Paul English, co-founder of Kayak (sold to Booking.com for $2 billion), walks through six successful company exits, his philosophy of team-first company building, and how he thinks about recruiting as the single most important founder skill. Sam and Shaan dig into his famous investor misses (Airbnb, YouTube, Snapchat, Dropbox), his new venture studio, and his takes on Elon Musk’s Twitter acquisition.
Speakers: Paul English (guest, serial entrepreneur, co-founder of Kayak), Sam Parr (host, co-founder of The Hustle), Shaan Puri (host, founder of Milk Road)
Introduction and How Paul Met Dharmesh [00:00:00]
Sam: All right, Paul, what’s going on, man? Dharmesh — CTO and co-founder of HubSpot — told us we have to, well, we don’t have to, but we should talk to you. Why did he say that?
Paul: I don’t know, it’s going to be connected. Dharmesh and I have a lot of fun talking together about technology, philosophy, and teams. One fun thing Dharmesh and I did — going back many years now, when I was CTO and co-founder of Kayak — Dharmesh and I kind of switched jobs for a day. I got him an email address: dumbass@kayak.com, made up business cards, and he basically sat at my desk at Kayak for a day. Then I sat at HubSpot for a day. That was the beginning of our friendship, realizing that we each had things we could learn from each other. He’s been a great mentor and friend.
Sam: Your big hit so far has been Kayak, right? What did you sell that for — like two or three billion?
Paul: Two billion. I’ve actually sold six companies in a row, including Lola. I’ve sold another one after Lola — Moonbeam, which is a podcast app — and now I’m on to my seventh company.
Sam: Which of the six has been the most financially successful for you?
Paul: Kayak was the biggest financial outcome. I’m deeply appreciative of that, and I learned a lot. I met some amazing people. But there are other things which are also really significant that aren’t just monetary.
My first sale — I should say I’ve sold six in a row. There’s another one I don’t really count because it was a company I created in high school, but it’s very meaningful to me: making money in high school designing software.
The Six Companies — A Brief History [00:02:30]
Sam: What were the six?
Paul: I had a company called Boston Light. We were an e-commerce company — we let people set up storefronts, a little bit like Shopify, but this was 20 years ago. We sold that to Intuit, and I became VP of Technology there. Then I had a company called Intermute, which was internet security software. I did that with my brother Ed English. We sold that to Trend Micro. I did gethuman.com, which served customer service information to over 200 million people. Then Kayak. Then Moonbeam, the podcast player. Then Lola, which was business travel and expense. I think that’s the list.
Sam: What’s your thought process for coming up with these ideas? Were you scratching your own itch, or analyzing trends?
Paul: It’s mostly scratching my own itch. The only one that wasn’t my original idea was Kayak. My co-founder Steve Hafner is one of the founders of Orbitz, and he had observed that 70% of people who searched on Orbitz — when they were done — opened a second browser and went directly to united.com to buy the ticket. Orbitz did all the searching for people but never made money on it. Steve said, “Why don’t we create a company where all we do is search, and then if someone wants to go to United, they click the link and we send them directly to United to buy the fare?”
We met by chance and within about 45 minutes decided to sign up as co-founders. We each put a million dollars into the original round of financing. I quickly owned it from a product standpoint. I spent about an hour on Expedia that night — they were the market leader at that point — and came back the next morning saying, “This isn’t going to be hard.” Expedia’s UI was seizure-inducing. There was so much stuff going on the screen.
Sam: You put a million dollars in — was that all your chips on the table? Was that half your net worth? Did that add anxiety to the process?
Paul: I had just sold a company for $30 million, so that million wasn’t that hard for me at that point. My prior company — the one I blew through my 401k to finance — that was financially tough to get going. But for Kayak I’d made some money, so I could afford to help finance it.
Why He Keeps Selling [00:05:30]
Sam: Why do you sell your companies? Why not try to run them long-term, or have them exist under a management team you control — like Dharmesh? He’s been doing HubSpot for forever.
Paul: Kayak I did for 10 years. That was my longest stint. We ended up taking it public in 2012, which was incredibly fun, and then we sold it shortly thereafter to Booking.com, which is the parent company. I was just frankly bored. I felt like I was editing the flight search screen for 10 years and I wanted to try something new.
I had an unbelievably strong tech leadership team at Kayak. At that point I felt like I could sneak out without hurting the company because I had people who wanted to do UI, product, architecture. It gave me the freedom to try something new.
Internet OGs and Famous Misses [00:07:00]
Sam: You’re kind of an internet OG. Kayak was a pretty huge thing — still is a huge thing — but in terms of internet exits, it was early in the game. Who are some of the big shots and ballers now that you got to know earlier on?
Paul: So when we financed Kayak — it was created in 2004 — we really launched out of General Catalyst in Cambridge, Massachusetts, and then raised money from Mike Moritz. I remember one day my co-founder and I were working out of the office and Mike Moritz said, “I want you to meet a couple guys.” It was Chad Hurley and his co-founder — the founders of YouTube. I remember meeting those guys at the Sequoia office. Mike said, “Yeah, these guys are putting videos online.” I was like, “Yeah, that’s cool, whatever.” I didn’t see that one either.
I’ve been pretty good as an investor — I think my IRR is 30.5% over the last several years. 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 million valuation — that would have been a big outcome. I met Drew at Dropbox early on. That wasn’t under the guise of investing — it was really just networking. But I thought Dropbox was going to be plagued by security issues. I’m still kind of shocked. Do you know that Dropbox doesn’t really encrypt your files? A malicious Dropbox engineer could toast your files. It’s amazing they’re as big as they are.
Sam: Yeah. You met Brian Chesky at Airbnb too?
Paul: I met Brian Chesky at Airbnb when they were financing at a billion-dollar valuation. I think they’re now worth $100 billion or something. I remember loving Brian — I thought he was iconic, passion-driven, mission-driven. But I didn’t see how big everybody was going to get. I said, “This seems awesome for people who want strangers living in their house, but how many people is that going to be?” So I kind of missed the bigger picture there.
Sam: What was he like when you met him?
Paul: He was very serious and intense, but charismatic. He listened well. We had a good conversation where he wanted me to give him feedback on the company — Kayak was much bigger at that point. I saw him as very serious, intense, and charismatic.
Sam: Yeah. Whenever you’ve been doing technology for 15 or 20 years you get this crazy story arc where you see people and think, “I think this person’s amazing, they might go on to do amazing things.”
Angel Investing Hits [00:10:30]
Sam: What have been some of the hits?
Paul: One of the ones coming up right now is Pilot.com. I met those guys when I was a judge at the MIT $100K competition. They had a company called Ksplice — really exotic technology, they could patch a Linux operating system as it was running so you don’t have to reboot your servers. They sold that to Oracle. Then they created Zulip, which they ended up selling to Dropbox. When they left Dropbox and created another company, I basically asked if I could invest before I knew what they were working on. I wrote them a check before I knew what they were doing. That’s a 40x. I think I wrote a check at a $30 million valuation and their last valuation was around $1.2 billion.
The founding team had the mojo. When I met them I just knew those guys were going to create something serious. They were intense, high energy, they laughed a lot, they finished each other’s sentences. They really enjoyed working together.
Another good return — about 22x — was Kensho, which is a competitor to the Bloomberg terminal. I invested in them because their founder Pete Kraskow used to work at Kayak and I just knew he was destined to do great things.
Shaan: We actually had a guy named Trung work for us. Trung was an analyst at Kensho, and Kensho from the outside fits this stereotype of an uptight financial firm. We found Trung working there — this guy who is a loudmouth, literally speaks so loud, full of energy, and was a great writer. We encouraged him to use Twitter and now he’s got a million followers. We recruited him from Kensho.
Paul: That’s amazing. I like Kensho because of that.
Moonbeam, New Ventures, and Building the Next Thing [00:13:00]
Sam: Kayak was a big win. Then you did things like Moonbeam — podcast discovery. Podcasting has kind of been like, it looks niche, and most podcast products that win are good lifestyle businesses. There haven’t been that many big winners in the podcasting space in terms of tools.
I’ve talked to people who have exits like $700 million or $800 million or a billion dollars, and that becomes the new table stakes for the next thing they do. Some go that route — “I’ve got to get huge now.” Others say, “No, I’m literally just going to program things in my house for fun.” Which way do you think about it?
Paul: I’ve always said for each of my companies it’s team first, customer second, profit third. I set that up for Kayak on day one. We put together our culture plan, and I really think it’s a good way to execute. If you focus on becoming a phenomenal recruiter — really become a student of recruiting, read all the books, listen to the podcasts, learn from others — and recruit an amazing team, and then figure out how to lead that team so 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 magic. Magic teams create magical products, and then usually if you can create a magical product you can find a profitable business.
For me now, after I sold Lola — my business travel and expense company — to Capital One about a year ago, I opened up a venture studio called Boston Bounder Studio. It’s at bbs.net. We have nine apps under development. Some are itch-to-scratch fun little things we put out with source code. Others are swings for the fences where 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 billion-dollar company.
The Deets Idea: Fixing Online Reviews [00:15:30]
Paul: Online reviews are broken. If you go to Google right now and search in quotes “buy Amazon reviews,” you’ll see 37,000 pages that tell you how to do that. If you make headphones and want to sell on Amazon, you can easily buy a thousand five-star reviews. These fake review companies are run by PhD computer scientists who are evading Amazon’s bot detection. They go through proxy servers, they have aged accounts, they buy products.
And if you go to Yelp or TripAdvisor, the reviews are largely by people you don’t relate to. I looked up a sushi restaurant in New York and saw five-star reviews where people talked about how great it was because it’s really cheap. If you like sushi, ten dollars a person for sushi in New York is a little scary.
Or on TripAdvisor you’ll see five-star reviews for Motel 6. That was great when I was 20 years old, but a lot of people just don’t relate to whoever’s doing the reviewing.
The idea of Deets is to blow that up and say: it’s just the recommendations from your friends and the influencers you choose to follow, and then using machine learning and look-alike modeling to find people who are similar to you.
Sam: It seems like you pick really hard industries. Travel is notoriously difficult — incredibly competitive, small margins. Podcasting — nothing has entirely clicked to make it a fantastic industry. And reviews — Yelp hasn’t innovated in five or ten years, their stock is bad, and Google reviews is a horrible person to compete with because they already have everyone. What’s the game plan? Why do you keep picking the hardest things?
Paul: The origin of Deets is that I’m friends with some people who own restaurants in Boston. I saw the difficulty they had during COVID, and I developed a lot of compassion for restaurant owners. They all told me how much they hate Yelp. Yelp is like the mafia — if you pay them hundreds of dollars a month, they’ll “sort of clean up your site.” There’s actually a movie called Billion Dollar Bully about Yelp that came out in 2019. The opening scene is an Italian chef who said when he opened his first restaurant in Italy, someone kept breaking his windows. He’d fix them, they’d break them again. Finally a guy comes in and says, “I notice someone keeps breaking your windows. If you pay me a hundred dollars a week, I’ll make sure no one breaks them anymore.” He knew that was the guy breaking the windows. He said, “That’s Yelp.”
I look at Yelp as a 20-year-old dinosaur. The last 20 years were theirs — the next 20 years we want.
The world is different now. For one, the rise of influencers, particularly Gen Z — they make all their purchase decisions based on influencers. We want to make it really easy, rather than scrolling through Instagram trying to find an old post about a restaurant you saw a month ago, to have it all in one tight, clean UI. Your friends, your influencers.
And I’m really inspired by TikTok. TikTok is 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 watching them — there’s a lot of dogs, gardening. TikTok has figured out what I’m interested in without ever asking me a question. They don’t even ask you who your friends are. They’ll find some DJ in Berlin who has the same weird sense of humor as you and show you her videos. I really like that look-alike modeling. We’re doing that with Deets too.
Is Building Easier When You’re Wealthy? [00:22:00]
Sam: Do you think starting a company now that you’re wealthy is easier or harder than when you were just getting going?
Paul: 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 401k to finance it.
To me, working hard is: recruit hard, lead, coach people, get people excited. I’m working on that as hard as I ever have. There is some advantage to having money — if you see a stupid problem that costs five grand to fix, when you’re creating your first company you don’t have that five grand. Now you do. You just pay a little money and problems go away.
Shaan: Yeah, I think it’s different, and you have to work with the pros and the cons. Recruiting is easier and you waste less time on the rookie mistakes. But there is some diminishment maybe of the edge. The things that made you successful the first time might have been a technology wave, a bunch of opportunity. You have to recognize new technology waves and new inflection points. He’s talking about machine learning getting a lot better — now we can do things that make the user experience completely different. Before you had to ask someone 50 questions to show them something good. Now they swipe three times and you start getting something good. A delightful user experience that was impossible before.
Paul: I want to tell you one thing about doing tech now versus 20 years ago. 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, AWS, the tools, the open source — it’s pretty easy to assemble the right libraries and right people to put something together.
Companies fail today for two reasons. Either there’s a founder implosion: they create a toxic culture, people hate their boss, hate working there, and they all leave. That happens all too often — they fail the culture code. Or number two: they built a nice product, but it solves a real problem that no one cares about. Unfortunately a lot of founders have an itch to scratch and they get really obsessed — “I have this little problem, I’m going to work on it for ten years” — and they don’t realize that not a lot of people have that same problem. It makes me sad when I see a beautiful product that solves a problem I don’t care about.
Sam: That’s the number one cause of death with startups.
Recruiting as a Craft [00:26:00]
Sam: You said a second ago to become amazing at recruiting — read all the books, listen to all the podcasts, become a student of it. For somebody who’s talented but hasn’t put their focus on becoming great at recruiting, what are the 80/20 principles? And are there any that are counterintuitive?
Shaan: I’m pretty good at it, but I don’t know. It’s like a belt system — even if I’m a blue belt there’s still a black belt I could learn from.
Paul: The main thing is just recruit all the time. Always be recruiting. Always be trying to connect with people. You might go to a coffee social to learn about why crypto is terrible or whatever, and you don’t realize someone there could be your next unbelievable CMO. You’re not expecting to meet them, but if you always have your spidey sense out for amazing people, and 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 about my recruiting style…
Sam: That’s the best way to start a story.
Paul: So someone asked me about why I’m so laser-focused on getting certain people. When I was in seventh grade at Boston Latin School, I was at my locker and a really cute girl walked by. My friend noticed me turn my head and look at her, and said, “English, don’t even think about it — she’s dating the captain of the football team.” At that moment that girl went into 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.
It’s the same with recruiting. When I see someone amazing, I always ask them, “Do you know anyone even more amazing than you?” And that leads to a kind of hilarious succession of conversations. I do whatever it takes to get them excited and come meet my team.
I’ve always said: the first five people you hire will hire the next 50, who will hire 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 people, they’ll say, “Oh my God, I need to work with this team.”
Paul’s Personal Life and the Bipolar Social Club [00:31:30]
Sam: You and Dharmesh are interesting to me because you both have this dry, almost nerdy sense of humor. If you go to paulenglish.com it talks about your investments, your founder stories, and the clubs you’re involved in — one of which is the Bipolar Social Club. Your Wikipedia mentions you had some experiences with bipolar disorder. The fact that you’re part of the Bipolar Social Club is funny in this great way.
Paul: I have bipolar illness. I was diagnosed at age 25, and it’s a pretty serious illness. A lot of people end up killing themselves, ruining their marriage, their job, their lives, and it took me a good 10 to 15 years to learn how to manage it. I have bipolar 2, not the most severe type. Bipolar 1 can involve voices, people end up homeless, or worse. Bipolar 2 still has its problems, but over the years I learned how to deal with it.
I want to be able to laugh with other bipolar people about the funny things about being bipolar. So I created this video series — if you go to bipolarosocialclub.org, there are 10 people with bipolar illness who kind of tell their journey. It’s destigmatizing it: “Yeah, it’s a mental illness, there are some shitty things about it, but there are some funny things about it too.”
I also 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. My gay friends say they have gaydar. I can tell bipolar people across the room.
Sam: You’re constantly tinkering on stuff. Dharmesh has got Venn Diagram.com — a community for people who love Venn diagrams — and a Wordle game that makes like a hundred grand a month. You seem like the same type.
Paul: 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 brand and names. Dharmesh and I share that — we’re both prepared to spend big money to buy a good name.
I do a lecture on where creativity comes from. I’ve taught everywhere from Berklee College of Music to Dartmouth film school to Rhode Island School of Design. What I do is: let’s say I’m teaching Thursday at 5. On Wednesday at 5 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 — take a picture of something that annoys you.” Then I teach the students how irritation becomes inspiration, and how any problem can become the motivation for a product.
How the MFM Brainstorm Format Was Born [00:35:30]
Shaan: When we started this podcast it was doing all right — maybe 10,000 people listening to every episode, 100,000 a month. It was a classic interview show. Getting to know guests: “Oh, you built Kayak, amazing, tell me about it.” Just like every other tech or business podcast.
Then one day I invited Sam on. I was like, “Let’s just shoot the shit the way we do when we’re not on a podcast — have you seen this? Why doesn’t somebody solve this? I tried to book this the other day, it was so annoying.” We just started brainstorming. We called that one “The Million Dollar Brainstorm” — ideas we don’t have time to do, but that we thought could be million- or billion-dollar ideas. After that the whole podcast took off into the top ranks of the charts. I think it’s because we switched into this ideating, brainstorm mode. There are a lot of people like us out there. Dharmesh is trying to find all the Venn diagrammers — we’re trying to find all the people who love to shoot the shit and brainstorm ideas. Sounds like you’re one of them.
Can you give us a couple of ideas? Maybe pull three names from your domain portfolio and give us the one-line pitch for some ideas you’ll probably never have time to do?
Ideas from Paul’s Domain Portfolio [00:37:00]
Paul: Sure. I’ll tell you some ones where the itch was enough that I actually did a little bit of work.
One: I live in Boston but spend a lot of time in New York. Where I stay is kind of between the West Village and Tribeca. I don’t really know the city well — if I’m trying to meet someone on the Upper West Side, I don’t know what’s up there. I wanted a website where they can see where they are, where I am, and pick a bar in the middle. So I built an app called middle.net. It grabs your location from the browser and shows you a coffee shop or bar to meet in the middle. I’ll never make money doing that, but I needed it.
Sam: I’ll use it. I need that all the time.
Paul: Another one: when you meet someone at a conference and want to swap contact info, it’s annoying to type in phone numbers, email addresses. The .card thing is fine but you’ve got to carry a card around. So I designed a little app called FunContact — funcontact.com. It gives you a set of QR codes. One might be just my email, another might be my email plus home address. Based on who I’m meeting and what information I want to share, I swipe through and show them the right QR code, they scan it, and they’ve got my contact info.
I actually used it last night. It was my three-year anniversary with my girlfriend Rachel. We went to San Ambroeus in the West Village — same restaurant as our first date three years ago. Next to us was Anna Wintour and Bradley Cooper. On our first date three years ago, the same thing happened. Then at the end, the table on the other side was four people working in the fashion industry where my girlfriend works. We bonded, talked about the Bipolar Social Club clothing brand I want to create, they asked for my number, and I just pulled out FunContact and scanned it. Now all these young fashion people have my number and we’ve been messaging today about Bipolar Social Club.
Sam: What’s the clothing brand?
Paul: Bipolar Social Club. The idea is: bipolar people wear the brand, they’re proud of it. It’s a fun name. “Bipolar and proud.”
Problems in the Travel Industry [00:42:00]
Sam: Is there anything in the travel industry — you had more data than almost anyone — where you saw problems that still aren’t being solved?
Paul: The thing I had the most trouble with was flights and airports. TSA is a joke. The stuff they do gives you a false sense of security but there’s no real security there. That’s irritating.
Airlines are running on old technology. They have to be very conservative because if they adopt something too new and make a mistake, the plane can crash. So it’s very archaic.
I travel between Boston and New York. I never fly — by the time you go through TSA, get an Uber on each end, it’s often faster to drive.
I would like to see someone figure out how to work with all the unions, work with the airlines, work with TSA, and make flying pleasurable. It’s not pleasurable now. I remember growing up, people used to dress up to get on a plane. They were really excited to travel. Now airports are just a nightmare.
Sam: Yeah. Sounds like the hardest thing on earth to do, though.
Paul’s Take on Elon Musk and Twitter [00:44:30]
Sam: What do you think about what Elon’s doing? He buys Twitter, takes a technology-first approach, tries to change the culture overnight, forces people back in the office, lays off a bunch of people, ships changes really fast. Seems a little Helter Skelter. What’s your opinion as a CTO and someone who’s done tech for a long time?
Paul: I’ve followed it quite closely. Put me in the list of a thousand people who want to create a Twitter competitor right now. I’ve been spending a bunch of time the last week thinking about that.
I always knew Elon Musk was eccentric and I forgave him for some of his stupid stuff because he created such good products. I love my Tesla cars, I’m a happy Tesla stockholder from 2016. But when I looked at the way he fired people at Twitter — it was just obnoxious. You’re the richest guy in the world — do you really need to also be an asshole? There was no reason you had to march people out of the office. When I saw that I turned on him a little bit. I don’t like this guy having this much power. He’s trying to make Twitter the main information source of the world, controlled by the richest person in the world. I’m not very happy about that.
Sam: Do you think he’s going to pull it off?
Paul: He does stupid things — the eight-dollar verification was a joke. But if he assembles smart people around him… it looks like the smartest people have already run for the hills. I’m sure there are some good people still there, and he’ll do some interesting things with it. But 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 with hundreds of millions of users. Even if the product is better, does Stephen King really want to tweet somewhere with a thousand followers instead of Twitter where he has a million? But I think Elon stirred stuff up and I want to see the innovation that comes from it.
Sam: I have this long-running theory about social networks: every social network is a change in privacy policy, not a change in technology. Facebook was this privacy policy change where — instead of MySpace — it was only people who go to your school, gated by school email address. That totally changed behavior. Then Twitter was: “I don’t have to accept your friend request for you to see my content. You can just follow me unilaterally.” That was completely different from Facebook. Then Snapchat: “All this stuff self-destructs in 10 seconds. Content is not permanent.” People responded to that.
So there’s this ongoing shift in the social rule set. If you’re going to compete with Twitter now, I think you have to do one of two things. You could do what Gab or Truth Social is trying to do — take a community of people pissed off about Twitter and create their own echo chamber. There are enough pissed off people to make that work. The other option is: turn the disadvantage into an advantage. Instead of Stephen King saying “why do I want to go here when I’ll only have a thousand followers,” you make it so having a thousand people is actually the perk. More like private or invite-only style communities that have the same content format as Twitter. Something like that is more likely to work than “we’re Twitter but not owned by Elon Musk” or “we’re a decentralized Twitter.” Nobody cares.
Paul: I agree. Decentralized is technology looking for a solution.
The things I care about on Twitter right now — I’m bothered by all the trolls and the cruelty. I look at TikTok and I don’t watch TV really, but I use TikTok probably 20 minutes a day. I like how positive TikTok is. I don’t know what the algorithm is doing to filter out the trolls, but the average 18-year-old on TikTok is kinder than the 18-year-old was when you and I were growing up.
Sam: I 100% think that’s true.
Paul: Someone will post a video and say, “My girlfriend just broke up with me and I think I’m very unattractive” — really revealing and awkward — and the comments are just unbelievably supportive. So different from Twitter.
So I think a Twitter competitor would be: create the kind Twitter, with no trolls and no cruelty. And also deal with misinformation — when you see a tweet that says “the COVID vaccine causes autism,” how do you flag that without filtering out independent voices? There are places in the world where it’s scary to be publicly identified and state your opinion. Maybe even the US in some cases.
I think there is a way to build something like Twitter that is kind and truth-oriented. I’ve been spending time with people who are also thinking about doing something new. I’m confident that someone will build something better — whether that’s something I help with or something completely independent.
Domain Portfolio Value and Where to Find Paul [00:53:00]
Sam: One last question. What’s your domain portfolio worth right now?
Paul: I have about 300 domains. Let’s say it costs me ten dollars each a year — so I’m spending about three thousand dollars a year in domain fees. I paid hundreds of thousands of dollars total to buy domains over the years. I don’t sell them often because I still hold onto the idea that caused me to buy the domain. Occasionally a young entrepreneur will have an idea for a domain I’m not doing anything with and I’ll sell it to them.
Some of them are worth a hundred thousand dollars or more. Some are just funny, probably just to me.
Sam: Lola would be mid-six figures, right?
Paul: We paid $500,000 to buy Lola. We were in a bidding war. And it’s up for sale again — because when 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.
Sam: Possible buyback opportunity. Amazing. Where should people go to find you?
Paul: paulenglish.com. I talk about meditation, getting rid of pain and suffering, getting rid of anger from your life. It’s just at my name.
Sam: Your website is pretty cool — you’ve got “here’s how I manage my time, here’s how I run meetings.” I love when people put their operating playbooks out there.
Paul, thanks for coming on, we appreciate it.
Paul: Awesome. Thank you.
Shaan: We appreciate you doing this. And I’m on your Bipolar Social Club — I don’t think I have bipolar, but I still think it’s fun to follow along.
Paul: Awesome. Thanks a lot, guys.