My First Million - Paul English: How He Built And Sold 6 Companies And Why He Believes Irritation Becomes Inspiration

Episode Date: December 9, 2022

Episode 394: Shaan Puri (@ShaanVP) and Sam Parr (@TheSamParr) talk with entrepreneur and Kayak co-founder, Paul English (@englishpaulm) about his latest business ideas, his famous missed investments, how to become a strong recruiter, and why he wants to create Twitter's competitor. ----- Links: * Paul English * Boston Venture Studio * Middle * Bipolar Social Club * Do you love MFM and want to see Sam and Shaan's smiling faces? Subscribe to our Youtube channel. * Want more insights like MFM? Check out Shaan's newsletter. ------ Show Notes: (00:25) - switched jobs for a day (07:05) - who did you know before they met success (13:45) - become an excellent recruiter (20:25) - starting a company easier now? (28:15) - Irritation becomes inspiration (30:55) - Ideas he's working on (34:10) - Bipolar disorder ----- Past guests on My First Million include Rob Dyrdek, Hasan Minhaj, Balaji Srinivasan, Jake Paul, Dr. Andrew Huberman, Gary Vee, Lance Armstrong, Sophia Amoruso, Ariel Helwani, Ramit Sethi, Stanley Druckenmiller, Peter Diamandis, Dharmesh Shah, Brian Halligan, Marc Lore, Jason Calacanis, Andrew Wilkinson, Julian Shapiro, Kat Cole, Codie Sanchez, Nader Al-Naji, Steph Smith, Trung Phan, Nick Huber, Anthony Pompliano, Ben Askren, Ramon Van Meer, Brianne Kimmel, Andrew Gazdecki, Scott Belsky, Moiz Ali, Dan Held, Elaine Zelby, Michael Saylor, Ryan Begelman, Jack Butcher, Reed Duchscher, Tai Lopez, Harley Finkelstein, Alexa von Tobel, Noah Kagan, Nick Bare, Greg Isenberg, James Altucher, Randy Hetrick and more. ----- Additional episodes you might enjoy: • #224 Rob Dyrdek - How Tracking Every Second of His Life Took Rob Drydek from 0 to $405M in Exits • #209 Gary Vaynerchuk - Why NFTS Are the Future • #178 Balaji Srinivasan - Balaji on How to Fix the Media, Cloud Cities & Crypto * #169 - How One Man Started 5, Billion Dollar Companies, Dan Gilbert's Empire, & Talking With Warren Buffett • ​​​​#218 - Why You Should Take a Think Week Like Bill Gates • Dave Portnoy vs The World, Extreme Body Monitoring, The Future of Apparel Retail, "How Much is Anthony Pompliano Worth?", and More • How Mr Beast Got 100M Views in Less Than 4 Days, The $25M Chrome Extension, and More

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 401K to finance it. All right, Paul, what's going on, man? Darmesh, CTO, co-founder, HubSpot told us we have to, we don't have to, but we should talk to you. Why did he say that? I don't know.

It's going to be connected. Domesh and I have a lot of fun talking together about technology, philosophy, and teams. One fun thing that Domesh and I did, going back many years ago now, when I was CTO, co-founder of Kayak, Domesh and I kind of switched jobs for a day. So I actually had him made up, I got him an email address, Darmash at Kayak.com, and made up business cards. And he basically sat at my desk at Kayak for day, and then I sat at HubSpot for 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 advertised with my old company, The Hustle, a bit. So we worked with you a bit. But your big hit so far has been kayak, right? What did you sell that for?

Like $2 or $3 billion? $2 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 app, and now I'm onto my seventh company. Which one of the, so which of the six has been the most financially successful for you? Kag was the biggest financial outcome, which I'm deeply appreciative, and I learned a lot at Kock. I met some amazing people. But there's other things which are also really significant

that aren't just monetary. So my first sale, I just told you I sold six in a row. There's another one that I don't really count because 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 a company called Boston Light. We were an e-commerce company to let people set up storefronts, a little bit like Shopify, but this was back 20 years ago. We sold that to Intuit. I had a MVP 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 served 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 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 Orbits. And he had observed at Orbitz that's 70% 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 and buy the ticket. And so Orbits did all the searching for people but never made money. And so Steve basically said, well, I don't 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 them directly to United and they could buy it there. And that was his observation. We met by chance and within probably 45 minutes decided to sign up as co-founders, each put a million dollars into the original round of financing.

And then I very quickly owned it from a product standpoint. I went, I remember spending an hour on Expedia that night because Expedia was the market leader at that point. point and just going back the next morning saying this isn't going to be hard because i looked at expedia's blow wear it was sort of seizure inducing there was so much stuff going on the screen you put a million dollars in was that like a 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 small bet for you no did you feel at that time was 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

401k to finance it. So my first company was tough financially to get it going. But for Kayak, I'd 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? Like Darmesh, right? Darmesh has been doing HubSpot for forever. Yeah, so 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, the price on a 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 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're kind of, I mean, you're kind of 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 early on in the game. And you guys had a nice huge exit. Who are some of the people who were kind of like big shots and ballers now that you got to know a little bit earlier on? You mean across the industry overall? Yeah, because like, Darmesh has all these crazy stories where he's like, you know, I was an early investor in Coinbase 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 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. Then 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 not worth $100 billion or something like that. And I remember the time, like loving Brian thought he was iconic. and passion driven, mission driven. But I didn't see it how big everybody was going to get. I said, this seems awesome for people, one of strangers living in the house, but how many people look is that going to be? So I kind of missed the bigger picture there.

What was he like when you met him? 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. 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 of the company because Kaig was a much bigger company at that point. And yeah, I just looked at 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. story arc or like, you know, you get to see people, 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 that you've seen because you've been kind of in the game for such a long time? Yeah. So when we financed,

we, conquist, in 2004. We've really launched out of general catalyst in Cambridge, Mass. and then we raised money from Mike Moritz, and Sequoia. And I remember one day my co-funder and I were working out of the Sequoia office, and Mike Moritz said, oh, I wanted to use it 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 in the 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 some famous misses.

I mean, I've been very lucky as an investor. I think my IR is 30.5% over the last several years. So I've been pretty good. I've invested in 60 companies, but I've missed some. I miss Snapchat. I met one of their founders when they were financing an $80 million valuation. That would have been a big outcome. Dropbox I met Drew early on.

And that wasn't under the guys of me investing in them. It was really just networking. But had I, I thought Dropbox is 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? Yeah. What have been the, you said you've invested in 60 companies and you got this great IR. What have been some of the hits so far? One of the ones going up 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 at the MIT 100K competition and had a company called Caseplace. 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 invested in the next company, Zulip, 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 40XR. I think I financed them. I wrote a check as part of the rounded $30 million valuation. 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 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 Ken Show, which is a competitor to a Bloomberg terminal. And I invested in them because their CTO Pete Kresco used to work at Kaya. and I knew him from Kock. And I just knew he was destined to do great things. And that was a really nice exit.

We had this guy Trong work for us. So Trong was an analyst at Ken Show. And Ken Show is like this, you know, they're a startup still. But like the stereotype, to me from an outsider, they 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 loud mouth, 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 Ken Show. That's amazing. I like Ken Show because of that. Thank you. And you, so Kayak was a big win.

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 podcast. Podcasting 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. Are you, do you, I know one thing that's hard. I've talked to people 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 got to get a huge now. And others are like, no, I'm literally going to. just going to program things in my house for fun now. Like now I don't want to go try to catch lightning in a bottle again. Which way 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 set 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 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're 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 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 nine apps under the developments. 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 two weeks ago called Dietz, like Show Me the Deets. That could be a billion dollar company.

What's the URL? 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 competitive of these and you want to sell it on Amazon, you can easily buy a thousand, five-star reviews for that if you want. And these fake review companies are run by PhD computer scientists. They're evading Amazon spot detection.

So it's very difficult. at this point to detect them. They're going through proxy servers. They have age 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 five-star reviews to 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 $10 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 Hotel 6.

And that was great when I was 20 years old. I'm not sure I would say to Motel 6 now, but a lot of views just don't relate to the person doing the purchase. So the idea of Deats, I'm going to 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 travel is like, you know, again, I'm an outsider.

You're the expert. But it seems like notoriously difficult. Like it just seems like incredibly competitive and very, very, very challenging. And the margins seem small. Very hard. It seems to start one of those things now. Podcasting terribly hard. I don't, you know, I don't entirely understand why it's so hard.

but nothing has entirely clicked to make it this fantastic industry, even though a lot of people use podcasts. And then reviews also seem terribly challenging. Yelp has had like, Yelp hasn't innovated in five or 10 years. Their stock sucks. Google reviews is a horribly challenging person to compete with because, you know, they have all these people already using it. What's the game, what's the game plan here?

And why are you picking the hardest things to work on? Yeah, the origin of DETs is 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 where you pay if they call you and they save a lot of bad reviews, call us and pay us hundreds of dollars a month. It will sort of clean up your site on Yelp.

It's kind of like in Italy, there's a, 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 the movie. The next week, he fixed them. The next week, some guy comes in and says, I notice someone keeps breaking your windows. If you're paying me $100 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 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 are created. For one, the rise of the influencers, particularly Gen Z. They make all that purchase decision based on influencers. And that's true now for dining. So we want to 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's your interest? But if you look at my TikTok feed, there's a lot of base players. I'm a bad bass player, but I like bass players. There's a lot of dogs, have a new dog, there's gardening. TikTok has figured out the stuff I'm interested in and without ever asked 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 her that she watches. So I really like that look-alike modeling or user clustering. So we're doing that with deeds as well. We're going to find your friends, the influences you like, and then people have 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 task from three 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 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,

I was blowing through my 401K to finance it. 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 of having money that if you see a stupid problem that cost $5,000 to fix, you know, when you're creating your first company, you don't have that $5,000. Now you do, so you just pay a little money and problems go away. What do you think, Sean?

Easier or harder? Yeah, I think it's different. And you just have to like work with 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, 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 the user experience way different. If before we had to ask you 50 questions to show you something good and now you can swipe three times, four times and I can start getting you something good, 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. The things he's saying make a lot of sense to me. I want to tell you one thing about doing technobrist, 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 feel today for one of two reasons. Either there's a founder implosion. They create.

to talk to culture and people like hate their boss and they hate working there and they all leave, which unfortunately happens all too often. They fail the culture code. Or number two, they built a nice product, but it's a 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 had 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 startups. You said something in a second ago I wanted to ask you about. So you go, become amazing at recruiting. That's never been something that I was like, that's the thing I'm going to set my mind to. And you said, you know, I read all the books, I listened to all the podcasts and tried to become amazing.

at this so I can assemble teams to, you know, do your venture studio. And you're pretty good at it, though, Sean. Well, I'm just like, I don't know. You never know, right? Like even 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, they're like, oh, I'm just, there's lifetimes more to

learn about this thing. But I'm curious, Paul, how would you summarize for somebody who's talented but hasn't put their focus on becoming great at recruiting, what do you think are the, give me like the 80, 20, the summary of what principles you think are most important when it comes to recruiting. 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 anything that are maybe counterintuitive or nuance 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 coffee social to learn about why crypto is terrible or whatever. And you don't realize that someone going to be there that would be your next unbelievable CMO. You weren't expecting to meet them. But if you always have your spiky 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 you once about my recruiting strategy.

By the way, that's the best starting of a story. So go ahead. I mean, I like worked up. 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 it because getting me, my team. I've trained my team how they should behave in their first meeting with you and all that.

And the first thing we 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 seventh grade at Boston Latin school and I was at my locker and this really cute girl walked by. And my friend noticed me turned 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 because 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? It'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 in Italy, he says to her, do you know what I'm even more beautiful than you? And that leads us 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 five 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 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 clicking around on your site.

You and Darmesh are interesting to me because you guys have this, like, dry kind of, of almost nerdy sense of humor that I love. So, for example, if you go to lolla.com, it basically says the domain's for sale, but you can see the history of Lola by clicking here. And it goes to PMD, pm, 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 an interesting way of like going about explaining the story. But if you click Paul English.com, it goes to your website, and it talks about some of your cool investment, and your founder stories and things like that. And then it says like all the clubs you're involved. 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 in Darmash. It's why I love Darmash. He's this guy who's like, you talk to him and you're like, oh, you're just a show. shy, you're pretty shy, and 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 Venn diagram.com, where it's a community for people who love Venn diagrams. And then he has another thing called like wordplay or something like that, where it's like a wordal, 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 stuff? Yeah. I mean, I have, I own about 300 domain names and every domain name has a Google docket associated with the idea for the company. I'm obsessed with brand and names.

And Darmesh and I share this, that we're prepared to spend big money to buy a good name. And I do, I do, I have lectured at a lot of universities and I give a lecture on where creativity he comes from. And I've done this, everything we're from Berkney School of Music, Dartmouth Film School, 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 tonight which annoys you.

And then I teach your 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 want to change your life, change the people who 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 Domash and saying, how can we fix this? How can we do this better? Well, you're in the right spot.

So when we started this podcast, 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 it was a classic interview show. Similar to what we kind of have done so far up until now, getting to know you a little bit. Or it's like, oh, oh, you built kayak. Amazing. Tell me about it.

You know, how'd you do it? And it was just like every other tech or business podcast, which is a how would you do it? Podcast. And then one day, 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? You know, 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 there were ideas that we thought. It would be like a million dollar, billion dollar ideas. 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, Darma 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 three names and what's the one line pitch you have in mind for some ideas that you'll probably never have time to go do? Sure. I'll tell you some ones that the itch was enough that I actually did a little bit of work on it. So one of them was I live in Boston, but I also spend a lot of time in New York where I am today. And where I live is kind of between West Village and Tobacco near Soho. And I don't know New York that well.

Like I know those three neighborhoods, but I don't really know like Upper East Side, Upper West Side, whatever. If I'm trying to meet someone on the Upper West Side, I don't know where to meet, I'm like, this is annoying that there isn't a website where they can see where they are where I am and pick a bar in the middle. So I built an app. It's called Middle.comnet. I went and I bought that domain name. And Middle. Dotnet allows you to have two people, a three or four, as many as you want. it grabs the location from the browser,

and it shows you like a coffee shopper bar to meet in the middle. Now, I'm never going to make any money doing that, but I did it just because I needed to know where to meet people in New York because I was getting used to the city. I couldn't find a way to do it, so I built an out. 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 learned how to be extroverted, and I can say more about that if you care to hear about it. 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 about it. Type in email address. It's so dumb. 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 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 want to share them,

I just swipe through and show them the right QR code. They scan it, and I'm in their address book. I built that because I needed it. I don't think it'll ever become a company, but I just wanted that. So I built it. 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 use it last night. Oh, do you want to hear a funny story? Yeah. So last night was my three-year anniversary with my girlfriend. and Rachel. And we went to San Ambrose in West Village for on our first day three years ago. And next to us was Ann Wintour. You know who she is? Theodore of Vogue magazine, one of the top socialites in New York, and Bradley Cooper on our first day that sat next to us. Last night was our three

anniversary. We'd go to the same restaurant. Guess who's sitting next to us on a winter. That was super cool. But at the end of the meeting, I did talk to her for a couple minutes, and then she left. And then the table on the other side of me was four people working in the fashion industry where my girlfriend works. And we really kind of bonded to talk about a number. I talked about the bipolar social club and the clothing brand I want to create. And then they asked my number and I just pulled out a fun contact 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. 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 or 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, he has voices and they end up homeless and or worse. Not that there's a lot of things worse than being homeless, but bipolar 1 is pretty serious. illness. Bipolar 2 still has problems, but over the years I learned how to deal with it. And I want to be able to laugh with all the people bipolar about the funny things about being bipolar. So I created this video series. If you go to bipolar social club.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 going to 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 that proud are like bipolar

and proud. So bipolar social club, we want to sort of a fun name. Is there anything in the travel, that you noticed, 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 the company that bought you guys. Were there any interesting problems that you felt weren't being entirely solved that you think could actually be quite large, you know, big businesses? 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 that they do to you is gives you a false sense security, but there's no real security with TSA. That's irritating. I wish someone would solve that and make something a lot more efficient

and safer. Airlines are running on old technology. They have to be very conservative because if they make a mistake and adopt something too new, the plane will crash. And obviously they don't want that to happen. So it's very archivalry.

and old. And 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 and each end, it's just, it's often fast at a drive. So as far as things in the travel industry, I would like to see fix. I'd like to see someone that figured out how to work with all the unions who put all these requirements in, who work 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. By 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 like, you know, 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. It seems a little bit helter-skelter. Have you followed that? And I'm curious, what's your opinion as a CTO and somebody'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 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're the richest guy in the room in the world. Do you really need to also be an asshole?

There was no reason he had to march people out of the office. 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 going to. Do you think he's going to pull it off? He does stupid things.

Like the $8 verification, that was a joke. But if he assembles smart people around him, it looks like the smartest people all have left 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 replaces going to come out. It's hard to compete with an entrenched company that has hundreds of millions of users

because even if your product is better, does Stephen King really want to tweet on sampear.com where there'll be a thousand followers as opposed to Twitter will have a million followers. But I don't know. you start stuff up and I want to see the innovation that comes out. That's cool. 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 social innovation, not a, it's not a technical, it's not a technical innovation.

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, Facebook was this privacy policy change where it was like, instead of MySpace, this is only people that go to your school. And at the door, we gate you with your school email address. There's a change in privacy policy that totally changed people's behavior because now you're more interested in everybody and you're more willing to share. Then as Facebook became the norm, then it became, you know, things like Twitter, which was like, change your privacy policy. I don't have to accept your friend request for you to see my content. It's like you could just follow me.

Unilaterally, you could just describe, you could decide to get my content. That was totally different than Facebook. Then Snapchat comes out and it's like, here's the privacy policy here. All the shit self-destructs in 24 hours, sort of right, like 10 seconds, whatever. So content is not permanent here. And so people flock to that. And so there's just this ongoing shift of like the, 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 socials trying to do but somebody could actually pull that off where they basically take a community of people that are pissed off about Twitter and there's enough pissed off people to go into their own echo chamber. I think that's possible. And then the other one is I think if you created, you have to turn the disadvantage into an advantage. So instead of Stephen King saying, why do I want to go tweet here when there's only, I'm only going to 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 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. It's like nobody cares. Yeah, I think that decentralized is a joke. I think that's technology looking for a solution. I think truth social was an epic failure. The things that I care about on Twitter right now is I'm bothered by all the trolls and the cruelty. And, 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. 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 is 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're, there's certain personal problems.

Like some people might not want to say they're bipolar, because maybe that will hurt their career. But I think there is a way to build something like Twitter that is kind and truth-oriented. And I haven't spent a lot of time in the last two weeks, brain something 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, I'm going to ask you one last question before we have to move on to the next segment. But what's your domain portfolio worth right now, you think? So I have $300. Let's say it costs 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 cause me to buy the domain. So most I hold on. Occasionally, someone will motivate me, like a young entrepreneur who has an idea for a domain that I'm not doing anything with and I'll sell 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 checking what the price on that. Lola would be mid-six figures, how to imagine, right? We paid $500,000 to buy Lola. We were in a bidding war.

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 back.

Possibly. Okay. Amazing. And 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. 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, Paulenglish.com. Awesome.

Well, Paul, thanks for coming on. Appreciate it. Yeah, we appreciate you doing this. And I'm on your bipolar social club. I don't think I have bipolar, but I still think it's fun to follow along this site. So thanks for doing this. And we appreciate you coming. Thanks, all, guys.