Paul English: How He Built And Sold 6 Companies And Why He Believes Irritation Becomes Inspiration
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 to finance it.
All right, Paul, what's going on, man? Will you, uh, Dharmesh, uh, CTO, co-founder, HubSpot. Told us we have to, we have to, we don't, we don't have to, but we should talk to you. What, uh, why did he say that?
I don't know. It's gonna be connected. Um, Dharmesh and I have a lot of, uh, fun talking together about technology, philosophy, and teams. Um, one fun thing that Dharmesh and I did going back many years ago now when I was CTO, co-founder of Kayak, Dharmesh and I kind of switched jobs for a day. So I actually had him made up, I got him an email address, dharmesh@kayak.com, and made up business cards. And he basically sat at my desk at Kayak for a day and then I sat at HubSpot for a day. And that was sort of the beginning of our friendship, realizing that we each had some overlap, but some things we can learn from each other. And he's been a great mentor to me and friend.
And your big hit has been, well, so far you have a new company, Lolo, which I don't know if you know this or not, you guys advertise with my old company, The Hustle, a bit. So yeah, uh, we worked with you a bit, but, um, your big hit so far has been Kayak, right? What did you sell that for, like $2 or $3 billion?
Which one of the— so which of the 6 has been the most financially successful for you?
Kayak was the biggest financial outcome which I'm deeply appreciative of. And I learned a lot at Koch, met some amazing people. But there's other things which are also really significant that aren't just monetary. So my first sale, I don't have to, I just told you I sold 6 in a row. There's another one that I don't really count 'cause it only was a company I created in high school, but it's very meaningful to me making money in high school, designing software.
And what were the 6?
So 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 goes back 20 years ago. We sold that to Intuit. I became VP technology for Intuit. Then I had a company called Intermute, which is internet security software. I did that with my brother Ed English. We sold that to Trend Micro. I did a company, gethuman.com, which is serve customer service information to over 200 million people. Kayak. Moonbeam, the podcast player, Lola, which is the business travel and expense. And did I forget one? I think that's the list.
And so what's the like, um, thought process? So did you start them all in kind of the same way where you were maybe scratching your own itch or you're like analyzing trends? So like what's your process to come up with these ideas?
It's mostly scratching my own itch. I mean, I can go through company by company. The only one that wasn't my original idea was Kariak. My co-founder Steve Hafner was one of the founders of Orbitz, and he had observed at Orbitz that 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, wherever to buy the ticket. And so Orbitz did all the searching for people but never made money. And so Steve basically 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'll send 'em directly to United and they could buy a fare. And that was his observation. We met by chance and within probably 45 minutes decided to sign up as co-founders. Each put $1 million into the original round of financing, and then I very quickly owned it from a product standpoint. I went— I remember I spent an hour on Expedia that night because Expedia was the market leader at that point. And just going back the next morning saying, this isn't going to be hard. So I looked at Expedia as bloatware. It was sort of seizure-inducing. There was so much stuff going on the screen.
You put $1 million in, was that like a, I'm going all my chips on the table right now? Or was that half your net worth? Was that a small bet for you?
No.
How did you feel at that time? Did that add some anxieties to the process?
I just sold a company for $30 million, so I could have— the million wasn't that hard for me at that point. My prior company that I sold for $30, I blew through my 401 to finance it. So my first company, was tough financially to get it going. But for Kayak, I had made some money so I could afford to help finance it.
Why did you— why do you sell your companies? Why not, you know, try to run them or have them exist under a management team that you control for a long time?
Yeah. So Kayak I did for 10 years. That was my longest stint. And we ended up taking it public 2012, which is incredibly fun. And then we sold it shortly thereafter to Priceline, or really Booking.com, which is the parent company. And I just frankly was bored. I felt like I was editing the flight screen for 10 years and I wanted to try something new. And I'd had an unbelievably strong team at tech leadership at Kayak. So at that point I felt like I could sneak out without hurting the company because I had people at that point that could do UI, they could do product, they could do architecture. So it gave me the freedom to try something new.
You, you're kind of, I mean, you're, you're kind of like an internet OG a little bit. I mean, Kayak's one of the, was like a pretty huge thing. It still is a huge thing, but in terms of like internet exits, it was, it was, it was early on in the game and 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?
Um, you mean across the industry overall?
Yeah, because like Dharmesh has all these crazy stories where he's like, you know, I was an early investor in Coinbase and I, and I met the team and I thought, well, he didn't actually tell me this. I'm just making, I mean, he did invest in Coinbase, but I'm sure there's like a story. He was like, well, I met this guy Brian and he was like living out of a closet and doing all this weird stuff. And he was a quirky guy. And I mean, he just has met, or I believe he was an early investor in Dropbox as well. And like, he probably has all these interesting stories. About some of these folks who are now like tycoons or 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 he got insight into these businesses. Do you have anything like that?
Yeah. So I met Brian Chesky at Airbnb when they were financing a billion-dollar valuation, and I think they're now worth $100 billion or something like that. And I remember at the time, like loving Brian, thought he was iconic and passion-driven, mission-driven. But I didn't see it, how big Airbnb was going to get. I said, this seems awesome for people who want to have strangers living in the house, but how many people is that going to be? So I kind of missed the bigger picture there.
What was he like when you met him? Just like he was very— 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?
I saw him as very serious and intense. He was charismatic. He listened well. So we had a good conversation where he wanted me to give him feedback on the company because Kayak was a much bigger company at that point. And yeah, I just took him as very serious, intense, and charismatic.
Yeah. Whenever you're like, you're doing technology for like 15, 20 years, you just get this like crazy story arc or like, you know, um, you get to see people and you get, you see all these people that you're like, all right, I think this person's 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 of, uh, that you've seen? Cause you've been kind of in the game for such a long time.
Yeah. So when we financed, we, KAC was created in 2004. Uh, we really launched out of General Catalyst in Cambridge, Mass. And then we raised money from Mike Moritz at Sequoia. I remember one day my co-founder and I were working out of the Square office and Mike Moritz said, oh, I want to introduce you to a couple guys. This is Chad Hurley and I forget his co-founder, but they were the founders of YouTube.
Steve Chen, I think.
Yeah, that's right. And I remember meeting those guys at Square office and Mike's like, yeah, these guys are like putting videos online. I'm like, yeah, that's cool, whatever. I didn't see that one either. I have, 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'm doing 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 million valuation. That would've 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. I'm still kind of shocked. I use Dropbox. Do you know that they don't really encrypt your files and that a Dropbox engineer, if they were malicious, they could 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?
Say anything.
Yeah. What have been the— you said you've invested in 60 companies and you got this great IR. What have been some of your hits so far?
One of the ones going on right now is pilot.com. I use it. And yeah, that's an amazing company. I met those guys when they were— I was a judge at the MIT $100K competition and 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. I was part of, you know, I was the judge at that and I helped them win that competition. And then I invested in their next company, Zula, which they ended up selling to Dropbox. And then when they left Dropbox, created 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 40xer. I think I financed some— I wrote a check as part of their round at $30 million valuation. And I think their last valuation was like $1.2 billion or something. But that's one that the founding team had the mojo. So when you met them, you 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 just really enjoyed working together. I also— another good return for me at 22x was Kensho, which is a competitor to a Bloomberg terminal. And I invested in them because their CTO, Pete Krusko, Used to work at Kayak and I knew him from Kayak and I just knew he was destined to do great things. And he, that was a really nice exit.
We, we had this guy Trung work for us. So Trung was an analyst at Kensho and Kensho is like this, I, you know, they're a startup still, but like, uh, the stereotype is to me from an outsider, they've kind of fit this like stereotype of like an uptight financial firm and we found Trung working there. And this guy Trung who works for us, he's like the— he's got— he's a loudmouth, like literally, like he speaks so loud and he's full of energy. And he was a writer for us and we taught him how to, you know, we like encouraged him to use Twitter. Now he's got like, you know, a million followers on Twitter and we recruited him from Kensho.
That's amazing.
I like Kensho because of that.
Thank you. Um, and you— so Kayak was a big win. Um, and then you did things like, let's say Moonbeam, which is like, you know, a podcast discovery type of app could have been big, but you know, maybe I think anything in podcasting is, is sort of like looks sort of niche and most of the podcast products, even that win are sort of like, you know, really good lifestyle businesses. So far there hasn't been that many big winners in the podcasting space in terms of tools. Um, are you, do you, I know one thing that's hard. I've talked to people who, who kind of have an exit like $700 million or $800 million or a billion dollars. It's like, that becomes the new table stakes for the next thing they do. Some go that way and they say, okay, I gotta get huge now. And others are like, no, I'm literally just gonna program things in my house for fun now. Like now I, I, I don't want to go try to catch lightning in a bottle again. Which way, uh, do you think about it? Or is there another, a third way?
I've always said for each of my companies, it's team first, customer second, profit third. I said it for Kayak on day one. We put together our culture plan. And I really think it's a good way to execute because if you fo— if you focus on becoming a phenomenal recruiter and really becoming a student of recruiting, like read all the books, listen to the podcasts, learn from others that talk about recruiting and recruit an amazing team and 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 magical teams create magical products. And then usually if you can create a magical product, you can find a profitable business there. So for me now, after I sold, um, Lola, my business travel and expense company, I sold that to Capital One a year ago. I then opened up a venture studio called Boston Venture Studio. It's bvs.net, and we have 9 apps under development. Some of them are an itch to scratch, like fun little things that we put out with source code. Others are a swing for the fences, really think it can become big. There's a company I launched 2 weeks ago called Deets, like show me the deets. That could be a billion-dollar company. What we're doing is we're 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 this 37,000 pages that tell you how to do that. If you make, you know, these headphones I'm wearing, if you make a competitor of these and you want to sell it on Amazon, You can easily buy 1,000 5-star reviews for that if you want. And these fake review companies are run by PhD computer scientists. They're evading Amazon's bot detection. So it's very difficult at this point to detect them. They're going through proxy servers, they have aged accounts, they buy products. And then if you go to Yelp or TripAdvisor, their reviews are largely by people you don't care about. You know, like I looked up a sushi restaurant in New York and I saw 5-star reviews of this place. People talked about how great it was because it was really cheap. And I don't know about you, if you like sushi or not, but I'm not sure I'm going to be that excited having $10 a person for sushi in New York. That's a little scary to me.
I always— Yeah. You want that catfish and cream cheese roll.
Yeah. If you go on TripAdvisor and you look for hotel, you'll see a lot of 5-star hotel, 5-star reviews from Motel 6. And that was great when I was 20 years old, I'm not sure I would stay at a Motel 6 now, but a lot of views just don't relate to the person doing the purchase. So the idea of Deets is we're going to blow that up and say it's just the recommendations from your friends, from influencers that you choose to follow, and then using machine learning, doing lookalike modeling to find people that are similar to you.
Man, it seems like you pick really hard industries. Travel is like, again, I'm an outsider, you're the expert, but it seems notoriously difficult. It just seems incredibly hard. Incredibly competitive and very, very, very challenging. And the margins seem small and very hard, it seems, to start one of those things now. Uh, podcasting, terribly hard. I don't, you know, I don't entirely understand why it's so hard, but like the— nothing has entirely clicked to make it this, this fantastic industry, uh, even though a lot of people use podcasts. And then reviews also seem terribly challenging. You know, Yelp has had like Yelp hasn't innovated in, in, in 5 or 10 years. Their stock sucks. Uh, Google Reviews is, is a, is a horribly challenging person to compete with because, you know, they have all these people already using it. What, what's the game? What's the game plan here? And why are you picking the hardest things to work on?
Um, yeah, the origin of 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 hate Yelp. Yelp is just like mafia where you pay— if you— they call you and they say, have a lot of bad reviews, call us and pay us hundreds of dollars a month and we'll sort of clean up your site on Yelp. It's kind of like in Italy, there's a movie called Billion Dollar 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 again the next week. He fixed them the next week. Some guy comes in and says, I notice someone keeps breaking your windows. If you pay me $100 a week, I'll make sure no one breaks your windows anymore. And he knew that was the guy who was breaking his 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 want to be the next 20 years. And I look at the evolution, you know, the world is different now than it was when Yelp was created. For one, the rise of the influencers, particularly Gen Z, they make all their purchase decisions based on influencers. And that's true now 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 a question. And the way they work is they don't even ask you who your friends are. They will find some 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. We're going to find your friends, the influencers you like, and then people of the same taste as you. This data is wrong every freaking time.
Whoa, 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 think that starting a company now that you're wealthy is easier or harder than when you were just getting going in your career?
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. To finance it. Um, to me, work hard is recruit hard, lead, coach people, get people excited. And 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 having money that if you see a stupid problem that costs 5 grand to fix, you know, when you're creating your first company, you don't have that 5 grand. Now you do. So you just pay a little money and problems go away.
What do you think, Sean?
Easier or harder?
Uh, yeah, I think it's different and you just have to like work with this, the pros and the cons, right? Like, yeah, recruiting is easier and you waste less time on the, on just like the rookie mistakes that you always make. But then, you know, there is some diminishment maybe of the edge or, um, you know, the things that made you successful the first time might have been that there was a technology wave going on. There was a bunch of opportunity and like, You have to recognize new technology waves or new inflection points, new things that have changed. Like, you know, he's talking about like basically machine learning has gotten a lot better and now we can do things that like make it, make the user experience way different. If before we had to ask you 50 questions to show you something good, and now you can swipe 3 times, 4 times, and I could start getting you something good. Um, you know, I can create a delightful user experience, whereas before, you know, maybe I couldn't. So I think Yeah, I think it's different and the things he's saying make a lot of sense to me.
I wanna tell you one thing about doing tech now versus 20 years ago. I've been investing for a long time in addition to running companies. And 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. Like the stack, the AWS, the tools, the open source, it's pretty easy to assemble the right libraries and right people to help put something together. Companies fail today for one of two reasons. Either there's a founder implosion and they create a toxic culture and people like hate their boss and they hate working there and they all leave, which unfortunately happens all too often. They, they fail the culture code. Or number two, they built a nice product, but it's a rare problem that no one cares about. And unfortunately, a lot of founders have an itch to scratch, as you were saying earlier, Sam, and they get really obsessed about it. Like, I have this little problem, I'm going to work on it for 10 years. And they don't realize that not a lot of people have that same problem. It makes me sad when I see that, when I see a beautiful product that solves a problem I don't care about.
Yeah, you see that all the time. That's like the number one cause of death, I think, with, uh, with startups. You, uh, you said something a second ago I wanted to, to ask you about. So you go, become amazing at recruiting. I, um, that's never been something that I was like, that's the thing I'm going to set my mind to. And you said, you know, I read all the books, I read, I listened to all the podcasts and try to become amazing at this so I can assemble teams to, you know, do your venture studio.
And, um, you're pretty good at it though, Sean.
Well, I'm just like, I don't know.
You never know.
Right? Like even, uh, whatever, you know, like 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, there's, they're like, oh, And 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, the 80/20, the summary of what principles you think are most important when it comes to recruiting. And are there any that you wouldn't expect? Are they all just things that's 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?
The main thing is just recruit all the time. Always, always be recruiting and always be trying to connect with people. And you might be going to a, you know, a coffee social to learn about why crypto is terrible. Or whatever, and you don't realize there's someone going to be there that will 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, 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 once about my recruiting strategy.
That's the best, by the way. That's the best starting of a story.
So go ahead.
Yeah, I'm like worked up.
Okay, so someone asked me about my recruiting style because if If you've been recruited by me, you'll know that I'm like very, very aggressive to do whatever it takes to get you. I'll come meet you at a Starbucks near you. I'll do whatever it takes to get you to meet my team. I've trained my team how they should behave in their first meeting with you and all that. And the first thing that came to mind when someone asked me about this, about why I'm so laser-focused on getting these people, is one time I was in 7th grade at Boston Latin School and I was at my locker and this really cute girl walked by and my friend noticed me turn my head and look at her. My friend said, "English, don't even think about it. She's dating the captain of the football team." So at that moment, that girl went in color and the rest of my world was black and white. Like I had to date that girl just 'cause my friend said I couldn't. And I did end up dating her, but it was just like when I recruit and I see someone amazing, I'll always ask them like, "Do you know anyone even more amazing than you?" There's a funny Japanese game show that is a guy in Italy looking for the most beautiful woman in the world. And when he encounters the first beautiful woman in Italy, he says to her, "Do you know anyone more beautiful than you?" And that leads to kind of a hilarious succession of conversations. But when I'm recruiting and I find someone amazing, I'll just do what it takes to get them excited and to get them to meet my team. And I've always said that the first 5 people hire you the next 50, who hire you the next 500. And it's one thing as a founder to convince someone to come meet your company,. But if you've been really good at recruiting that first 5, those 5 will close the candidate for you. When they meet those 5, they'll say, oh my God, I need to work with this team.
You kind of have— I'm, I'm clicking around on your site. You, you and Dharmesh are interesting to me because you guys have this like dry kind of almost nerdy sense of humor that I love. So for example, if you go to Lola.com, it, it basically says the domain's for sale, but you can see the history of Lola by clicking here and it goes to PME, that's you, .org. And it's a website where it's like plain text. You're just explaining exactly what happens. And so that's kind of an interesting way of like going about explaining the story. But if you click paulenglish.com, it goes to your website and it talks about some of your cool investments and your, your founder stories and things like that. And then it says like all the clubs you're involved in. And one of them, it looks like either you started or you are part of the Bipolar Social Club. I was reading on your Wikipedia, it talked about like, you know, you had some issues with bipolar. And I think that like the fact that you're part of Bipolar Social Club is that's— I mean, that's just like, that's pretty funny. You know, I like, I like guys like you and Dharmash. It's why I love Dharmash. He's this guy who's like, you talk to him and you're like, oh, you're just a shy You're, you're pretty shy. And then you start talking to him a little more and it's like, oh, you might be like quiet, but you're like, you're kind of a killer and you're incredibly quirky. For example, he's got a new project called vennDiagram.com where it's a community for people who love Venn diagrams. And, uh, and then he has another thing called like Wordplay or something like that where it's like a Wordle, you know, game that makes like 100 grand a month or something crazy like that. And he just has all these things. You kind of seem like that. Are you a guy who's just constantly tinkering on, on, on stuff?
Yeah. I mean, I have, um, I own about 300 domain names and every domain name has a Google Doc associated with the idea for the company. Um, I'm obsessed with brand and names and I'm, and Dharmesh and I share this, that we're prepared, prepared to spend big money to buy a good name. And, um, I do, I do a, I have lectured at a lot of universities and I give a lecture on where creativity comes from. And I've done this everywhere from Berklee School of Music, Dartmouth Film School, Rhode Island School of Design, as well as the more traditional universities you would think about. And what I do is, let's say I'm teaching Thursday at 5 o'clock. At 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 which annoys you. And then I teach the students about how irritation becomes inspiration and how any problem can become the motivation for a product. And we go through a very specific exercise about how to do that. And I am someone who loves ideating. If you look at— they say that you're the average of the 5 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 who I hang out with, They care about nonprofit work philosophy and ideating, like improving things. I just have a blast meeting with people like Dimash and saying, how can we fix this? How can we do this better?
Well, you're in the right spot. So we start— when we started this podcast, it was, it was doing all right. Maybe, I don't know, 10,000 people would listen to every episode. So maybe like, I don't know, 100,000 in a month, something like that. And, um, it was a classic interview show, similar to what we kind of have done so far, uh, up, up till now, getting to know you a little bit. Where it's like, oh, oh, you built Kayak. Amazing. Tell me about it. You know, how'd you do it? And, uh, it was just like every other tech or business podcast, which is a how would you do it podcast. And then one day, uh, just to mix it up, I was like, I invited Sam on. I was like, Sam, let's just shoot the shit like we do when we're not on a podcast about 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. And we just started brainstorming. And so we turned the podcast, we called that one the Million Dollar Brainstorm, which is basically ideas that we don't have the time to do, but, um, there were ideas that we thought could be like, you know, million-dollar, billion-dollar ideas. And, um, and so we started, that's what we, and then the whole podcast took off. And so now it's like in the top ranks of the charts and all this stuff. And it's, I think because we switched into this like ideating brainstorm mode and there's a lot of people like us that are out there the same way Dharmesh is trying to find all the Venn diagrammers out there, all the Venners. 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 or maybe from your domains, you know, pull 3 names and, and the, and what's the, what's the one-line pitch you have in mind for, uh, for some ideas that you'll probably never have time to go do?
Sure. Um, 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 that 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, I 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 going to make any money doing that, but I did it because I needed to know where to meet people in New York as 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 want to swap info, it's annoying to do it. You know, you got to type in phone numbers and stuff, you got to type in email addresses. So dumb. Or you 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 sec— a, 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 with 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.
How many people are using this? This looks cool. I'll use it. I just needed one of those things the other day.
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, and we went to San Ambrose in West Village for our first date 3 years ago. And next to us was Anna Wintour. I don't know who she is. She's the editor of Vogue magazine, one of the top socialites in New York. And Bradley Cooper on our first date, they sat next to us. Last night was our 3rd anniversary. We go to the same restaurant. Guess who's sitting next to us? Anna Wintour. That was super cool. But at the end of the meeting, I, I did talk to her for a couple minutes and then she left. And then the table on the other side of me was 4 people who work in the fashion industry where my girlfriend works. And we really kind of bonded to talk about it. I talked about the Bipolar Social Club and the clothing brand I want to create, and then they asked for my number and I just pulled out FunContact and I scanned it. Now all these young fashion people have my number and we've been messaging each other today about Bipolar Social Club. That's great.
What's the clothing brand you want to create?
So bipolar— 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, ruining their marriage or their job or their lives. And it took me a good 10 to 15 years to learn how to manage it for myself. There's bipolar 1 and bipolar 2. I'm bipolar 2, so I'm not the most severe type. The most severe type hears voices and they end up homeless and, and, or worse. Um, not that there's a lot of things worse than being homeless, but Bipolar I is a pretty serious illness. Bipolar II still has problems, but over the years I learned how to deal with it. And I want to be able to laugh with other people with bipolar about the funny things about being bipolar. So I created this video series. If you go to bipolarsocialclub.org, there's 10 people with bipolar illness who kind of tell their journey. And it's kind of destigmatizing it, saying, yeah, it's a mental illness and there's some shitty things about it, But there's some funny things about it too. And I have this thing about bipolar people that if I'm at a cocktail party with 100 people and there's someone like on the other side of the room, I can tell they're bipolar. Like, 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. And we're trying to do something fun. So we want to have a clothing brand where bipolar people kind of wear the brand, they're proud of it, like bipolar and proud. So Bipolar Social Club, we wanted just sort of a fun name.
Is there anything in, uh, in the travel industry that you noticed? Uh, I mean, because you had more data than, you know, 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, 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 big businesses?
The problem with the travel industry is the thing that I have the most trouble with is flights and airports and TSA. TSA is a joke. The stuff they do to you, it 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. 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. And obviously they don't want that to happen. So it's very archaic and old. And I said earlier that I travel between Boston and New York. I never fly because by the time you go through TSA security and get an Uber in each end, it's just, it's often faster to drive. So as far as things in the, in the travel industry I would like to see fixed, I'd like to see someone that figured out how to work with all the unions who put all these requirements in, who working on the airlines, how to work with TSA, how to make flying pleasurable. It's not pleasurable now. I also remember growing up when you go to the airport, people used to dress up. They were like 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.
Yeah, same. It sounds like the hardest thing on earth to do though.
What do you think about what Elon's doing? So Elon buys Twitter, he's kind of taking this technology first thing. He's trying to change the culture overnight, force people back in the office, lay off a bunch of people, try to ship changes really fast. Seems a little bit helter skelter. Have you followed that? And I'm curious, what's your opinion as a CTO and somebody who's done tech for a long time?
I followed it quite closely and put me on the list of 1,000 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 think 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. 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 fuck. Like, do you really need— you are the richest guy in the room, 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. And so when I saw that, I kind of turned on a little bit and I said, I don't like this guy having this much power that he's trying to control. He's trying to 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—
do you think he's gonna pull it off?
He does stupid things like the ape doll verification. That was a joke. Um, but if he assembles smart people around him— it looks like the smartest people all have left Twitter already. They've all run for the hills. But he's going to hire some new people in. I'm sure there's some good people that are still there. I'm sure 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 that has hundreds of millions of users because even if the product is better, does Stephen King really want to tweet on sampower.com where there'll be, you know, 1,000 followers as opposed to Twitter where he'll have a million followers? But I don't know. I think he stirred stuff up. And I want to see the innovation that comes out. That's cool.
Um, yeah, I think that there's a, I think if somebody's going to do it, they're going to have to come up with a, uh, a social innovation, not a, uh, it's not a technical, it's not a technical innovation. Um, so I have this kind of long-running theory about social networks, which is that every social network is a change in privacy policy. Not a change in technology. So like, for example, you know, uh, Facebook was this privacy policy change where it was like, instead of MySpace, um, 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 Uh, 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 or right, like in 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 going to follow on this thing. And so what's interesting with Twitter is if you're going to compete with Twitter now, I think you got to do one of two things. You got to do it like kind of like Gab or Truth Social is 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. Um, and then the other one is I think if you created, uh, You have to turn the disadvantage into an advantage. So instead of Stephen King saying, why do I want to go tweet here when there's only, I'm only gonna have 1,000 followers over here, you have to make it where it's now benefit, like the perk is that there's only 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 or 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 decentralized Twitter. And it's like, nobody cares.
Uh, yeah, I think the decentralized is a joke. Um, I think that's technology looking for a solution. I think Truth Social was an epic failure. Um, the things that I care about on Twitter right now is I'm bothered by all the trolls and the cruelty. And, um, you know, I look at TikTok and I don't watch TV really, but I use TikTok probably 20 minutes a day. And I like how positive TikTok is. And I don't know what the Chinese are doing to filter out the trolls, but it's also just—
it's young people. Like, the average 18-year-old is like kinder than the 18-year-old.
No, you know, do you think that's true?
I 100% think it's true. I 100%— I think that like 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.
Twitter— I mean, TikTok is amazing. Someone will post a video themselves and they'll say, oh, my girlfriend just broke up with me, and, you know, I think I'm very unattractive, or something like really revealing and awkward. And the comments are just unbelievably supportive. Yeah, it's just amazing. It's so different than Twitter. And so what I want to do as a Twitter competitor is create the kind Twitter where there's no trolls, there's no cruelty, and then also deal with the misinformation. When you see a tweet that says COVID vaccine causes autism. Like, how do you smack that down? And I'm very interested in those two problems, getting rid of cruelty and flagging misinformation, but doing it without filtering out independent info. Like, there's a lot of places in the world right now where it's scary to be publicly identified and to state your opinion, and maybe even the US if you are Um, there's certain personal problems, like some people might not want to say they're bipolar because maybe that will hurt their career. Um, but I think this— I think this— there is a way to build something like Twitter that is kind and truth-oriented. And I haven't spent a lot of time in the last two weeks brainstorming with some other people also thinking about doing something new, and 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.
Paul, we, um, I'm going to ask you one last question before we have to move on to the next segment, but, uh, what's your domain portfolio worth right now, you think?
So I have 300. Let's say it cost me $10 each a year, so I'm spending $3,000 a year in domain fees. I've paid hundreds of thousands of dollars 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. So most I hold on. Occasionally someone will, uh, motivate me, like a young entrepreneur who has an idea for a domain that I'm not doing anything with, and I'll sell them 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.
Lola would be mid-six figures, I would imagine, right?
It's up for sale again.
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. Uh, okay. Um, amazing. And, uh, where should people go find you? I'm on your website. I think your website's pretty cool. You have like Here's how I manage my time. Here's how I run meetings. And I love when people do that, when they put their like operating playbooks out there. Um, is that the best place to follow you, or should Twitter?
Yeah, I'm talking 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.
Awesome. Well, Paul, thanks for coming on.
Appreciate it. Yeah, we appreciate you doing this. Um, and, uh, I'm, I'm on your Bipolar Social Club. I don't think I have bipolar, but I still think it's fun to follow along the site.
So awesome.
Thank you. And we appreciate you coming.
Thanks a lot, guys.