00:00
I think a lot of people say it's harder because you don't have the edge. You don't work as hard. That's not true with me. If you talk to anyone who works with me, they'll say I'm working as hard now as I was during my first company when I was blowing through my four zero one k to finance it.
00:19
Alright, Paul. What's going on, man? Will you, Dharmesh,
00:23
CTO
00:24
co founder HubSpot told us we have to we have to we don't we don't have to, but we should talk to you.
00:30
What, why did he say that? I don't know. It's gonna be connected.
00:35
Damesh and I
00:37
have a lot of,
00:39
fun talking together about technology, philosophy, and teams,
00:44
One fun thing that Demesh and I did going back many years ago now when I was CTO,
00:49
a founder of kayak,
00:51
Dimesh and I kinda switched jobs for a day. So I actually had him made up. I got him an email address. Dharmesh at kayak dot com and made up business cards And he basically sat at my desk at Kai for day, and then I sat at HubSpot for day.
01:04
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.
01:14
And your big hit has been, well, so far, you have a new company Lola, which I don't know if you know this or not. You guys advertise with my old company to hustle a bit. So Yep.
01:25
We worked with you a bit, but,
01:27
your big hit so far has been kayak. Right? What did you sell that for? Like, two or three billion? Two billion. I've actually sold six companies in a row, including Lola. I've sold even another one after Lola Moonbeam, which is a podcast app. And now I'm on to my seventh company.
01:42
Which one of the so which of the six has been the most financially successful for you? Cog was the biggest financial outcome
01:51
which I'm deeply appreciative.
01:53
And I learned a lot at Cogn, some amazing people.
01:56
But there's other things which are also really significant that aren't just monetary.
02:02
So my first sale,
02:04
I don't have to I just told you I sold six in a row. There's another one that I don't really count. As it only was a company I created in high school, but it's very meaningful to me, make money in high school designing software.
02:16
And what were the six? So I had a company called Boston Light. We were an e commerce company. We let people set up storefronts a little bit like Shopify. I just was back twenty years ago, we sold that to Intuit, had again VP technology different to it. Then I had a company called Intimute, which is internet security software. I did that with my brother, Ed English, We sold that to Trend Micro. I did a company gethuman dot com, which is serve customer service information to have a two hundred million people,
02:42
kayak,
02:43
Moonbeam, the podcast player, Lola, which is the business travel and expense.
02:48
And did I forget one? I think that's a list.
02:52
And so what's the, like,
02:54
dot process? So would did you start them all in kind of the same
02:59
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 a company by company. The only one that wasn't
03:11
my original idea was Carriac.
03:13
My co founder, Steve Haffner, was one of the founders of orbits, and he had observed at orbits that seventy percent of the people had to search on orbits, but then when they were done, they opened second browser and went directly to United dot com, rebooted by the ticket. And so orbitz did all the searching for people, but never made money. And so Steve basically said, why don't we create a company where all we do is search. And then if someone wants to go united, they click the link and we'll send them directly to United and they could buy a fair. And that was his observation. We met by chance,
03:41
and within probably forty five minutes decided to sign up as co founders,
03:45
each put a million dollars into the,
03:47
original round of financing.
03:50
And then I very quickly owned it from a product standpoint.
03:53
I went, I'm about to spend an hour on Expedia that night,
03:57
because Expedia was the market leader at that point. And just going back the next morning saying this isn't gonna be hard because I looked at Expedia as bloatware. It was sort of seizure inducing. There was so much stuff going on on the screen. You put a million dollars in. Was that, like, a I'm put I'm going all my chips on the table right now, or was that a, you know, was that half your net worth? Was that a small bet for you? How did you feel at that time? Was did that add some anxieties to the process. I just sold a company for thirty million. So I could've the the million wasn't that hard for me. At that point. Oh, my prior company that I sold for thirty,
04:31
I blew through my four zero one k to finance it. So my my first company was tough financially.
04:38
To get it going. But for Kai, I could have made some money. So I could afford to,
04:42
help finance it. Why did you why do you sell your companies? Why not you know, try to run them or have them exist on your management team that you you control for a long time. Like, Dermesh. Right? Dermesh has been doing HubSpot for forever. Yeah. So kayak I did for ten years. That was my longest stint.
04:59
And we ended up taking it public two thousand twelve, which is incredibly fun. And then we sold it shortly thereafter. The price on a really booking dot com, which is the parent company.
05:09
And I just frankly was bored. I felt like I was editing the flight screen for ten years. And I want to try something new. And I had had an unbelievably
05:17
strong team
05:19
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.
05:30
So it gave me the freedom to try something new. You you're kind of I mean, you're you're kinda like an internet o g a little bit. I mean KIAx, one of the was like a pretty huge thing. It still is a huge thing, but in terms of, like, internet exits, it was, it was, it was early on in the game, and you guys had a nice huge exit.
05:47
Who are some of the people who are kinda like big shots and ballers now
05:52
that you got to know a little bit earlier on?
05:57
You need to cross the industry
05:59
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 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 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 and I mean, he just has met or I believe he was an early investor in Dropbox as well. And, like, he probably has all these interesting stories
06:26
about some of these folks who are now, like tycoons are big deal now. But he was fortunate because he's a little bit older and was more successful than they were when they were just getting their things started, that he got insight into these businesses. Do you have anything like that? Yeah. So I met Brian Chesky at Airbnb when they were financing in a billion dollar evaluation,
06:46
and I think the net worth a hundred billion or something like that.
06:49
And I remember the time, like, loving Brian thought he was
06:53
iconic,
06:55
and passion driven
06:58
mission driven,
06:59
but,
07:01
I didn't see it how big Abby was gonna get. I said this seems
07:06
awesome for people one of Strange's little in the house, but how many people look at that gonna be? So I kinda missed the bigger picture there.
07:14
What was he like when you met him? Just get, like, I mean,
07:18
I've seen him talk. My wife works there. I totally agree. I he is an icon. I think he's one of the best CEOs out there. He's passion driven. He's amazing.
07:26
But what did you see? I saw him as very serious and intense
07:33
He was charismatic he listened well. So we had a good conversation
07:37
where he wanted me to give him feedback on the company because Cox was bigger company at that point.
07:42
And,
07:43
yeah, I just looked at him as very serious, intense,
07:47
and charismatic.
07:48
Yeah. Whenever you're, like, you're doing technology for, like, fifteen, twenty years,
07:52
you just get this, like, crazy story arc or, like, you know,
07:56
you get to see people You can you see all these people that you're like, alright. I think this person's kind of amazing. They might go on to do amazing things. Maybe it's this idea. Maybe it's the next idea. Are there any other stories like that of, that you've seen because you've been kinda in the game for such a long time?
08:11
Yeah. So when we financed
08:13
We had conquest made in two thousand and four.
08:16
We've really launched out a general catalyst in Cambridge Mass,
08:20
And then we raised money from Mike Morris Takoya.
08:24
And I remember one day, my cofounder and I were working out of a school or office
08:28
And Mike Moore had said, oh, I wanted to use it a couple guys.
08:32
This is Chad Hurley, and I've got his cofounder, but they were the founders of YouTube.
08:37
Deepgram. I think Yeah. That's right. And I remember meeting those guys at the store office. And Mike's like, yeah, these guys are like putting videos online. I'm like, yeah, that's cool. Whatever.
08:46
I didn't see that one either.
08:48
I have I have some famous misses.
08:51
I mean, I've been very lucky as an investor.
08:54
I think my eye are is thirty point five percent over the last several years. So I've been pretty good. I've invested in sixty companies.
09:01
But I've missed some. I missed Snapchat. I met one of their founders when they were financing at an eighty million dollar evaluation.
09:08
That would have been a big outcome.
09:11
Dropbox summit, Drew, early on.
09:14
And that wasn't under the guise of me investing in Emma. It was really just networking, but had I
09:19
I thought Dropbox gonna be played by security. I'm still kinda shocked. I use Dropbox.
09:24
Do you know that they don't really encrypt your files?
09:27
And that a Dropbox engineer, if they're malicious to get at just your files.
09:32
Yeah. I believe that. It's amazing that they're as big as they are. And why doesn't anyone
09:37
worry about that. Yeah. What have been what have been the, you said you've invested in sixty companies and you got this great IR, what have been some of your the hits so far?
09:46
One of the ones coming up right now is pilot dot com.
09:49
I use an
09:50
yeah. That's an amazing company.
09:53
I met those guys
09:54
when they were I was a judge at the MIT hundred k competition and had a company called Case Place
10:00
really exotic technology. They could
10:03
patch a Linux operating system as was running. So you don't have to reboot your servers.
10:08
They sold that to Oracle.
10:10
I was part of, you know, I was the judge at that and I helped them win that competition.
10:14
And then I invested in the next company, Zulu, which ended up selling to
10:21
to Dropbox.
10:22
And then when they left Dropbox, create another company, I basically asked if I could invest before I knew what they're working on. So I wrote them a check before I knew what they were doing, and that's a forty x, sir.
10:33
I think I financed them. I wrote a check as part of the rounded thirty million dollar evaluation. I think their last evaluation was like one point two billion or something. But that's one that the founding team had the mojo. So when you met them, you just knew those guys gonna create something serious. They they were intense, high energy. They laughed a lot. They finished each other's sentences. They just really enjoyed working together.
10:57
I also another good return for me at twenty two x was
11:02
Ken Show, which is a competitor to a Bloomberg terminal.
11:06
And I invested in them because their CCT Cresco
11:09
used to work at kayak, and I knew him from kayak. And I just knew he was tested to do great things. And he that was a really nice exit.
11:17
We we had this guy, Trung worked for us. So Trung was an analyst at Ken Show.
11:23
And kensho is like this, you know, they're a startup still, but, like, the stereotype,
11:29
to me, from an outsider, they've kinda fit this, like, stereotype of, like, an uptight financial firm. And we found Trung working there, and
11:38
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.
11:46
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 and we recruited him from Ken show. That's amazing.
11:56
I like Kensho because of that. Thank you.
12:00
And you so kayak was a big win.
12:03
And then you did things like, let's say Moonbeam, which is like, you know, a podcast discovery type of app. Could have been big, but, you know, maybe I think anything in podcasting is is sort of like looks sort of niche and most of the podcast
12:15
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.
12:26
Are you do you
12:28
I know one thing that's hard off people who kinda have an exit, like, seven hundred million or eight hundred million or a billion dollars. It's like, that becomes the new table stakes for the next thing they do. Some go that way, and they say, okay, I gotta get huge now. And others are like, no. I'm literally just gonna program things in my house for fun now. Like, now I I I don't wanna go try to catch lightning in all again. Which way,
12:48
do you think about it, or is there another a third way?
12:51
I've always said for each of my companies, it's team first customer second profit third.
12:56
I set it for kayak on day one when we put together our culture plan.
13:01
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,
13:13
learn from others that talk about recruiting,
13:15
and recruit an amazing team and then figure out how to lead that team so that there's no stress in the office. People work really hard. They have fun,
13:22
that cranking stuff out, but they're not stressing each other out. If you do those things,
13:28
you can create I always say magic teams create magical products.
13:32
And then usually if you can create a magical product, you can find a profitable business there. So for me now, after I sold,
13:40
Lola,
13:41
My business travel and expense company, I sold that to Capital One a year ago. I then opened up a venture studio called Boston Venture Studio. It's b v s dot net. And we have nine apps under development. Some of them are in each to scratch, like fun little things that we put out with source code.
13:57
Others our swing for defense is really thinking it's become big. There's a company I launched two weeks ago called Deats, like, show me the Deats.
14:05
That could be a billion dollar company. What we're doing is you're saying online reviews are broken.
14:11
You know, if you go to Google right now in quotes, you search for Amazon reviews, you'll see this thirty seven thousand pages that tell you how to do that.
14:19
If you make, you know, these headphones I'm wearing, if you make a competitor of these and you wanna sell it on Amazon, can easily buy a thousand five star views for that if you want. And these pay review companies are run by PhD computer scientists. They're evading Amazon's bot detection. So it's very difficult at this point to have to detect them. They're going through proxy servers. They have age accounts, they buy products.
14:40
And then if you go to Yelp or TripAdvisor,
14:43
The reviews are largely by people you don't care about.
14:46
You know, like, I,
14:48
looked up a sushi restaurant in New York, And I saw five sour reviews of this place. People talked about how great it was because it's really cheap.
14:55
And I don't know about you, if you like sushi or not, but I'm not sure if you'd be that excited having ten dollars a person, but sushi in New York, that's a little scary to me. Yeah. You want that catfish and cream cheese roll.
15:07
Yeah. If you go on, you're the TripAdvisor
15:10
and you look for hotel, you'll see a lot of five star hotel, five star reviews from hotel six. And was great when I was twenty years old. I'm not sure I would say the motel six now,
15:20
but, a lot of you just don't relate to
15:23
the person doing the purchase. So the idea of dates are gonna 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 book a like modeling to find people that are similar to you. Man, it seems like you pick really hard industries. Like,
15:41
travel is like,
15:43
you know, I'm, again, I'm an outsider. You're you're the expert, but it seems like notoriously difficult. Like, it just seems like incredibly
15:50
competitive
15:51
and in very, very, very challenging, and the margins seem small,
15:54
very hard. It seems to start one of those things now.
15:58
Podcasting
15:59
terribly hard. I don't, you know, I don't entirely understand why it's so hard, but, like, the nothing has entirely clicked to make it this this fantastic industry,
16:08
even though a lot of people use podcasts. And then reviews also seem terribly challenging. You know, Yelp has had like Yelp hasn't innovated in in in five or ten years. Their stock sucks.
16:20
Google reviews is is a is a horribly challenging person to compete with because, you know, they have all these people already using it. What what's the game? What's the game plan here? And why are you picking the hardest things to work on?
16:37
Yeah. The origin of Deats is I I'm friends with some people who own restaurants in Boston.
16:42
And I saw the difference that 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,
16:52
where you pay if you they call you and they save a lot of bad reviews, call us and pass hundreds of dollars a month. It will sort of clean up your
16:59
site on Yelp. It's kinda like in Italy.
17:02
There's a movie called billion dollar bully
17:05
about Yale that came out in twenty nineteen, and the opening scene is an Italian chef who said when he opened his first restaurant, Italy, someone broke the windows, he fixed them. They broke move in the next week. He fixed them. The next week, some guy comes in and says, I noticed someone keeps breaking the windows. You pay me a hundred dollars a week, I'll make sure no bricks or windows anymore. And he knew that was the guy who's breaking his windows. He's like, yelp was just like that. So I look at yelp as a twenty year old dinosaur.
17:29
That's the last twenty years. We wanna be the next twenty years. And I look at the evolution, you know, the world is different now than it was when the output created.
17:38
For one, the rise of the influencers,
17:40
particularly gen z, they make all their purchase decision based on influencers.
17:44
And that's true now for dining. So we wanna give it make it really easy rather than scrolling through Instagram and trying to find an old post of a restaurant you saw a month ago. Having it in one tight, really clean UI.
17:56
It's your friends. It's your influencers.
17:58
And then on machine learning, I'm really inspired by TikTok.
18:02
TikTok's an amazing app. They don't ask you any questions. They don't say, you know, what do you what's your interest. But if you look at my TikTok feed, There's a lot of base players. I'm a bad base player, but I like base players. There's a lot of dogs, have a new dog.
18:15
This gardening, it TikTok has figured out the stuff I'm interested in. And without ever asking me question.
18:21
And the way they work is they don't even ask who your friends are. They will find some, you know, DJ and Berlin it's the same weird sense of humor as you, and it'll show you, these are the videos she listens to are that she watches.
18:33
So I really like that look alike modeling or user clustering.
18:37
So we're doing that with Deeps as well. Gonna find your friends, the influencer you like, and then people have the same taste as you.
18:46
This data is wrong every freaking time.
18:48
Have you heard of HubSpot?
18:51
HubSpot is a CRM platform where everything is fully into Well, I can see the client's whole history, calls, support tickets, emails. And here's a test from three days ago, I totally missed
19:03
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. I think a lot of people say it's harder because you don't have the edge. You don't work as hard. That's not true with me. If you talk to anyone who works with me, they'll say I'm working as hard now as I was during my first company when I was blowing through my four zero one k to finance it.
19:28
To me work hard as recruit hard,
19:32
lead, coach people, get people excited,
19:34
and I'm working on that as hard as I ever have. I'm trying to get a little bit better company,
19:38
there is some advantage having money of it. If you see
19:42
a stupid problem
19:44
that cost five grand to fix,
19:47
You know, when you're creating your first company, you don't have that five grand. Now you do. So you just pay a little money and problems go away.
19:52
What do you think, Sean? Easier or harder?
19:56
Yeah. I think it's different. And you just have to, like, work with this the pros and the cons. Right? Like, yeah, recruiting is easier,
20:02
and you waste less time on the on just, like, the rookie mistakes that you always make. But then,
20:08
you know,
20:09
there is some diminishment maybe of the edge, or
20:13
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 in, 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,
20:31
make make the user experience way different. If before we had to ask you fifty questions to show you something good, And now you could swipe three times, four times, and I could start getting you something good.
20:42
You know, I can create a delightful user experience course before, you know, maybe I couldn't. So I think
20:46
Yeah. I think it's different. The things he's saying make a lot of sense to me. I wanna tell you one thing about doing tech now versus twenty years ago, I've been investing for a long time in addition to running companies
20:56
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,
21:06
the open source.
21:10
It's pretty easy to assemble
21:13
the right
21:14
libraries and write people to help put something together. Companies feel today for one of two reasons, either there's a founder and pleasure. They create a talk 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.
21:31
Or number two, they've built a nice product,
21:34
but it's a 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. Like, I have this little problem. I'm gonna work on it for ten 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. When I see a beautiful product, that solves a problem I don't care about.
21:58
Yeah. You see that all the time. That's, like, the number one cause of death.
22:02
I think with, with startups. You, you said something a second ago. I wanted to ask you about. So you go,
22:08
become amazing at recruiting. I,
22:11
that's never been something that I
22:13
was like, that's the thing I'm gonna set my mind to. And you said, you know, I read all the books, read listen to all the podcasts and try to become amazing at this so I can assemble teams to, you know, do your venture studio.
22:24
And,
22:25
you're pretty good at it though, Sean.
22:27
Well, I'm just, like, I don't know. You never know. Right? Like, even,
22:31
Whatever, you know, like it's like a belt system. It's like even if I'm a blue belt, there's still a black belt, you know, that I could go learn from. Even if you're a black belt, there's they're like, oh, I'm I'm just there's lifetimes more to learn about this thing. But I'm curious, Paul, how would you summarize
22:44
for somebody who's talented, but hasn't
22:47
put their focus on becoming great at recruiting?
22:50
What do you think are the,
22:52
give me, like, the the the eighty twenty. The the summary
22:56
of what principles you think are most important when it comes to recruiting. And what are there any that you wouldn't expect? Are they all just things that's like
23:05
I wanna lose weight. It's like eat healthy and exercise. Like, okay. Well, you know, I guess true, but it's not that health not that helpful. I kinda already do that. Are there any things that are maybe counterintuitive
23:14
or, or nuanced that that are important?
23:16
The main thing is just recruit all the time. Always always be recruiting and always be trying to connect with people.
23:22
And you might be going to,
23:25
you know, a coffee social
23:27
to learn about why crypto's terrible
23:30
or whatever.
23:32
And you don't realize that someone gonna be there that would be your next unbelievable CMO. You aren't expecting to meet them. But if you always have your spidey sense out for looking for amazing people, and then once you see them, do whatever it takes to get them to come meet your team. I have a little bit of an off color story, which I probably shouldn't tell. But
23:50
someone asks you once about my true strategy.
23:53
By the way, that's the best starting of a story. So go ahead. I mean, I mean, I like
23:58
okay. So someone asks 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. It's getting me my team. I've trained my team how they should,
24:13
behave in their first meeting with you and all that. And the first thing that came in mind when someone asked you about this about why I'm so laser focused on getting these people
24:21
is one time I was in seventh grade at Boston Latin School
24:25
And I was at my locker, and this really cute girl walked by, and my friend noticed me turn my head and look at her. My friend said,
24:33
English, don't even think about it. She's dating the captain of the football team.
24:37
So at that moment, that girl went in color, and the rest of my roles black and white, Like, I had to date that girl, just because my friends said I couldn't. And I did end up dating her, but it was just like when I recruit and I see someone amazing,
24:50
I'll always ask them, like, do you know anyone even more amazing than you? I did a funny Japanese game show that
24:56
is a guy in Italy looking for the most beautiful woman in the world. And when he encounters the first beautiful man in Italy, he says to her, do you know how many more beautiful than you? And that leads us kind of a hilarious,
25:07
succession of conversations. But when I'm recruiting and I find someone amazing,
25:11
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 fifty who hire you the next five hundred,
25:20
and it's one thing as a founder to convince someone to come meet your company
25:24
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.
25:34
You kind of have, I'm clicking around on your site. You, you and Dharmesh are interesting to me because
25:40
you guys have this, like, dry
25:42
kind of almost nerdy sense of humor that I love. So for example, if you go to lola dot 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,
25:54
PMD,
25:55
PME, that's you dot org. And it's a website where it's like the plain text you're just explaining exactly what happens. And so that's kind of a an interesting way of like going about,
26:05
explaining
26:06
the the the story. But If you click Paul English dot com, it goes to your website, and it talks about some of your cool investments and your your founder stories and things like that. It says like all the clubs you're involved in in one of them, it looks like either you started or you are part of the bipolar social club. I was reading on your Wikipedia, it talked about like you know, you had some issues with bipolar. And I think that, like, the fact that you're part of bipolar social club is that's that's I mean, that's just, like, that's pretty funny. You know?
26:35
I I'd like I'd like guys like you and Darmashes. Why I love Darmashes? He's this guy who's like,
26:41
you talk to him and you're like, oh, you're just a shy. You're you're pretty shy. Then you start talking to him a little more. It's like, oh, you might be, like, quiet, but you're, like, you're kind of a killer. And you're incredibly quirky. For example, he's got a new project called venn diagram dot com, where it's a community for people who love venn diagrams.
26:57
And,
27:00
And then he has another thing called, like, wordplay or something like that where it's like a wordle,
27:05
you know, game that makes like a hundred grand a month or something crazy like that. He just has all these things.
27:10
You kind of seem like that. Are you a guy who's just constantly tinkering
27:14
on on on stuff?
27:16
Yeah. I mean, I have,
27:19
I own about three hundred domain names, and every domain name has a Google Docuent associated with the idea for the company.
27:25
I'm obsessed with brand and names. And I'm and Darmesh and I share this that we're prepared prepared to spend big money to buy a good name.
27:33
And,
27:35
I do I do it. I have lectured a lot of universities, and I gave a lecture on where creativity comes from. And I've done this every day we're from Berkeley School of Music, Doctor with film school, but I'm in school of design, as well as the more traditional universities you would think about.
27:51
And what I do is let's say I'm teaching Thursday at five o'clock.
27:55
At Wednesday at five o'clock, I'll have the professor email the students and say, take a picture of something tonight that annoys you, not a picture you took yesterday, not a picture you found on Google, but take a picture sometime, which annoys you. And then I teach students about how irritation becomes inspiration
28:12
and how any problem can become the motivation for
28:16
a product. We go through a very specific exercise about how to do that. And I am someone who loves ideating. If you look at they say that you're the average of the five people you spend most of your time with. If you wanna change your life, change the people to spend time with. If you look at the people who I hang out with, they care about
28:31
nonprofit work, philosophy, and ideating,
28:34
like improving things. I just have a blast meeting with people like Demesh and saying, how can we fix this? How can we do this better?
28:42
Well, you're in the right spot. So
28:44
we stopped when we started this podcast,
28:46
it was it was doing alright, maybe, I don't know, ten thousand people would listen to every episode. So maybe, like, I don't know, a hundred thousand in in a month, something like that. And, it was a classic interview show. Of what we kind of have done so far, up up till now, we're getting to know you a little bit. Where it's like, oh,
29:03
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 how would you do it, podcast.
29:11
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? Yeah. Why doesn't somebody solve this? Dude, I tried to book this the other day. It was so annoying, and we just started brainstorming. And so we turned the podcast. We called that one the million dollar brainstorm, which is basically ideas that we don't have the time to do. But,
29:33
there were ideas that we thought could be, like, you know, a million dollar billion dollar ideas. And,
29:38
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,
29:50
And there's a lot of people like us that are out there. The same way of Darmesh is trying to find all the Venn diagrammers out there. All the Venners. We're trying to find all the people that love to shoot the shit and brainstorm ideas.
30:00
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 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 gonna have time to go do?
30:13
Sure.
30:15
I'll tell you some ones that
30:17
the itch was enough that I actually
30:19
did a little bit of work on it.
30:22
So one of them was I live in Boston, but I also spent a lot of time in New York where I am today.
30:27
And
30:28
where I live is kind of between West Village and Tobacco.
30:33
And I don't know New York that well. Like, I know the those renable hoods, but I don't really know, like, upper east side, upper west side, whatever. If I'm trying to meet someone
30:42
on the upper west side, I don't know what to meet I'm like, this is annoying that there isn't a website
30:49
where they can see where they are where I am and pick a bar in the middle.
30:53
So I built
30:55
an hour. It's called middle dot net. Haven't have bought that domain name.
30:59
And middle dot net allows you to have two people at three or four as many as you want. It grabs your location from the browser, and it shows you like a coffee shopper bar and a meet in the middle.
31:10
Now I'm never gonna make any money doing that, but I did it just because I needed to know way 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 it out.
31:22
Another one
31:23
When you meet someone so I generally don't really like going to conferences because I'm a little bit shy, a little introverted.
31:29
I've, like, learned how to be extroverted, and I can say more about that. If you care to hear about it. But when you do go to a conference and you meet someone and you wanna swap info,
31:39
it's annoying to do it. You know, you gotta type in phone numbers and stuff better. Type in email addresses. So dumb. Or you can use this dot card thing, but if to carry this card around this card around
31:49
so
31:50
I designed a little app called fun contact. It's fun contact dot com, and allows you to have a sec a a list of QR codes one QR code might be just my email, not only might be my email, my home address. And based on who I'm meeting, what information I wanna share them, I just swiped through and show them the right QR code. They scan it, and I'm in their address book.
32:11
I built that because I needed it. I don't think it'll ever become a company.
32:15
But I just wanted that. So I built it. How many people are using this? This looks cool. I'll use it. I was I just needed one of those things the other day. It's super cool.
32:24
I used it last night. Oh, do you wanna hear a funny story?
32:27
Yeah.
32:28
So
32:30
last night was my three year anniversary with my girlfriend Rachel.
32:33
And we went to San Ambrose in West Village from our first day three years ago. And next to us was Ann Wintour. You know who she is, theater vogue magazine one top socialites in New York and Bradley Cooper on our first day just at NextOS. Last night was at three University. We go to the same restaurant. Guess who's sitting next to us on a wind tour. That was super cool. But at the end of the meeting, I I did talk to her for a couple of minutes, and then she left. And then the table on the other side of me, whereas four people work in the fashion industry where my girlfriend works.
33:04
And we really kind of bonded to talk about a numb I talked about the bipolar social club and the clothing brand I wanna create. And then they asked my number, and I just pulled out fun contact, and I scanned it. Now all these
33:16
young fashion people have my number, and we've been messaging each other today about bipolar social club.
33:24
That's great. What's the clothing brand you wanna create?
33:27
So bipolar
33:28
I have bipolar illness. I was diagnosed at age twenty five,
33:32
and it's a pretty serious illness. 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 ten to fifteen years to learn how to manage it for myself.
33:46
There's bipolar one in bipolar two. I'm bipolar two. So I'm not the most severe type. The most severe type his voices, they end up homeless and
33:53
and or worse,
33:56
not that there's a lot of things for us than being homeless, but
33:59
Bipolar one is pretty serious illness.
34:01
Bipolar two still has problems, but only the years I learned how to deal with it. And I want to be able to
34:08
laugh with all the people bipolar about the funny things about being bipolar.
34:12
So I created this video series. If you go to bipolar social club dot org, There's ten people with bipolar illness who kinda tell their journey.
34:20
And it's kinda destigmatizing
34:21
it saying, yeah, it's a mental illness.
34:23
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 gonna cocktail a party with a hundred people, and is someone like on the other side of the room?
34:35
I can tell they're bipolar, like we recognize each other.
34:39
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 you wanna have a clothing brand, where bipolar people
34:51
kind of wear the brand that prouder, like bipolar and proud. So bipolar social club, we wanted just sort of a fun name.
34:57
Is there anything in,
34:59
in the travel industry that you noticed?
35:02
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 things that you saw because of the scale of kayak and and the company that bought you guys, were there any interesting problems that you felt weren't being entirely solved that you think could actually be quite large you know, big businesses.
35:23
The problem with the travel industry is
35:28
the thing I have the most trouble with is flights.
35:31
And the reports and TSA.
35:33
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.
35:41
That's irritating.
35:43
I wish someone would solve that and make something a lot more efficient and
35:48
safer
35:49
airlines are running on old technology.
35:52
They have to be very conservative because if they make a mistake and adopt something too new, the plane will crash. And obviously they don't want that to happen. So it's very archaic and old. And,
36:03
I'd said earlier that I traveled between Boston and New York, I never fly because
36:09
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 a travel industry, I would like to see fixed. I'd like to see someone that
36:21
figured out how to work with all the unions
36:24
who'll put all these requirements in, who work on the airlines,
36:27
how to work with TSA,
36:29
how to make flying pleasurable.
36:31
It's not pleasurable now. Also remember growing up when you go to the airport. If you used to dress up,
36:36
they'd be, 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
36:44
and make flying pleasant.
36:46
Yeah. Same. It sounds like a the hardest thing on earth to do though.
36:50
What do you think about what Elon's doing?
36:52
So Elon buys Twitter.
36:54
He's kind of taking this, like, you know, technology,
36:58
first thing is try to change the culture overnight, force people back in the office, lay off a bunch of people, try to ship changes really fast. Seems a little bit of 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've followed it quite closely
37:13
And put me in the list of a thousand people who wanna create a Twitter competitor right now. 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 shit show. I think
37:25
I always knew that Elon Musk was eccentric.
37:29
And
37:30
I forgave him for some of his stupid stuff just because he creates such good products.
37:35
I love my tesla cars.
37:37
I'm a happy Tesla Stockholder from two thousand sixteen.
37:41
But when I looked at the way he fired people at at Twitter, it was just obnoxious as fuck.
37:46
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?
37:52
There was no reason you had to march people out of the office. And so I saw that I kinda turned on a little bit.
37:58
And I said,
38:00
I don't like this guy having this much power, whether he's trying to control he's trying to make it the main information so us in the world. Controlled by the richest person in the world. I'm not very happy about that. So
38:10
I'm either gonna Do you think he's gonna pull it off? He does stupid things like the eight doll verification. That was a joke.
38:19
But if he assembles smart people around him it it looks like the smartest people all have left with are already.
38:25
They've all run for the hills,
38:27
but he's gonna hire some new people in 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
38:37
all the intuitive replace that's gonna come out. It's hard to compete with an entrenched
38:41
com company that has hundreds of millions of users because even if the product is better, does Steven King really want a tweet on sampower dot com
38:50
where there'll be, you know, a thousand followers as opposed to Twitter will have a million followers.
38:55
But
38:56
I don't know. I think you start stuff up, and I wanna see the innovation that comes out. That's cool.
39:01
Yeah, I I think that there's
39:04
I think if somebody's gonna do it, they're gonna have to come up with a,
39:09
a social innovation,
39:11
not a,
39:13
It's not a techno it's not a technical innovation.
39:16
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,
39:24
not a change in technology.
39:25
So, like, for example, you know,
39:28
Facebook was this privacy policy change where it was, like, instead of MySpace,
39:33
this is only people that go to your school. And at the door, we gate you with your your school email address. There's a change in privacy policy that totally changed people's behavior because now you're more interested in everybody and you're more willing to share. Then as Facebook became the norm, then it became,
39:49
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-up me. Unilaterally, you could just describe you could decide to get my content. That was totally different than Facebook. Then Snapchat comes out and is like, here's the privacy policy here. All the shit self destructs in twenty four hours, sir. Right? Like, in ten seconds, whatever. So content is not permanent here. And so people flock to that. And so there's just this ongoing shift of, like, the the what is the, like, the social
40:17
rule set that we're gonna follow on this thing And so what's interesting with Twitter is if you're gonna compete with Twitter now, I think you gotta do one of two things. You gotta do it like kind of like gab or truth social 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,
40:42
you have to turn the disadvantage into an advantage. So instead of Steven King saying, Why do I wanna go tweet here when there's only I'm only gonna have a thousand followers over here. You have to make it where it's now benefit like, the perk is that there's only a thousand people there. So it's, like, more like private or in, invite only style communities
40:59
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
41:13
Yeah. I think the decentralized is a joke.
41:16
I think that's technology looking for a solution.
41:19
I think truth social was an epic failure.
41:23
The things that I care about on Twitter right now is
41:27
I'm bothered by all the trolls and the cruelty and
41:32
You know, I look at TikTok,
41:35
and
41:36
I don't watch TV really, but I use TikTok probably twenty minutes a day.
41:40
And
41:41
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 eighteen year old is, like, kinder than the eighteen year old, you know. Do you think that's true? I one hundred percent think it's true. I one hundred percent I think that, like, they don't make fun of each other in the same way that you and I used to make fun of our peers at eighteen. Twitter, I mean, TikTok is amazing. Someone will post a video themself,
42:09
and they'll say, oh, my girlfriend just broke up with me. And,
42:13
you know,
42:14
I think I'm very unattractive
42:15
or
42:17
something like really revealing awkward. And the comments are just unbelievably
42:21
supportive.
42:22
Yeah. It's just so amazing. It's so different than Twitter. And so what you get to know as a Twitter competitor is create the kind Twitter with his no trolls, his no cruelty,
42:31
then also deal with the misinformation. When you see a tweet that says,
42:35
COVID vaccine causes autism,
42:37
like, how do you smack that down?
42:40
And I'm very interested in those two problems getting rid of cruelty
42:44
and flag misinformation,
42:45
but doing it without
42:47
filtering out
42:49
independent info. Like, there's a lot of place 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,
43:01
there's certain personal problems. Like, some people might not wanna say they're bipolar because maybe that will hurt their career.
43:09
But I think this I think this there is a way to build something like Twitter
43:15
that is kind and truth oriented.
43:17
And I haven't spent a lot of time in the last two weeks. Some of it. Some other people are also thinking about doing something new. And I'm confident that there will be something there. Whether it's something that I help people with or something completely independent, I don't know. But somebody needs to create something better. Paul, we
43:32
I'm gonna ask you one last question before we have to move on to the next segment,
43:36
but,
43:37
what's your domain portfolio worth right now, you think?
43:42
So I have three hundred.
43:44
Let's say it costs me ten dollars
43:47
each a year. So I'm spending three thousand a year in domain fees.
43:50
I've paid
43:52
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 me to buy the domain so I'm most settled on. Occasionally, someone will,
44:03
motivate me,
44:05
like, a young entrepreneur who has an idea for demand that I'm not doing anything with it. I'll sell them to them. I don't know. I have some that are worth hundred thousand dollars or more,
44:12
and I have some that are just funny, probably just to me. I'm not surprised on that.
44:17
Lola would be mid six figures, I'd imagine. Right?
44:20
Look, we paid five hundred thousand to buy Lola. Though we were in a bidding war. It's it's up for sale again. I would 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.
44:34
Perfect. Buy back.
44:36
Possibly. Okay. Amazing.
44:42
And,
44:44
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.
44:54
Is that the best place to follow you or should Twitter Yeah. And we're talking about meditation. I talk about getting rid of pain and suffering. I talk about getting rid of anger from your life. It's just my name, paul English dot com. Awesome. Well, Paul, thanks for coming on.
45:07
Appreciate it. Yeah. We appreciate you doing this.
45:10
And, I'm I'm I'm on your bipolar social club. I don't think I have, bipolar, but I still think it's fun to follow along the site. So Awesome. Thank you. And we appreciate you coming. Thanks a lot guys.
00:00 45:39