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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.
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If you talk to anyone who works with me, they'll say I'm working as hard now as I was during my first company when I was blowing through my 401k to finance it.
0:19
All right, Paul, what's going on, man?
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Well, you Dharmesh, CTO, co-founder of HubSpot, told us we have to we have to we don't we don't have to, but we should talk to you.
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What Why did he say that? I don't know.
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It's going to be connected.
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Dharmesh and I have a lot of fun talking together about technology, philosophy, and teams.
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One fun thing that Dharmesh and I did, going back many years ago now when I was CTO and founder of Kayak, Dharmesh and I kind of switched jobs for a day.
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So, I actually had him made up I got him an email address dharmesh@kayak.
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com and made up business cards.
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And he basically sat at my desk at Kayak for a day, and then I sat at HubSpot for a day.
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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.
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And um he's been a great mentor to me and friend.
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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.
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You guys advertised with my old company The Hustle a bit.
1:22
So, we worked with you a bit, but um your big hit so far has been Kayak, right?
1:29
What did you sell that for?
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Like two or three billion? Two billion.
1:31
I've actually sold six companies in a row, including Lola.
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I've sold even another one after Lola, Moonbeam, which is a podcast app.
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And now I'm on to my seventh company.
1:42
Which one of the So, which of the six has been the most financially successful for you?
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Kayak was the biggest financial outcome, which I'm deeply appreciative, and I learned a lot at Kayak.
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I met some amazing people.
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But there's other things which are also really significant that aren't just monetary.
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So, my first sale I don't have to I just told you I sold six in a row.
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There's another one that I don't really count cuz 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?
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So, I had a company called Boston Light.
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We were an e-commerce company that people set up storefronts, a little bit like Shopify, but this was back 20 years ago. We sold that to Intuit.
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I became VP of Technology for Intuit.
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Then I had a company called Intermute, which is internet security software.
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I did that with my brother Ed English.
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We sold that to Trend Micro.
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I did a company gethuman.
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com, which is served customer service information to over 200 million people.
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Kayak, Moonbeam, the podcast player, Lola, which is the business travel and expense. And did I forget one? I think that's the list.
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And so what's the like thought process?
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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?
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So, like what's your process to come up with these ideas?
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It's mostly scratching my own itch.
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I mean, I could go through company by company.
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The only one that wasn't my original idea was Kayak.
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My co-founder Steve Huffman was one of the founders of Orbitz, and he had observed that Orbitz that 70% of the people that are searching on Orbitz, but then when they were done, they opened a second browser and went directly to united.
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com rather to buy the ticket.
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And so Orbitz did all the searching for people, but never made money.
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And so Steve basically said, "Why don't I 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 a fare."
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And that was his observation.
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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.
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And then I very quickly owned it from a product standpoint.
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I went I might have spent an hour on Expedia that night cuz Expedia was the market leader at that point.
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And just going back the next morning saying, "This isn't going to be hard."
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Cuz I looked at Expedia as bloatware.
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It was sort of seizure-inducing.
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There was so much stuff going on the screen.
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You put a million dollars in.
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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?
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Was that a small bet for you?
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How did you feel at that time?
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Was did that add some anxieties to the process?
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I just sold a company for 30 million, so I could have the the million wasn't that hard for me at that point.
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Although my prior company that I sold was for 30, I blew through my 401k to finance it.
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So, my my first company was tough financially to get it going.
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But for Kayak, I'd made some money, so I could afford to help finance it.
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Why did you Why do you sell your companies?
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Why not, you know, try to run them or have them exist under a management team that you you control for a long time? right?
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Dharmesh has been doing HubSpot for forever.
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Yeah, so Kayak I did for 10 years.
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That was my longest stint.
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And we ended up taking it public 2012, which was incredibly fun.
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And then we sold it shortly thereafter to Priceline, a really booking.
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com, which is the parent company.
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And I just frankly was bored.
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I felt like I was editing the flight screen for 10 years, and I wanted to try something new.
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And I'd had an unbelievably strong team at tech leadership at Kayak.
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So, at that point I felt like I could sneak out without hurting the company cuz I had people that wanted to do UI, they could do product, they could do architecture.
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So, it gave me the freedom to try something new.
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You you're kind of I mean, you're you're kind of like an internet OG a little bit.
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I mean, Kayak's one of the was like a pretty huge thing.
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It still is a huge thing, but in terms of like internet exits, it was it was it was early on in the in the game, and you guys had a nice huge exit.
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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?
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Um you mean across the industry overall?
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Yeah, because like Dharmesh has all these crazy stories where he's like, "You know, I was an early investor in Coinbase, and I and I met the team, and I thought well, he didn't actually tell me this.
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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
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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
6:38
Do you have anything like that?
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Yeah, so I met Brian Chesky at Airbnb when they were financing at a billion-dollar valuation, and I think they're now worth 100 billion or something like that.
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And I remember the time like loving Brian, thought he was iconic and passion-driven, mission-driven.
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But um I didn't see it how big Airbnb was going to get.
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I said, "This seems awesome for people who want to have strangers living in their house, but how many people are going to second to be?"
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So, I kind of missed the bigger picture there.
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Um what was he like when you met him?
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Just like He was very I mean, I I've seen him talk. My wife works there. I totally agree. I think he is an icon.
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I think he's one of the best CEOs out there. He's passion-driven. He's amazing. But what did you see?
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I saw him as very serious and intense. Um he was charismatic.
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He listened well, so we had a good conversation where he wanted me to give him feedback on the company cuz Kayak was a much bigger company at that point.
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And um yeah, I just looked at him as very serious, intense, and charismatic.
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Yeah, whenever you're like you're doing technology for like 15, 20 years, you just get this like crazy story arc or like, you know, um you get to see people and you get you see all these people that you're like, "All right, I think this person's kind of amazing.
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They might go on to do amazing things.
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Maybe it's this idea, maybe it's the next idea."
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Are there any other stories like that of uh that you've seen cuz you've been kind of in the game for such a long time?
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Yeah, so when we financed we Kayak was created in 2004.
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Uh we really launched out of General Catalyst in Cambridge, Mass.
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And then we raised money from Mike Moritz at Sequoia.
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And I remember one day my co-founder and I were working out of Sequoia's office, and Mike Moritz said, "I wanted to introduce you to a couple guys.
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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.
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And I remember meeting those guys at Sequoia's office, and Mike's like, "Yeah, these guys are like putting videos online."
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I'm like, "Yeah, that's cool. Whatever."
8:46
I didn't see that one, either.
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I have I have some famous misses.
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I mean, I've been very lucky as an investor. I think my IRR is 30.
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5% over the last several years, so I've been pretty good.
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I've invested in 60 companies, but I've missed some. I missed Snapchat.
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I met one of their founders when they were financing at an 80 million-dollar valuation.
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That would have been a big outcome.
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Uh Dropbox, I met Drew early on.
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And that wasn't under the guise of me investing in them.
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It was really just networking, but had I I thought Dropbox was going to be plagued by security.
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I'm still kind of shocked. I use Dropbox.
9:22
Do you know that they don't really encrypt your files?
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And that a Dropbox engineer, if they were malicious, they could get at just your files. Yeah, I believe that.
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It's amazing that they're as big as they are.
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And why doesn't anyone worry about that? Yeah.
9:38
What have been What have been the You said you've invested in 60 companies, and you got this great IRR.
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What have been some of your the hits so far?
9:44
Um one of the ones going well right now is pilot. com. I use it.
9:50
And yeah, that's an amazing company.
9:52
I met those guys when they were I was a judge at the MIT 100K competition and they had a company called Ksplice, really exotic technology.
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They could patch a Linux operating system as was running, so you don't have to reboot your servers.
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They sold that to Oracle.
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I was part of, you know, I was the judge at that and I helped them win that competition.
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And then I invested in their next company, Zula, which they ended up selling to um to Dropbox.
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And then when they left Dropbox to create a new company, I basically asked if I could invest before I knew what they were working on.
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So I wrote them a check before I knew what they were doing and that's a 40Xer. I think I financed them.
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I wrote a check as part of the round at $30 million valuation.
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I think their last valuation was like 1. 2 billion or something.
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But that's one that the founding team had the mojo.
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So when you met them, you just knew those guys going to create something serious.
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They They were intense, high energy, they laughed a lot, they finished each other's sentences.
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They just really enjoyed working together.
10:55
Um I also another good return for me at 22X was Kensho, which is a competitor to a Bloomberg terminal.
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And I invested in them because their CTO, Pete Krasco, 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.
11:17
We We had this guy, Trung, work for us.
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So Trung was an analyst at Kensho and Kensho is like this uh you know, they're a startup still but like uh the stereotype to me, from an outsider, they kind of fit this like stereotype of like an uptight financial firm and we found
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Trung working there and this guy, Trung, who works for us, he's like the He's got He's a loudmouth, like literally, like he speaks so loud and he's full of energy and he was a writer for us and we taught him how to, you know, we like encouraged him to use Twitter. Now he's
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Now he's got like, you know, a million followers on Twitter and we and we recruited him from Kensho. That's amazing.
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I like Kensho because of that. Thank you.
12:00
Um and you So Kayak was a big win um and then you did things like, let's say, Moonbeam, which is like, you know, a podcast discovery type of app.
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Could have been big but, you know, maybe I think anything in podcasting is is sort of like looks sort of niche and most of the podcast products, even that win, are sort of like you know, really good lifestyle businesses so far.
12:20
There hasn't been that many big winners in the podcasting space in terms of tools.
12:23
Um are you Do you I know one thing that's hard.
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I've talked to people who who kind of have a an exit like $700 million or $800 million or a billion dollars.
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It's like that becomes the new table stakes for the next thing they do.
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Some go that way and they say, "Okay, I got to get huge now."
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And others are like, "No, I'm literally just going to program things in my house for fun now.
12:42
Like now I I I I don't want to go try to catch lightning in a bottle again."
12:46
Which way uh do you think about it or is there another a third way?
12:51
I always said for each of my companies, it's team first, customer second, product third.
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I said it for Kayak on day one when we put together our culture plan.
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And I really think it's a good way to execute because if you If you focus on becoming a phenomenal recruiter and really becoming a student of recruiting, like read all the books, listen to the podcasts, learn from others that talk about recruiting and recruit an amazing team and then figure out how to lead that team so that there's no stress in the office.
13:20
People work really hard, they have fun, they're cranking stuff out but they're not stressing each other out.
13:25
If you do those things, you can create I always say magical teams create magical products.
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And then usually if you can create a magical product, you can find a profitable business there.
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So for me now, after I sold um Lola, my business travel and expense company, I sold that to Capital One a year ago, I then opened up a venture studio called Boston Venture Studio. It's BVS. net.
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And we have nine apps under development.
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Some of them are in itch to scratch, like fun little things that we put out with source code.
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Um others are swing for the fences, really think it can become big.
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There's a company I launched 2 weeks ago called Deets, like show me the deets.
14:05
That could be a billion-dollar company.
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What we're doing is we're saying online reviews are broken.
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You know, if you go to Google right now and in quotes you search for buy Amazon reviews, you'll see there's 37,000 pages that tell you how to do that.
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If you make, you know, these headphones I'm wearing, if you make a competitor to these and you want to sell it on Amazon, you can easily buy 5,000 five-star reviews for that if you want.
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And these fake review companies are run by PhD computer scientists.
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They are evading Amazon's bot detection, so it's very difficult at this point to detect to detect them.
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They're going through proxy servers, they have aged accounts, they buy products.
14:38
Um and then if you go to Yelp or TripAdvisor, their reviews are largely by people you don't care about.
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You know, like I um looked up a sushi restaurant in New York and I saw five-star reviews of this place.
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People talked about how great it was because it was really cheap.
14:55
And I don't know about you, if you like sushi or not, but I'm not sure I'd be that excited having $10 a person for sushi in New York.
15:01
That's a little scary to me.
15:04
Yeah, you want that catfish and cream cheese roll. Yeah.
15:05
If you go on TripAdvisor and you look for a hotel, you'll see a lot of five-star hotel five-star reviews from Motel 6 and that was great when I was 20 years old.
15:15
I'm not sure I would stay at a Motel 6 now.
15:20
But um a lot of these just don't relate to the person doing the purchase.
15:23
So the idea of Deets is we're going to blow that up and say it's just the recommendations from your friends, from influencers that you choose to follow and then using machine learning doing look-alike modeling to find people that are similar to you.
15:36
Man, it seems like you pick really hard industries.
15:39
Like uh travel is like uh I you know, I'm again, I'm an outsider, you're you're the expert, but it seems like notoriously difficult.
15:46
Like it just seems like incredibly competitive and in very very very challenging and the margins seem small and very hard it seems to start one of those things now.
15:57
Uh podcasting, terribly hard.
15:58
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.
16:12
You know, Yelp has had like Yelp hasn't innovated in in in five or 10 years. Their stock sucks.
16:20
Uh Google Reviews is is a is a horribly challenging person to compete with cuz, you know, they have all these people already using it.
16:26
What What's the game What's the game plan here and why are you picking the hardest things to work on?
16:35
Um Yeah, the origin of Deets is I I'm friends with some people who own restaurants in Boston and I saw the difficulty they had during COVID and so it really developed some compassion for restaurant owners.
16:47
And they all told me how much they hate Yelp.
16:49
Yelp is just like mafia where you pay if you they call you and they say you have a lot of bad reviews, pay us some pay us hundreds of dollars a month and we'll sort of clean up your site on Yelp.
16:57
It's kind of like in Italy, there's a movie called Billion Dollar Bully about Yelp.
17:03
It came out in 2019 and the opening scene is an Italian chef who said when he opened his first restaurant in Italy, someone broke the windows, he fixed them, they broke them again the next week, he fixed them, the next week some guy comes in and says, "I noticed someone keeps breaking the windows.
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If you pay me $100 a week, I'll make sure no one breaks the windows anymore."
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And he knew that was the guy who was breaking his windows.
17:23
He's like Yelp is just like that.
17:24
So I look at Yelp as a 20-year-old dinosaur.
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That's the last 20 years, we want to be the next 20 years.
17:30
And I look at the evolution, you know, the world is different now than it was when Yelp was created.
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For one, the rise of the influencers, particularly Gen Z.
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They make all their purchase decisions based on influencers and that's true now for dining.
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So we want to give it make it really easy.
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Rather than scrolling through Instagram and trying to find an old post of a restaurant you saw a month ago, having it in one tight, really clean UI.
17:56
It's your friends, it's your influencers.
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And then on machine learning, I'm really inspired by TikTok. TikTok's an amazing app.
18:02
They don't ask you any questions, they don't say, you know, what are you What's your interest?
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But if you look at my TikTok feed, there's a lot of bass players.
18:09
I'm a bad bass player but I like bass players. There's a lot of dogs. I have a new dog. Um there's gardening.
18:15
TikTok has figured out the stuff I'm interested in and without ever asking me a question.
18:21
And the way they work is they don't even ask you who your friends are.
18:23
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.
18:33
So I really like that look-alike modeling or user clustering.
18:35
So we're doing that with Deets as well.
18:37
We're going to find your friends, the influencers you like, and then people of the same taste as you.
18:46
This data is wrong every freaking time.
18:49
Have you heard of HubSpot?
18:51
HubSpot is a CRM platform where everything is fully integrated.
18:52
Woah, I can see the client's whole history, calls, support tickets, emails, and here's a task from 3 days ago I totally missed. HubSpot, grow better.
19:05
Do you think that starting a company now that you're wealthy is easier or harder than when you were just getting going in your career?
19:12
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.
19:18
If you talk to anyone who works with me, they'll say I'm working as hard now as I was during my first company when I was blowing through my 401k to finance it.
19:27
Um To me, work hard is recruit hard.
19:31
Lead, coach people, get people excited.
19:34
And I'm working on that as hard as I ever have.
19:36
I'm trying to get a little bit better with each company.
19:37
There is some advantage having money that if you see a stupid problem that costs five grand to fix, you know, when you create in your first company, you don't have that five grand.
19:49
Now you do, so you just pay a little money and problems go away. What do you think, Sean? Easier or harder?
19:56
Uh yeah, I think it's different and you just have to like work with this the pros and the cons, right?
19:59
Like, yeah, recruiting is easier and you waste less time on the on just like the rookie mistakes that you always make, but then you know, there is some diminishment maybe of the edge or um you know, the things that made you successful the first time might have been that there was a technology wave going on, there was a bunch of opportunity and like you have to recognize new technology waves or new inflection points, new things that have changed.
20:23
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 a make the user experience way different.
20:33
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.
20:41
Um you know, I can create a delightful user experience whereas before, you know, maybe I couldn't.
20:44
So, I think Yeah, I think it's different and the things he's saying make a lot of sense to me.
20:49
I want to tell you one thing about doing tech now versus 20 years ago.
20:52
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.
20:58
They just couldn't get the tech working.
21:01
That's hardly the case now.
21:01
Like, the stack, the AWS, the tools, the open source um it's pretty easy to assemble the right libraries and right people to help put something together.
21:15
Companies fail today for one of two reasons.
21:19
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.
21:28
They they fail the culture code.
21:30
Or number two, they built a nice product, but it's a real problem that no one cares about.
21:37
And unfortunately a lot of founders have an itch to scratch as you were saying earlier, Sam.
21:42
And they get really obsessed about it.
21:44
Like, I have this little problem I'm going to work on it for 10 years and they don't realize that not a lot of people have that same problem.
21:52
It makes me sad when I see that.
21:52
When I see a beautiful product that solves a problem I don't care about.
21:58
Yeah, you see that all the time.
21:58
That's like the number one cause of death, I think with uh with startups.
22:02
You you said something a second ago I wanted to to ask you about.
22:06
So, you go become amazing at recruiting.
22:08
I um that's never been something that I was like, that's the thing I'm going to set my mind to.
22:14
And you said, you know, I read all the books, I read all I listened to all the podcasts and try to become amazing at this so I can assemble teams to to you know, do your venture studio.
22:24
And um You're pretty good at it though, Sean.
22:27
Well, I'm just like, I don't know. You never know, right?
22:29
Like, even uh whatever, you know, like it's like a belt system.
22:32
It's like even if I'm a blue belt, there's still a black belt, you know, that I could go learn from.
22:36
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.
22:40
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 80/20, the the summary of what principles you think are most important when it comes to recruiting and what are there any that you wouldn't expect?
23:01
Are they all just things that's like I want to lose weight.
23:05
It's like, eat healthy and exercise.
23:06
Like, okay, well, you know, I guess that's true, but it's not that not that helpful.
23:09
I kind of already do that.
23:10
Are there any things that are maybe counterintuitive or uh or nuanced that that are important?
23:16
The main thing is just recruit all the time.
23:18
Always always be recruiting and always be trying to connect with people.
23:22
And you might be going to a you know, a coffee social to learn about why crypto's terrible or whatever.
23:31
Um and you don't realize there's someone going to be there that would be your next unbelievable CMO.
23:34
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.
23:45
Um I have a little bit of an off-color story, which I probably shouldn't tell, but um someone asked me once about my recruiting strategy.
23:51
By the way, that's the best starting of a story. So, go ahead.
23:55
I mean I mean I like perked up.
23:58
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.
24:05
I'll come meet you at a Starbucks near you.
24:07
I'll do whatever it takes to get you to meet my team.
24:09
I train my team how they should um behave in their first meeting with you and all that.
24:14
And the first thing that came to mind when someone asked me about this about why I'm so laser-focused on getting these people is one time I was in 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.
24:31
My friend said, English, don't even think about it.
24:34
She's dating the captain of the football team.
24:36
So, at that moment that girl went in color and the rest of my world was black and white.
24:40
Like, I had to date that girl just cuz my friend said I couldn't.
24:42
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?
24:52
I did this a funny Japanese game show that is a guy in Italy looking for the most beautiful woman in the world.
24:59
And when he encounters the first beautiful woman in Italy, he says to her, do you know anyone even more beautiful than you?
25:03
And that leads us kind of a hilarious uh succession of conversations, but when I'm recruiting and I find someone amazing, I'll just do whatever it takes to get them excited and to get them to meet my team.
25:13
And I've always said that the first five people hire the next 50 who hire the next 500.
25:20
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.
25:29
When they meet those five, they'll say, oh my god, I need to work with this team.
25:33
You kind of have I'm I'm clicking around on your site.
25:35
You you and Dharmesh are interesting to me because you guys have this like dry kind of almost nerdy sense of humor that I love.
25:46
So, for example, if you go to lola.
25:46
com, it it basically says the domain's for sale, but you can see the history of Lola by clicking here and it goes to uh pmdpme, that's you.
25:55
org and it's a website where it's like plain text, you're just explaining exactly what happens.
26:00
And so, that's kind of a an interesting way of like going about uh explaining the the the story.
26:07
But, if you click paulenglish.
26:09
com, it goes to your website and it talks about some of your cool investments and your your founder stories and things like that.
26:14
And then it says like all the clubs you're involved in.
26:18
And one of them it looks like either you started or you are part of the bipolar social club.
26:22
I was reading on your Wikipedia, it talked about like, you know, you had some issues with bipolar.
26:27
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?
26:33
Uh I I like I like guys like you and Dharmesh.
26:37
It's why I love Dharmesh 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 and then you start talking to him a little more and it's like, oh, you might be like quiet, but you like you're kind of a killer and you're incredibly quirky.
26:49
For example, he's got a new project called vendiagram.
26:51
com where it's a community for people who love Venn diagrams.
26:57
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.
27:07
And he just has all these things.
27:09
You kind of seem like that.
27:11
Are you a guy who's just constantly tinkering on on on stuff?
27:16
Yeah, I mean, I have um I own about 300 domain names and every domain name has a Google Doc associated with the idea for the company.
27:25
Um I'm obsessed with brand and names and I'm and Dharmesh and I share this that we're prepared prepared to spend big money to buy a good name.
27:33
And um I do I do a I have lectured a lot of universities and I give a lecture on where creativity comes from.
27:41
And I've done this every day where from Berkeley School of Music, Dartmouth Film School, Rhode Island School of Design, as well as the more traditional universities you'd think about.
27:51
And what I do is let's say I'm teaching Thursday at 5:00.
27:53
At Wednesday at 5:00, I'll have the professor email the students and say, take a picture of something tonight that annoys you.
28:00
Not a picture you took yesterday, not a picture you found on Google, but take a picture of something tonight which annoys you.
28:06
And then I teach the students about how irritation becomes inspiration and how any problem can become the motivation for a product.
28:14
And we go through a very specific exercise about how to do that.
28:18
And I am someone who loves ideating.
28:20
If you look at they say that you're the average of the five people you spend most of your time with.
28:26
If you want to change your life, change the people you spend time with.
28:27
If you look at people who I hang out with, they care about nonprofit work, philosophy, and ideating. Like, improving things.
28:33
I just have a blast meeting with people like Dharmesh and saying, how could we fix this?
28:39
How could we do this better?
28:41
Well, you're in the right spot.
28:41
So, we start when we started this podcast, it was it was doing all right.
28:46
Maybe, I don't know, 10,000 people would listen to every episode.
28:50
So, maybe like, I don't know, 100,000 in in a month, something like that.
28:54
And um it was a classic interview show.
28:56
Similar to what we kind of have done so far up till now with getting to know you a little bit.
29:01
Where it's like, oh, oh, you built Kayak. Amazing. Tell me about it.
29:04
You know, how'd you do it?
29:04
And uh it was just like every other tech or business podcast, which is a how'd you do it podcast.
29:09
And then one day uh just to mix it up, I was like I invited Sam on.
29:14
I was like, Sam, let's just shoot the like we do when we're not on a podcast about like, oh, have you seen this?
29:21
Yo, why doesn't somebody solve this?
29:22
Dude, I tried to book this the other day, it was so annoying.
29:24
And we just started brainstorming.
29:26
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 would be like, you know, million-dollar, billion-dollar ideas.
29:37
And um and so we started that's what we and then the whole podcast took off.
29:40
And so, now it's like in the top ranks of the charts and all this stuff.
29:44
And it's I think because we switched into this like idea and brainstorm mode, Yeah.
29:48
and there's a lot of people like us that are out there.
29:51
The same way Dharmesh is trying to find all the Venn diagrammers out there, all the Venners, we're trying to find all the people that love to shoot the and brainstorm ideas.
30:00
Sounds like you're one of them.
30:00
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 for some ideas that you'll probably never have time to go do? Sure.
30:13
Um I'll tell you some ones that the itch was enough that I actually did a little bit of work on it.
30:21
So, one of them was I live in Boston, but I also spend a lot of time in New York, where I am today.
30:27
And where I live is kind of between West Village and Tribeca, near Soho, and I don't know New York that well.
30:34
Like, I know the those three neighborhoods, but I don't really know like Upper East Side, Upper West Side, whatever.
30:39
If I'm trying to meet someone on the Upper West Side, I don't know where to meet.
30:44
I'm like, this is annoying that there isn't a website where they can see if they where they are, where I am, and pick a bar in the middle. So, I built an app. It's called middle. net.
30:55
I mean, I bought that domain name. And middle.
30:59
net allows you to have two people or three or four, as many as you want.
31:03
It grabs your locations from the browser, and it shows you like a coffee shop or bar to meet in the middle.
31:09
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 cuz I was getting used to the city.
31:16
I couldn't find a way to do it, so I built an app.
31:20
Um Another one, when you meet someone, so I generally don't really like going to conferences cuz I'm a little bit shy, a little introverted.
31:28
I've like learned how to be extroverted, and I can say more about that if you care to hear about it.
31:32
But, when you do go to a conference and you meet someone and you want to swap info, it's annoying to do it.
31:39
You know, you got to type in phone numbers and stuff.
31:42
Got to type in email addresses. So dumb.
31:45
Or you can use this dot card thing, but if you carry this card around this card around, so I designed a little app called funcontact. It's funcontact.
31:52
com, and it allows you to have a set a a list of QR codes.
31:57
One QR code might be just my email.
32:00
Another one might be my email, my home address.
32:02
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 book.
32:09
Um I built that cuz I needed it.
32:11
I don't think it'll ever become a company, but I just wanted that, so I built it.
32:15
How many people are using this? This looks cool. I'll use it.
32:19
I would I just needed one of those things the other day. It's super cool. Um I use it last night.
32:24
Oh, do you want to hear a funny story? Yeah.
32:28
So, last night was my 3-year anniversary with my girlfriend Rachel, and we went to San Ambroise in West Village for our our first date 3 years ago.
32:38
And next to us was Anne Wintour.
32:38
I don't you know who she is, the editor of Vogue magazine, one of the top socialites in New York.
32:43
And Bradley Cooper on our first date just sat next to us.
32:47
Last night was our 3-year anniversary.
32:48
We go to the same restaurant.
32:49
Guess who's sitting next to us? Anna Wintour. That was super cool.
32:53
But, at the end of the meeting, I I did talk to her for a couple minutes, and then she left.
32:56
And then the table on the other side of me was four people working in the fashion industry, where my girlfriend works.
33:04
And we really kind of bonded, talked about it.
33:07
I talked about the Bipolar Social Club, the clothing brand I want to create.
33:11
And then they asked for my number, and I just pulled out funcontact, and I scanned it.
33:14
Now all these young fashion people have my number, and we've been messaging each other today about Bipolar Social Club. That's great.
33:24
What's the clothing brand you want to create?
33:27
So, bipolar I have bipolar illness.
33:27
I was diagnosed at age 25, and it's a pretty serious illness.
33:32
You know, a lot of people end up killing themselves or ruining their marriage or their job or their lives.
33:41
And it took me a good 10 or 15 years to learn how to manage it for myself.
33:46
There's bipolar one and bipolar two.
33:46
I'm bipolar two, so I'm not the most severe type.
33:49
The most severe type has voices and end up homeless and and or worse.
33:55
Um not that there's a lot of things worse than being homeless, but bipolar one is pretty serious illness.
34:01
Bipolar two still has problems, but over the years I learned how to deal with it.
34:05
And I want to be able to laugh with other people bipolar about the funny things about being bipolar.
34:12
So, I created this video series.
34:12
If you go to bipolarsocialclub.
34:14
org, there's 10 people with bipolar illness who kind of tell their journey.
34:20
And it's kind of de-stigmatizing 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."
34:28
And I have this thing about bipolar people that if I'm in a cocktail party with 100 people and there's someone like on the other side of the room, I can tell they're bipolar.
34:35
Like, we recognize each other.
34:39
My gay friends say they have gaydar.
34:41
They can tell gay people across the room.
34:43
I can tell bipolar people across the room.
34:45
And we're trying to do something fun.
34:46
So, we want to have a clothing brand where bipolar people kind of wear the brand and proud of like bipolar and proud. So, bipolar social club.
34:54
We wanted just sort of a fun name.
34:57
Is there anything in uh in the travel industry that you noticed uh I mean, because you had more data than, you know, there's probably only hundreds of people in the world or maybe low digit thousands that are able to kind of see some of the things that you saw because of the scale of Kayak and and the company that bought you guys?
35:15
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?
35:20
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.
35:31
The stuff they do to you it gives you a false sense of security, but there's no real security with TSA. Um that's irritating.
35:40
I wish someone would solve that and make something a lot more efficient and uh safer.
35:49
Airlines are running on old technology.
35:51
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.
35:58
So, it's very archaic and old, and um I had said earlier that I travel between Boston and New York.
36:05
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 faster to drive.
36:15
So, as far as things in the in the travel industry I would like to see fixed, I'd like to see someone that figured out how to work with all the unions who put all these requirements in, who work in the airlines, how to work with TSA, how to make flying pleasurable.
36:31
It's not pleasurable now.
36:31
I also remember growing up when you go to the airport, people used to dress up.
36:36
They were like really excited to get on a plane to travel.
36:39
But now, airports are just a nightmare, and I wish someone could make airports pleasant and make flying pleasant. Yeah, same.
36:46
It sounds like a the hardest thing on Earth to do, though.
36:50
What do you think about what Elon's doing?
36:51
Uh so, Elon buys Twitter.
36:51
He's kind of taking this like uh you know, technology first thing, trying to change the culture overnight, force people back in the office, lay off a bunch of people, trying to ship changes really fast.
37:03
Seems a little bit helter-skelter. Have you followed that?
37:05
And I'm curious, what's your opinion as a CTO and somebody's done tech for a long time?
37:09
I followed it quite closely, and put me in the list of a thousand people who want to create a Twitter competitor right now.
37:16
I've been spending a bunch of time in the last week ruminating on that.
37:21
And I think it's a bit of a show.
37:21
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.
37:35
I'm a happy Tesla stock holder from 2016.
37:40
Um but when I looked at the way he fired people at at Twitter, it was just obnoxious as Like, do you really need You are the richest guy in the room in the world.
37:48
Do you really need to also be an There was no reason he had to march people out of the office.
37:53
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 where 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."
38:06
Uh I'm not very happy about that.
38:09
So, I'm either going to Do you think he's going to pull it off? He does stupid things.
38:14
Like, the dog verification, that was a joke.
38:17
Um but if he assembles smart people around him, it it looks like the smartest people all have left Twitter already.
38:25
They've all run for the hills.
38:28
But, he's going to hire some new people in.
38:29
I'm sure there's some good people that are still there.
38:32
I'm sure he'll do some interesting things with it, but I'm really looking forward to all the Twitter replacements that are going to come out.
38:38
It's hard to compete with an entrenched com- company that has hundreds of millions of users, because even if the product is better, does Stephen King really want to tweet on samparr.
38:46
com where there'll be, you know, a thousand followers as opposed to Twitter where they'll have a million followers? But, I don't know.
38:56
I think he stirs stuff up, and I want to see the innovation that comes out. That's cool.
38:59
Um yeah, I I think that there's a I think if somebody's going to do it, they're going to have to come up with a uh a social innovation, not a uh it's not a technol- it's not a technical innovation.
39:15
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.
39:23
So, like for example, you know, uh Facebook was this privacy policy change where it was like, "Instead of MySpace, um this is only people that go to your school."
39:35
And at the door, we gate you with your your school email address.
39:39
It's a change in privacy policy that totally changed people's behavior cuz now you're more interested in everybody and you're more willing to share.
39:46
Then as Facebook became the norm, then it became you know, things like Twitter which was like change your privacy policy.
39:52
I don't have to accept your friend request for you to see my content.
39:55
It's like you could just follow me.
39:56
Unilaterally you could just describe you could decide to get my content.
39:58
That was totally different than Facebook.
40:01
Then Snapchat comes out and it's like here's the privacy policy here.
40:02
All the self-destructs in 24 hours or right like in 10 seconds whatever.
40:07
So content is not permanent here.
40:09
And so people flock to that.
40:10
And so there's just this ongoing shift of like what is the like the social rule set that we're going to follow on this thing.
40:18
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.
40:25
You got to 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.
40:38
And then the other one is I think if you created you have to turn the disadvantage into an advantage.
40:43
So instead of Stephen King saying why do I want to go tweet here when there's only I'm only going to have 1,000 followers over here, you have to make it where it's now benefit like the perk is that there's only 1,000 people there.
40:54
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.
41:12
Uh if it's Yeah, I think the decentralized is a joke.
41:14
Um I think that's technology looking for a solution.
41:19
I think Truth Social was an epic failure.
41:23
Um the things that I care about on Twitter right now is I'm bothered by all the trolls and the cruelty.
41:30
And um you know, I look at TikTok and I don't watch TV really, but I use TikTok probably 20 minutes a day.
41:40
And I like how positive TikTok is.
41:40
Now 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.
41:47
Like the average 18-year-old is like kinder than the 18-year-old you know.
41:54
Do you think that's true? I 100% think it's true.
41:56
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.
42:02
Twitter I mean TikTok is amazing.
42:05
Someone will post a video of themself 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.
42:23
It's so different than Twitter.
42:25
And so what I want to do as a Twitter competitor is create the kind Twitter where there's no trolls, there's no cruelty and then also deal with the misinformation.
42:32
When you see a tweet that says COVID vaccine causes autism, like how do you smack that down?
42:39
And I'm very interested in those two problems, getting rid of the cruelty and flagging misinformation, but doing it without filtering out independent info.
42:49
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.
42:57
And maybe even the US if you're um there's certain personal problems.
43:02
Like some people might not want to say they're bipolar because maybe that will hurt their career.
43:08
Um but I think this I think this there is a way to build something like Twitter that is kind and truth-oriented.
43:14
And I've been spending a lot of time in the last two weeks brainstorming with some other people also thinking about doing something new.
43:23
And I'm confident that there will be something new.
43:24
Whether it's something that I help people with or something completely independent, I don't know, but someone needs to create something better.
43:30
Paul, we um I'm going to ask you one last question before we have to move on to the next segment segment, but uh what's your domain portfolio worth right now you think? So I have 300.
43:42
Let's say it cost me $10 each a year.
43:47
So I'm spending 3,000 a year in domain fees.
43:50
I paid hundreds of thousands of dollars to buy domains.
43:55
I don't sell them that often because I still hold on to the idea that caused you to buy the domains so most I hold on.
44:00
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.
44:07
I have some that are worth $100,000 or more and I have some that are just funny probably just to me.
44:14
So I'm not sure what the price is on that.
44:17
Lola would be mid six figures I'd imagine, right?
44:20
Lola we paid 500,000 to buy Lola.
44:20
We were in a bidding war.
44:24
It's It's up for sale again. I would for sale.
44:26
Yeah, cuz we sold the company to Capital One.
44:28
They want everything to be Capital One.
44:30
They didn't want the name Lola. So the name is for sale. Perfect. Buy it back. Possibly. Uh okay. Um amazing.
44:40
And uh where should people go find you? I'm on your website.
44:45
I think your website's pretty cool.
44:46
You have like here's how I manage my time.
44:47
Here's how I run meetings.
44:49
I love when people do that when they put their like operating playbooks out there.
44:54
Um is that the best place to follow you or should Twitter Yeah, I talk about meditation.
44:57
I talk about getting rid of pain and suffering.
44:59
I talk about getting rid of anger from your life.
45:01
It's just my name paulenglish. com. Awesome.
45:05
Well Paul, thanks for coming on. Appreciate it.
45:08
Yeah, we appreciate you doing this.
45:08
Um and uh I'm I'm I'm on your bipolar social club.
45:12
I don't think I have bipolar, but I still think it's fun to follow along this site.
45:16
So thanks for doing this.
45:19
And we appreciate you coming. Thanks a lot, guys.