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.
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.
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.
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.
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.
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.
I just don't believe 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.
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.