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·YouTLDR

He Dropped Out to Build a $9M AI Company — With No Co-Founder or Investors | Yasser Elsaid, Chatbase

1:14:5513,750 words · ~69 min readEnglishTranscribed Apr 11, 2026
0:00

Having a slightly like below average

0:02

co-founder is much much worse than being

0:04

solo. I wasn't like following the

0:05

footsteps of like go first you need a

0:07

pitch deck and then you talk to

0:08

investors and then try to find a

0:09

co-founder and then hopefully you raise

0:11

money and then you start building. I

0:12

just saw the opportunity and I started

0:13

building. Dictatorships make your

0:15

chances of success much higher. If you

0:16

have trust in the founder and you think

0:18

they're smart enough and they have input

0:19

on how to build the product and how to

0:21

get customers, then it should be a

0:23

dictatorship. You don't want them to be

0:24

slowed down. If you bootstrap to 100

0:26

million ARR AI business, anyone would

0:29

call that a success and like it's a

0:30

success for the founder and for the

0:32

team. But I don't think it would be

0:34

considered a success if you raised 100

0:36

million.

0:36

>> What's the case for solo founding?

0:38

>> The case for solo founding is that it's

0:41

very hard to lose. The biggest reason is

0:43

co-founder breakup cuz if you don't have

0:44

breakup, you can just like pivot or you

0:46

can just try to raise more money or

0:47

there's a lot of other options. I like

0:49

the fact that everything is my fault and

0:51

like being solo gives me that

0:53

satisfaction.

0:55

Chatbase has had this incredible

0:57

journey, $9 million in ARR in about

1:01

three years. There was this opportunity

1:02

that you saw and I'm really curious what

1:06

that opportunity was like, how you saw

1:07

it because that ultimately pursuing it

1:10

was the thing that kind of got you to

1:12

building this great business. So, we'll

1:14

just start there. When you saw the

1:15

opportunity, what did that look like?

1:17

>> Yeah, this was very early on. This was

1:20

even before Chad GPT was launched. I was

1:22

using the Da Vinci 03 models. So way

1:26

back in the day, back then it was um

1:30

there was no like API where you can uh

1:33

send the chat and like get back a

1:34

response. It was just you're talking to

1:36

the base model just the completion not

1:38

chat completion. Um and then I saw the

1:43

idea of this is a very powerful model

1:45

but it doesn't have custom data. It

1:48

doesn't have your data. And that in the

1:50

very first uh version of chatbase it was

1:53

just uploading a PDF and then talking to

1:56

it. So like my idea was uploading maybe

2:00

a textbook or just like a book or a

2:03

website or anything and then having a

2:05

chat with it. And of course now it seems

2:08

obvious that this like makes sense and

2:11

is a good idea and people would want

2:12

that. But I talked to a lot of people

2:14

back then and I don't know if it was

2:18

very obvious. I

2:20

I think some people didn't see the value

2:22

or maybe they saw the value but they

2:25

didn't see the models improving. Um they

2:29

just saw like what existed now and maybe

2:31

that was not super super helpful because

2:34

the models were not there yet. But yeah,

2:37

I had like I I thought there is a very

2:39

good chance the models were improved

2:41

because

2:43

um now there's all of these big

2:44

companies that are working towards the

2:46

same thing. So I think I I started

2:50

chatbase with uh one a very good idea

2:54

which is you know custom uh adding

2:57

custom data to like the base model and

2:59

then I bet on the models improving which

3:02

was not very popular back then um and I

3:05

think that's how um we just like kept

3:08

growing as the AI wave has been like

3:12

we've been riding it from since 3 years

3:14

ago. So that's really interesting. But

3:17

in order for you to even get there to to

3:19

realize, hey, we should make it so that

3:21

you can chat with a PDF for instance,

3:24

you needed to be exploring and playing

3:26

around with these things. So what was it

3:28

causing you to even play around with Da

3:30

Vinci in the first place? Like where

3:31

were you? Is I think that often times

3:33

when people are trying to come up with

3:35

ideas and things to work on, um,

3:37

sometimes they're trying to artificially

3:38

do it. And it feels like in many ways

3:41

you kind of came across this through the

3:43

process of exploring things and

3:45

tinkering with things. So maybe you can

3:47

give a little bit of a frame of

3:48

reference for people when they're trying

3:50

to understand how you approached it and

3:53

maybe that would be something that they

3:54

could apply to their lives as well.

3:56

Yeah, I think um

3:59

like honestly the only there's no

4:01

shortcut like the only thing you can do

4:03

is just to like try things and then

4:06

because you're trying things and because

4:09

you're talking to other people and

4:10

because you're in the you know like in

4:11

the group chats in the community, you're

4:13

seeing the new things that uh people are

4:16

releasing, you're getting inspired, then

4:18

you come up with a good idea or like at

4:20

least you see potential in some ideas.

4:23

So the way this happened for me was so I

4:27

was in my last semester uh in in

4:29

university in Canada and I was always so

4:32

I was doing internships but I was also

4:34

doing side projects um with the goal of

4:38

just like having something that can make

4:40

money. Um so this was I was like

4:44

inspired by you know people like Peter

4:46

levels for example. Um and

4:50

I was doing other projects. I had the

4:52

project called called rate my courses. I

4:54

had another project called uh SAPL but

4:58

because I was you know like tinkering

5:00

with things and um you know like trying

5:03

the APIs trying to do stuff that the

5:06

APIs can't do yet just like trying

5:09

things. I saw rag which was uh like I

5:13

saw it very very early on and I think

5:15

that was um you know the spark that

5:18

started uh chatbase and it wasn't even

5:20

called drag drag back then it was just

5:22

like I don't think there was a name it's

5:24

just like you add data you augment you

5:27

add data to a base model so that it can

5:29

know more things um so I saw some people

5:33

like like writing papers about that some

5:36

people were creating like CLI tools

5:38

about that but there was no product that

5:41

you can like open a website, add a

5:43

document and then chat with it. Um,

5:47

so yeah, I think for me it was obvious

5:50

that like this is something people would

5:51

need. Um, and I just stopped everything

5:56

I'm doing in university. I just like

5:59

stopped going to class. And um I had the

6:02

conviction that yeah like this is an

6:05

opportunity that doesn't come often and

6:08

like to be able to see that very early.

6:10

Uh and of course like I didn't know how

6:12

big it's going to be but I had some uh

6:15

conviction on like oh this might

6:18

actually be uh an opportunity and yeah I

6:22

just stopped doing anything else and I

6:23

started executing and then yeah I think

6:27

like a month and a half after um I was

6:29

coding by hand back then so it was still

6:32

slow. Um yeah, a month and a half after

6:36

like getting the idea, I released the

6:38

the first version of chatb.

6:40

>> You know, there's two things that I

6:42

would love for us to talk about, you

6:43

know, regarding that sort of early days

6:45

of of figuring this out. I think that

6:47

one is that people often think that they

6:49

need to have the right idea and they

6:51

kind of just try and go straight to

6:53

figuring out the right idea. It seemed

6:54

like there were a bunch of things that

6:55

you were trying and then ultimately you

6:58

found chatbase sort of through that

7:00

through that process of building those

7:02

other things and that ultimately caused

7:04

you to you know put those other things

7:06

to the side. So I'd be really curious

7:07

just your philosophy and sort of what

7:09

you learned around building those other

7:12

things that kind of got you to the

7:14

position where you'd actually discover

7:16

the chatbased opportunity. And then

7:18

maybe the other thing would be really

7:20

cool to talk about and I think would be

7:21

really useful for people to hear is how

7:24

you how you actually got that sense that

7:27

it was time to put the other things away

7:30

>> and including school but but

7:32

particularly the other projects and go

7:35

all in on this because I think that one

7:37

thing that sometimes people have is they

7:39

do that kind of try out a bunch of

7:41

things but they have a hard time kind of

7:43

abandoning them all and putting all of

7:45

the wood behind one arrow. So, so maybe

7:48

talk about sort of that first part

7:49

though and we can talk about sort of the

7:50

focusing and and doubling down. How how

7:53

do you think about sort of the process

7:55

of like tinkering with other ideas and

7:57

how it ultimately potentially drove you

8:00

towards discovering the opportunity for

8:02

chatbase?

8:03

>> Yeah. So, I think like the normal way to

8:06

go about things is that you, you know,

8:08

like you look at the market, you look at

8:10

competitors, you like research what

8:12

they're good at, you see the reviews,

8:13

you see what their customers are saying,

8:15

and then you from all of that research,

8:19

you come up with a business idea. But I

8:22

think in practice,

8:24

I don't think any business started out

8:26

like on day one with the idea that it

8:29

ended up being as it grew much bigger.

8:32

And I think it's the same even for

8:33

chatbase even after I saw that idea. Um

8:36

so I think for me what happened was I I

8:42

was working on on multiple things. I saw

8:45

one thing that it seemed to me like just

8:48

from first principal thinking like it

8:49

just seemed to me that this is very

8:51

powerful and by just

8:54

thinking about the effects of something

8:57

like this just like sitting down and

9:01

thinking it's just no no market research

9:03

no no talking to users nothing like that

9:05

and I think that's the only way in a

9:08

fastmoving industry like AI because you

9:10

don't have time to talk to users because

9:12

there is no users talk to like this is

9:15

like you are it's like a very it's a new

9:17

paradigm like there's no one to um

9:22

to like you know interrogate about

9:24

something like this because they they've

9:26

never used something like this. Um,

9:29

so I think a lot of things in AI will be

9:33

about like seeing what is possible now

9:37

and like what just became possible and

9:40

ju just like build something around it

9:42

and then while you're building you'll

9:44

find you know the universe pushing you

9:46

towards like a certain direction because

9:48

of many things because of like maybe

9:50

there's a limitation in one idea but you

9:52

find out another idea that works or

9:54

maybe you talk to some people and like

9:56

it seems like hey this is uh an approach

9:59

that you can do things. And I think

10:02

if I think about all the successful

10:05

tools that came out came up from uh from

10:08

like after the LLM era um I think a lot

10:12

of them started out that way. It was um

10:15

as soon as the technology is ready for

10:18

something you see someone build that

10:21

something very quickly like for example

10:23

openclaw or even cloud code and stuff

10:25

like that. uh because the model models

10:28

are now capable enough to you know do

10:30

longunning tasks to like run multiple

10:33

tools to have access to the CLI and um

10:37

not hallucinate

10:39

um because it's a new paradigm. It's

10:42

just it comes from from just first

10:44

principles thinking and not heavily like

10:46

talking to uh like doing a lot of market

10:49

research or talking to a bunch of users

10:50

because it's it's a new paradigm. One

10:52

thing I think you've talked with me

10:54

about in the past, like over dinner or

10:56

something, is like urgency and sort of

10:58

this sense that once you discovered this

11:01

opportunity, at least the the first

11:03

version of what chatbase would be, um,

11:06

you you felt like there was a real

11:08

urgency to get it out there and sort of

11:11

be the first. Um, and maybe that also

11:14

ties into that thing we I was talking

11:15

about earlier that I thought would be

11:16

interesting to hear, which is sort of

11:19

that decision to put everything else

11:20

aside. you know, you had other apps that

11:22

you were working on, maybe varying

11:24

degrees of success and promise with

11:26

those. You had school. So, how does

11:29

urgency tie into that decision and the

11:33

decision that you ultimately made to put

11:35

all the other things aside?

11:36

>> Yeah. So, I think for me the reason I

11:41

was urgent or like I had a lot of

11:43

urgency was not actually right. It was

11:45

the belief that like you can do ideas

11:49

that other people are doing like you

11:51

have to do like I don't know I think a

11:53

lot of people when you talk to them

11:54

about like a startup idea they say oh

11:56

but that exists.

11:57

>> Um and I had like the same like

12:00

misconception that oh I need to do this

12:02

now because if I wait I know like this

12:05

idea is good and someone else will do it

12:07

so I just need to to do it now. But I

12:10

think like the reasoning was maybe not

12:12

right. But the result was I needed

12:15

urgency and that of course was the right

12:17

thing to do. And um a big reason I would

12:21

say for the success of Chatbase was the

12:23

timing and like I think that helped us

12:26

um stay bootstrapped because as soon as

12:29

we launched we we had revenue. uh maybe

12:31

like like I I think I had the first

12:34

payment through Stripe 30 minutes after

12:37

I put out a pricing page. So

12:42

I think yeah I think if you're building

12:44

an AI especially now like now it's

12:46

extremely competitive like now it's very

12:47

obvious that um like this is the future

12:51

and you want to be part of it so

12:53

everyone is building. So I think now

12:55

it's even more uh important to have

12:59

urgency but at the same time to still

13:01

make sure that you you are opinionated

13:03

and not just you know like following the

13:06

trends of um like what's popular now and

13:09

then like jumping to the next thing

13:11

because I think it's very hard to run um

13:14

like a scalable business that way.

13:16

>> You know you've bootstrapped as a solo

13:18

founder to 9 million ARR uh over three

13:21

years. you have quite a following on X

13:24

because people are fascinated and they

13:26

want to follow in your footsteps. Um at

13:29

the same time when you started you

13:32

didn't have a lot of a following. You

13:34

didn't really have much of an audience

13:35

at all. You had no revenue to start. You

13:38

were I guess still in school. So what

13:41

was it actually like back then? How did

13:43

you decide to be solo? Like what was the

13:47

what was the backstory there? I think

13:49

what helped is that I wasn't in SF. So I

13:53

think I I think I didn't like think

13:55

about like what people do when they want

13:58

to start a company or like what the the

13:59

steps are.

14:02

I was just you know like I just saw the

14:03

idea and I started building it. I wasn't

14:05

thinking too much oh do I need to raise

14:06

do I need a co-founder? And maybe like

14:09

maybe like not everyone should do that

14:12

and that doesn't work with every

14:13

business of course but like to me just

14:16

the truth was I saw the idea and like I

14:19

started building. I I wasn't um

14:24

I wasn't like following the footsteps of

14:25

of like oh first you need a pitch deck

14:27

and then you talk to investors and then

14:29

you try to find a co-founder and then um

14:32

hopefully you raise money and then you

14:34

um and then you start building. I just

14:37

saw the opportunity and I started

14:39

building and what helped was as I said

14:40

like we have we had revenue very quickly

14:43

so and also we had like a lot of

14:46

customers quickly and I was alone so I

14:50

didn't have time to like go like find a

14:52

co-founder and raise money like it was

14:54

just all of my time was spent on just

14:58

building the product and then talking to

14:59

customers and maybe if I had more time

15:02

to like think about things I would have

15:04

um tried to find a co-founder or or more

15:07

or raise. But yeah, I think I just

15:10

didn't have the time to do so. And you

15:12

know, I had like some angry customers

15:14

calling me, you know, at 2 am. So like

15:16

that was my my like my whole day um just

15:20

building and improving the product and

15:22

talking to customers until it got to a

15:25

point where um like I can run this

15:28

profitably and hire people and it's been

15:30

that way since then. It feels like in

15:34

many ways solo founding, especially solo

15:37

founding with the bootstrapping

15:38

component. Um, which I guess over dinner

15:41

last night we described this as free

15:43

solo uh is is uh bootstropping solo. Um,

15:47

and then people like Ben, it's like true

15:48

solo if they're bend if they're building

15:50

without any teammates. And we'll talk

15:51

about team in in a in a few minutes

15:53

here. um when you're building this sort

15:56

of you know this this sort of free solo

16:00

uh approach um it does feel like it it

16:03

has a lot of uh that it owes to sort of

16:05

like the indie hacker kind of movement

16:08

um and I'm really curious do you think

16:12

that we're just moving in a world where

16:14

the indie hacker was always thought of

16:15

as a little bit like this is

16:17

bootstrapping kind of puts a ceiling on

16:19

things pretty significantly and indie

16:22

hacking is is quaint and it's about

16:24

making revenue, but it's not about

16:26

building big businesses. You have more

16:28

revenue than a lot of companies that are

16:31

venture-backed 3 years in. Um, so you're

16:33

you're doing phenomenally well. You're

16:35

better than a lot of venture-backed

16:37

companies. So, you're kind of changing

16:39

the narrative around like what a solo

16:42

bootstrapped company looks like. In the

16:44

past, people thought it was kind of like

16:46

this, you know, small business type

16:48

thing.

16:49

>> Um, how do you think about that? How do

16:51

you think about like what's actually

16:53

possible with a solo bootstrap business?

16:55

And maybe, you know, we've talked a

16:57

little bit about it, but I'd love to

16:58

hear kind of what that journey's been

17:00

like and did you realize in the early

17:02

days that it could actually be something

17:04

like this? I know you started it out

17:06

with just the premise of making a

17:08

business that makes some money. So, just

17:10

walk me through a little bit of that.

17:12

>> Yeah, I I agree. I think um when I was

17:16

like the indie hacking movement was

17:19

mainly around building like a lifestyle

17:22

business you know like some people call

17:24

it like a a micro sass or or something

17:27

like that and it's just the idea like

17:29

you want to make profit and then go live

17:32

in Bali. Um which I think like this is I

17:35

think it's extremely valid and I think

17:36

it's

17:38

I think it's it's more possible now with

17:41

with all the AI tools. I think if

17:42

someone has like enough agency and

17:45

enough urgency and drive, I think yeah,

17:49

like that's a very viable path and it

17:51

sounds fun. Um,

17:54

for for me, I I was considering like,

17:57

you know, like building chatbase as a

17:59

lifestyle business and some people were

18:00

doing also like multiple projects um and

18:03

and running all of them at the same

18:05

time. But I think um

18:09

I just saw this as like once in

18:11

a-lifetime opportunity for many reasons.

18:14

I like the timing, the how big the

18:17

market is, how competitive it is. And I

18:22

think maybe like it's it's also human

18:24

like by nature like I'm more competitive

18:27

like I couldn't get myself to okay say

18:28

okay this is enough let's just go you

18:30

know to the beach and uh enjoy the the

18:33

profit. Um, so I think a part of it is

18:36

like the person that is that is running

18:38

things and like what their goals are.

18:40

But for me, the goal was

18:44

always like I want to see this through.

18:46

I want to like I I think it's hard uh to

18:50

find an opportunity like this. And

18:54

I think people get something like this

18:56

maybe like maybe like three times in

18:59

their whole life, maybe less. And most

19:02

people don't take advantage. I feel like

19:04

I I did a good job early on by taking

19:07

advantage and

19:10

you know somehow I feel like I owe it to

19:11

myself to like at least see it through

19:14

like see see its potential. Um and also

19:16

it's fun like I enjoy doing it. I enjoy

19:19

seeing you know the graphs go up. I

19:20

enjoy talking to customers and like

19:22

seeing how this helped them. I I enjoy

19:26

the competitive aspect of it. Um, so

19:28

it's also fun and yeah, that's that's

19:32

mainly the reasoning on like why I

19:34

decided to

19:37

like go all in and maybe raise the

19:39

ceiling of what maybe like uh people

19:44

thought what is possible bootstrapping a

19:46

company especially solo.

19:48

>> It really feels like you have raised the

19:50

ceiling in terms of what people think is

19:52

possible and we have no idea just how

19:55

high that ceiling can go. Um, I'd be

19:57

super curious to hear about the

19:59

competitive aspect of this. Not

20:01

competitors, but like you being a

20:03

competitive person.

20:05

>> Is that something that you identified in

20:07

yourself really early on? What What were

20:09

some of the aspects of being competitive

20:11

that kind of resonated with you or or

20:14

made you sort of who you were when you

20:16

were growing up?

20:17

>> Yeah. Um,

20:20

so I was doing a lot of sports growing

20:21

up. I think maybe that's uh one aspect

20:24

that affected my personality. Um so I

20:29

did swimming, I did archery for a long

20:31

time and you know like going to

20:34

competitions and all of that. I think

20:36

especially when you're young and when

20:38

you with your friends, I think it shapes

20:40

your uh yeah, it shapes your personality

20:44

and I wouldn't say I'm competitive

20:47

because of I just want to like you know

20:50

prove other people wrong or you know

20:52

like I think a lot of founders a lot of

20:54

people say founders have you know like a

20:56

chip on their shoulder and um

21:00

the reason they do what they do is

21:02

because it comes from a place of like I

21:05

want going to prove everyone wrong. I

21:07

don't think I have that. But I think I

21:08

just I think it's it's it's fun to, as I

21:11

said, like to see things through and

21:14

like see the the biggest impact you can

21:17

make. And

21:19

um to me, I'm more like competing with

21:21

myself or like Yeah. Yeah. Honestly,

21:23

competing with myself. I want to like

21:25

see how much I can build this and like

21:29

like just be proud of what I've built.

21:31

Um,

21:33

and yeah, I think that's yeah, that's

21:35

the reasoning behind deciding to just go

21:38

all in and like um try to grow this as

21:41

much as possible, try to get as many

21:43

customers as possible, try to compete

21:45

with companies that raised a lot more

21:48

money than us. So,

21:49

>> infinitely more money than us. So, yeah,

21:52

>> the um swimming and archery, that's

21:54

interesting. Those are those are sports

21:56

that are both individualistic but also

21:59

teams, right? Archery is also a team,

22:00

swim team.

22:02

>> Um,

22:03

>> but and you're competing against other

22:04

people, but you're also competing with

22:06

yourself.

22:06

>> Yeah.

22:07

>> Can you share a little bit more about

22:09

how you think about those sports and

22:11

kind of the relationship between the

22:14

individual their teammates and the

22:17

people that they're playing against

22:18

because they feel like very different

22:20

than say, you know, soccer or football

22:22

or whatever.

22:24

>> Yeah. I think the beautiful thing about

22:26

uh individual sports is that you can

22:29

only blame yourself and I think

22:32

especially when you're young I think

22:33

that teaches you a lot about just life

22:36

and like how you you know go through

22:38

life and conduct yourself through life

22:40

and I think having that mindset of

22:43

everything is my fault I think that's

22:46

very helpful in sports but especially in

22:48

individual sports and that what it teach

22:50

that's what it teaches you but it's

22:52

extreme extremely helpful in business

22:54

also like it's the same um it has the

22:58

same importance if you're working with

22:59

more people I think especially if you're

23:02

the CEO yeah everything is your fault

23:04

because yeah like you're the person

23:07

responsible for anything that's

23:09

happening in the company so I think that

23:10

mindset even if you're working with

23:12

other people I think even if you have

23:14

co-founders I think everyone should um

23:18

take responsibility and I think um you

23:21

know like I I got that lesson from

23:23

sports and I think it helps with

23:25

businesses and especially it helps with

23:27

um solo funding a business. Um but now

23:31

like now I have a relatively big team

23:34

and like a lot of the um value that

23:37

chatbase is providing to customers is

23:39

coming from from the team and I'm very

23:42

proud to be able to have them um like

23:46

working with them especially given that

23:49

they started out you know like in my

23:52

like last semester in school like you

23:54

know like building uh in like a class

23:57

for example. So it it is very special

24:00

and but I want to make sure that I give

24:02

them you know the appreciation and

24:05

recognize they what they help built. I

24:08

think this is such an important aspect

24:10

of it, right, which is you're not this

24:13

is actually kind of an interesting thing

24:15

because oftent times people like, well,

24:17

you know, they're not solo, they have

24:19

team, of course, like most companies do

24:21

have teams and probably will have teams.

24:23

Maybe they'll be smaller teams in the

24:25

future because more leverage for each

24:26

individual with the tools that they

24:28

have,

24:29

>> but you know, there's this really

24:30

interesting dynamic of course where

24:32

you're solo, but you build a team. Yeah.

24:35

Um, and I think that there's a very

24:37

interesting dynamic of going from one

24:40

person to multiple people. If you have

24:43

co-founders, you already have done that,

24:45

right? Because if you have two other

24:46

co-founders, there's three of you. When

24:49

you add the first sort of non-founder to

24:51

the team, you're going from three to

24:53

four perhaps, right? Uh, but if you're

24:56

solo and you're adding the first

24:58

teammate, you're going from, you know,

25:00

one to two. So, it's it's this big

25:01

shift. I'm curious what that was like.

25:04

how you evaluated thinking about when to

25:06

add the first person. Um what kind of

25:09

role that that person had. Um obviously

25:12

this was also at a different time. So

25:14

you know technology was different. The

25:16

tools are different. So maybe if you

25:18

were to actually sort of think about the

25:20

way that you you did hiring if a company

25:22

were doing hiring today, they would do

25:23

different hiring than they would have

25:25

maybe, you know, 3 years ago. But I'm

25:27

really curious sort of what that was

25:28

like in the early days of considering

25:31

bringing on a person um to kind of go

25:33

from being truly solo to having a team.

25:36

I didn't have the choice like I think it

25:38

was extremely obvious that I need I need

25:40

to hire someone. It was just this

25:43

exponential growth you know on the in

25:44

the first two I think I hired the first

25:46

person like two and a half or three

25:48

months in uh after the first launch. Um,

25:52

and it was just impossible to keep up

25:53

with talking to customers, with building

25:55

their features, with everything. Um, I

25:58

think for me, I was lucky because the

26:01

first person I hired is a friend from

26:03

school. So like we already had that

26:06

relationship. And I think it's the same

26:08

for most startups. I think that would be

26:11

a good idea to like just hire someone

26:12

you know and already trust because as

26:16

like everyone says, the first few hires

26:17

like determine the culture of of the

26:19

company. Um,

26:22

so I think it for me like at at some

26:25

point there was no way I can continue

26:27

doing this solo and I knew that I wanted

26:29

to grow this as much as I can. And I

26:32

hired that first person. He was an

26:34

engineer, my friend from school and

26:38

maybe like a month after I hired the

26:40

second person and also a friend. And

26:43

then it just um

26:46

like I think maybe the mistake I made is

26:49

I hired too slowly even not not because

26:52

people say like you only hire when it's

26:54

painful.

26:55

>> Yeah.

26:55

>> Which I did that but like not on

26:57

purpose.

26:58

>> Um but I think I continue to do that and

27:01

I think maybe that's one aspect of

27:03

bootstrapping that you're kind of forced

27:05

to

27:07

be a little bit more careful than if you

27:09

would have raised. And I think I fell

27:11

into that. I wouldn't call it a mistake.

27:13

I think like I did what um made sense at

27:16

the time, but I think if maybe I knew a

27:19

bit more, I would have been more

27:21

aggressive and like maybe hire faster,

27:23

spend more money faster. But I think

27:26

that's what I'm saying about

27:26

bootstrapping. It's um

27:30

the when when people think of a

27:32

bootstrap company now, it's more like

27:35

they associated with like the indie

27:37

hacking, you know, lifestyle business,

27:38

which I it it is a big part of it, but

27:41

but now I think you will see uh

27:44

hopefully companies like Chadbased, but

27:46

I think other companies too will be solo

27:48

founded and maybe bootstrapped and they

27:51

will become huge. Um because I think now

27:53

the technology allows it and I think now

27:58

also more and more people want to start

28:01

companies and I think like the number of

28:04

founders is just going up. So I think

28:05

the number of solo founders will just go

28:07

up and bootstrapping is now a viable

28:09

option to build a generational company

28:12

and maybe the mistake that I made of

28:16

like maybe being too careful very early

28:18

on and um making sure that we're always

28:22

like very profitable above a certain

28:24

amount maybe some people will be more

28:26

aggressive and yeah I see that as uh

28:30

like a good strategy if the goal is to

28:33

build something generational. you know,

28:35

>> so we could I I want to talk a little

28:36

bit more about sort of the team and sort

28:39

of how you think about culture and

28:41

building in real life versus uh versus

28:43

remotely. Uh but before we get into

28:45

that, I think there's a really

28:46

interesting point that you made, which

28:48

is it's more possible than ever before

28:50

to build bootstrapped and to build to

28:53

something of really meaningful scale.

28:55

Not sort of like the that I don't mean

28:57

this in a derogatory way, um but you

28:59

know, some people sometimes do when they

29:01

say lifestyle business. Um there is

29:04

something really interesting about this

29:06

idea that you can make a lot of progress

29:08

with very little and you could

29:11

essentially be profitable. And then

29:12

there's a question of what do you do

29:14

with that? Do you continue to be

29:16

profitable and do you raise venture

29:18

capital? Um there was somebody in the

29:20

solo founders program who got to $2

29:22

million in ARR completely solo, no

29:25

teammates, and now he hired his first

29:27

teammate. He had raised a little bit of

29:29

money, but he didn't touch any of it.

29:31

you know, it just it it was just that it

29:33

was there and it didn't end up getting

29:35

used. So, in theory, he could have

29:37

bootstrapped it, right? Um, now, will he

29:40

raise more money? He's debating it. And

29:42

I think that's a really interesting

29:44

question that a lot of people have is

29:45

they have the success as you have or as

29:48

as he has. And you now it's a question

29:51

of well should they continue to just

29:53

grow sort of with profits uh especially

29:56

if they're really profitable if it's a

29:57

sort of more software oriented business

30:00

or at some point does it make sense to

30:02

consider taking money and you're doing

30:04

it from a place of leverage that maybe

30:06

you didn't have before. So I'm curious

30:08

sort of what your philosophy has been at

30:09

least to date. Uh because I'm sure there

30:12

have been you know quite a few times

30:13

when people have asked about you know

30:15

potentially investing that sort of

30:17

thing.

30:18

>> Like everything else it depends on I

30:20

think the main thing it depends on is

30:22

the founders's goal. Um,

30:26

I think there is a ton of advantages to

30:29

raising and I think the biggest one is

30:31

you get to be more aggressive because

30:34

you have this money and like you're

30:36

supposed to use it, you're supposed to

30:37

spend it and um maybe you do that some

30:41

mistakes along the way with with hiring

30:42

and stuff, but I think overall it um you

30:46

just get to move faster, which means you

30:48

capture more of the market. And in some

30:50

markets that's you know the name of the

30:52

game. it's like who's going to get more

30:54

customers faster. Um, and then also the

30:57

other advantage maybe for especially if

31:00

someone like young or maybe it's like

31:03

their first company or they don't have

31:05

um like a following or something. I

31:08

think the other advantage is some uh

31:10

social proof. You know, when you have

31:12

like the logo that this customer this uh

31:15

firm invested then it it helps a little

31:17

bit with getting customers and hiring.

31:19

But I would say the biggest advantage is

31:21

just being more aggressive because

31:24

I I know I was like this and I think

31:26

other maybe Bootstrap founders also had

31:29

the same problem. It's just it it's not

31:31

the same when you're spending your own

31:33

money like customer revenue. You you

31:35

want to make sure that it's ROI positive

31:37

all the time. You want to make sure that

31:39

you see the results very quickly, which

31:42

also like is a good mindset to have, but

31:44

in some cases, you want to like be more

31:46

aggressive and experiment and and um

31:49

maybe do some things that are maybe

31:53

sounds stupid, but they have like some

31:54

chance of success. But yeah, I think

31:56

that's the main reason to raise if you

31:59

already have profit. Um

32:03

but I would say on the other side like

32:06

why people would not trace um if they

32:09

have a growing business is one they

32:12

think maybe it's like they're delusional

32:14

but they think they can build a brand

32:17

that is strong enough that they don't

32:19

need to associate it or like to borrow

32:22

brand equity from a big firm. Um which I

32:25

feel like that's that's the goal for me.

32:27

like I want to be able to um

32:33

like maybe maybe it's stupid honestly

32:35

but I'm just saying um I have like the

32:38

confidence the self-confidence that I

32:40

can make this a strong brand that people

32:42

recognize that people want to use that

32:45

you know it's not like the alternative

32:46

to something it is just the best tool to

32:49

use and um I think I can do that um

32:54

without without raising so that's one

32:56

one thing And then the other thing is

32:58

about um

33:02

just maybe optionality and control. So

33:05

when you of course you have like maximum

33:08

optionality and control when you when

33:09

you're on your own. Um some people value

33:12

that. I value it to some extent. Um and

33:17

then I would say the the third reason is

33:19

the definition of success changes as

33:22

soon as you raise. So it depends also on

33:25

the person but if you bootstrap to 100

33:28

million ARR AI business I mean I think

33:31

anyone would call that a success and

33:33

like it's a success for the founder and

33:35

for the team. Um

33:38

but I don't think it would be like

33:40

considered a success if you raised 100

33:43

million. Um,

33:46

and

33:48

I think for me and like I think for

33:50

other businesses too,

33:52

it might be easier to get to what you

33:56

consider success if you don't raise

33:58

because just the ceiling is just changes

34:00

so much. And I think even if you have

34:03

the self-confidence, even if you know

34:05

you built an amazing product that

34:07

customers love, um, like I I don't think

34:11

anyone knows what's happening in AI now.

34:12

it's very unpredictable. So, um

34:17

there is an argument to be made that

34:19

it's just higher chances of success if

34:21

you bootstrap. there's something really

34:24

um remarkable about

34:28

Chatbas's growth and um clearly there

34:31

was the timing as you said um and there

34:34

were a bunch of sort of external factors

34:37

but there's also you and the team and

34:41

it's not like you just built one product

34:43

and that was what the product is today.

34:47

It's very different than what you

34:48

started with. Um, and I think that

34:51

that's perhaps something that's really

34:53

worth talking about because I think

34:55

people would really benefit from hearing

34:56

kind of you start with one thing and you

34:59

end up at a really different place,

35:01

maybe a place that you hadn't

35:02

necessarily predicted. So maybe you

35:04

could talk a little bit about that like

35:06

chatbase, what was it the very early

35:08

days and then maybe take us quickly

35:11

through to where we are today.

35:12

>> Yeah. No, I think you should like the

35:15

product should change over time. Like

35:17

that's the whole point of you know

35:18

building the product is it evolves as

35:22

the market evolves as your customers

35:24

needs evolve as your goals evolve. Like

35:26

this is I don't think it makes sense to

35:29

you know like plan the next year in

35:32

advance and just like ignore everything

35:34

that's happening around you. That

35:36

doesn't make sense especially in AI when

35:38

when everything is moving fast. Um like

35:40

you need to be flexible enough and

35:44

you need to also communicate that with

35:46

the team that we have like an idea of we

35:50

have a strong plan. we we know what we

35:51

want to build but you also have like the

35:54

flexibility and the um

35:57

like the team is is small enough and

36:00

fastm moving enough that you can like

36:02

change things as you know like the

36:05

technology changes or as the market

36:07

needs changes or like as a new like

36:09

competitor enters the market. So, you

36:11

have to have that quick moving ability.

36:12

And I think also that's easier when

36:14

you're bootstrapping, when you're on a

36:16

smaller team because you have control

36:18

and you you're just a dictator. Like you

36:20

can just decide what you want to do. And

36:22

I think like dictatorships are good when

36:25

you're trying to build a company. Um

36:28

because yeah, that's a tangent, but I I

36:31

I think

36:32

>> Say more about that though. I mean, like

36:33

I've heard it described as like

36:35

benevolent dictatorship.

36:36

>> Yeah. say more because I think that's

36:38

something that's relevant to solo

36:40

founding, right? Which is that sometimes

36:42

when you have co-founders, it could be

36:44

somewhat, you know, uh somewhat

36:46

difficult to necessarily get to the

36:49

really pointed decision that needs to be

36:51

made.

36:51

>> Yeah.

36:52

>> I I'm curious like talk more about the

36:54

benevolent dictatorship.

36:56

>> Yeah. I think

36:58

I think it's very important and I think

37:00

like of course I don't know the inner

37:02

workings of like the biggest companies

37:04

but I think you associate every big

37:07

company with one person and they're the

37:10

face of the company and they're the

37:11

decision maker and I think like

37:14

dictatorships

37:16

make your chances of success much higher

37:18

um because like there is two scenarios

37:21

one the founder is smart and the team

37:26

trusts them and um they have the agency

37:29

and they have the skill to build an

37:30

amazing company and in that case you

37:32

want them to be a dictator. You don't

37:34

want them to be slowed down but like by

37:36

convincing everyone with about their

37:38

like thought process and like making

37:40

sure that a consultant comes from

37:41

outside to validate you know their

37:43

thinking and all of that. So if you have

37:46

trust in the founder and you think

37:47

they're smart enough and they have input

37:50

on how to build the product and how to

37:52

get customers then it should be a

37:55

dictatorship. And then on the other side

37:58

like if the if the founder is not smart

38:00

enough and if they like their team

38:04

doesn't have like full trust in them

38:06

then this company is not going to work

38:07

anyway whether or not it's a

38:08

dictatorship. So the only way you like

38:12

have like a very big success is

38:16

being a right like dictator like your

38:19

your decisions are right and you don't

38:21

waste time convincing everyone about

38:24

what you want to do. Um so I think it's

38:27

just makes you move faster. It makes

38:29

pivoting like not pivoting but like

38:31

product decisions very fast and even

38:33

pivoting if it comes to that. So, um I

38:37

think it just that's like one of the

38:39

biggest advantages of of building like

38:41

being a solo founder. And I I think also

38:44

if you do have a co-founder, I think it

38:46

needs to be very clear who's going to be

38:48

dictator and what. Um and I think then

38:51

it can work. But if it's

38:54

if it's yeah, if it's like not not very

38:57

obvious who's doing what like like the

38:58

responsibilities are like uh there is a

39:00

gray area, then I think it becomes a

39:03

very big problem.

39:05

Maybe let's shift it back to what before

39:07

we went on this little rabbit hole,

39:08

which was a really good one. Um, sort of

39:11

how maybe that benevolent dictatorship

39:13

or whatever um caused you to go, you

39:16

know, from place to place to actually

39:18

get from first version of chat base to

39:21

where you are today because that I'm

39:22

guessing it's not exactly a straight

39:24

line. Yeah. Um, but what was the what

39:26

was the evolution there and what were

39:28

you learning along the way? Yeah, I

39:30

think um what's interesting in in

39:33

startups in general, but especially in

39:35

AI startups, is that the inputs change

39:39

every day and then you make a decision

39:42

based on what you know today, but then

39:45

you shouldn't have ego to say like like

39:50

let's say like a week after or a month

39:51

after and then some inputs changed and

39:54

then you the decision you made was a

39:56

mistake. then you need to like just go

40:00

in a different direction very easily and

40:01

like very quickly and 100% it's not

40:05

going to be a straight line. It wasn't a

40:06

straight line for us. It's I don't think

40:07

it's a straight line for anyone because

40:10

especially in AI everything is changing

40:12

so quickly. So your job as a founder I

40:14

think is for like decision- making is

40:17

two things. one, you need to make sure

40:20

you take in all the inputs that you have

40:22

today and like make sure you think from

40:25

first principles on what the best

40:27

decision is that I can make with

40:30

everything that I know now with all the

40:31

context that I know. But also not having

40:35

the ego to say no, we're going to

40:37

continue doing this after like things

40:40

change and making sure that um you and

40:44

everyone on the team are

40:48

you know, low ego enough to be able to

40:50

change your mind very quickly to respond

40:52

to like everything that's happening

40:54

around you. um that makes you know like

40:57

long very long-term planning hard but it

40:59

is hard and I think it's hard for all

41:01

the startups and it's even hard for the

41:03

AI labs and you know the people that are

41:05

creating this technology because like

41:09

the truth is no one knows what's going

41:11

to happen you know like two months from

41:13

now like what the products are going to

41:15

look like what the market is going to

41:17

look like what the customers will want

41:19

it's just very unpredictable u you can

41:23

have assumptions and like you can some

41:25

accuracy, but

41:28

yeah, you need to be low ego enough to

41:31

be able to change your mind very

41:32

quickly. And I think Jeff Bezos um had a

41:36

quote, I I forget exactly what it said,

41:38

but something like you need to be able

41:41

to make the decisions that it's very

41:44

easy to come back from.

41:46

>> And I think that's the case for like

41:48

especially AI startups. If you have a

41:51

decision that you can like walk back on,

41:53

you know, a week from now if things

41:55

change, you should do that instead of

41:56

doing something that it's very hard to

41:58

to walk back on. So yeah, for chatbase

42:01

it was a lot of like thinking, you know,

42:04

today like what should we do and then

42:06

changing it, you know, a week after and

42:08

then like thinking about something new a

42:10

week after and then oh actually it works

42:12

so we don't change it. we were going to

42:13

continue doing it. And over time, over

42:17

like yeah, the years it uh

42:21

chatbased became what it is today. And

42:22

we're still like going through that.

42:24

>> It feels like there's um this idea of

42:27

like one-way door decisions, two-way

42:28

door decisions. Um everybody like I

42:31

think the main the main challenge is

42:33

that everybody treats all decisions as a

42:35

one-way door decision. And what you're

42:37

saying is there's so many decisions that

42:39

are actually two-way door decisions that

42:41

are totally reversible, but because we

42:44

we kind of have this human nature of

42:47

kind of

42:48

>> clumping everything together, uh we we

42:50

treat the the two-way door decisions as

42:53

one way door and it makes it really

42:54

hard. Um that's probably the biggest

42:56

impediment on velocity, right? U. So I'm

42:59

curious, how do you kind of encourage

43:02

the team and create a culture for the

43:04

team to not feel like they're always

43:07

going through oneway doors, so therefore

43:08

they have to be extremely careful? Um,

43:11

maybe not have to always get your

43:13

permission for things, right? Because,

43:15

you know, you're you're not steering,

43:16

but you're directing, right? You're

43:18

telling you're saying, "Here's the

43:19

direction we want to go in." And then

43:21

ultimately, you know, you you need to

43:23

give them the ability and encourage them

43:26

to do their great work and make their

43:28

great decisions because you can't be the

43:31

person who makes all the decisions. So,

43:32

how how do you do that? Like what's the

43:34

culture like? How did you think about

43:35

building the culture? I'm sure that

43:37

there are things you've learned along

43:38

the way that um that were maybe like

43:41

missteps. Every company has those. I'm

43:42

just curious what what that's been like

43:44

for you because this is the first time

43:45

that you've ever really built a company,

43:47

right? It's kind of like you were you

43:48

were in college and then now now you're

43:50

running I think it's a 30 person company

43:53

$9 million bootstrapped solo founder. So

43:56

what walk walk me through like walk us

43:58

like the listeners through like what

44:00

that actually was like what you've

44:01

learned about building a culture that

44:03

supports these things that are

44:04

important.

44:05

>> Yeah, I think the biggest thing um for

44:08

me to learn or like that I learned and

44:11

that I made sure everyone on the team

44:12

knows is that changing your mind is

44:15

actually good. like you should change

44:17

your mind if if things change because

44:21

I think if you don't like make sure that

44:22

this is explicit if you just like let

44:24

things happen there is this um you know

44:27

like social pressure a little bit to

44:30

like not want to look like you changed

44:32

your mind or like to say oh actually

44:33

like this was a bad decision we should

44:35

do something else.

44:37

changing your mind like you should

44:38

change like actually not changing your

44:39

mind is a problem because

44:42

like inputs are changing very quickly

44:45

and sticking to something just because

44:48

you don't want to look bad is like such

44:49

a bad uh idea for for the smaller

44:53

decisions and then especially for the

44:54

bigger decisions. So I think in the

44:57

culture for us and I think for like a

45:00

lot of um what AI companies should do I

45:03

think honestly like any company is

45:05

encouraging like making sure that if

45:08

someone decides to change their mind um

45:11

there is like zero pressure on like oh

45:14

but you said this or oh but like we put

45:16

in all this work to do this or you know

45:18

like the sunk cost fallacy because

45:20

things things have changed. So yeah, and

45:23

I think like the way you build that

45:24

culture is by just like one doing that

45:27

yourself and then making sure you

45:30

communicate that with with the team like

45:32

very regularly. So like it's still in

45:35

you and everyone on the team that this

45:36

is how how we do things.

45:38

>> Now I think there's um I think there's

45:41

something really interesting and maybe

45:42

we could we can sort of transition over

45:44

to just like what it's actually like to

45:46

build a bootstrapped company that

45:48

scales. Um, I think a lot of people have

45:50

a general sense of maybe what it's like

45:52

to build, you know, these smaller like

45:54

soloreneur

45:56

indie hacker businesses that don't scale

45:58

because it's just, you know, one person.

46:00

But, you know, there are some really

46:01

interesting questions around how to

46:03

think about profitability versus

46:05

investing in, you know, different things

46:07

internally, how to think about hiring,

46:09

how to think about compensating people.

46:12

Um, I'm sure to some extent the people

46:14

that you attract to the company, you

46:16

attract different types of people

46:18

because you're a different type of

46:19

company. So maybe you could share a

46:21

little bit more about sort of the sort

46:23

of the practical sort of things that

46:26

you've learned when it comes to like

46:27

finances and sort of attracting and and

46:30

retaining talent at at sort of a a

46:33

scaled bootstrapped company.

46:35

>> Yeah. Yeah, that's a good question. I

46:37

think so like rule number one if you're

46:41

not rich like you're not financing this

46:43

yourself is you have to be profitable

46:46

like there is it's not optional like you

46:48

have to be profitable from day one um

46:51

how profitable is is the question and

46:53

that that's what what I was mentioning

46:56

in like risk tolerance or being a

46:58

aggressive I think like of course when

47:02

this is like your first company and

47:04

you're just starting out you you the

47:06

it's very unclear like what this will

47:09

grow into. Um you tend to be more you

47:12

know conservative and like just want to

47:14

make sure that this is like the unit

47:17

economics make a lot of sense like

47:18

that's the number one metric you're

47:20

you're tracking but then as

47:24

like you gain some mode around the

47:26

company and like you you have some

47:28

confidence and like the steps that you

47:30

need to take are clear in order to grow.

47:33

Um then once you have that conviction

47:36

then you can be more aggressive. I would

47:38

say you can even start to lose some

47:39

money from like all the money that all

47:42

the profit that you have been building.

47:44

And that's what we're like that's where

47:47

we are now. Basically, we

47:50

are investing

47:52

I would say like we we may be even like

47:54

spending more money than a lot of like

47:56

VC back companies because we have been

47:59

profitable for a long time and

48:03

now there's we have a lot of conviction

48:06

on what we're building and

48:09

to to me it's a matter of execution. So,

48:13

it's I know it's not going to be easy,

48:14

but it the steps are clear like we need

48:16

to do this and this and this and it's

48:18

going to grow. Um, and I think that's a

48:20

very good position to be in. And once

48:22

you have that, then you should like just

48:25

go all in like because if you do believe

48:27

it, then like there is no it it doesn't

48:30

make sense to not do that. Like it's not

48:32

logical. I think that the it's like a

48:35

spectrum on like how aggressive you want

48:37

to be and

48:41

that the it just depends on like how

48:43

much conviction you have on if I do this

48:46

then we will grow. Um if I put like this

48:48

amount of money in this one thing it

48:50

will grow then you just put it because

48:51

it makes sense. And this this also

48:54

depends on like the the person building

48:56

like how much risk they want to take.

48:59

But um but to me like in the market

49:03

we're in and like for the goals that we

49:05

have there is no other way around like

49:08

spending money. So this is what we're

49:10

doing.

49:11

>> And when it comes to the people that you

49:13

track to work at this company, you know,

49:15

there are some companies that are

49:17

obviously out there that are trying to

49:18

raise a lot of money. They're doing it

49:21

and they're getting these really large

49:23

paper valuations that continue to go up

49:26

up up, right? Um, and those valuations

49:29

are usually not tied extremely directly

49:32

to revenue, right? They might be uh

49:34

directionally tied to revenue or or

49:37

success metrics or progress, but you

49:39

know, it's it's a different game than

49:42

like joining a company that's

49:43

profitable, that's growing really well,

49:46

um, that has like, you know, already at

49:49

your stage venture scale metrics for a

49:53

nonVCbacked business. What is it like

49:56

when it comes to recruiting people? Like

49:58

what are people looking for when they

50:00

join your company versus maybe joining

50:02

one of these companies that's maybe more

50:04

splashy but maybe you know isn't

50:07

necessarily doesn't have like the actual

50:09

like

50:10

>> business foundation that you do. I'm

50:12

curious like what what kind of people

50:14

are excited about that? What gets them

50:16

excited? And then also how you think

50:17

about actually incentivizing people. Is

50:19

it just the same thing as like venture

50:21

scale like venturebacked? It's not

50:23

venture scale because you're both

50:24

venture scale venturebacked startups or

50:26

is there something else that you do

50:28

around dividends or how do you think

50:29

about these things? I I don't know

50:30

anything about this world. So, I'm

50:32

really curious about it.

50:33

>> Yeah, that's that's very interesting. I

50:35

think 100% you you attract maybe

50:37

different types of people. Um I think

50:41

it's

50:43

more difficult a little bit because it's

50:46

hard to communicate the value. But I

50:48

think like this is the truth. I think it

50:51

makes a lot more sense to join a company

50:54

that is bootstrapped and has a lot of

50:58

like business uh like value in the real

51:01

world like revenue and customers. It

51:03

makes a ton more sense because

51:06

if you are joining a company that like

51:09

has just raised and you know they have

51:11

like the

51:13

um you know like the news article about

51:15

like the the raising and stuff like that

51:17

then it's like splashy um I don't know

51:21

if this is the best move to be honest

51:22

because that means like you're either

51:25

late like you might be late there's a

51:27

chance that you're late if the company

51:29

doesn't live up to the very high

51:30

valuation that that they have which like

51:33

Of course, some companies do and some

51:34

companies don't, but it's a risk you're

51:35

taking.

51:36

>> Um, and you need the company to not only

51:41

grow into that valuation, but grow past

51:43

it because like you're taking risk by

51:45

taking options. You're not taking like

51:48

just straight out equity. You're taking

51:49

options and then the options are going

51:51

to be based on the the valuation uh that

51:54

they just raised at. So

51:57

I feel like it's extremely more risky

51:59

than to join a company that is

52:01

bootstrapped and then like your options

52:03

mean something because the valuation is

52:05

not based on you know like revenue like

52:08

five years from now uh as as a lot of

52:11

like companies that are VC backed uh

52:13

their valuation is but I think like I'm

52:16

trying to put myself like you know in

52:17

like the the the shoes of a candidate. I

52:20

think the good thing about joining like

52:22

the splashy like the company that just

52:24

raised I think it looks better on your

52:27

resume. That's

52:28

>> social signal.

52:29

>> Yeah, social signal just looks better on

52:30

your resume.

52:31

>> But I think from

52:34

>> I think it's just more risky because

52:36

like

52:38

>> you you're betting that this company is

52:40

going to grow not to that valuation but

52:42

even more. Um and it's like you can make

52:45

that bet, but it's it's still a risk

52:47

you're taking. Um, but I think for for

52:50

some com there there's huge companies

52:52

that are bootstrapped and they I think

52:54

AHFS is bootstrapped and they do

52:56

dividends and like they're growing super

52:58

like I think they're over 100 million in

53:00

ARR and they I think every year they

53:03

give out like like 50% of their I'm

53:06

making this up but I just remembered

53:07

reading this.

53:08

>> Uh, but a lot of their profit just goes

53:10

straight to the to the employees. So I

53:13

think that's um

53:16

like you can do stuff like that when

53:17

you're bootstrapped and like you can do

53:19

stuff like that when when you do raise.

53:21

Um

53:23

but yeah, for us like I think what's

53:25

attractive when when I'm like talking to

53:27

a candidate is one like

53:31

this is like we don't have like the

53:33

paper valuation so you don't have like

53:35

the the problem with the options and

53:36

then two you get to take on like much

53:41

more responsibility just because like

53:42

this is a smaller team and you just like

53:46

tend to move up extremely quickly u

53:49

because by the fact like But this this

53:51

is being a small team and also like

53:54

bigger companies are more like hiring

53:55

executives from like outside like other

53:57

companies not from like people growing

54:00

from the inside. Um but like a a

54:03

bootstrap company wouldn't be able to do

54:04

that because they can't afford that. And

54:06

then the third thing is that

54:09

when you own like all of the uh equity,

54:14

then you can be a lot more generous with

54:16

with the equity that you give out to

54:17

employees because

54:19

like you own all of it. So you can just

54:21

decide to give your best employees a lot

54:24

more equity and that equity also has

54:26

value today. So, and I think a lot of

54:30

people like when when they think more

54:32

about it from first principles, they

54:34

they come to the same conclusion which

54:37

oh like this might actually be a better

54:39

approach and like this is like maybe

54:42

unintuitively like a lot less risk. Um,

54:46

and yeah, by doing that, I think I was

54:48

able to attract like extremely good

54:50

candidates who had offers from like

54:52

those like ventureback companies that

54:54

would seem from the outside um as like a

54:59

like a VC backed brand. But I think

55:02

yeah, once you think about things from

55:04

first principles, maybe you can like

55:07

sway your opinion towards this

55:08

direction. You know, there's there's

55:10

also something interesting is like once

55:11

you scale to a certain amount of

55:13

revenue, it's possible that you could

55:14

actually just sell like employee shares

55:17

t, you know, uh, founder shares to

55:19

investors as well if you ever wanted to

55:21

do it instead of just raising sort of

55:23

straight up like raising uh, preferred

55:25

shares or something like that. But I

55:27

think I thought was, you know, I've

55:28

never done this before, but I thought it

55:29

might be interesting even though um, you

55:32

know, we we've covered a lot of ground.

55:34

Maybe we should actually just really

55:35

quickly, if it's cool with you, talk

55:36

through a few of the um a few of the

55:38

things you've written about in the past.

55:40

Um I you had this playbook that you

55:42

published on X that we could link to uh

55:44

about bootstrapping and AI agent

55:47

business. Um and I thought there were

55:48

some really interesting things here that

55:50

maybe we could do like a lightning round

55:51

on. Um you said if you're in B2B just

55:54

due to the B2B stuff, what does that

55:56

actually mean? Yeah, I think especially

56:00

for bootstrap founders, you tend to try

56:03

to like force your B2B business to run

56:06

like a B2C, you know, app

56:08

>> and that's because customer acquisition

56:11

is just cheaper in B2C. So like because

56:13

you're you're bootstrapped maybe you

56:15

don't want to spend a lot of money in

56:17

acquiring customers and you're trying to

56:19

build like this extremely productled

56:22

like no one is going to talk to me

56:23

>> self-s serve

56:24

>> self-s serve uh app and it just doesn't

56:26

like it can work but you still have like

56:30

if you actually want to build something

56:31

big quickly

56:33

um I think the approach can be like

56:36

product like self-s serve and then um

56:39

attach like a salesled on top of it

56:42

because

56:44

at some point you're going to have like

56:45

bigger customers and you're going to be

56:47

talking to like a middle manager at like

56:49

a public company and that person like

56:52

especially if your product is good and

56:53

like it's there's like a lot of features

56:55

and like it's it can do many things that

56:58

person will not spend like a week you

57:00

know like on your dashboard trying to

57:01

make it work even like even if your

57:04

product is extremely intuitive and very

57:07

easy to use is just very hard to

57:10

convince people to spend time in like

57:12

setting things up and a lot of people

57:14

like value like talking to humans and

57:17

like getting on sales calls and like

57:18

understanding the product and making

57:19

sure that this is like there is humans

57:21

behind this. This is very valuable. Um

57:26

and yeah, I think

57:28

that's that's the only way you can you

57:30

can continue to grow past past a certain

57:32

point. And and just really quickly like

57:34

when you when you added sort of the the

57:37

more salesoriented approach where you

57:40

were actually talking to prospective

57:41

customers versus it being self-s serve

57:43

at what stage was the company like how

57:45

much money did you have? How many

57:46

customers did you have because you were

57:48

originally fully self-s serve I believe.

57:50

So when did you when did you add that

57:51

layer?

57:52

>> Maybe like a few maybe like six seven

57:55

months ago when we were like

57:57

>> Oh wow. So ve very recently in the

57:59

scheme of things.

58:00

>> Yeah. Because like before like we grew a

58:02

lot quickly like in the last also a

58:04

year. So before then like we didn't have

58:07

like it's just hard to hire sales people

58:08

because they're expensive and getting on

58:12

calls with customers and like going

58:14

through like long sales process sales

58:16

process is expensive and you can't just

58:19

do that when you're bootstrapped and you

58:21

don't have revenue. But after a certain

58:23

point we we had the revenue and like we

58:25

had the conviction that this will work.

58:27

So we started invested more into

58:30

building a sales team, building like the

58:32

salesled approach, you know, doing like

58:34

the B2B stuff, doing the outbound,

58:35

talking to customers and all of that.

58:37

>> So there were two there were two points

58:39

here. The first one or this is number

58:41

two is content is non-negotiable. And

58:43

then number three, which I think is very

58:45

connected, is warm outbound is the

58:47

lowest hanging fruit. Um maybe talk

58:49

about both of those at the same time

58:51

because warm outbound is probably a

58:53

concept that most people haven't even

58:54

thought of. They think of cold outbound

58:55

typically. So maybe say how content

58:57

being non-negotiable fits into like this

59:00

warm outbound being sort of the the

59:02

biggest opportunity for a lot of people.

59:04

>> Yeah. So

59:07

I think you can do two things like as I

59:10

said there's two approaches. One is like

59:12

the self-s served productled. You just

59:14

like you're just basically doing

59:15

marketing and like you're just hoping

59:17

people go through the onboarding flow.

59:18

You're treating it as like a B2C

59:20

company. And then on the other end of

59:23

the spectrum it's salesled. you just you

59:25

just have like a landing page with a

59:26

book a demo and then you just have like

59:28

sales people try to connect with

59:30

executives at big companies but I think

59:33

what's very interesting and I think

59:36

actually a lot of companies that are

59:37

huge that I look up to are doing that is

59:41

out of both they have the marketing the

59:45

media arm as just like to get people

59:48

familiar with the brand to have more

59:49

brand awareness but they don't just

59:52

leave it to them to like go on the

59:53

product and sign up. They pull them like

59:56

they actually pull them by sending the

59:58

emails, going on calls with them and

1:00:01

making sure that they go through the

1:00:02

whole pipeline. So I think that's the

1:00:05

idea of warm outbound. The good thing

1:00:07

about content and and marketing is that

1:00:10

it makes everything else you do easier.

1:00:12

Like it makes paid ads easier because

1:00:14

people know your brand and like they're

1:00:16

more likely to watch your content

1:00:18

because they have seen you before.

1:00:19

They're more likely to click on it

1:00:20

because you have like social proof. So

1:00:22

like organic content just makes

1:00:25

everything else easier. It makes

1:00:26

outbound easier because people have seen

1:00:28

you before. Maybe they someone like told

1:00:31

them about you because of of the

1:00:33

content. It's just very powerful. It

1:00:35

makes all the levers uh much stronger.

1:00:38

And then sales works because it's been

1:00:40

working for like you know like the

1:00:42

beginning of time. It's just talking to

1:00:44

people and can like explaining the

1:00:46

product and like making sure that this

1:00:48

solves their problem. And I think

1:00:50

combining both you end up with like very

1:00:53

strong companies like Stripe for example

1:00:55

where it has like a very strong self-s

1:00:57

serve and like product and and marketing

1:01:00

and uh PLG uh growth but at the same

1:01:04

time of course they can support

1:01:05

extremely large businesses and like they

1:01:07

have the white glove onboarding and like

1:01:10

all the forward deployed engineers you

1:01:11

need because it I think those are like

1:01:15

the best companies and that's the way I

1:01:16

want to build chatbase is um attaching

1:01:21

a sales approach on top of a strong

1:01:24

content and product like growth.

1:01:27

>> So, okay. So, really quick lightning

1:01:29

round stuff here. Cold outbound, like

1:01:31

what's the thing that you learned about

1:01:32

cold outbound that was like the hardest

1:01:34

lesson but the most important.

1:01:36

>> Yeah, cold outbound. I think

1:01:39

it works extremely well if you have a

1:01:44

very big uh TAM

1:01:48

So like for for a company like us

1:01:50

customer like just a customerf facing

1:01:52

agent so like customer support customer

1:01:54

uh sales and and all of that customerf

1:01:56

facing interactions of course this is a

1:01:59

huge market and

1:02:01

that means like if cold outbound works

1:02:04

for anyone it will work for us because

1:02:07

like our just time is is huge and we

1:02:10

know the product works because it's

1:02:12

working with other people that are using

1:02:13

it um through the self-s serve flow

1:02:17

Um, so I think it then it becomes a

1:02:20

numbers game. Then it becomes how much

1:02:22

you're doing and how much you're willing

1:02:24

to spend. And it's just like a formula

1:02:25

at the end of the day like cact to LTV.

1:02:28

And this is the part of it where you're

1:02:30

thinking about it like maybe a B2C

1:02:32

company. Um, but but I think that's I

1:02:36

think that's like the approach of a lot

1:02:37

of companies that are starting out now.

1:02:39

And I think even bigger companies are

1:02:41

seeing this is combining both like what

1:02:45

people have been doing in B2C and what

1:02:47

people have been doing in B2B and

1:02:49

combining both for a very strong

1:02:52

sales supported organization with um

1:02:55

very strong PLG motion.

1:02:57

>> So this is a really interesting one. Be

1:02:59

friends with your biggest customers. Um

1:03:01

a lot of Solo founders I know have

1:03:03

incredibly close relationships with the

1:03:05

people that they serve. um they're

1:03:07

usually on like a texting basis with

1:03:09

their early customers. What was the

1:03:11

thing that you learned from that or or

1:03:13

what's something that what's something

1:03:14

that has been sort of surprising?

1:03:17

>> Yeah. Um I think for us it was extremely

1:03:20

important and extremely easy too. Like I

1:03:22

think maybe it's very like maybe not

1:03:25

intuitive to someone like new to

1:03:27

business to be friends with with

1:03:28

customers, especially when you're like

1:03:31

like us, we have 10,000 customers. So

1:03:33

like how are you going to be friends

1:03:34

with them? But I think for us it was

1:03:37

very helpful because

1:03:40

those biggest customers we we realize we

1:03:43

have a lot in common with them because a

1:03:44

lot of them are like executives or

1:03:47

founders or you know like big project

1:03:49

managers at a big company and a lot of

1:03:52

the problems we're facing they have

1:03:54

faced too and they have insights for us

1:03:56

we have insights for them and it's just

1:03:58

like very easy to find common ground and

1:04:00

like find things to talk about. Um, and

1:04:04

then it's very helpful because

1:04:06

you need your customers to be like brand

1:04:10

ambassadors. So you need your customers

1:04:13

to like have like you're growing from

1:04:15

word of mouth is like huge for us

1:04:17

because um we have like a lot of

1:04:20

customers in a lot of different

1:04:21

industries. And when you have like one

1:04:24

customer in one industry but they

1:04:26

actually love the product, they can't

1:04:28

stop talking about it. And then you get

1:04:29

more people from that industry. And you

1:04:33

only get that or like it helps when you

1:04:35

actually know them like actually know

1:04:37

them on a name to name basis. Like you

1:04:39

have their their phone number, you call

1:04:41

them. And we I think we we started doing

1:04:44

this maybe later than I wanted to, but I

1:04:48

now realize that this is

1:04:51

an extremely like undervalued I would

1:04:53

say growth lever that people are not

1:04:55

focusing on. So the last two here were

1:04:58

very closely tied together which is

1:05:00

pricing is the fastest lever and margins

1:05:02

don't matter early on. Could you say

1:05:04

something about those two and maybe how

1:05:05

they relate to each other?

1:05:07

>> Yeah, I think pricing is interesting

1:05:09

because

1:05:11

there's no science behind it. Like it's,

1:05:14

you know, like I consumed all the

1:05:16

content, you know, the startup content

1:05:17

about pricing. I talked to a lot of

1:05:19

founders. Like the most common way

1:05:21

people do things is experimenting. like

1:05:23

you just come up with a number, you put

1:05:25

it on on the site or like you try it

1:05:27

with a in a sales call and then see the

1:05:29

reaction. That's like the the the only

1:05:32

way people price and like doing more of

1:05:34

that is how you find the perfect price.

1:05:37

Um so I think a lot of people do not

1:05:39

realize that maybe they're pricing too

1:05:41

low and even maybe they're pricing too

1:05:43

high and they're losing out on on

1:05:44

customers. And by saying pricing is is

1:05:48

the is the fastest lever is because you

1:05:51

can just change it. you can just decide

1:05:52

to change it and immediately you will

1:05:55

see like feedback from from the market

1:05:58

and you can say the same thing about

1:06:00

like any of the other um like efforts

1:06:03

you're you're doing but pricing has that

1:06:05

advantage. So it doesn't make sense to

1:06:07

not do that. it. You should be changing

1:06:08

pricing a lot to find where the perfect

1:06:12

price is when you're delivering where

1:06:15

customers want to use you even if you're

1:06:17

expensive because you're delivering like

1:06:19

a lot more value to them. And

1:06:23

from what I've learned, like the only

1:06:24

way to find that is by experimenting.

1:06:26

>> And then that second part about margins

1:06:29

not mattering early on quite as much.

1:06:31

Yeah, I think this is more of a thing

1:06:34

that I would say to bootstrapping or or

1:06:36

solo founders especially because

1:06:39

um

1:06:41

like the definition of a good business

1:06:42

is like a business that does profit and

1:06:44

it's like when you first like see the VC

1:06:48

world is like unintuitive like how these

1:06:51

many companies are not profitable. Um,

1:06:54

so some people are like, "Oh, I'm

1:06:55

against VC. I'm going to bootstrap for

1:06:57

for some I'm not against VC. Like I love

1:06:59

I think my second company I'll probably

1:07:01

raise uh I think it u it depends on like

1:07:04

what I'm doing, but I'm saying like some

1:07:06

people are very religious about these

1:07:08

things and they decide um

1:07:12

like I'm just against everything. So I'm

1:07:14

against like profitability or sorry I'm

1:07:16

against like not being profitable even

1:07:19

if it means I can grow faster. And my

1:07:22

point here is it's much much easier to

1:07:25

cut cost than to get more customers and

1:07:27

get more revenue. So I would say like in

1:07:29

the beginning if if the goal is to like

1:07:31

just build a big brand and a big company

1:07:33

and something generational,

1:07:36

of course you should sacrifice the $10

1:07:39

in cost if it means you're going to get

1:07:41

$10 in revenue because you can like

1:07:45

cutting cost is much easier than uh

1:07:48

getting more revenue. And

1:07:51

the revenue also like signals other

1:07:53

things other than the you know like the

1:07:54

dollar amount. It signals like a new

1:07:56

customer that's going to talk about you.

1:07:58

It signals more brand awareness. It

1:08:00

signals more money you can invest once

1:08:02

you cut costs. So the money from revenue

1:08:05

is much much more powerful than whatever

1:08:07

you're spending in terms of cost. And I

1:08:09

think yeah a lot of bootstrap founders

1:08:12

don't think about things that way. And I

1:08:14

certainly didn't. And I think it made me

1:08:17

a lot more slower in the beginning, but

1:08:19

now it's much easier to be more

1:08:21

aggressive because I know that

1:08:23

>> that's really I mean that's super

1:08:25

counterintuitive and uh that's exactly

1:08:28

the type of thing that people listen

1:08:29

for. So I'm sure a lot of people will

1:08:31

benefit from hearing that. And again,

1:08:33

thank you for being on this. I I think

1:08:34

we want to close this out with sort of

1:08:36

the two customary questions that we

1:08:38

typically ask. The first one is um is

1:08:42

sort of the bare case for being a solo

1:08:44

founder. The reasons that maybe people

1:08:46

shouldn't be. Uh because I think that

1:08:48

obviously we think that solo founding is

1:08:50

great. We think that it's an incredible

1:08:52

opportunity um and that some of the best

1:08:54

companies will be built. In fact, it

1:08:56

will probably be the default way that

1:08:57

companies are built uh in the future.

1:08:59

But at the same time, it's not all

1:09:01

sunshine and and roses or whatever,

1:09:03

right? There's got to be some some

1:09:04

downsides to it. So what's the sort of

1:09:06

the case against solo founders? And then

1:09:08

of course the spoiler alert is we'll

1:09:10

we'll we'll take a pause and we'll talk

1:09:12

about that. But then afterwards we'll

1:09:14

we'll talk about the the case for it.

1:09:16

>> Yeah. I think the biggest bare case is

1:09:20

how hard it is especially in the

1:09:22

beginning. Um,

1:09:25

I think having a co-founder, having

1:09:27

someone as invested as you, as much as

1:09:30

you,

1:09:31

especially early on, just makes life

1:09:34

much easier, especially when you have

1:09:36

like trust in them and you can um fully

1:09:39

depend on them and you know they're

1:09:40

smart and like you just

1:09:43

some things in the business, you know,

1:09:44

are handled because it's with them. And

1:09:46

you can say the same thing about um, you

1:09:49

know, like any like good, you know,

1:09:51

person on the team. But I think for a

1:09:53

founder, especially early on, it's it's

1:09:56

special because a lot of the early days

1:09:58

is like you're trying to figure out what

1:10:00

you're building. You're trying to figure

1:10:01

out PMF. You're trying to get your first

1:10:03

customer. And you want someone that has

1:10:07

the same investment as you to go with

1:10:11

you through all of these things. Um, and

1:10:14

then the maybe the other

1:10:17

like

1:10:18

maybe bare case for for solo founding is

1:10:21

it just doesn't work for some businesses

1:10:23

like if you're starting a research lab

1:10:25

like I don't know how you can do that as

1:10:28

a solo founder or maybe like some

1:10:30

robotic like especially the things where

1:10:32

you need like a lot of technical

1:10:34

expertise in like very specific domain

1:10:37

um and you don't have that uh or if you

1:10:39

do have that maybe you don't have like

1:10:41

the business aspect of things. Um, so I

1:10:43

think some businesses

1:10:45

it's just harder to do as a solo founder

1:10:47

or like maybe it's maybe someone else

1:10:50

will will do it and like you're going to

1:10:51

get them on the podcast, but it hasn't

1:10:53

been proven uh that it it it's easy to

1:10:57

do uh in in some kinds of businesses.

1:11:00

Um, yeah, I think those are are the main

1:11:02

two um in terms of like downsides of of

1:11:05

solo founding.

1:11:06

>> I guess let's flip it over then. I mean,

1:11:08

I I think that by the way, a lot of

1:11:09

those things are are incredibly valid.

1:11:12

Um, especially the the sort of

1:11:14

loneliness and sort of like not

1:11:16

necessarily having a thought partner.

1:11:18

Sometimes that's valuable. Sometimes

1:11:20

it's the challenge, right? Sometimes you

1:11:23

argue and whatnot, but sometimes that is

1:11:25

really valuable and um that makes a lot

1:11:27

of sense. So, like let's let's flip it

1:11:29

over though from the bare case for solo

1:11:31

founding. Like what's the case for solo

1:11:32

founding? Yeah, I think the case for

1:11:34

solo founding is that

1:11:37

it's very hard to lose. I think like I

1:11:40

think the the companies go out of

1:11:42

business or like startups they they

1:11:44

crash because I think the biggest reason

1:11:46

is co-founder breakup because if you

1:11:49

don't have breakup you can just like

1:11:50

pivot or you can just you know like try

1:11:52

to raise more money or you can just like

1:11:55

there's a lot of other options but

1:11:56

co-founder breakup when it happens then

1:11:58

like you have to that's it like the

1:12:01

company's not going to work out um in in

1:12:04

most cases. I think I I I mentioned this

1:12:06

before. I think having an amazing

1:12:09

founder is better than having no

1:12:12

co-founders, but having a slightly like

1:12:16

below average co-founder is much much

1:12:17

worse than being solo. Um, and I believe

1:12:20

the case is like

1:12:22

you're going to end up in a lot of

1:12:23

arguments. You're going to end up in

1:12:25

like um different opinions about

1:12:27

different things. You're going to have

1:12:28

like this gray area where like it's not

1:12:31

very clear who's supposed to have the

1:12:33

final say in something. And when you're

1:12:37

not able to like work out through these

1:12:39

conversations, especially quickly,

1:12:40

because you need to move fast and you

1:12:41

can't have like threehour calls about

1:12:44

like a small decision because both of

1:12:46

you are like very uh you know,

1:12:48

hard-headed about like this specific

1:12:49

thing, then it's just like even if you

1:12:51

don't have a breakup, you're just going

1:12:53

to be much much slower as a company

1:12:55

that's just like going through decisions

1:12:56

as as fast as they can. So yeah, I think

1:12:59

that's honestly the biggest thing is

1:13:02

yeah, like co-founder breakups and

1:13:04

that's maybe it's like one reason, but

1:13:06

it's a huge reason to to not uh do it.

1:13:09

So I think

1:13:11

if

1:13:12

you don't know who that person is that

1:13:15

you want to be as your co-founder, like

1:13:16

you're starting a new company, you don't

1:13:18

know who that person is. I would highly

1:13:20

suggest instead of like finding someone

1:13:23

that you think maybe like checks off all

1:13:25

the boxes but you're not 100% sure,

1:13:27

instead of doing that, then try solo at

1:13:30

least for like some time and then see

1:13:33

how it goes because you can always

1:13:35

change your mind later. It's like a

1:13:36

two-way door decision, right? So, um you

1:13:39

can always bring in a co-founder if you

1:13:41

think it's it's too hard. But

1:13:44

yeah, that's also a good thing about

1:13:45

solo founding is the optionality. Maybe

1:13:48

this is the last the last thing that you

1:13:49

can comment on is we've we uh we we've

1:13:52

definitely covered a lot of ground, but

1:13:54

that specifically around like the

1:13:56

decision- making and sort of like being

1:13:58

the sole decision maker. Um you went

1:14:01

through a bunch of different ideas. You

1:14:03

were working on a bunch of different

1:14:04

projects. Uh maybe a co-founder wouldn't

1:14:06

have gone on all those different little

1:14:08

journeys with you to eventually land at

1:14:10

Chatbase, right? Like it feels like in

1:14:12

many ways that was a very personal kind

1:14:15

of like exploration experimentation

1:14:17

period that yielded chatbase. Hard to

1:14:20

say if you were working with other

1:14:21

people if that would have happened.

1:14:23

>> Yeah, exactly. And it's also hard like

1:14:24

maybe if I did find an amazing

1:14:26

co-founder then like I would have like a

1:14:28

much better bigger success than Chad

1:14:30

base. But it's it's just very hard to

1:14:31

predict these things. But I would say

1:14:34

like I think being solo helped a lot

1:14:38

with moving fast and just like making I

1:14:43

like the fact that everything is my

1:14:45

fault and like being solo gives me that

1:14:47

satisfaction that everything is my

1:14:49

fault.

1:14:49

>> Cool. Well, thank you so much for doing

1:14:51

this. This is great. Yeah, thanks for

1:14:52

having me.

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