June 16, 2025 • 40 mins
Ryan and Will talk about the growing isolation that founders are feeling despite having more ways to connect. They delve into how the shift to remote work, the impact of social media, and the rise of AI have contributed to stripping away the humanity from our daily interactions. They share personal experiences and offer insights into why this sense of loneliness has worsened, and most importantly, explore actionable steps founders can take to reconnect, feel less isolated, and build meaningful relationships in an increasingly digital world.
Resources:
Startup Therapy Podcast
https://www.startups.com/community/startup-therapy
Website
https://www.startups.com/begin
LinkedIn
https://www.linkedin.com/company/startups-co/
Join our Network of Top Founders
Wil Schroter
https://www.linkedin.com/in/wilschroter/
Ryan Rutan
https://www.linkedin.com/in/ryan-rutan/
What to listen for:
01:05 The Paradox of Connection and Loneliness
02:36 Impact of Remote Work on Founders
16:17 The Role of Social Media in Isolation
20:49 The Distorted Reality of Social Media
21:24 The Cynicism Towards Social Media Posts
22:19 Creating Private Spaces and Personal Connections
23:15 Declaring Relationship Bankruptcy
26:53 The Impact of AI on Authenticity
31:08 The Future of Human Interaction in a Digital World
35:33 Combating Isolation as Founders
Mark as Played
Transcript
Episode Transcript
Available transcripts are automatically generated. Complete accuracy is not guaranteed.
(00:00):
Welcome back to the episode ofthe 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'venever been lonelier.
Remote work, social media,performance culture, AI
generated everything, andit seems to be stripping
the, the humanity out ofour, out of our day to day.
(00:22):
You are one of the mostextroverted people I
know you've had massive,uh, uh, parties, founder
dinners, all kinds of stuff.
Like I know I've been toyour house once this year.
Who else has been there?
Ryan, you're thousands of milesaway and I think you've been
there once more time than mostof the people that I know.
(00:42):
We've gone from like, youknow, my wife and I hosting
probably somewhere in theneighborhood of 500 to a
thousand people per year atour house to less than five.
Not, not with a thousand.
You're missing the, youtook 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 mightbe higher than them?
(01:04):
They are taking up more space.
But that, I mean, what's what'sfascinating to me, I. Right
now is that we're at a momentwe're getting connected to other
humans has never been easier.
I mean, like you areconnected almost whether
you wanna be or not at atthe most epic level, right?
We're overconnected if,if we can put it that way.
And yet founders who'vealways had this really
(01:27):
isolating journey.
The nature of, of whatwe do is very isolating.
It's so unique to us and a lotof people don't understand it.
They've never beenmore isolated.
When I talk to founders nowadaysand I, and I say, Hey, and
I always, you know, you andI always check in on them
personally, it's always a bigpart of our discussions and they
say, you know, where are you at?
Who are you talking to?
More and more, I'm hearingpeople say, I'm really alone.
(01:49):
And I'm like, whatthe hell happened?
I think it's important for, forall of us and the, the folks
listening and, and Ryan, youand I in this, uh, episode, to
unpack why this is happening.
Also point out whyit's getting worse.
Yeah, yeah.
Right.
Like the horizondon't look good.
More importantly, what we canstart to do about it so we
can become less detached, moreconnected to other people and
(02:11):
feel less isolated as a founder.
Yeah, man.
It's interesting 'cause we've,we've done an episode before
on like the, the isolationthat comes with being a
founder just from being atthe top of something where
you, you don't have peerswithin 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'sgotten and some of the
causal things behind that.
(02:32):
So what do you, whatdo you think is the,
the, the first driver?
What's the, what'sthe big one for you?
I think we gotta
start with work from home.
Like, I, I mean, becauseit was global, it happened
to everybody all at once.
So it wasn't like a, a specificphenomenon in particular
within the startup community.
It fundamentally changedthe office place.
You know, uh, I had a foundercall me, this is so timely,
(02:53):
like an hour ago, and, andwe're talking on the phone.
Good friend of mine, a, aguy that, you know, he raised
a bunch of money and hejust, 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'sreally low per square foot.
Right?
Like, like for anywheremuch less San Francisco.
We were the buyer.
We were the, yeah, exactly.
Exactly.
And, and then he, hementioned without realizing
(03:15):
the significance of it, andhe is like, yeah, and so we
signed our two year lease.
I was like, wait, what?
Huh?
Uh, you signed a two yearlease 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 backjust four years, you'd be
lucky to get a 10 year lease.
10 year.
Yeah.
Yeah.
Nobody's pushinga two year lease.
(03:35):
Massive lease.
If you could
find office space at all.
Oh, I'm sorry sir. WeWorkis down the street.
Right?
That's what they would tellyou with a two year lease.
Exactly.
Didn't, that'd evenmore expensive.
The reason I say this isbecause clearly startups
have abandoned their offices.
En mass in order for that dealto even be, and he said that
office was sitting in a, in apretty prime spot for two years.
I mean, there crazy.
(03:56):
There was even just a fewyears 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 itpoints to is just the impact
that COVID and then the workfrom home culture has had in
how widespread it is now, Ryan,we were way ahead of this.
(04:17):
Uh, we, we started workfrom home 15 years.
I mean, 10, 15 years ago.
I mean, like sincethe beginning.
Yeah.
I would say like there,there's been at least some
work from home components.
Going back at least 12years, maybe 13 now.
And, and I say that 'causeI wanna talk about what the
cultural and kind of personaltransition became as we
went from partial work fromhome to completely remote.
(04:40):
Yeah.
So partial work from home,just for, for folks listening,
the partial work from homewas early on we decided that
on Wednesdays we would creatework from home Wednesdays.
Yep.
And if I timestampedthat, that's like 2012.
That's a very long time ago.
Yeah.
It was 12 or 13 and it was.
It was just intendedto be, well, we tried
it for the summer.
Remember?
It was like a, itwas a summer break.
Let's see.
Let's see what happens.
Let's give, let's give theteam a, a chance to try this.
(05:02):
And everybody loved it,obviously, because, uh, it,
it helped break things up.
You know, you only had togo to drive to work two
days in a row, ever in.
With that though, we are stilla, an office, um, based culture
and I wanna talk about whatcame with that, that we've
lost and just everybody's lost.
Right.
What came with that was forme, and I'm interested for
you, was just forcing meto get up in the morning
(05:23):
and shower and go somewherelike, and be presentable as
a human being to other humanbeings like that alone was,
was an important part of me.
Like, I'm a motivatedguy, so it's not like I'm
sitting in bed otherwise.
But like, just knowing thatI had to go present myself
to other humans, especiallyas a manager, mattered.
Like, like itchanged my outlook.
(05:45):
I didn't feel alonebecause I was knowing, I,
I knew I was going intoa room of other people.
Now when I get up and Idon't shower and I'm in my
sweatpants and I'm not gonnasee another human being in
person, you know that myfamily for an entire day.
That's way different.
That does get lonely.
Yeah, it does.
Yeah.
It starts to, you start tobecome quite isolated because
of things like that, andit's easy to fall into that,
(06:05):
and then just that becomesthe, the absolute norm.
I think that was right.
The big thing for me wasthat like a day or two here
or there, like that didn'thave any impact on me.
Zero.
Mm-hmm.
Right.
Like, okay, cool.
I'm not, I'm not gonna getdressed 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 thoseroutines with other routines.
(06:25):
Right.
So other things cameand fell into those
places, took some time.
But things likemeditation or breath
work, practice, uh mm-hmm.
Things like getting up andmaking lunches for my kids
in the morning, which Iclearly don't need to do.
My, my, my wife and I.Either one of us can do that.
Uh, at this point thekids are old enough, they
can do that themselves.
I like doing it and Ithink part of it is.
That sense of ritual in themorning and like this is the
(06:47):
beginning of productivity.
I'm creating something,it's gonna be beneficial
to somebody else.
And so I think in my case, it'sjust been a matter of replacing
those, but pretty arbitrarily.
Mm-hmm.
I think as those things wentaway, something else had to
come in and take its place.
Um, and at some point itkinda didn't even really
matter what it was.
They just, right.
I gravitate, food is oneof my love languages.
Right.
(07:07):
I like to feed people.
Yeah.
And so for me it waspretty obvious, like,
let's just go make food.
Let's make a great
breakfast, great lunch.
That works.
You know what's interestingthough, again, kind of mapping
back to founders specifically,you know, when you and I would
go in the office and we'd bewith other coworkers, leadership
team members, et cetera.
Yeah, yeah.
You know, we'd sit ina conference room from
time to time, we'd likego to lunch every day.
Like we had a lot ofinteraction where like
(07:29):
just daily frustrationscould 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 thinkjust the little social cues
that I had come to rely on.
Right.
Like, like even thingslike noticing that
someone's having a bad day.
Yeah.
Just their body language.
(07:50):
Just kind of, you know, how, howthey're responding, et cetera.
And being able to like leanin on that a little bit.
I always send a frowny facein 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, likenow I have no idea how
people are doing now.
This isn't to say like,Hey, why can't you ask them?
(08:11):
It's because there's adifferent level of decorum.
Well, there's also adifference between observing
something and having to ask.
Right?
If I have to ask howyou're feeling, that
leaves it up to you.
But when, when there's nochance for interpretation
or there's the chance forinterpretation rather, and
I can just sort of see likeyour body postures different.
Your body language is different.
Your energy feels off.
Uh, you didn't brush yourhair and you came to the
office anyways, like,what's going on bud?
You okay?
(08:32):
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 thosehealth issues and like I was
on so much medication thatI, I actually, I couldn't
sit up anymore and I'd haveto, like, we spent a lot of
time time in the conference
room.
Exactly.
Like I remember we'dhave these meetings.
Ellie and, and I talked atone point about mounting
a whiteboard on theceiling above the couch.
Nobody could lay down the starelike a planetarium slip up guys.
(08:54):
Yeah.
But like, I mean, I, I wason so much pain medication
'cause I was in so much painthat I couldn't function.
Imagine you guys never saw that.
Okay.
Like never saw me in that state.
And we're just wonderingwhy, like, I, I couldn't
respond on Slack or anythingor anything or on Zoom or.
You know, whatever our, ourtools are, I wanna map that
back to my feelings of, youknow, uh, how that makes me
(09:15):
feel as a founder as being, youknow, uh, isolated, et cetera.
When in that case, itwas a health issue,
which I would argue thatnearly every founder has.
But in that case, it was ahealth issue when no one can
even be around you to noticethat you're in pain, right?
Whatever form that takesand respond as a human,
that's isolating as hell.
It is.
Just the, the, by virtue ofbeing seen, because then you
(09:36):
know that people can observe it.
You can do, and, and we dothese things consciously
or subconsciously.
We send little cues that like,I need to be seen right now.
I need you to understandthat I'm going through this.
I need you to seethat I'm happy.
I need you to see, like, great.
You come into your oldbubbly, you're like, well,
you've got something youwanna tell the world, right?
Something good happen thatyou want to share, right?
Conversely, when the other,when there's something that you
don't feel comfortable sharing.
You want to have itdrawn out of you.
(09:56):
That needs to be observed toowhen you're on your own by
yourself and nobody can do that.
When you can't be seen.
It creates this additionalburden 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.
(10:17):
Yeah.
When it becomes everyday, everybody's in
that same situation.
So there isn't this otheropportunity like, well,
because you observed themdoing that, now here's my
chance to share my piece of it.
It doesn't worklike that anymore.
There's, there's another sideof it too, which is when you're
in front of people and youdo or say something that they
appreciate, you get a bit ofa, a, a, a visual, emotional,
(10:37):
social cue that tells you,you did something right.
Like some, one of the thingsI, 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 somebodyor tell them that they did
a good job with something.
'cause I knew it wasimportant to them.
And I do that now in Slack,but it, it lands so empty it
does not hear the same at all.
(10:57):
Not at all.
At all.
Um, and, and, and here's whatI think about it goes the
other way too, when someonewould say, Hey, you know, I
really appreciate you helpedme 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 knowthat I'm doing a good job.
Yeah.
My default assumption has alwaysbeen in my 31 years is that
everyone hates me and they justtolerate me because of that.
(11:21):
Having no cues to tellme otherwise is painful.
Yeah.
Now I'm used to it, butif I were three years in
my career as a founder.
And I had no way to get asocial signal from humans,
my, my fellow humans.
Yep.
That they're reallyhappy with me.
Right.
Without, like, surveying them.
(11:41):
I think that would be veryisolating after a while.
It is.
I I, this was a, a conversationthat came up a couple weeks
ago in, in one of the foundersgroups, and it was this
notion that somebody broughtup 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 broughtup this aspect of it was like
yes and no, because there's,there's so much noise,
(12:02):
there's so much isolation.
Yes.
The technical side of things,the product build side of
things, um, the content creationside of things, yeah, you've
got some tools now that makethat a lot easier, but I would
argue that especially for earlyfounders, young founders, first
time founders, the human aspectof it has gotten so much harder.
The idea that we wouldhave a meeting where not
(12:23):
everybody was sitting inthe 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 toolsnow and you know, you, you
said Slack, but I, I wannacall it even like Zoom,
where we can see each other.
We're using it right now torecord this podcast, but it
still hits different, right.
I, you still don'tget the same cues.
And I, I think back, I'm like.
(12:45):
Okay.
I'm not gonna say I have nofond memories from a Zoom call.
Some stuff has happened onZoom calls that were great.
I have a thousand fond memoriesfrom like crappy interactions
in our office kitchen rightover bad coffee, right?
Yep.
Because I. We were there, wewere present, we were social,
we were, we were together.
We could read the cues.
You know, it's funny you shouldsay, I, I've always had this
thing where I think about howmuch time I spend in a digital
(13:06):
world, and I've been a digitalnative since the eighties.
So like, I've been atthis for a long time.
Yeah.
And, and I've played countlesshours of video games.
And I, and I, and I thinkabout how many of those video
games do I have a lasting,like highlight, like life
highlight reel from Yeah.
And, and what's funny isevery single one that I could
come up with where I triedto remember like a meaningful
(13:27):
moment, a memory where I,where I played a video game,
nearly every single one ofthose memories had to do with
the person sitting next to me.
Yep.
When I was playingit like I like.
You probably remember thetime that you finally figured
out how to beat King Hippoand Mike Tyson's punch out.
Right.
And I remember Jay Faanlike had just unlocked it
'cause he'd figured it out inNintendo Power Magazine and
(13:47):
like that was a big moment.
Yeah.
Yeah.
That's, I can't tell you anyNintendo power like I got, but
it, but it was more about twoof us in a sleepover having
like this, you know, this.
Fun time.
Same with Zoom, same withdigital media as a whole.
Think of how many memoriesyou don't have by scrolling
through social media.
I mean, that one time where Iwas, I was scrolling through
social media and had thebest time of my life, right?
(14:09):
Like happens.
Never.
No, you're just, you'repouring dopamine in there.
But to know no end, I thinkit's, it's interesting.
I think that.
Again, you and I have beenin the part of the digital
world since the digitalworld became a world.
Right?
And so originally the digitalpiece was a conduit to
experiences, mostly with otherpeople, to your point, right?
Like it was the memory offinally making it past that
(14:31):
level in Sylvania, or, you know,trying our hardest to, to make
it further than the first levelin contra with only three lives.
And then all of a suddenthe digital piece became the
experience as opposed to beinga conduit to the experience.
And I think that was whereit really started to change
and become something thatwas less, less palpable,
less social, less.
Less everything.
Let's isolate that.
Let's, let's say, yeah.
(14:51):
The, the isolation quiteliterally of us from other
humans on a daily basishas really locked in this
sense of not just physicalisolation, but mental isolation.
Yeah.
Which is keeping us from havinga lot of the little interactions
that actually did keep us going.
Now you're gonna hear somefolks, uh, say rightfully so.
(15:12):
It actually worked out greatfor me because I'm an introvert.
I hate being around otherpeople and that did nothing
but create anxiety for me.
Awesome.
I, I'm, I'm, I'mglad that's a fix.
But I'm saying for a lot ofpeople, whether they realize
it or not, particularly peoplewho've never had an in-office
experience, it's not the officethat, that they're missing.
It's the interaction withhumans forced or otherwise.
The office itself usually
(15:32):
sucks.
Yeah.
The science is there,productivity's higher.
Lots of, lots of good thingshappen with, with remote work.
I think there's a coupleof flaws in all of this,
which one of them beingthis 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 doingthe remote thing for, for longer
than most, and even there, it'sstill, you know, we're still the
(15:53):
first generation at, at at, atbest, and most people have been
doing this since the pandemic.
So we're a couple years in.
So I think there wereproductivity and there was all
these things that did happen.
But I feel like the socialdegradation piece of it,
the, the isolation piece issomething that builds over time.
I don't think we'refully recognized exactly
what the downsides are.
I agree.
I agree.
So, uh, let's move onbecause I, I think that
(16:13):
one is very obvious.
I mean, it's very visual,it's very visceral.
The other that certainly camebefore it that I think has
sadly done far more harm thangood would be social media.
And, and, and the idea.
Of replacing our interpersonalconnections with a digital one.
Yeah.
I thought you were gonnasay motor cars, but Yes.
(16:33):
Social, socialnetworks probably.
Now, here's the thing, I'mnot anti-social media, but I,
I think we, we've definitelycome to a milestone point with
social media and I think it's,it's becoming well recognized.
It's really messed usup in a lot of ways.
And I think one of thebiggest ways, it gave us the
illusion of connection withoutactually having connection.
(16:54):
Yeah.
It gave me the illusionthat such a super level, I'm
connected to lots of people.
Right, right.
I had an in-person relationshipthat was meaningful and it
was, you know, and, and, andthere were memories attached
to it, and it got extended.
By virtue of, of socialmedia, 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.
(17:15):
Yeah.
I think the idea that, thatwe increased the frequency
with which people could sortof tap into our lives and see
the stuff that was happeninggot traded for, for the depth.
Right.
We took, we, we tradedsuperficial frequency
for, for true depth.
I remember it was probablythe third or fourth time.
I had asked this question, heardsome version of the same answer.
It was like, oh man, whenwas the last time we talked?
(17:37):
Right.
They just all of a suddenlike realizing it had
been a long time sinceI talked to this person.
They're like, oh yeah, butI keep, I keep tabs on you
with, uh, via Facebook.
And like the first time I heardit 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 nottalking 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.
(17:57):
And that's, that's enough,except that it's not right.
It's absolutely not.
Let me dig into that a littlebit more because we're trading
different types of interactions.
Yeah.
Dramatically.
And it has a, a strong presenceto it and not a good one.
For example, back in the day.
You know, when we were hostingall these events, we had
thousands of people at, at ourhouse, most of 'em founders.
We'd spend time at cocktailparties and you, you'd hear
(18:19):
the, the emotion and theexcitement and the terror
of other founders and whatthey were going through.
And you know, one of thethings we did for decades is
we'd get a bunch of foundersin a room and we'd just.
Talk shop.
Everybody would just talkabout what they were working
on and what their concernswere, and they were the amazing
conversations, wildly connected,built friendships overnight.
Like it was incredible, butevery had everything to do with
(18:41):
being in front of other people.
When we tried to replicatethat, which we did, I mean,
we specifically tried toreplicate that like same idea
with doing it all digitally.
We struggled because all ofa sudden the, the lack of
presence made it more difficult.
The communication channelwas there, but there
was something missing.
I
think part of it became thatlike vulnerability went away.
(19:01):
I think it's a lot easier tobe vulnerable in, in person
when you can see the reactionto it and you can control
how many people see it theminute you post it on a
social, social media, right?
It's, there's no control, right?
I'm vulnerable now to anyonewho happens to come across
this, and so everybody juststarted posting the positives.
And so good news guys, there'snothing bad happening to
founders anymore at all.
We don't have to havedinners and talk about it.
(19:22):
The downside, 'causeeverybody's just kicking
ass and taking names.
Fantastic, right?
That's what it feltlike for a while.
It was like just everybody'sInstagram version of
their startup man wasthat bad for everybody?
I.
You know something that'sreally funny about everything
we talk about here isthat none of it is new.
Everything you're dealingwith right now has been done a
thousand times before you, whichmeans the answer already exists.
(19:45):
You may just not knowit, but that's okay.
That's kind of whatwe're here to do.
We talk about this stuff onthe show, but we actually
solve these problems alldayLong@groups.startups.com.
So if.
Any of this sounds familiar.
Stop guessing about what to do.
Let us just give you the answersto the test and be done with it.
The performative part hasgotten geometrically worse
(20:07):
with time and, and becauseit compounds on itself.
Well, if everyone else, allmy other friends are saying
that, that, that they're havingthe best vacations and best
spouses and best whateverin their life, then I guess.
I have to, and when Iget a chance to respond,
I'm gonna make mine asover the top as possible.
I need the best possible photo,I need the best possible filter.
Yep.
I need the cutest possiblecaption, you name it.
(20:28):
Right.
And all of these thingsare performative, right?
I'm, I'm doing it becauseI have to perform now
to, to an audience.
You leave that spotlight on24 7 and you keep perpetuating
that, that doesn't lead toa positive place because.
Newsflash, if you're a founder,you are not happy all the time.
You're depressed as fuck, right?
(20:49):
And I think, uh, part of thechallenge is we've now got
this distorted reality aroundus where it's compounded.
Every person that I'm seeingin my feed is doing amazing.
And so immediately if I gothrough my feed, actually,
uh, I hardly ever usesocial media, truth be told.
And sadly, I don't wannacall myself selfish.
I'm just doing other stuff.
(21:10):
I never look atother people's stuff.
I have no idea what my friendsand family are doing, like
on social media, media, atleast the Facebook version
over the Instagramversion 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 careabout those people.
I don't care aboutfollowing all those updates.
Yeah.
And so anyway, when I do go onthere and the rare times where
I'm actually scrolling throughmy feed for something and I see
what everybody else is doing.
(21:31):
My first thought, becauseI'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 photoof you and your family.
Like, dude, I talkedto 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 niceautumn scene where all of you
are, are in an orchard somewhereand uh, is a healthy pumpkin.
(21:52):
Look at that.
Yeah, with a very healthypumpkin, 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 thatand you're like, oh my God, my
life must suck by comparisonbecause yeah, the contrast
becomes really dangerous,but you know, it's bullshit.
Yeah.
But you can't ignoreit either, right?
(22:12):
Like this is whatseems to happen.
Like we, we, we do know, andyet 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 homething, I'm not sure there's
that much you can change there.
I think there are some thingsyou can change within social,
uh, social media, but maybeeven more so like, how do
we start to carve out somesome safe private spaces.
(22:33):
Uh, you know, is it, isit going back to doing
the small dinners thing?
You know, where do we getthe unfiltered talk again?
How do we do this?
I'm going throughthis as we speak.
Uh, right now, uh, I'm goingthrough all the people that
I wanna stay in touch with.
I'm basically just creatinga giant list of people that
I'm gonna text and call likea catalog of like faces,
like a, a book of fa likea Facebook facing book.
(22:57):
Yes.
But, but instead of likegoing through feeds and
everything else like that.
Yeah.
I'm gonna make aconcerted effort now.
Now here's the, the,the key word there.
Effort to make sure thatall the people that I care
about, that I'm activelyreaching out to them.
And typically when I reachout to somebody, we end up
following by grabbing a lunch ora dinner or something like that.
Yeah.
It has occurred to me.
I, I'm declaringrelationship bankruptcy.
(23:17):
I. Which is to say I nolonger believe that I can
develop or sustain any ofmy relationships digitally.
Yeah.
Yeah.
I just don't believeIt doesn't work.
It doesn't work.
I can send messages.
I can create updates.
I can follow updates.
I don't actually thinkthat I'm gonna build
a better relationshipwith anyone in my life.
Digitally?
(23:38):
No, I think it goes back towhat I was saying before,
which is that digital usedto be the conduit, right?
So we would, we wouldmessage somebody and say,
Hey, let's go grab dinner.
Right now, it's just, Hey, I sawthat dinner you had last night.
Those appetizers lookgreat on Instagram, right?
I think over time it's justtaken such a different form that
it's not, it's really keepingus from taking that next step
(23:58):
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'sbeen, 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 hotbedof startup activity.
Right.
I have good friends.
I've, I've, I've built greatnetworks here and we do a lot
of interesting things together.
(24:19):
And I do have some otherfounders around, but it
is not the same thing.
It is absolutelynot the same thing.
And so as we're, as we arestaring, you know, we're
as, as of this recording 23.
Days away fromheading to Madrid.
Um, I've already startedsetting up founder Coffees,
lunches, uh, some people withinthe startups.com network.
Some people without, I'msuper excited about it, right?
So I think this is me.
I also like, I. Not only didI have to de declare, uh,
(24:41):
relationship bankruptcy, and Ihad to, to restructure in a way
required actually physicallymoving myself somewhere
where it's more possible.
Yeah.
I gotta tell you, every timeI make a concerted effort,
like I, I, I get on the phonewith a, with a friend or you
know, I meet somebody out orwhatever, that fills up my
bank account of contentmentof I guess being seen.
(25:02):
If, if you wanna say,that's the thing.
So much more.
In fact, it gets.
Zero filling when, when I'mtrading a DM with someone.
Yep.
Right.
Like I kind of look at allof those things like dms, et
cetera, like the equivalentof, 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, itshould just be the preamble,
(25:23):
right?
This is just the Yeah, yeah.
Yeah.
Again, I understand it worksdifferently for everybody,
like, you know, we're comingfrom a bit of a different
generation where that was, uh,we, we can see the contrast.
Maybe a little bit differently.
Whereas someone growing upwith all these tools right now,
and it's all, they know, theirlevel of what a relationship
means is gonna be dramaticallydifferent because their level
(25:43):
of relationship might mean wedo talk every day on dm and
that is how, that's how allmy relationships are built.
So why would that beany better or worse?
Which I'm, I'd be really curiousto dig into that at some point.
Uh, but we'd need somepeople on here who are kind
of native to that epoch tobe able to say that like.
Yes.
And those do fulfill me.
Like is it, is it the contrast?
Is it the delta from what weknew to what we have that's
(26:04):
bothering you and I or are theygonna experience the same sort
of superficiality and, and samechallenges that that we have.
I think that in person, notwith everybody, obviously,
but I think in person youget a level of vulnerability
and authenticity that isyes, really difficult.
To replicate outside ofthat, not impossible.
Yeah.
Again, and, and differentpeople have different
(26:25):
ways of communicating.
I could see somebody elsecoming on and saying, you know
what, I see the polar opposite.
I'm really nervous whenI'm around other humans.
I can't express myself.
But when I go to a, a forumwhere I can be anonymous,
read Reddit and say exactlywhat's on my mind or, you know,
share, I feel so much better.
And that fills me up, youknow, in, in, in my way.
I could get that.
Yeah.
Uh, I get that.
Just how I feel.
(26:46):
Yeah.
It hasn't workedthat way for me.
Uh, you, you saidtwo, two words.
One, one of 'em we had talkedabout a bit earlier, which
is vulnerability and theother one was authenticity.
Man, for as much as I amenjoying 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 strippedaway so much of the
(27:07):
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 vaporizedmy personality outta
this piece entirely.
Yep.
Made some goodgrammatical corrections,
but my God, I'm gone.
I'm gone.
This is gonna take the othertwo categories we talked
about, about, you know, workfrom 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.
(27:29):
We are huge fans of ai.
Right, so, so this isn'tone of those cases where
like, we're about to goon some anti AI ramp.
This is, no, AI is awesome, butwe 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 probablygonna happen too.
It's something that, what reallyconcerns me is that we are now
(27:50):
taking away tons and tons andtons of human interactions.
And we're not replacingthem 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 customerservice rep, and I, I always
do a thing with customerservice reps where I always
try to make them laugh.
Yep.
I know that sounds odd,but I picture those
(28:12):
people hating their jobs.
I remember when I usedto have to make a hundred
phone calls a day when I wasdoing outbound uh, sales.
It's awful.
And it sucked.
So I, I never forgetthat experience.
And I always try to makesomeone laugh and, and tell
the, and I always tell.
You have a really nice voice.
You're
very pleasant.
Wow.
That was the fastestanybody's ever solved a
problem like that for me.
Yeah.
Why not?
Uh, I also get way bettertreatment when I do that,
(28:33):
but my point is there'sjust a little bit of, of,
of interaction, right?
There's a, I I make someonelaugh and, and I just,
that there's that littlebit of humanity there.
Now, compare that towhen I'm in a chat bot.
And I know damn well there'snobody on the other side.
Yeah, I know.
I'm fighting an algorithmto try to get an answer.
If talking to customerservice sucks and it does,
talking to an ai, even if it'smore efficient, which I do
(28:54):
appreciate, feels so lifeless.
It, it
is, uh, quite literallyand isolating.
I'm, I'm basically nowon the phone with myself.
Right.
Which is.
Bizarre.
Yeah.
You're on the phonewith yourself.
Yeah.
You're, you're, you're tryingto solve a problem that might
have even come from isolationand now you're being more
isolated in order to do it.
Right.
Like, it just feelsabsolutely amazing.
(29:14):
And again, like you said,we're, we're not anti AI at all.
I use it daily.
I think in, in the contextof 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 wereabsolutely not people.
I watched multiplecomment thread happen
on a, on a post of mine.
(29:35):
I'm like.
None of those are,those aren't humans.
Those are two people's AIarguing about my posts.
I'm like, this isnot amazing at all.
And, and in the same way, youknow, the big thing now is if
you see the, the M dash lineused in someone's copy, you
know that it was written by GPT,
which pisses me off becauseI was an m Dasher man.
I've always been an m dasher.
I love the dramatic pause,I love to call it out.
(29:56):
Like I love theuse of the M dash.
And now every time I see Mdash and I, or if I'm thinking
about using one, I'm like.
Nope.
So I'm just gonna startdoing something else.
I don't know what I'mgonna stick in there, but
I'm gonna start stuffingsomething in there.
Um.
So I like that.
So with, with that said,we get in a situation where
all of a sudden, like withthose comments, we have
to start second guessingauthenticity all the time.
(30:18):
Yeah.
Yeah.
When I looked at, at my LinkedIncomments, I can always tell
the AI generated ones becausethey're always self-referential.
It's, it's always somethinglike, 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 foradding nothing to this
conversation, by the way.
That never adds anything.
It just
reiterates exactly what I said.
(30:39):
Yeah, now I get it.
I get it.
But to your point, withina year, two years, I.
75 to 80% of my comments aregonna be AI generated, and
I'm gonna look at it and say,okay, well that has no value
anymore because, uh, theauthenticity has been removed.
Now it does create a differentopportunity where if you
can, if you can start to,to deliberately become a.
(31:00):
Authentic and whatever thatlooks like, then people will
be more interested in that.
Okay.
So for example, uh, thisis gonna sound crazy.
I think within five years,getting on the phone with a
customer service rep is gonna beconsidered a premium experience.
Yeah, a hundred percent.
I, I genuinely feel like,like that's gonna make, oh
my god, thank God they havea human that I can talk to.
(31:21):
Yeah,
there's a human, I thinkthat all customer service
numbers are gonna be one900 instead of one 800.
They're gonna be thehighest paid people.
They're gonna, they're gonnabe like, like $300,000 a year.
People that, um, thatactually get on the phone.
But I think the other side ofit is with AI automating so much
of what we can do, it does takesome of the, do I really have to
(31:43):
put much more effort into this?
Or do I really have to be,you know, more authentic?
Not really.
I think about how muchlanding page copy you
and I have written Yes.
In the last 20 plus years.
Okay.
And how we don't really haveto write any of it anymore.
All I have to do is gointo AI and say, here's
roughly what I want to say.
Yep.
And it's gonna giveme a 90% version.
(32:03):
Now, as a guy who writesfor a living, does that make
me feel a bit more useless?
It does, but it alsoallows me to not have to
put in that extra effort.
To make it feel more real, tomake it feel more punchy, to
make, you know what I mean?
Yeah.
Like, and, and so I guess whatI'm saying is when we're going
back to, uh, isolation, wehave all these channels that
are getting diluted from us.
(32:24):
All, all the different wayswe're connecting with humans
now we're getting to the pointwhere 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'sa human behind it,
right?
My God, the, the lastthing social media needed
was it was a way to becomeeven less authentic.
Yes.
That's what I'm saying.
Unfortunately, like at,at some point and, and it
(32:45):
will happen, we're probablyreally close to it already,
but all of this efficiency.
Without humanity just becomesnoise at an epic scale.
That's all it becomes.
And then, and then it'll becomeabout unwinding that, right?
I've decided that in 2026,I'm just gonna start sending
emails that are only photosof handwritten letters with a
bloody thumbprint on the bottom.
(33:05):
Right.
Proof of life.
I'm gonna, that'sall I'm sending.
I'm not gonna type anythinganymore because there'll be
a renaissance around that.
And it's gonna be hystericalto see the ways in which
it comes, but like.
Proof.
Proof of life or proofof human input is gonna
become a thing, right?
Like, yep, this is me typingthe email that I'm sending you.
Here's a video of me actually
writing it.
Enjoy.
The irony is we're all about tostart paying a massive premium
(33:26):
to go back to the oldie timeyways things were done and,
and it's going to seem so.
Premium.
Yeah.
Like I said, when when youget 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 lotof people, you know, we're
seeing just the beginningof, of, of AI for sure.
But when we start to removethe human element, the human
(33:47):
layer of so many interactions,and again, especially among
startups, 'cause we tend toadopt this stuff first, so,
so again, this is being youon like our LinkedIn profiles
where we're posting every dayand all of a sudden our common
threads are getting real busy.
It's not with people anymore.
I'm looking at thatgoing, Hmm hmm.
Before I wanted to postsomething because I really
wanted to engage my audience.
Yep.
And I wanted to hearwhat they have to say.
(34:09):
Now I kind of know if I postsomething, I'm just going
to get a bunch of bots.
I'm gonna spend half mytime second guessing which
one of these are peopleand which one aren't.
Right.
And copy pasting some of theminto 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 gettingsome, some, uh, some good heat
and, you know, there's, therewas some engagement, but as soon
(34:30):
as everyone found out about it,mind these are all like, like.
Startupy people, theyspammed the hell out of it.
Now there's like, they'readding like 10,000 users a
month, but not a single one ofthem I think is a real human.
Yeah.
And any of them, they are, arejust 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.
(34:51):
I'm just, you know, usingit as, as a stop point.
That same audience or, orcommunity would've been much
smaller, but it would've been ahundred 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
(35:14):
versus who they actually were.
And I think where this isgetting interesting for founders
is think of how many placesRyan we're trying to turn to,
to vent, to express, to share.
And it's like they'reall shutting down.
Yeah.
Like one door at a time.
It's getting harderand 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
(35:36):
is now the default setting?
I. Whether we're, whetherwe're out and doing things.
I mean, that's the, that'sthe craziest part about
it to me, is that evenif you are being social,
you're doing it digitally.
You're not really Right.
Right.
So you're, you're still gonnabe as lonely as ever while
taking action, which startsto feel really self-defeating.
So how do we, how do westart to combat this?
Like, what do we do?
Like we have to, we have to
figure out a way to, to connect.
(35:57):
I just lay thegauntlet down myself.
I, I said, uh, as far as I'mconcerned, the idea of, of
nurturing social networksand stuff like that is not
my goal at a shutting downpersonal level anymore.
Shut down.
Yeah.
I just don't care.
I'm gonna go back to allpersonal, like, you know,
direct connections with people.
Crazy sounds, phone calls, andlike I say, text message, which
isn't the most personal thing,but it's not the same as me
(36:17):
just posting an update on, on asocial network and saying, Hey.
Yeah, giving
a thumbs up on your, onyour, your, your kid post.
Yeah.
The other funny thing isnow when I text people.
It's almost like it'sa 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 nextto 'em like, well,
whatcha doing here?
There
we go.
You know what's funny, man?
(36:38):
I, I remember one of the firsttimes that something, one of
my personal interaction tropes,the thing that I did for
years and years and years, Iremembered people's birthdays.
This was something thatI did and that people
really respected.
Like I would reach out tothem, Hey, I sometimes I'd even
do it the day before, right?
Like just like, Hey, youknow, I hope you, you got some
(36:59):
fun plans for your birthday.
And people always loved the factthat I remember their birthdays.
Then everybody's birthday startsgetting plastered everywhere.
Now LinkedIn knows,Facebook knows all that.
And it took that away from me.
And I remember being reallybitter about that for a
minute and I was like, andnow that I think about it,
how many other things likethat has it taken away?
Right?
You don't have to reallyknow anybody to look
like you know everybody.
(37:20):
And that's shitty.
I hate it.
It's so funny youshould say that.
'cause I actually had almostlike, kind of like an opposite
reaction coming from a differentdirection, uh, years ago.
It's like when, when socialmedia was just starting, I
was at one of my high schoolreunions and I haven't kept
up with many of my classmatesin, in high school just 'cause
they were different states.
But, um, I think maybe
they haven't kept upwith you, but like, I, I
just, I'm guessing there.
(37:41):
Oh yeah, that, thatwould also be true.
But I show up and the, thegal 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 youknow that, that I had a kid
much less what her name is?
And now again, this isgonna sound hilarious.
This is like at the dawnof social media and it
occurred to me that likethe, that information
(38:04):
is no longer private.
Like, I mean, you couldchoose not to share it, but
I'm just saying in generalanymore those things that
to your point, someone wouldactually have to know because
you told them and sharedwith them are more common.
And now it's still throws mewhen I meet with people or
see somebody that I haven'tseen like in 10 years and
they're like, man, uh,that closet that the master
closet you just finishedfor your wife is incredible.
(38:25):
And I'm like, shit, Ihaven't seen you in 10 years
and you know what projectI finished this weekend.
Right.
And again, it's not that I haveno idea how social media works,
it's that exactly what you said,the uniqueness of having to
actually know me and know whatI 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 oneof the more dangerous pieces.
(38:45):
I think.
I, I look at it this wayand I look at the way
people use technology.
I respect when peopleuse technology to extend
something they were doing.
Correct.
Yeah.
I do not respect technology whenpeople use it to jump to the
line, to get to the same placesomebody else did without all
the effort that they put in.
That's annoying to me.
That's annoying tome every single time.
So here's the thing, I, Ithink we're, we're at a point.
(39:07):
With all of this, right?
When we think about isolationas founders, we're connecting
to humans and, and basicallytaking away our isolation
is actually a full-time job.
It's not something that we canjust do in the background where,
oh, you know, I guess I'lljust 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 isolatedas a founder, almost all.
(39:28):
All of us do.
Yeah.
If you really wanna build thatcircle 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 youhave to go raise capital, you
have to go make a concertedeffort to build the people in
your life, the vulnerabilityin your life, the sharing
and connections in your lifethat you can't get digitally.
Because if you don't takea concerted effort toward
(39:51):
getting all of this done,your isolation is gonna be a
hundred times worse, and that'sthe worst possible outcome.
Overthinking your startupbecause you're going it alone.
You don't have to, and honestly,you shouldn't because instead,
you can learn directly frompeers who've been in your shoes.
Connect with bootstrapfounders and the advisors
helping them win in thestartups.com community.
(40:12):
Check out the startups.comcommunity@www.startups.com
to see if it's for you.
Could be just thething you need.
I hope to see you inside.
Welcome back to the episode ofthe 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'venever been lonelier.
Remote work, social media,performance culture, AI
generated everything, andit seems to be stripping
the, the humanity out ofour, out of our day to day.
(00:22):
You are one of the mostextroverted people I
know you've had massive,uh, uh, parties, founder
dinners, all kinds of stuff.
Like I know I've been toyour house once this year.
Who else has been there?
Ryan, you're thousands of milesaway and I think you've been
there once more time than mostof the people that I know.
(00:42):
We've gone from like, youknow, my wife and I hosting
probably somewhere in theneighborhood of 500 to a
thousand people per year atour house to less than five.
Not, not with a thousand.
You're missing the, youtook 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 mightbe higher than them?
(01:04):
They are taking up more space.
But that, I mean, what's what'sfascinating to me, I. Right
now is that we're at a momentwe're getting connected to other
humans has never been easier.
I mean, like you areconnected almost whether
you wanna be or not at atthe most epic level, right?
We're overconnected if,if we can put it that way.
And yet founders who'vealways had this really
(01:27):
isolating journey.
The nature of, of whatwe do is very isolating.
It's so unique to us and a lotof people don't understand it.
They've never beenmore isolated.
When I talk to founders nowadaysand I, and I say, Hey, and
I always, you know, you andI always check in on them
personally, it's always a bigpart of our discussions and they
say, you know, where are you at?
Who are you talking to?
More and more, I'm hearingpeople say, I'm really alone.
(01:49):
And I'm like, whatthe hell happened?
I think it's important for, forall of us and the, the folks
listening and, and Ryan, youand I in this, uh, episode, to
unpack why this is happening.
Also point out whyit's getting worse.
Yeah, yeah.
Right.
Like the horizondon't look good.
More importantly, what we canstart to do about it so we
can become less detached, moreconnected to other people and
(02:11):
feel less isolated as a founder.
Yeah, man.
It's interesting 'cause we've,we've done an episode before
on like the, the isolationthat comes with being a
founder just from being atthe top of something where
you, you don't have peerswithin 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'sgotten and some of the
causal things behind that.
(02:32):
So what do you, whatdo you think is the,
the, the first driver?
What's the, what'sthe big one for you?
I think we gotta
start with work from home.
Like, I, I mean, becauseit was global, it happened
to everybody all at once.
So it wasn't like a, a specificphenomenon in particular
within the startup community.
It fundamentally changedthe office place.
You know, uh, I had a foundercall me, this is so timely,
(02:53):
like an hour ago, and, andwe're talking on the phone.
Good friend of mine, a, aguy that, you know, he raised
a bunch of money and hejust, 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'sreally low per square foot.
Right?
Like, like for anywheremuch less San Francisco.
We were the buyer.
We were the, yeah, exactly.
Exactly.
And, and then he, hementioned without realizing
(03:15):
the significance of it, andhe is like, yeah, and so we
signed our two year lease.
I was like, wait, what?
Huh?
Uh, you signed a two yearlease 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 backjust four years, you'd be
lucky to get a 10 year lease.
10 year.
Yeah.
Yeah.
Nobody's pushinga two year lease.
(03:35):
Massive lease.
If you could
find office space at all.
Oh, I'm sorry sir. WeWorkis down the street.
Right?
That's what they would tellyou with a two year lease.
Exactly.
Didn't, that'd evenmore expensive.
The reason I say this isbecause clearly startups
have abandoned their offices.
En mass in order for that dealto even be, and he said that
office was sitting in a, in apretty prime spot for two years.
I mean, there crazy.
(03:56):
There was even just a fewyears 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 itpoints to is just the impact
that COVID and then the workfrom home culture has had in
how widespread it is now, Ryan,we were way ahead of this.
(04:17):
Uh, we, we started workfrom home 15 years.
I mean, 10, 15 years ago.
I mean, like sincethe beginning.
Yeah.
I would say like there,there's been at least some
work from home components.
Going back at least 12years, maybe 13 now.
And, and I say that 'causeI wanna talk about what the
cultural and kind of personaltransition became as we
went from partial work fromhome to completely remote.
(04:40):
Yeah.
So partial work from home,just for, for folks listening,
the partial work from homewas early on we decided that
on Wednesdays we would creatework from home Wednesdays.
Yep.
And if I timestampedthat, that's like 2012.
That's a very long time ago.
Yeah.
It was 12 or 13 and it was.
It was just intendedto be, well, we tried
it for the summer.
Remember?
It was like a, itwas a summer break.
Let's see.
Let's see what happens.
Let's give, let's give theteam a, a chance to try this.
(05:02):
And everybody loved it,obviously, because, uh, it,
it helped break things up.
You know, you only had togo to drive to work two
days in a row, ever in.
With that though, we are stilla, an office, um, based culture
and I wanna talk about whatcame with that, that we've
lost and just everybody's lost.
Right.
What came with that was forme, and I'm interested for
you, was just forcing meto get up in the morning
(05:23):
and shower and go somewherelike, and be presentable as
a human being to other humanbeings like that alone was,
was an important part of me.
Like, I'm a motivatedguy, so it's not like I'm
sitting in bed otherwise.
But like, just knowing thatI had to go present myself
to other humans, especiallyas a manager, mattered.
Like, like itchanged my outlook.
(05:45):
I didn't feel alonebecause I was knowing, I,
I knew I was going intoa room of other people.
Now when I get up and Idon't shower and I'm in my
sweatpants and I'm not gonnasee another human being in
person, you know that myfamily for an entire day.
That's way different.
That does get lonely.
Yeah, it does.
Yeah.
It starts to, you start tobecome quite isolated because
of things like that, andit's easy to fall into that,
(06:05):
and then just that becomesthe, the absolute norm.
I think that was right.
The big thing for me wasthat like a day or two here
or there, like that didn'thave any impact on me.
Zero.
Mm-hmm.
Right.
Like, okay, cool.
I'm not, I'm not gonna getdressed 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 thoseroutines with other routines.
(06:25):
Right.
So other things cameand fell into those
places, took some time.
But things likemeditation or breath
work, practice, uh mm-hmm.
Things like getting up andmaking lunches for my kids
in the morning, which Iclearly don't need to do.
My, my, my wife and I.Either one of us can do that.
Uh, at this point thekids are old enough, they
can do that themselves.
I like doing it and Ithink part of it is.
That sense of ritual in themorning and like this is the
(06:47):
beginning of productivity.
I'm creating something,it's gonna be beneficial
to somebody else.
And so I think in my case, it'sjust been a matter of replacing
those, but pretty arbitrarily.
Mm-hmm.
I think as those things wentaway, something else had to
come in and take its place.
Um, and at some point itkinda didn't even really
matter what it was.
They just, right.
I gravitate, food is oneof my love languages.
Right.
(07:07):
I like to feed people.
Yeah.
And so for me it waspretty obvious, like,
let's just go make food.
Let's make a great
breakfast, great lunch.
That works.
You know what's interestingthough, again, kind of mapping
back to founders specifically,you know, when you and I would
go in the office and we'd bewith other coworkers, leadership
team members, et cetera.
Yeah, yeah.
You know, we'd sit ina conference room from
time to time, we'd likego to lunch every day.
Like we had a lot ofinteraction where like
(07:29):
just daily frustrationscould 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 thinkjust the little social cues
that I had come to rely on.
Right.
Like, like even thingslike noticing that
someone's having a bad day.
Yeah.
Just their body language.
(07:50):
Just kind of, you know, how, howthey're responding, et cetera.
And being able to like leanin on that a little bit.
I always send a frowny facein 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, likenow I have no idea how
people are doing now.
This isn't to say like,Hey, why can't you ask them?
(08:11):
It's because there's adifferent level of decorum.
Well, there's also adifference between observing
something and having to ask.
Right?
If I have to ask howyou're feeling, that
leaves it up to you.
But when, when there's nochance for interpretation
or there's the chance forinterpretation rather, and
I can just sort of see likeyour body postures different.
Your body language is different.
Your energy feels off.
Uh, you didn't brush yourhair and you came to the
office anyways, like,what's going on bud?
You okay?
(08:32):
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 thosehealth issues and like I was
on so much medication thatI, I actually, I couldn't
sit up anymore and I'd haveto, like, we spent a lot of
time time in the conference
room.
Exactly.
Like I remember we'dhave these meetings.
Ellie and, and I talked atone point about mounting
a whiteboard on theceiling above the couch.
Nobody could lay down the starelike a planetarium slip up guys.
(08:54):
Yeah.
But like, I mean, I, I wason so much pain medication
'cause I was in so much painthat I couldn't function.
Imagine you guys never saw that.
Okay.
Like never saw me in that state.
And we're just wonderingwhy, like, I, I couldn't
respond on Slack or anythingor anything or on Zoom or.
You know, whatever our, ourtools are, I wanna map that
back to my feelings of, youknow, uh, how that makes me
(09:15):
feel as a founder as being, youknow, uh, isolated, et cetera.
When in that case, itwas a health issue,
which I would argue thatnearly every founder has.
But in that case, it was ahealth issue when no one can
even be around you to noticethat you're in pain, right?
Whatever form that takesand respond as a human,
that's isolating as hell.
It is.
Just the, the, by virtue ofbeing seen, because then you
(09:36):
know that people can observe it.
You can do, and, and we dothese things consciously
or subconsciously.
We send little cues that like,I need to be seen right now.
I need you to understandthat I'm going through this.
I need you to seethat I'm happy.
I need you to see, like, great.
You come into your oldbubbly, you're like, well,
you've got something youwanna tell the world, right?
Something good happen thatyou want to share, right?
Conversely, when the other,when there's something that you
don't feel comfortable sharing.
You want to have itdrawn out of you.
(09:56):
That needs to be observed toowhen you're on your own by
yourself and nobody can do that.
When you can't be seen.
It creates this additionalburden 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.
(10:17):
Yeah.
When it becomes everyday, everybody's in
that same situation.
So there isn't this otheropportunity like, well,
because you observed themdoing that, now here's my
chance to share my piece of it.
It doesn't worklike that anymore.
There's, there's another sideof it too, which is when you're
in front of people and youdo or say something that they
appreciate, you get a bit ofa, a, a, a visual, emotional,
(10:37):
social cue that tells you,you did something right.
Like some, one of the thingsI, 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 somebodyor tell them that they did
a good job with something.
'cause I knew it wasimportant to them.
And I do that now in Slack,but it, it lands so empty it
does not hear the same at all.
(10:57):
Not at all.
At all.
Um, and, and, and here's whatI think about it goes the
other way too, when someonewould say, Hey, you know, I
really appreciate you helpedme 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 knowthat I'm doing a good job.
Yeah.
My default assumption has alwaysbeen in my 31 years is that
everyone hates me and they justtolerate me because of that.
(11:21):
Having no cues to tellme otherwise is painful.
Yeah.
Now I'm used to it, butif I were three years in
my career as a founder.
And I had no way to get asocial signal from humans,
my, my fellow humans.
Yep.
That they're reallyhappy with me.
Right.
Without, like, surveying them.
(11:41):
I think that would be veryisolating after a while.
It is.
I I, this was a, a conversationthat came up a couple weeks
ago in, in one of the foundersgroups, and it was this
notion that somebody broughtup 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 broughtup this aspect of it was like
yes and no, because there's,there's so much noise,
(12:02):
there's so much isolation.
Yes.
The technical side of things,the product build side of
things, um, the content creationside of things, yeah, you've
got some tools now that makethat a lot easier, but I would
argue that especially for earlyfounders, young founders, first
time founders, the human aspectof it has gotten so much harder.
The idea that we wouldhave a meeting where not
(12:23):
everybody was sitting inthe 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 toolsnow and you know, you, you
said Slack, but I, I wannacall it even like Zoom,
where we can see each other.
We're using it right now torecord this podcast, but it
still hits different, right.
I, you still don'tget the same cues.
And I, I think back, I'm like.
(12:45):
Okay.
I'm not gonna say I have nofond memories from a Zoom call.
Some stuff has happened onZoom calls that were great.
I have a thousand fond memoriesfrom like crappy interactions
in our office kitchen rightover bad coffee, right?
Yep.
Because I. We were there, wewere present, we were social,
we were, we were together.
We could read the cues.
You know, it's funny you shouldsay, I, I've always had this
thing where I think about howmuch time I spend in a digital
(13:06):
world, and I've been a digitalnative since the eighties.
So like, I've been atthis for a long time.
Yeah.
And, and I've played countlesshours of video games.
And I, and I, and I thinkabout how many of those video
games do I have a lasting,like highlight, like life
highlight reel from Yeah.
And, and what's funny isevery single one that I could
come up with where I triedto remember like a meaningful
(13:27):
moment, a memory where I,where I played a video game,
nearly every single one ofthose memories had to do with
the person sitting next to me.
Yep.
When I was playingit like I like.
You probably remember thetime that you finally figured
out how to beat King Hippoand Mike Tyson's punch out.
Right.
And I remember Jay Faanlike had just unlocked it
'cause he'd figured it out inNintendo Power Magazine and
(13:47):
like that was a big moment.
Yeah.
Yeah.
That's, I can't tell you anyNintendo power like I got, but
it, but it was more about twoof us in a sleepover having
like this, you know, this.
Fun time.
Same with Zoom, same withdigital media as a whole.
Think of how many memoriesyou don't have by scrolling
through social media.
I mean, that one time where Iwas, I was scrolling through
social media and had thebest time of my life, right?
(14:09):
Like happens.
Never.
No, you're just, you'repouring dopamine in there.
But to know no end, I thinkit's, it's interesting.
I think that.
Again, you and I have beenin the part of the digital
world since the digitalworld became a world.
Right?
And so originally the digitalpiece was a conduit to
experiences, mostly with otherpeople, to your point, right?
Like it was the memory offinally making it past that
(14:31):
level in Sylvania, or, you know,trying our hardest to, to make
it further than the first levelin contra with only three lives.
And then all of a suddenthe digital piece became the
experience as opposed to beinga conduit to the experience.
And I think that was whereit really started to change
and become something thatwas less, less palpable,
less social, less.
Less everything.
Let's isolate that.
Let's, let's say, yeah.
(14:51):
The, the isolation quiteliterally of us from other
humans on a daily basishas really locked in this
sense of not just physicalisolation, but mental isolation.
Yeah.
Which is keeping us from havinga lot of the little interactions
that actually did keep us going.
Now you're gonna hear somefolks, uh, say rightfully so.
(15:12):
It actually worked out greatfor me because I'm an introvert.
I hate being around otherpeople and that did nothing
but create anxiety for me.
Awesome.
I, I'm, I'm, I'mglad that's a fix.
But I'm saying for a lot ofpeople, whether they realize
it or not, particularly peoplewho've never had an in-office
experience, it's not the officethat, that they're missing.
It's the interaction withhumans forced or otherwise.
The office itself usually
(15:32):
sucks.
Yeah.
The science is there,productivity's higher.
Lots of, lots of good thingshappen with, with remote work.
I think there's a coupleof flaws in all of this,
which one of them beingthis 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 doingthe remote thing for, for longer
than most, and even there, it'sstill, you know, we're still the
(15:53):
first generation at, at at, atbest, and most people have been
doing this since the pandemic.
So we're a couple years in.
So I think there wereproductivity and there was all
these things that did happen.
But I feel like the socialdegradation piece of it,
the, the isolation piece issomething that builds over time.
I don't think we'refully recognized exactly
what the downsides are.
I agree.
I agree.
So, uh, let's move onbecause I, I think that
(16:13):
one is very obvious.
I mean, it's very visual,it's very visceral.
The other that certainly camebefore it that I think has
sadly done far more harm thangood would be social media.
And, and, and the idea.
Of replacing our interpersonalconnections with a digital one.
Yeah.
I thought you were gonnasay motor cars, but Yes.
(16:33):
Social, socialnetworks probably.
Now, here's the thing, I'mnot anti-social media, but I,
I think we, we've definitelycome to a milestone point with
social media and I think it's,it's becoming well recognized.
It's really messed usup in a lot of ways.
And I think one of thebiggest ways, it gave us the
illusion of connection withoutactually having connection.
(16:54):
Yeah.
It gave me the illusionthat such a super level, I'm
connected to lots of people.
Right, right.
I had an in-person relationshipthat was meaningful and it
was, you know, and, and, andthere were memories attached
to it, and it got extended.
By virtue of, of socialmedia, 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.
(17:15):
Yeah.
I think the idea that, thatwe increased the frequency
with which people could sortof tap into our lives and see
the stuff that was happeninggot traded for, for the depth.
Right.
We took, we, we tradedsuperficial frequency
for, for true depth.
I remember it was probablythe third or fourth time.
I had asked this question, heardsome version of the same answer.
It was like, oh man, whenwas the last time we talked?
(17:37):
Right.
They just all of a suddenlike realizing it had
been a long time sinceI talked to this person.
They're like, oh yeah, butI keep, I keep tabs on you
with, uh, via Facebook.
And like the first time I heardit 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 nottalking 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.
(17:57):
And that's, that's enough,except that it's not right.
It's absolutely not.
Let me dig into that a littlebit more because we're trading
different types of interactions.
Yeah.
Dramatically.
And it has a, a strong presenceto it and not a good one.
For example, back in the day.
You know, when we were hostingall these events, we had
thousands of people at, at ourhouse, most of 'em founders.
We'd spend time at cocktailparties and you, you'd hear
(18:19):
the, the emotion and theexcitement and the terror
of other founders and whatthey were going through.
And you know, one of thethings we did for decades is
we'd get a bunch of foundersin a room and we'd just.
Talk shop.
Everybody would just talkabout what they were working
on and what their concernswere, and they were the amazing
conversations, wildly connected,built friendships overnight.
Like it was incredible, butevery had everything to do with
(18:41):
being in front of other people.
When we tried to replicatethat, which we did, I mean,
we specifically tried toreplicate that like same idea
with doing it all digitally.
We struggled because all ofa sudden the, the lack of
presence made it more difficult.
The communication channelwas there, but there
was something missing.
I
think part of it became thatlike vulnerability went away.
(19:01):
I think it's a lot easier tobe vulnerable in, in person
when you can see the reactionto it and you can control
how many people see it theminute you post it on a
social, social media, right?
It's, there's no control, right?
I'm vulnerable now to anyonewho happens to come across
this, and so everybody juststarted posting the positives.
And so good news guys, there'snothing bad happening to
founders anymore at all.
We don't have to havedinners and talk about it.
(19:22):
The downside, 'causeeverybody's just kicking
ass and taking names.
Fantastic, right?
That's what it feltlike for a while.
It was like just everybody'sInstagram version of
their startup man wasthat bad for everybody?
I.
You know something that'sreally funny about everything
we talk about here isthat none of it is new.
Everything you're dealingwith right now has been done a
thousand times before you, whichmeans the answer already exists.
(19:45):
You may just not knowit, but that's okay.
That's kind of whatwe're here to do.
We talk about this stuff onthe show, but we actually
solve these problems alldayLong@groups.startups.com.
So if.
Any of this sounds familiar.
Stop guessing about what to do.
Let us just give you the answersto the test and be done with it.
The performative part hasgotten geometrically worse
(20:07):
with time and, and becauseit compounds on itself.
Well, if everyone else, allmy other friends are saying
that, that, that they're havingthe best vacations and best
spouses and best whateverin their life, then I guess.
I have to, and when Iget a chance to respond,
I'm gonna make mine asover the top as possible.
I need the best possible photo,I need the best possible filter.
Yep.
I need the cutest possiblecaption, you name it.
(20:28):
Right.
And all of these thingsare performative, right?
I'm, I'm doing it becauseI have to perform now
to, to an audience.
You leave that spotlight on24 7 and you keep perpetuating
that, that doesn't lead toa positive place because.
Newsflash, if you're a founder,you are not happy all the time.
You're depressed as fuck, right?
(20:49):
And I think, uh, part of thechallenge is we've now got
this distorted reality aroundus where it's compounded.
Every person that I'm seeingin my feed is doing amazing.
And so immediately if I gothrough my feed, actually,
uh, I hardly ever usesocial media, truth be told.
And sadly, I don't wannacall myself selfish.
I'm just doing other stuff.
(21:10):
I never look atother people's stuff.
I have no idea what my friendsand family are doing, like
on social media, media, atleast the Facebook version
over the Instagramversion 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 careabout those people.
I don't care aboutfollowing all those updates.
Yeah.
And so anyway, when I do go onthere and the rare times where
I'm actually scrolling throughmy feed for something and I see
what everybody else is doing.
(21:31):
My first thought, becauseI'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 photoof you and your family.
Like, dude, I talkedto 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 niceautumn scene where all of you
are, are in an orchard somewhereand uh, is a healthy pumpkin.
(21:52):
Look at that.
Yeah, with a very healthypumpkin, 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 thatand you're like, oh my God, my
life must suck by comparisonbecause yeah, the contrast
becomes really dangerous,but you know, it's bullshit.
Yeah.
But you can't ignoreit either, right?
(22:12):
Like this is whatseems to happen.
Like we, we, we do know, andyet 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 homething, I'm not sure there's
that much you can change there.
I think there are some thingsyou can change within social,
uh, social media, but maybeeven more so like, how do
we start to carve out somesome safe private spaces.
(22:33):
Uh, you know, is it, isit going back to doing
the small dinners thing?
You know, where do we getthe unfiltered talk again?
How do we do this?
I'm going throughthis as we speak.
Uh, right now, uh, I'm goingthrough all the people that
I wanna stay in touch with.
I'm basically just creatinga giant list of people that
I'm gonna text and call likea catalog of like faces,
like a, a book of fa likea Facebook facing book.
(22:57):
Yes.
But, but instead of likegoing through feeds and
everything else like that.
Yeah.
I'm gonna make aconcerted effort now.
Now here's the, the,the key word there.
Effort to make sure thatall the people that I care
about, that I'm activelyreaching out to them.
And typically when I reachout to somebody, we end up
following by grabbing a lunch ora dinner or something like that.
Yeah.
It has occurred to me.
I, I'm declaringrelationship bankruptcy.
(23:17):
I. Which is to say I nolonger believe that I can
develop or sustain any ofmy relationships digitally.
Yeah.
Yeah.
I just don't believeIt doesn't work.
It doesn't work.
I can send messages.
I can create updates.
I can follow updates.
I don't actually thinkthat I'm gonna build
a better relationshipwith anyone in my life.
Digitally?
(23:38):
No, I think it goes back towhat I was saying before,
which is that digital usedto be the conduit, right?
So we would, we wouldmessage somebody and say,
Hey, let's go grab dinner.
Right now, it's just, Hey, I sawthat dinner you had last night.
Those appetizers lookgreat on Instagram, right?
I think over time it's justtaken such a different form that
it's not, it's really keepingus from taking that next step
(23:58):
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'sbeen, 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 hotbedof startup activity.
Right.
I have good friends.
I've, I've, I've built greatnetworks here and we do a lot
of interesting things together.
(24:19):
And I do have some otherfounders around, but it
is not the same thing.
It is absolutelynot the same thing.
And so as we're, as we arestaring, you know, we're
as, as of this recording 23.
Days away fromheading to Madrid.
Um, I've already startedsetting up founder Coffees,
lunches, uh, some people withinthe startups.com network.
Some people without, I'msuper excited about it, right?
So I think this is me.
I also like, I. Not only didI have to de declare, uh,
(24:41):
relationship bankruptcy, and Ihad to, to restructure in a way
required actually physicallymoving myself somewhere
where it's more possible.
Yeah.
I gotta tell you, every timeI make a concerted effort,
like I, I, I get on the phonewith a, with a friend or you
know, I meet somebody out orwhatever, that fills up my
bank account of contentmentof I guess being seen.
(25:02):
If, if you wanna say,that's the thing.
So much more.
In fact, it gets.
Zero filling when, when I'mtrading a DM with someone.
Yep.
Right.
Like I kind of look at allof those things like dms, et
cetera, like the equivalentof, 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, itshould just be the preamble,
(25:23):
right?
This is just the Yeah, yeah.
Yeah.
Again, I understand it worksdifferently for everybody,
like, you know, we're comingfrom a bit of a different
generation where that was, uh,we, we can see the contrast.
Maybe a little bit differently.
Whereas someone growing upwith all these tools right now,
and it's all, they know, theirlevel of what a relationship
means is gonna be dramaticallydifferent because their level
(25:43):
of relationship might mean wedo talk every day on dm and
that is how, that's how allmy relationships are built.
So why would that beany better or worse?
Which I'm, I'd be really curiousto dig into that at some point.
Uh, but we'd need somepeople on here who are kind
of native to that epoch tobe able to say that like.
Yes.
And those do fulfill me.
Like is it, is it the contrast?
Is it the delta from what weknew to what we have that's
(26:04):
bothering you and I or are theygonna experience the same sort
of superficiality and, and samechallenges that that we have.
I think that in person, notwith everybody, obviously,
but I think in person youget a level of vulnerability
and authenticity that isyes, really difficult.
To replicate outside ofthat, not impossible.
Yeah.
Again, and, and differentpeople have different
(26:25):
ways of communicating.
I could see somebody elsecoming on and saying, you know
what, I see the polar opposite.
I'm really nervous whenI'm around other humans.
I can't express myself.
But when I go to a, a forumwhere I can be anonymous,
read Reddit and say exactlywhat's on my mind or, you know,
share, I feel so much better.
And that fills me up, youknow, in, in, in my way.
I could get that.
Yeah.
Uh, I get that.
Just how I feel.
(26:46):
Yeah.
It hasn't workedthat way for me.
Uh, you, you saidtwo, two words.
One, one of 'em we had talkedabout a bit earlier, which
is vulnerability and theother one was authenticity.
Man, for as much as I amenjoying 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 strippedaway so much of the
(27:07):
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 vaporizedmy personality outta
this piece entirely.
Yep.
Made some goodgrammatical corrections,
but my God, I'm gone.
I'm gone.
This is gonna take the othertwo categories we talked
about, about, you know, workfrom 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.
(27:29):
We are huge fans of ai.
Right, so, so this isn'tone of those cases where
like, we're about to goon some anti AI ramp.
This is, no, AI is awesome, butwe 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 probablygonna happen too.
It's something that, what reallyconcerns me is that we are now
(27:50):
taking away tons and tons andtons of human interactions.
And we're not replacingthem 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 customerservice rep, and I, I always
do a thing with customerservice reps where I always
try to make them laugh.
Yep.
I know that sounds odd,but I picture those
(28:12):
people hating their jobs.
I remember when I usedto have to make a hundred
phone calls a day when I wasdoing outbound uh, sales.
It's awful.
And it sucked.
So I, I never forgetthat experience.
And I always try to makesomeone laugh and, and tell
the, and I always tell.
You have a really nice voice.
You're
very pleasant.
Wow.
That was the fastestanybody's ever solved a
problem like that for me.
Yeah.
Why not?
Uh, I also get way bettertreatment when I do that,
(28:33):
but my point is there'sjust a little bit of, of,
of interaction, right?
There's a, I I make someonelaugh and, and I just,
that there's that littlebit of humanity there.
Now, compare that towhen I'm in a chat bot.
And I know damn well there'snobody on the other side.
Yeah, I know.
I'm fighting an algorithmto try to get an answer.
If talking to customerservice sucks and it does,
talking to an ai, even if it'smore efficient, which I do
(28:54):
appreciate, feels so lifeless.
It, it
is, uh, quite literallyand isolating.
I'm, I'm basically nowon the phone with myself.
Right.
Which is.
Bizarre.
Yeah.
You're on the phonewith yourself.
Yeah.
You're, you're, you're tryingto solve a problem that might
have even come from isolationand now you're being more
isolated in order to do it.
Right.
Like, it just feelsabsolutely amazing.
(29:14):
And again, like you said,we're, we're not anti AI at all.
I use it daily.
I think in, in the contextof 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 wereabsolutely not people.
I watched multiplecomment thread happen
on a, on a post of mine.
(29:35):
I'm like.
None of those are,those aren't humans.
Those are two people's AIarguing about my posts.
I'm like, this isnot amazing at all.
And, and in the same way, youknow, the big thing now is if
you see the, the M dash lineused in someone's copy, you
know that it was written by GPT,
which pisses me off becauseI was an m Dasher man.
I've always been an m dasher.
I love the dramatic pause,I love to call it out.
(29:56):
Like I love theuse of the M dash.
And now every time I see Mdash and I, or if I'm thinking
about using one, I'm like.
Nope.
So I'm just gonna startdoing something else.
I don't know what I'mgonna stick in there, but
I'm gonna start stuffingsomething in there.
Um.
So I like that.
So with, with that said,we get in a situation where
all of a sudden, like withthose comments, we have
to start second guessingauthenticity all the time.
(30:18):
Yeah.
Yeah.
When I looked at, at my LinkedIncomments, I can always tell
the AI generated ones becausethey're always self-referential.
It's, it's always somethinglike, 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 foradding nothing to this
conversation, by the way.
That never adds anything.
It just
reiterates exactly what I said.
(30:39):
Yeah, now I get it.
I get it.
But to your point, withina year, two years, I.
75 to 80% of my comments aregonna be AI generated, and
I'm gonna look at it and say,okay, well that has no value
anymore because, uh, theauthenticity has been removed.
Now it does create a differentopportunity where if you
can, if you can start to,to deliberately become a.
(31:00):
Authentic and whatever thatlooks like, then people will
be more interested in that.
Okay.
So for example, uh, thisis gonna sound crazy.
I think within five years,getting on the phone with a
customer service rep is gonna beconsidered a premium experience.
Yeah, a hundred percent.
I, I genuinely feel like,like that's gonna make, oh
my god, thank God they havea human that I can talk to.
(31:21):
Yeah,
there's a human, I thinkthat all customer service
numbers are gonna be one900 instead of one 800.
They're gonna be thehighest paid people.
They're gonna, they're gonnabe like, like $300,000 a year.
People that, um, thatactually get on the phone.
But I think the other side ofit is with AI automating so much
of what we can do, it does takesome of the, do I really have to
(31:43):
put much more effort into this?
Or do I really have to be,you know, more authentic?
Not really.
I think about how muchlanding page copy you
and I have written Yes.
In the last 20 plus years.
Okay.
And how we don't really haveto write any of it anymore.
All I have to do is gointo AI and say, here's
roughly what I want to say.
Yep.
And it's gonna giveme a 90% version.
(32:03):
Now, as a guy who writesfor a living, does that make
me feel a bit more useless?
It does, but it alsoallows me to not have to
put in that extra effort.
To make it feel more real, tomake it feel more punchy, to
make, you know what I mean?
Yeah.
Like, and, and so I guess whatI'm saying is when we're going
back to, uh, isolation, wehave all these channels that
are getting diluted from us.
(32:24):
All, all the different wayswe're connecting with humans
now we're getting to the pointwhere 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'sa human behind it,
right?
My God, the, the lastthing social media needed
was it was a way to becomeeven less authentic.
Yes.
That's what I'm saying.
Unfortunately, like at,at some point and, and it
(32:45):
will happen, we're probablyreally close to it already,
but all of this efficiency.
Without humanity just becomesnoise at an epic scale.
That's all it becomes.
And then, and then it'll becomeabout unwinding that, right?
I've decided that in 2026,I'm just gonna start sending
emails that are only photosof handwritten letters with a
bloody thumbprint on the bottom.
(33:05):
Right.
Proof of life.
I'm gonna, that'sall I'm sending.
I'm not gonna type anythinganymore because there'll be
a renaissance around that.
And it's gonna be hystericalto see the ways in which
it comes, but like.
Proof.
Proof of life or proofof human input is gonna
become a thing, right?
Like, yep, this is me typingthe email that I'm sending you.
Here's a video of me actually
writing it.
Enjoy.
The irony is we're all about tostart paying a massive premium
(33:26):
to go back to the oldie timeyways things were done and,
and it's going to seem so.
Premium.
Yeah.
Like I said, when when youget 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 lotof people, you know, we're
seeing just the beginningof, of, of AI for sure.
But when we start to removethe human element, the human
(33:47):
layer of so many interactions,and again, especially among
startups, 'cause we tend toadopt this stuff first, so,
so again, this is being youon like our LinkedIn profiles
where we're posting every dayand all of a sudden our common
threads are getting real busy.
It's not with people anymore.
I'm looking at thatgoing, Hmm hmm.
Before I wanted to postsomething because I really
wanted to engage my audience.
Yep.
And I wanted to hearwhat they have to say.
(34:09):
Now I kind of know if I postsomething, I'm just going
to get a bunch of bots.
I'm gonna spend half mytime second guessing which
one of these are peopleand which one aren't.
Right.
And copy pasting some of theminto 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 gettingsome, some, uh, some good heat
and, you know, there's, therewas some engagement, but as soon
(34:30):
as everyone found out about it,mind these are all like, like.
Startupy people, theyspammed the hell out of it.
Now there's like, they'readding like 10,000 users a
month, but not a single one ofthem I think is a real human.
Yeah.
And any of them, they are, arejust 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.
(34:51):
I'm just, you know, usingit as, as a stop point.
That same audience or, orcommunity would've been much
smaller, but it would've been ahundred 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
(35:14):
versus who they actually were.
And I think where this isgetting interesting for founders
is think of how many placesRyan we're trying to turn to,
to vent, to express, to share.
And it's like they'reall shutting down.
Yeah.
Like one door at a time.
It's getting harderand 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
(35:36):
is now the default setting?
I. Whether we're, whetherwe're out and doing things.
I mean, that's the, that'sthe craziest part about
it to me, is that evenif you are being social,
you're doing it digitally.
You're not really Right.
Right.
So you're, you're still gonnabe as lonely as ever while
taking action, which startsto feel really self-defeating.
So how do we, how do westart to combat this?
Like, what do we do?
Like we have to, we have to
figure out a way to, to connect.
(35:57):
I just lay thegauntlet down myself.
I, I said, uh, as far as I'mconcerned, the idea of, of
nurturing social networksand stuff like that is not
my goal at a shutting downpersonal level anymore.
Shut down.
Yeah.
I just don't care.
I'm gonna go back to allpersonal, like, you know,
direct connections with people.
Crazy sounds, phone calls, andlike I say, text message, which
isn't the most personal thing,but it's not the same as me
(36:17):
just posting an update on, on asocial network and saying, Hey.
Yeah, giving
a thumbs up on your, onyour, your, your kid post.
Yeah.
The other funny thing isnow when I text people.
It's almost like it'sa 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 nextto 'em like, well,
whatcha doing here?
There
we go.
You know what's funny, man?
(36:38):
I, I remember one of the firsttimes that something, one of
my personal interaction tropes,the thing that I did for
years and years and years, Iremembered people's birthdays.
This was something thatI did and that people
really respected.
Like I would reach out tothem, Hey, I sometimes I'd even
do it the day before, right?
Like just like, Hey, youknow, I hope you, you got some
(36:59):
fun plans for your birthday.
And people always loved the factthat I remember their birthdays.
Then everybody's birthday startsgetting plastered everywhere.
Now LinkedIn knows,Facebook knows all that.
And it took that away from me.
And I remember being reallybitter about that for a
minute and I was like, andnow that I think about it,
how many other things likethat has it taken away?
Right?
You don't have to reallyknow anybody to look
like you know everybody.
(37:20):
And that's shitty.
I hate it.
It's so funny youshould say that.
'cause I actually had almostlike, kind of like an opposite
reaction coming from a differentdirection, uh, years ago.
It's like when, when socialmedia was just starting, I
was at one of my high schoolreunions and I haven't kept
up with many of my classmatesin, in high school just 'cause
they were different states.
But, um, I think maybe
they haven't kept upwith you, but like, I, I
just, I'm guessing there.
(37:41):
Oh yeah, that, thatwould also be true.
But I show up and the, thegal 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 youknow that, that I had a kid
much less what her name is?
And now again, this isgonna sound hilarious.
This is like at the dawnof social media and it
occurred to me that likethe, that information
(38:04):
is no longer private.
Like, I mean, you couldchoose not to share it, but
I'm just saying in generalanymore those things that
to your point, someone wouldactually have to know because
you told them and sharedwith them are more common.
And now it's still throws mewhen I meet with people or
see somebody that I haven'tseen like in 10 years and
they're like, man, uh,that closet that the master
closet you just finishedfor your wife is incredible.
(38:25):
And I'm like, shit, Ihaven't seen you in 10 years
and you know what projectI finished this weekend.
Right.
And again, it's not that I haveno idea how social media works,
it's that exactly what you said,the uniqueness of having to
actually know me and know whatI 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 oneof the more dangerous pieces.
(38:45):
I think.
I, I look at it this wayand I look at the way
people use technology.
I respect when peopleuse technology to extend
something they were doing.
Correct.
Yeah.
I do not respect technology whenpeople use it to jump to the
line, to get to the same placesomebody else did without all
the effort that they put in.
That's annoying to me.
That's annoying tome every single time.
So here's the thing, I, Ithink we're, we're at a point.
(39:07):
With all of this, right?
When we think about isolationas founders, we're connecting
to humans and, and basicallytaking away our isolation
is actually a full-time job.
It's not something that we canjust do in the background where,
oh, you know, I guess I'lljust 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 isolatedas a founder, almost all.
(39:28):
All of us do.
Yeah.
If you really wanna build thatcircle 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 youhave to go raise capital, you
have to go make a concertedeffort to build the people in
your life, the vulnerabilityin your life, the sharing
and connections in your lifethat you can't get digitally.
Because if you don't takea concerted effort toward
(39:51):
getting all of this done,your isolation is gonna be a
hundred times worse, and that'sthe worst possible outcome.
Overthinking your startupbecause you're going it alone.
You don't have to, and honestly,you shouldn't because instead,
you can learn directly frompeers who've been in your shoes.
Connect with bootstrapfounders and the advisors
helping them win in thestartups.com community.
(40:12):
Check out the startups.comcommunity@www.startups.com
to see if it's for you.
Could be just thething you need.
I hope to see you inside.
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