I was like, I'm doing what I think is

interesting and I hope that is aligned

with what makes Clay successful. I'm

interested in that, but actually I want

to make these people successful. And

they felt that genuiness and we did

really crazy, you know, Verun, I think

he was talking to someone on WhatsApp

and the person was having trouble fixing

something on Clint. He was like, I'm

coming over to your house right now. And

the guy was like, don't come. He was

like, no, I'm coming. and he they became

really good friends and we were just

kind of on that journey with them. Uh

truly

everybody we have Kareem the founder CEO

of Clay on today. Clay is ripping. He's

doing a nice job there. He is a very

interesting cat. You're about to find

out. He's kind of a philosopher

monklike CEO and he's coloring way

outside the lines. I think you're going

to like it. I did a bunch of work to

prep, but the the best prep was I got a

little chance to engage with Verun, your

head of go to market, and he said he

talked about your Padell game that you

guys play a lot of Padell. and he says

he absolutely crushes you.

>> He loses quite a bit.

>> And he said, "You're relentless and

positive and no one tries harder." Where

does that come from?

>> Um I just want to correct the record

before we move on.

>> I'm going to call BS on his behalf.

>> Yeah. I I have a video of him lying on

the floor literally with his ankle uh

almost broken because he thought the

ball was going one way and it went the

other. and it just messed with his mind.

And

>> he said you guys wager and the wagers

increase and that you're like, "Let's go

again. Let's go again."

>> Well, I think Yeah, I think maybe what

he's talking about is that I like, you

know, especially in sports or things

like that, when someone beats me in

something, um, I automatically get

charged up rather than charged down.

Sometimes I'm playing actually with

Verun against someone else and if we

lose, he wants to change teams, which

really baffles me. Okay.

>> It actually that actually really gets to

me because when I lose I'm like here's

the here, you know, especially in a game

where you're losing by just one or two

points and you can almost see it going

your way. I can see that difference and

how close we were and how we can kind of

get there next time. Whereas he want he

thinks it's less it's less fun and like

we should switch teams.

>> Where does that come from little Kareem?

Where did where did you get so

competitive? Where does the drive come

from?

>> Wow, that's a deep cut. Yeah, let's go.

You really went there.

>> Yeah.

>> Um

>> I'm kind of studying CEOs and I kind of

want to see like what are the patterns?

>> Yeah,

>> a lot of CEOs are immigrants. Is it sort

of an immigrant edge?

>> I'll tell you kind of like where I've

gotten to after thinking about that or

analyzing it. Um it's it sounds a bit

benal, but I I think I had a um unusual

childhood. Let's just say just like

parents divorced both really great

parents just big divorce and you know

traveling across like different

countries very loud lots of things

happening and like my introspection is

that

>> the ambition comes from you know the if

you like a really simple thing right

like if you can do something really big

then you'll be loved right um and a big

part actually of while building the

company that I feel like I've um come to

understand but also resolve and calm

down is that um one thing that I I've

like actually told people at work is

that a lot of people think you should

build from a place of lack uh or like

you know you have a chip on your

shoulder you need to prove something and

you can definitely build great things

that way but I think you create a lot of

damage along the way um and to me I've

decided to create from a place of

wholeness so I'm like I don't need

anything I'm not trying to prove

anything I'm already loved

uh by myself and others and I don't need

to prove anything. So to me it's

actually more of a game. Um and that's

why I like often kind of talk about

having fun or just like how to enjoy the

process because it's actually your life.

Um and otherwise you're in this like you

know just nightmare scenario in your

head trying to prove something and doing

so many things in the world.

>> How did you get over that?

>> Um there are many insights. sound like

people I know who go to Hoffman.

>> Yeah.

>> Did you go to Hoffman? No.

>> Okay. You sound like a a Hoffman alum.

>> Yeah. Well, I I think it's just if you

investigate that over and over again and

you see Okay. You know, I remember

raising funding the first time like the

first large um round of funding that we

raised and I started to imagine kind of

what that would look like in the future.

Well, let's say now the company is

really successful, right? or I have, you

know, hundreds of millions of dollars.

How does it feel? And I think it felt

empty. So I kind of realized that at the

end there there's nothing at the end of

success. There's nothing on that other

side that um I'm chasing and that it

actually is just right now. Like how do

I feel right now? Why am I doing you

know every step of the way if I wasn't

enjoying it at the end you get to the

end and you didn't enjoy it right? And

so just playing that forward I realized

okay what if I decide to enjoy myself

right now and um and also I took the

risk of saying that may end up leading

to the ambition disappearing or you know

not doing whatever I wanted to but I was

willing to take that risk because it

felt more honest to me. Um I think my

top commitment is to reality which I

think is a helpful commitment if you're

an entrepreneur. You need to see what

life is actually like and what is

actually happening. Um, and I committed

to that and I was like, I'll go wherever

that path goes. Just a small note

actually on the reality thing because I

often talk to people and they're like,

"Hey, I'm not getting any feedback." And

I'm like, "Life is feedback. You're

constantly getting an unbelievable

amount of feedback. I can just help you

tweak it, understand it, but if I'm the

one who's giving you feedback all the

time, it's not going to work. You know,

you're you're this is the feedback. I

feel like humans either live in the

past, live in the present, live in the

future. Founders tend to live in the

future and they're anxious about it,

>> right?

>> I think most founders are probably

anxious anxious folks.

>> Very anxious right now.

>> Um, you're not.

>> Um, I'm not. No, I at least not in this

particular way. My anxiousness is more

existential.

>> Tell me about that. Um, but I'll give

you like an insight that I had about

living in the future. Um, I was on the

silent retreat and on like, you know,

crazy things happened and I had these

like big realizations and then on day

seven out of 10, I was like, "Oh, I

can't wait to go back home and tell

everybody about all these things that I

realized and I was just imagining it and

just completely letting go of the place

that I was at." And then I realized

every time you're picturing the future

or living in the future, you're just

accelerating

>> your own time that you've got here and

you're accelerating towards death. So to

me that kind of feels like the Freudian

death wish where you're just like

imagining something that is not here

that is going to happen in the future

and you're always there.

>> Um and then I instantly kind of had this

felt experience of

>> it's a very Buddhist thought living. It

>> is a very it is a very Buddhist thought.

be calm with yourself

>> and it it but I actually

>> I bet no CEOs are like that except for

you.

>> I actually think so. The funny thing

>> Jack Dorsey probably

>> yeah there's a lot of CEOs that have the

or like come to these thoughts at

different moments. It's I think it just

depends when do they come to it by the

way. Sometimes people come to it after

they sell their company or you know you

have a lot of star athletes who are

Olympic athletes who are like after

they're done they come back and

recognize this but I do think a lot of

people actually

have some forms of these thoughts. It

doesn't mean you it means you have

clarity of mind for the ambition for the

future thinking. But what I experienced

then was a felt experience of what it's

like to actually be there and then being

really grateful for the boredom where

I'm like, "Oh, wow. I'm so grateful to

be bored because I'm here." And then I

try to carry that with me. Um I I think

it actually leads you to make better

decisions that are less rushed, less

confused about like the nature of like

what's happening.

>> Do you dip back into this? Do you

meditate? You have a practice every day?

>> No. So that's the interesting thing. I

used to have a practice every day when

things were more challenging. Um

>> we'll get into that.

>> Yeah.

>> Um I find that I come in and out of it,

but you know, again, like some of the

thoughts that I've come to are like the

the end goal of that is to really um

merge it into your day-to-day life. And

so the practice is remembering it when

you should be anxious or when something

is going wrong. So I'm like, "Okay, I'm

practicing it right now." Um, and the

goal I really what I really like about

some of these traditions is that at the

end they're like, "Here are all these

tools." And then at the end they're

like, "Drop the tools. There is no there

is no path. You know, I can't teach you

one way or another. You just have to see

what it's like by living."

>> I've met with you a few times, but I was

on the Skoya team.

>> I'll tell you my reaction.

>> Yeah, please.

>> I was negative on it. Yeah.

>> And I was like, Kareem's not motivated.

He's too laidback. He doesn't have a

chip on his shoulder.

Um, and Alfred Lyn at Sequoa gives me

crap for this still. I had obviously had

it wrong. Um, do you think a lot of

people read you wrong that way?

>> Um,

>> you had a narrative that was just like

flies in the face of the narrative I had

about what a successful tech founder

looks like.

>> I think I'm doing it on purpose. I mean,

I'll just say it. It's uh I but it's not

not to like rub people the wrong way or

to like push it in their face, but um

one it's probably just like my nature is

a little bit contrarian. Like I find

when everybody's doing one thing, it

stops being appealing. I'm like an indie

person probably versus a pop person. But

also but and and and I was worried about

that for a while. I'm just like am I

just trying to is that just a way of

generating being noticed? But um when I

when I've been in situations where I

feel felt kind of like aligned with what

people were saying, I've actually been

okay with it. So I've proven to myself

that it's not just a bit. Um

>> there's a little bit of a bit though

>> there for sure. Like it's nothing is one

thing or another. There's a little bit

of a bit. I

>> I try to catch myself when I'm enjoying

it too much and rein it back in. Uh but

there's a little bit of a part that has

fun with it. I think that the dominant

narrative around how to build things um

one doesn't really appeal to me. I don't

think it's the only way. I also think it

creates a lot of damage that isn't being

seen around and it's just like is this

actually better for the world? Is this

>> what do you mean by that the damage?

brought that up twice

>> like basically take take something like

hey the only way to build is 996 blah

blah blah right um and it's like what

does that do to people who only see that

and and like new people who have no idea

what works and what doesn't are just

copying whatever other people are saying

um and by the way you need to work

extremely hard and in fact I've been

working extremely hard for extremely

long and the I just value consistency

for example and what I found is is more

useful. And I found that you need to

tell a story that is actually like

honest to where you're at and what you

need to do. And and sometimes you do

need to work 996, but to me that was

like, well, maybe you don't have a moat

or maybe you need to do something so

extraordinary, right, that it requires

that sacrifice from you and everybody

around you. Um, but a lot of the times

it's just performative. And what does it

do to the people that are in this

situation, right? and what they force

their employees to do and then what they

you know pass on to the next generation

of founders and how they build. I we

were just looking at this case study uh

and the these are kind of like rough

unfiltered thoughts but when you look at

a business let's say you look at Apple

>> I actually think it's interesting you're

here in Boston because you're at Harvard

Business School for McKenzie two-day

deep dive for

>> right yeah

>> scaling companies I think it's

interesting you took two days out of

your schedule to do that

>> yeah I I thought that was interesting

too

>> why it's like you don't have you don't

have a lot of [ __ ] going on

>> um

>> Verun's doing everything

>> he's he's amazing yeah Let's make him

CEO. Um,

everyone. So, I did one at Stanford a

couple of years ago with Veroon and uh,

initially we were super skeptical, but

it was super generative actually for us

mainly just taking the time together.

Um, and occasionally one I roll the

dice, but two,

um, I find that when I'm in a space

alone and being fed information, then I

get a lot of like ideas. So, it's it's

mainly for me.

Um, and it especially like I'm in like a

little room alone, you know, there's no

distractions and I think it's a

important time right now to like think

clearly, especially about, you know,

what is your value prop? Like what are

you really doing? Um,

>> I think it's it's kind of funny to me

that a lot of times what you think

you're doing is not actually what you're

doing or what customers value. Like for

example, take Dualingo,

>> right? Um, is it really teaching you how

to learn a language? I don't know many

people that have fully learned the

language from Dualingo. Or is it kind of

like a edutainment game? Or is it maybe

a motivational thing that helps you kind

of remember that you want to learn this?

Here's a little bit uh or maybe it like

helps you stop being anxious. I've seen

a lot of people just needing to do it to

calm themselves down. But if your

company thinks that they're really

teaching a language, then you would make

certain choices that are different than

if you think it is a tool to kind of get

you excited about learning some new

material at a basic level. Um, anyway, I

think you should be really clear about

what your company actually is doing

versus what you want it to do or think

that it should do versus what your

customers actually are getting value

from. And those things need to align.

I'm going to come back to some of this,

>> your philosophies and you're kind of

like a CEO monk to me.

>> Um, but just to give the audience some

context, like you've had a it's an

unusual journey. It's people call it a

seven-year overnight success. You kind

of wander through the desert for a long

long time and then you found product

market fit and it really ripped. There's

a lot of founders who are going through

that desert. U let's call it you did it

for five years.

>> Yeah.

>> What was that like? Why didn't you give

up? Um, well, you heard earlier I'm

incapable of giving up. But

>> I did, but you you sold businesses

before.

>> Yeah. Well, I thought I mean that's

right, but I was much that was just like

my first attempt. And I think I learned

one that was a mistake. Wouldn't want to

do that.

>> Okay.

>> Um, and number two,

I think you need to keep going at

something to really, you know, uh, well,

you shouldn't keep repeating the same

things. That's usually the door is right

next to you. Um, but I I have this issue

actually even with people at the company

where you know you're doing something

for a year or two, suddenly it gets

boring for example or you think you've

mastered it or you're like I should go

to this other company and like lead this

thing but you're just at the cusp of

actually getting to the point where it

gets interesting

>> or you're not.

>> Or you're not. But the difference

between those two things is very hard to

tell. Yeah. And you need to often push

through that. The hard part is the part

where you think you're getting bored or

you think, you know, because you you you

give yourself a lot of I actually called

it like um this is feeds into your monk

idea, but like the devil is a shape

shifter, you know? So, it's kind of like

the thing that's whispering in your ear

like, "Hey, it's it's actually your

board or this thing isn't aligned with

your interests or you should do this or

that." Those are all different ways of

procrastinating um and not facing the

hard thing. So one you need to give it

enough time to tell yourself for sure

was it actually

>> five years is a long time.

>> Oh yeah. So well back to the five years

is not that that there was I think the

five years was a combination

really of us.

It was a spiritual journey. I like that

you call it the the long you know the

strange long trip. a long strange trip.

>> You have you've had a very long strange

trip.

>> Yes. Um it is a very long strange trip,

but for me it was actually mostly around

um deciding and committing to what we're

building. Like we had a lot of really

good ideas. We did a little bit of each

and a lot of them have actually become

companies and I'm friends with the

people whose companies they've become

and all of our analysis of them was

correct. We're like this is what's going

to happen. It'll stop at this point

because of this. But then you get into a

place where you're like, okay, what's

Especially with venture capital, you're

like, what's the biggest thing that I

can do? What is the most impactful thing

that I can do? And I think if your

ambition is really big, this is one of

the pitfalls that you can fall into

where my co-founder and I were like, no,

we're trying to do the biggest thing

that we can do. And so we would keep

changing it to be like, well, if we

pointed here, it would be even bigger.

Meanwhile, stuff is happening in the

market, so technology is changing. So,

we keep being like, "Oh, now we could do

this even bigger thing." And at some

point, I was like, "It doesn't actually

matter. I'm not trying to do the biggest

thing. I'm just going to do what is

available right now in front of me and

commit regardless of where that goes."

Um and so the you know like yes it's

five years but really there was like two

years of us building two years of us

kind of being confused and then we kind

of decided and rebuilt a few things and

committed and then we started seeing

kind of the the results immediately. It

just took some time for everybody else

to hear about it. Uh but once we

committed it almost worked

instantaneously. I kind of think of

everything as like you're going along,

you're making a it's a dip and then you

come out the other side, right?

>> But sometimes not a dip. Sometimes it

just keeps going, right?

>> Did you have doubts

>> uh that it might keep going and people

and did people around you say like what

are you doing? You're really talented.

You could be doing any number of things.

>> Uh yeah, tremend tremendous doubt for

sure.

>> I think people were Yes, people would

say that. But, you know, I would say

that people typically, especially like

me and my co-founder Nikolai, like were

like they thought we were the some of

their smarter friends, right? Um, and

felt like we should be able to do

whatever we want. And so, um, when we

were in that loop, it was also like

painful because we're like, hey, we know

that we should be able to do this.

Everybody else is telling us that. And

in fact, we have a lot of signals like

we raised money. we have when we talk to

customers they're really impressed so

what is the actual problem like why

isn't it working um and that took a lot

of introspection but I also think that

um like at some point I I feel like we

identified what the issue is around like

commitment and deciding to do something

um and I've said it in like other places

like I I think I realized okay there's a

lot of stuff that people don't talk

about in building a company they just

say it's hard. But what is actually

hard? Like in this case, what was hard

was having the courage for people that

are perceived to be a certain way or

smart or whatever to be like, "Hey,

we're just going to pick this thing. I

don't care how silly it sounds. I don't

care about the shame if it fails

publicly. I don't care actually what you

think about it." Uh, in fact, when when

I decided to commit, I stopped listening

to everybody. I was like, I'm not

listening to you. I'm not listening to

my customers, by the way, who are wrong

uh about what they want or h how if you

listen to the wrong people at the time

when it's like a small idea, you kill

it.

>> We didn't listen to customer like the

first seven years. I was the customer.

We just blocked out what they wanted. We

built what I wanted and then we flipped

it and it became a serum company and

we're very customercentric now.

>> I think companies founders are talking

about just focus on the customer.

>> I don't think that's right a lot of

times in the early days of a startup.

Well, I think it's like

>> because everyone can do that.

>> Yeah. Well, let me tell you what I think

about this because it's like if you're

like, you know, it's like in computer

science hill climbing, right? You need

to pick the right hill and then

listening to customers is kind of

fine-tuning it. Yeah.

>> But also I think the reason people talk

about listening to customers so much my

sense is as the company grows you start

to have your own kind of like dynamics

that and it's a reminder to hey it's not

about what you know I tell people it's

not about what Kareem wants because I I

I don't want you to listen to me. I want

you to do the right thing. Right? So and

my what I'm telling you is a proxy to

what I think is the right thing. But if

I tell you to build a feature and it's

the wrong feature and you think it's the

wrong feature you and you know what the

right feature is then what I want is

Clay to succeed. I don't want you to do

what Kareem so you know people had to be

reminded you can't use Kareem told me X

as an argument to do something unless

there's only very few times where I will

tell you 100% this is what I need you to

do.

>> Okay. I went to a presentation that Elon

gave once and he did this thing where he

drew all these vectors up and they were

all different sizes and they were

pointing in different directions. He's

like, "The magic behind my companies is

I just get the darn vectors aligned,

right? Have the strongest ones I can and

when they're perfectly aligned, things

hum." How in your world do you get the

darn vectors to align or you don't care

that much about it? No, I think that you

that is the generally right sentiment,

but I think there's many many different

ways to build a company, right? And it

depends on what it is that you're

building and the conviction that you

have in that, right? So sometimes in a

lot of these companies there's like a

master plan and it's like here's where

we're getting to, here's step one, fill

in the blanks, right? And this is we're

aligned here. Um I think a lot of times

you discover things as you're building.

So for me, I think there's two different

time periods. there's a period where we

don't know exactly what's going on and

we people closest to the problem might

have more of a sense and then when you

hear it from them for me I would say one

of my like superpowers is when you tell

me something that I think is capital T

truth I hear it and it sticks you know

>> it's loud

>> yeah it's loud and then when I repeat it

to other people they remember it we're

there so once that happens then we align

everything towards that and we're super

clear so there's periods of of like

total alignment everybody's pushing in

the same direction. This is the singular

goal. And there's other periods where

you need some slack. You need some like

ability for people to make choices and

you need to know which one you're in.

>> Okay, let me just stick on this for a

second. Verun talked about how you

operate very well in gray situations,

ambiguity, uncertainty, and you value

that in employees. What I found is when

things were very gray inside of HubSpot,

things slowed down,

>> right? And people would say, "You need

to clear the fog." They literally say

that to me. And I'd be like, "Okay, we

have to there's four decisions that need

to be made." Or typically there's one

big decision we need to make. Like,

Brian, you need to make damn decisions

so we can break all these ties and move.

>> So, I was a little bit more I was like,

I let it get gray, but man, the black

and white really helped us move.

>> I actually agree with you. Um, I really

value nuance is what I think he's trying

to say. And so, you know, sometimes

there's a decision and you know the

decision but you're not making it and

you need the courage to make it or you

don't have enough information or

sometimes not making a decision is the

correct decision.

>> But it's more about the clarity of you

if you know what that is and you're just

avoiding it or maybe it's a really hard

call and you don't want to make tough

trade-offs.

>> Yes, tough trade-offs. You don't want to

do it, right?

>> So, I think if you know that, then you

need clarity and you need to make it

happen. This is kind of like what I tell

people around this is we all create, we

all love startups. they're doing new

things and then as it becomes a big

company now we hate the big company but

the way it becomes a big company is

through this you know somewhat of a of

like the path of clarity the generative

phase is messy so I'd say that like I am

capable of holding that mess and

>> two contradictory ideas in your head

>> and are not I would ask people to do it

and they do it for a little while and be

like that I don't want to do that

anymore

>> because it because it's extremely

painful

>> it hurts their Yes, it hurts their head.

It's it's difficult. It requires

difficult conversations. So, I don't

think everybody can do it, but I do

think that um the more you trust people

with that, some segment of them will

value that. And I remember like being an

employee and I would have valued that.

>> Yeah. Okay. Just going back to your

seven year five years through the desert

in your two years at some point you said

this one you had a very broad vision and

then you're like this one use case going

to work.

>> Yeah. and you picked it outbound sales

marketing whatever you want to call it

go to market engineer eventually did

that kind of hurt you that you had this

big broad platformy thing and then like

we're going to really n like narrowing

>> yeah that was very very difficult and I

I'd say that um well I'll say two things

so one is that um you know it's

interesting that you perceive me as this

or like people perceived me as this

before my friends actually in the past

perceived me as extremely aggressive

really intense and people can't even

imagine that right now. Um,

>> I find you intense,

>> which I still am, but it's like

contained um, and directed and hopefully

like more, you know, something that I'd

like to open up when necessary. Um but

on the on the point of like picking so I

would say that um it was actually my

co-founder Nikolai who identified this

segment and use case and I was finding

it very challenging to commit to this

and I think he was too because I'm like

how is this related to like you know we

wanted to give the power of programming

to more people

>> and that still lives on in the fact that

we called it go to market engineering

and to like the idiosyncr ratic way in

which like all the features are built to

give you that like maximum power and

flexibility, but we would yo-yo between

kind of like maximum power and

flexibility and hey, it should just work

out of the box simplicity. And at some

point we're like okay, let's just commit

um

>> power and flexibility

>> and to the power and flexibility which

was the exact opposite of what everybody

believed would work and what customers

said like I'll give you people everybody

has copied this waterfall enrichment

concept, right? Um, but you know what?

If you talk to customers, they're like,

"Listen, I just want the number of

people that work at a company. I don't

care where you're getting it from. I

just want to wave a magic wand and do

that." And my my argument has been like

once the technology is there for that,

we will do that. But at the moment, the

best technology is put everything

together, give you transparency, and

speed up that process. That's what

actually solves the problem. You can say

like, "I want to go from New York to

London in like one hour, but I can't do

that for you. So what's the next best

thing?

>> Yeah,

>> we have a couple things in common

between the companies. We very early we

said we're going to create this category

called MM marketing. It really worked.

You've done the same thing with go to

market engineer. It appears to be really

working.

>> Yeah.

>> Everybody in their brother asked me how

to create a category and there's a

little bit of magic in it.

>> Right.

>> Can you talk about how you did it, the

decision on the name, how you propagated

it? Advice for so many founders who want

to do this. You know the common advice

about this is don't do it right and it's

very challenging which it is. I think

>> you I don't think you can create

necessarily a category. You can take

something that is happening and name it.

>> That's what we did

>> right and then give it uh like put a

circle around it. Be like here give it

some fuzzy boundaries which is

important. Um and then allow something

that's already happening. It's kind of

like a wave and you're like okay I'm

going to name this wave. I'm going to

give it uh credibility. But for us, the

way you know we did it was uh one we

started noticing people use the term GTM

instead of sales in the most

forward-looking organizations and the

ones that would adopt us. So we decided

to use that and then we were like well

what are they doing? there. We used to

have like a term called customer

engineer where it's just like it's kind

of like forward deployed engineer and

we're like what what if you actually the

best categories I think are like two

words stuck together right um because I

think language is evolving like imagine

if you had like uh Roomba what would you

call it before you invented like a

vacuum you know it would be really hard

to name it

>> y

>> who came up with the name and when you

came up with you're like we're going to

create a category around it or did it

just sort of started happening?

>> No. So Verun and I were chatting about

what we should call our own people who

are helping customer fine

>> and then I was like let's just call them

go to market engineers

>> as opposed to now they might have called

it forward deployment engineer.

>> Yeah. Or customer engineer but we wanted

it to be unique to our thing and and

actually credit to uh Mike Rol who was

one of our early investors. I would meet

with him and he'd be like we should own

a title. And I was like, well, how are

we going to do that, you know? And so

when we were like talking about this,

we're like, okay, it's go to market

engineer. Let's call our own team go to

market engineers because they're helping

you think about your go to market in a

systematic way. So basically, I think it

needs to connect to some of the core

assumptions about your product. So if

you think about clay, by the way, um

most of the decisions are obvious. So

this is where the clarity is important.

I I think people get really confused

when they hear me say like you should

live in ambiguity all that stuff. There

are certain things that need to be super

clear and living in the ambiguity allows

you to one day get to the clarity. So

for us some of the decisions that we

made that are super important are we are

going to be for a technical user. We're

going to call them the goto market

engineer. We're going to be the most

powerful and the most flexible. We're

not going to own the data. are going to

be a data marketplace and we're going to

charge in usage and not seats

>> clear

>> right now those decisions do not change

and have not changed and actually if you

look at the product all the decisions

are super clear if you go back to that

and we're like hey does it make it more

powerful does it make it more flexible

over simplicity one of our things is

power and flexibility over simplicity

not because we don't want it to be

simple but when they conflict we give

you power because it's a technical user

Now we can also sell it to you in a

particular way. Uh and it was super

important for me for it to be PLG by the

way. That's another reason why it took

so long cuz this is a very difficult

product to make it usable use and PLG

typically don't fit

>> right um

>> or not hard to use but powerful.

>> Powerful. Yeah. And so needed to be a

type of customer who can pick it up and

hack around with it. And then the usage

based meant I really like this thing

that I I think I was reading something a

long time ago around like Hegel's like

idea of like thesis and antithesis and

then leads to synthesis. So that's like

how it's like a theory of history. And

then there was this guy Furbach who's

another philosopher who was um also

talking he kind of flipped around his

whole thesis and was like you know

Heggo's thing is like we're going

towards God or gist or whatever and

Furbach was like actually we're already

like the complete thing and we are um

projecting like the idea of God is like

our own projection of our own misgivings

and things like that.

>> Wait, what's this got to do with go to

marketing?

>> So let me let me bring it back for you.

But this welcome to my mind. Okay, I

like it.

>> So to me the interesting thing, this is

more of a like fact that I think is

interesting, but the interesting thing

is like taking something and then

flipping it on its head is a great

technique for innovation and then taking

that thing to its natural conclusion. So

you can, you know, in philosophy you

would like study these two theorists and

like look at their ideas, but it's the

same thing here. It's like, hey, what if

we took everybody told me that you

should sell to salespeople if you're in

go to market um and it needs to be super

simple and it's seat based. Flip

everything around, you have a new

product. Right now, is this a better

product than the old generation of

products? You have to have a thesis

around that as well, which we do. Um,

but I think that's kind of the approach

that I took at the time that helped us

make all of the other decisions later

easy.

>> Fell out of it.

>> Yes. the name how did it propagate?

>> Um so you called your folks JTM

engineers.

>> Yeah. So the go to market engineers this

is a I think this is very subtle and

very tricky right because if you go out

I think you guys did a different thing

where you were like we are going to like

go out and talk about this and we did

something very similar like there was

SEO and blogging and all this stuff and

we said that's inbound marketing and by

the way what was good about it was there

was an enemy. No one liked outbound

marketing and outbound marketing was a

word inbound wasn't

>> right.

>> But we just flogged it like we wrote a

book, we wrote articles, we did a

conference.

>> So we took the exact opposite approach

and again yeah which is like don't I

mean some people don't even know that we

came up with this right?

>> It's kind of like you need to think of

concentric circles that it's going to

evolve. So we talked to agencies

>> who are already doing this work and uh

we started talking about how our own

team is called go to market engineers.

they started adopting it because it was

a cool term and showed up on their

LinkedIn and then they uh we we

basically empowered them with all the

information all the things to make them

more successful and look good and

because they needed business. So here's

a big

>> this is the same as us like we educated

and we gave them everything they needed.

Yes.

>> To create an inbound marketing agency.

>> Exactly. And the only part is that we

try to not take credit for it or be

involved in the conversation and we

leave the conversation open and this may

be part of the ambiguity thing. So we're

not like here's what a goto market

engineer is. We're letting the market

evolve and it's actually broadening as

it should. You know if you're using

claude you're a go to market engineer.

Go to market engineering and why I think

the category is a category is that it's

a point of view on the world. It's not a

technology. It's like how do you run

your go to market team where you build

tools where you test hypothesis and then

with AI it makes all of that much much

easier since code is cheap right so um

first the agencies but you needed and

again obviously you know this because

it's like agencies need the work so

they're going to be if you were

targeting companies no one wants to tell

you how they grew in fact you know our

new kind of internal tagline for clay is

go to market infrastructure to grow in

ways your competitors can't. That's the

whole point of it. It's like how do you

do something that no one can copy,

right?

>> Turns out people are followers,

>> right? But the thing is um that's why

you need to build a system that you can

update quickly because it the just the

path to people copying you is going to

be fast and you need to understand your

business well enough to come up with the

next hypothesis or AI needs to

understand your business well enough.

>> Okay. So you you come up with a clever

name,

>> right?

>> You called your people that you started

educating the agencies on it. They like

the name. and they started using it and

it just sort of slowly spread. Is that

kind of

>> it's how you did it?

>> I would say it quickly spread in certain

areas and then we provided some

scaffolding around um like we published

a couple of articles but we tried to

stay in the background of this.

>> Yeah.

>> Um

>> we did not we were competing with

content marketing at the time.

>> Yeah.

>> And so we were aggressive with it. We

didn't want to lose that kind of that

makes sense. Yeah.

>> Yeah. Um, I think the main thing is that

we came up with a I don't know if you

guys thought about it as a title or a

category. We thought about it as a title

and I knew that one day it would be the

category.

>> We didn't think of it that way. We

thought of it as like a new way to go, a

new way to market,

>> right? So, so that

>> yours more a title. It was different.

>> Yeah. So, we thought about it as a title

and we wanted the people to call

themselves that. And so, we were focused

on that. And then the idea was that we

earn the right to call it a category.

And by the way, I think time really

matters in all these things. It's the

storytelling. So if you go too early and

start telling the story, in fact, people

push back against you. Uh so you need to

pick the moment where there's so many

people who are invested in this. You

know, we had our own community round. So

there are people who we've proven. And

by the way, we have like organic. The

other thing that we did that's super

important by the way is we have clay

clubs in over like 80 places in the

world.

>> We played these same games. They worked.

These things worked. just help them.

>> Um, but but the key thing around that is

like now that people have actually made

a lot of money from it and that it's

helpful to them,

>> you call it the category and it's

important that the category is bigger

than you. That's I think the last piece

that's super clear um and continues to

evolve. Right. Another thing you have in

common with HubSpot is the whole agency

thing was the sec. We started as direct.

>> Yes.

>> And I was the first salesman. Um, and we

were quite good at it actually. And then

we had this one sales rep named Pete

Capuda.

>> And

>> great name.

>> Yeah. And he and we had a lot of

agencies interested. And I remember it

was like two, three years in I was like

the product's not ready for someone else

to sell it. It's not mature enough.

>> It's like don't call on them. But we

also had like like a weekend you could

you could do anything you wanted on the

weekends or after hours. It's kind of

like Google's 20% done.

>> Yeah.

>> And one weekend he started calling on

him and you can just look at the in the

histogram of the numbers and it's

typically a bell curve but he was like

4x the next month in revenue. I was like

I guess Pete was right. And then we

started building a whole program. It's

like a separate company to engage with

these people and take care of them.

Yeah. How how did that happen to you in

advice for people who want to create an

alternate? So many people come to me

want to create a second channel and it's

very hard.

>> Yeah, it's very hard. I mean and we it's

you know I don't know that we've fully

cracked that but I think that um

>> I would say like a big part of this was

Verun as well like we were in WhatsApp

groups with people who own agencies. We

we I feel like the the the answer that I

think people don't really want to know

is there's there's no playbook. We were

being honest and genuinely authentic.

The mission is how do we help companies

grow and we're like we're going to help

you grow no matter what. Back again to

some of my pieces around like how I was

operating. I was not operating and maybe

you were reading this correctly. I'm not

like I am trying to make Clay

successful. I was like I'm doing what I

think is interesting and I hope that is

aligned with what makes Clay successful.

I'm interested in that. uh but actually

I want to make these people successful

and they felt that genuiness and we did

really crazy you know Verun he's he's uh

I think he was talking to someone on

WhatsApp and the person was having

trouble fixing something on Clayton he

was like I'm coming over to your house

right now and the guy was like don't

come he was like no I'm coming and they

became really good friends

>> so we built

>> genuine authentic friendships with a lot

of the people and some people left their

job to start cleances

Yeah. And we were just kind of on that

journey with them. Uh truly.

>> Yeah.

>> I think if in our heads

>> we were thinking, hey, we're trying to

create this category and we need them to

do X, Y, and Z. People are very good

people readers, by the way, and they can

read your intention. Um similar to VCs,

right? That's their top thing is they

can read your intention. So if you're

going to go there and fake confidence,

that's not going to work. You need to

truly believe that you have the magic

sauce.

>> Another thing that everyone's coming to

me asking about is pricing and you guys

announced a pricing change. You caught a

bunch of heat for it and you responded

in an interesting way. All CEOs seem to

go through like getting punched in the

face by the market and you just you just

kind of got punched. Um I don't actually

care that much about the pricing. Talk

about the backlash to it and talk about

what you did and kind of your philosophy

around it. I would say the backlash is

minimal or at least we perceive it to be

minimal. We did

>> loud to me,

>> right? I think like we did a bunch of

like analysis around like sentiment

analysis on some of these things and

we're like it was like 70% neutral, you

know, somewhat some negative people and

I think all the people that were quite

negative or loud about it had some

self-interest. Uh so, you know, they

owned something where it would benefit

them for this to not work. um we haven't

seen kind of that negativity show up in

the numbers. So that's another way in

which I know but the the way that we

dealt with it

>> I think that's the interesting part.

>> Yeah. And you know I don't know there's

like a huge backlash against Ferrari's

new like electric thing. And by the way

I was reading there was a huge backlash

when they had their SUV which they don't

call an SUV. It's an FUV or whatever but

now it's completely sold out.

>> Okay. Um so anyway that back to like our

pricing change the the things that help

us withstand something like that is like

one what is our conviction in our

thinking right so we're like hey we

bundled like credits credits cost data

and whatever we act what value we

provide and we were big enough at this

point to and thought that we were well

known enough that we can break it up

into two axes and then make it so that

it's clear where what you're paying

where and also make it cheaper

>> splitting splitting compute and

splitting the data.

>> Right. Exactly. Got it.

>> And so now that we have compute and data

um and we trusted the sophistication of

our like um customers to eventually

understand that um and also understand

that it's truly in their benefit like we

calculated it and we're like this will

be cheaper for you on the short term and

on the long term we should all make more

money, right? But the other thing is

that we were absolutely transparent in

our document. Um it couldn't be more

trans. literally was word for word what

we were saying internally in our

meetings. Um and that's a common thing

for us in the way that we operate and I

think maybe unusual and surprising to

people.

>> Yeah. It disarms them.

>> Yeah. And it it goes back to this

>> equals trust. It's not even correlated

with it's like equals it.

>> It equals trust.

>> And in order to do that, you need the

right channel. You need to be talking to

the right people. Otherwise, the

transparency could actually be damaging

to you. But I think that's like where

the nuance believing in nuance and that

even though everybody wants you to speak

in bite-sized pieces, we're like, "Hey,

we're going to actually show all of our

work even though it's long." Um, and

then other people will actually read it

and digest it.

>> Yeah. I I I thought that was very well

handled. Um, I want to kind of shift to

kind of you as CEO. What's your day

like?

>> Um, I have like two terms for it. One is

I'm a momentum detective, right? And so

I just go around the company and I love

this.

>> Yeah. I find momentum is so hard to get

if you lose it. And so anytime you see a

area of the company losing momentum,

that's where your focus should be

because sometimes you just need to

grease it and then it keeps

>> Oh. So you don't hop on where the

momentum's hot, you hop on when it's

starting to wayne.

>> Yes. So well, it's both, right? Um you

want to know the places where it's hot,

but often those places don't need you.

What is the unique thing that you can do

as a CEO, right? I'll give you a couple

of examples of things that for example

I've done that created momentum and then

places where I've like kept the momentum

going but

>> you know the go to market engineering

right like getting that right and then

you know we had Mishi and Verun write

that article but like getting that and

putting this is what we're doing push

through with it and then we came up with

this concept of go to market alpha I was

talking to a friend of mine and we were

like hey this is the term and then I

went back and I was talking to a couple

people, it resonated with them and we're

like this is it. Now we use this in all

of our uh like and you know people

initially were like alpha that sounds

like really nerdy you know

>> the customers are nerdy

>> right but or just like it's too fin and

I'm like people will get it from finance

you don't even need to know as soon as I

say it people oh yeah you need to have

some competitive advantage but it's a

better word for it

>> so we have a couple of these things

where every once in a while there's one

idea that generates momentum um I'll

give you another idea we needed a

feature that we call audiences which you

you know, allows you to have like a

concept of a company or a person in the

product so that you can aggregate

signals on it. Um, and it's backed by a

CRM. So, we're not building a CRM. It's

backed by that. But to get that going in

the company was incredibly challenging.

You know, people are like, "What about

our tables?" Well, like we don't want

this to have table limits, no row

limits, no cell size limit, a lot of the

limits that we just remove it. So, I had

to motivate it in a different way. um it

wasn't getting traction which is kind of

interesting uh but it was I had to

motivate it by saying okay we need

signals which is we already have data we

need data changing over time and so

let's build signals that was okay people

got that and we then were selling

signals and we started beating companies

that only sold like job changer signals

then the team themselves realized well

what if you have five signals what are

you going to aggregate it of well you

need this concept of an audiences which

we were talking about before Um and that

like you know I think it's kind of again

the storytelling I should have been

telling that story before but like

leading the team so that they believe

themselves and they have the momentum is

very different than me being like you

need to build this feature even if so

one of the things I think you realize co

is that you are sometimes way ahead of

everybody else

>> because you're getting input from so

many places not just because you're

smarter or whatever it is but you're

just getting your purview is larger and

that's all you're thinking about all day

and you have an intuition for this that

you've built over time because I've made

a huge number of mistakes everywhere,

but I've also been doing this for so

long.

>> Yeah. Momentum detective. I love that.

Right.

>> You're good at branding, by the way.

>> Apparently,

>> all your cliences, all that stuff.

You're very clever at it. Uh you've got

kind of two modes.

>> Yeah. I I think there's the there's that

one and then there's really it really is

mainly around like people are in some

kind of you know funk and I remove that

u

>> advice on how to do that for other CEOs.

Um, so actually my head of people told

me that I'm uh the only CEO that she's

worked with that has apologized and I

would say that that's one very helpful

technique. Like someone was telling me

for example they had they had like a

bunch of problems, right? And it was

like there are many there are many

problems that seem like they're the

problem but often if you listen and

apologizing doesn't mean necessarily

that something you know that the whole

organization is wrong. It might be that

we didn't listen to you or we didn't

treat you in the way that made you feel

respected. And once that calms down, we

can then deal with the actual problem.

Um, and people are very sensitive to

that.

>> Just very tactically like your day, do

you leave a lot of open time to momentum

surf? Um, are you packed every half

hour?

>> Um, it goes in phases. So most of my

days for a very long time were packed

like every 30 minutes, every 20 minutes

and it's complete um context switching.

So you know it's recruiting product

decision making listening to someone

removing a problem comp issues um you

know talking to partners those

>> all the things

>> all the things and then once I do that

for some period of time um typically you

know typically if that happens too many

weeks in a row I need to stop delete

everything and leave a ton of space. I

prefer like we run the company in um

just in time decision- making. So like

some unusual things that we do uh which

we will eventually introduce but not yet

is we don't have an exec team meeting

which I think people find bizarre um how

do you stay aligned all that stuff we

call we have open space call me whenever

um and then we resolve it otherwise

people wait for the meeting as you know

um but yeah I think that the open space

is my preference and the other way where

everything is packed works but is

typically means things aren't like

people don't have the information for

them to make distributed decision-m and

I need to control everything in order to

make things work but it's exhausting and

you can only do for sometimes it's

necessary but you can only do it for you

know months at a time

>> and where do you get your think time in

or like I want to go really deep on and

build an agent for myself like where do

you how do you fit that in is that

weekends or

>> kind that has to be after work weekends

etc but I also like I would say I'm

unusual in that my thinking like for

example I go out dancing with my friends

and I'm thinking and I'm also talking to

them about it and so I'm I tend to like

movement actually and doing things or

you're on a hike those are helpful um

but again like I I sometimes I actually

think again this is maybe

counterintuitive but like you don't want

to look at something directly to see it

you might want to squint at it because

it's too much so I get information

through other people um and then process

that and then come up with a decision um

rather than you you can't just rely on

like your firsthand experience of like I

you know I built a lot of the initial

product uh with my co-founder so I I

remember everything about it but I try

to make decisions now without needing to

you know like if someone tells me

there's an issue with a feature I can

simulate it in my head and use I don't

need to like play around with

and with kind of like let's say playing

around with LM there's so many people

experimenting and trying to soak that in

the firstirhand knowledge is limited.

>> Do you have one-on ones or you're like

yeah what do you think about that? How

many direct reports do you do one ones?

>> Um so the

>> these are just tactical things

>> people ask me all the time.

>> So

um right now I probably have seven

direct reports. I've been limiting I'm

actually just so I I've I've gone back

and forth. Um and I'm trying to put

everybody in the same meeting and have

like one-on- ones once a month. But

again,

>> we did exactly that for our first five

years.

>> Yeah. Go back to just in time

processing. Just if you need something,

come to me is the easiest way. But I did

manage the whole engineering team up to

six 70 people.

>> I see.

>> Um without a head of venge until last

September.

>> Okay. That was a lot.

>> Yeah. So I tend to and just through the

managers, but I had like pretty much a

direct relationship with almost all the

engineers because I I wanted to keep

that

>> stay close to it.

>> I didn't do one-on- ones for the longest

time and then I did one-on- ones every

week. I really wish I didn't.

>> Yes,

>> it's a little so they're they can be

draining.

>> Very draining.

>> Where are you on that?

>> Um I think that it's draining. I've

removed one-on ones. I I have one-on-

ones with so now actually my new one-on-

ones are with people that are not

reporting to me where I'm like these are

top priorities for the company. So I

have a one-on-one with our head of sales

because I'm like we need to stay

aligned, right? Um if there's an uh a

thing where we're like doing some new

project, I'd rather have one-on- ones

with that person. Um, so it's I'm trying

to do it actually with in places where I

feel like the reason I have it with our

head of sales is our sales team is

growing so tremendously and I'm the

person who's the like communicating the

culture and I want to make sure we stay

aligned and then any issues can be

brought up and dealt with quickly. But I

don't need that with you standing weekly

one ones.

>> I'm deleting all of those. You got it.

>> Um, let's just talk about trust. People

used to complain to me that I trusted

the handful of people and really

overindexed on their input and sounds

like you're a person that gets a lot of

input from a lot of places and then

maybe didn't trust my trust circle was

small. People complained about that.

>> Interesting. Yeah.

>> Similar.

>> Um Yeah. So, and did you did you change

that as people talked to you about it?

>> I tried to. It didn't. Yeah.

>> Honestly, it didn't really work.

>> Trust is hard to build with me.

>> Yeah. Uh I think that I have a similar

thing. I'm not um I have like trust

issues for sure.

>> Yeah.

>> Um but it's like different I mean

there's different levels of trust. So

there's like real trust which I have

with a handful of people.

>> That's what I'm talking about.

>> Yeah. That's what what people have said

to me is that I'm too forgiving.

>> Um so I'd say I have like one one kind

of like thing that I'm trying to change

is being forgiving, forgiving, forgiving

and then explode, right? Because I've

been super annoyed. um and feel like

I've given too much. So, I'm trying to,

you know, give you tons of like I'm I'm

actually angry right now. I'm annoyed

>> uh over time.

>> Do you hold on to people too long?

>> Uh definitely. U but it has worked out

sometimes. I I keep hearing, you know,

people are like, "It's never worked

out." Um I would say that we are as an

organization, we believe in you. we want

it to work out and we're constantly

assuming the best intentions and

sometimes because you know it's

sometimes the person sometimes the

context right so you can get the wrong

with the wrong context you get the worst

out of someone um so there have been

situations where something seemed

completely off and I like listened to

this person did the exact opposite of

what everybody you know like um I'll

give you an example that's would seem

absurd right someone did something wrong

Um, and it doesn't matter what the

details are, but uh, I gave them an

increase in salary.

>> Why?

>> Right now, that seems crazy because I

>> seems like something a contrarian CEO.

>> Uh, now that person is one of the best

performing people in the company, right?

And the reason is I realized there was

it was out of like

>> structural things held them back

>> and it was out of like partially out of

the fact that they were not being paid

correctly.

>> Okay, fine. So, but it but you could

have been like, "Wow, this person is

really and you're just like ha you

shouldn't reward something when someone

does the wrong thing." But actually,

sometimes you can fix it. Okay. I heard

I've heard you or maybe everyone told me

that a company exaggerates a founders's

traits. What traits

are you happy it's exaggerating of

yours? And what traits are you like, I

wish it wouldn't.

>> Right. That's good. Yeah, I told him

that. I feel like it's a um

>> I I by the way I agree

>> usually it's like where I get surprised

by people. So I do feel like people

seem really open and enjoy working

together and it's very at least that's

the feedback that we constantly hear is

that it it people are having fun. Um and

sometimes they

>> yeah they're like you know there there's

an absurdist kind of like feeling to the

company. It feels like po I don't know

it's like a postmodern painting. you

know, there's stuff um and then

everything has its counter point. You

just need to be conscious of what it is.

And I do think like I really value

patience as can be seen by the five-year

thing. And I think sometimes we are too

patient with things um that are not

right.

>> It's not a dip. It's going to keep

going.

>> Yeah. It's not good enough. And I think

um like I have very high standards and

at the same time I'm very forgiving. Um,

and so I think that um,

>> where does that come from?

>> The very forgiving part,

>> high standards, but is that mom? Is that

dad? Where's that?

>> Um, yeah, I think the I mean the high

standards I feel like it's like taste.

My parents like have high standards. My

but and the forgiving part. Yeah, it

probably is like and my my dad is very

forgiving, but I think it also is like

um back to kind of like why are we doing

this, which I don't know that everybody

is thinking about

>> until later u the way that I'm

interacting with people at work? You

know, one of the things I think about is

I I've talked about this for example at

the company, right? Uh this is like um

if you can't forgive your coworker for

some infraction or some random thing

they said to you or some like small

competitive nature thing that you're

doing, how are we going to actually

forgive people in the world? How are we

going to make this work? Um this is a

microcosm. Everything that is happening

in your personal life as a problem is

probably happening at work as well. just

at work we can give you feedback and the

you know the stakes might be lower in

some ways right um and that's why we

have like you know we try to cover

therapy we try to cover coaching we give

coaching to people who are not leaders

because often it's IC's who are going

through kind of you know sometimes

people are going through crazy cycles of

emotional things because I made some

random comment passing by or someone

said something to them and then it

really gets in their head and how much

time are we wasting on this versus doing

productive work. So on the one hand, you

can be like, "Hey, we're a company that

is trying to, you know, maximize

shareholder value and dominate the world

and make as much money as possible."

You're probably wasting a [ __ ] ton of

money by not dealing with like people's

emotions around very silly things. Um,

and also by perpetuating kind of like I

actually think what this is a pet theory

that I have is that very few people get

to this stage of company, right? Um, and

it's very when you're in it, it's very,

you know, you're kind of trying to stay

exactly on the line of success. So, you

don't want to try too many crazy things.

You want to focus on your product and

what's unique about you. And so, you get

this wisdom from other people who have

done it. And it's all kind of like we

call it couch wisdom. You know, it's

it's not really studied. It's like what

this person did before and therefore

they'll give you some advice. You will

do it and you'll get the exact same

problems that they had. So sometimes

we're trying different things. You know,

people tell me like, "Hey, you should

hire fast, fire fast." Well, that has

specific set of problems.

>> Higher slow, fire fast.

>> Yeah. Higher slow, fire fast.

>> You don't believe in that.

>> I I

>> You obviously don't. You just said the

fire

>> Yeah. Yeah. I I also think um I think

that there's a lot of moments where we

should make decisions faster around

that, but I just don't believe in these

rules of thumb that I think at some

point you shut down internally. You stop

like thinking about the situation.

You're just following the rule. What

other CEOSism do you think are stupid?

>> A lot.

>> Like

>> I think driving people really hard

uh without paying attention to like I

like for examp I'll give you one example

like people come in and they're like AI

is going to create ton of productivity.

We should lay out fire 20% of the team

without knowing what you're actually

doing. And that's what makes people like

IC's think exacts are dumb, right?

Because they're going to meetings

together. They hear some other person

did this. You just go and do it. And I

think there's a huge lack of empathy for

like the team. And I feel it sometimes

too. It's like management, you know,

it's like the principal agent problem,

management versus like workers where

you're like, why aren't people thinking

correctly? Why aren't they, you know,

taking action? Why aren't they like

owning this? Well, there's incentives

aren't aligned for that. Uh anyway, I

have I I also think that

um thinking of work, this is a big one

for me rather like my definition of fun

is very broad obviously. So like type

two fun is fun for me. Climbing

something is fun. But I think motivating

people through either just greed or fear

or discipline

um is not always the optimal. You need

you need the whole toolkit. So like you

know another word for discipline could

be

>> the fear and greed thing. That's those

are the

>> those are all levers by the way. Yes.

>> How do you think about that?

>> Um I'm I'm uh I believe in like the full

spectrum of the things. So it's like

devotion is as good as discipline. Like

you can't just use some of these tools

without understanding both motivate your

team to win but also create like a place

that you actually want to be in. So my

point is there's something about

business, this is again like some of my

own that that feels like you're just

trying to take this thing and hand it to

someone else. Like it's like a musical

chairs thing, right? So like the best

businesses I I said this at the

beginning like Apple, it's like well

who's actually doing all of the stuff?

It's like Foxcon like well here's this

beautiful business that has all the

numbers are going correct but it's

because I can squeeze my suppliers in

this way. Now, I'm not going to think

about that supplier. It's kind of like

throwing your rubbish somewhere else and

you're like, "That's in China or that's

over there." And what I'm like thinking

about is like, "Hey, we live in the

world together. What happens if I win

but you lose?" Um, it's fine. Like, I

guess you'll you can just jump off and

maybe you'll not get caught and no one

will worry about it. But I'm I don't

want to do that because I don't want to

live with myself in this way.

>> Okay. I had Jack Dorsey on a few weeks

ago. He YouTube rhyme. Um he's an

original thinker. He's not central

casting for CEOs and he's, you know,

he's laid off a big chunk of his

employees, but I think he's really

retoled the way the company works and,

you know, he's put AI in the center and

he's delegating a lot of decisions to

the center. The people are on the

outside. He's rethought his org chart,

it's compensation. He's sort of

reimagining it.

>> I assume you're following some of that.

What's your take?

>> I think that, you know, it's hard with

like public companies too because it's

like you what is the narrative versus

what's reality. I I do think that

sometimes you do need to retool the

company. Um and maybe you hire too many

people or maybe things are changing. Um

and we don't have really good ways in

general to say the truth without um co

without people

again I I really think it is this

principal agent problem, right? It's

like whatever you say is being parsed to

be like is it what you really said or

does it mean something else? Are you

covering up something?

>> I don't think he was covering it up.

>> Yeah. So that's what I mean. I'm just

like I think that you could take it at

face value and be like this is actually

what

>> I think he's actually doing the thing.

>> Yeah. And I think that's probably right.

>> And do you think he's on the right

track?

>> Um

>> like he's got two layers of like he's a

crazy flat. He's got a big team working

on his trying to make all his systems

legible. Get everything in that legible

system. his people are really

responsible for making that system as

legible as it can be and then building

agents on top of it and just turning

over a lot more of the decision making

over time to he calls it the

intelligence.

>> Yeah, it's a really hard thing for me to

comment on just because I haven't

actually thought about it deeply enough.

>> Yeah. Okay. I got a couple more just

bringing you back to the philosopher

king. You've got a line. There's no

elephant in the room. The elephant is in

your mind. I can't believe he told you

that.

>> How does that apply to being a CEO?

>> That was an off-the cuff comment, but I

I uh if I remember correctly, I have,

you know, like a Q&A

>> every every week. It used to be every

week, now it's every other week, and

it's optional and people

>> um show up and we talk about anything.

And I I think my leadership style or

communication style in general is to

call the thing out that you might be

wondering and assume that you are a

smart person. Um and not kind of like

dance around it. And so typically what

we do in these meetings is just be like

here are all the things that you might

be worried about. Well, every week

actually in our in my all hands um I

talk to people on the team constantly

um and I hear various things from them

about what's happening in the company,

how's the culture changing or not

changing and I try to bring these things

up um so that we can all be aware of

them

>> you know so one of the things

>> calling them out

>> yeah calling them out like hey people

feel like um we can't um we we're

stepping on each other's toes and I'm

like okay let's discuss that how does

that how does that manifest. What do we

want? What behavior do we want?

>> Y

>> um and I think a lot of the times

>> um

>> so you're calling the elf in the room

out. What about the elephant in the

room?

>> Right. So So a lot of the times nothing

is happening and it's just your

in anticipation of the problem

>> or sometimes uh we call this like you're

bringing baggage from another company

where something happened to you and then

you're like hey I don't trust you guys

yet. And so you're creating the problem

because you're you're seeing this thing

in your head that isn't even happening

in reality. So I'm just like, tell us

what's actually going on so that you

don't work based on some perceived

reality that isn't even real.

>> What do you want to do when you're old

and gray like me? What's next for you?

>> It's hard to think about the future.

>> But I happen to be an electrical

engineer by training and I have also

>> uh been playing more music recently. Um,

so I want to be doing a lot of like

generative ambient music. Uh, I've been

doing a bunch of stuff like that

already. Okay.

>> I don't know. There's something around

like creating soundsscapes and getting

into

uh like that place where you know you

can't really I music is all about

predicting kind of the next sound. But

I've really been enjoying this idea of

like if you can't predict it but it's

still like good. What does you're

expanding kind of like your sound

vocabulary. Okay.

>> Yeah.

>> I appreciate you coming on. It was a

wonderful conversation. Congrats on all

your success.

>> Thank you. Thank you.

>> Hey everybody, I hope you like that

episode with Kareem. I really enjoyed

the conversation. I have a lot of

takeaways. I'm going to give you my

three and I'm going to give you a couple

stories of my own that tie in. Uh two

nights ago I had dinner with Kareem and

David Solomon from Goldman Sachs and TK,

the CEO of Kshi.

And my takeaway from the dinner was,

"Holy crap, are these three homo sapiens

different and holy crap is their CEO

playbook different." And it reminds me

of an old quote, you know, I think it

goes, "Be yourself. Everyone else is

taken." I think it was Oscar Wild who

said it.

I leave that with you. I hope you can be

yourself because everyone else is taken.

There's a lot of ways to do this. I'm

trying to look for the one way. The

truth is there's a lot of ways to be

successful as a CEO. Um the second thing

he's sort of the a philosopher and he

reminded me of something I've I've been

working on and people say pe folks who