May 19, 2025 • 31 mins
Ryan and Will delve into the complexities of maintaining a healthy relationship with your startup. They discuss their personal experiences and challenges in balancing the demands of a startup with personal well-being. Will shares an incredulous story about a friend enjoying a Tuesday afternoon in the pool, leading to a broader discussion on the importance of setting boundaries and recognizing the signs of burnout. The hosts emphasize the need for self-awareness, prioritizing personal values, and finding joy in the journey, not just the destination. They also touch on the benefits of giving team members autonomy and creating a supportive, non-toxic work culture.
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:
00:32 The Pool Story: A Lesson in Work-Life Balance
02:08 The Toxic Relationship with Work
03:11 Startup Therapy: The Podcast's Origin
08:15 Balancing Work and Family
13:17 Non-Negotiables and Personal Values
14:51 Conclusion and Final Thoughts
15:35 Mitigating Guilt Through Productivity
17:29 The Elusive Goal of Profit
19:21 Emotional ROI in Startups
21:57 Autonomy and Company Culture
24:50 Balancing Safety and Happiness
28:26 Avoiding the Trap of Obligations
29:40 Creating a Non-Abusive Startup Relationship
30:50 Join the Startups.com Community
Mark as Played
Transcript
Episode Transcript
Available transcripts are automatically generated. Complete accuracy is not guaranteed.
(00:00):
Welcome back to their episodeof the Startup Therapy Podcast.
This is Ryan Rutan,joined as always by my
friend, the founder,and CEO of startups.com.
Will, Schroeder will, we'vehad very, very interesting
relationships with our startups,with our work over the years.
It's necessarily whatI would call healthy.
We poured a lot of timeand love into them, and.
Sometimes they've given backto us, but I don't think we've
(00:21):
ever really truly demandedmuch back from our startups.
But that's not necessarilytrue for everybody else.
Right?
And so I think we gotta talkabout like the difference
between being a founderand and how to balance
some of that stuff out andkind of what it looks like
for the rest of the world.
For example, you evercalled a friend at two
o'clock in the afternoon,like Tuesday to find them
floating in a pool and just.
Found yourself incredulous.
I remember I told you thisstory after it happened.
(00:42):
This was like a year agoand I'm driving home.
Actually it's funny, I wasdriving home after teaching
the entrepreneurship class atmy, my kid's school and I was
calling a friend of mine 'causehe was kinda like on route
to where I was headed next.
And I was two o'clockon Tuesday, a beautiful
like summer, afternoonor spring afternoon and
I'm like, uh, hey man.
What you up to?
He's a senior executive at apublic, uh, technology company.
Right.
And he's a sales executive.
(01:02):
Right.
His whole life he has beenon the ground selling.
Right.
Like, he understands performancemetrics better than anybody.
Well, except when he is in thewater, uh, not selling well.
Okay.
So, so he's also oneof my oldest friends.
And, and so I was like, Heyman, what are you doing?
And he said, uh,I'm in the pool.
I'm like.
Huh?
Uh.
Like, what do you mean?
He, he is like, yeah,I'm sitting in a floaty,
(01:24):
floating in my pool.
I'm like, and this is, thisis what's so funny, Ryan.
I was like, how?
I was incredulous.
Yeah.
Like how could you Possibly attwo o'clock on a Tuesday, right?
When there's work to be done.
Yeah, there's work to be done.
Why depend on you,
sir.
And so my first thoughtwas to fire him.
(01:44):
My second thought was thatit doesn't work for me.
It doesn't work for me.
Yeah, I can't, I just go throwhim a cinder block in the pool.
But here's the best part.
Here's the best part, like,and again, I've got a great
relationship with, I'veknown him for a long time.
My response was kind oflike, I. How, like, how
could you possibly do that?
And, and this is all he said,he goes, makes me happy.
It makes me happy.
Like, and, and oh, just thanksfor making it worse right now.
(02:05):
Now I really don't understand.
Found.
I was like, that'sthe worst answer ever.
Right.
And, and again, I'm, I'mtelling this story to
set the premise here.
Of what a toxic relationshipwith work looks like.
And we're not talking about his,we're talking about mine, right?
Like it didn't occurto me like first blush.
Again, I'm, I'm not thatlike one dimensional, but
it didn't occur to me thatyou could just do that.
(02:27):
That you could just be sittingon a Tuesday in the middle
of the work week in your pool'cause it made you feel good.
I was like, there's gottabe some business purpose
to what's going on.
Right?
And that's whereour story begins.
We dig deep enough into it.
You can find that, right?
Like, I think as, asfounders, we often
conflate hustle with value.
And you know, we think if we'renot, if we're not chained to
our lap to 24 7, we're slackingand not the kind of slack
(02:49):
where we're, we're talkingto the rest of our team.
Not that slack, like justthe not doing anything
kind of slacking.
Guess what, like, productivitycan be floating in a pool at
2:00 PM if it recharges yourbrain, if it gives you the
energy you need to go back inand, and do the things right?
Like we know what the, the,the cost of burnout is.
This is the cost of thetherapy that keeps us from
getting there, I suppose.
Yeah.
And you know, one of thethings we do a lot of.
(03:11):
On this podcast, 300 episodes.
I mean, like, you know, we'vealmost, man, it's like 2
97 or eight or something.
Oh
damn.
I didn't realizeit was that close.
I just we're real close.
I rounded it up for charity.
When I think about, you know,all the topics we've covered,
and some folks know this becausesome folks that listen know us.
Most of what we talkabout here is a reflection
of our own journeys.
This is Ryan and I in ourown therapy, the startup
(03:33):
therapy we're generallytalking about Is ours ours?
So,
and a lot of peoplewill comment.
They'll say like, Hey, it justsounds like I'm in the middle
of a conversation of two people.
Like unpackingsomething between them.
It's 'cause you are, that'sactually what's happening.
Do you remember back like,this is 20 17, 18, somewhere
in there where we were like,we should do a podcast,
and then we were like.
(03:53):
What should we talk about?
And we went through allkinds of iterations, like
start up daily, we couldcover some news, we could
do all this different stuff.
And then finally we're like,you know, what about those
conversations we have everyweek anyways, where we're
just talking about like,what are you going through?
What are you going through?
How are you dealing with it?
What have you been through?
Yep.
And we're like, whatif we just hit record?
Yep.
And then we did.
And so here we are.
So to your point, it is verymuch just listening in on the
(04:15):
conversations of two people wholive through this stuff daily
in the ironies.
If you listen to this longand they're like, man, those
guys really need therapy,which is totally true.
Not anymore.
Yeah, yeah, exactly.
On a weekly basis.
I say this to, to set the tone,to say a lot of this isn't us
talking down to founders saying,here's what you're doing wrong.
This is in real time, sayingthis is what we're doing
wrong, like right now.
(04:37):
Right.
And the self-awareness of it,of being able to say, Hey,
you know, something's broken,doesn't make it go away.
I wanna start there.
For me, I'll just kindapoint to myself here.
I've spent the last 31 yearsin a very specific kind of
mindset, which is if I'mworking, I'm valuable And okay.
And if I'm not working,I'm guilty and not now
(04:59):
that is wildly unhealthy.
I just wanna be clear.
Right.
Wildly unhealthy pays well,but it's wildly unhealthy.
You said
this before, but it's,it's, it was fear.
Motivation.
Yep.
Right?
Yep.
And, and, and it'sabout safety, right?
Yep.
So for you, it's like,if I'm working, I don't
have to be afraid becauseit creates safety for me.
Right?
So as long as I'mworking, I'm safe.
Hundred percent.
Yeah.
I
mean that's, that'sa lot to deal with.
It is, right.
It's a, it's a hellof a lot to unpack.
(05:20):
I think what we buildup with that is a
tolerance for discomfort.
Oh yeah.
Right.
In, in so many ways.
So in the way my buddyis floating in a pool and
he's saying, Hey, I am notcomfortable at work right
this minute, I'm gonna godo something comfortable.
My res response to, tonot enough comfort is work
more because that willsomehow create more comfort.
(05:40):
And sometimes it does.
Right.
But I guess what I'msaying is if we zoom out.
As founders and we say,Hey, is my relationship
with my startup healthy?
Ergo Sure.
Does it pay me back inmore ways than cash?
As much as I put into it.
For everybody listening,
like I'd say 99% of youcan listen to this and me
just say, probably not.
(06:02):
Yeah.
There's gonna be a few of,you're like, no, I actually
have a very, very healthyrelationship with this.
Yeah.
Most of us don't.
For those of you that do,please create a podcast, Ryan,
and I would love to listen toit and take, I'd love to, can
follow along and do what you
do.
Yeah, just send me a notethat tells me I'm wrong.
That'd be great.
But for kind of everybody else,I think part of it is because
when we go into this, Ryan, likewhen we start something, you
start something from nothing.
(06:23):
It is, there's a voluminousamount of weight in
work and commitment,discomfort and frustration.
I think because we come toexpect that it builds a pattern
behavior where we just assume.
That's how it always has to be.
It's essentially starting in anabusive relationship and using
the abuse as the baseline forhow the relationship works.
(06:47):
That's how it
functions.
Yeah.
You know, I think, andagain, look, there's, there's
reasons for all this, right?
Part of it is that whenwe breathe life into
something new, that's it.
We're literallybreathing life into it.
Without us, there isn't anythingat the idea stage, even at
the early operational stages.
Without us, itdoesn't do anything.
It's as if we're, we'reconstantly having to
give the business CPR.
Yeah.
And if we stop, we knowexactly what happens.
(07:07):
Yeah, yeah, exactly.
There comes a point at whichthat's no longer necessary, but
man, the muscle memory is builtat that point and we've wrapped
our entire being up in beingthe thing that keeps it alive.
That's just a matter of momentumand being able to recognize that
momentum going like, okay, itactually can survive without me.
But man, that's a, that'sa tough moment to spot.
Part of it too isit's all consuming.
(07:29):
There is no startup thatwon't just consume all of
you if you let it right.
It is endlessly hungry.
If IPO decide to spend 16hours straight today at my
computer, at my desk working.
The startup willconsume all of it.
The startup will never tellme, Hey, it's time to go home.
The startup will never tellme, Hey, you're pretty tired.
You should probablygo, go get some rest.
Right?
The startup will never tell me,you do, you know, you're, uh,
(07:50):
developing a terminal disease.
Yeah.
Because of this.
Right?
Like, yeah, n none ofthat will ever happen.
The startup will consume as muchas we give it, and that's where
the danger begins because westart to believe that because
it can consume all of ourtime, it should consume should.
All of our time.
Exactly that.
And it, it took me along time to start to
(08:13):
understand that balance.
Ryan, you said something, uh,earlier when we were talking
today about how you and Iboth hit the same kind of
milestone in starting families.
Yeah.
Where all of a suddensomething greater than
us became that voice.
What was it like for you?
Yeah, same thing.
You know, like I think you,you said something that ties
directly to this, which was,we have a high tolerance
for this kinda thing.
(08:34):
Like we have a high tolerancefor deferring happiness, for
deferring joy, for deferringtime on ourselves and just
accumulating maladies of,of physical and mental and
emotional states and, andforegoing relationships
doing all this other stuff.
But at some point when webecame partners to wives
and fathers to children.
All of a sudden I havefour other people's
tolerances to consider.
(08:55):
Are they as tolerant of myability to just sit at this
desk and pour myself into amonitor for 18, 19 hours a day?
The answer is no, they're notright at, at the point at which
I realized it was costing them.
And there are times wherelike yesterday, right?
Yesterday I took off at like twoin the afternoon my time for a
couple hours to go pick up mydaughters, take them to a soccer
(09:16):
match, watch them play, andthen I get them back to school.
And then I came back tothe house and continue
working at some points.
In the past, I think I stilldidn't really realize what
all the costs of that were.
Yeah.
I was like, you know, you, youthink about the fact that like.
I dunno, whether it's,whether you miss it or you
know, they're gonna miss it.
And whether that it's eitherguilt or just a fear of missing
out or a combination of thetwo kind of doesn't matter.
(09:37):
But over, over time, I'vestarted to pay more attention to
the fact that like it costs themsomething when I don't do that.
Right.
Right.
And so, right.
And you don't get it back.
You don't get it back.
You don't get it back.
Right.
And so I think being able tomake those trade-offs right,
and I think the, you know.
It's interesting, but you,you said something else that
ties directly to this, whichis that it's really hard
for us to see those things.
We will just continue to goand push and do, and we don't
(10:00):
necessarily notice in our ownlives what you had so that we
have to look outside, right?
Mm-hmm.
So whether it's your familyor not, or you call a friend
and find them floating in apool at two o'clock in the
afternoon, a Tuesday, the factthat we can't relate to someone
else enjoying their lives,just for the sake of that.
Probably ourproblem, not theirs.
Oh, absolutely.
Absolutely.
And again, and weneed those lenses.
(10:21):
Even while it was happening,you know, I, I said to my
friend, a again, he's knownme for a very long time, and
he is a good sounding board.
And I said, you know, I'mlaughing about this because
I know how ridiculous it isthat I have a problem with it.
And I said to him, I waslike, if it were me, I
would, I would be firingyou right now on the phone.
And I was like, but at the sametime, I also know you're right.
Right.
Yeah.
Which is, which is even harder.
And I think part of thisis getting to a point where
(10:44):
we stop and take stock ofwhat our values are, like
what's important to us.
Yeah.
Just like you said with yourdaughter and you say, these
are my non-negotiables.
Right?
These are the things thatif the startup takes these,
it's not okay anymore.
It's, it's not.
A lack of having thosethings really laid out.
Laid out in, in verybig, bold letters.
(11:07):
You and I have talked about thison previous episodes where we
sat down early in the process ofbuilding this company and said,
these are our non-negotiablesand to our what work with jerks.
Right.
We won't work jerks.
Right?
Yep.
And when we get to JerkyTown with someone, we're
like, you know, you'venever been worth it.
Never been worth it.
And every single time wewere like 10% sure that this
might be a good decision.
(11:27):
It was always a hundredpercent a good decision.
Yeah, right.
Hindsight it wasalways like, yep.
And the, the only thing we everquestioned was why not sooner?
Why not sooner?
Right.
And to be fair, those verysame people go home and they're
like, those guys are jerks.
By the way, they're also right.
Not 'cause I think we're jerks,Ryan, but because you know,
they look at it, especiallyif you're being let go as
(11:48):
how dare them, et cetera.
Right.
I was performing
even though I was a jerk.
Yeah, yeah.
So why would they, theyshould have tolerated it
again.
Again.
And so, and that's one of them.
Another one is, and you touchedon this, our ability to be able
to say, what's my commitmentto, let's say my family?
Mm-hmm.
At what point have I given toomuch or could I give too much?
(12:10):
Yeah, and the fact that youcan look at the soccer game
and say, Hey, I get that.
I could, I could avoid this.
I, I could not go andthe world wouldn't end.
However, this is also one ofthe things that draws the line,
that's to what my values are.
And if, if I don't go, andagain, it'd be different,
Ryan, if we were right inthe middle of closing some
major deal and there wassome make, or you're creating
(12:32):
a whole other consequence.
But fortunately we're not inthat position where we have
some kind of consequence.
But like I think for me, I havethis overarching consequence
of success, of responsibility.
You know, things likethat, that I can easily
let Trump, everything, thatexcuse can easily apply
to 16 hours of my day.
(12:53):
I have to forciblytalk myself out of that
excuse for every minute.
I don't spend with thatexcuse, if that makes sense.
Yeah.
Yeah.
No, it's, it's exactlythe same for me.
It's, it's the, the calculationis always in, in that order.
My default is be here for alot of hours and do as much
as I can or more than I can.
Yep.
And just keep doing, and youhave to talk yourself out of it.
(13:14):
I think where it cameabout, you talked about
some non-negotiables for me.
I've got a couple,like, one that's just
super personal is sleep.
I don't mess with it anymore.
Right.
I try not to.
My, my system's been messing,messing with itself for the
last couple weeks, but likeI try not to mess with sleep.
Sleep is so important 'causeI'm way better all day when
I have the right sleep.
The other one, and this issomething that I think I've
been doing a fairly good job offor a couple years now, but I
(13:36):
just read something a few weeksago that reinforced it from
a, a, a childhood psychologistthat said, your kids need you
on their time and their terms.
Right.
You can't say, oh, youwanna talk about that?
Well, I'm busy right now.
We'll talk about it later.
It doesn't work.
Right.
There's a real cost to themin so many ways because
the fact it was importantthen is why it's important.
And so I've really tried to dothat and just say like, look,
(13:58):
I can run to catch up on work.
I can, I'll bend my sleep.
Right?
Yeah.
If I have to, right?
I will sacrifice that personallyso that they're not forced to
sacrifice something at duringtheir, you know, important
years of personal development.
I've taken it a stepfurther where I've applied
it to my wife as well.
If she needs something,she gets it then.
Right?
My kids needsomething, they get it.
Then the way I analogize itto myself, 'cause for me the,
(14:20):
the going back to my earlysoccer days always helps.
And I said, you know what?
It's like having to runoutta position to cover
somebody else, right?
It's the right thingto do in the moment.
Now I know I'll have to runextra hard to get back to my
position to make sure that I'mnot letting somebody else down.
But if, if I gotta gocover somebody's spot.
I gotta get over there becausethe cost and the consequence
of that is immediate.
(14:41):
The cost and consequenceof me being out a position
is something that happenslater and I can do my
best to deal with it.
Right?
And I think that asstartup founders, we're
pretty good at being ableto run fast to catch up.
You know, something that's
really funny abouteverything we talk about
here is that none of it.
Is new.
Everything you're dealingwith right now has been done a
thousand times before you, whichmeans the answer already exists.
(15:03):
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 soundsfamiliar, stop guessing
about what to do, let us justgive you the answers to the
test and be done with it.
We, there is no pointwithin my work week, the
(15:25):
Monday through Friday.
Yeah.
Where I ever feel.
Like, I am justified fornot working and I'm not
comparing this to yours.
What, what I'm saying is it'sone of the things I spend a
lot of time thinking about.
Lemme give you some, somealso how I, I mitigate that.
One of the things I do, uh,and we've talked about this
in previous episodes, is I'mhyper specific about what
needs to get done today.
(15:46):
Because if I'm not, if I don'tsay, here's the one thing
that needs to get done today,I always start with one.
'cause if, if I don'tget one done, it doesn't
matter if I have two.
But here's the one thingI have to get done.
And let's say I, I motorthrough that went faster
than I expected it to andI got two and three done.
Cool.
Now I know that I can just keepadding more shit to the list.
That's just the nature.
The list never ends.
Right?
The only way I've beenable to kinda like quote
(16:08):
free myself from guilt isby accomplishing things.
If I knew I accomplishedsomething, it kind of
took some of the mental,like the guilt off me.
But if I think that I'm notaccomplishing something,
work could be gettingdone and I'm not doing it,
I'm not in a great place.
Right?
I'm just not.
No.
And I don't love that.
I think that the, the wayit's worked for me is that
(16:29):
I, instead of feeling likedown in guilt, it fires me up
to like be super productivewhen I get back to it.
Right?
Yeah, yeah, yeah.
And a lot of times, like whenI was driving to, to pick up
the kids yesterday, right?
It's a 15 minute drive overto where I had to grab 'em.
So on the way over thereI was doing voice notes
on the ad copy that I wasgonna write when I got back.
'cause that's what I paused.
To go do that.
(16:49):
Right?
I had some ads I wanted to getout and I said, all right, I'm
gonna go do this thing instead.
Spent that time,get myself fired up.
Okay?
So then when I get back,I've got, I've got the, the,
the core what I need, right?
And it's not like it's, we'renever really off, right?
It's so hard to completeswitch off car by myself.
I've got some time.
And so for me, what I've beentrying to do is just use that
as the motivation, right?
Mm-hmm.
That instead of letting thatfeeling just kind of like sour
(17:11):
within me, trying to use asa little bit of fuel to say,
okay, I'm gonna go do this.
I'm grateful that I can godo this thing with my kids.
I'm gonna use that gratitudeand the fact that I am a
little anxious about not beingat my desk to do this right
now, to, to, to elevate thework when I get back to it.
I think it's, I likethat seems to be working.
I also think that I, I, if welook at kind of the, the, the
(17:32):
ROI, if you will, that ourstartups provide for us, the
obvious one is profit, but the,the, the reason, that's a tough
one to, um, to always align to.
Is because most of uswon't get to a profitable
startup anytime soon.
Yeah.
Yeah.
So what ends up happening iswe're like, once we get to
profit, once we make a lot ofmoney, then we'll be happy.
And, you know, that's a,that's a bit of an elusive
(17:53):
goal, but let's, we'll savethat for another podcast.
But because the startup isperpetually not as successful
as we want it to be.
We always feel like allother costs or commitments
are justified until weget to that threshold.
Yeah.
Okay.
What we lose when we'reusing that kind of math that
like it just numeric dollarsign math, profit equals
(18:14):
success equals happiness.
Is that we can use that.
As an escape to make ourselvesmiserable along the way.
It's basic saying, Hey, we justkeep extending the finish line.
But the race is so gruelingand so awful that even if
we cross the finish line,it won't have mattered.
We'll be dead by then.
Yeah.
It's dangerous when wedon't see the other types
(18:35):
of ROI We need to beextracting from the startup.
For you, when, when youthink about those other
types of ROI, where wouldyou, and, and clearly like
we have to be performingwithin the startups, right?
It doesn't, doesn't workotherwise, but I think
the misnomer for me hasalways been that like there
were these points, right?
You set it like there'smilestones we hit where all of
a sudden then it'll be okay.
I've been in positionswhere I, I loved my revenue
(18:55):
numbers and I hated my life.
Right?
So it it isn'tnecessarily correlated.
Yeah.
There's also been times wherelike, I've loved my life.
Just made peace with the factthat revenue wasn't where I
wanted, but hating my lifeand, and designing a life that
I hated wasn't gonna help mehit revenue numbers, right.
Growth on paper means nothingif it's fueling misery, and
so we've gotta find somekind of balance from that.
But for you, what wouldbe the right after the,
(19:18):
the, the startup metrics,like what's the next one
that matters to you most?
I think part of it is working on
something that I care about.
Right.
Uh, uh, that's been probablymaybe the number one RO
i@startups.com for me, and,and I'm guessing maybe for
you I'll, I don't wannaput words in your mouth.
I love who I work for,being the, the startups
and I love the value of,of, of what we provide.
(19:39):
Now, to be fair, if I wantedto optimize just for income,
I'd probably go work ata public company, right.
And climb the ranksand, and be manager guy.
I would be miserable.
Right.
I'm sure of it.
I would be miserable,but I could make more
money doing that.
However, and this goes back tothe ROI, I wouldn't get any ROI.
I'd have more money in thebank, but be less happy.
(20:00):
And if money is, is a conduitpartially to happiness, right?
Then I would actually be shortcircuiting that because I'd
be getting the money, butnot any of the happiness.
And so when I look at startupsI've built in the past, not
that I didn't like them, butthey had no emotional ROI.
When I ran an ad agency,like the work was kind of
interesting, but I didn'tjump outta bed in the morning
(20:20):
and being like, I can'twait to help Best Buy, sell
more digital cameras, right?
I don't care.
Whereas with what we do, likelater on today, we're gonna
get on the phone, um, oh, I am.
I've got a bunch of office hourscalls with a bunch of founders,
and I'm gonna help them workthrough tons of problems and.
I love that.
And to be fair, theirgratitude is phenomenal, right?
(20:40):
They're like, man, Ididn't even see that.
Or, you helped me througha really tough time period.
Ryan, we get this.
A lot of people that thatlisten to the show, right?
Yeah.
Yeah.
A hundred percent.
Yeah.
We hear that kind offeedback all the time.
Uh, we get it fromour office hours.
Uh, I get the same thingfrom the workshops they
do on Mondays and Fridaysaround getting customers.
It just always feelsamazing, right?
And, and those kind of things.
Truly are, I think I saidthis a couple weeks ago
(21:01):
in, in the team Slack.
I was saying that like, thoseare the moments that pump me up.
Like I was headsdown and grinding.
I was, you know, trying to finda smoking gun around a problem
I was having within HubSpot,couldn't find it, and it was
driving me crazy and it couldhave completely changed my week.
And instead I was like, I getso fired up by those things
that we get to do, thoseinteractions that we have with
the, with the startup foundersthat at that point, like it
(21:22):
just, it fills you up, right?
And if your startup isconstantly leaving you
feeling hollow, then.
Any returns that you'regenerating as a result of that?
Kind of get couched aslosses in my book, man.
Because emotionalbankruptcy is a real thing.
Like it's a, it's a veryreal thing and I'd say that
it is almost always hand inhand with burnout for me.
Or maybe even the precursor.
Cause for the burnout,like you and I both have
(21:44):
incredible motors, wecan just keep working.
Right.
That's not the problem.
Right, right.
When, when the work nolonger rewards intrinsically,
not extrinsically, thenI think it starts to
fall really flat for me.
I agree.
I also think, and thisis, this is minor.
I don't think you and Ihave talked about this much,
but I think just the waywe've designed our business,
nothing to do with the,the, the industry we're or
anything else like that.
Yeah.
I mean, the actual businessthat we run, we are very
(22:07):
hands off with the team.
Right.
Uh, team has a phenomenallevel of autonomy and, and.
For me, that's a reflectionbecause I don't wanna be up
in people's business all day.
Right.
That brings me nopleasure whatsoever.
In fact, the more I have to doit, the more miserable I am.
But, but I think it's a flipside from a culture standpoint.
The folks that work withus enjoy a phenomenal
level of autonomy.
(22:28):
We also know theydon't always work.
Right?
There's some people thatlook at it as autonomy as
time in the pool, right?
I'm kidding.
But like, yeah.
And there's some people wholook at autonomy and say.
I can't wait to do greatwork and I'm gonna do
it on a schedule thatworks great for me.
And we have plenty of thosepeople here that can do that.
But what I'm saying is fromkind of how we've designed this
company and how it's evolved,I'm really proud of that.
(22:50):
You know, I'm really proudof, of that level of autonomy.
I'm really proud that we havea culture that supports that.
'cause Ryan, if we had adifferent version, okay,
where in our culture itwas all about hierarchy.
It was about 360 degree reviews.
It was about basically,uh, micromanagement,
et cetera, company.
I'm getting nauseous.
I wouldn't change the topic.
(23:10):
Yeah, yeah, yeah.
I wouldn't wannawork at that company.
Right.
Leadership.
Great.
Management, not so much.
Right?
Yeah.
It's just, it's the worst.
It's the worst.
There's a time anda place for it.
I totally respect it.
Yeah.
I'm not sayingmanagement is awful.
I'm saying I justdon't enjoy it.
Right?
Yeah.
I just don't enjoyit at that level.
I wanna work with peoplewho have autonomy.
I wanna work with peoplethat are self-motivated.
(23:32):
Again, that doesn't always work.
I would say more oftenthan not, it doesn't work.
As an example, this is, again,this is, we're tensioning
a little bit, but like wedon't do personnel reviews.
We've never done them.
There's been no360 degree review.
There's been nothing.
Right.
And my take on that,and again, this is all
about building somethingthat like works for you.
My take on that is if I can'tmanage the person day to day
(23:52):
with expectations and I haveto wait a year to tell them
they're not doing a good job,what the hell am I doing?
Right?
Yeah.
And, and if, if the person I'mworking with has no idea how
well they're doing, I'm like,I'm really bad at my job now.
I'm, uh, maybe it'sme just being lazy.
I found that the people whowork really well work just fine
in that, uh, that environmentand the people that don't.
(24:15):
Don't.
Yeah.
But my point is thosethings don't make me happy.
And so I've generallysaid, okay, let's build a
system that works for us.
We don't have todo those things.
And I think that's powerful.
It is.
And, and look, I thinkthose are some of the
best decisions we've made.
And you know, they don't showup directly on a p and l.
Clearly I think that they doimpact it, but they're not the
kind of things where it justshows directly on, on a PL.
(24:37):
But they keep us energized.
They keep us happy, theykeep us creative and and
that matters a lot, right?
You can't deposit happinessin a bank, I suppose, but
you can't buy your sanityback with money either.
So we gotta be carefulof what we're trading
at any given point.
You know?
Here's a differentway I'd phrase it.
Money makes me safe.
Yeah.
But the work I do and how Ispend my time makes me happy.
Can, can.
Yeah.
Yeah.
(24:57):
I'm saying, right?
Like, I think that's,
that's the important part
in this case.
It it, it does.
And, and let me build on that.
I've spent way too muchtime thinking about the
things that make me happy.
Uh, the activities that make mehappy, fun fact, they generally
don't cost anything, right?
The, the, the thingsthat I enjoy doing.
I enjoy playing hockey,enjoy playing t spend
time with my family.
I enjoy, uh, building stuff.
I, whatever.
They generally don't cost much.
(25:18):
I'm building a house now that,that does cost money, but
it, that's just incidental.
I could be working onanything else as a project.
Yeah.
You know?
Like that wouldn'tnecessarily have that
cost associated with it.
And so again, I look atmoney, not as if I have
more, my happiness is gonnago up, but if I have left,
my safety is gonna go down.
So I look at that as kindalike my baseline in the
formative years of my life.
Before I was an adult, I waspoor and I wasn't unhappy,
(25:41):
but I was very unsafe.
And I can tell you fromthat experience, it's very
hard to be consistentlyhappy while being unsafe.
Those two things there,there are a correlation,
they're different.
Yeah.
They're correlated, they'rediametrically opposed, right?
Like, I'd say it's, Iwouldn't say it's difficult.
It's, it's gotta benearly impossible.
If you're not safe,how can you be happy?
Conversely, though, if youare safe, you know you're
(26:02):
financially well off.
It also doesn'tguarantee happiness.
It doesn't work the other way.
It does not.
It's, uh, it's something Ialways say is money may not
buy you happiness, but you'rerarely happier without it.
I
think what it comes downto is figuring out what
that, like, what that actualthreshold for safety is.
Yeah.
Like at some point if you justkeep chasing more and more and
more and more safety, like whatare you building safety against?
(26:23):
Right.
You be, it's like thedifference between, you
know, having batteries ina flashlight, I. Building
a bunker in your backyard.
Right, right, right, right.
They're both derived somelevel of safety, and then
you gotta decide how muchsafety do I actually need?
I think that's where we, wecan get it wrong and maybe
we don't take our, our footoff the, the safety gas pedal
soon enough and start toapply some, some effort to
happiness because I. For years,we're, we're measuring our
(26:45):
success by how much discomfortwe can tolerate, right?
Like, I'm willing to behere and I'm gonna grind,
I'm gonna build, I'm gonnado, uh, and then we wonder
why we're desperate toexit a business, right?
Like, like you and I bothwere, uh, around the, the
early agencies where it's like,yeah, I don't wanna do this
anymore, please with my hands.
And so.
I think it comes down tojust picking that point and
saying like, this is safeenough, and now I can start
(27:06):
to focus on bringing somejoy into this equation,
but stick with that.
I think it's important for,at the very least, for us
to get like a milestone thatsays, Hey, the business isn't
where I want it to be yet.
That's usually the case.
Okay, I get that, but that'snot a perennial excuse for
me to allow it to make memiserable all the time.
Because if I agree that it'sokay for the business to make me
(27:28):
miserable, yeah, and this, thishas nothing to do with whether
you're willing to sacrifice.
There's always asacrifice to be had.
There's no deliberatestopping point in sacrifice.
This goes back to the businessbeing all consuming and for
decades, not even years.
For decades.
I didn't appreciatethat threshold.
I thought wrongly that therewas something on the other
side that would automaticallytell me I don't have to
(27:51):
behave like this anymore.
And there wasn't.
I mean, you know, one of thethings I, when I talk to people
who are substantially successfuland they have bigger enterprises
now, is they're like, I haveway more mouths to feed now.
Right.
Like, my problemsare much bigger now.
Yeah.
Like my pressure's goneway up and I'm like.
Damn.
Not only have you notgotten over the threshold,
you made it higher.
(28:11):
Right.
That's scary.
I think it goes back tosomething you said at the very
beginning, which is like thethe abusive relationship model
where then you just start tobuild on that and you just
continue to build more of thatabuse into what you're doing.
Right.
At some point, like I. Allyou're doing is creating
more obligation to grind.
Right.
Right.
And I think that one ofthe things for me, and, and
this speaks to the fact,like you said, we're, you
know, we built a team thatwe love, we love being with,
(28:32):
and we don't have to manage.
We, we've built clients thatwe love hanging out with.
Yeah.
And, and can driveamazing results for.
But I, I see so many foundersbuilding out of just.
Fear and obligation.
They're like, well, I'vemanaged to get it to this point.
Now I just have to keepdoing this because now
it's at least paying thebills or whatever it is.
Whatever the thingthat like Right.
Maintenance will keep,it will, will keep you
(28:52):
some level of safe.
Right.
I think if you ask most ofthose, if, if you took the
obligation out of it, theobligation to grind against this
thing, would you still do this?
Right.
And I feel like in alot of cases the answer
would've been no.
Like if I didn't feelobliged to grind towards
the end of the agency.
I would've stopped becauseI was not enjoying it.
I wasn't building anythingmeaningful anymore, and
I just didn't reallycare about the business.
(29:14):
And it sounds bad, but you'vesaid the same thing before.
I didn't really careabout the clients.
Well, not in the same waythat I care about some of
the folks that you and I knowwithin startups.com where
like, I legitimately carewhat happens to these people.
Like I want to know.
And I want you to feel goodabout it, but I think, you
know, if, if you're not, ifyou can't say, if I take the
obligation outta this, wouldI still grind in the same way?
You're probably buildingsomething you're gonna
(29:35):
resent at some point.
I
agree.
And what's interestingis how much of this is
from our own making?
This is, this is a littlebit out there, but, but
bear with me, I picturethis version of me.
Okay.
That's Edward Nortonin Fight Club Uhhuh.
And I've built this person thatI live with being my startup.
That's Tyler Durden, right?
Yeah.
Yeah.
That's constantly pushing meto get my ass kicked you on
(29:55):
to do things.
Yep.
Yep.
Right.
And at the end of themovie, I realize he's me.
Yeah.
Yeah, right.
Like it wasn'tactually a person.
I was the one whocreated all that.
Yeah.
And I think that's part ofwhat this is, is we can wake
up tomorrow and we can havethe version of our startup
company where we've got a happyrelationship, a non-abusive,
or we can continue to createthis fight club, Tyler Durden,
(30:18):
Brad Pitt, you know, archetypethat will constantly kick
our ass and have us feel likewe're a victim of this thing.
The difference in the two.
Is us, right?
That's the difference ofthe two, is our ability to
wake up tomorrow and say,to hell with this, right?
I, I'm not gonna live like this.
I'm not gonna create thisthing that was supposed to
(30:39):
be beautiful, but be becomesabusive and let that beat me.
The only way I'm ever, ever,ever going to be able to get
out of this trap is to wake uptomorrow and do it differently.
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
(31:00):
helping them win in thestartups.com community.
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 their episodeof the Startup Therapy Podcast.
This is Ryan Rutan,joined as always by my
friend, the founder,and CEO of startups.com.
Will, Schroeder will, we'vehad very, very interesting
relationships with our startups,with our work over the years.
It's necessarily whatI would call healthy.
We poured a lot of timeand love into them, and.
Sometimes they've given backto us, but I don't think we've
(00:21):
ever really truly demandedmuch back from our startups.
But that's not necessarilytrue for everybody else.
Right?
And so I think we gotta talkabout like the difference
between being a founderand and how to balance
some of that stuff out andkind of what it looks like
for the rest of the world.
For example, you evercalled a friend at two
o'clock in the afternoon,like Tuesday to find them
floating in a pool and just.
Found yourself incredulous.
I remember I told you thisstory after it happened.
(00:42):
This was like a year agoand I'm driving home.
Actually it's funny, I wasdriving home after teaching
the entrepreneurship class atmy, my kid's school and I was
calling a friend of mine 'causehe was kinda like on route
to where I was headed next.
And I was two o'clockon Tuesday, a beautiful
like summer, afternoonor spring afternoon and
I'm like, uh, hey man.
What you up to?
He's a senior executive at apublic, uh, technology company.
Right.
And he's a sales executive.
(01:02):
Right.
His whole life he has beenon the ground selling.
Right.
Like, he understands performancemetrics better than anybody.
Well, except when he is in thewater, uh, not selling well.
Okay.
So, so he's also oneof my oldest friends.
And, and so I was like, Heyman, what are you doing?
And he said, uh,I'm in the pool.
I'm like.
Huh?
Uh.
Like, what do you mean?
He, he is like, yeah,I'm sitting in a floaty,
(01:24):
floating in my pool.
I'm like, and this is, thisis what's so funny, Ryan.
I was like, how?
I was incredulous.
Yeah.
Like how could you Possibly attwo o'clock on a Tuesday, right?
When there's work to be done.
Yeah, there's work to be done.
Why depend on you,
sir.
And so my first thoughtwas to fire him.
(01:44):
My second thought was thatit doesn't work for me.
It doesn't work for me.
Yeah, I can't, I just go throwhim a cinder block in the pool.
But here's the best part.
Here's the best part, like,and again, I've got a great
relationship with, I'veknown him for a long time.
My response was kind oflike, I. How, like, how
could you possibly do that?
And, and this is all he said,he goes, makes me happy.
It makes me happy.
Like, and, and oh, just thanksfor making it worse right now.
(02:05):
Now I really don't understand.
Found.
I was like, that'sthe worst answer ever.
Right.
And, and again, I'm, I'mtelling this story to
set the premise here.
Of what a toxic relationshipwith work looks like.
And we're not talking about his,we're talking about mine, right?
Like it didn't occurto me like first blush.
Again, I'm, I'm not thatlike one dimensional, but
it didn't occur to me thatyou could just do that.
(02:27):
That you could just be sittingon a Tuesday in the middle
of the work week in your pool'cause it made you feel good.
I was like, there's gottabe some business purpose
to what's going on.
Right?
And that's whereour story begins.
We dig deep enough into it.
You can find that, right?
Like, I think as, asfounders, we often
conflate hustle with value.
And you know, we think if we'renot, if we're not chained to
our lap to 24 7, we're slackingand not the kind of slack
(02:49):
where we're, we're talkingto the rest of our team.
Not that slack, like justthe not doing anything
kind of slacking.
Guess what, like, productivitycan be floating in a pool at
2:00 PM if it recharges yourbrain, if it gives you the
energy you need to go back inand, and do the things right?
Like we know what the, the,the cost of burnout is.
This is the cost of thetherapy that keeps us from
getting there, I suppose.
Yeah.
And you know, one of thethings we do a lot of.
(03:11):
On this podcast, 300 episodes.
I mean, like, you know, we'vealmost, man, it's like 2
97 or eight or something.
Oh
damn.
I didn't realizeit was that close.
I just we're real close.
I rounded it up for charity.
When I think about, you know,all the topics we've covered,
and some folks know this becausesome folks that listen know us.
Most of what we talkabout here is a reflection
of our own journeys.
This is Ryan and I in ourown therapy, the startup
(03:33):
therapy we're generallytalking about Is ours ours?
So,
and a lot of peoplewill comment.
They'll say like, Hey, it justsounds like I'm in the middle
of a conversation of two people.
Like unpackingsomething between them.
It's 'cause you are, that'sactually what's happening.
Do you remember back like,this is 20 17, 18, somewhere
in there where we were like,we should do a podcast,
and then we were like.
(03:53):
What should we talk about?
And we went through allkinds of iterations, like
start up daily, we couldcover some news, we could
do all this different stuff.
And then finally we're like,you know, what about those
conversations we have everyweek anyways, where we're
just talking about like,what are you going through?
What are you going through?
How are you dealing with it?
What have you been through?
Yep.
And we're like, whatif we just hit record?
Yep.
And then we did.
And so here we are.
So to your point, it is verymuch just listening in on the
(04:15):
conversations of two people wholive through this stuff daily
in the ironies.
If you listen to this longand they're like, man, those
guys really need therapy,which is totally true.
Not anymore.
Yeah, yeah, exactly.
On a weekly basis.
I say this to, to set the tone,to say a lot of this isn't us
talking down to founders saying,here's what you're doing wrong.
This is in real time, sayingthis is what we're doing
wrong, like right now.
(04:37):
Right.
And the self-awareness of it,of being able to say, Hey,
you know, something's broken,doesn't make it go away.
I wanna start there.
For me, I'll just kindapoint to myself here.
I've spent the last 31 yearsin a very specific kind of
mindset, which is if I'mworking, I'm valuable And okay.
And if I'm not working,I'm guilty and not now
(04:59):
that is wildly unhealthy.
I just wanna be clear.
Right.
Wildly unhealthy pays well,but it's wildly unhealthy.
You said
this before, but it's,it's, it was fear.
Motivation.
Yep.
Right?
Yep.
And, and, and it'sabout safety, right?
Yep.
So for you, it's like,if I'm working, I don't
have to be afraid becauseit creates safety for me.
Right?
So as long as I'mworking, I'm safe.
Hundred percent.
Yeah.
I
mean that's, that'sa lot to deal with.
It is, right.
It's a, it's a hellof a lot to unpack.
(05:20):
I think what we buildup with that is a
tolerance for discomfort.
Oh yeah.
Right.
In, in so many ways.
So in the way my buddyis floating in a pool and
he's saying, Hey, I am notcomfortable at work right
this minute, I'm gonna godo something comfortable.
My res response to, tonot enough comfort is work
more because that willsomehow create more comfort.
(05:40):
And sometimes it does.
Right.
But I guess what I'msaying is if we zoom out.
As founders and we say,Hey, is my relationship
with my startup healthy?
Ergo Sure.
Does it pay me back inmore ways than cash?
As much as I put into it.
For everybody listening,
like I'd say 99% of youcan listen to this and me
just say, probably not.
(06:02):
Yeah.
There's gonna be a few of,you're like, no, I actually
have a very, very healthyrelationship with this.
Yeah.
Most of us don't.
For those of you that do,please create a podcast, Ryan,
and I would love to listen toit and take, I'd love to, can
follow along and do what you
do.
Yeah, just send me a notethat tells me I'm wrong.
That'd be great.
But for kind of everybody else,I think part of it is because
when we go into this, Ryan, likewhen we start something, you
start something from nothing.
(06:23):
It is, there's a voluminousamount of weight in
work and commitment,discomfort and frustration.
I think because we come toexpect that it builds a pattern
behavior where we just assume.
That's how it always has to be.
It's essentially starting in anabusive relationship and using
the abuse as the baseline forhow the relationship works.
(06:47):
That's how it
functions.
Yeah.
You know, I think, andagain, look, there's, there's
reasons for all this, right?
Part of it is that whenwe breathe life into
something new, that's it.
We're literallybreathing life into it.
Without us, there isn't anythingat the idea stage, even at
the early operational stages.
Without us, itdoesn't do anything.
It's as if we're, we'reconstantly having to
give the business CPR.
Yeah.
And if we stop, we knowexactly what happens.
(07:07):
Yeah, yeah, exactly.
There comes a point at whichthat's no longer necessary, but
man, the muscle memory is builtat that point and we've wrapped
our entire being up in beingthe thing that keeps it alive.
That's just a matter of momentumand being able to recognize that
momentum going like, okay, itactually can survive without me.
But man, that's a, that'sa tough moment to spot.
Part of it too isit's all consuming.
(07:29):
There is no startup thatwon't just consume all of
you if you let it right.
It is endlessly hungry.
If IPO decide to spend 16hours straight today at my
computer, at my desk working.
The startup willconsume all of it.
The startup will never tellme, Hey, it's time to go home.
The startup will never tellme, Hey, you're pretty tired.
You should probablygo, go get some rest.
Right?
The startup will never tell me,you do, you know, you're, uh,
(07:50):
developing a terminal disease.
Yeah.
Because of this.
Right?
Like, yeah, n none ofthat will ever happen.
The startup will consume as muchas we give it, and that's where
the danger begins because westart to believe that because
it can consume all of ourtime, it should consume should.
All of our time.
Exactly that.
And it, it took me along time to start to
(08:13):
understand that balance.
Ryan, you said something, uh,earlier when we were talking
today about how you and Iboth hit the same kind of
milestone in starting families.
Yeah.
Where all of a suddensomething greater than
us became that voice.
What was it like for you?
Yeah, same thing.
You know, like I think you,you said something that ties
directly to this, which was,we have a high tolerance
for this kinda thing.
(08:34):
Like we have a high tolerancefor deferring happiness, for
deferring joy, for deferringtime on ourselves and just
accumulating maladies of,of physical and mental and
emotional states and, andforegoing relationships
doing all this other stuff.
But at some point when webecame partners to wives
and fathers to children.
All of a sudden I havefour other people's
tolerances to consider.
(08:55):
Are they as tolerant of myability to just sit at this
desk and pour myself into amonitor for 18, 19 hours a day?
The answer is no, they're notright at, at the point at which
I realized it was costing them.
And there are times wherelike yesterday, right?
Yesterday I took off at like twoin the afternoon my time for a
couple hours to go pick up mydaughters, take them to a soccer
(09:16):
match, watch them play, andthen I get them back to school.
And then I came back tothe house and continue
working at some points.
In the past, I think I stilldidn't really realize what
all the costs of that were.
Yeah.
I was like, you know, you, youthink about the fact that like.
I dunno, whether it's,whether you miss it or you
know, they're gonna miss it.
And whether that it's eitherguilt or just a fear of missing
out or a combination of thetwo kind of doesn't matter.
(09:37):
But over, over time, I'vestarted to pay more attention to
the fact that like it costs themsomething when I don't do that.
Right.
Right.
And so, right.
And you don't get it back.
You don't get it back.
You don't get it back.
Right.
And so I think being able tomake those trade-offs right,
and I think the, you know.
It's interesting, but you,you said something else that
ties directly to this, whichis that it's really hard
for us to see those things.
We will just continue to goand push and do, and we don't
(10:00):
necessarily notice in our ownlives what you had so that we
have to look outside, right?
Mm-hmm.
So whether it's your familyor not, or you call a friend
and find them floating in apool at two o'clock in the
afternoon, a Tuesday, the factthat we can't relate to someone
else enjoying their lives,just for the sake of that.
Probably ourproblem, not theirs.
Oh, absolutely.
Absolutely.
And again, and weneed those lenses.
(10:21):
Even while it was happening,you know, I, I said to my
friend, a again, he's knownme for a very long time, and
he is a good sounding board.
And I said, you know, I'mlaughing about this because
I know how ridiculous it isthat I have a problem with it.
And I said to him, I waslike, if it were me, I
would, I would be firingyou right now on the phone.
And I was like, but at the sametime, I also know you're right.
Right.
Yeah.
Which is, which is even harder.
And I think part of thisis getting to a point where
(10:44):
we stop and take stock ofwhat our values are, like
what's important to us.
Yeah.
Just like you said with yourdaughter and you say, these
are my non-negotiables.
Right?
These are the things thatif the startup takes these,
it's not okay anymore.
It's, it's not.
A lack of having thosethings really laid out.
Laid out in, in verybig, bold letters.
(11:07):
You and I have talked about thison previous episodes where we
sat down early in the process ofbuilding this company and said,
these are our non-negotiablesand to our what work with jerks.
Right.
We won't work jerks.
Right?
Yep.
And when we get to JerkyTown with someone, we're
like, you know, you'venever been worth it.
Never been worth it.
And every single time wewere like 10% sure that this
might be a good decision.
(11:27):
It was always a hundredpercent a good decision.
Yeah, right.
Hindsight it wasalways like, yep.
And the, the only thing we everquestioned was why not sooner?
Why not sooner?
Right.
And to be fair, those verysame people go home and they're
like, those guys are jerks.
By the way, they're also right.
Not 'cause I think we're jerks,Ryan, but because you know,
they look at it, especiallyif you're being let go as
(11:48):
how dare them, et cetera.
Right.
I was performing
even though I was a jerk.
Yeah, yeah.
So why would they, theyshould have tolerated it
again.
Again.
And so, and that's one of them.
Another one is, and you touchedon this, our ability to be able
to say, what's my commitmentto, let's say my family?
Mm-hmm.
At what point have I given toomuch or could I give too much?
(12:10):
Yeah, and the fact that youcan look at the soccer game
and say, Hey, I get that.
I could, I could avoid this.
I, I could not go andthe world wouldn't end.
However, this is also one ofthe things that draws the line,
that's to what my values are.
And if, if I don't go, andagain, it'd be different,
Ryan, if we were right inthe middle of closing some
major deal and there wassome make, or you're creating
(12:32):
a whole other consequence.
But fortunately we're not inthat position where we have
some kind of consequence.
But like I think for me, I havethis overarching consequence
of success, of responsibility.
You know, things likethat, that I can easily
let Trump, everything, thatexcuse can easily apply
to 16 hours of my day.
(12:53):
I have to forciblytalk myself out of that
excuse for every minute.
I don't spend with thatexcuse, if that makes sense.
Yeah.
Yeah.
No, it's, it's exactlythe same for me.
It's, it's the, the calculationis always in, in that order.
My default is be here for alot of hours and do as much
as I can or more than I can.
Yep.
And just keep doing, and youhave to talk yourself out of it.
(13:14):
I think where it cameabout, you talked about
some non-negotiables for me.
I've got a couple,like, one that's just
super personal is sleep.
I don't mess with it anymore.
Right.
I try not to.
My, my system's been messing,messing with itself for the
last couple weeks, but likeI try not to mess with sleep.
Sleep is so important 'causeI'm way better all day when
I have the right sleep.
The other one, and this issomething that I think I've
been doing a fairly good job offor a couple years now, but I
(13:36):
just read something a few weeksago that reinforced it from
a, a, a childhood psychologistthat said, your kids need you
on their time and their terms.
Right.
You can't say, oh, youwanna talk about that?
Well, I'm busy right now.
We'll talk about it later.
It doesn't work.
Right.
There's a real cost to themin so many ways because
the fact it was importantthen is why it's important.
And so I've really tried to dothat and just say like, look,
(13:58):
I can run to catch up on work.
I can, I'll bend my sleep.
Right?
Yeah.
If I have to, right?
I will sacrifice that personallyso that they're not forced to
sacrifice something at duringtheir, you know, important
years of personal development.
I've taken it a stepfurther where I've applied
it to my wife as well.
If she needs something,she gets it then.
Right?
My kids needsomething, they get it.
Then the way I analogize itto myself, 'cause for me the,
(14:20):
the going back to my earlysoccer days always helps.
And I said, you know what?
It's like having to runoutta position to cover
somebody else, right?
It's the right thingto do in the moment.
Now I know I'll have to runextra hard to get back to my
position to make sure that I'mnot letting somebody else down.
But if, if I gotta gocover somebody's spot.
I gotta get over there becausethe cost and the consequence
of that is immediate.
(14:41):
The cost and consequenceof me being out a position
is something that happenslater and I can do my
best to deal with it.
Right?
And I think that asstartup founders, we're
pretty good at being ableto run fast to catch up.
You know, something that's
really funny abouteverything we talk about
here is that none of it.
Is new.
Everything you're dealingwith right now has been done a
thousand times before you, whichmeans the answer already exists.
(15:03):
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 soundsfamiliar, stop guessing
about what to do, let us justgive you the answers to the
test and be done with it.
We, there is no pointwithin my work week, the
(15:25):
Monday through Friday.
Yeah.
Where I ever feel.
Like, I am justified fornot working and I'm not
comparing this to yours.
What, what I'm saying is it'sone of the things I spend a
lot of time thinking about.
Lemme give you some, somealso how I, I mitigate that.
One of the things I do, uh,and we've talked about this
in previous episodes, is I'mhyper specific about what
needs to get done today.
(15:46):
Because if I'm not, if I don'tsay, here's the one thing
that needs to get done today,I always start with one.
'cause if, if I don'tget one done, it doesn't
matter if I have two.
But here's the one thingI have to get done.
And let's say I, I motorthrough that went faster
than I expected it to andI got two and three done.
Cool.
Now I know that I can just keepadding more shit to the list.
That's just the nature.
The list never ends.
Right?
The only way I've beenable to kinda like quote
(16:08):
free myself from guilt isby accomplishing things.
If I knew I accomplishedsomething, it kind of
took some of the mental,like the guilt off me.
But if I think that I'm notaccomplishing something,
work could be gettingdone and I'm not doing it,
I'm not in a great place.
Right?
I'm just not.
No.
And I don't love that.
I think that the, the wayit's worked for me is that
(16:29):
I, instead of feeling likedown in guilt, it fires me up
to like be super productivewhen I get back to it.
Right?
Yeah, yeah, yeah.
And a lot of times, like whenI was driving to, to pick up
the kids yesterday, right?
It's a 15 minute drive overto where I had to grab 'em.
So on the way over thereI was doing voice notes
on the ad copy that I wasgonna write when I got back.
'cause that's what I paused.
To go do that.
(16:49):
Right?
I had some ads I wanted to getout and I said, all right, I'm
gonna go do this thing instead.
Spent that time,get myself fired up.
Okay?
So then when I get back,I've got, I've got the, the,
the core what I need, right?
And it's not like it's, we'renever really off, right?
It's so hard to completeswitch off car by myself.
I've got some time.
And so for me, what I've beentrying to do is just use that
as the motivation, right?
Mm-hmm.
That instead of letting thatfeeling just kind of like sour
(17:11):
within me, trying to use asa little bit of fuel to say,
okay, I'm gonna go do this.
I'm grateful that I can godo this thing with my kids.
I'm gonna use that gratitudeand the fact that I am a
little anxious about not beingat my desk to do this right
now, to, to, to elevate thework when I get back to it.
I think it's, I likethat seems to be working.
I also think that I, I, if welook at kind of the, the, the
(17:32):
ROI, if you will, that ourstartups provide for us, the
obvious one is profit, but the,the, the reason, that's a tough
one to, um, to always align to.
Is because most of uswon't get to a profitable
startup anytime soon.
Yeah.
Yeah.
So what ends up happening iswe're like, once we get to
profit, once we make a lot ofmoney, then we'll be happy.
And, you know, that's a,that's a bit of an elusive
(17:53):
goal, but let's, we'll savethat for another podcast.
But because the startup isperpetually not as successful
as we want it to be.
We always feel like allother costs or commitments
are justified until weget to that threshold.
Yeah.
Okay.
What we lose when we'reusing that kind of math that
like it just numeric dollarsign math, profit equals
(18:14):
success equals happiness.
Is that we can use that.
As an escape to make ourselvesmiserable along the way.
It's basic saying, Hey, we justkeep extending the finish line.
But the race is so gruelingand so awful that even if
we cross the finish line,it won't have mattered.
We'll be dead by then.
Yeah.
It's dangerous when wedon't see the other types
(18:35):
of ROI We need to beextracting from the startup.
For you, when, when youthink about those other
types of ROI, where wouldyou, and, and clearly like
we have to be performingwithin the startups, right?
It doesn't, doesn't workotherwise, but I think
the misnomer for me hasalways been that like there
were these points, right?
You set it like there'smilestones we hit where all of
a sudden then it'll be okay.
I've been in positionswhere I, I loved my revenue
(18:55):
numbers and I hated my life.
Right?
So it it isn'tnecessarily correlated.
Yeah.
There's also been times wherelike, I've loved my life.
Just made peace with the factthat revenue wasn't where I
wanted, but hating my lifeand, and designing a life that
I hated wasn't gonna help mehit revenue numbers, right.
Growth on paper means nothingif it's fueling misery, and
so we've gotta find somekind of balance from that.
But for you, what wouldbe the right after the,
(19:18):
the, the startup metrics,like what's the next one
that matters to you most?
I think part of it is working on
something that I care about.
Right.
Uh, uh, that's been probablymaybe the number one RO
i@startups.com for me, and,and I'm guessing maybe for
you I'll, I don't wannaput words in your mouth.
I love who I work for,being the, the startups
and I love the value of,of, of what we provide.
(19:39):
Now, to be fair, if I wantedto optimize just for income,
I'd probably go work ata public company, right.
And climb the ranksand, and be manager guy.
I would be miserable.
Right.
I'm sure of it.
I would be miserable,but I could make more
money doing that.
However, and this goes back tothe ROI, I wouldn't get any ROI.
I'd have more money in thebank, but be less happy.
(20:00):
And if money is, is a conduitpartially to happiness, right?
Then I would actually be shortcircuiting that because I'd
be getting the money, butnot any of the happiness.
And so when I look at startupsI've built in the past, not
that I didn't like them, butthey had no emotional ROI.
When I ran an ad agency,like the work was kind of
interesting, but I didn'tjump outta bed in the morning
(20:20):
and being like, I can'twait to help Best Buy, sell
more digital cameras, right?
I don't care.
Whereas with what we do, likelater on today, we're gonna
get on the phone, um, oh, I am.
I've got a bunch of office hourscalls with a bunch of founders,
and I'm gonna help them workthrough tons of problems and.
I love that.
And to be fair, theirgratitude is phenomenal, right?
(20:40):
They're like, man, Ididn't even see that.
Or, you helped me througha really tough time period.
Ryan, we get this.
A lot of people that thatlisten to the show, right?
Yeah.
Yeah.
A hundred percent.
Yeah.
We hear that kind offeedback all the time.
Uh, we get it fromour office hours.
Uh, I get the same thingfrom the workshops they
do on Mondays and Fridaysaround getting customers.
It just always feelsamazing, right?
And, and those kind of things.
Truly are, I think I saidthis a couple weeks ago
(21:01):
in, in the team Slack.
I was saying that like, thoseare the moments that pump me up.
Like I was headsdown and grinding.
I was, you know, trying to finda smoking gun around a problem
I was having within HubSpot,couldn't find it, and it was
driving me crazy and it couldhave completely changed my week.
And instead I was like, I getso fired up by those things
that we get to do, thoseinteractions that we have with
the, with the startup foundersthat at that point, like it
(21:22):
just, it fills you up, right?
And if your startup isconstantly leaving you
feeling hollow, then.
Any returns that you'regenerating as a result of that?
Kind of get couched aslosses in my book, man.
Because emotionalbankruptcy is a real thing.
Like it's a, it's a veryreal thing and I'd say that
it is almost always hand inhand with burnout for me.
Or maybe even the precursor.
Cause for the burnout,like you and I both have
(21:44):
incredible motors, wecan just keep working.
Right.
That's not the problem.
Right, right.
When, when the work nolonger rewards intrinsically,
not extrinsically, thenI think it starts to
fall really flat for me.
I agree.
I also think, and thisis, this is minor.
I don't think you and Ihave talked about this much,
but I think just the waywe've designed our business,
nothing to do with the,the, the industry we're or
anything else like that.
Yeah.
I mean, the actual businessthat we run, we are very
(22:07):
hands off with the team.
Right.
Uh, team has a phenomenallevel of autonomy and, and.
For me, that's a reflectionbecause I don't wanna be up
in people's business all day.
Right.
That brings me nopleasure whatsoever.
In fact, the more I have to doit, the more miserable I am.
But, but I think it's a flipside from a culture standpoint.
The folks that work withus enjoy a phenomenal
level of autonomy.
(22:28):
We also know theydon't always work.
Right?
There's some people thatlook at it as autonomy as
time in the pool, right?
I'm kidding.
But like, yeah.
And there's some people wholook at autonomy and say.
I can't wait to do greatwork and I'm gonna do
it on a schedule thatworks great for me.
And we have plenty of thosepeople here that can do that.
But what I'm saying is fromkind of how we've designed this
company and how it's evolved,I'm really proud of that.
(22:50):
You know, I'm really proudof, of that level of autonomy.
I'm really proud that we havea culture that supports that.
'cause Ryan, if we had adifferent version, okay,
where in our culture itwas all about hierarchy.
It was about 360 degree reviews.
It was about basically,uh, micromanagement,
et cetera, company.
I'm getting nauseous.
I wouldn't change the topic.
(23:10):
Yeah, yeah, yeah.
I wouldn't wannawork at that company.
Right.
Leadership.
Great.
Management, not so much.
Right?
Yeah.
It's just, it's the worst.
It's the worst.
There's a time anda place for it.
I totally respect it.
Yeah.
I'm not sayingmanagement is awful.
I'm saying I justdon't enjoy it.
Right?
Yeah.
I just don't enjoyit at that level.
I wanna work with peoplewho have autonomy.
I wanna work with peoplethat are self-motivated.
(23:32):
Again, that doesn't always work.
I would say more oftenthan not, it doesn't work.
As an example, this is, again,this is, we're tensioning
a little bit, but like wedon't do personnel reviews.
We've never done them.
There's been no360 degree review.
There's been nothing.
Right.
And my take on that,and again, this is all
about building somethingthat like works for you.
My take on that is if I can'tmanage the person day to day
(23:52):
with expectations and I haveto wait a year to tell them
they're not doing a good job,what the hell am I doing?
Right?
Yeah.
And, and if, if the person I'mworking with has no idea how
well they're doing, I'm like,I'm really bad at my job now.
I'm, uh, maybe it'sme just being lazy.
I found that the people whowork really well work just fine
in that, uh, that environmentand the people that don't.
(24:15):
Don't.
Yeah.
But my point is thosethings don't make me happy.
And so I've generallysaid, okay, let's build a
system that works for us.
We don't have todo those things.
And I think that's powerful.
It is.
And, and look, I thinkthose are some of the
best decisions we've made.
And you know, they don't showup directly on a p and l.
Clearly I think that they doimpact it, but they're not the
kind of things where it justshows directly on, on a PL.
(24:37):
But they keep us energized.
They keep us happy, theykeep us creative and and
that matters a lot, right?
You can't deposit happinessin a bank, I suppose, but
you can't buy your sanityback with money either.
So we gotta be carefulof what we're trading
at any given point.
You know?
Here's a differentway I'd phrase it.
Money makes me safe.
Yeah.
But the work I do and how Ispend my time makes me happy.
Can, can.
Yeah.
Yeah.
(24:57):
I'm saying, right?
Like, I think that's,
that's the important part
in this case.
It it, it does.
And, and let me build on that.
I've spent way too muchtime thinking about the
things that make me happy.
Uh, the activities that make mehappy, fun fact, they generally
don't cost anything, right?
The, the, the thingsthat I enjoy doing.
I enjoy playing hockey,enjoy playing t spend
time with my family.
I enjoy, uh, building stuff.
I, whatever.
They generally don't cost much.
(25:18):
I'm building a house now that,that does cost money, but
it, that's just incidental.
I could be working onanything else as a project.
Yeah.
You know?
Like that wouldn'tnecessarily have that
cost associated with it.
And so again, I look atmoney, not as if I have
more, my happiness is gonnago up, but if I have left,
my safety is gonna go down.
So I look at that as kindalike my baseline in the
formative years of my life.
Before I was an adult, I waspoor and I wasn't unhappy,
(25:41):
but I was very unsafe.
And I can tell you fromthat experience, it's very
hard to be consistentlyhappy while being unsafe.
Those two things there,there are a correlation,
they're different.
Yeah.
They're correlated, they'rediametrically opposed, right?
Like, I'd say it's, Iwouldn't say it's difficult.
It's, it's gotta benearly impossible.
If you're not safe,how can you be happy?
Conversely, though, if youare safe, you know you're
(26:02):
financially well off.
It also doesn'tguarantee happiness.
It doesn't work the other way.
It does not.
It's, uh, it's something Ialways say is money may not
buy you happiness, but you'rerarely happier without it.
I
think what it comes downto is figuring out what
that, like, what that actualthreshold for safety is.
Yeah.
Like at some point if you justkeep chasing more and more and
more and more safety, like whatare you building safety against?
(26:23):
Right.
You be, it's like thedifference between, you
know, having batteries ina flashlight, I. Building
a bunker in your backyard.
Right, right, right, right.
They're both derived somelevel of safety, and then
you gotta decide how muchsafety do I actually need?
I think that's where we, wecan get it wrong and maybe
we don't take our, our footoff the, the safety gas pedal
soon enough and start toapply some, some effort to
happiness because I. For years,we're, we're measuring our
(26:45):
success by how much discomfortwe can tolerate, right?
Like, I'm willing to behere and I'm gonna grind,
I'm gonna build, I'm gonnado, uh, and then we wonder
why we're desperate toexit a business, right?
Like, like you and I bothwere, uh, around the, the
early agencies where it's like,yeah, I don't wanna do this
anymore, please with my hands.
And so.
I think it comes down tojust picking that point and
saying like, this is safeenough, and now I can start
(27:06):
to focus on bringing somejoy into this equation,
but stick with that.
I think it's important for,at the very least, for us
to get like a milestone thatsays, Hey, the business isn't
where I want it to be yet.
That's usually the case.
Okay, I get that, but that'snot a perennial excuse for
me to allow it to make memiserable all the time.
Because if I agree that it'sokay for the business to make me
(27:28):
miserable, yeah, and this, thishas nothing to do with whether
you're willing to sacrifice.
There's always asacrifice to be had.
There's no deliberatestopping point in sacrifice.
This goes back to the businessbeing all consuming and for
decades, not even years.
For decades.
I didn't appreciatethat threshold.
I thought wrongly that therewas something on the other
side that would automaticallytell me I don't have to
(27:51):
behave like this anymore.
And there wasn't.
I mean, you know, one of thethings I, when I talk to people
who are substantially successfuland they have bigger enterprises
now, is they're like, I haveway more mouths to feed now.
Right.
Like, my problemsare much bigger now.
Yeah.
Like my pressure's goneway up and I'm like.
Damn.
Not only have you notgotten over the threshold,
you made it higher.
(28:11):
Right.
That's scary.
I think it goes back tosomething you said at the very
beginning, which is like thethe abusive relationship model
where then you just start tobuild on that and you just
continue to build more of thatabuse into what you're doing.
Right.
At some point, like I. Allyou're doing is creating
more obligation to grind.
Right.
Right.
And I think that one ofthe things for me, and, and
this speaks to the fact,like you said, we're, you
know, we built a team thatwe love, we love being with,
(28:32):
and we don't have to manage.
We, we've built clients thatwe love hanging out with.
Yeah.
And, and can driveamazing results for.
But I, I see so many foundersbuilding out of just.
Fear and obligation.
They're like, well, I'vemanaged to get it to this point.
Now I just have to keepdoing this because now
it's at least paying thebills or whatever it is.
Whatever the thingthat like Right.
Maintenance will keep,it will, will keep you
(28:52):
some level of safe.
Right.
I think if you ask most ofthose, if, if you took the
obligation out of it, theobligation to grind against this
thing, would you still do this?
Right.
And I feel like in alot of cases the answer
would've been no.
Like if I didn't feelobliged to grind towards
the end of the agency.
I would've stopped becauseI was not enjoying it.
I wasn't building anythingmeaningful anymore, and
I just didn't reallycare about the business.
(29:14):
And it sounds bad, but you'vesaid the same thing before.
I didn't really careabout the clients.
Well, not in the same waythat I care about some of
the folks that you and I knowwithin startups.com where
like, I legitimately carewhat happens to these people.
Like I want to know.
And I want you to feel goodabout it, but I think, you
know, if, if you're not, ifyou can't say, if I take the
obligation outta this, wouldI still grind in the same way?
You're probably buildingsomething you're gonna
(29:35):
resent at some point.
I
agree.
And what's interestingis how much of this is
from our own making?
This is, this is a littlebit out there, but, but
bear with me, I picturethis version of me.
Okay.
That's Edward Nortonin Fight Club Uhhuh.
And I've built this person thatI live with being my startup.
That's Tyler Durden, right?
Yeah.
Yeah.
That's constantly pushing meto get my ass kicked you on
(29:55):
to do things.
Yep.
Yep.
Right.
And at the end of themovie, I realize he's me.
Yeah.
Yeah, right.
Like it wasn'tactually a person.
I was the one whocreated all that.
Yeah.
And I think that's part ofwhat this is, is we can wake
up tomorrow and we can havethe version of our startup
company where we've got a happyrelationship, a non-abusive,
or we can continue to createthis fight club, Tyler Durden,
(30:18):
Brad Pitt, you know, archetypethat will constantly kick
our ass and have us feel likewe're a victim of this thing.
The difference in the two.
Is us, right?
That's the difference ofthe two, is our ability to
wake up tomorrow and say,to hell with this, right?
I, I'm not gonna live like this.
I'm not gonna create thisthing that was supposed to
(30:39):
be beautiful, but be becomesabusive and let that beat me.
The only way I'm ever, ever,ever going to be able to get
out of this trap is to wake uptomorrow and do it differently.
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
(31:00):
helping them win in thestartups.com community.
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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The official podcast of comedian Joe Rogan.
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Current and classic episodes, featuring compelling true-crime mysteries, powerful documentaries and in-depth investigations. Special Summer Offer: Exclusively on Apple Podcasts, try our Dateline Premium subscription completely free for one month! With Dateline Premium, you get every episode ad-free plus exclusive bonus content.