KAYAK: Paul English (2021)

27:28I 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.

28:06I had the CFO literally sign it because I wanted evidence that these were approved. And then I told the engineers, you're getting a raise. And Sean and I got a huge fight over it. His memory was that I quit. My memory is that he fired me, and I ended up leaving the company because of it. Why don't we come back in just a moment, how Paul founded and then sold his first major company. And then, 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.

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32:17Hey, 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 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 4K 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 Barry.

33:02That 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. 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? 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?

33:47It didn'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. I mean, I think within a year of launching Boston Light Software, you got an offer and then were acquired by Intuit.

34:25I 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 then when it turned out is the more time we spent with them they actually all wanted to acquire us they just wanted the talent they wanted the engineers and i made the decision to go with intuit because I like the culture. I like the values. I just thought it was a good group of people. And I'm glad I went there.

35:00Yeah. I mean, you sold it. 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. 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.

35:43Yeah. 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. 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 TurboTax, right? Yep. And Quicken. And Quicken. Yeah. Quicken. Yeah. 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. Late 30s, yeah. And you walked away with eight or 10 million bucks.

36:27I 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 at 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.

37:01So 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 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.

37:47Yeah, I don't tell that story often because I know people that actually died that day, and I just had, you know, maybe I would have gotten on the wrong flight. I think flight 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 five years old, my mother had died just a few months prior.

38:26And 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. And he had no idea. 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.

39:24So hopefully I'm fully present today because none of us know what our future is. Yeah. 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? I think the main thing during those years was my mom had died in 2001 and Literally on her deathbed 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.

40:12Actually. I read as i'm not done yet Like I haven't won over my parents yet. 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 to 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 2003 that when you joined the VC firm Greylock Partners as they're entrepreneur-in-residence.

40:57And 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.

41:44His name is Steve Hafner. He's one of the founders of Orbitz, and he wants to start a new company. Would you meet with him? Orbitz was a travel website, 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, big website. Did you know Orbitz? Yeah, back in 2000, this was the end of 2003 at this point. And the big travel websites back then was Expedia, Orbitz, Travelocity, and Priceline. Those are the big four. So you knew what Orbitz was. I did. And presumably you're like, oh yeah, I'd love to meet the guy. Yeah. And Steve had an idea.

42:18He was leaving Orbitz after four years. and he was frustrated with orbits and he had an idea of a different way to do travel but he was looking for a CTO, a chief technical officer. And this other partner at General Catalyst thought, I don't know, Paul's a good tech guy, maybe Paul and Steve can go work together. So the partner introduced us, Steve and I went downstairs to Legal Seafoods at Harvard Square for lunch. I think we each had a couple of gin and tonics maybe, maybe no food. And he gave me the pitch and he basically said, I want to create a search engine for travel, a search engine that has the stuff from everyone else's website.

42:56And 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.

43:26Southwest, 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. 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 is 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.

44:04It's like 20 chief technical officers. And I said what are you paying? He said 4 % and$1.50, 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? Yeah.

44:39And just like that? And a handshake. 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. That sounds like the gin and tonic's talking. Yeah, it might have been. what what was it i mean this was not in your wheelhouse a travel website a consumer not at all yeah not at all uh but it appealed to you something about it appealed to you yeah i mean i so i 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 web page that was incredibly fun to me.

45:39So 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 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.

46:18But anyway, General Catalyst put in 5 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 talk about my negotiations with Bill O.

46:56So 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. 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, and I have three questions.

47:33What'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 him on the Sarely 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?

48:05He lived, yes. And we had the tech team in Maine and 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? In 2004, it wasn't like today. There wasn't Slack and Zoom and all this stuff. Like that's 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.

48:43What 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.

49:18I 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 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 but by the way the name kayak what's up with that name? It's just a weird name for a travel website.

49:55We hired a top brand agency in New York City named Wolf Ohlins. And 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? She had a lot of time I'm 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 like the letter K. It's a very valuable letter in branding.

50:30I liked it was a palindrome spelled the same backwards and forwards. I liked it was only five letters. And it meant like freedom, which is like a great word. And it's very difficult in branding to take a word 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 bee sting. Oh yeah. Yeah. You don't get stung in that hive because then your whole vacation's ruined.

51:09Yeah. Number four was Rice because it's ubiquitous, global, and simple. 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 later on. Yes. All right, 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, yeah, who said this was terrible that we took this over.

51:57And this is like a blight on the Internet, you know, that someone would take over their precious hobby and use it for something dirty like a travel site. When we come back in just a moment, how Paul found out that the much-resented name for his new business was becoming one of the more popular search terms on the internet. Stay with us. I'm Guy Raz, and you're listening to How I Built This. The holidays are upon us, and businesses are hiring for seasonal roles. Everything from haunted corn maze workers to snowplow drivers. This means that people with certain skills, experience, or even a special license are in high demand and not easy to find.

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54:08Hey, 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 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? Yes. 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.

55:05How are you going to even get the word out about Kayak? Well, what I used to say in the early days of kayak is every company in the world only has 10, 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 that 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.

55:46Well, the business model was going to be different because Expedia, 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. But 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 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.

56:26It's one of these things, sort of ask for forgiveness, not permission. We're just moving as fast as we possibly could. So we just scraped websites. It took us about a year, year and a half till the software felt really good. And then we started growing rapidly. How did you grow rapidly? Just from word of mouth. I mean, believe it or not, in the early years of Kayak, it 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.

57:02We 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'll buy travel, will they go directly to kayak.com without having to go to Google first? 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. 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 and say, look, we can show you how people are already going to your site through Kayak.

57:54Exactly. 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. 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 aid.com to buy it. or click here to go to Orbitz to buy it, and Orbitz would pay us.

58:27We just said, we're a little company. We're a new business model. We're search only. You, Orbitz, 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.

59:00So we could send people directly to the airline sites. Wow. Did you see Orbitz as a competitor? Well, they were different flavors than us. They were a merchant. But we used to say, search with us, book with them. We didn't have customer support. If your plane was late, call the airline, don't call us. We were 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 is a thin UI layer.

59:35And my response to 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 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 2012, we only had 200 employees, which is pretty small for a public company, and we had 300 million in revenue.

1:00:24So it was 1.5 million per employee. Wow. 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 fundraise,$200 million. Sequoia leads that round, Sequoia Capital. And that means you can really get – you can now do things like acquire other companies and launch a big advertising campaign. When did you feel like you were now a player in this space? Was it around the time you raised that money, that$200 million? It was before that. I mean there were several milestones for us.

1:01:05The 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 mental health? How were you doing at that time? I think at that point, I had pretty much controlled the depression.

1:01:45So 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'd 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.

1:02:26But 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. I read 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. Or, hey, why don't you try this?

1:03:00And there was a joke among some of the team who are loyal to you, but there was a joke that they would ignore your emails because you would just forget about it over time. And that when you found out about it, actually, initially, it hurt your feelings. It did. I'm probably guilty of sending too much email, particularly when I'm in my 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.

1:03:44And 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. Yeah, because basically it confirms that you are an ideas machine. You're a little bit manic. And 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 COG that we threw away.

1:04:24We 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. 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. That's right. It's interesting.

1:04:58When 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. Oh, that's a site that's really clean. So I like that. Because that's where you invested your money. Yeah, and it was a huge investment. Becoming fast is not easy.

1:05:31Becoming 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. 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.

1:06:12Today 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 the trading name is bookings.com or something or bookings. Yeah, Booking Holdings. Bookings, holdings. So, you know, Priceline buys out Kayak. And by the time I think it 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 money.

1:07:00and you're sitting there at your cubicle at your desk, just quiet. I don't know. 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 center of attention. There's certain advantages to it. Like it helps me raise money.

1:07:39It helps me hire people, but I'm a little bit uncomfortable with it. And when we started getting a lot of press after the IPO and after the acquisition, I started getting a lot of incoming requests and I didn't know how to do with them for money. I mean, I had philanthropy, right? Yeah. Right. Not just philanthropy. I had someone show up my house who asked me to pay her mortgage. 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.

1:08:19But 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.

1:08:55I 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. 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.

1:09:33I 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, yeah. We will not have time in the course of this episode to get to all the businesses you've done because that would take multi-part episodes, like several multi-part episodes.

1:10:15But 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 GetHuman, 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. Yeah. 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, you know, Paul, like, we need you here. Like, focus on this.

1:10:51Or maybe Steve was like, hey, you know, I mean, did it cause tension at times? I mean, Get Human became wildly popular. I created it in 2006. Yeah. 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 Offics. 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.

1:11:36But yeah, I did have a couple of side projects. Do you still own it? GetHuman, yes. It's a small company, very, very profitable, run by two of my friends in Boston, Christian Allen and Jeff Welpe, 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 kink into everything you've done because you've done so many things. But one of the things you then created in 2015 was Lola. You went and bought that site.

1:12:18This is a travel concierge app. Exactly. Wasn't there like a non-compete when Priceline 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 non-profits, and then I have two other small startups that I run on the weekends. You have got a non-profit called King Boston that focuses on celebrating the work of Dr. King and his wife, Coretta Scott King, right in Boston. You do a lot of work in Haiti. Yep. I mean, how many more businesses do you have in you?

1:13:01I 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, 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.

1:13:42So purple is Lola, which is, that's the brand color for Lola. And that's mostly Monday, Friday, nine to five. Yellow is nonprofit work, which is about eight hours a week. Green is self-improvement, which is going to the gym or going to therapy or going to my Buddhist class, which I do on Thursday nights. And then blue is everything else that are 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.

1:14:22How much of that do you attribute to your intelligence and hard work and how much do you chalk 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.

1:15:02And 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 transformed 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, right? 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.

1:15:46But at the end of every interaction in the Lola app, when you've talked with one of our service people, you get to rate them, like on a scale of one to five, how well is the service they did for you. But before I inflicted that upon our customer service people, I wanted to show that, okay, I'm happy to get rated. I want to see what it feels like to get rated. Being an Uber driver was the easiest way to do that because you get real-time feedback. In the driver app, you get feedback every day about how your rating is. Did any drunk kids ever barf in your Tesla? Thank God, no. I had a rule that when I would drive at night, as soon as I got the first drunk, I would stop driving.

1:16:21I didn't want to take that risk. Yeah. You know, 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. That'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, Get Humans, Speed Games, 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.

1:17:12But then a couple of 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.

1:17:39Thanks so much for listening to the 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 Farah Safari and Deiba Motasham with music composed by Ramtin Ereblui It was edited by Neva Grant with research help from Claire Murashima Our production staff also includes Chris Messini, JC Howard, Casey Herman Alex Chung, Catherine Seifer Sam Paulson, Kerry Thompson John Isabella, Carla Estevez and Elaine Coates I'm Guy Raz, and you've been listening to How I Built This.

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