backing of American Express.
Terms apply. Learn more at AmericanExpress.com slash business gold card.
Hey, it's Guy here. So it's summer and I'm on vacation.
And maybe you're traveling right now as well.
And if you are, you might have booked your plane ticket or hotel on the website created by today's guest, Paul English.
Paul built the travel website Kayak and lots of other companies as well.
He is the ultimate serial entrepreneur.
So stick around because at the end of the show, I'll have a quick update about what he's been up to since this episode first ran back in 2021.
Okay, here's the show. We hired a top brand agency in New York City named Wolf-Oleens.
The branding project was led by a woman named Kara Costello.
Actually her team came up with a list of about a hundred names and Kayak was actually our second choice.
All right, so you've bought Kayak and did anybody get on there initially and say, where are the Kayaks?
Where's your Kayak gear?
What are you doing? We literally got hate mail from Kayakers.
From Kayakers, yeah. We said this was terrible that we took this over and this is like a blight on the internet that someone would take over their precious hobby and use it for something dirty like a travel site.
Welcome to How I Built This, a show about innovators, entrepreneurs, idealists, and the stories behind the movements they built.
I'm Guy Razz 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 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 to price line 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.
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.
Wow. And so we each had a 15 minute slot starting at like 5am or something.
And if you missed your slot, you'd be going to high school smelly.
So 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.
What was your, what does your dad do for a living?
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.
Was he physically imposing?
It's interesting. I have this one story about my dad.
He wasn't like a huge guy.
He's probably six feet 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.
My father opens the door and there's this huge guy and he said, you're a son beat up my son and blah, blah, blah.
And my father put his finger in 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.
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?
Yeah. My mom had an illness called myocinagravus, 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.
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.
That's amazing. What do you remember about your parents' marriage?
What was it like? It was difficult during the seventies and eighties at the end of their lives.
My father ended up passing away in 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 I'm a mother's death bed 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.
Wow. Yeah. They were very different people.
My mom was an intellect.
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.
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 altar boy? I was.
My teachers didn't believe me.
I had many times I get 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 boy.
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 an anthropologist from another culture who beamed down 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.
Who came up with this idea to make kids sit in a chair at a desk for eight hours?
It just seems crazy. I couldn't do it.
I struggled with that. I did like performing intellectually.
I worked really hard at music and science, things like that, but my grades were terrible.
Clearly, you were very intelligent because you wound up going to Boston Latin.
For people who don't know, I think it's the oldest high school in the US and there was an exam or may still be to get into it.
From what I've read about you had one of the highest admission scores to Boston Latin out of thousands of kids who took the test.
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.
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.
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, because you're competing for your parents' attention.
Yeah, that's probably, I don't know if I was thinking about that explicitly as a kid, but that's probably true.
This is the late 70s, early 80s.
Do you remember when you first got exposure to a computer?
I'm assuming you couldn't afford to have one at home.
To my surprise and the surprise of my siblings, one year, my mother went out and bought a computer called the Commodore Vic-20.
I think it was $300, which is a tremendous amount of money back then.
We were shocked that she would spend that money on the computer.
I still don't know why she bought it.
She must have seen an ad somewhere and thought this could be a good way to entertain the kids.
I selfishly took it over.
I learned everything I could.
I learned how to code. I wrote software.
I wrote a video game. Not to me taught me, whoa, this way to make money programming.
That was pretty cool. I guess it was around this time that you actually built a video game, which would become your very first company, I guess.
Yeah. I called my little company Speed Games.
It's funny to call it a company because I don't think I was incorporated.
The game that I sold was called Cupid.
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.
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.
This game that you wrote, Cupid, you managed to get the attention of a company called GBA, which you sold a license to, to them or something like that?
Yeah, the deal was it was $25,000 upfront and then a dollar revenue per game cartridge, which sounds really great, especially for a teenager.
The bad news is I licensed the game to them and they immediately went out of business.
The question is, why didn't I then go contact every other game publisher to try to find someone else to license it?
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 onto something else.
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.
Did they pay you? I mean, they went under, did you get all the $25,000?
They paid me $5,000 upfront, but then they immediately went out of business.
They never even sent me the rest of the $25,000, so all I really made out of it was $5,000.
Which in 1982, 1980 or whatever, there was a lot of money.
It was 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 why you were there that you were going to pursue a career in computers probably as a programmer or something like that because I think why 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.
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.
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.
Yeah. And Jean and I met at age 18 as freshmen at UMass Boston and we're married at age 25.
And had kids a couple years in and...
We had two kids. Yeah. I have a son and a daughter.
My daughter's Nicole and my son is Michael and they both live in Boston and they're super close to both the 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.
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.
Yeah. And you were a program there and you must have done pretty well because they eventually promoted you to a management role, right?
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 have 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.
This is a really heady time in Boston Tech.
I mean, I mean, deck, digital equipment, I think it was called, 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 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 a company called BroadVision, which is really hot during the beginning of the internet, or the beginning of the web, I should say.
Did you have any stock options that you had?
I did. I did. I made my first million when I was, I have to do the math, but I think I was 29 years old.
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 with 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.
This is called Netscentric, I think, right?
Exactly. Yeah. Back then, this is back in like 1996, maybe, 1996, 1997, there was something called a point of presence, which is where all the internet companies connected users to the internet.
It routed all the traffic from dialect 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.
All right, so you go and work for this company called Netscentric, the 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 Schwank.
You hired them as engineers.
Did you meet them there?
I actually met them at Interleaf.
And Bill O'Donnell, a Bill-O, as we called him, and Paul Schwank, or Schwank 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 Netscentric, 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.
So here's, I think, kind of an interesting thing that was going on.
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?
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 switched 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 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 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.
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.
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?
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 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 therapies helped me with that.
All right, so I think you're in your mid 30s and you were at this internet startup, NetCentric.
And I think you stay there for what, like a year or even maybe even less than that.
Yeah, 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 Osalov.
And 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.
So 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 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 size 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, the new salary.
I had the CFO literally sign it because I want 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.
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 Ross and you're listening to How I Built This.
This podcast is sponsored by Squarespace.
Squarespace is the all in one website platform that so many of the entrepreneurs I talked to use, in fact, I use it as well.
Whether you're just starting out or managing a growing brand, Squarespace makes it easy to create a beautiful website, to engage with your audience and sell anything from products to content to time, all in one place, all on your terms.
Start a completely personalized website with the new guided design system, Squarespace Blueprint.
Choose from professionally curated layout and styling options to build a unique online presence tailored to your business and optimized for every device.
Get discovered fast with integrated SEO tools so you show up more often to more people and grow the way you want.
And make checkout seamless with simple but powerful payment tools, except credit cards, PayPal and Apple Pay.
And in eligible countries, offer customers the option to buy now and pay later with afterpay and clearpay.
You could even sell exclusive content on your site by adding a paywall to sell memberships or courses.
So head to squarespace.com for a free trial, and when you're ready to launch, go to squarespace.com slash built to save 10% of your first purchase of a website or domain.
Say goodbye to performance robbing engine deposits with Shell V Power Nitro Plus Premium gasoline.
In case you didn't already know, lower grade fuel can leave deposits in your engine that build up over time and leave your engine's performance severely lacking.
But thankfully, Shell V Power Nitro Plus removes up to 100% of performance robbing deposits with continuous use in gasoline direct injection engine fuel injectors.
Download the Shell app today to find your nearest Shell V Power Nitro Plus station and rejuvenate your engine with Shell V Power Nitro Plus Premium gasoline.
Fuel up at Shell. My favorite spring cleaning takeaway is the post-clean clarity you get.
Wow, how have I been living like this?
It's kind of like when you find out that you've been paying a fortune for wireless when Mint Mobile has phone plans for $15 a month when you purchase a three-month plan.
It's time to switch to Mint Mobile and get unlimited talk, text, and data for $15 a month.
Over a year ago, I ditched our family's overpriced wireless contract and the unexpected over age fees we got billed every month.
To get this new customer offer and your new three-month unlimited wireless plan for just $15 a month, go to mintmobile.com.built.
Cut your wireless bill to $15 a month at mintmobile.com.built.
$45 upfront payment required equivalent to $15 per month.
New customers on first three-month plan only.
Lead slower above 40 gigabytes on unlimited plan, additional taxes fees, and restrictions apply.
See Mint Mobile for details.
Hey, welcome back to How I Built This.
I'm Guy Razz. So it's around 1998 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 into my 401k 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 Schwank, Jeff Rago, and also my friend Jim Guiza and Carl Barry.
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 your average store down 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 1998. And this is right before the dot-com crash.
Were people just racing to put up e-commerce sites?
Mostly we 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.
Why would a little bookstore create their own website?
It didn't make sense to them.
It's like, that's not for us.
That's our 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. I mean, I think within a year of launching Boston Light Software, you got an offer and then we're acquired by Intuit.
I mean, that's really fast.
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.
And 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.
Yeah. I mean, they bought it for $33.5 million a year, about a year after you launched it, which you basically signed a contract presumably and worked there for a couple of years and became a manager leading up to it.
And were you, what kind of, 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.
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 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.
Yeah. I mean, to me, creating a company is 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 I think most people know is the people behind Turbo Tax, right?
Yeah. And Quicken. Quicken.
Yeah. Quicken. Quicken.
Yeah. It's $1.99. So you're, I don't know, almost 40, right?
Years old, late 30s. Late 30s.
Yeah. And you walked away with eight 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.
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 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.
While you were still with Intuit, because I know you stayed there until 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 in the World Trade Center on September 11, 2001, 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, maybe I would have gotten 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 that booked flights.
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 to lay over, but I felt proud that I saved the company money as 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 his 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. 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.
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 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 on time looking after him, right?
I think the main thing during those years was my mom had died in 2001 and literally on her death bed as she sang bye to each of us.
The thing she said to me was, keep up the good work and take care of your father.
The 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.
Wow. I think it was around, 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 Hafner, who we'll get to in a sec about who he is.
But first, how did you meet Steve?
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 Hafner.
He's one of the founders of Orbitz.
And he wants a start in the company.
Would you meet with him?
Orbitz was a travel website.
It is a travel website that he had started.
He was one of the co-founders of Orbitz.
He ran marketing there.
That was a pretty big website.
Did you know Orbitz? Yeah.
Back in 2000, this was the end of Tucson, there's a three at this point.
And the big travel websites back then was Expedia, Orbitz, Travelosv and Priceline.
Those are the big four. So you knew what Orbitz was.
I did. And presumably like, oh yeah, I'd love to meet the guy.
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 of gin and tonics maybe.
Even 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 Orbitz at the time and Expedia, they were selling tickets on their site, presumably only with partners, partner airlines.
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. Okay, I got you.
Southwest, JetBlue, whoever, right?
Yeah. Right. And there was nothing like that out there?
Not at the time. There were kind of simultaneous with the creation of our company.
It was maybe four or five of the 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 is their 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?
I said, 4% and a buck 50, like $150,000 a year.
And 4% equity. 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.
He went from 4% equity to 50-50 and just like that.
And a handshake. Yeah. 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 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 an entrepreneur.
He's a natural born entrepreneur.
It sounds like the gin and tonic's talking.
Yeah, it might have been.
What was it? I mean, this was not in your wheelhouse.
A travel was it? No, not at all.
Yeah. Not at all. But it appealed to you.
Something about it appealed to you.
Yeah. I mean, so first of all, I love travel.
I think I traveled 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.
So when you agreed to do this, presumably the first step was you had to raise money.
Well, interestingly, Steve and I went upstairs after having a 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 50-50 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 Catalyst 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 was start recruiting.
Right. Sorry. So 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 had worked with you at your previous companies?
Yeah. So those are the first four phone calls I placed 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 Bill O.
So he was an architect added into it because he, again, he and I worked together for decades.
So he was at Boston Light, we sold to Intuit, he became an architected Intuit.
I'm guessing by memory, he was probably making 400K a year at Intuit.
And I recruited him, I said, I'm starting with a company, I want you to come work with me.
And he said, what's the company?
I said, travel. And he said, how much do you pay me?
I said, I'll pay you 100K plus 2% of the company.
And I remember thinking, is he really going to go for this 100K thing?
Because he's probably making 400K.
He said, I'd love to work with you again.
I have three questions.
What's the company doing?
Travel. How much do you pay me?
100K and then 2%. 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.
It turned out to be a very good financial decision for him to get 2% of kayak.
And 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 going to work out of Norwalk, Connecticut.
Is that right? Exactly.
Is that where he lived? He lived, yes.
And we had the tech team in Maynard, then 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?
I mean, 2004, it wasn't like today.
It wasn't Slack and Zoom and all this stuff.
Like that's a distributed remote workplace in 2004.
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.
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 build these things.
You know how to code, you know how to run engineers.
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 video game back when I was in high school, I focused 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 going to be hard to beat this because to me Expedia was epileptic seizure inducing.
I mean, 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.
And by the way, the name Kayak, what's up with that name?
It's just a weird name for a travel website.
We hired a top brand agency in New York City named Wolf Olands and the branding project was led by a woman named Kara 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 lose their products?
We spent a lot of time talking to 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 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.
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 beasting.
Oh yeah. Yeah. You don't get stung in that hive because then your whole vacation's ruined.
Yeah. Number four was Rice because it's ubiquitous, global and simple.
Hmm. Number three was Cake because who doesn't like cake?
I like cake but not for my travel.
I don't want cake on my travel.
Number two was 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.
Huh. Huh. Which would come back to be part of your life, Lidran.
Yes. Alright, 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?
We literally got hate mail from Kayakers.
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, Hapal 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 Raws and you're listening to How I Built This.
Quick math. The less your business spends on operations, on multiple systems, on delivering your product or service, the more margin you have and the more money you keep.
So with higher expenses on materials, employees, distribution and borrowing, everything costs more.
So to reduce costs and headaches, smart businesses are graduating to NetSuite by Oracle.
NetSuite is the number one cloud financial system bringing accounting, financial management, inventory and HR into one platform and one source of truth.
With NetSuite, you reduce IT costs because NetSuite lives in the cloud with no hardware required.
You cut the cost of maintaining multiple systems because you've got one unified business management suite.
And you improve efficiency by bringing all your major business processes into one platform, slashing manual tasks and errors.
Over 37,000 companies have already made the move.
So do the math. See how you'll profit with NetSuite.
And by popular demand, NetSuite has extended its one-of-a-kind flexible financing program for a few more weeks.
That's netsuite.com slash built.
That's netsuite.com slash built.
One more time. That's netsuite.com slash built.
We've all heard Abraham Lincoln quoting the proverb, good things come to those who wait.
But that's actually only part of the quote.
The full quote is, good things come to those who wait, but only the things left by those who hustle.
Well, if you're a business owner and want the best people on your team, the same applies.
Thankfully, ZipRecruiter puts the hustle in your hiring.
So you find qualified candidates fast.
And now you can try it for free at ziprecruiter.com slash built.
ZipRecruiter's smart technology finds top talent for your roles right away.
Right after you post your job, ZipRecruiter's matching technology starts showing you qualified people for it.
I've actually tried it in my own business and it's amazing.
So let ZipRecruiter give you the hiring hustle you need.
See why four out of five employers who post on ZipRecruiter get a quality candidate within the first day.
Just go to ziprecruiter.com slash built to try it for free.
Again, that's ziprecruiter.com slash built.
ZipRecruiter, the smartest way to hire.
Hey, welcome back to How I Built This.
I'm Guy Razz. 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 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 2004.
And this was just for friends and family to test out.
And how long before you made that public?
We made it public, I believe, in October of 2004.
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?
Well, what I used to say in 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 know 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.
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.
Exactly. And didn't you have to manually like make those, because if it was a search engine for the entire travel industry, did you have to individually call JetBlue 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 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 cost us about a dollar on average to buy someone to come to our website for spending money on Google AdWords or other websites.
We made on average 20 cents per user.
So we were losing 80 cents of transaction in large numbers.
We were losing a lot of money very quickly.
But if you build a really amazing website and you paid having come here, will they remember this word Kayak and the next time they'll buy travel, will they go directly to Kayak.com without having to go to Google for us?
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 the browser.
And as soon as that traffic grew from 0%, 10% to 20%, to 30%, to 40% and 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, the Marriottes.
They'd look, we can show you how people are already going to your site through Kayak.
Exactly. And convince them to say, OK, fine, we'll pay you 50 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, 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 basically 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 Orbits.
And you rather sell them through a.com.
And we used Orbits as a stocking 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 you're playing was late, call the airline, don't call us.
We were just, we were 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 IT used to make fun of Kayak.
They said, Kayak is a joke.
It just sits on everyone else's technology.
And all Kayak 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 really sophisticated technology.
Yes. That somebody else built.
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.
I mean, that's, that's brilliant.
So you didn't actually need to have a massive staff.
No. How many people by 2006, 2007 were working at Kayak?
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 in 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.
Because you were so lean.
Very, very lean. All right.
So I guess three years in, three and a half years in December, 2007, you raised a big fund raise, $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 are now a player in this space?
Was it, was it around the time you raised that money, that 200 million?
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.
Wow. What about your, what about your mental health?
Were you, 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 sketchbook with colored pencils.
And sometimes I'd wake up at 4 a.m.
and I'd draw pictures of what I wanted kayak 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 4 a.m.
We had a meeting with myself, Lincoln, and Jeff Rago, 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 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, they, you would just forget about it over time and that when you found out about it, actually initially it hurts your feelings.
It did. I'm probably guilty of sending too much email, particularly when I'm in my, you know, creative or hypomanic states.
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.
Let's 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, that I was going to push forward in multiple ideas, but I was both amused by it when I heard this, but also a little bit sad.
Yeah. Cause 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.
Yeah. I think so. And I think it's fine for someone to have like nine terrible ideas as long as the 10th one is really big.
Failure is okay. We built a lot of technology at CIG 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.
We did it many times at Kayak.
You know, it's so interesting is that this insight that you had, because I think you, previous companies that you had started, I would, and correct me if I'm wrong, but I think that the backend 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 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 the site that's really fast.
Yes. Yeah. Oh, that's the site that's really clean.
So I like that. Because that's where you invested your money.
Yeah. And it was a huge investment.
Becoming fast is not easy.
Something simple is not easy.
Scott Cookin' and Tuit used to say, it's very easy to build complicated software.
And what he means is to build something simple takes years.
Yeah. I mean, you are a back-end 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 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.
Yeah. In July of 2012, Kayak went public.
I think it raised $1.27 billion on the NASDAQ that today 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 the trading name is bookings.com or something, or bookings.
Yeah, booking holdings.
Bookings holdings. So Priceline buys out Kayak.
And by the time I think it all was said and done, the value of Kayak was at $2.1 billion or something.
In the book that Tracy Kitter wrote about your life, there's a scene where the news breaks inside of Kayak's headquarters, people are so excited.
Everybody's passing around a bottle of $500 scotch because everyone's like, we got all this money and you're sitting there at your cubicle at your desk just like quiet.
I don't know. But 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 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 sent a retention.
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 requests for money.
For philanthropy, right?
Not just philanthropy.
I had someone show up in 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.
You basically in your mind, sounds like you knew that you were not going to continue to work for Priceline.
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.
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.
I read that the CEO of Priceline was not happy when you told him that you were leaving.
He was not happy. Right, because 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 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, 2004, 2012, right?
Yeah, 10 years. It was a total of 10 years, 2014.
We will not have time in the course of this episode to get to all the businesses you've done because that would take a multi-part episode, 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 if you want to find a human customer service rep, you can find their phone number, the best time to call.
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 causes 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?
I mean, Get Human became wildly popular.
I created it in 2006. And we got massive media the first year.
I got covered on every national network and magazine and et cetera.
And sometimes I want to come in and do a photo shoot or an interview.
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 at 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 small company, very, very profitable, run by two of my friends in Boston, Christian Allen and Jeff Welpey.
And it's an amazing company.
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.
This is a travel concierge app.
Exactly. So you're like a non-compete when Price Line bought it that wouldn't allow you to get into the travel business again?
My non-compete ended, it was an 18-month non-compete.
It ended on July 14, 2015.
I incorporated Lola on July 15, 2015.
Nice. 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.
You have got a nonprofit called King Boston that focuses on like celebrating the work of Dr.
King and his wife, Coretta Scott King in Boston.
You do a lot of work in Haiti.
Yeah. I mean, how many more businesses do you have in you?
I think for the rest of my life, rather than doing a VC-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 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, 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, night to five.
Blue 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, which I do on 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.
When you think about all the things you've achieved, right, and you know, 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 check up to luck?
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.
And where do you put luck on that scale?
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 transform the company.
I don't know, maybe it's those four things, 25% each.
One more thing I want to ask you about, Paul, before I let you go.
You have been an Uber driver.
You signed up to be an Uber driver in your Tesla in Boston, right?
Yes. 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 24-7 customer support.
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.
On 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. On a good Uber night, what are you pulling in?
I think usually it's about $50 is what I make.
Just going out for a couple hours.
It's not bad. I think my biggest night I made $100.
Nice. That's Paul English, occasional Uber driver and founder or co-founder of, among other things, Kayak, Lola.com, Moonbeam Intermute, GetHumans, SpeedGames, Boston Light Software, and the online Chinese chess site, Xiangqi.
Since we first published this episode back in 2021, as you can probably imagine, a lot has changed for Paul.
Actually, not long after this episode first came out, Lola.com, the travel site that Paul launched after Kayak was acquired by Capital One and the site shut down.
But then a couple years later, Paul co-founded a new company using the Lola name.
This time, it's a dating app that matches people based on their availability to meet up in real life, cutting out the online chit chat and getting to the in-person date faster.
Lola dating just launched in Boston in May of 2024 with plans to expand to more cities soon.
Thanks so much for listening to this show this week.
Please make sure to click the follow button on your podcast app so you never miss a new episode of the show.
And as always, it's free.
And please don't forget to sign up for my free newsletter at GuyRoz.com.
I promise to make it worth your time.
This episode was produced by Ferrah Safari and Diba Motasham with music composed by Ramteen Ereblewe.
It was edited by Neva Grant with research help from Claire Murashima.
Our production staff also includes Chris Mussini, J.C.
Howard, Casey Herman, Alex Chung, Catherine Seifer, Sam Paulson, Kerry Thompson, John Isabella, Carla Estevez, and Elaine Coates.
I'm Guy Roz and you've been listening to How I Built This.
If you like How I Built This, you can listen early and add free right now by joining Wondery Plus in the Wondery app or on Apple podcasts.
Prime members can listen ad-free on Amazon Music.
Before you go, tell us about yourself by filling out a short survey at Wondery.com Hi, I'm Lindsay Graham, the host of Wondery's podcast American Scandal.
In our latest season, we retraced the greatest corruption scheme in US history as we bring to life the bribes and backroom deals that spawn the teapot dome scandal, resulting in the first presidential cabinet member going to prison.
Follow American Scandal on the Wondery app or wherever you get your podcasts.
You can binge this season American Scandal teapot dome early and add free right now on Wondery Plus.
And after you listen to American Scandal, go deeper and get more to the story with Wondery's other top history podcasts, including American history tellers, Legacy and even the Royals.
