Should You Start a Company? The Honest Truth

We were constantly like, "Salesforce is

going to crush us tomorrow. Did you see

their announcement? We're dead." We said

that

>> [laughter]

>> so many times.

I'm excited to be on your show.

It's kind of our show, Brian. That's

true.

Do you consider yourself retired?

I don't think I'll ever retire. But

you're not the CEO of a company. No.

I have a whole bunch of interesting

stuff going on. Are you happier in this

phase of your life than when you were

running a 20 or 30 billion-dollar

company? Or how about happier compared

to when you were running a 10

million-dollar company? Where where is

like your levels of happiness been cuz

you've founded a company that is now

has, I don't know, five, six, 7,000

employees, billions in revenue. Now

[snorts] you're retired and you're not

retired, but you're not running a

company and you're a little bit of a

a VC and advisor.

So, tell me about your happiness levels

between each one. Okay, I'm going to

give you like the grading system in my

head of for number employees. Like two

to 10 employees, I was like a C. I

didn't really I had

I could write code, but no one wanted

it. Like I did You don't add a lot of

value at that phase. 10 to 100, I was

like an A. I felt like I knew what I was

doing. I had been in, you know,

scale-ups before. 100 to 1,000, you

know, maybe A minus. Like I kind of felt

like I knew what I was doing.

1,000 to 10,000,

I didn't enjoy the the secret of life is

enjoying the passage of time. I wasn't

really enjoying the passage of time. It

was a lot of

I was just working on a lot of stuff I

wasn't that interested in. So,

yeah. So, it depended on where I was in

the in the history of HubSpot. Like I I

had sort of CEO market fit between 10

and 1,000. That's like your your you're

putting 100 to 1,000 in the same

category. That's kind of astounding to

me. That doesn't seem like those should

be in the same category. So, you enjoyed

that whole range equally. Yeah, I worked

when I my first job out of school,

I was the first BDR at a company called

PTC. It's a CAD software company. And I

joined it was like 3 million in revenue.

And when I left it was, you know,

billions in revenue. So, I sort of saw

that journey and I was part of that

machine.

And so, you know, I took a lot of that

and brought it with me into HubSpot. And

I just felt like I knew what I was doing

in there and I was working on things I

really enjoyed. There's a lot of changes

between 100 and 1,000. I just sort of

remember being quite motivated and happy

with my day-to-day in there. Very little

worry in that phase about what the nom

and gov committee of the board thought.

Very little interaction with our

compliance and legal folks, things like

that.

>> [snorts]

>> Um mostly just working on

you know, are the employees productive

and happy? Are the customers productive

and happy? Like really focused on that.

And I I like that type of work.

Can you go through Okay, so your

categories were two to 10, 10 to 100,

100 to 1,000, and then 1,000 to 10,000.

What about how hard you are working?

Like in terms of hours. You know, people

talk about 996. That was at least that

for both Dharmesh and I. We were we were

pedals to the metal the entire time. And

if we weren't working, we were thinking

about working. It's not for the faint of

heart. And

like if you look at my life, it's kind

of interesting. Like I'm 58.

In the years I should have gotten

married and had a bunch of kids, I had

HubSpot. I'm still single.

And yeah, you're kind of married to your

company and you're all you're full on.

Like the 996 thing, it's at least that

for the founders. And I work a lot of

founders today.

It's that's a minimum for the founders,

I would say these days. And and you got

you guys said something on a tweet that

I thought was You said it. That I

thought was kind of interesting. Like

when you're a founder,

like 90% of the time stuff's broken and

you're dealing with problems and things

kind of suck. I'm angry I'm angry most

of the time. I'm angry most of the 10%

of the time it's like, "We got this.

We got it. Everything's going our way.

The wind's at our back." But it's pretty

rare like You live your day looking at

your Slack and your inbox and your texts

and it's mostly bad news in there.

Well, so tell me, once a company gets to

100 or 1,000 employees or 10,000

employees, does that emotion go away?

Same. It's the same ratio. It's still

mostly a [ __ ] sandwich in your

inbox.

Do you feel existential threat? Like my

business, we have plenty of money and

very profitable, whatever. But for some

reason I still feel like an existential

threat all the time where it's like if

we don't do this well, we're going out

of business.

>> Constantly. We were constantly like,

"Salesforce is going to crush us

tomorrow. Did you see their

announcement? We're dead." We said that

so [laughter] many times.

Yeah, we tend to overestimate what our

competitors do and underestimate what we

do. Maybe there's a correlation between

like how like shitty you think you are

and how good of an entrepreneur you make

because maybe there's no correlation,

but there's like a correlation between

people who start businesses because I

noticed that I have like I I personally

have very negative self-talk. Where it's

like, "You're [ __ ] You're nothing. Uh

you have to prove them wrong. You are

horrible. You barely growed. You can't

do this. You have to put like my and it

wears people out there because I

actually think that that's negative

that's a pretty poor way to motivate

people. Uh but it motivates me. I'm the

same and I people say, you know, you

want to be very positive and positive

and motivate the people. I tend to be

paranoid. I still, after all these

years,

have imposter syndrome. I'm a little

nervous talking to you today. Believe it

or not.

>> [laughter]

>> Really? Why? Yeah, I'm not as Given all

the success I've had, my confidence

doesn't even remotely

help me compare to it. And my inner

monologue is like, "You got so much to

prove, dude. Don't [ __ ] it up." Does

Dharmesh feel the same way?

Yeah, I I can't say for sure, but I I I

think very much so.

Do most other So, you run in a circle

with some of the best entrepreneurs on

Earth, most successful entrepreneurs on

Earth. Is that the common thread? Yes.

Almost all of them.

I interview all these CEOs and I ask

them during the interviews, you know,

"Do you have imposter syndrome?" And

they hem and they hem and they haw cuz

they don't want to say they do. They do.

Almost all of them. Let me ask you one

more question about all this and then I

want to know about what you're like more

of the Sequoia stuff cuz I think that's

super fascinating.

Sometimes, I think that with being an

entrepreneur, the hard part I would

think about this a lot and I've talked

about it a lot, which is the hard part

emotionally isn't the risk-taking. The

risk-taking is actually not that

challenging because in a lot of cases

the risk is not that big and you could

like

like even if you go big, you can kind of