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How the Smartest Founders Are Quietly Winning with AI

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Now 0 to one is very likely an AI. You

build an incredible tool that no one

else can do. You can do a million in a

week or

[Music]

two, you know. Okay. So for this

episode, what I'm thinking this is about

is this is sort of um and guys, this is

going to be generous to us, but what is

the smart money doing with AI? And you

know, in betting and sports betting in

Vegas, you always kind of want to watch

what are the sharps doing? they tend to

be just you know maybe 10 or 15 percent

earlier to to to understanding things or

to recognizing things and so similarly

uh Jason wanted you on because you've

been doing really interesting stuff with

AI both from investing you're talking to

startups that are using them you're

reading all the reports but also you

yourself built this AI tool and so I

want to kind of get your reaction to a

few of the different things can you

first explain this AI experiment you did

where you basically made a body double

of yourself out of AI and like what was

the experiment and what'd you

Well, yeah. So, so Saster has a lot of

content as you guys know. We have 12

years of content. Some of it's out of

date, right? For for sure. Saster being

um you're a previous founder who's

exited multiple software companies. Now,

you're like the godfather of like SAS

because you have this blog and media

company and events business called

Saster and you have a huge fund. So,

that's kind of the But probably most

interestingly for for like seeing the

future a little bit is I have about

10,000 pieces of content I've written

over the years. a lot of it which is not

out of date and I update it personally.

So about 10,000 pieces of content and

then we have several thousand interviews

like you guys do but with so many great

folks early ones with Darmsh ones from

Daresh. Daresh when when HubSpot had

just IPOed Darmsh the other day Yamine

last week Brian Halagan over the years

and we have all of it in RAI took

everything I've written every tweet I've

ever done every LinkedIn post every

Saster video from every speaker for 12

years. Aaron Levy the week he went IPO

for the first Astra annual to last week

when we were talking about AI, all of it

ingested in this AI. And so what I

instantly saw was as soon as I would

talk to this AI, it was much better than

me. It was much better than me because I

forget. How did you get that information

in there? You just hook up RSS, right?

Um the feed for blog. It can scrape the

web, which is pretty easy. Soon we'll be

able to do other things like MCB, but

it's just scraping APIs and RSS. It's

really just scraping. You just give a

URL. But did you use like Dely or you

you built your own tool or what did you

do? I tried a couple things and then I

used Deli and then at first we had so

much content it was a little difficult

to ingest it. So there is there is a

little bit of work and then I spend

about 10 minutes a day training it which

we could talk about. So there is a

little bit of maintenance involved but

it's better than me. And the thing I

didn't get until I saw something that

was hyperrained, like this is a lot of

content, 20 million words, right? Very

few mistakes, very few hallucinations,

and the ability to connect things that I

can't. I just don't remember. I don't

remember what Sam and I said on the

hustle on stage years ago versus when we

did an MFM a while versus today. But the

AI knows it all. By the way, 20 million

words is like 200 books worth of

content. Average book, I think, is like

100,000 words. So 20 million words

you're saying is you basically gave it

20 200 books of your own brain uh and

the brains of other guests that have

come on your show. Yes. And your goal

was to build was it to build basically

an adviser an AI version of you that

could be an adviser to a founder who

wants to come and talk to you, ask

questions, but you don't have enough

time in the day to book calls. Was that

the big idea? I just wanted to learn

like you guys did. I just wanted to

learn. I didn't think it would be as

good as it was because I used other

products and I've used other things and

it wasn't as good as my my digital AI

was. It was the use case would be what

is it? What I said or is there something

else? The other interesting thing is the

use cases with AI are much broader than

you'd expect. Okay. So, I didn't expect

people to upload their board decks

before board meetings and ask for

feedback before board meeting. That's a

niche use case. I didn't expect hundreds

and hundreds of founders to use it as

their therapists for their company where

the growth has slowed. I didn't expect

that. I didn't expect so many folks to

use it to review their um sales scripts,

their SDI scripts when there's when

there's specific tools to do it, right?

I didn't expect it's so good at

reviewing VC pitch decks. It's so good

at it. Better than anything I've seen.

Can you get tactical for one second? So,

you go to deli.ai AIH and you just

uploaded the Sasters RSS feed and it did

all of the work. You YouTube RSS,

Twitter, um, blog, but but could I go to

a health guru or a business guru who I

uh, subscribe to, who I love, can I say

YouTube.com/allexerosi upload that and

it automatically does it? Is this Well,

it's an interesting question. It is

prohibited, right? It is prohibited by

their website, their terms of use. They

prohibit it. But honestly, this is an AI

risk. You could you could do it.

Absolutely. You could do it. You could

redo what I did. It might take you a

little while longer, but you could just

clone exactly

myself and then you would you could do

it just as well as I did. Sam, I've

never felt so used and abused when uh uh

Jasm came on the podcast and she was

like, "Yeah, actually I have my team

training an AI of you so that if I'm

brainstorming ideas, I don't have to

ever call you. I'll just ask the AI what

you know, basically you'll just be in

the meeting with us." Yeah. She's like,

"We, yeah, we just took all the podcasts

and we're training it on how you think,

the questions you would ask, what you

would say, reactions you would give, and

now you're just there in the meeting."

So, she basically hired me without ever

paying me, right? Because I have this

corpus of content out there. I've

actually put my brain out there in the

public. But how do I do that? Like, how

can can I just upload a YouTube channel

and say this YouTube creator has great

advice and I can upload 800 videos and

it will transcribe all of them? I could

go to Deli. It may take a a day or two

to fully ingest all that content, but it

will do it just from the URL of your

YouTube just on deli.ai. So, I could I

could make I actually I think it is a

great product. There are other people

that can do it too that is not there are

some I'll tell you what I think is

interesting about Deli, but we're

looking at all this cursor and windsurf

stuff and lovable and like you don't

realize like they're just so far ahead

of like B2B and regular people only

because they're better people working on

them. If we had the quality of people

working at Windsurf, working on on CRM,

okay, or working on marketing tools or

podcasting tools, your jaw would drop

today. But this is why your jaw is going

to drop over the next 24 months because

just mediocre engineers cannot like the

the engineers at OpenAI are so good.

They're just so good. And so, but the

average engineer working at a struggling

CRM, right, is just not just not that

that good. But they'll catch up. But

yeah, you can build all of this. And

here's the interesting learning. So we

could build a digital SAM and and we

could do this for next week or whatever.

You can do it. The my learning from IIA

it's okay that it's not you. This is why

for example you can train your voice. It

uses level 11. Is that the product or I

get a little confused. Level 11, right?

11 Labs. 11 Labs. Yeah. 11 Labs. And

Level Labs is epic, right? But you can

choose. Do you want it to be exactly

like you? Which is what Brian Hagan did.

And then I realized that was creepy. I

don't want Digital Jason to be me. I

want digital Jason to be a prime version

of me that 90% of the time is much

better than me but is distinct. I don't

want people confused like Brian. I get

conf like Brian Hallagan. And so um it's

okay that it's not Sam. Like it could be

a version of Sam that is better than

Sam. All right. A few episodes ago I

talked about something and I got

thousands of messages asking me to go

deeper and to explain and that's what

I'm about to do. So, I told you guys how

I use chat GBT as a life coach or a

thought partner. And what I did was I

uploaded all types of amazing

information. So, I uploaded my personal

finances, my net worth, my goals,

different books that I like, issues

going on in my personal life and

businesses. I uploaded so much

information. And so, the output is that

I have this GPT that I can ask questions

that I'm having issues with in my life,

like, how should I respond to this

email? What's the right decision?

knowing that, you know, my goals for the

future, things like that. And so I

worked with HubSpot to put together a

step-by-step process showing the

audience, showing you the software that

I use to make this, the information that

I had chat GBT ask me, all this stuff.

So, it's super easy for you to use. And

like I said, I use this like 10 or 20

times a day. It's literally changed my

life. And so, if you want that, it's

free. There's a link below. Just click

it, enter your email, and we will send

you everything you need to know to set

this up in just about 20 minutes. and

I'll show you how I use it again 10 to

20 times a day. Um, all right. So, check

it out. The link is below in the

description. Back to the episode.

So, okay, let's walk let's walk through

these top 10 learnings. So, you build

this AI. Uh, it has 35,000 conversations

with people. You did it as almost 50

now. Yeah. 50,000 conversations. And

learning number one, you said users will

tell AI things that they won't tell

humans. What do you mean? Yeah. Um,

well, first of all, before we can get

there, one obvious like there's no way I

could do 50,000 conversations, is there?

Right? I'm not even a people person. I

could do like one or two a day and I get

tired. 50 thou just think about the

delta between two a day and 50,000. But

yeah, this is the thing like there are

some things that are somewhat unique

about me that are early. The amount of

content Sean like your math, right? The

amount of books we're talking about

here, right? the amount of content I've

written just about B2B, just about bis,

building business software makes it

interesting. The other thing is there's

enough people, I'm not like a super

influencer like you guys are, but

there's enough people that know the

digital me that they already know what

to ask me, right? They've already

watched me in an event. They've read the

content. So, like they ask me things

without thinking it's a prompt or

prompted. They just ask things they want

to talk about their deepest fears. Like,

I I've partnered with Sam on this

podcast, but I'm not sure he's committed

as me. I see him doing other things.

He's into this accounting software and

this Hampton's thing. I'm worried he'll

quit my podcast on me. What do I do? And

my AI is really good with talking that

through you. Right. And so people just

think to ask me things all this Sam. Hey

Jason to the heart there. Jason, you

think it's funny, but like you might ask

Hey, Jason. Jason, how about you shut

up?

Well, now you But there there are

thousands of these types of

conversations. My co-founder is not as

comm I don't know if my board's going to

fire me, right? I is is I'm only growing

18%. I have 11 months of runway. Right.

Were you Zuckerberging here? How do you

know what they were saying? Was there

some privacy here? How do you know

what's what's being said? It is

interesting. And on this app, you can

set how much privacy you want. You can

anonymize everything. Well, you can. No,

because there's different use cases. If

you're using it as a support tool, think

about it using as a support tool. You

don't want anonymity for support. How

can you follow up with someone? Right.

Right. Then there's like a therapy level

where you would want true anonymity. And

then there's like a sl everything's a

slider in AI in in a sense, right? I

think that like you said the therapy

thing as if it's like can you believe

that? And I'm like dude I use open chat

for therapy 3 hours a day. Yeah. Well,

everyone does. Like the majority of I'm

like this email pissed me off. How do I

reply in a graceful way? Or like I

argued with my wife or I'm upset about

that I'm not doing this. Like the other

day on Sunday, I saw someone who had a

super fancy home and I was like, "How do

I get over envy?" You know what I mean?

Like like that's all I use it for. It

is. And this is the same thing. It's

just because it's got the 20 million

words

for businessto business content, sales

content, scaling revenue. It's It turns

out this, and this was a surprise to me.

I didn't believe this. It's better much

better than chat GBT. It's much better.

And you you you said something like you

trained it afterwards. Can you just what

what do you mean by that? Well, how did

you train it afterwards? Well, listen.

I'm going to embarrass myself

technically. Okay, but basically those

20,000 words it you basically rag it.

Okay, you vector 20 million 20 million

take 20 million words of my content. You

turn it into a a very a database instead

of and and you just add that to chat GBT

or Claude or DeepSync. And the way you

add it and the relative weights of my

content versus the generic content

radically changes the output. Like chat

GBT never asked my permission. And it's

already slurped up all my content,

hasn't it? Every single YouTube is in

chat GBT. Everything I've written, I

haven't been paid a nickel. So, what's

interesting is that content's already

there, but by weight by heavily

weighting it toward my content for my

type of knowledge, it's much it's not a

little bit better than Chad GBT. It's

like much better, right? How do I how do

I create a sales comp plan? I have four

SDRs and five AES. uh our a our average

deal size is 2K a year and we want to go

from 2 million to 6 million next year

and and my team won't really do outbound

chatb is going to give you a very

mediocre answer but my AI is going to

give you insanely good answers even

though overall we're pulling from the

same content right and so you you had to

do that manually was that the training

or did you do more did you do more

training than just that well first of

all it auto updates every day which is

better than chat GBT or claude it auto

updates every day it slurps up

everything on my blog, on my social

media, on my YouTube every single day.

It does it essentially almost in real

time. Okay? And then yeah, you it does

it itself. It auto updates. Now, what I

do do, here's what I do do is, and I'll

tell you my learnings on my

hallucinations, okay? I audit a few of

them. I read some and I see if they're

wrong, right? I see if the ones that are

that are not anonymous, if they're

wrong. And when I see something that's

wrong, and I'll tell you what I learned

if you're interested, then I there's a

section where I just train it, right?

And I say, "No." Um, Sam and I first met

in 2014 16 after I wrote a Corora post

and he had me do a a meet up at the

hustle. Okay? Because it got it wrong.

It made something up. Okay? So, I do I

do that for about 10 or 15 minutes a

day. And it turns out it doesn't get

very many things wrong. And the things

it does, it consistently gets wrong. And

I'll tell you why. And then I just fix

it. And the next day it's right. The ne

if you do nothing and you don't train it

and you put no content in. Yeah. this B

this this average VP of sales is going

to say it doesn't work you know I I

logged into chat GPT a year ago and it

hallucinated like you're going to lose

your job but the hard the hard part here

is like so I'm so committed to chat GPT

so it it it knows so much of my

information because we've had so many

conversations it does are we all going

to have like files you know like our

health record where it's like uh you

know my the background because it sounds

like I get nervous to switch to any

other model because I'm like h chatbt

I've already asked it so many questions

it already knows everything. It's an

interesting question. Here's what I've

learned. First of all, memory is a big

deal, right? Chat could already remember

questions, but now it's remembering

everything. Okay. So, so it's a moat

from the top folks I've worked with on

this. There's on the one hand, it's a

it's a moat just like being in the

Google ecosystem is a moat just like

back being back in the day being in the

Yahoo ecosystem was a moat. Okay. But

the mode is not as deep as we think. Our

ability to get to get trained and up to

speed does not require 20 million words.

So yes, it is a moat, but if you decided

Claude was much better for you and you

the point is and you spent a month just

including your day each day, you you're

probably there. You're not not 100%.

It's enough. It doesn't Somebody had a

good startup idea. I think it was Aaron

Levy or some somebody was tweeting this.

They they were talking about Plaid for

AI tools. So basically, you'd be able to

just like the way Plaid lets you connect

your bank safely to any financial

service to be able to take your kind of

memory and context what what Chat GPT

knows about you, but port that to some

new app that you're trying without

without handing over everything, but

allow it to pull from that. And I was

like, "Oh, that's a that's actually a

very interesting idea." If apps will

even exist in the future, well, what

will exist instead of apps? Why? We're

going through a transition phase, right?

We're going through now we're chatting

once again. And we've been chatting

since the ICQ days, okay? Since AOL,

we've been chatting at our keyboards

with people. Now with AI, we're chatting

again. Okay. Uh but we're starting to

not even know where we're chatting with.

Right. Right now already like MCP is

new, but already today, OpenAI and

Claude can pull from other apps like

HubSpot and others and and Notion and

just pull the data out. I don't have to

go to Notion or even Google Calendar or

HubSpot anymore. Right. Right. As we

live in this and then, you know, people

think this Johnny thing for six

billion's crazy. It's a great bet

because we're going to go from 20

minutes a day, 22 minutes a day in chat

GBT to 24 hours a day in chat GBT. And

when we're in chat GBD, 24 hours a day,

we're not going to like pull up a CRM.

We're not going to use the interfaces

like these interfaces are all already

dying. You can see it, Sam. And the

amount of time you spend in GPT, like

then go to like a B2B app. You're

pulling your hair out. It's so dated,

isn't it? Yeah. It's so dated already.

Hey, it's only 2025 and it's already

dated to go to any B2B app. They're all

going to die. How does the excitement

and rate of change right now compared to

I don't remember if you were involved in

99 in the year 2000, but you you were

close, right? Yeah. I was a kid. It was

my first job back then. So, h how's the

because everyone talks about the dot

boom and I um I never got to I mean, I

never experienced it, but how's this

how's this today compared to then? Those

days were the f were the first time

until AI where people feel like they

could just do something out of nothing.

Like it was miraculous. It was

miraculous and that is what AI is like

today. People are just doing miraculous

things and it's exciting but man it's

super scary for incumbents. It's super

scary for incumbents. Do you think that

everybody who is maybe a content creator

at least um is going to have this sort

of like this stunt double this this

intellectual stunt double the way that

you created here? Do you see once you've

did this experiment are you like this is

the future or this was novel but no I

don't think it's going to last like you

know where where's your where did you

land after the experiment I well first

of all what I think I'm not a consumer

content creator I don't think anyone is

going to create content without AI going

forward and the tools are going to

change um like for example just for for

our last big SAS event like I did all

the speaker promos in Higsfield. Have

you ever used Higsfield? No. It's

incredible. How do you spell that?

Higsfield.A. It's the ex- head of AI

from Snap. It's one of the coolest apps

on planet Earth. Everyone's talking

about this new Google video thing,

right? But they were already doing it.

Higsfield. All you have to do to

higfield.ai is I can take a screenshot

of us right now. I'll put it in

Higsfield and it will create a movie out

of it. Okay? And it will and you can and

there's a lot of different ways, but

there's a really simple way you can do

it. You can take an initial photo and an

end photo and it will just connect them

with a narrative. So I had like I would

take like a picture of Yamin just off

her head shot off HubSpot and then take

a picture of like a stage at Saster and

it would just make a video of of Yamin

waving to the crowd and running on stage

on Saster and being excited. And so a

year ago all the all the digital promos

were a static, you know, a classic

static head shot with some chrome around

it. Today everyone got a video a really

cool video, right? Next year it will be

me and Yam talking for 10 minutes about

AI and neither of us will have had the

conversation.

It doesn't mean I won't exist, but of

course that's already come. We could

already almost do that. But I did all

these things now. I did instead of

waiting for our designer two months to

do a static uh thing and uploaded to

Dropbox and me forget where it was and

lose the URL and have to do it. Now I

just did it myself in Higsfield in like

seconds. So I'm looking at Higsfield.

This is this is insane. It's beyond

cool. It's so good. So good. This is the

This is why AI is exciting because the

really badass people can do crazy stuff

now. It used to take a badass person

like 6 months to do a prototype and then

two years to get it good. Now someone

epic like the ex head of AI and Snap can

like what you can do at Hicksfield will

blow your mind. Right, dude. I can even

tell just why the way you're talking. I

feel like if we did the same podcast,

you know, 5 years ago, your rate of

talking would have been like 10 beats

per minute lower. Even ago, there's like

a baseline level of excitement that has

just risen. Like our new blood pressure

is here. Well, as long as I've known

Jason, you were borderline grumpy. Like

you were pissed. You were pissed off all

the time. Like am I Yeah. Yeah. Yeah.

Yeah. You were like look like I remember

you you weren't tired but you were you

were tired of people asking you dumb

[ __ ] because you always had this you had

this energy of you where you were like

talking to someone and you're like

you're making a mistake. Stop this.

You're making a mistake. You had like

this like almost anger in you. Now it's

the exact opposite. Now you're you're

optimistic. I am. I am. You're right. I

I I'd like to think of differently but

you're probably right. the way you

perceive me is is important. Um it it is

I am very optimistic about it. But the

difference is I used to think all these

products were durable that they were

durable. Now I don't think any of them

are durable. So what's that mean? When I

first started doing this Saster content,

I made up this expression which I stole

from the mayor of Tel Aviv and people

have used it ever since. 0 to 1 million

in revenue impossible. We don't need

another product. Okay. 1 to 10 million

in revenue unlikely. Like there's so

much competition. 10 to 100 million

inevitable from impossible to

inevitable. We had a book that sold a

couple hundred thousand copies that was

his theme. So you go this stage because

what I learned as a B2B founder you're

saying get getting from zero to a

million is really really hard. Getting

from 1 to 10 feels impossible but once

you're at 10 unlikely but once you get

to 10 it's inevitable to get to 100. If

you had good founders it was a punch

card. Now it's disrupted. Now 0 to one

is very likely an AI. Like it's like you

build an incredible tool that no one

else can do. You can do a million in a

week or two, but like now everyone

beyond 100 million is getting disrupted.

There's so many software companies at

100 to 200 to 300 million in revenue

that aren't growing anymore. It never

used to happen four or five years ago.

Like you hit your punch guard. You had

120% revenue retention and you had a

brand. All you needed was a brand and

revenue retention and products changing

about every five years.

Right? If the product changed every 5

years and you had a brand and tens of

millions of revenue that mean you meant

you had product market fit, right? High

re like high NR meant it kept going as

an engine and this this 120 130% revenue

retention engine just kept going. It

took you from 20 to 30 to 50 to 100 and

it was like and that's why you know in

in in you know this is crazy in 2020

2021 the average public SAS company

traded at 70x ARR public in 2021 it's

it's almost imag unimaginable today when

it's at five right but it's because it

worked then like everything just worked

and now you know I I you know octa

growing 10% Salesforce growing 7% like

the they're good companies but it's not

durable the way it once was. So are

those companies I my premise or what I

thought and what Morgan Stanley I

thought because Morgan Stanley had this

report which who the gives a [ __ ] about

Morgan Stanley but they said that the

majority of uh value creation in terms

of market cap for uh AI is going to be

the big companies using AI to get better

versus new AI companies. Do you disagree

with that?

I think

that right now today as we record this

there's a hint of truth to it and and um

but Salesforce is not accelerating.

Okay, Octa is not accelerating. Lots of

folks are not accelerating. Service Now

has a lot of AI but it already had

workflows that were automation. So

people say that and there's there's

there's there's some there's qualitative

proof of it but we haven't seen it in

the numbers. Okay. So there's a window

for the big guys to leverage this

because the the interface that we talked

about is dying. People are not going to

want to use these dated interfaces

anymore. So even if it is benefiting the

big guys today, um what is the value of

of a CRM if I don't you log into the app

anymore? If I just talk to to chat GBT

and I say give me the 10 deals I have to

work on this

week. Like how valuable is one CRM over

another? or will I even know I have a

CRM? Like it just becomes plumbing in a

database. Here's one problem. Let's step

back and I'll one problem with AI. One

problem with AI is there's been too much

nerdy nomomenclature the last year. Too

many O4s, minis, 03 maxis, ll. Dude,

it's so complicated. It's like it's like

knowing the difference between an iPhone

13 and an iPhone 14. It's all that's all

going away this year. It's all that

complexity made sense. As crazy as these

numbers are, Enthropic went from 1 to 3

billion in revenue in 5 months. They

just announced 1 to 3 billion in revenue

in 5 months. Okay? And that is basically

all infrastructure plumbing revenue.

Okay? So when the inf when in the area

of infrastructure, you need to know the

difference between the models and R1 and

this. We're just starting the

application age. And in the application

age, we don't we won't care what models

HubSpot uses. We don't even HubSpot

already has a lot of AI. Do you know

what models it use? You don't care,

right? You don't care. So, so, so these

nerdy terms are going to fall away. But

what M, think of MCP as the next

generation API. And what MCP does is it

lets any AI or others talk to

applications without having to with

right inside of the AI. So, right now,

if you go to now this it's just rolling

out, but if you go to uh and you set it

up properly, and it's still a little

nerdy, okay, but right now from chat

GBD, you can change your Google

calendar. You can work with notion. Tell

me how you connect it with M. You just

it well I could I can't quite do it with

you on online. Maybe in two months it's

literally when you owe off in it will do

it automatically but I can show you

offline. You just connect it to your

Google calendar and then there the it's

still a little bit of a headache around

authentication and security like there's

a little bit of magic to go but not much

and then you can just talk to your

calendar and chat and hubspot has

announced this. So Dash is but what are

you using to connect the two? So MCP is

a protocol right? So it's like a

language. Imagine this, right? Like um

you know we have English, we have

Spanish. Then when the internet browser

came out was like, "Hey, there's a new

language. We're going to call it HTML."

And you got to learn that language if

you want to tell the browser what to do,

how to show a web page, right? So now

MCP is a new language that came out that

was basically saying, "Hey, if you're

one AI app and you want to talk to

another application, how are they

supposed to talk to each other?" MCP

became a protocol that now any app who

wants to be like yo if like HubSpot for

example they want all the AI tools to be

using to be integrating in with HubSpot

but they don't want to one by one go

work out a deal and do a technical

integration with each one so they say oh

cool we'll we'll also speak MCP we we we

understand that language we know how to

do that just kind right it's basically

like how APIs work for for most websites

but MCP is like the AI specific version

of that but right now to integrate with

and I haven't ever used HubSpot's API

but I I I'm sure It's a great one, but

but that is bespoke. Like each one is

different. HubSpot's API is different

than Salesforce and notion and linear.

You have to learn it. You have to get a

key. You have to code to it. You have to

understand its nuances. It's a lot of

work, right? Like you you may know

startups, you think you're like, why

don't you have a HubSpot integration?

Well, because it's work, right? With

MCP, it's early, but it's just starting.

It won't be any work. You just tell MCP

to go talk to HubSpot or go talk to

Notion, and it will just do it, and all

that work goes away. So, if your AI can

talk to any app you use, take all the

data out, and let you talk as a human,

for 99% of the world, we won't use

HubSpot like the way we use it today.

There's no reason to log into this app,

figure it out, like how does the UI

work, what are these tabs, how do I

configure a tab? And and the kids these

days will never know this. Like, this

generation coming up, they will never

use software like we use it. They will

never use it. What are what's the office

of open AAI like right now? Because

you're saying like, well, it sucks right

now, but in 60 days it's going to be the

best, which um is insane. So, how many

people work at OpenAI right now? And

actually, Sean, for you as well, have

you guys been to the office? What's it

like there? What's it like at that

office right now if they're able to do

all these things so fast? Uh, I think it

looks like they have about 4,500

employees. I'll tell you what's super

interesting. They only have about 60%

employee retention over two years

because what? Everyone's going and doing

their own thing probably. But it's just

crazy. Like if OpenAI only has 60% team

retention, what's your hope to keep your

your AI team? You better treat them

really

well. So I have a friend who told me

about the early days of Twitter and he

basically he had built a company. He was

like scraping Twitter and he was like,

"Oh, this is cool. If based on what

people are saying, I could figure out

what's actually trending in the world."

And the way he did it was he was like,

you know, if people people always talk

about New York, so if it's if I hear New

York a thousand times, that doesn't

actually mean New York is trending. It

just means New York's already big. But

if suddenly everybody's talking about

Tallahassee, well, Tallahassee doesn't

normally get talked about that much, but

it's being talked about as much as New

York, that means it's trending. And so

he had a separate site that was trying

to figure out what are the trends on

Twitter. Now, this they ended up getting

bought by Twitter, and that's now what

if you go on Twitter, Twitter as

trending, right? So my friend Abdur was

des I was like, what was it like in

those days? And he was like, I thought I

knew what a startup was. I thought and

and I this I related to this so much.

He's like, basically, I thought a

startup was I wake up every day and I

got to go try to get some growth and I'm

pushing I'm pushing I'm pushing the

product forward. I'm pushing the

marketing forward. I'm pushing my

product out into the market. Push, push,

push. He goes, then imagine like, you

know, you think you're pushing and then

suddenly you're pushing a boulder up a

mountain and you look up and there's a

giant avalanche coming at you. It's

pulling towards you, right? It's coming

straight at you. And so he goes, "My

first six months at Twitter," he goes,

"I woke up and I had the cruy keyboard

like imprinted on my forehead. Like I

would just fall asleep at my desk and

I'd wake up and I'm back at work,

right?" He's like, "Basically, that's

how I lived for like six straight months

because and he's like everybody's making

fun of us cuz the Twitter had the fail

whale." He's like, "But you there's

nobody had ever scaled a service like

this this fast." And so we just couldn't

keep it up. And we like we were, trust

me, we were trying. Everyone thought we

were being lazy or stupid. He's like,

"We are the smartest people. We were

trying our absolute hardest." And it was

just so so difficult. And I think what's

happening with a lot of these AI

companies is that, you know, Sam, you

and I, I think we probably only really

experienced push for the for most of our

startup career. Yeah. It's never felt

like I was holding on. It felt like I

was pushing and it got a little easier

sometimes, but it was always resisting.

Like I have this company now, we haven't

announced this, and I just were like, we

have this uh AI bot that will come and

tell us our new contracts and our new

revenue. Last week, we closed a million

dollars in new contracts in a week. And

I was like, I have never felt this level

of pull ever in any business I've ever

done. And we're not working 10 times

harder. It's just that like the market

wants this type of product at a

different level. I am sure that the

folks like, you know, Open AAI and all

these AI startups that are going they're

experiencing a startup experience that

is not we it was not anything like what

what you and I experienced, Sam. I think

it was 0 to 800 million users in 7

months. Is that what Mary Mer said?

Yeah, I think so. I just wrote it up on

Twitter. We could look or X, but yeah,

10% of the world. 10% of the world in

eight months or something like that.

Yeah. So, that's why the rate of change

is so high that everyone that's like a

lite or a Debbie Downer is missing the

point, right? And before it looked like

it was a bunch of lil's, like people

were going and testing the product, but

there wasn't really high retention. And

then they've showed that like the the

act it's not just the users that have

doubled, but the usage per user has also

doubled, right? So, you have like a a

double of a double. Um, and that's it's

pretty obvious to me now that I'm kind

of an idiot for not investing in this

company even at really any price point.

Like this is this is basically the

Facebook of this generation, right? Like

yeah, I don't think we realized that

open that chat GBT would have 85% market

share at the proumer consumer level.

That that that's what that what all that

meant surprise if we if we'd know

because ironically chat GBT was an

experiment. It was a proof of concept.

It wasn't really meant to be the product

that the the the center of open AI, but

like do you beat yourself up about this

too? Like the way I do? Cuz I'm I I just

look back. I'm like, how much how many

hours have I spent thinking about AI?

I'm supposed to be an investor, you

know, like you're a SAS investor. This

is the greatest SAS, you know, fastest

SAS growing business ever. Are you an

investor in this? Did any of you have

the opportunity to invest in it? I did.

But you could hunt it down. You know,

that's on you could. Yeah. For me, I

want to life is short. I want to own 10%

or more of a startup and have fun. So,

hunting something down just is not my

vibe. But, but it's the way to make the

most money. Don't get me wrong. Nothing

wrong with hunting it down. And and

someone's never heard of Sean or My

First Million and just getting some

money in. Like, that's the smart way to

do it. But, um I bet you u I bet you

Darm so I think on the pod Dsh I don't

know if he explicitly said 15 million,

but he sort of winked at it when we when

we said so. He owned chat.com, which he

sold to OpenAI for the what he paid for

it, which I think was around 15 million.

and he uh got AI CHP stock. Yeah,

there's a world where that becomes worth

like in the ballpark of his HubSpot

stock. I think you know that that does

probably right. I it's none of my

business, but I remember thinking with

Aaron Levy, who's one of my favorites,

you know, he was early in Stripe, early

in Gusto, like ju back in the day, Aaron

had a window before Box went public

where everyone went to him and he had a

little time like he wasn't and he just

did all of them. And I'm like, man, if

this guy did stripe in the seed and all

like how that's got to be none of my

business, it's got to be worth even more

than his box stock, doesn't it? He owned

4% of Box I think when it went public

and he's been grinding Box for like 20

years. I love him for it. Yeah. Wait, so

he he on the stripe investment. There

was a window. Listen, it's none of my

business, but there was a window. I've

been doing this long enough, right,

where before Box IPOed, he had time,

right? And then you just get you just

can't do this stuff when you're public,

right? Maybe Mark Benoff can. And so

everyone, he was the guru, right? He was

the one guy. He was and everyone wanted

Aaron. And so he would write these

checks that, you know, but I know I we

could look him up, but I know he did

Stripe and Gusto and the seed round and

a bunch of others and it's none of my

business, but I'm like that's um there

these moments in time that could be

worth more than all of his his box

shares. And uh so it just gives me even

more respect to keep going cuz so many

founders these have a different

relationship to money and investment

than a few years back. And a lot of

founders would quit today if their

investments were worth more than their

founder stock. A lot of them do quit. A

lot of them do quit. Now, you know what

this reminds me of? So, it took me at

the hustle, I think it took me three

years to get to a million subscri a

million users. And that was like

life-changing for me to get as fast as

some of these guys are growing. It's

like literally like that per hour. And

it's sort of like when you see a

billionaire who's worth like 4 billion,

like 42 billion billion, and you're

like, man, that 2 divided by 10 would be

awesome for me. Do you know what I mean?

Like it's so it's like hard to grasp how

big and how

fast how big these things are and how

big they're and how fast they're getting

that big. Well, look, it's slightly

underdised and it's a crass topic. You

might have discussed it Sam otherwise,

but like it's a crass topic. Like it's

right above, but because OpenAI will be

worth You're filthy pig. No, but when

when when HubSpot I've been around long

enough to remember when HubSpot IPOed

and it hub IPOed at about an $800

million valuation. Okay. today it's

worth like 40 billion but now like open

IO will be worth a trillion so my point

is that the rich are so much richer

right the the like the regular person's

like a little bit richer in tech and

it's great right but because the big

wins are hundred or a thousand times

bigger than just 10 years ago just 10

years ago the amount of billionaires I

wrote up on Saster the amount of

billionaires just in SAS and cloud I

could find this post but your jaw will

drop how many billionaires are in it

just because the mark the the numbers

And markets are so much bigger, right?

There's already a hundred billionaires

in B2B software. I wrote up 100

billionaires. For the people listening,

what what personality types are like who

who's poised like what 22 what does a

22-year-old today look like who can

pounce on this? Um like what's the

what's the profile type or the

personality type of of these people that

are just excelling like crazy? I think

it's just two things. Um and um the it

really probably hasn't changed since

Bill Gates days, right? Starting

Microsoft. Um but one is um you have to

be able to ship insanely good software.

Um which maybe in some business software

wasn't true for a while. Insanely good

like Higsfield that you're trying chat

GBD. This is not trivial stuff. Okay.

This is like insanely good software. And

then the second one is you have to

like be relentless to owning a market.

There was a while in 2020 21 where like

being third or fourth was

great. Hooray. Like things were so good

that like you'd be like well if I'm

number four in the market but I don't

have to sell a lot of stock and it's

calmer and I could sell my company for

400 million. That's better than IPOing.

Like the now the the best founders today

are relentless to being absolutely

number one in destroying and owning the

market, right? And because the markets

are bigger, it compounds to something

crazy, right? I mean again just one

example but Sammy and I are both

investors and owner and like you know

Adam was what whatever you know high

school dropout starting this company I

mean he's going to disrupt the entire

restaurant industry he's already on the

way there not be number

four and he has an incredible technical

co-founder now an incredible engineering

team and that product owner here's an

interesting thing because I invested in

the seed round in 2021 Adam hates it

when I say this but the product was not

very good Dean was very good the CTO it

did a lot the product but it was not

very good the reason it killed all its

direct competitors, not indirect, it

hasn't killed the big ones, is just

because the software is so much better

and that just compounds every quarter

and AI is accelerating that even faster.

So, you have to build epic software. Uh,

but if you destroy these markets, that

that's the path, but I just don't think

this is a good time to be number four. I

I could be wrong. I could be wrong, but

it had its age. It had its time. I I

actually disagree with you. I I I I I

think I understand your sentiment, which

I agree with, but I disagree with how

you're phrasing it, of uh there is it's

not great to be fourth or fifth place or

whatever. We've had a bunch of people on

this podcast that have built apps that

were really fast money grabs where they

got really big really quickly with tiny

teams. And what I would tell them, which

who what the hell do I know? But I would

tell them, I'm like, "This doesn't seem

durable, but so keep your team small and

ride the wave and take all the money and

like do do something else eventually."

But it's a little bit different than it

used to be because you don't need to

build these huge infrastructures. You

can have one hit wonders that crush it.

You have uh Yeah, I think one hit wonder

is the wrong phrasing, but I know what

you mean, which is that you can Yeah, a

base hit now can provide you enough cash

flow to a change your life and b set you

up with like five more doors, whether

it's investing or it's reinvesting into

another company you start and it you

don't have to build one 20 20-y year

durable company in order to to be a

winner anymore. So, I think I think I

understand what you're saying. Like back

when we were in San Francisco early on,

like the small lifestyle business would

get you the equivalent of a job. Now, it

gets you the equivalent, you know, like

you would make a couple hundred,000 if

you were had a lifestyle business, you

know, that was like it was working, but

it was small and it was solo and it was

bootstrapped. Now, those same solo

bootstrappers have like 8 million ARR.

So, it's just a different scale that

Okay, I remember. But you know what the

difference is though that that is I

think that term is you have to be

thoughtful about it. In the age of AI

when there's so much competition, you

can build a two or three person company

that's small but the lifestyle

businesses are being

slaughtered because when these three

kids come to SF working in the mission

and they're working 8 days a week and

they've taken your little idea but made

it much better, your lifestyle is going

to be

unemployment. So this term I think needs

to die. It it made some sense I think a

few years back. It's okay. I just worry

people are going to take the wrong

lessons from it. You have to work start

in this conversation. You can do more

with fewer people, but you better work

harder if there's comp or find a space

with no competition, right? But the

weird thing about AI is the is there's

competition in spaces that two years ago

had very little competition. Like what's

an example that comes to mind? I'll give

you an example. I in when I started

investing, I did a couple investments in

legal. I knew a little bit about legal,

okay? And no one wanted to invest in

legal. They're like, uh, it's takes

forever. Lawyers don't buy anything. It

takes forever. It's boring. It's a slow

market. Now there's a 500 AI legal

startups and there's reasons for that

but you could not be at that sleepy

pace. Um same thing I've done some of

the best investment I've done has been

in support in post sales. Okay. No one

wanted to do this type of startup.

Boring resolve tickets pick up the

phone. Right now there's thousands of

voice startups. There's thousands of

these. And so if you think you can run a

lifestyle uh customer support startup,

good luck, right? Good. Good luck

because Deli out of the box is probably

better than you. You you own a uh a

media company. You you own basically if

we uh a trade show that's incredibly

successful. So let's just categorize

that as a boring company that is not a

technology company, which is what which

is what I do as well. And uh Sean has

done something like that uh in the past

as well, I believe. For the people like

like that, how are you using AI in like

a B in a in a in a not tech company? Are

your employees now becoming

significantly more efficient? I mean, we

only have two people now. I take it

back. We have five people and we do 5

million per person now. Did you have

more people before that? We have much

more people before. We had people in

2020 running. I didn't even We had four

designers. Now we have a little bit of a

designer in AI tools. We used to have

five people on this content team

reviewing sessions. Now we have zero.

Now we just have AI. So we we have none

of the designers, none of the content

people. Uh all the ghostriters are gone.

They're the worst, right?

Well, I write my own content. Let me

drop you off at the airport. No, but

what would happen? Let me go inverse

order. Like, okay, nine months ago,

Yamin would come to a SAS event. She's

done it three times, okay? And she would

speak. And 3 months later, a ghostriter

would write up a terrible summary of her

thing. Just terrible. And I would cry

and we'd ask them to fix it cuz I can't

do everything right. And then about nine

months ago, they got better. They

actually they got they weren't great,

but they got better. And I hadn't

actually used Claude. And then I went

into Claude and I'm like this, she just

put it in Claude and they start charging

us $5,000 a month for this. So like we

can do this for 20 bucks in an hour

instead of $5,000 and waiting two weeks

with her clients, right? So we didn't

need the ghostriters we got rid of

first, right? Then we had five people.

Then we had an agency we worked with for

years and for a while it was great and

they would review all these speakers.

It's a lot of work to work with

speakers. You've done it, Sam. And when

you have hundreds and hundreds of

speakers, it's impossible to do it all.

Right. But they decided they just didn't

want to work that hard anymore. So they

they wanted to charge us two to three

times more and only do half the work. So

it just didn't help us, right? So then

we're like, we're we're so now we're

five months before SAS annual and we

just said, well, let's have our AI do

it. And it it reviewed 300 sessions, 300

slide decks, 300 presentations. Do you

have to chase those 300 people down to

give you the Yeah, we still have to like

it doesn't get rid of everything, but it

does 90% of the work. And it better And

it does 90% of the work three times

better. 90% of the work three times

better. Was that you the business owner

who had to architect and come up with

all these solutions between Amelia who

runs Saster this media business and

events and me? Yeah, we came up. No one

else was like motivated to do it. Of

course. Uh that makes sense. And uh and

then like we have a time, you know, we

have a little bit of a sales team, but

then our AI just started to do all the

screening and initial sales

conversations for us. That helped a lot

even for it's this is a very niche

business a trade show business but to

say you do 25 million in revenue with

five employees is pretty breathtaking

because I would have thought that would

be on the lower end your business would

be on the lower end of like well I still

need people but you have just proven

that not to be true and so it could do

better with more people it could do

better with more people it's not your

life your life gets worse no hon the

honest I don't mean to get off target.

The real problem is I just can't it. And

Sam, this is why you think I'm grouchy

because of early conversations we had.

I've just struggled to find enough A

tier talent that wants to do this

nonsexy stuff. Okay. I would love to

have 20 people on the team tomorrow. I

have budget for it. At least 15. Uh but

but I don't need someone that shows up

to a meeting with a sponsor and doesn't

know what we

do. Okay. I don't need a a designer that

doesn't finish the design until after

the event, which I had once in the past.

like send us a big bill but didn't

finish the assets until after the event.

I just don't need that, right? Um, you

know, I just don't I don't need I don't

need someone managing 10,000 people in

in our in our SAS annual that forgets to

do catering. Like I just don't need I'd

rather have the AI come up with the

cater the AI did our catering schedule

this year. Could you talk about the

start of Sasser real quick? So when you

started this thing you had sold your

company. Yeah. Right. Was it was it

after you sold ESOS or a long time ago

2012 but yes. So 2012, you sell your

company. Great exit. As I understand it,

you're like, "I I've retired twice. I

got in shape. I picked up a hobby and

realized, you know, like I still love

building." So So you sell your company.

Do you retire right away? Basically, you

take a break. Well,

after there's probably a little bit of

parallel to Sam here. Both times after I

sold my startups, I sort of didn't work

for the better part of a year and just

got restless for different reasons,

right? And I just got restless. And in

fact both times after about a 100 days

120 days I got a little depressed. Maybe

depressed is too strong word lost. Lost

right definitely lost. I remember uh you

know my second startup emergence capital

which is a very successful B2B venture

firm had a CEO every year had a big CEO

meetup right where they would come and

and my in my class my group I had David

Saxs um and Aaron Levy and Peter Gastner

from Viva and Reneert and then after I

got acquired I got to go to one more and

they said you can't come back anymore.

you're not you're not part of the uh

you're not part of the the CEOs anymore.

I didn't I got I I was off the team and

um you know Ben Chestnut did an

interview just a couple weeks ago with

Kleiner Perkins and said the biggest

issue when he sold Mailchimp for 12

billion or whatever it was is was he

knew he would be instantly irrelevant.

He knew he would be instantly

irrelevant. He said I am now. I'm

irrelevant now. Mailchimp's of the past.

He's like you wouldn't even build a tool

like Mailchimp today in the age of AI.

Right? Maybe that wasn't quite the

point. So, yes. So, so that was it. And

then, but then what was fun for me, and

this is is a long time ago, but what was

fun for me is because I was the first of

those CEOs like the Arenss and the David

Sachs that had an exit, I didn't have to

pretend anymore. So, I just maybe Sam

thought I was grumpy, but I just shared

every mistake I made. How I screwed up

my first VP of sales, how I screwed up

um meeting customers in person, how I

screwed up marketing, and there wasn't

much content back. It's a little

different than today. There wasn't much

content. So, everyone just started to

read this. Were you being strategic?

You're like, "Oh, I'm going to start

doing content marketing. That's going to

lead to this to lead to this." Or you're

just like, "I've got time on my hands.

I've got stuff to say. I want to start

blogging." I did what now people give

advice to, but I didn't. There was no

one to give the advice. I just wrote one

blog post a day on a mistake I made.

That was my my paradigm. Write a mistake

I made as a B2B founder that got to tens

of millions. And back when Kora was a

platform, and people listening to this

won't even know what it is, but Sam

will. I answered one question. I

answered one question. So people, this

was a way for people to ask me questions

and they those were great because they

were very tactical, right? They were

very specific. So I would do one a day

every day and it it does you know I'm a

it's a little different today in AI but

generally speaking if you do that it

compounds right it doesn't compound the

same way revenue does but if you do my

first million every week and you just

keep working at it and it does seem to

compound doesn't it? Just not in not

quite as linearly as we might hope but

it does compound. But I didn't no one

there was no advice back then. I just

did one one and one a day. You were also

one of the first people to do Twitter.

You were one of the first like uh tech

people to like you know for a lot of

tech people. Twitter didn't boom until

co um but you were doing it very early.

You know it was like you and Gary

Vaynerchuk. Twitter started with tech

people. What do you mean? I don't think

it was taken seriously. I think that uh

I think Jason looked at it as a craft

where he was like I'm going to grow a

huge audience here. I I think Sean that

for a long time Twitter was an

afterthought to a bunch of different

social media platforms. Now I think it's

bumping. I just think I approached it as

a micro blog which is what Twitter in

the old days called it. So I would put

valuable content on Twitter instead of

being grouchy or just just just you know

and so I was early to putting valuable

content I think on Twitter. Right. Um I

think if I benefited anything in content

I think it was just being early. You

were early. You've been dude you are an

output machine and the stuff that you

write about is lyrical like you write

about thing SAS is a stupid boring

thing. you write about stuff where I'm

like I don't even own a software company

but I want to I love reading what he you

know it's kind of like die workware with

clothing it's like you don't have to

know about clothing but when he talks

about ties for some reason it's kind of

exciting insight my actual real goal of

doing it was to make it more fun

building boring business software make

it more fun not not not in jokey way but

to celebrate the fun part the exciting

parts of it right that that that was my

version of what Sam said did you think

okay then I'm going to be investing this

will help with deal flow and like where

did the conference come in because

that's a pretty gang busters business. I

can't imagine you thought at the

beginning we're going to be doing $5

million per employee. We're going to do

$25 million a year in this business

where we have kind of like a little like

our monopoly. We're the big fish in this

small pond of of of basically like

thought leadership for SAS businesses.

Well, the pond there's more thought

leaders today, but if you if I mean it's

a while ago, but if you are curious, I

just wrote this just because I was blue

uh and and it was something to do,

something to share, something to add

value to the world, right? No goals. No

goals. Um I certainly wouldn't start off

with a blog today if I started off

today, right? Is as archaic it is. There

still is SEO. But what what would you

do?

Even it's not me, right? But of course,

I would do video.

I do video, but I'm not you got like

it's not my natural. I'm a good writer.

I'm not like Ernest Hemingway, but like

Sam said, I have something special. I'm

able to convey ideas in a way that helps

people in writing. And I still think

today that's a rare skill, right? Dude,

I hate video. Sean's pretty good at it.

Sean can talk to a camera by himself and

and succeed. I hate it. I hate video. I

think that like I think there's a

generational gap. You need to put a

super cut of Sam's ad reads. Oh my god,

they suck, dude. Ad reads. It sucks,

man. I I It's not I I'm incredibly

uncomfortable doing it, I think. But I

think that like the 25-year-olds today,

just like the fact that FaceTime has

existed, they're so much better at it.

Uh so there's like a huge There's a

generational gap that I'm like four

years old to have caught. But if it's of

interest, it might not be. The investing

was an accident, too. It was an

accident. I actually for about a little

less than two years, I worked at a VC

firm that had invested in me. So they

they recruited me to help them. I had no

real interest in investing. And I showed

up and I like I don't know what the hell

like this is not me. I don't know what

to do here. But luckily I'd started this

blog and founders started to come by the

office. So first the founders of pipe

drive came by the week I started and

that was my first investment that sold

for a billion and a half, right? Then

other founders started then founder of

talk desk came by. That one was worth 10

billion in it last round. Then the

founders of Alolia came by that's worth

two and a half billion. Um, then the

founder of Salesoft came by. We sold

that for 2.3 billion cash in 2021 and

they kept coming by and I'd be like,

"Well, let's just invest in these ones

because these are the best ideas I got."

Like, I'm not the outbound guy like

finding Sam Hullman. So, I just invested

in the five best guys that came by the

office the first year, but they're all

worth ended up being worth a billion

dollars. So, so that's I I only So, the

weird thing about me for investing and

then I could tell you about events real

quick, but I don't want to spend all the

time. I only I'm I'm different than

99.9% of investors. I only do saster

super fans that are high intent inbound.

I don't take favor meetings. I don't do

warm intros. Uh if you tell me, Sean,

there's a startup that you want me to

meet to invest in or Sam did, I would

ask, is this do they desperately want

me? And they'd be like, no, they haven't

heard disaster. I'm out. Right. But if

they really want me, they probably just

email me. So, I don't even want a warm

intro. I don't even want a damn warm

intro. That sounds like such a leak in

your game, by the way. That sounds like

an unnecessary bar, right? like not only

if I get a warm intro that they say this

person's kickass and they'd love, you

know, but it's like are they a huge fan?

If they're not a huge fan, I'm out. That

that just seems But the thing is like

investing so much harder than it looks.

The odds that any start like seed

startup's going to truly be worth

billions of dollars is much lower than

it looks in the media. It's really hard.

And if you don't have like if you're not

incredibly intense, if you're not

incredibly if you don't want this more

than life, you're not you're gonna

you're just gonna sell your lifestyle

business, which is very logical, right?

Oh, so you're basically saying if

they're not like basically digging my

content, they're not taking as seriously

as they should. Is that is that the

implication basically that if somebody

is seriously trying to build a

generational company, they should be

loving our content and therefore they

should want me on the cap table. I want

them sending me a cold email that is so

good that you would invest off the cold

email. This is how I invest. I want a

cold email that is so good that is so

good that you don't even need you almost

don't even need to meet them. The only

point of the meeting is confirming that

you want to invest. Like every

investment I've done that's good, I've

wanted to invest before the meeting.

Every good outcome I've had this that's

how I invested in in uh owner. I'm a

little bit after you guys, but I got an

intro that was like, "This guy's one of

the best founders I've ever met and ever

invested in, and this this company's

growing incredibly fast." And then he

sent a cold email basically right after

that, which is like, "Hey, here's why I

want you on board." And here's my last

three investor updates. And in that, one

of the things that he shared was they

had done like a hack week. So, there was

like some Loom videos of the team

sharing their hack projects. And I

actually just watched those. Yeah. And

it just show like the the caliber of the

team was really incredible. Like you can

see the caliber of team in a hack

project, right? Cuz almost by

definition, it's here's just like one or

an engineer and a designer. They come up

with their own idea. They have a very

short timeline to ship it and then they

have to pitch it and present it. So you

get to see like the the quality of idea,

the quality of speed of execution and

the quality of salesmanship all in one

from like without abstracting away the

founder. It's like that's the team

itself. And uh I emailed him back with

you know I was like we don't need to

meet. I'm in. Yeah. Hey, that's it's not

the only way to invest, but what I can

tell you is if the email is mediocre,

they're not going to make it.

There are exceptions. Okay, I know

there's exceptions, but man, wait. So,

dude, so we just um at Hampton, we're

hiring a bunch and I'm putting together

like values to look for when hiring.

Yeah. And I only made it um uh I think

I'm only going to keep it at like two or

three values, but ability to write an

email and communicate is the is one of

the three. And I will tell you of the re

one of the reasons we only have the five

people is I have lowered the bar at

Saster in a way I never would as a

software founder. I've lowered the bar

again and again. I've hired folks where

the email wasn't that great. I've hired

folks where they put an E in Saster.

I've hired folks that didn't do the

research before they started. 100%

failure rate. Like we already know this,

right? But I'm I've lowered the bar

because I've been like, well, this isn't

as cool enough. I got to take who I can

get, right? Always a neg worth less than

zero, right? Total total zero. Yeah. You

have this great tweet. You said you

think startups are about a great idea,

but in the end they're about great

recruiting. That's what you're talking

about. They they Yeah. And if you talk

about owner, not to use one, but because

it's a mutual point. I will say there

there actually lot are lots of risks

with owner. And I invested very early.

You didn't see the two times we almost

ran out of money. Now we have infinite

capital, a lot of other things. But I

actually do not know a more relentless

recruiter than Adam. I don't know a more

relentless recruiter than Adam. And that

that is a rare skill. We all learn it as

as CEOs. Like we get bet we always get

better at recruiting, right? What does

relentless look like? Like what does

that mean? Literally reach out to the

200 best people in the job. Talk to all

of them. Set up meetings. Cold, warm,

lukewarm, direct, LinkedIn. Who are the

200? Like talk to everyone in the world.

Who are the 10 200 best CMOs that I

could possibly hire? Don't pretend to

talk to 200. Don't actually only do five

interviews and pretend you're doing

them. do 200. That's what the S tier

recruiters do, right? The S tier I had

an old co-founder and I wish we'd gotten

along better, but he was one of the one

of the best I ever knew. And I'd roll

into work every day at 8:00 and he'd

already handed me two candidates to talk

to that were really good. Every day.

Every day. I've never Adam has that, but

I'd never seen that magic, right? And I

don't have that skill to every day he'd

found a way. Hey, I've got this

marketing and this sales guy I want you

to meet. Can you talk to them today? Be

like two more. But then they'd always be

great. They they're not they won't

always be a fit, right? And that's

that's how you only way you can scale as

an executive unless you have a

three-person startup. You have a few

more of these really great like how to

be a great CEO concepts. So one is to be

a great great CEO, you have to enjoy

telling the same stories again and again

and again hundreds of times. Yeah. Yeah.

Even Sam Alman does that, doesn't he?

It's pretty much the same story, right?

It it it is that that one. The one I

like that Sam does, I can comment. He

tells you the future like Elon Musk if

you're listening.

So, what do you mean by that? Well, you

know, he does this. You can make fun of

this goofy video he did with Johnny IV.

I don't know if you saw it when they did

it. Like perfect having coffee in North

Beach. My favorite romcom of the year.

Yeah. You think, "Oh, this is silly,

right?" But but listen to what he's

saying. He's telling you that in the not

too distant future, you will be on Chat

GBT 24 hours a day, right? And I'm

making the bet that Johnny IV is the guy

to do it. I'm not betting that he's

going to build a rabbit pendant. It's

not that. I'm making a big bet that he

knows UI and UX so well for the next

generation that he will solve this

problem where we are on and Sam's

already on Chat GBT more than the

average today, right? The average

person's on like 22 minutes. You said

you're on it more, aren't you? I am on

it all day. Yeah. So Johnny IV is going

to figure out a way that it's in your

ring and it's in your phone and it's in

your glasses like Ray Bandit and he's

going to figure out stuff we haven't

figured out and it's in our it's in Sean

and I's headset and we are just like

what if it was in this headset like this

is totally passive right I mean I don't

know if you guys have used granola or

the newest notion it records everything

you do all the time in the background

without permissions or visibility

you know why granola is so successful by

for note takingaking versus I don't know

if the one you said is does this Sean

but you know granola just records

everything at the hardware level Like I

could be recording us granola right now

and you we had we had we had a chief

customer office off officer summit 200

of the best chief customer officers at

Saster this year and the guy that put it

on that day wrote up the whole summary

of every single session that day like

very very good I even I couldn't do like

oh yeah I just granola just listen to

everything and it wrote it for me and it

was done that day. Do you feel this way,

Sean, where I hear this and I'm like,

this is so exciting. And then, but the

other side of me is says, um, this is so

intense. I have to like I hopefully I

can invest in something and and make a

profit otherwise I need to take my

winnings and go home and hopefully they

compound compound by themselves because

there's an intense future that you're

painting here. Like I I don't know how I

feel. Sometimes I'm like, "This is so

exciting. I want to get in. This is this

is amazing." But then other times I'm

like, "But if my life depends on this, I

don't want to play this game. This seems

so intense." I know exactly what you

mean. I've I've now experienced

basically like I graduated 2010, right?

So when I graduated I basically like

that's when the light bulb turned on. I

don't I don't I don't even remember life

really before that you know I didn't

even know the great financial crisis was

happening. I was sitting at a

Chick-fil-A somewhere in08. You know I

just was oblivious to to the to the

whole world, right? But when I came out

2010 basically three things have

happened since then that were of note.

There was mobile. So right when I moved

to San Francisco, I remember we you know

I joined Burch's startup studio and

there was a single mobile developer and

he would my very first day he was giving

a tutorial to the other 12 engineers who

were like you know super seasoned

Silicon Valley engineers but they just

never built an iOS app before. Yeah. And

I and like that ratio of like one mobile

developer to you know 12 15 non-mobile

developers. Within 12 months it flipped.

It was like if you're not doing mobile

what are you even doing? Why would you

do a startup if it's not a mobile

startup? It was like a a a dumb idea in

by the time you're, you know, a year

later into the job. And so I saw mobile

come and mobile was one of those where I

would say it was obviously going to

happen, but it was a fog of war. You

didn't know where the opportunities

were. And actually the opportunities

were very different than the previous

wave. So like Michael, who had made a

billion dollars in web 1.0 or 2.0 or

whatever, like you know the Facebook

era, he didn't realize even Facebook

didn't realize Zuck didn't build mobile

apps, right? He was like, "No, no, it'll

it'll be mobile web responsive. That'll

work." And you know, the fact that

basically Uber was like the big Uber was

like the biggest winner basically during

that like that era when we when we

launched and Uber was like physical

world interaction like you push a button

but a car has to show up and you have to

manage these drivers and that looked

nothing like the winners before. So

there was like we all knew mobile was

big but we didn't understand the the fog

of war prevented us from seeing the path

to victory. Yeah. Then the next one was

crypto. crypto had a different flavor

which was it it was not consensus that

this was going to be big. In fact, it

was very fringe and you looked a little

crazy for saying this was going to be

big and so most of us missed it for that

reason. Um and now this is the really

the third one. I I'll like take co out

uh cuz that was that was a little bit of

a different thing. Uh this is the third

one where again everybody agrees this is

going to be huge. This is going to be

the biggest of all of them. This is the

biggest opportunity ever. Right. So

everybody agrees on that, but there's

complete fog of war because like you're

saying, even the apps that are working

get disrupted. There's like so much

creative destruction there. One moment

you think it's the models that are going

to get all the money. Then you think

it's Nvidia that's going to get all the

money. Then you think it's the

applications that are going to get all

the money. Nobody knows how to win. Uh

even on the investment side, like the

VCs also, you're sitting there and you

have this really weird feeling because

you know this is the time when all the

money is going to get made. The

generational money is going to get made

now. you still have no idea where to put

it and people are trying to figure that

out in the fog of war. It's like that

Warren Buffett phrase where they where

he says um uh every every you see who's

swimming naked when the tide comes in or

goes out. You know what I'm saying? Uh

where the idea being like uh you know

when there's turmoil that's when you get

greedy but the hard part is a the

courage and b to know when the turmoil

is actually happening. You know are you

in that period now? We all know it's

happening. uh this is the time, but do

you or I have the want, desire, courage

to actually get after it? And half the

time I think, hell yeah, this is

amazing. The other half a time I think

this is this is scary and read a book.

Yeah, I want nothing to do with this.

You know, do you guys agree? There was

someone I wish I knew who it was.

Someone on Twitter had a good tweet that

resonated with me on this point. He's

like, what the the smartest play if you

can possibly pull it off today is to go

make five or 10 million, cash out, and

just chill because you can't predict

where it's going to go. like this is the

world's going to like whatever you could

do to to liquidate your assets now they

may be worthless down the road so

liquidate them right now and chill if

you don't if you don't see the future

because this is the time right I I do

think and I also think you know I used

to it wasn't until we ran our own AI

again I used to think Venode Kosa I mean

obviously off the charts smart right but

when he used to talk about how AI was

going to bring mass unemployment in tech

I used to think he was just being crazy

right but now I can see it it's also

coming I can see all the I mean Mckenzie

just laid 10% of their their team off,

but it's just a start because they put

in all of their learnings, all of their

data into their own AI like Saster and

now they just asked the they don't need

the kid anymore, right? Half of our

sales and marketing teams are going to

be gone in two years. There will be no

BDRs in a year. And so this mass change

and it is hard to make bets. So what's

happening in venture for what it's

worth? There's really two things

happening right now in venture. 70% of

the money is going into growth and right

now it's a great play. You do claude at

a billion and then it goes to three

billion and the valuation goes 5x. You

put in 200 million, that 200 million

goes to 600 million, right? You take

home 20% of the profits. You make $80

million in a year, right? That's where

venture is going. All growth. It's all

growth. And then it's doing seed early

stuff, but

implicitly people are assuming a very

high loss rate and they're paying very

high prices. 60 million hundred million

dollar valuations at seed and they're

hoping it's worth billions but they

understand like there will be uniquely

high loss rates too. They're not saying

it but they know it right. They know it.

Yeah. And that seems hard to make money,

right? Those two that combination of

high valuations and high loss rate.

Doesn't that Well, if you have hundred

billion dollar outcomes, if you get one

per funded that that's the bet they're

making that there'll be one hundred

billion outcome for each venture fund,

right? But back when hubs again when

HubSpot IPOed the bet was you'd have a

billion dollar outcome per fund one. Now

it's hundred billion per fund. So if you

believe you'll do that you can do some

you can do a little analysis or

waterfall and you just have Claude do it

for you. You don't even have to do the

analysis yourself anymore. I did this

over the weekend. You just got to find

one of them and they all the rest can

crash and burn. Right. So so what is

your game plan? I have decided

that whatever brand I still have and my

excitement and my ability actually to

know more than because I've done my AI

actually know more than most people that

aren't that aren't on the like

programming tool side. I've decided that

I'll get one at least one $10 billion

deal done in the next three years, two

years. One, no matter I I I'm only in it

for one. Whether that means I have to do

20 investments or one more, it doesn't

matter. Um I I I'm in it for one right

at the seeds at the early stage. Yeah. I

want to own I want to try to get one

deal where I own 10% or close that's

worth 10 billion. I've sort of done it

once on paper. I've done a couple

billion dollar ones and I'm just and

I've missed a lot. What would that be

worth to you if you own 10% at seed of a

company that uh outcomes at 10 billion?

Well, multiply if it's just 10 if it's

just only 10 billion. That's it. But

multiply it by 10%. So that's a billion,

right? And then you keep 20 or 25% of

that. But there's going to be so much

dilution along the way to Right. That's

what I'm asking. You don't account for

dilution. No, I'm simplifying my goal.

You could own more. Like you'll own more

and then there'll be investments that

are highly diluted. So at a at a $10

billion outcome at a seed stage, you are

looking to make $200 million.

Yeah, that would help. Okay, that would

be cool. Yeah, I think listen, if you

really want to know how venture if you

really want I know we're going off

topic. There's two ways that I think

venture works if you want to simplify a

lot of it. One, it's a great job. One,

it could be a mediocre job, it could be

a great job, or you could try to make at

least a hund00 million. I think anything

else is it doesn't exist. The g there's

a gap that doesn't exist because you're

either in it for the fees in the job

like initially like, wow, I'm a kid. I'm

getting paid $250,000 and I just get to

take meetings. It seems great. Then

you're finally a partner and you make a

couple million bucks a year and that's

like much better than like some other

job. But there's a pretty big gap

between that. like you don't it's really

actually unless you're great it's really

hard to make profits in venture or carry

so the game is to make a [ __ ] lot of

it okay and listen and the thing is if

you're in a big winner if you're in

multiple big winners just do the math

Sam like that's why most VCs make

nothing except a good salary but there

are a bunch that have made billions

because if you're in like three or four

or five of those 10 billion outcomes

which is very hard then you make a

billion bucks now the founders hopefully

make much more it is fair right but

you're either playing that game or it's

performative gamer. It's really just for

fees and salary. Like there really isn't

there's nothing in between. But you also

have the media and events business too.

So you also have this cash flow. I

assume that that's a very profitable

business. It wasn't before co but it is

now. Yeah. So you you have that either

way. Yeah. I mean I made enough as a

founder. I have a safety net. I mean but

I don't I actually view it as a net

negative for investing but it is uh but

it's a passion. Uh we we do a good job.

But yes. Last question. I I know you

have college age kids, freshman,

sophomore. Yeah. What are you advising

they're going to do when they're saying,

"Dad, you know, what should I do for a

job?" If they if they ask you that, uh,

what would you advise them to do now?

First, I I I don't think a lot of these

kids will ever have a real job. They

will find ways on the internet to make.

So, so I it is interesting. There does

appear to be a gender difference, which

I don't like, between boys and girls. Of

my sons, my son's a sophomore now. 10%

of his class didn't even want to go to

college at all. and they just decided

that they could they all had this vibe.

I'm going to go to Eastern Europe where

it's cheap and I can just make money on

the internet. I'm never going to have a

real job. There's no interest in ever

having and I don't think my son really

wants to ever have a real job. And he's

super smart. Like he's much smarter than

me. Math. He's now in he's deep in AI.

He can he's deep into cursor and wind

surf. He pays for cursor out of his own

pocket. He's writing assembly language

now so he can code to the metal and do

everything. But he'll never have a real

job. Okay. He's like worst case I'll

work for Airbnb from right. He so he's

never going to have a normal job ever.

Okay. My daughter, it's interesting.

She's at Stanford. Okay. And the vibe at

Stanford, this is if you ask, it's kind

of interesting. This is a shocker to me.

They all want to go to grad school now

as freshmen. So they're all they're all

architecting their classes, their

majors, so they can go to grad school so

they can defer

work. Like when I was in college, people

cared about grad school. Then I think

people made fun of like why would you go

go to gra like why would you go to grad

school like go go go go go go go go go

go to the internet right that was the

vibe for for 15 years now they all want

to defer reality and I don't I don't

know that there'll be any any jobs and I

don't know that people want to work I

honestly don't think and I don't mean

this negatively I don't think a lot of

the current they want to be creators or

they want to do other things I just

whatever made us want to work the three

of us I don't see it in the next

generation very rare the women want to

be educated and the men want to move to

Eastern Europe and make money on the

internet. I'm not sure it's the women

want to be educated. I just know her

group does that may not but but the men

not wanting to work at all like like

coming out of high school and just

saying no fear like no fear. I don't

know what it was like when you when I

during my life I was worried I wouldn't

have a job at different times, right? I

was worried during college I wouldn't

during I was always worried there was no

fear. When I was uh when I was a senior

in college I remember thinking man I

would kill to work at KPMG and make

$45,000 a year. Like I I I I remember

thinking like that would be a home run

if I could see your yearbook quote. I'm

like KPMG in Nashville, Tennessee. If I

could make if I could get 50 G's from

Deote, that's a home run. But it's so so

I think I don't know that they're going

to work. And then I think a lot of the

2021 generation isn't going to work

again either. I'll give you an example.

So someone I knew a little bit. Um

there's a lot So I I did this exercise.

Um I just like lowering the bar for

hiring. I did this exercise. I know I

shouldn't do it, but I want to try it

anyway. I reached out to folks that had

that the circle on LinkedIn. What's the

circle on LinkedIn? Out of work. What's

it called? Looking for work. Yeah. Open

to work. I looked I worked out to folks

that I knew a hint of a hint maybe I met

them backstage at a hustle event or

something. I I I met them in passing.

Okay. Enough that I had like a micro

connection that had been out of work for

6 months and I gave them uh jobs. All of

them in the end basically said, "I want

to make 200k or more only to do meetings

or manage teams." None of them were

willing to do any work themselves. None

of them. The people with the circle, the

young people, the Gen Z's folks their

their expect their expectations for

salary or for comp is so high. Well,

there's that, too. I'm talking about

folks that are already been out of the

workforce for 6 months, but yeah, the

expectations are they'd rather not work.

That's the thing. A lot of people would

rather not work than get their comp,

right? I mean, yeah, that sounds good to

me, too. I don't know how everyone's

like, listen, there's obviously an

element of privilege in this, right? And

for folks that are living in different

geographies or others will think this is

disgusting, and I think they're right.

But I also think folks who have made a

little bit of money in tech or otherwise

are happy to live on relatively low

amounts of money with with their savings

or others rather than just take a job no

matter what it's what what the internet

says. Right. Um Jason, is this a stupid

mental model? I do this sometimes. If I

if I want to hire somebody and I'm

interested they're $200,000 a year,

let's say, and let's say my business is

20% net profit margins. I think to

myself, this person has to basically

generate a million dollars of extra

revenue just for me to break even on

their salary. Now, maybe they're maybe

they're doing it in coordination with a

team, but like the addition of this

person in order for it to be a positive

ROI, I have to believe that adding this

person yields me a million dollars of

extra revenue. And when I do that, I

mean, 90% of the time, I'm like, there's

no chance. No, this is like that that

wouldn't even make sense here. Um, so I

don't know if my mental model is broken

or if I'm actually on to something with

that. Is that how is that is that a

really dumb way of thinking about that?

That is that is the model for sales

reps. Like traditionally a sales

executive, whether they sold software or

an automobile, a sales executive in base

and bonus would take them 20% of the

profits. If you look at how car dealers

car dealers have low margins, right? But

if you look at the margin um to a car

dealer that the the guy selling you the

the new the new Lexus net would take

home 20% of the profit to the dealer,

right? If the dealer made no profit,

they'd make nothing. If they ripped you

off and got you to pay list plus the the

CD player for $1,000, they'd make a lot,

right? Sales is the same way because in

SA in in software, the margins are

almost 100%. Reps would traditionally

take home 20 to 25% of what they closed,

right? Sales for other roles. Um, it's

really just about leverage and you're

often just hoping to break even. But

even to break even, let's say it's a

$200,000 employee, to break even, you

need a million dollars of incremental

revenue to break even on that. Yes. But

one way, this is what I learned, for

example, one way that law firms

traditionally were structured, this is

slightly interesting, and it may be

different today, but traditionally law

firms actually, most law firms, not the

big, not the litigators, but like your

corporate law firm that helps you on

stuff, they never made money on the

associates. Okay? So, why would you have

associates? I didn't know this till I

asked a partner that I work with. He's

like cuz I just don't want to do that

work anymore. I don't want to write the

certificate of incorporation for Sam. I

don't want to do the NDA. Like I don't

we don't make any money net of training

and offboarding and churn and the and

the desk and the computer. We don't make

any but I just don't want to do the

work. So for your organization you'll

also like just to not have to do the

work, right? But the problem with AI is

it lets us do more of the work. That's

the weird dislocation. So instead of

paying that person, like you can't even

find the $200,000 person dollar person.

At some point you'll just do the work

yourself with AI, right? That's the

cognitive load. Um but that's why it's

the mix. I don't think everyone can be

profitable. Some folks just have to

reduce the load on everybody else. But

AI is going to do more of it. Yeah.

Right. You're full of information. I um

you know, I think Theo Van described one

of his guests as a blind Russell Terrier

or Jack Terrier or uh No, sorry. A deaf

a what was it? deaf. Uh I [ __ ] ruined

this joke, but uh we're gonna laugh

anyway.

What was it? A

a de a deaf Jack Russell Terrier where

he like gets out of the of the car, he

like goes crazy. You can't quit stop him

from yapping. Uh that's kind of like

what you are where it's like we just

like hit record and we just like you

just roll and we just are on on board

and listen to you and uh you're the man.

you um you're just full of I think

really good comments that are done in

like strong taste and tend to be right.

Jason, don't get confused when he calls

you a a blind deaf dog. That's he's

trying to give you a compliment. That's

just he does it a little bit

differently. Yeah. Yeah. And grumpy.

Yeah. And he called you grumpy. So,

you're welcome. And welcome to the show.

There's a goodie bag for you on the way

out.

Thanks, man. You're the best. Um that's

it. That's the pod.

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How the Smartest Founders Are Quietly Winning with AI