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 blown through my four one K to finance it. Alright, Paul, what's going on, man? Will you uh Darmesh uh CTO Co founder HubSpot. Told us we have to s we have to we don't we don't have to, but we should talk to you.

What a Why did he say that? I don't know. It's gonna be connected. Um Have a lot of

uh fun talking together about technology, philosophy and teams. Um One fun thing that Damesh and I did Going back many years ago now, when I was CTO Co founder of Kayak.

Damash and I kinda switched jobs for a day. So I actually had him made up I got him an email address, Domash at Kayak.com and made up business cards. And he basically sat at my desk at Kayak for a day, and then I sat at Hub Spot 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 um he's been a great mentor to me and friend.

And your big hit. has been well, so far, you have a new company, Lola, which I don't know if you know this or not. You guys advertise with my old company, The Hustle, a bit. So 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 two or three billion? Two billion. I've actually sold six companies in a row, including Lola. I've sold even another one after Lola, Moonbeam, which is a podcast out. And now I'm onto my seventh company. Yeah.

Which one of the w so which of the six has been the most financially successful for you? Cog was the biggest financial outcome. Um, which um Deeply appreciative of And I learned a lot at K met some amazing people.

But there's other things which are also really significant that aren't just monetary So my first sale I have don't have to I just told you I sold six 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 six? So I had to come pick up Bars and Late.

We were an e commerce company. We let people set up storefronts a little bit like Shopify, but this was back Twenty years ago we sold that to Intuit. I had again V V technology for Intuit. Then I had a company called Intermute, which is internet security software. I did that with my brother Ed English. We saw that to Trend Micro. I did a company, get human dot com, which is served customer service information to over two hundred million people.

I uh Moonbeam the podcast player, Lola, which is the business travel and expense. And did I forget one? I think that's Celeste. And so what's the like

Um Thought process. So d would 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 kayak.

My co founder, Steve Halfner, was one of the founders of Orbitz. And he had observed in orbits that seventy percent of the people that are searched on orbits. But then when they were done, they opened a second browser and went directly to United.com, remember to buy the ticket. And so Orbits did all the searching for people but never made money. And so Steve based 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 directly to United and they could buy it there. And that was his observation. We met by chance. And within probably forty five minutes. decide to sign up as co founders. He's put a million dollars into the uh

Original ro round of financing. And then I very quickly owned it. From a product standpoint. I went I remember I spent an hour on a speaker that night. Because Xpeedy was the market leader at that point.

And just going back the next morning saying this isn't gonna be hard.'Cause I looked at Expedia's blow where It was sort of seizure inducing. There was so much stuff going on on the screen. You put a million dollars in, was that like A I'm put I'm going all my chips on the table right now, or was that a

You know, was that half your net worth? Was that a s small bet for you? How did you feel at that time? Was did that add some anxieties to the process? I just sold a company for thirty million, so I could have the the million wasn't that hard for me. At that point. Oh, my prior company that I sold for thirty I blew through my four one K to finance it. So my f my first company Was tough financially.

uh to get it going. But for kayak I had made some money, so I could afford to um Help finance it. Why did you why do you sell your companies? Why not, you know, try to run them or have them exist on your a management team that you you control for a long time. Like Darmesh, right? Darmesh has been doing HubSpot for forever. Yeah, so kayak I did for ten years. That was my longest stint. And we ended up taking it public twenty twelve, which is incredibly fun.

And then we sold it shortly thereafter to price on a really booking dot com, which is the parent company. And I just frankly was bored. I felt like I was editing the flight screen for ten years. And I want 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. 'Cause 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 kinda like an internet OG a little bit. I mean, kayaks 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 er early on into 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 ac across the industry. Oh, right. Yeah, because like Darmesh 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 he I'm sure there's like a story he's 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 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 in a billion dollar valuation and I think they're now worth a hundred billion or something like that. And I remember the time, like loving Brian, thought he was Iconic. Um

And passion driven Mission driven. But um I didn't see it, how big it be

I said this seems Awesome for people who want to have strangers living in the house, but how many people is that gonna be? So I kinda missed the bigger picture there. Um What was he like? When you met him.

Just kidding. 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. Um, but what did you see? I saw him as very serious and intense. Um

He was charismatic, he listened well, so we had a good conversation. where he wanted me to give him feedback of the company because Cyc was a much bigger company at that point. And um Yeah, I just took him as very serious, intense. And charismatic.

Yeah, whenever you're like you're doing technology for like fifteen, twenty years You just get this like crazy story arc or like, you know, um you get to see people You can 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 kinda in the game.

For such a long time. Yeah, so when we financed We card was created in two thousand and four. Uh, we really launched out of general catalyst in Cambridge Mass. And then we raise money from Mike Moritz Takoya.

I remember one day my co founder and I were working out of square office. And my Morit said, Oh I wanted to use it a couple of guys. This is Chad Hurley and I've got his co founder, but they were the founders of YouTube. Steve Chan, I think. Yeah, that's right.

And I remember meeting those guys that square office. And Mike's like, Yeah, these guys are like putting videos online. I'm like, Yeah, that's cool. Whatever. Okay. I didn't see that one either. I have I have some famous misses

I mean I've been very lucky as an investor. Um I think my IR is thirty point five percent over the last several years. So I've been pretty good. I've invested in sixty companies. But I've missed some. I missed Snapchat. I met one of their founders when they were financing an eighty million dollar valuation.

That would have been a big outcome. Uh 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 could be plagued by security. I'm still kinda shocked. I use Dropbox. Do you know that they don't really encrypt your files?

And then a Dropbox engineer, if they were malicious, I can get out 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 anything. Yeah. What have been what have been the uh f you said you've invested in sixty companies and you got this great IR. What have been some of your the hits so far? Um, one of the ones going on right now is pilot.com.

I use it. Yeah, that's an amazing company. I met those guys when they were I was a judge of the MIT hundred K competition. And it had a coming out casewise.

really exotic technology. They could Patch. A Linux operating system as 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 invest it in their next company, Zulup, which they ended up selling to Um 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 forty XR.

I think I finance them I wrote a check as part of the rounded thirty million dollar valuation. I think Their last valuation was like one point two billion or something. But that's one that The founding team had the mojo. So when you met them, you just knew those guys gonna create something serious. They They were intense, high energy, they laughed a lot, they finished each other's sentences.

They just really enjoyed working together. Um I also another good return for me at twenty two X was Ken show. Which is a competitor to a Bloomberg terminal.

And I invest in um because their CO Pete Cruscoe 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 Trong work for us, so Trong was an analyst at Ken Show. And Ken Show is like this Uh you know, they're a startup still, but like uh the stereotype the to me, from an outsider, they've kinda fit this like stereotype of like an uptight financial firm.

And We found Trunk working there. And This guy Trunk 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 and now he's got like, you know, a million followers on Twitter and we and we recruited him from Ken Show. That's right. Uh I I like Ken Sho 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 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, l 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 kinda have a an exit like seven hundred million or eight hundred 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 got to get huge now. And others are like No, I'm literally just gonna program things in my house for fun now. Like now I uh I I don't wanna 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 always said for each of my companies it's team first, customer second, profit third. I set up for kayak on day one when we put together our culture plan. And I really think that'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 to 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 magic 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 B V S dot net. And we have nine apps under development. Some of them are an itch to scratch, like fun little things that we put out with source code. Um, others are a swing for the fence is really thinking 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. 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 there's thirty seven thousand 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 a thousand five star views 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 have to detect them. They're going through proxy servers, they have age accounts, they buy products. Um and then if you go to Yelp or TripAdvisor. Their reviews are largely by people you don't care about. You know, like I um

Looked up a sushi restaurant in New York. And I saw five star views of this place. People talked about how great it was because it's really cheap. And I don't know about you, if you like sushi or not, but I'm not trying to be that excited. having ten dollars a person for sushi in New York, that's a little scary to me. 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 five star hotel five star reviews from Motel Six. And that was great when I was twenty years old. I'm not sure I would stay at a motel six now. But um a lot of these just don't relate to the person doing the purchase. So the idea of deeds is gonna blow that up and say it's just the recommendations from your friends. From influences that you choose to follow

And then using machine learning doing look alike modeling to find people that are similar to you. Man, it seems like you pick really hard industries. Like Uh travel is like Uh uh you know, I'm uh again, I'm an outsider. You're you're the expert, but it seems like notoriously difficult. Like it just seems like incredibly competitive and in very, very, very challenging and the margins seem small. 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 five or ten years. Their stock sucks. Uh Google Reviews is is a is a horribly challenging person to compete with'cause 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 Dizza is I ha 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 this like mafia. Well, you pay if you they call you save a lot of bad reviews, crawl us and pay us. hundreds of dollars a month it will sort of clean up your

Site on Yelp. It's kinda like In Italy. There's a movie called Billion Dollar Bully. About Yelp. It came out in twenty nineteen and the opening scene is an Italian shaft. Who said when he opened his first restaurant in Italy his son broke the windows, he fixed'em. They broke them again the next week. He fixed them.

The next week some guy comes in and says, I noticed someone keeps breaking the windows If you pay me a hundred dollars a week, I'll make sure no one breaks the windows anymore. And he knew that was the guy who's breaking his windows. He's like, Yelp was just like that. So I look at Yelp as a twenty year old dinosaur. That's the last twenty years. We want to be the next twenty years. And I look at the evolution, you know, the world is different now than it was when the output created.

For one, the rise of the influencers Particularly Gen Z. They make all their purchase decision based on influencers. And that's true now for dining. So we wanna give it make it really easy. Right on 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 You know, what are your 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 have a new dog.

Um, this gardening it 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. look alike modeling or user clustering. So we're doing that with these as well. We're gonna find your friends. The influence 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. Whoa, I can see the client's whole history. Calls, support tickets, emails, and Here's a test from three days ago I totally missed.

Spot grow better. Do you think that starting a company now that you're wealthy is easier or harder than when you are 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 blown through my four one K 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.

They cost five grand to fix. You know, when you're creating your first company you don't have that five 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 the pros and the cons, right? Like

Yeah, recruiting is easier. And you waste less time on the On s 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 fifty questions to show you something good. And now you could swipe three times, four times, and I can 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'm gonna tell you one thing about doing Technobers twenty 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. Um

It's pretty easy to assemble 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 gonna Working 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 that, when I see a beautiful product that solves a problem I don't care about.

Yeah, do 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 Uh become amazing at recruiting. I um That's never been something that I was like that's the thing I'm gonna set my mind to. And you said, you know, I read all the books, I've read listened to all the podcasts and try to become amazing at this

So I can assemble teams to to you know Your studio. Yeah, 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, 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, I'm 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 um Give me like the the the eighty twenty, the so the summary. Uh what

Principles you think are most important when it comes to recruiting. And w 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 help not that helpful. I kinda already do that. Are there any things that are maybe counterintuitive? or uh or nuance that 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 uh You know, a coffee social Learn about. My crypto's terrible.

Or whatever. Um And you don't realize there's someone gonna 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.

Um, I have a little bit of an off colour story, which I probably shouldn't tell, but Um someone else who wants about the strategy. By the way, that's the best starting of a story. So go ahead. I mean I'm I like work Okay, so someone asked me about my recruiting style because 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 get and meet my team, I train my team how they should Um 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 Yeah, one time. I was in seventh 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 cap on 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've always asked like Do you know anyone even more amazing than you? I just 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 leaves us kind of a hilarious uh 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 five people hire the next fifty who hire the next five hundred 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 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. You kind of have I'm I'm clicking around on your site. You you and Darmesh 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 domains for sale, but you can see the history of Lola by clicking here and it goes to uh PMD. P M E that's you dot 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 a an interesting way of like going about uh explaining the the the story.

But If you click Paul English dot 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 that I mean that's just like that's pretty funny. You know, uh it y I I like

I like guys like you in Darmash is why I love Darmash is 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. Then you start talking to him a little more. 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 a hundred grand a month or something crazy like that. And it 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 three hundred domain names and every domain name has a Google Docket associated with the idea for the company. Um, I'm obsessed with brand and names and I'm

And Darmesh and I share this that we're prepared Prepared to spend big money to buy a good name. And um I do I do it. I have lectured at a lot of universities and

I give a lecture on where creativity comes from. And I've done this every day where from Berkeley School of Music, Dartmouth Film School, Burn 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 five o'clock. It Wednesday at five 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 sometime 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 five people you spend most of your time with. If you wanna change your life, change the people you spend time with. If you look at the people who I hang out with. They care about

non profit work, philosophy, and ideating. Like improving things. I just have a blast. meeting with people like Demesh and saying, How can we fix this? How can we do this better? Well you're in the right spot. So We st when we started this podcast.

It was it was doing all right, maybe, I don't know. Ten thousand people would listen to every episode. So maybe like I don't know, a hundred thousand in 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 till now, we're 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?

Yeah, 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 they 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

I dating brainstorm mode. And there's a lot of people like us that are out there. The same way Darmesh 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'em. So Can you give us a couple of

ideas or maybe from your domains, you know, pull three 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 Tobacco.

Yeah, so um 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 Uh Upper West Side. I don't know what I mean.

I'm like this is annoying that There isn't a website. Where they can See they where they are, where I am, and pick a bar in the middle. So I built

An hour. It's called middle dot net. I went I bought that domain name. And middle dot net. allows you to have two people or three or four, 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. No, 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 as I was getting used to the city.

I couldn't find a way to do it, so I built them out. Um Another one. When you meet someone, so I generally don't really like going to conferences, so 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 like that, or type in email addresses. So dumb. Well we can use this dot card thing, but if to carry this card around this card around So

I designed a little app called Fun Contact. It's funcontact.com. And allows you to have a sex A s 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, which information I want to share them, I just swipe through and show them the right QR code, they scan it, and I'm in their address block.

Um, I built that'cause I needed it. I don't think it'll ever become a company. But I just wanted that. So I felt that How many people are using this? This looks cool. I'll use it. I w ch I just needed one of those things the other day. It's super cool.

Um I used it last night. Oh, do you want to hear a funny story? Yeah. So Last night was my three year anniversary with my girlfriend Rachel.

And We went to San Ambrose in West Village for our first date three years ago. And next to us was Anne Wintour. I don't know who she is. She's the editor of Vogue magazine, one of the top socialists in New York. And probably Cooper. On our first day that sat next to us.

Last night was our three anniversary. We go to the same restaurant. Yes, who's sitting next to us on a wind tour. 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. Whereas four people work in the fashion industry, where my girlfriend works.

And we really kinda bonded to talk about a number I talked about the bipolar social club, the clothing brand I want to create. And then they asked for my number and I just pulled out Fun Contact and I scanned it. Now all these Young fashion people have my number. Yeah, messaging each other today about bipolar social club.

What's the clothing brand you want to create? So Bipolar. I have my holiday illness. I was diagnosed at age twenty five. And it's a pretty serious illness.

You know, a lot of people end up killing themselves. ruining their marriage or their Job or the lives. And it took me The good

Ten or fifteen years to learn how to manage it for myself. There's bipolar one and bipolar two, I'm bipolar two, so I'm not the most severe type. The most severe type has voices and they end up homeless and And or worse. Um, not that there's a lot of things for us and being homeless, but Rapula One is pretty serious illness.

My Polo Two still has problems, but over the years I learned how to deal with it. And I want to be able to Laugh about being bipolar, about the funny things about being bipolar. So I created this video series. If you go to BipoloSocial Club dot org. There's ten people with bipolar illness who kind of tell their journey.

And it's kind of destigmatizing it, saying now 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 in a cocktail party with a hundred people And there's someone like on the other side of the room

I can tell they're bipolar. Like we've recognized each other. My gay friends say they have gay hour, 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 kinda we're the brand, the prouder like Bipolar and Proud, so Bipolar Social Club. We want 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 th uh low digit thousands that are able to s 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? Yeah. Big businesses.

The problem with The travel industry. Is The thing 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 security, but there's no real security with T SA. Um that's irritating. I wish

Someone would solve that and make something a lot more efficient. And Uh 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 um I'd said earlier that I traveled 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 Figure out.

How to work with all the unions. Who put all these requirements in, who working on the airlines. I 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 a the hardest thing on earth to do, though. What do you think about what Elon's doing? Uh so Elon buys Twitter

He's kind of taken this like uh, you know, technology first thing is try 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 in 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 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 Test of Cars. I'm a happy Tesla Star Quarter from two thousand sixteen. Um, but when I looked at the way he fired people at

Yeah, Twitter. It was just obnoxious as fuck. Like, do you really need you're 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 kinda 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 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 eight dollars verification, that was a joke.

Um But if he s assembles smart people around him, it it it looks like the smartest people all have left would are already They've all run for the hills. But he's gonna 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 are gonna come out. It's hard to compete with An entrenched Com company that has hundreds of millions of users because even if your product is better. Does Stephen King really want to tweet on SamPower dot com?

Where there'll be, you know, a thousand followers as opposed to Twitter where it'll have a million followers. But I don't know. I think you stirred stuff up. And I wanna see the innovation that comes out. That's cool. Um 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 uh A social innovation, not a uh

It's not a technol it's not a technical innovation. Um 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, uh Facebook was this ch 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 change 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 is like here's the privacy policy here. All the shit self destructs in twenty four hours, or right, like in ten seconds, whatever. So content is not permanent here. And so people flag to that. And so there's just this ongoing shift of like the uh 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 two 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.

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 have a thousand followers over here. You have to make it where it's now benefit like the perk is that there's only a thousand people there. So it's like More like private or in l 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 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 T V really, but I use TikTok probably twenty 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 it's also just it's young people. Like the average eighteen year old is like Kinder than the eighteen year old. No. Do you think that's true?

I one hundred percent think it's true. I one hundred percent 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 eighteen. 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. Well, 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 flag 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're 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 there's I think there's there is a way To build something like Twitter. That is kind and truth oriented.

And I've been spent a lot of time in the last two weeks bringing some of 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 wanna ask you one last question before we have to move on to the next segment segment. Wh but uh What's your domain portfolio worth right now, you think? So I have three hundred. Let's say it cost me ten dollars.

each a year. So I'm spending three thousand a year in domain fees. I 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 cause you to buy the domain so most that hold on. Occasionally someone will

uh motivate me. Like a young entrepreneur who has an idea for demand that I'm not doing anything with and I'll sell them to them. I don't know, I have some that are worth hundred thousand dollars or more. And I have some that are just funny, probably just to me. So I'm not trying to.

Lola would be mid six figures, I'd imagine, right? We paid five hundred thousand to buy Lola. We were in a bidding war. It it's up for sale again. I would for sale. Yeah,'cause 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 back. Possibly. Uh okay. 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. 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 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, Paul English dot com. Awesome. Well, Paul, thanks for coming on.

Appreciate it. Yeah, we appreciate you doing this. Um And uh I'm I'm I'm on your uh Bipolar Social Club. I don't think I have uh bipolar, but I I still think it's fun to follow along the site. So thanks for doing this. We appreciate you coming. Thanks a lot, guys.

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