How I Sold Kayak.com For $2 Billion | Paul English Interview (#394)

Paul English

I think a lot of people say it's harder because you don't have the edge; you don't work as hard. That's not true with me. If you talk to anyone who works with me, they'll say I'm working as hard now as I was during my first company when I was blowing through my 401(k) to finance it.

Sam Parr

Alright, Paul, what's going on, man? Well, Dharmesh, CTO and co-founder of HubSpot, told us we have to... we don't have to, but we should talk to you. Why did he say that?

Paul English

I don't know if it's going to be connected, but Dharmesh and I have a lot of fun talking together about technology, philosophy, and teams. One fun thing that Dharmesh and I did, going back many years ago now, when I was CTO and co-founder of Kayak, is that Dharmesh and I switched jobs for a day. I actually had him made up; I got him an email address, [email protected], and made up business cards. He basically sat at my desk at Kayak for a day, and then I sat at HubSpot for a day. That was sort of the beginning of our friendship, realizing that we each had some overlap but also some things we could learn from each other. He's been a great mentor to me and a friend.

Sam Parr

And your big hit has been, well, so far you have a new company, Lola. I don't know if you know this or not, but you guys advertised with my old company, The Hustle, a bit. So, yep, we worked with you a bit. But your big hit so far has been Kayak. Right? What did you sell that for? Like $2 or $3 billion?

Paul English

I have actually sold 6 companies in a row, including Lola. I've sold even another one after Lola, called Moonbeam, which is a podcast app. Now, I'm on to my 7th company.

Sam Parr

Which one of the six has been the most financially successful for you?

Paul English

**Kitek** was the biggest financial outcome, which I'm deeply appreciative of. I learned a lot at Kitek and met some amazing people. But there are other things which are also really significant that aren't just monetary. For example, my first sale... I don't have to... I just told you I sold six in a row. There's another one that I don't really count because it was only a company I created in high school, but it's very meaningful to me: making money in high school designing software.

Sam Parr

and what were the 6

Paul English

So, I had a company called **Boston Lite**. We were an e-commerce company that let people set up storefronts, a little bit like Shopify, but this was back 20 years ago. We sold that to **Intuit**. I then became the VP of Technology for Intuit. After that, I had a company called **Intimute**, which was internet security software. I did that with my brother, Ed English. We sold that to **Trend Micro**. I also started a company called **GetHuman.com**, which has served customer service information to over 200 million people. Then there was **Kayak**, **Moonbeam** (the podcast player), and **Lola**, which is for business travel and expense. Did I forget one? I think that's the list.

Shaan Puri

And so, what's the thought process? Did you start them all in kind of the same way? Were you maybe scratching your own itch, or were you analyzing trends? So, what's your process to come up with these ideas?

Paul English

It's mostly scratching my own itch. I'm not going to go through company by company. The only one that wasn't my original idea was Karayak. My co-founder, Steve Hafner, was one of the founders of Orbitz. He had observed that Orbitz said 70% of the people did a search on Orbitz, but then when they were done, they opened a second browser and went directly to United.com or wherever to buy the ticket. So, Orbitz did all the searching for people but never made money. Steve said, "Why don't we create a company where all we do is search? If someone wants to go to United, they click the link, and we'll send them directly to United so they can buy a fare." That was his observation. We met by chance, and within probably 45 minutes, we decided to sign up as co-founders. Each of us put $1,000,000 into the original round of financing. From a product standpoint, I went, "I'm about to spend an hour on Expedia that night," because Expedia was the market leader at that time. I just went back the next morning saying, "This isn't going to be hard." I looked at Expedia as bloatware; it was sort of seizure-inducing. There was so much stuff going on on the screen.

Shaan Puri

You put $1,000,000 in. Was that like a "I'm putting all my chips on the table" right now? Or was that, you know, half your net worth? Was that a small bet for you? How did you feel at that time? Did that add some anxieties to the process?

Paul English

I just sold a company for **$30,000,000**, so I could've... the million wasn't that hard for me at that. My prior company that I sold for **$30,000,000**, I blew through my 401(k) to finance it. So, my first company was tough financially to get going, but for Kayak, I had made some money, so I could afford to help finance it.

Sam Parr

Why did you sell your companies? Why not try to run them or have them exist under a management team that you control for a long time?

Shaan Puri

like dharmesh right darmesh has been doing hubspot for forever

Paul English

Yeah, so Kayak, I did for 10 years. That was my longest stint. We ended up taking it public in 2012, which was incredibly fun. Then we sold it shortly thereafter to the parent company, Booking.com. I just frankly was bored. I felt like I was editing the flight screen for 10 years, and I wanted to try something new. I had an unbelievably strong team in tech leadership at Kayak, so I felt like I could sneak out without hurting the company. I had people there who could do UI, product, and architecture, so it gave me the freedom to try something new.

Sam Parr

You’re kind of, I mean, you’re like an internet OG a little bit. I mean, Kayak is one of the, was like a pretty huge thing. It still is a huge thing, but in terms of internet exits, it was early on in the game. You guys had a nice, huge exit. Who are some of the people who are kind of like big shots and ballers now that you got to know a little bit earlier on?

Paul English

you mean across the industry overall

Sam Parr

Yeah, because like Dharmesh has all these crazy stories where he's like, "You know, I was an early investor in Coinbase." I met the team and I thought, well, he didn't actually tell me this. I'm just making it up. I mean, he did invest in Coinbase, but I'm sure there's a story. He's like, "Well, I met this guy Brian, and he was living out of a closet and doing all this weird stuff." He was a quirky guy. I mean, he just has met... or I believe he was an early investor in Dropbox as well. He probably has all these interesting stories about some of these folks who are now like tycoons or a big deal now. But he was fortunate because he's a little bit older and was more successful than they were when they were just getting their things started. That gave him insight into these businesses. Do you have anything like that?

Paul English

Yeah, so I met Brian Chesky at Airbnb when they were financing a $1,000,000,000 valuation. I think the net worth was $100,000,000,000 or something like that. I remember at the time loving Brian; I thought he was iconic and passion-driven, mission-driven. But I didn't see how big it was going to get. I said, "This seems awesome for people, one of strangers living in a house," but how many people is that going to be? So I kind of missed the bigger picture there.

Sam Parr

what was he like when you met him just get like

Paul English

he was I mean

Sam Parr

I've seen him talk. My wife works there. I totally agree; I think he is an icon. I think he's one of the best CEOs out there. He's passion-driven; he's amazing. But what did you see?

Paul English

I saw him as very serious and intense. He was charismatic and listened well. We had a good conversation where he wanted me to give him feedback on the company because Kaggle was a much bigger company at that time. Overall, I took him as very serious, intense, and charismatic.

Shaan Puri

Yeah, whenever you're doing technology for like 15 or 20 years, you just get this crazy story arc. You know, you get to see people. You see all these people that you're like, "Alright, I think this person is kind of amazing. They might go on to do amazing things. Maybe it's this idea, maybe it's the next idea." Are there any other stories like that that you've seen? Because you've been kind of in the game for such a long time.

Paul English

Yeah, so when we financed, Kak was created in 2004. We really launched out of General Catalyst in Cambridge, Massachusetts. Then we raised money from Mike Moritz at Sequoia. I remember one day my co-founder and I were working out of Square's office, and Mike Moritz said, "Oh, I wanted to introduce you to a couple of guys. This is Chad Hurley, and that's his co-founder." They were the founders of YouTube.

Sam Parr

steve chen I think

Paul English

Yeah, that's right. I remember meeting those guys in a square office, and Mike's like, "Yeah, these guys are putting videos online." I'm like, "Yeah, that's cool, whatever." I didn't see that one either. I have some famous misses. I mean, I've been very lucky as an investor. I think my IRR is 30.5% over the last several years, so I've been pretty good. I've invested in 60 companies, but I've missed some. I missed Snapchat. I met one of their founders when they were financing at an $80,000,000 valuation. That would have been a big outcome. Dropbox, I met Drew early on, and that wasn't under the guise of me investing in them. It was really just networking. But had I... I thought Dropbox was going to be plagued by security issues. I'm still shocked I use Dropbox. Do you know that they don't really encrypt your files? A Dropbox engineer, if they're malicious, can get at just your files. Yeah, I believe that. It's amazing that they're as big as they are, and why doesn't anyone worry about that?

Sam Parr

What have been the hits so far? You said you've invested in 60 companies and you have this great IR (Investor Relations). What have been some of the successes?

Paul English

one of the ones coming up right now is pilot.com

Sam Parr

I use and

Paul English

Yeah, that's an amazing company. I met those guys when I was a judge at the MIT 100K competition. They had a company called Ksplice, which had really exotic technology. They could patch a Linux operating system while it was running, so you didn't have to reboot your servers. They sold that to Oracle. I was part of that competition, and I helped them win. Then, I invested in their next company, Zula, which they ended up selling to Dropbox. When they left Dropbox to create another company, I basically asked if I could invest before I knew what they were working on. So, I wrote them a check before I knew what they were doing, and that's a 40x return. I think I financed them with a check as part of the round at a $30,000,000 valuation. Their last valuation was around $1,200,000,000 or something. But that's one where the founding team had the mojo. When you met them, you just knew those guys were going to create something serious. They were intense, high energy, they laughed a lot, and they finished each other's sentences. They just really enjoyed working together. Another good return for me was Kensho, which is a competitor to a Bloomberg terminal. I invested in them because their CTO, Pete Cresco, used to work at Kayak, and I knew him from Kayak. I just knew he was destined to do great things, and that was a really nice exit.

Sam Parr

We had this guy, Trung, work for us. Trung was an analyst at Kensho, which is still a startup. From an outsider's perspective, they kind of fit the stereotype of an uptight financial firm. We found Trung working there. This guy, Trung, who works for us, is a loudmouth—literally! He speaks so loud and is full of energy. He was a writer for us, and we taught him how to use Twitter. Now, he's got like 1,000,000 followers on Twitter. We recruited him from Kensho.

Paul English

that's amazing

Sam Parr

I like kensho because of that thank you

Shaan Puri

And you, so Kayak was a big win. Then you did things like, let's say, Moonbeam, which is a podcast discovery type of app. It could have been big, but I think anything in podcasting looks sort of niche. Most of the podcast products that win are really good lifestyle businesses. So far, there haven't been that many big winners in the podcasting space in terms of tools. I know one thing that's hard: I've talked to people who have had an exit of $700 million, $800 million, or even $1 billion. That becomes the new table stakes for the next thing they do. Some go that way and say, "Okay, I gotta get huge now," while others are like, "No, I'm literally just going to program things in my house for fun now." They don't want to try to catch lightning in a bottle again. Which way do you think about it? Or is there another third way? Again, which way do you think about it? Or is there another third way?

Paul English

I've always said for each of my companies, it's **team first**, **customer second**, and **profit third**. I set this for Kayak on day one when we put together our culture plan. I really think it's a good way to execute because if you focus on becoming a phenomenal recruiter and really becoming a student of recruiting—like reading all the books, listening to the podcasts, and learning from others who talk about recruiting—you can recruit an amazing team. Then, figure out how to lead that team so that there's no stress in the office. People work really hard, they have fun, they're cranking stuff out, but they're not stressing each other out. If you do those things, you can create... I always say **magic teams create magical products**. Then usually, if you can create a magical product, you can find a profitable business there. For me now, after I sold Lola, my business travel and expense company, to Capital One a year ago, I then opened up a venture studio called **Boston Venture Studio** (bvs.net). We have nine apps under development. Some of them are "itch to scratch"—like fun little things that we put out with source code. Others are a swing for the fences; I really think they can become big. There's a company I launched two weeks ago called **Deets** (like "show me the deets") that could be a **$1,000,000,000** company. What we're doing is saying online reviews are broken. You know, if you go to Google right now and in quotes you search for "buy Amazon reviews," you'll see 37,000 pages that tell you how to do that. If you make, you know, these headphones I'm wearing, and you make a competitor of these and you want to sell it on Amazon, you can easily buy a 1,000 five-star reviews for that if you want. These fake review companies are run by PhD computer scientists, and they're evading Amazon's bot detection, so it's very difficult at this point.

Paul English

To detect them, they're going through proxy servers. They have aged accounts and buy products. If you go to Yelp or TripAdvisor, their reviews are largely by people you don't care about. For example, I looked up a sushi restaurant in New York and saw 5-star reviews of this place. People talked about how great it was because it's really cheap. I don't know about you, if you like sushi or not, but I'm not sure I'm going to be that excited about having $10 sushi per person in New York. That's a little scary to me.

Sam Parr

also catfish and cream cheese roll

Paul English

Yeah, if you go on TripAdvisor and you look for hotels, you'll see a lot of 5-star reviews from Motel 6. That was great when I was 20 years old, but I'm not sure I would stay at a Motel 6 now. A lot of you just don't relate to the person doing the purchasing. So, the idea of Deets is going to blow that up and say it's just the recommendations from your friends and from influencers that you choose to follow. Then, using machine learning and look-alike modeling, we can find people that are similar to you.

Sam Parr

Man, it seems like you pick really hard industries. Travel is, you know, again, I'm an outsider; you're the expert. But it seems notoriously difficult. It just seems incredibly competitive and very, very challenging. The margins seem small, making it hard to start one of those things. Now, podcasting is terribly hard. I don't entirely understand why it's so difficult, but nothing has entirely clicked to make it this fantastic industry, even though a lot of people use podcasts. Then reviews also seem terribly challenging. You know, Yelp hasn't innovated in 5 or 10 years; their stock sucks. Google Reviews is a horribly challenging platform to compete with because they have all these people already using it. What's the game plan here? And why are you picking the hardest things to work on?

Hubspot

yeah the origin of the deets is I I'm friends with some people who own restaurants in boston and I saw the difficulty they had during covid and so it really developed some compassion for restaurant owners and they all told me how much they hey yelp yelp is just like mafia where you pay if you they call you and they save a lot of bad reviews call us and pay us 100 of dollars a month and we'll sort of clean up your site on yelp it's kinda like in italy there's a movie called $1,000,000,000 bully about yelp it came out in 2019 and the opening scene is an italian chef who said when he opened his first restaurant in italy someone broke the windows he fixed them they broke them then the next week he fixed them the next week some guy comes in and says I noticed someone keeps breaking the windows if you're paying me a $100 a week I'll make sure no one breaks the windows anymore and he knew that was the guy who's breaking the windows he's like yelp was just like that so I look at yelp as a 20 year old dinosaur that's the last 20 years we wanna be the next 20 years and I look at the evolution you know the world is different now than it was when the yelp was created for 1 the rise of the influencers particularly gen z they make all their purchase decision based on influencers and that's true not for dining so we want to give it make it really easy rather than scrolling through instagram and trying to find an old post of a restaurant you saw a month ago having it in one tight really clean ui it's your friends it's your influencers and then on machine learning I'm really inspired by tiktok tiktok's an amazing app they don't ask you any questions they don't say what's your interest but if you look at my tiktok feed there's a lot of bass players I'm a bad bass player but I like bass players there's a lot of dogs I have a new dog there's gardening tiktok has figured out the stuff I'm interested in and without ever asking me question and the way they work is they don't even ask you who your friends are they will find some you know dj in berlin who has the same weird sense of humor as you and they'll show you these are the videos she listens to or that she watches so I really like that lookalike modeling or user clustering so we're doing that with deets as well you're gonna find your friends the influences you like and then people of the same taste as you this data is wrong every freaking time have you heard of hubspot hubspot is a crm platform where everything is fully integrated woah I can see the client's whole history calls support tickets emails and here's a task from 3 days ago I totally missed hubspot grow better do you

Sam Parr

Do you think that starting a company now that you're wealthy is easier or harder than when you were just getting going in your career?

Paul English

I think a lot of people say it's harder because you don't have the edge; you don't work as hard. That's not true with me. If you talk to anyone who works with me, they'll say I'm working as hard now as I was during my first company when I was blowing through my 401(k) to finance it. To me, working hard is about recruiting hard, leading, coaching people, and getting them excited. I'm working on that as hard as I ever have. I'm trying to get a little bit better with each company. There is some advantage to having money. If you see a stupid problem that costs $5 to fix, you know when you're creating your first company, you don't have that $5. Now you do, so you just pay a little money and problems go away.

Sam Parr

what do you think sean easier or harder

Shaan Puri

Yeah, I think it's different, and you just have to work with the pros and the cons. Right? Like, yeah, recruiting is easier, and you waste less time on just the rookie mistakes that you always make. But then, you know, there is some diminishment, maybe, of the edge. The things that made you successful the first time might have been that there was a technology wave going on, or there was a bunch of opportunity. You have to recognize new technology waves or new inflection points—new things that have changed. Like, you know, he's talking about how basically machine learning has gotten a lot better. Now we can do things that make the user experience way different. Before, we had to ask you 50 questions to show you something good, and now you could swipe 3 or 4 times, and I could start getting you something good. I can create a delightful user experience, whereas before, maybe I couldn't. So, I think it's different, and the things he's saying make a lot of sense to me. I'm going to tell you one...

Paul English

The thing about doing tech now versus 20 years ago is that I've been investing for a long time in addition to running companies. In the old days, companies would fail because their product didn't work; they just couldn't get the tech working. That's hardly the case now. The stack, the AWS, the tools, the open source—it's pretty easy to assemble the right libraries and find the right people to help put something together. Companies fail today for one of two reasons: 1. There's a founder implosion, and they create a toxic culture where people hate their boss and hate working there. Unfortunately, this happens all too often. They fail the culture code. 2. They build a nice product, but it's a problem that no one cares about. Unfortunately, a lot of founders have an itch to scratch, as you were saying earlier, Sam. They get really obsessed about it, thinking, "I have this little problem; I'm going to work on it for 10 years." They don't realize that not a lot of people have that same problem. It makes me sad when I see that—a beautiful product that solves a problem I don't care about.

Shaan Puri

Yeah, you see that all the time. That's like the number one cause of death, I think, with startups. You said something a second ago that I wanted to ask you about. So, you go become amazing at recruiting. That's never been something that I was like, "That's the thing I'm gonna set my mind to." You said, "I read all the books, I listened to all the podcasts, and tried to become amazing at this so I can assemble teams to do your venture studio."

Sam Parr

and you're pretty good at it though sean

Shaan Puri

Well, I'm just like, I don't know. You never know, right? Like, even whatever you know, it's like a belt system. It's like, even if I'm a blue belt, there's still a black belt, you know, that I could go learn from. Even if you're a black belt, they're like, "Oh, I'm just..." There's lifetimes more to learn about this thing. But I'm curious, Paul. How would you summarize for somebody who's talented but hasn't put their focus on becoming great at recruiting? What do you think are the, give me like the 80/20, the summary of what principles you think are most important when it comes to recruiting? Are there any that you wouldn't expect? Are they all just things like, "I want to lose weight, it's like eat healthy and exercise." Like, okay, well, you know, I guess that's true, but it's not that helpful. I kind of already do that. Are there any things that are maybe counterintuitive or nuanced that are important?

Paul English

The main thing is to just **recruit all the time**. Always, always be recruiting and always be trying to connect with people. You might be going to a coffee social to learn about why crypto is terrible or whatever, and you don't realize that someone is going to be there who could be your next unbelievable CMO. You weren't expecting to meet them, but if you always have your spidey sense out for looking for amazing people, then once you see them, do whatever it takes to get them to come meet your team. I have a little bit of an off-color story, which I probably shouldn't tell, but someone asked me once about my new strategy.

Sam Parr

by the way that's the best starting of a story so

Shaan Puri

go ahead I'm I'm I like perked up

Paul English

Okay, so someone asked me about my recruiting style. If you've been recruited by me, you'll know that I'm very, very aggressive. I do whatever it takes to get you. I'll come meet you at a Starbucks near you; I'll do it just to get my team. I've trained my team on how they should behave in their first meeting with you. The first thing that came to mind when someone asked me about this—about why I'm so laser-focused on getting these people—was a moment from 7th grade at Boston Latin School. I was at my locker when this really cute girl walked by. My friend noticed me turn my head and look at her. He said, "English, don't even think about it. She's dating the captain of the football team." At that moment, that girl went in color, and the rest of my world was black and white. I had to date that girl just because my friend said I couldn't. And I did end up dating her. So, when I recruit and I see someone amazing, I'll always ask them, "Do you know anyone even more amazing than you?" I did a funny Japanese game show where a guy in Italy was looking for the most beautiful woman in the world. When he encounters the first beautiful woman in Italy, he says to her, "Do you know anyone more beautiful than you?" This leads to a hilarious succession of conversations. When I'm recruiting and I find someone amazing, I'll do what it takes to get them excited and to get them to meet my team. I've always said that the first five people hire you; the next 50 who hire you, and then the next 500. It's one thing as a founder to convince someone to come meet your company, but if you've been really good at recruiting those first five, those five will close the candidate for you. When they meet those five, they'll say, "Oh my God, I need to work with this team."

Sam Parr

You kind of have... I'm clicking around on your site. You and Dharmesh are interesting to me because you guys have this dry, almost nerdy sense of humor that I love. For example, if you go to **lola.com**, it basically says the domain's for sale, but you can see the history of Lola by clicking here. It goes to **pmd.org**, and it's a website where it's just plain text explaining exactly what happens. That's kind of an interesting way of explaining the story. But if you click **paulenglish.com**, it goes to your website and talks about some of your cool investments, your founder stories, and things like that. It also lists all the clubs you're involved in, and one of them looks like either you started or you are part of the **Bipolar Social Club**. I was reading on your Wikipedia that you had some issues with bipolar disorder, and I think that the fact that you're part of the Bipolar Social Club is... that's pretty funny, you know? I like guys like you and Dharmesh. It's why I love Dharmesh. He's this guy who's like... you talk to him and you're like, "Oh, you're just shy." But then you start talking to him a little more, and it's like, "Oh, you might be quiet, but you're kind of a killer." He's incredibly quirky. For example, he's got a new project called **venndiagram.com**, which is a community for people who love Venn diagrams. Then he has another thing called **Wordplay** or something like that, which is like a Wordle game that makes like $100 a month or something crazy like that. He just has all these things. You kind of seem like that. Are you a guy who's just constantly tinkering on stuff?

Paul English

Yeah, I mean, I own about 300 domain names, and every domain name has a Google Doc associated with the idea for the company. I'm obsessed with branding and names. Dharmesh and I share this; we're prepared to spend big money to buy a good name. I have lectured at a lot of universities, giving a lecture on where creativity comes from. I've done this every day, from Berkeley School of Music, Dartmouth Film School, Brown, and the Rhode Island School of Design, as well as the more traditional universities you would think about. What I do is, let's say I'm teaching Thursday at 5 o'clock. On Wednesday at 5 o'clock, I'll have the professor email the students and say, "Take a picture of something tonight that annoys you." Not a picture you took yesterday, not a picture you found on Google, but take a picture of something tonight that annoys you. Then, I teach the students about how irritation becomes inspiration and how any problem can become the motivation for a product. We go through a very specific exercise about how to do that. I am someone who loves ideating. They say that you're the average of the five people you spend most of your time with. If you want to change your life, change the people you spend time with. If you look at the people I hang out with, they care about nonprofit work, philosophy, and ideating—like improving things. I just have a blast meeting with people like Dharmesh and saying, "How can we fix this? How can we do this better?"

Shaan Puri

Well, you're in the right spot. When we started this podcast, it was doing alright. Maybe, I don't know, 10,000 people would listen to every episode, so maybe like 100,000 in a month, something like that. It was a classic interview show, similar to what we kind of have done so far—getting to know you a little bit. It was like, "Oh, you built Kayak? Amazing! Tell me about it. How'd you do it?" It was just like every other tech or business podcast, which is a "how would you do it" podcast. Then one day, just to mix it up, I invited Sam on. I said, "Sam, let's just shoot the shit like we do when we're not on a podcast." We talked about things like, "Oh, have you seen this? Yo, why doesn't somebody solve this? Dude, I tried to book this the other day; it was so annoying." We just started brainstorming. We turned the podcast into what we called the "$1,000,000 Brainstorm," which is basically ideas that we don't have the time to do, but they were ideas that we thought could be like, you know, $1,000,000 or even $1,000,000,000 ideas. That's what we did, and then the whole podcast took off. Now it's in the top ranks of the charts and all this stuff. I think it's because we switched into this ideating brainstorm mode. There are a lot of people like us out there. Just like Dharmesh is trying to find all the Venn diagrammers out there, all the inventors, we're trying to find all the people that love to shoot the shit and brainstorm ideas. Sounds like you're one of them! So can you give us a couple of ideas? Maybe pull three names and what's the one-line pitch you have in mind for some ideas that you'll probably never have time to go do?

Paul English

sure I'll tell you some ones that the itch was enough that I actually did a little bit of work on it so one of them was I live in boston but I also spend a lot of time in new york where I am today and where I live is kind of between west village and tribeca near soho and I don't know new york that well like I know the those three neighborhoods but I don't really know like upper east side upper west side whatever if I'm trying to meet someone on the upper west side I don't know where to meet I'm like this is annoying that there isn't a website where they can see where they are where I am and pick a bar in the middle so I built an app it's called middle.net I went and bought that domain name and middle.net allows you to have 2 people or 3 or 4 as many as you want it grabs your location from the browser and it shows you like a coffee shop or bar to meet in the middle now I'm never gonna make any money doing that but I did it just because I needed to know where to meet people in new york because I was getting used to the city I couldn't find a way to do it so I built an app another one when you meet someone so I generally don't really like going to conferences because I'm a little bit shy a little introverted I've like learned how to be extroverted and I can say more about that if you care to hear about it but when you do go to a conference and you meet someone and you wanna swap info it's annoying to do it you know you gotta type in phone numbers and stuff you gotta type in email addresses so dumb or we can use this dot card thing but you have to carry this card around this card around so I designed a little app called funcontact it's funcontact.com and allows you to have a list of qr codes one qr code might be just my email another one might be my email my home address and based on who I'm meeting what information I wanna share them I just swipe through and show them the right qr code they scan it and I'm in their address book I built that because I needed it I don't think it'll ever become a company but I just wanted that so I built it

Sam Parr

how many people are using this this looks cool I'll use it I was I just needed one of those things the other day

Paul English

It's super cool! I used it last night. Oh, do you want to hear a funny story? Yeah, so last night was my 3-year anniversary with my girlfriend, Rachel. We went to San Ambrose in the West Village, where we had our first date three years ago. Next to us was Anna Wintour, if you know who she is—the editor of Vogue magazine and one of the top socialites in New York. Bradley Cooper sat next to us on our first date. Last night, on our third anniversary, we went to the same restaurant, and guess who was sitting next to us? Anna Wintour! That was super cool. At the end of the evening, I did talk to her for a couple of minutes, and then she left. The table on the other side of me had four people who work in the fashion industry, where my girlfriend works. We really kind of bonded and talked about the Bipolar Social Club and the clothing brand I want to create. Then they asked for my number, and I just pulled out a fun contact and scanned it. Now all these young fashion people have my number, and we've been messaging each other today about the Bipolar Social Club.

Shaan Puri

that's great what's the clothing brand you wanna create so bipolar

Paul English

I have bipolar illness. I was diagnosed at age 25, and it's a pretty serious illness. You know, a lot of people end up killing themselves or ruining their marriage, their job, or their lives. It took me a good 10 to 15 years to learn how to manage it for myself. It's bipolar 1 and bipolar 2. I'm bipolar 2, so I'm not the most severe type. The most severe type has voices and they end up homeless, or worse. Not that there are a lot of things for us in being homeless, but bipolar 1 is a pretty serious illness. Bipolar 2 still has problems, but over the years, I learned how to deal with it. I want to be able to laugh with other people who are bipolar about the funny things related to being bipolar. So, I created this video series. If you go to **bipolarsocialclub.org**, there are 10 people with bipolar illness who share their journeys. It's kind of destigmatizing it. It's saying, "Yeah, it's a mental illness, and there are some shitty things about it, but there are some funny things about it too." I have this thing about bipolar people: if I'm at a cocktail party with 100 people and there's someone on the other side of the room, I can tell they're bipolar. We recognize each other. My gay friends say they have "gaydar"; they can tell gay people across the room. I can tell bipolar people across the room. We're trying to do something fun. We want to have a clothing brand where bipolar people can wear the brand proudly, like "Bipolar and Proud." So, **Bipolar Social Club**—we want just sort of a fun name.

Sam Parr

Is there anything in the travel industry that you noticed? I mean, because you had more data than... There's probably only hundreds of people in the world, or maybe low digit thousands, that are able to kind of see some of the things that you saw because of the scale of Kayak and the company that bought you guys. Were there any interesting problems that you felt weren't being entirely solved that you think could actually be quite large, you know, big businesses?

Paul English

The problem with the travel industry, and the thing I have the most trouble with, is flights and airports. TSA... TSA is a joke. The stuff they do to you gives you a false sense of security, but there's no real security with TSA. That's irritating. I wish someone would solve that and make something a lot more efficient and safer. Airlines are running on old technology. They have to be very conservative because if they make a mistake and adopt something too new, the plane will crash. Obviously, they don't want that to happen, so it's very archaic and old. As I said earlier, I travel between Boston and New York. I never fly because by the time you go through TSA security and get an Uber at each end, it's often faster to drive. As far as things in the travel industry that I would like to see fixed, I'd like to see someone figure out how to work with all the unions that put all these requirements in, who work on the airlines, how to work with TSA, and how to make flying pleasurable. It's not pleasurable now. I also remember growing up when you would go to the airport, people used to dress up. They were really excited to get on a plane to travel. But now, airports are just a nightmare, and I wish someone could make airports pleasant and make flying pleasant.

Sam Parr

yeah same it sounds like the hardest thing on earth to do though

Shaan Puri

What do you think about what Elon is doing? So, Elon buys Twitter. He's kind of taken this technology-first approach. He's trying to change the culture overnight, force people back in the office, lay off a bunch of people, and try to ship changes really fast. It seems a little bit helter-skelter. Have you followed that? I'm curious about your opinion as a CTO and someone who's done tech for a long time.

Paul English

I followed it quite closely and I was put on the list of a thousand people who want to create a Twitter competitor. Right now, I've been spending a bunch of time in the last week ruminating on that, and I think it's a bit of a shit show. I always knew that Elon Musk was eccentric, and I forgave him for some of his stupid stuff just because he creates such good products. I love my Tesla cars, and I'm a happy Tesla stockholder from 2016. But when I looked at the way he fired people at Twitter, it was just obnoxious as hell. Like, do you really need to? You're the richest guy in the world. Do you really need to also be an asshole? There was no reason he had to march people out of the office. So I saw that, and I kind of turned on him a little bit. I said, "I don't like this guy having this much power." Whether he's trying to control it or make it the main information source of the world, controlled by the richest person in the world, I'm not very happy about that. So I'm either gonna...

Sam Parr

do you think he's gonna pull it off

Paul English

He does stupid things, like the $8 verification. That was a joke. But if he assembles smart people around him, it looks like the smartest people all have left; they've all run for the hills. But he's going to hire some new people in. I'm sure there are some good people that are still there. I'm sure he'll do some interesting things with it. I'm really looking forward to all the Twitter replacements that are going to come out. It's hard to compete with an entrenched company that has hundreds of millions of users. Because even if your product is better, does Stephen King really want to tweet on sampower.com where there'll be 1,000 followers, as opposed to Twitter where he'll have 1,000,000 followers? But I don't know. I think he stirred stuff up, and I want to see the innovation that comes out.

Shaan Puri

that's cool yeah I I think that there's a I think if somebody's gonna do it they're gonna have to come up with a a social innovation not a it's not a techno it's not a technical innovation so I have this kind of long running theory about social networks which is that every so social network is a change in privacy policy not a change in technology so like for example you know facebook was this privacy policy change where it was like instead of myspace this is only people that go to your school and at the door we gate you with your your school email address there's a change in privacy policy that totally changed people's behavior because now you're more interested in everybody and you're more willing to share then as facebook became the norm then it became you know things like twitter which was like change your privacy policy I don't have to accept your friend request for you to see my content it's like you could just follow me unilaterally you could just describe you could decide to get my content that was totally different than facebook then snapchat comes out and it's like here's the privacy policy here all the shit self destructs in 24 hours so right like 10 seconds whatever so content is not permanent here and so people flock to that and so there's just this ongoing shift of like the the what is the like the social rule set that we're gonna follow on this thing and so what's interesting with twitter is if you're gonna compete with twitter now I think you gotta do one of 2 things you gotta do it like kind of like gab or truth social's trying to do but somebody could actually pull that off where they basically take a community of people that are pissed off about twitter and there's enough pissed off people to go into their own echo chamber I think that's possible and then the other one is I think if you created you have to turn the disadvantage into an advantage so instead of stephen king saying why do I wanna go tweet here when there's only I'm only gonna have a 1,000 followers over here you have to make it where it's now benefit like the perk is that there's only a 1,000 people there so it's like more like private or invite only style communities that you can join that have the same content format as twitter something something like that I think is more likely to work than what people are trying today which is just we're twitter not owned by elon musk or we're a decentralized twitter and it's like nobody cares yeah

Paul English

I think that decentralized is a joke. I believe that's technology looking for a solution. I think Truth Social was an epic failure. The things that I care about on Twitter right now are that I'm bothered by all the trolls and the cruelty. You know, I look at TikTok, and I don't really watch TV, but I use TikTok probably 20 minutes a day. I like how positive TikTok is, and I don't know what the Chinese are doing to filter out the trolls, but...

Sam Parr

It's also just that young people, like the average 18-year-old, are kinder than the 18-year-olds of the past. You know?

Shaan Puri

do you think that's true

Sam Parr

I 100% think it's true. I think that they don't make fun of each other in the same way that you and I used to make fun of our peers at 18.

Paul English

Twitter... I mean, TikTok is amazing. Someone will post a video of themselves and they'll say, "Oh, my girlfriend just broke up with me," and "I think I'm very unattractive," or something really revealing and awkward. The comments are just unbelievably supportive. Yeah, it's just amazing. It's so different than Twitter. What I want as a Twitter competitor is to create the kind of Twitter where there are no trolls and no cruelty. I also want to deal with misinformation. When you see a tweet that says, "The COVID vaccine causes autism," how do you smack that down? I'm very interested in those super obvious issues: getting rid of cruelty and flagging misinformation, but doing it without filtering out independent information. There are a lot of places in the world right now where it's scary to be publicly identified and to state your opinion. Maybe even in the U.S., if you have certain personal problems, like some people might not want to say they're bipolar because maybe that will hurt their career. But I think there is a way to build something like Twitter that is kind and truth-oriented. I haven't spent a lot of time in the last two weeks brainstorming with some other people, but I'm also thinking about doing something new. I'm confident that there will be something new, whether it's something that I help people with or something completely independent. I don't know, but someone needs to create something better.

Sam Parr

Paul, I'm going to ask you one last question before we have to move on to the next segment. What's your domain portfolio worth right now, you think?

Paul English

So, I have 300 domains. Let's say it costs me $10 each a year, so I'm spending $3,000 a year in domain fees. I paid $100 out of $1,000 to buy domains. I don't sell them that often because I still hold on to the idea that caused me to buy the domain. Most I hold on to. Occasionally, someone will motivate me, like a young entrepreneur who has an idea for a domain that I'm not doing anything with, and I'll sell it to them. I don't know, I have some that are worth $100,000 or more, and I have some that are just funny, probably just to me. So, I'm not sure if you have the price.

Sam Parr

on that lola would be mid 6 figures I would imagine right

Paul English

look we paid 500,000 to buy lola we were in a bidding war

Shaan Puri

it's it's up for sale again

Paul English

I would... it's up for sale. Yeah, because we sold the company to Capital One. They want everything to be Capital One; they didn't want the name "Lola." So, the name is for sale. Perfect! Buy it back, possibly.

Shaan Puri

Okay, amazing! Where should people go to find you? I'm on your website, and I think your website's pretty cool. You have sections like "Here's how I manage my time" and "Here's how I run meetings." I love when people do that—when they put their operating playbooks out there. Is that the best place to follow you, or should...?

Paul English

Twitter... yeah, I talk about meditation. I talk about getting rid of pain and suffering. I talk about getting rid of anger from your life. It's just my name: PaulEnglish.com.

Shaan Puri

awesome well paul thanks for coming on appreciate it

Sam Parr

Yeah, we appreciate you doing this. I'm on your bipolar social club. I don't think I have bipolar, but I still think it's fun to follow along with this site.

Paul English

so thank you awesome

Sam Parr

thank you and we appreciate you coming

Paul English

thanks a lot guys