YouTube Transcript:
How the Smartest Founders Are Quietly Winning with AI

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 Some of it's out of
date, right?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out of date and I update it personally.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
10
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.
[Music]
Hey,