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

All right, Paul, what's going on, man?

Darmesh, CTO, co-founder HubSpot told us we have to, we don't have to, but we should

talk to you.

Why did he say that?

I don't know.

It's going to be connected.

Darmesh and I have a lot of fun talking together about technology, philosophy, and team.

One fun thing that Darmesh and I did, going back many years ago now, when I was CTO, co-founder

of Kayak, Darmesh and I kind of switched jobs for a day.

So I actually had him made up.

I got him an email address, Darmesh at Kayak.com, and made up business cards.

And he basically sat at my desk at Kayak for a day, and then I sat at HubSpot for a day.

We each, I had Darmesh sit in on a couple of design meetings.

We were designing the next version of our flight search, and he sat there and just sort

of opined and gave opinions about, would this be easy to understand or not.

And then he sat in a couple of architecture reviews and just team project meetings.

And then I had him give a talk about process and culture.

And then I did something similar at HubSpot.

I met with a few of his staff one-on-one, did one-on-one meetings, like it was weekly

one-on-ones, and sat in a couple of project reviews, it was incredibly fun.

I actually recommend that every company do this, that they switch CTOs for a day once

or twice a year, just because if you're running a tech company, the CTO obviously has a big

role about the culture, the architecture, the user interface.

And getting a new perspective a couple of times a year is probably a good thing.

And your big hit has been, well, so far, you have a new company, Lolo, which I don't know

if you know this or not.

You guys advertised with my old company, The Hustle, a bit.

So we worked with you a bit.

But your big hit so far has been Kayak, right?

What did you sell that for?

Like 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.

Which one of the six has been the most financially successful for you?

Kayak was the biggest financial outcome, which I'm deeply appreciative and I learned a lot

at Kayak.

I met some amazing people.

But there's other things which are also really significant that aren't just monetary.

So my first sale, I just told you I sold six in a row.

There's another one that I don't really count, because it only was a company I created in

high school.

But it's very meaningful to me, making money in high school, designing software.

And what were the six?

So I had a company called Boston Light.

We were an e-commerce company that people set up storefronts, a little bit like Shopify.

But this was back 20 years ago.

We sold that to Intuit.

I think MVP technology for Intuit.

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.com, which is serve customer service information to over 200 million

people.

Kayak, Moonbeam, the podcast player.

Lola, which is the business travel and expense.

And did I forget one?

I think that's a list.

And so what's the dot process?

So did you start them all in kind of the same way where you were maybe scratching your own

itch or you're analyzing trends?

So what's your process to come up with these ideas?

It's mostly scratching my own itch.

I mean, I could go through a company by company.

The only one that wasn't my original idea was Kayak.

My co-founder, Steve Hafner, was one of the founders of Orbitz.

And he had observed at Orbitz that 70% of the people in the search on Orbitz.

But then when they were done, they opened a second browser and went directly to United.com

and read it by the ticket.

And so Orbitz did all the searching for people, but never made money.

And so Steve basically said, well, I don't create a company where all we do is search.

And then if someone wants to go to United, they click the link and we'll send them directly

to United and they could buy it there.

And that was his observation.

We met by chance and within probably 45 minutes, decided to sign up as co-founders, each put

a million dollars into the original round of financing.

And then I very quickly owned it from a product standpoint.

I went, I remember spending an hour on Expedia that night because Expedia was the market

leader at that point.

And just going back the next morning saying, this isn't going to be hard because I looked

at Expedia as blowware.

It was sort of seizure inducing.

It was so much stuff going on the screen and slow.

If you put a million dollars in, was that like a, I'm going all my chips on the table

right now or was that a half your net worth?

Was that a small bet for you?

How did you feel at that time?

Did that add some anxiety to the process?

I just sold a company for 30 million.

So the million wasn't that hard for me at that point.

My prior company that I sold for 30, I blew through my 401k to finance it.

So my first company was tough financially to get it going.

But for Kayak, I had made some money, so I could afford to help finance it.

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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

control for a long time.

Like Darmesh, right?

Darmesh has been doing HubSpot for forever.

Yeah.

So Kayak, I did for 10 years.

That was my longest stint.

And we ended up taking it public 2012, which was incredibly fun.

And then we sold it shortly thereafter to the price sign at reallybooking.com, which is

the parent company.

And I just, frankly, was bored.

I felt like I was editing the flight screen for 10 years and I wanted to try something

new.

I had an unbelievably strong team at Tech Leadership at Kayak.

So at that point, I felt like I could sneak out without hurting the company because I

had people at that point that could do UI, they could do product, they could do architecture.

So it gave me the freedom to try something new.

You, you're kind of, I mean, you're, you're kind of like an internet OG a little bit.

I mean, Kayak's one of the, was like a pretty huge thing.

It still is a huge thing, but in terms of like internet exits, it was, it was, it was

early on into, in the game, and you guys had a nice huge exit.

Who are some of the people who were kind of like big shots and ballers now that you got

to know a little bit earlier on?

You mean across the industry?

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 I'm sure there's like a story

where he's like, well, I met this guy, Brian, and he was like living out of a closet and

doing all this weird stuff.

And he was a quirky guy and, and I mean, he just has met, or I believe he was an early

investor in Dropbox as well.

And like, he probably has all these interesting stories about some of these folks who are

now like tycoons or big deal now, but he was fortunate because he's a little bit older

and was more successful than they were when they were just getting their things started,

that he got insight into these businesses.

Do you have anything like that?

Yeah.

And I met Brian Chesky at Airbnb when they were financing a billion dollar valuation

and I think the net worth a hundred billion or something like that.

And I remember the time like loving Brian thought he was iconic and passion driven,

mission driven, but I didn't see it how big Airbnb was going to get.

I said, this seems awesome for people who want to have strangers living in the house,

but how many people are going to be?

So I kind of missed the bigger picture there.

What was he like when you met him?

Just I've seen him talk.

My wife works there.

I totally agree.

I think he is an icon.

I think he's one of the best CEOs out there.

He's passion driven.

He's amazing.

But what did you see?

I saw him as very serious and intense.

He was charismatic.

He listened well.

So we had a good conversation where he wanted me to give him feedback of the company because

CAC was a much bigger company at that point.

Who else were you able to meet?

Yeah, whenever you're doing technology for like 15, 20 years, you just get this like

crazy story arc or like, you know, you get to see people.

You see all these people that you're like, all right, I think this person is kind of

amazing.

They might go on to do amazing things.

Maybe it's this idea.

Maybe it's the next idea.

Are there any other stories like that that you've seen because you've been kind of in

the game for such a long time?

Yeah.

So when we financed, we had CAC was created in 2004.

We've really launched out of General Catalysts in Cambridge, Mass.

And then we raised money from Mike Moritz, Sequoia, and then one day my co-founder and

I were working out of Square office and Mike Moritz said, oh, I want to introduce you to

a couple of guys.

This is Chad Hurley and that's good as co-founder, but they were the founders of YouTube.

Steve Chan, I think.

Yeah, that's right.

And I remember meeting those guys in Square office and Mike's like, yeah, these guys are

like putting videos online.

I'm like, yeah, that's cool.

Whatever.

I didn't see that one either.

I have some famous misses.

I mean, I've been one of these investor.

I think my IR is 30.5% over the last several years, so I've been pretty good.

I've invested in 60 companies, but I've missed some.

I missed Snapchat.

I met one of their founders when they were financing an $80 million valuation.

That would have been a big outcome.

Dropbox I met Drew early on.

And that wasn't under the guise of me investing in them, it was really just networking.

But I thought Dropbox is going to be plagued by security.

I'm still kind of shocked.

I use Dropbox.

Do you know that they don't really encrypt your files and that a Dropbox engineer, if

they're malicious, they can get at just your files?

Yeah, I believe that.

It's amazing that they're as big as they are.

And why doesn't anyone worry about that?

What have been the, you said you've invested in 60 companies and you got this great IR.

What have been some of the hits so far?

One of the ones going to right now is Pilot.com and yeah, that's an amazing company.

I met those guys when they were, I was a judge at the MIT 100K competition and had a company

called Case Place, really exotic technology.

They could patch a Linux operating system as it was running so you don't have to reboot

your servers.

They sold that to Oracle.

I was part of, you know, I was the judge at that and I helped them win that competition.

And then I invested in their next company, Zula, which they ended up selling to Dropbox.

And then when they left Dropbox, created another company, I basically asked them if I can invest

before I knew what they were working on.

So I wrote them a check before I knew what they were doing and that's a 40XR.

I think I financed them.

I wrote a check as part of the rounded $30 million valuation.

I think their last valuation was like $1.2 billion or something.

But that's one that the founding team had the mojo.

So when you met them, you just knew those guys were going to create something serious.

They were intense, high energy.

They laughed a lot.

They finished each other's sentences.

They just really enjoyed working together.

I also, in order to give a return for me, a 22X was Ken Show, which is a competitor

to a Bloomberg terminal.

And I invested in them because their CTO Pete Krasko used to work at Kayak and I knew him

from Kayak.

And I just knew he was destined to do great things.

And that was a really nice exit.

We had this guy, Trong, work for us.

So Trong was an analyst at Ken Show.

And Ken Show is like this, you know, they're a startup still, but like the stereotype,

to me, from an outsider, they kind of fit this like stereotype of like an uptight financial

firm.

And we found Trong working there.

And this guy, Trong, who works for us, he's like, 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 encourage him to

use Twitter.

And now he's got like, you know, a million followers on Twitter and we recruited him

from Ken Show.

That's amazing.

I like Ken Show because of that.

Thank you.

And you, so Kayak was a big win.

And then you did things like let's say Moonbeam, which is like, you know, a podcast discovery

type of app could have been big, but you know, maybe I think anything in podcasting is sort

of like looks sort of niche and most of the podcast products, even that win are sort of

like really good lifestyle businesses so far.

There hasn't been that many big winners in the podcasting space in terms of tools.

Are you, do you, I know one thing that's hard to talk to people who kind of have an exit

like 700 million or 800 million or a billion dollars, it's like, that becomes the new table

stakes for the next thing they do.

Some go that way and they say, okay, I got to get huge now.

And others are like, no, I'm literally just going to program things in my house for fun

now.

Like now I don't want to go try to catch lightning in a bottle again.

Which way do you think about it?

Or is there another, a third way?

I've always said for each of my companies, it's team first, customer second, profit third.

I set it for Kayak on day one, we put together our culture plan.

And I really think it's a good way to execute because if you focus on becoming a phenomenal

recruiter and really becoming a student of recruiting, like read all the books, listen

to the podcasts, learn from others to talk about recruiting and recruit an amazing team

and then figure out how to lead that team so that there's no stress in the office.

People work really hard, they have fun, they're cranking stuff out, but they're not stressing

each other out.

If you do those things, you can create, I always say magic teams create magical products.

And then usually if you can create a magical product, you can find a profit business there.

So for me now, after I sold Lola, my business travel and expense company, I sold that to

Capital One a year ago, I then opened up a venture studio called Boston Venture Studio.

It's bvs.net and we have nine apps under development.

Some of them are in itch to scratch, like fun little things that we put out with source

code.

Others are a swing for the fences, really thinking it can become big.

There's a company I launched two weeks ago called Deets, like show me the Deets.

That could be a billion dollar company.

What we're doing is we're saying online reviews are broken.

If you go to Google right now and in quotes, you search for buy Amazon reviews, you'll

see this 37,000 pages that tell you how to do that.

If you make these headphones I'm wearing, if you make a competitor to these and you

want to sell it on Amazon, you can easily buy a thousand five-star reviews for that

if you want.

And these fake review companies are run by PhD computer scientists.

They're evading Amazon's bot detection, so it's very difficult at this point to detect

them.

They're going through proxy servers, they have age accounts, they buy products.

And then if you go to Yelp or TripAdvisor, their reviews are largely by people you don't

care about.

You know, like, I looked up a sushi restaurant in New York and I saw five-star reviews of

this place.

People talked about how great it was because it was really cheap.

And I don't know about you if you like sushi or not, but I'm not sure I'm going to be

that excited to have $10 a person, but sushi in New York, that's a little scary to me.

Yeah, you want that catfish and cream cheese roll.

Yeah.

If you go on TripAdvisor and you look for Hotel, you'll see a lot of five-star reviews

from Hotel 6, and that was great when I was 20 years old.

I'm not sure I would say to Hotel 6 now, but a lot of you just don't relate to the person

doing the purchase.

So the idea of DEETS is going to blow that up and say, it's just the recommendations

from your friends, from influencers that you choose to follow, and then using machine learning

doing lookalike modeling to find people that are similar to you.

Man, it seems like you pick really hard industries.

Like, travel is like, you know, again, I'm an outsider, you're the expert.

But it seems like notoriously difficult.

Like it just seems like incredibly competitive and very, very, very challenging, and the

margins seem small and very hard.

It seems to start one of those things now.

Podcasting, terribly hard.

I don't, you know, I don't entirely understand why it's so hard, but like the, nothing has

entirely clicked to make it this, this fantastic industry, 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 five or 10 years.

Their stock sucks.

Google reviews is a horribly challenging person to compete with because, you know, they have

all these people already using it.

What's the game, what's the game plan here and why are you picking the hardest things

to work on?

Yeah, the origin of DEETS is I'm friends with some people who own restaurants in Boston,

and I saw the difficulty they had during COVID.

And so it really developed some compassion for restaurant owners.

And they all told me how much they hate Yelp.

Yelp is this like mafia, where you pay, if they call you and they save a lot of bad

reviews, call us and pass hundreds of dollars a month that will sort of clean up your site

on Yelp.

It's kind of like in Italy, there's a movie called Billion Dollar Bully about Yelp.

It came out in 2019 and the opening scene is an Italian chef who said when he opened

his first restaurant in Italy, his son broke the windows.

He fixed them.

They broke them in the next week, he fixed them.

The next week, some guy comes in and says, I noticed someone keeps breaking the windows.

If you pay me $100 a week, I'll make sure no one breaks the windows anymore.

And he knew that was the guy who was breaking the windows.

He's like, Yelp was just like that.

So I look at Yelp as a 20-year-old dinosaur.

That's the last 20 years.

We want to be the next 20 years.

And I look at the evolution, you know, the world is different now than it was when Yelp

were created.

For one, the rise of the influencers, particularly Gen Z, they make all their perks decision based

on influencers.

And that's true now for dining.

So we want to give it, make it really easy.

Right on scrolling through Instagram and trying to find an old post of a restaurant you saw

a month ago, having it in one tight, really clean UI.

It's your friends.

It's your influencers.

And then on machine learning, I'm really inspired by TikTok.

TikTok's an amazing app.

They don't ask you any questions.

They don't say, you know, what's your interest?

But if you look at my TikTok feed, there's a lot of bass players.

I'm a bad bass player, but I like bass players.

There's a lot of dogs, I have a new dog on this gardening.

TikTok has figured out the stuff I'm interested in.

And without ever asking me a question.

And the way they work is they don't even ask you who your friends are.

They will find some, you know, DJ and Berlin, who has the same weird sense of humor as you

and they'll show you these, the videos she listens to or that she watches.

So I really like that.

Lookalike modeling or user clustering.

So we're doing that with these as well.

We're going to find your friends, the influencers you like, and then people of the same taste

as you.

Do you think that starting a company now that you're wealthy is easier or harder than when

you are just getting going in your career?

I think a lot of people say it's harder because you don't have the edge, you don't work as

hard.

That's not true with me.

If you talk to anyone who works with me, they'll say I'm working as hard now as I was

during my first company when I was blowing through my 401k to finance it.

To me, work hard is recruit hard, lead, coach people, get people excited.

And I'm working on that as hard as I ever have.

I'm trying to get a little bit better with each company.

There is some advantage of having money that if you see a stupid problem that costs five

grand to fix, you know, when you're creating your first company, you don't have that five

grand.

Now you do.

So you just pay a little money and problems go away.

What do you think, Sean?

Easier or harder?

Yeah, I think it's different.

And you just have to work with the pros and the cons, right, like, yeah, recruiting is

easier and you waste less time on just the rookie mistakes that you always make.

But then, you know, there is some diminishment maybe of the edge or, you know, the things

that made you successful the first time might have been that there was a technology wave

going on.

There was a bunch of opportunity.

And like, you have to recognize new technology waves or new inflection points, new things

that have changed.

You know, he's talking about like, basically, machine learning has gotten a lot better.

And now we can do things that like make the user experience way different.

If before we had to ask you 50 questions to show you something good, and now you could

swipe three times, four times, and I could start getting you something good, you know,

I can create a delightful user experience whereas before, you know, maybe I couldn't.

So I think, you know, I think it's different and the things he's saying make a lot of sense

to me.

I want to tell you one thing about doing tech now versus 20 years ago, I've been investing

for a long time in addition to running companies, and in the old days, companies would fail

because their product didn't work, they just couldn't get the tech working.

That's hardly the case now, like the stack, the AWS, the tools, the open source.

It's pretty easy to assemble the right libraries and right people to help put something together.

Companies feel today for one of two reasons.

Either there's a founder implosion, they create a toxic culture and people like hate their

boss and they hate working there and they all leave, which unfortunately happens all

too often, they fail the culture code, or number two, they've built a nice product,

but it's a real problem that no one cares about, and unfortunately, a lot of founders

have an itch to scratch, as you were saying earlier, Sam, and they get really obsessed

about it, like I had this little problem, I'm going to work on it for 10 years, and

they don't realize that not a lot of people have that same problem.

It makes me sad when I see that, when I see a beautiful product that solves the problem

I don't care about.

Yeah.

You see that all the time.

That's like the number one cause of death, I think with startups.

You said something a second ago I wanted to ask you about, so you go, become amazing

at recruiting.

That's never been something that I was like, that's the thing I'm going to set my mind

to.

And you said, I read all the books, listened to all the podcasts and tried to become amazing

at this, so I can assemble teams to do your venture studio.

And you're pretty good at it though, Sean.

Well, I'm just like, I don't know, you never know, right, like even whatever, you know,

like it's like a belt system.

It's like, even if I'm a blue belt, there's still a black belt, you know, that I could

go learn from.

Even if you're a black belt, they're like, oh, I'm just, there's lifetimes more to learn

about this thing.

But I'm curious, Paul, how would you summarize for somebody who's talented, but hasn't put

their focus on becoming great at recruiting?

What do you think are the, give me like the 80, 20, the summary of what principles you

think are most important when it comes to recruiting?

And are there any that you wouldn't expect?

Are they all just things that's like, I want to lose weight.

It's like, eat healthy and exercise, like, okay, well, you know, I guess that's true,

but it's not that helpful.

I'm not that helpful.

I kind of already do that.

Are there any things that are maybe counterintuitive or nuanced that are important?

The main thing is just recruit all the time, always, always be recruiting and always be

trying to connect with people.

And you might be going to a, you know, a coffee social to learn about why crypto is terrible

or whatever.

And you don't realize there's someone going to be there that would be your next unbelievable

CMO.

You weren't expecting to meet them, but if you always have your spidey sense out for

looking for amazing people, and then once you see them, do whatever it takes to get

them to come meet your team, I have a little bit of an off color story, which I probably

shouldn't tell, but someone else who wants to vote member could be strategy.

By the way, that's the best starting of a story.

So go ahead.

Yeah.

I mean, I like worked up.

Okay.

So someone asked me about my recruiting style, because if you've been recruited by me, you'll

know that I'm like very, very aggressive to do whatever it takes to get you.

I'll come meet you at a Starbucks near you.

I'll do it.

I just get to meet my team.

I've trained my team how they should behave in their first meeting with you and all that.

And the first thing that came to mind when someone asked me about this, about why I'm

so laser focused on getting these people is one time I was in seventh grade at Boston

Latin school and I was at my locker and this really cute girl walked by and my friend noticed

me turn my head and look at her.

My friend said, English, don't even think about it.

She's dating the cap and the football team.

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 my friend said I couldn't and I did end up dating her,

but it was just like when I recruit and I see someone amazing.

I'll always ask them like, do you know anyone even more amazing than you?

There's a funny Japanese game show that is a guy in Italy looking for the most beautiful

woman in the world.

And when he encounters the first beautiful woman in Italy, he says to her, do you know

anyone even more beautiful than you?

And that leads to kind of a hilarious succession of conversations.

But when I'm recruiting and I find someone amazing, I'll just do what it takes to get

them excited and to get them to meet my team.

And I've always said that the first five people hire you the next 50 who hire you the next

500.

And it's one thing as a founder to convince someone to come meet your company.

But if you've been really good at recruiting that first five, those five will close the

candidate for you.

When they meet those five, they'll say, oh my God, I need to work with this team.

You kind of have, I'm clicking around on your site.

You and Darmesh are interesting to me because you guys have this like dry kind of almost

nerdy sense of humor that I love.

So for example, if you go to Lola.com, it basically says the domains for sale, but you

can see the history of Lola by clicking here and it goes to PMD, PME, that's you.org.

And it's a website where it's like plain text.

You're just explaining exactly what happens.

And so that's kind of an interesting way of like going about explaining the story.

But if you click PaulEnglish.com, it goes to your website and it talks about some of

your cool investments and your founder stories and things like that.

And then it says like all the clubs you're involved in.

And one of them, it looks like either you started or you are part of the bipolar social

club.

I was reading on your Wikipedia.

It talked about like, you know, you had some issues with bipolar.

And I think that like the fact that you're part of bipolar social club is that's, I mean,

that's just like, that's pretty funny.

You know, I like, I like guys like you and Darmesh.

Why I love Darmesh is he's this guy.

You talk to him and you're like, oh, you're just a shy, you're pretty shy.

And then you start talking to him a little more and it's like, oh, you might be like

quiet, but you're like, you're kind of a killer and you're incredibly quirky.

For example, he's got a new project called Venn diagram.com where it's a community for

people who love Venn diagrams.

And then he has another thing called like word play or something like that where it's

like a wordle, you know, game that makes like a hundred grand a month or something crazy

like that.

And he just has all these things.

You kind of seem like that.

Are you a guy who's just constantly tinkering on, on, on stuff?

Yeah.

And I have, um, I own about 300 domain names and every domain name has a Google Doc it

associated with the idea for the company.

I'm obsessed with brand and names and I'm, and Darmesh and I share this that we're prepared,

prepared to spend big money to buy a good name.

And I have lectured a lot of universities and I give a lecture on where creativity comes

from.

And I've done this every day.

We're from Berkeley School of Music, Dartmouth Film School, where I'm in school of design,

as well as the more traditional universities you would think about.

And what I do is let's say I'm teaching Thursday at five o'clock.

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 the students about how irritation becomes inspiration and how any problem can

become the motivation for a product.

And we go through a very specific exercise about how to do that.

And I am someone who loves ideating.

If you look at, they say that you're the average of the five people you spend most of your

time with.

If you want to change your life, change the people you spend time with, if you look at

the people who I hang out with, they care about nonprofit work, philosophy and ideating,

like improving things.

I just have a blast meeting with people like Darmesh and saying, how can we fix this?

How can we do this?

Well, you're in the right spot.

So when we started this podcast, it was doing all right, maybe, I don't know, 10,000 people

would listen to every episode.

So maybe like, I don't know, 100,000 in a month, something like that.

And it was a classic interview show, similar to what we kind of have done so far up till

now, getting to know you a little bit.

But it's like, oh, oh, you built Kayak, amazing.

Tell me about it.

You know, how'd you do it?

And it was just like every other tech or business podcast, which is a how would you

do it podcast?

And then one day, just to mix it up, I was like, I invited Sam on, I was like, Sam,

let's just shoot the shit like we do when we're not on a podcast about like, oh, have

you seen this?

Yeah.

Why doesn't somebody solve this?

Dude, I tried to book this the other day was so annoying.

And we just started brainstorming.

And so we turned the podcast, we called that one the million dollar brainstorm, which is

basically ideas that we don't have the time to do.

But there were ideas that we thought could be like, you know, a million dollar, billion

dollar ideas.

And then the whole podcast took off.

And so now it's like, in the top ranks of the charts and all this stuff.

And it's, I think, because we switched into this like, ideating brainstorm mode.

And there's a lot of people like us that are out there.

The same way, Darmash is trying to find all the Venn diagrammers out there, all the Venners.

We're trying to find all the people that love to shoot the shit and brainstorm ideas.

Sounds like you're one of them.

So can you give us a couple of ideas or maybe from your domains, you know, pull three names

and what's the, what's the one line pitch you have in mind for some ideas that you'll

probably never have time to go do?

Sure.

I'll tell you some ones that the itch was enough that I actually did a little bit of

work on it.

So one of them was I live in Boston, but I also spent a lot of time in New York where

I am today.

And where I live is kind of between West Village and Tribeca, Nesoho.

And I don't know New York that well.

Like I know the, those three neighborhoods, but I don't really know like Upper East Side,

Upper West Side, whatever.

If I'm trying to meet someone on the Upper West Side, I don't know where to meet.

I'm like, this is annoying that there isn't a website where they can see where they are,

where I am and pick a bar in the middle.

So I built an app.

It's called middle.net.

I went, I bought that domain name and middle.net allows you to have 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 shop or bar to

meet in the middle.

Now I'm never going to make any money doing that, but I did it just because I needed to

know where to meet people in New York as I was getting used to the city.

I couldn't find a way to do it.

So I built an app.

Another one, when you meet someone, so I generally don't really like going to conferences.

So I'm a little bit shy, a little introverted.

I've like learned how to be extroverted.

And I can say more about that if you care to hear about it.

But when you do go to a conference and you meet someone and you want to swap info, it's

annoying to do it.

You know, you got to type in phone numbers and stuff, you got to type in email addresses.

So dumb.

We can use this dot card thing, but if to carry this card around, this card around.

So I designed a little app called Fun Contact.

It's funcontact.com and allows you to have a list of QR codes.

One QR code might be just my email, another one might be my email, my home address.

And based on who I'm meeting, what information I want to share them, I just swipe through

and show them the right QR code.

They scan it and I'm in their address book.

I built that because I needed it.

I don't think it'll ever become a company, but I just wanted that.

So I built it.

How many people are using this?

This looks cool.

I'll use it.

I just needed one of those things the other day.

It's super cool.

I used it last night.

Oh, do you want to hear a funny story?

Yeah.

So last night was my three year anniversary with my girlfriend, Rachel.

And we went to San Ambrose in West Village for our first day three years ago.

And next to us was Ann Wintour, who she is, she's the editor of Vogue Magazine, one of

the top socialites in New York, and Bradley Cooper on our first day to sit next to us.

Last night was our three year anniversary.

We'd go to the same restaurant, guess who's sitting next to us on a Wintour.

That was super cool.

But at the end of the meeting, I did talk to her for a couple of minutes and then she

left.

And then the table on the other side of me was four people working in the fashion industry

where my girlfriend works.

And we really kind of bonded to talk about, I talked about the Bipolar Social Club and

the clothing brand I want to create.

And then they asked my number and I just pulled out Fun Contact and I scanned it.

Now all these young fashion people have my number and we've been messaging each other

today about Bipolar Social Club.

That's great.

What's the clothing brand you want to create?

So I have bipolar illness.

I was diagnosed at age 25 and it's a pretty serious illness.

You know, a lot of people end up killing themselves or ruining their marriage or their job or

their lives.

And it took me a good 10 or 15 years to learn how to manage it for myself.

There's bipolar one and bipolar two.

I'm bipolar two.

So I'm not the most severe type.

The most severe type, his voice is they end up homeless and or worse.

Not that there's a lot of things for us in being homeless, but bipolar one is pretty

serious illness.

Bipolar two still has problems, but over the years, I learned how to deal with it.

And I want to be able to laugh with other people bipolar about the funny things about

being bipolar.

So I created this video series.

If you go to bipolarsocialclub.org, there's 10 people with bipolar illness who kind of

tell their journey.

And it's kind of destigmatizing it, saying, yeah, it's a mental illness.

And there's some shitty things about it, but there's some funny things about it too.

And I have this thing about bipolar people that if I'm 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.

Like we recognize each other.

My gay friends say they have gaydar.

They can tell gay people across the room.

I can tell bipolar people across the room and we're trying to do something fun.

So you want to have a clothing brand where bipolar people kind of wear the brand.

They're proud of it, like bipolar and proud.

So bipolar social club, we wanted to sort of a fun name.

Is there anything in the travel industry that you noticed, I mean, because you had more

data than, you know, there's probably only hundreds of people in the world or maybe low

digits thousands that are able to kind of see some of the things that you saw because

of the scale of kayak and the company that bought you guys.

Were there any interesting problems that you felt weren't being entirely solved that you

think could actually be quite large, you know, big businesses?

The problem with the travel industry is the thing I had the most trouble with is flights

and airports and TSA.

TSA is a joke.

The stuff that they do to you, it gives you a false sense of security, but there's no

real security with TSA.

That's irritating.

I wish someone would solve that and make something a lot more efficient and safer.

Airlines are running on old technology.

They have to be very conservative because they make a mistake and adopt something too new,

the plane will crash and obviously they don't want that to happen.

So it's very archaic and old and I said earlier that I travel between Boston and New York.

I never fly because by the time you go through TSA security and get an Uber in each end,

it's just, it's often faster to drive.

So as far as things in the 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 on the airlines, how to work with TSA, how to make flying pleasurable.

It's not pleasurable now.

I also remember growing up, when you go to the airport, people used to dress up.

They were like really excited to get on a plane to travel.

But now airports are just a nightmare and I wish someone could make airports pleasant

and make flying pleasant.

That's cool.

It's the same, it sounds like the hardest thing on earth to do though.

What do you think about what Elon's doing?

So Elon buys Twitter, he's kind of taking this like, you know, technology first thing,

he's trying to change the culture overnight, force people back in the office, lay off a

bunch of people, try to ship changes really fast, seems a little bit helter-skelter.

Have you followed that?

And I'm curious, what's your opinion as a CTO and somebody's done tech for a long time?

I followed it quite closely and put me on the list of a thousand people who want to create

a Twitter competitor right now.

I've been spending a bunch of time in the last week ruminating on that.

And I think it's a bit of a shit show.

I think, I always knew that Elon Musk was eccentric.

I forgave him for some of his stupid stuff just because he creates such good products.

I love my Tesla cars, I'm a happy Tesla stockholder from 2016.

But when I looked at the way he fired people at Twitter, it was just obnoxious as fuck.

Like, do you really need, you are the richest guy in the room, in the world, do you really

need to also be an asshole?

There was no reason you had to mark people out of the office.

And so when I saw that, I kind of turned on a little bit and I said, I don't like this

guy having this much power that he's trying to control, he's trying to make it the main

information source of the world, controlled by the richest person in the world.

I'm not very happy about that.

So, I mean-

You think he's going to pull it off?

He does stupid things, like the eight dollar verification, that was a joke.

But if he assembled smart people around him, it looks like the smartest people all have

left Twitter already, they've all run for the hills.

But he's going to hire some new people in.

I'm sure there's some good people that are still there.

I'm sure he'll do some interesting things with it, but I'm really looking forward to

all the Twitter replacements that are going to come out.

It's hard to compete with an entrenched company that has hundreds of millions of users because

even if the product is better, does Stephen King really want to tweet on sampower.com

where there'll be a thousand followers as opposed to Twitter where they'll have a million

followers?

But, I don't know, I think he stirred stuff up and I want to see the innovation that

comes out.

Yeah.

I think that if somebody's going to do it, they're going to have to come up with a social

innovation and it's not a technical innovation.

So, I have this long running theory about social networks, which is that every social

network is a change in privacy policy, not a change in technology.

So, for example, Facebook was this privacy policy change where it was like, instead of

Myspace, this is only people that go to your school and at the door, we gate you with your

school email address.

It was 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 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 can just follow me.

Unilaterally, you could just describe, you could decide to get my content.

That was totally different than Facebook.

Then Snapchat comes out and is like, here's the privacy policy here.

All the shit self-destructs in 24 hours, right, like 10 seconds, whatever.

So content is not permanent here and so people flock to that.

And so there's just this ongoing shift of like, what is the social rule set that we're

going to follow on this thing?

And so what's interesting with Twitter is, if you're going to compete with Twitter now,

I think you got to do one of two things.

You got to do it like kind of like gab or truth socials trying to do, but somebody could

actually pull that off where they basically take a community of people that are pissed

off about Twitter and there's enough pissed off people to go into their own echo chamber.

I think that's possible.

And then the other one is, I think if you created, you have to turn the disadvantage

into an advantage.

So instead of Stephen King saying, why do I want to go tweet here when there's only,

I'm only going to have a thousand followers over here, you have to make it where it's

now benefited.

Like the perk is that there's only a thousand people there.

So it's like more like private or invite only style communities that you can join that

have the same content format as Twitter or something like that, I think is more likely

to work than what people are trying today, which is just we're Twitter, not owned by

Elon Musk or we're decentralized Twitter.

And it's like, nobody cares.

Yeah.

I think the decentralized is a joke.

I think that's technology looking for a solution.

I think truth social was an epic failure.

The things that I care about on Twitter right now is I'm bothered by all the trolls and

the cruelty.

And I look at Tik Tok and I don't watch TV really, but I use Tik Tok probably 20 minutes

a day.

And I like how positive Tik Tok 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.

But the average 18 year old is like kinder than the 18 year old.

No.

Do you think that's true?

I 100% think it's true.

I 100% I think that like they don't make fun of each other in the same way that you and

I used to make fun of our peers at 18.

Twitter.

I mean, Tik Tok is amazing.

Someone will post a video themselves and they'll say, Oh, my girlfriend just broke up

with me.

And, you know, I think I'm very unattractive or something like really revealing awkward

and the comments are just unbelievably supportive.

Yeah.

It's just amazing.

It's so different than Twitter.

And so what I want to do as a Twitter competitor is create the kind Twitter where there's no

trolls, there's no cruelty and then also deal with the misinformation when you see a tweet

that says COVID vaccine causes autism, like how do you smack that down?

And I'm very interested in those two problems, getting rid of cruelty and flag misinformation,

but doing it without filtering out independent info, like there's a lot of places in the

world right now where it's scary to be publicly identified and to state your opinion.

And maybe even the U.S. if you're the certain personal problems, like some people might

not want to say they're bipolar because maybe that will hurt their career.

But I think this, I think there is a way to build something like Twitter that is kind

and truth oriented.

And I've been spending a lot of time in the last two weeks bringing something with some

other people also thinking about doing something new.

And I'm confident that there will be something new, whether it's something that I help people

with or something completely independent, I don't know, but someone needs to create something

better.

Paul, I'm going to ask you one last question before we have to move on to the next segment.

But what's your domain portfolio worth right now, you think?

So I have 300, let's say it costs me $10 each a year.

So I'm spending $3,000 a year in domain fees.

I've paid hundreds of thousands of dollars to buy domains.

I don't sell them that often because I still hold on to the idea that costs me to buy the

domain.

So most of them on occasionally, someone will motivate me like a young entrepreneur has

an idea for a domain that I'm not doing anything with, and I'll sell them to them.

I don't know.

I have some that are worth $100,000 or more.

And I have some that are just funny, probably just to me.

So I'm not trying to put price on that.

Lola would be mid six figures, I'd imagine, right?

We paid $500,000 to buy Lola.

We were in a bidding war.

It's up for sale again.

It's up for sale.

Yeah.

We sold the company to Capital One.

They want everything to be Capital One.

They didn't want the name Lola.

So the name is for sale.

Perfect.

Buy it back.

Possibly.

Okay.

Amazing.

And where should people go find you?

I'm on your website.

I think your website's pretty cool.

You have like, here's how I manage my time.

Here's how I run meetings.

I love when people do that, when they put their like operating playbooks out there.

Is that the best place to follow you?

Or should Twitter?

Yeah.

I talk about meditation.

I talk about getting rid of pain and suffering.

I talk about getting rid of anger from your life.

It's just my name, parlinklish.com.

Awesome.

Well, Paul, thanks for coming on.

Appreciate it.

Yeah.

We appreciate you doing this.

And I'm on your bipolar social club.

I don't think I have bipolar, but I still think it's fun to follow along this site.

So thank you.

Awesome.

Thank you.

And we appreciate you coming.

Thank you.

Bye.

Bye.

Bye.

Bye.

Bye.

Bye.

Bye.

Bye.

Bye.

Machine-generated transcript that may contain inaccuracies.