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The "No BS" version of how startups are really built, taught by actual startup Founders who have lived through all of it. Hosts Wil Schroter and Ryan Rutan talk candidly about the intense struggles Founders face both personally and professionally as they try to turn their idea into something that will change the world.
Welcome back to the episode of
the Startup Therapy Podcast.
This is Ryan Rutan,
joined as always by my
friend, the founder,
and CEO of startups.com.
Will Schroeder will,
founders have never had
more ways to connect.
It seems like we've
never been lonelier.
Remote work, social media,
performance culture, AI
generated everything, and
it seems to be stripping
the, the humanity out of
our, out of our day to day.
You are one of the most
extroverted people I
know you've had massive,
uh, uh, parties, founder
dinners, all kinds of stuff.
Like I know I've been to
your house once this year.
Who else has been there?
Ryan, you're thousands of miles
away and I think you've been
there once more time than most
of the people that I know.
We've gone from like, you
know, my wife and I hosting
probably somewhere in the
neighborhood of 500 to a
thousand people per year at
our house to less than five.
Not, not with a thousand.
You're missing the, you
took away the thousand
part there, right?
You, your
visit represented 20%
of our attendance.
And it's interesting, like your
kids don't count.
Will I feel like I might
be higher than them?
They are taking up more space.
But that, I mean, what's what's
fascinating to me, I. Right
now is that we're at a moment
we're getting connected to other
humans has never been easier.
I mean, like you are
connected almost whether
you wanna be or not at at
the most epic level, right?
We're overconnected if,
if we can put it that way.
And yet founders who've
always had this really
isolating journey.
The nature of, of what
we do is very isolating.
It's so unique to us and a lot
of people don't understand it.
They've never been
more isolated.
When I talk to founders nowadays
and I, and I say, Hey, and
I always, you know, you and
I always check in on them
personally, it's always a big
part of our discussions and they
say, you know, where are you at?
Who are you talking to?
More and more, I'm hearing
people say, I'm really alone.
And I'm like, what
the hell happened?
I think it's important for, for
all of us and the, the folks
listening and, and Ryan, you
and I in this, uh, episode, to
unpack why this is happening.
Also point out why
it's getting worse.
Yeah, yeah.
Right.
Like the horizon
don't look good.
More importantly, what we can
start to do about it so we
can become less detached, more
connected to other people and
feel less isolated as a founder.
Yeah, man.
It's interesting 'cause we've,
we've done an episode before
on like the, the isolation
that comes with being a
founder just from being at
the top of something where
you, you don't have peers
within the organization.
Right, right.
And that's part of it.
But I think the thing we're,
we're gonna dig into today
is how much worse that's
gotten and some of the
causal things behind that.
So what do you, what
do you think is the,
the, the first driver?
What's the, what's
the big one for you?
I think we gotta
start with work from home.
Like, I, I mean, because
it was global, it happened
to everybody all at once.
So it wasn't like a, a specific
phenomenon in particular
within the startup community.
It fundamentally changed
the office place.
You know, uh, I had a founder
call me, this is so timely,
like an hour ago, and, and
we're talking on the phone.
Good friend of mine, a, a
guy that, you know, he raised
a bunch of money and he
just, uh, leased an office
space in San Francisco.
Okay, now get this.
I get this.
He's like, yeah, you know,
here's what we paid per month.
I was like, wow, that's
really low per square foot.
Right?
Like, like for anywhere
much less San Francisco.
We were the buyer.
We were the, yeah, exactly.
Exactly.
And, and then he, he
mentioned without realizing
the significance of it, and
he is like, yeah, and so we
signed our two year lease.
I was like, wait, what?
Huh?
Uh, you signed a two year
lease in San Francisco.
I, he's like, yeah, I mean,
it's the only lease he's
ever signed in San Francisco,
so, you know, and, and I was
like, dude, if you went back
just four years, you'd be
lucky to get a 10 year lease.
10 year.
Yeah.
Yeah.
Nobody's pushing
a two year lease.
Massive lease.
If you could
find office space at all.
Oh, I'm sorry sir. WeWork
is down the street.
Right?
That's what they would tell
you with a two year lease.
Exactly.
Didn't, that'd even
more expensive.
The reason I say this is
because clearly startups
have abandoned their offices.
En mass in order for that deal
to even be, and he said that
office was sitting in a, in a
pretty prime spot for two years.
I mean, there crazy.
There was even just a few
years back, there were
people like pre-leasing,
getting rights on leases.
Yep.
Years before it was available.
Lease
futures, who knew?
Yeah.
Pretty much.
And so, but, but, but what it
points to is just the impact
that COVID and then the work
from home culture has had in
how widespread it is now, Ryan,
we were way ahead of this.
Uh, we, we started work
from home 15 years.
I mean, 10, 15 years ago.
I mean, like since
the beginning.
Yeah.
I would say like there,
there's been at least some
work from home components.
Going back at least 12
years, maybe 13 now.
And, and I say that 'cause
I wanna talk about what the
cultural and kind of personal
transition became as we
went from partial work from
home to completely remote.
Yeah.
So partial work from home,
just for, for folks listening,
the partial work from home
was early on we decided that
on Wednesdays we would create
work from home Wednesdays.
Yep.
And if I timestamped
that, that's like 2012.
That's a very long time ago.
Yeah.
It was 12 or 13 and it was.
It was just intended
to be, well, we tried
it for the summer.
Remember?
It was like a, it
was a summer break.
Let's see.
Let's see what happens.
Let's give, let's give the
team a, a chance to try this.
And everybody loved it,
obviously, because, uh, it,
it helped break things up.
You know, you only had to
go to drive to work two
days in a row, ever in.
With that though, we are still
a, an office, um, based culture
and I wanna talk about what
came with that, that we've
lost and just everybody's lost.
Right.
What came with that was for
me, and I'm interested for
you, was just forcing me
to get up in the morning
and shower and go somewhere
like, and be presentable as
a human being to other human
beings like that alone was,
was an important part of me.
Like, I'm a motivated
guy, so it's not like I'm
sitting in bed otherwise.
But like, just knowing that
I had to go present myself
to other humans, especially
as a manager, mattered.
Like, like it
changed my outlook.
I didn't feel alone
because I was knowing, I,
I knew I was going into
a room of other people.
Now when I get up and I
don't shower and I'm in my
sweatpants and I'm not gonna
see another human being in
person, you know that my
family for an entire day.
That's way different.
That does get lonely.
Yeah, it does.
Yeah.
It starts to, you start to
become quite isolated because
of things like that, and
it's easy to fall into that,
and then just that becomes
the, the absolute norm.
I think that was right.
The big thing for me was
that like a day or two here
or there, like that didn't
have any impact on me.
Zero.
Mm-hmm.
Right.
Like, okay, cool.
I'm not, I'm not gonna get
dressed there or whatever.
But what's interesting for me,
and I'm curious to what, what
your, your changes have been.
I have replaced some of those
routines with other routines.
Right.
So other things came
and fell into those
places, took some time.
But things like
meditation or breath
work, practice, uh mm-hmm.
Things like getting up and
making lunches for my kids
in the morning, which I
clearly don't need to do.
My, my, my wife and I.
Either one of us can do that.
Uh, at this point the
kids are old enough, they
can do that themselves.
I like doing it and I
think part of it is.
That sense of ritual in the
morning and like this is the
beginning of productivity.
I'm creating something,
it's gonna be beneficial
to somebody else.
And so I think in my case, it's
just been a matter of replacing
those, but pretty arbitrarily.
Mm-hmm.
I think as those things went
away, something else had to
come in and take its place.
Um, and at some point it
kinda didn't even really
matter what it was.
They just, right.
I gravitate, food is one
of my love languages.
Right.
I like to feed people.
Yeah.
And so for me it was
pretty obvious, like,
let's just go make food.
Let's make a great
breakfast, great lunch.
That works.
You know what's interesting
though, again, kind of mapping
back to founders specifically,
you know, when you and I would
go in the office and we'd be
with other coworkers, leadership
team members, et cetera.
Yeah, yeah.
You know, we'd sit in
a conference room from
time to time, we'd like
go to lunch every day.
Like we had a lot of
interaction where like
just daily frustrations
could easily be surfaced.
Vented, yeah.
Yeah.
And kind of moved on.
Yep.
Everything sort of happened
through osmosis.
The good and the bad.
Yeah, like a lot of the, I think
just the little social cues
that I had come to rely on.
Right.
Like, like even things
like noticing that
someone's having a bad day.
Yeah.
Just their body language.
Just kind of, you know, how, how
they're responding, et cetera.
And being able to like lean
in on that a little bit.
I always send a frowny face
in Slack when I'm having a bad
day, so that, you know, well,
what are you talking about?
It's, it's obvious.
Yeah.
I mean now you, you got me now.
I, I just didn't care all along.
Uh, but like I i's, like
now I have no idea how
people are doing now.
This isn't to say like,
Hey, why can't you ask them?
It's because there's a
different level of decorum.
Well, there's also a
difference between observing
something and having to ask.
Right?
If I have to ask how
you're feeling, that
leaves it up to you.
But when, when there's no
chance for interpretation
or there's the chance for
interpretation rather, and
I can just sort of see like
your body postures different.
Your body language is different.
Your energy feels off.
Uh, you didn't brush your
hair and you came to the
office anyways, like,
what's going on bud?
You okay?
Right.
You can do that.
Do you remember?
I mean, I, I know you do like,
uh, way back in the day when
I was going through all those
health issues and like I was
on so much medication that
I, I actually, I couldn't
sit up anymore and I'd have
to, like, we spent a lot of
time time in the conference
room.
Exactly.
Like I remember we'd
have these meetings.
Ellie and, and I talked at
one point about mounting
a whiteboard on the
ceiling above the couch.
Nobody could lay down the stare
like a planetarium slip up guys.
Yeah.
But like, I mean, I, I was
on so much pain medication
'cause I was in so much pain
that I couldn't function.
Imagine you guys never saw that.
Okay.
Like never saw me in that state.
And we're just wondering
why, like, I, I couldn't
respond on Slack or anything
or anything or on Zoom or.
You know, whatever our, our
tools are, I wanna map that
back to my feelings of, you
know, uh, how that makes me
feel as a founder as being, you
know, uh, isolated, et cetera.
When in that case, it
was a health issue,
which I would argue that
nearly every founder has.
But in that case, it was a
health issue when no one can
even be around you to notice
that you're in pain, right?
Whatever form that takes
and respond as a human,
that's isolating as hell.
It is.
Just the, the, by virtue of
being seen, because then you
know that people can observe it.
You can do, and, and we do
these things consciously
or subconsciously.
We send little cues that like,
I need to be seen right now.
I need you to understand
that I'm going through this.
I need you to see
that I'm happy.
I need you to see, like, great.
You come into your old
bubbly, you're like, well,
you've got something you
wanna tell the world, right?
Something good happen that
you want to share, right?
Conversely, when the other,
when there's something that you
don't feel comfortable sharing.
You want to have it
drawn out of you.
That needs to be observed too
when you're on your own by
yourself and nobody can do that.
When you can't be seen.
It creates this additional
burden of having to force it
outta yourself, having to share,
saying, Hey, I don't feel good.
Hey, things aren't going well.
And and particularly like,
again, if this was a part-time
thing where it's like, okay,
every once in a while we're
remote and I have to do that.
Yeah.
When it becomes every
day, everybody's in
that same situation.
So there isn't this other
opportunity like, well,
because you observed them
doing that, now here's my
chance to share my piece of it.
It doesn't work
like that anymore.
There's, there's another side
of it too, which is when you're
in front of people and you
do or say something that they
appreciate, you get a bit of
a, a, a, a visual, emotional,
social cue that tells you,
you did something right.
Like some, one of the things
I, is that what the bacon
icon's for in Slack?
Exactly right.
Like when I was in meetings,
I always tried to go outta my
way to like compliment somebody
or tell them that they did
a good job with something.
'cause I knew it was
important to them.
And I do that now in Slack,
but it, it lands so empty it
does not hear the same at all.
Not at all.
At all.
Um, and, and, and here's what
I think about it goes the
other way too, when someone
would say, Hey, you know, I
really appreciate you helped
me with this, or, thanks
for the raise, or, you know,
whatever like that as a founder.
I need those cues too.
Like it helps to know
that I'm doing a good job.
Yeah.
My default assumption has always
been in my 31 years is that
everyone hates me and they just
tolerate me because of that.
Having no cues to tell
me otherwise is painful.
Yeah.
Now I'm used to it, but
if I were three years in
my career as a founder.
And I had no way to get a
social signal from humans,
my, my fellow humans.
Yep.
That they're really
happy with me.
Right.
Without, like, surveying them.
I think that would be very
isolating after a while.
It is.
I I, this was a, a conversation
that came up a couple weeks
ago in, in one of the founders
groups, and it was this
notion that somebody brought
up was like, it's never been
easier to start a, a startup.
It's never been easier.
Right.
We have all these tools,
all this stuff, and I said.
Yes and no, and, and I brought
up this aspect of it was like
yes and no, because there's,
there's so much noise,
there's so much isolation.
Yes.
The technical side of things,
the product build side of
things, um, the content creation
side of things, yeah, you've
got some tools now that make
that a lot easier, but I would
argue that especially for early
founders, young founders, first
time founders, the human aspect
of it has gotten so much harder.
The idea that we would
have a meeting where not
everybody was sitting in
the same place in 1998.
Whatcha talking about, like,
of course we're gonna be
sitting in the same room.
That's nuts.
But we have all these tools
now and you know, you, you
said Slack, but I, I wanna
call it even like Zoom,
where we can see each other.
We're using it right now to
record this podcast, but it
still hits different, right.
I, you still don't
get the same cues.
And I, I think back, I'm like.
Okay.
I'm not gonna say I have no
fond memories from a Zoom call.
Some stuff has happened on
Zoom calls that were great.
I have a thousand fond memories
from like crappy interactions
in our office kitchen right
over bad coffee, right?
Yep.
Because I. We were there, we
were present, we were social,
we were, we were together.
We could read the cues.
You know, it's funny you should
say, I, I've always had this
thing where I think about how
much time I spend in a digital
world, and I've been a digital
native since the eighties.
So like, I've been at
this for a long time.
Yeah.
And, and I've played countless
hours of video games.
And I, and I, and I think
about how many of those video
games do I have a lasting,
like highlight, like life
highlight reel from Yeah.
And, and what's funny is
every single one that I could
come up with where I tried
to remember like a meaningful
moment, a memory where I,
where I played a video game,
nearly every single one of
those memories had to do with
the person sitting next to me.
Yep.
When I was playing
it like I like.
You probably remember the
time that you finally figured
out how to beat King Hippo
and Mike Tyson's punch out.
Right.
And I remember Jay Faan
like had just unlocked it
'cause he'd figured it out in
Nintendo Power Magazine and
like that was a big moment.
Yeah.
Yeah.
That's, I can't tell you any
Nintendo power like I got, but
it, but it was more about two
of us in a sleepover having
like this, you know, this.
Fun time.
Same with Zoom, same with
digital media as a whole.
Think of how many memories
you don't have by scrolling
through social media.
I mean, that one time where I
was, I was scrolling through
social media and had the
best time of my life, right?
Like happens.
Never.
No, you're just, you're
pouring dopamine in there.
But to know no end, I think
it's, it's interesting.
I think that.
Again, you and I have been
in the part of the digital
world since the digital
world became a world.
Right?
And so originally the digital
piece was a conduit to
experiences, mostly with other
people, to your point, right?
Like it was the memory of
finally making it past that
level in Sylvania, or, you know,
trying our hardest to, to make
it further than the first level
in contra with only three lives.
And then all of a sudden
the digital piece became the
experience as opposed to being
a conduit to the experience.
And I think that was where
it really started to change
and become something that
was less, less palpable,
less social, less.
Less everything.
Let's isolate that.
Let's, let's say, yeah.
The, the isolation quite
literally of us from other
humans on a daily basis
has really locked in this
sense of not just physical
isolation, but mental isolation.
Yeah.
Which is keeping us from having
a lot of the little interactions
that actually did keep us going.
Now you're gonna hear some
folks, uh, say rightfully so.
It actually worked out great
for me because I'm an introvert.
I hate being around other
people and that did nothing
but create anxiety for me.
Awesome.
I, I'm, I'm, I'm
glad that's a fix.
But I'm saying for a lot of
people, whether they realize
it or not, particularly people
who've never had an in-office
experience, it's not the office
that, that they're missing.
It's the interaction with
humans forced or otherwise.
The office itself usually
sucks.
Yeah.
The science is there,
productivity's higher.
Lots of, lots of good things
happen with, with remote work.
I think there's a couple
of flaws in all of this,
which one of them being
this is still a very, very
recent thing for all of us.
Yes.
Right?
Yep.
Even, even for you and I,
and we've been at this Yep.
Uh, you know, we've been doing
the remote thing for, for longer
than most, and even there, it's
still, you know, we're still the
first generation at, at at, at
best, and most people have been
doing this since the pandemic.
So we're a couple years in.
So I think there were
productivity and there was all
these things that did happen.
But I feel like the social
degradation piece of it,
the, the isolation piece is
something that builds over time.
I don't think we're
fully recognized exactly
what the downsides are.
I agree.
I agree.
So, uh, let's move on
because I, I think that
one is very obvious.
I mean, it's very visual,
it's very visceral.
The other that certainly came
before it that I think has
sadly done far more harm than
good would be social media.
And, and, and the idea.
Of replacing our interpersonal
connections with a digital one.
Yeah.
I thought you were gonna
say motor cars, but Yes.
Social, social
networks probably.
Now, here's the thing, I'm
not anti-social media, but I,
I think we, we've definitely
come to a milestone point with
social media and I think it's,
it's becoming well recognized.
It's really messed us
up in a lot of ways.
And I think one of the
biggest ways, it gave us the
illusion of connection without
actually having connection.
Yeah.
It gave me the illusion
that such a super level, I'm
connected to lots of people.
Right, right.
I had an in-person relationship
that was meaningful and it
was, you know, and, and, and
there were memories attached
to it, and it got extended.
By virtue of, of social
media, like, you know, I could
stay in touch with friends,
family, whatever, but it
never got really improved.
No.
At best they were updates,
but the relationship
itself never got better.
Yeah.
I think the idea that, that
we increased the frequency
with which people could sort
of tap into our lives and see
the stuff that was happening
got traded for, for the depth.
Right.
We took, we, we traded
superficial frequency
for, for true depth.
I remember it was probably
the third or fourth time.
I had asked this question, heard
some version of the same answer.
It was like, oh man, when
was the last time we talked?
Right.
They just all of a sudden
like realizing it had
been a long time since
I talked to this person.
They're like, oh yeah, but
I keep, I keep tabs on you
with, uh, via Facebook.
And like the first time I heard
it didn't really register.
Second time,
probably third time.
And then all of a sudden,
like third or fourth
time, I'm like, I. Shit,
something's happening here.
Like we are, we are not
talking because we don't
feel like we have to anymore.
Like there, there's this like,
fly on the wall ability to
sort of see what's going on.
And that's, that's enough,
except that it's not right.
It's absolutely not.
Let me dig into that a little
bit more because we're trading
different types of interactions.
Yeah.
Dramatically.
And it has a, a strong presence
to it and not a good one.
For example, back in the day.
You know, when we were hosting
all these events, we had
thousands of people at, at our
house, most of 'em founders.
We'd spend time at cocktail
parties and you, you'd hear
the, the emotion and the
excitement and the terror
of other founders and what
they were going through.
And you know, one of the
things we did for decades is
we'd get a bunch of founders
in a room and we'd just.
Talk shop.
Everybody would just talk
about what they were working
on and what their concerns
were, and they were the amazing
conversations, wildly connected,
built friendships overnight.
Like it was incredible, but
every had everything to do with
being in front of other people.
When we tried to replicate
that, which we did, I mean,
we specifically tried to
replicate that like same idea
with doing it all digitally.
We struggled because all of
a sudden the, the lack of
presence made it more difficult.
The communication channel
was there, but there
was something missing.
I
think part of it became that
like vulnerability went away.
I think it's a lot easier to
be vulnerable in, in person
when you can see the reaction
to it and you can control
how many people see it the
minute you post it on a
social, social media, right?
It's, there's no control, right?
I'm vulnerable now to anyone
who happens to come across
this, and so everybody just
started posting the positives.
And so good news guys, there's
nothing bad happening to
founders anymore at all.
We don't have to have
dinners and talk about it.
The downside, 'cause
everybody's just kicking
ass and taking names.
Fantastic, right?
That's what it felt
like for a while.
It was like just everybody's
Instagram version of
their startup man was
that bad for everybody?
I.
You know something that's
really funny about everything
we talk about here is
that none of it is new.
Everything you're dealing
with right now has been done a
thousand times before you, which
means the answer already exists.
You may just not know
it, but that's okay.
That's kind of what
we're here to do.
We talk about this stuff on
the show, but we actually
solve these problems all
dayLong@groups.startups.com.
So if.
Any of this sounds familiar.
Stop guessing about what to do.
Let us just give you the answers
to the test and be done with it.
The performative part has
gotten geometrically worse
with time and, and because
it compounds on itself.
Well, if everyone else, all
my other friends are saying
that, that, that they're having
the best vacations and best
spouses and best whatever
in their life, then I guess.
I have to, and when I
get a chance to respond,
I'm gonna make mine as
over the top as possible.
I need the best possible photo,
I need the best possible filter.
Yep.
I need the cutest possible
caption, you name it.
Right.
And all of these things
are performative, right?
I'm, I'm doing it because
I have to perform now
to, to an audience.
You leave that spotlight on
24 7 and you keep perpetuating
that, that doesn't lead to
a positive place because.
Newsflash, if you're a founder,
you are not happy all the time.
You're depressed as fuck, right?
And I think, uh, part of the
challenge is we've now got
this distorted reality around
us where it's compounded.
Every person that I'm seeing
in my feed is doing amazing.
And so immediately if I go
through my feed, actually,
uh, I hardly ever use
social media, truth be told.
And sadly, I don't wanna
call myself selfish.
I'm just doing other stuff.
I never look at
other people's stuff.
I have no idea what my friends
and family are doing, like
on social media, media, at
least the Facebook version
over the Instagram
version of it.
Twitter version of it.
Yeah.
I'm the same.
Yeah.
I, I just, I just,
I just don't care.
Uh, not I care
about those people.
I don't care about
following all those updates.
Yeah.
And so anyway, when I do go on
there and the rare times where
I'm actually scrolling through
my feed for something and I see
what everybody else is doing.
My first thought, because
I'm kind of cynical, Ryan.
Bullshit.
Bullshit.
Bullshit.
Bullshit.
It's bullshit.
Yeah, bullshit.
It's bullshit.
Bullshit.
Like, like, oh my God.
You've got the, the photo
of you and your family.
Like, dude, I talked
to you a week ago.
You hate your wife.
Yeah.
Yeah.
Nice, nice,
nice, nice photo though.
That's great.
Yeah.
But, but you do have a nice
autumn scene where all of you
are, are in an orchard somewhere
and uh, is a healthy pumpkin.
Look at that.
Yeah, with a very healthy
pumpkin, so you must be good.
But what I'm saying is like,
and then everyone's best meal.
Everyone's best vacation.
Yeah.
Everyone's best.
Everything.
And so you look through that
and you're like, oh my God, my
life must suck by comparison
because yeah, the contrast
becomes really dangerous,
but you know, it's bullshit.
Yeah.
But you can't ignore
it either, right?
Like this is what
seems to happen.
Like we, we, we do know, and
yet somehow, psychologically,
we still don't internalize that.
So.
What are some ways,
because I think this is a
particularly important one.
Look, I the work from home
thing, I'm not sure there's
that much you can change there.
I think there are some things
you can change within social,
uh, social media, but maybe
even more so like, how do
we start to carve out some
some safe private spaces.
Uh, you know, is it, is
it going back to doing
the small dinners thing?
You know, where do we get
the unfiltered talk again?
How do we do this?
I'm going through
this as we speak.
Uh, right now, uh, I'm going
through all the people that
I wanna stay in touch with.
I'm basically just creating
a giant list of people that
I'm gonna text and call like
a catalog of like faces,
like a, a book of fa like
a Facebook facing book.
Yes.
But, but instead of like
going through feeds and
everything else like that.
Yeah.
I'm gonna make a
concerted effort now.
Now here's the, the,
the key word there.
Effort to make sure that
all the people that I care
about, that I'm actively
reaching out to them.
And typically when I reach
out to somebody, we end up
following by grabbing a lunch or
a dinner or something like that.
Yeah.
It has occurred to me.
I, I'm declaring
relationship bankruptcy.
I. Which is to say I no
longer believe that I can
develop or sustain any of
my relationships digitally.
Yeah.
Yeah.
I just don't believe
It doesn't work.
It doesn't work.
I can send messages.
I can create updates.
I can follow updates.
I don't actually think
that I'm gonna build
a better relationship
with anyone in my life.
Digitally?
No, I think it goes back to
what I was saying before,
which is that digital used
to be the conduit, right?
So we would, we would
message somebody and say,
Hey, let's go grab dinner.
Right now, it's just, Hey, I saw
that dinner you had last night.
Those appetizers look
great on Instagram, right?
I think over time it's just
taken such a different form that
it's not, it's really keeping
us from taking that next step
and connecting further, which,
like I am, I'm super excited,
you know, I've been isolated in,
in two ways, and you know, the.
Work from home piece, but that's
been, that's been a long time.
But being here, you know,
we've been here in Antigua,
uh, for seven years.
It's not a hotbed
of startup activity.
Right.
I have good friends.
I've, I've, I've built great
networks here and we do a lot
of interesting things together.
And I do have some other
founders around, but it
is not the same thing.
It is absolutely
not the same thing.
And so as we're, as we are
staring, you know, we're
as, as of this recording 23.
Days away from
heading to Madrid.
Um, I've already started
setting up founder Coffees,
lunches, uh, some people within
the startups.com network.
Some people without, I'm
super excited about it, right?
So I think this is me.
I also like, I. Not only did
I have to de declare, uh,
relationship bankruptcy, and I
had to, to restructure in a way
required actually physically
moving myself somewhere
where it's more possible.
Yeah.
I gotta tell you, every time
I make a concerted effort,
like I, I, I get on the phone
with a, with a friend or you
know, I meet somebody out or
whatever, that fills up my
bank account of contentment
of I guess being seen.
If, if you wanna say,
that's the thing.
So much more.
In fact, it gets.
Zero filling when, when I'm
trading a DM with someone.
Yep.
Right.
Like I kind of look at all
of those things like dms, et
cetera, like the equivalent
of, of when you get a
calendar invite from someone.
Yeah.
Yes.
It's a piece of communication,
but it doesn't mean anything.
No, it doesn't.
Until you actually, it
should just be the preamble,
right?
This is just the Yeah, yeah.
Yeah.
Again, I understand it works
differently for everybody,
like, you know, we're coming
from a bit of a different
generation where that was, uh,
we, we can see the contrast.
Maybe a little bit differently.
Whereas someone growing up
with all these tools right now,
and it's all, they know, their
level of what a relationship
means is gonna be dramatically
different because their level
of relationship might mean we
do talk every day on dm and
that is how, that's how all
my relationships are built.
So why would that be
any better or worse?
Which I'm, I'd be really curious
to dig into that at some point.
Uh, but we'd need some
people on here who are kind
of native to that epoch to
be able to say that like.
Yes.
And those do fulfill me.
Like is it, is it the contrast?
Is it the delta from what we
knew to what we have that's
bothering you and I or are they
gonna experience the same sort
of superficiality and, and same
challenges that that we have.
I think that in person, not
with everybody, obviously,
but I think in person you
get a level of vulnerability
and authenticity that is
yes, really difficult.
To replicate outside of
that, not impossible.
Yeah.
Again, and, and different
people have different
ways of communicating.
I could see somebody else
coming on and saying, you know
what, I see the polar opposite.
I'm really nervous when
I'm around other humans.
I can't express myself.
But when I go to a, a forum
where I can be anonymous,
read Reddit and say exactly
what's on my mind or, you know,
share, I feel so much better.
And that fills me up, you
know, in, in, in my way.
I could get that.
Yeah.
Uh, I get that.
Just how I feel.
Yeah.
It hasn't worked
that way for me.
Uh, you, you said
two, two words.
One, one of 'em we had talked
about a bit earlier, which
is vulnerability and the
other one was authenticity.
Man, for as much as I am
enjoying what's going on
with AI right now, holy shit,
does AI could also stand for
authenticity incinerated.
Right.
Exactly.
What it feels like.
It just, it is stripped
away so much of the
humanity, I mean, it.
I've watched it, you know,
I've used it to write things
and just like, oh my God.
It completely vaporized
my personality outta
this piece entirely.
Yep.
Made some good
grammatical corrections,
but my God, I'm gone.
I'm gone.
This is gonna take the other
two categories we talked
about, about, you know, work
from home and social network
and be a hundred x worse.
I wanna preface that.
Preface that by saying, and it,
Ryan, I think I speak for you.
We are huge fans of ai.
Right, so, so this isn't
one of those cases where
like, we're about to go
on some anti AI ramp.
This is, no, AI is awesome, but
we got some bad shit coming.
Yeah.
And it's not just the the,
we're all gonna be living in
the matrix kind of version.
Oh, that's probably
gonna happen too.
It's something that, what really
concerns me is that we are now
taking away tons and tons and
tons of human interactions.
And we're not replacing
them with anything better.
Now, let, let me be specific.
Yesterday I was on, uh,
hold with my bank resolving
some issue, right?
And I talked to some customer
service rep, and I, I always
do a thing with customer
service reps where I always
try to make them laugh.
Yep.
I know that sounds odd,
but I picture those
people hating their jobs.
I remember when I used
to have to make a hundred
phone calls a day when I was
doing outbound uh, sales.
It's awful.
And it sucked.
So I, I never forget
that experience.
And I always try to make
someone laugh and, and tell
the, and I always tell.
You have a really nice voice.
You're
very pleasant.
Wow.
That was the fastest
anybody's ever solved a
problem like that for me.
Yeah.
Why not?
Uh, I also get way better
treatment when I do that,
but my point is there's
just a little bit of, of,
of interaction, right?
There's a, I I make someone
laugh and, and I just,
that there's that little
bit of humanity there.
Now, compare that to
when I'm in a chat bot.
And I know damn well there's
nobody on the other side.
Yeah, I know.
I'm fighting an algorithm
to try to get an answer.
If talking to customer
service sucks and it does,
talking to an ai, even if it's
more efficient, which I do
appreciate, feels so lifeless.
It, it
is, uh, quite literally
and isolating.
I'm, I'm basically now
on the phone with myself.
Right.
Which is.
Bizarre.
Yeah.
You're on the phone
with yourself.
Yeah.
You're, you're, you're trying
to solve a problem that might
have even come from isolation
and now you're being more
isolated in order to do it.
Right.
Like, it just feels
absolutely amazing.
And again, like you said,
we're, we're not anti AI at all.
I use it daily.
I think in, in the context
of this conversation, it has
been a massive contributor.
I watched the other day, uh, on,
on one of my LinkedIn posts, a
comment battle between two ais.
They were, they were
absolutely not people.
I watched multiple
comment thread happen
on a, on a post of mine.
I'm like.
None of those are,
those aren't humans.
Those are two people's AI
arguing about my posts.
I'm like, this is
not amazing at all.
And, and in the same way, you
know, the big thing now is if
you see the, the M dash line
used in someone's copy, you
know that it was written by GPT,
which pisses me off because
I was an m Dasher man.
I've always been an m dasher.
I love the dramatic pause,
I love to call it out.
Like I love the
use of the M dash.
And now every time I see M
dash and I, or if I'm thinking
about using one, I'm like.
Nope.
So I'm just gonna start
doing something else.
I don't know what I'm
gonna stick in there, but
I'm gonna start stuffing
something in there.
Um.
So I like that.
So with, with that said,
we get in a situation where
all of a sudden, like with
those comments, we have
to start second guessing
authenticity all the time.
Yeah.
Yeah.
When I looked at, at my LinkedIn
comments, I can always tell
the AI generated ones because
they're always self-referential.
It's, it's always something
like, I make a point in
the AI basically says.
Oh yeah, that point.
That's so true.
Yeah, and I'm like, ah,
okay.
Anyway, thanks for
adding nothing to this
conversation, by the way.
That never adds anything.
It just
reiterates exactly what I said.
Yeah, now I get it.
I get it.
But to your point, within
a year, two years, I.
75 to 80% of my comments are
gonna be AI generated, and
I'm gonna look at it and say,
okay, well that has no value
anymore because, uh, the
authenticity has been removed.
Now it does create a different
opportunity where if you
can, if you can start to,
to deliberately become a.
Authentic and whatever that
looks like, then people will
be more interested in that.
Okay.
So for example, uh, this
is gonna sound crazy.
I think within five years,
getting on the phone with a
customer service rep is gonna be
considered a premium experience.
Yeah, a hundred percent.
I, I genuinely feel like,
like that's gonna make, oh
my god, thank God they have
a human that I can talk to.
Yeah,
there's a human, I think
that all customer service
numbers are gonna be one
900 instead of one 800.
They're gonna be the
highest paid people.
They're gonna, they're gonna
be like, like $300,000 a year.
People that, um, that
actually get on the phone.
But I think the other side of
it is with AI automating so much
of what we can do, it does take
some of the, do I really have to
put much more effort into this?
Or do I really have to be,
you know, more authentic?
Not really.
I think about how much
landing page copy you
and I have written Yes.
In the last 20 plus years.
Okay.
And how we don't really have
to write any of it anymore.
All I have to do is go
into AI and say, here's
roughly what I want to say.
Yep.
And it's gonna give
me a 90% version.
Now, as a guy who writes
for a living, does that make
me feel a bit more useless?
It does, but it also
allows me to not have to
put in that extra effort.
To make it feel more real, to
make it feel more punchy, to
make, you know what I mean?
Yeah.
Like, and, and so I guess what
I'm saying is when we're going
back to, uh, isolation, we
have all these channels that
are getting diluted from us.
All, all the different ways
we're connecting with humans
now we're getting to the point
where even the part where we
would've connected to them,
like digitally, you know,
through, through social media,
whatever, even that's not real.
At least now there's
a human behind it,
right?
My God, the, the last
thing social media needed
was it was a way to become
even less authentic.
Yes.
That's what I'm saying.
Unfortunately, like at,
at some point and, and it
will happen, we're probably
really close to it already,
but all of this efficiency.
Without humanity just becomes
noise at an epic scale.
That's all it becomes.
And then, and then it'll become
about unwinding that, right?
I've decided that in 2026,
I'm just gonna start sending
emails that are only photos
of handwritten letters with a
bloody thumbprint on the bottom.
Right.
Proof of life.
I'm gonna, that's
all I'm sending.
I'm not gonna type anything
anymore because there'll be
a renaissance around that.
And it's gonna be hysterical
to see the ways in which
it comes, but like.
Proof.
Proof of life or proof
of human input is gonna
become a thing, right?
Like, yep, this is me typing
the email that I'm sending you.
Here's a video of me actually
writing it.
Enjoy.
The irony is we're all about to
start paying a massive premium
to go back to the oldie timey
ways things were done and,
and it's going to seem so.
Premium.
Yeah.
Like I said, when when you
get on the phone with your
bank and a person answers,
you're like, whoa, this
feels like concierge style.
And so I think for a lot
of people, you know, we're
seeing just the beginning
of, of, of AI for sure.
But when we start to remove
the human element, the human
layer of so many interactions,
and again, especially among
startups, 'cause we tend to
adopt this stuff first, so,
so again, this is being you
on like our LinkedIn profiles
where we're posting every day
and all of a sudden our common
threads are getting real busy.
It's not with people anymore.
I'm looking at that
going, Hmm hmm.
Before I wanted to post
something because I really
wanted to engage my audience.
Yep.
And I wanted to hear
what they have to say.
Now I kind of know if I post
something, I'm just going
to get a bunch of bots.
I'm gonna spend half my
time second guessing which
one of these are people
and which one aren't.
Right.
And copy pasting some of them
into AI finders to find out.
Uh, there was this community,
I think I told you about it,
uh, on Twitter that was a, a,
a startup community, and it
got started, it started getting
some, some, uh, some good heat
and, you know, there's, there
was some engagement, but as soon
as everyone found out about it,
mind these are all like, like.
Startupy people, they
spammed the hell out of it.
Now there's like, they're
adding like 10,000 users a
month, but not a single one of
them I think is a real human.
Yeah.
And any of them, they are, are
just spam, botting the hell out.
It.
This, this is why we
can't have nice things.
This is just, it's so sad.
Let's say five years ago.
I'm just, you know, using
it as, as a stop point.
That same audience or, or
community would've been much
smaller, but it would've been a
hundred percent human powered.
And I say five years ago,
because I'm just going further
back than ai, just saying like,
you know, more people were,
were less about automation,
more, more about participating.
But even then again, you're,
you're getting the, the, the
best case version of, you know,
what that person had to say
versus who they actually were.
And I think where this is
getting interesting for founders
is think of how many places
Ryan we're trying to turn to,
to vent, to express, to share.
And it's like they're
all shutting down.
Yeah.
Like one door at a time.
It's getting harder
and harder to be real.
Yeah.
Which is interesting.
So again, I I get it.
It, it begs the question then,
so what do we do if loneliness
is now the default setting?
I. Whether we're, whether
we're out and doing things.
I mean, that's the, that's
the craziest part about
it to me, is that even
if you are being social,
you're doing it digitally.
You're not really Right.
Right.
So you're, you're still gonna
be as lonely as ever while
taking action, which starts
to feel really self-defeating.
So how do we, how do we
start to combat this?
Like, what do we do?
Like we have to, we have to
figure out a way to, to connect.
I just lay the
gauntlet down myself.
I, I said, uh, as far as I'm
concerned, the idea of, of
nurturing social networks
and stuff like that is not
my goal at a shutting down
personal level anymore.
Shut down.
Yeah.
I just don't care.
I'm gonna go back to all
personal, like, you know,
direct connections with people.
Crazy sounds, phone calls, and
like I say, text message, which
isn't the most personal thing,
but it's not the same as me
just posting an update on, on a
social network and saying, Hey.
Yeah, giving
a thumbs up on your, on
your, your, your kid post.
Yeah.
The other funny thing is
now when I text people.
It's almost like it's
a handwritten letter by
comparison, and if I call them,
it's like I visited their house.
Right?
It's so
unusual.
You come in bed next
to 'em like, well,
whatcha doing here?
There
we go.
You know what's funny, man?
I, I remember one of the first
times that something, one of
my personal interaction tropes,
the thing that I did for
years and years and years, I
remembered people's birthdays.
This was something that
I did and that people
really respected.
Like I would reach out to
them, Hey, I sometimes I'd even
do it the day before, right?
Like just like, Hey, you
know, I hope you, you got some
fun plans for your birthday.
And people always loved the fact
that I remember their birthdays.
Then everybody's birthday starts
getting plastered everywhere.
Now LinkedIn knows,
Facebook knows all that.
And it took that away from me.
And I remember being really
bitter about that for a
minute and I was like, and
now that I think about it,
how many other things like
that has it taken away?
Right?
You don't have to really
know anybody to look
like you know everybody.
And that's shitty.
I hate it.
It's so funny you
should say that.
'cause I actually had almost
like, kind of like an opposite
reaction coming from a different
direction, uh, years ago.
It's like when, when social
media was just starting, I
was at one of my high school
reunions and I haven't kept
up with many of my classmates
in, in high school just 'cause
they were different states.
But, um, I think maybe
they haven't kept up
with you, but like, I, I
just, I'm guessing there.
Oh yeah, that, that
would also be true.
But I show up and the, the
gal that was checking us in
was like, oh, will, you know,
um, congratulations on your,
your, uh, your daughter summer.
And I was like, wait, what?
Huh?
And I was like, how would you
know that, that I had a kid
much less what her name is?
And now again, this is
gonna sound hilarious.
This is like at the dawn
of social media and it
occurred to me that like
the, that information
is no longer private.
Like, I mean, you could
choose not to share it, but
I'm just saying in general
anymore those things that
to your point, someone would
actually have to know because
you told them and shared
with them are more common.
And now it's still throws me
when I meet with people or
see somebody that I haven't
seen like in 10 years and
they're like, man, uh,
that closet that the master
closet you just finished
for your wife is incredible.
And I'm like, shit, I
haven't seen you in 10 years
and you know what project
I finished this weekend.
Right.
And again, it's not that I have
no idea how social media works,
it's that exactly what you said,
the uniqueness of having to
actually know me and know what
I do and how I spend my time.
'cause you interacted with me,
feels like it's been taken away.
It has.
And I, I think it's, it's one
of the more dangerous pieces.
I think.
I, I look at it this way
and I look at the way
people use technology.
I respect when people
use technology to extend
something they were doing.
Correct.
Yeah.
I do not respect technology when
people use it to jump to the
line, to get to the same place
somebody else did without all
the effort that they put in.
That's annoying to me.
That's annoying to
me every single time.
So here's the thing, I, I
think we're, we're at a point.
With all of this, right?
When we think about isolation
as founders, we're connecting
to humans and, and basically
taking away our isolation
is actually a full-time job.
It's not something that we can
just do in the background where,
oh, you know, I guess I'll
just hang out and eventually
people will come to me and,
and, and I'll, I'll defeat
this thing called isolation.
If you really feel isolated
as a founder, almost all.
All of us do.
Yeah.
If you really wanna build that
circle of trust, that circle of
vulnerability of other founders,
of other people in your life,
you have to go get it now.
In the same way that you
have to go raise capital, you
have to go make a concerted
effort to build the people in
your life, the vulnerability
in your life, the sharing
and connections in your life
that you can't get digitally.
Because if you don't take
a concerted effort toward
getting all of this done,
your isolation is gonna be a
hundred times worse, and that's
the worst possible outcome.
Overthinking your startup
because you're going it alone.
You don't have to, and honestly,
you shouldn't because instead,
you can learn directly from
peers who've been in your shoes.
Connect with bootstrap
founders and the advisors
helping them win in the
startups.com community.
Check out the startups.com
community@www.startups.com
to see if it's for you.
Could be just the
thing you need.
I hope to see you inside.