May 10, 2025 • 25 mins
In this episode of the Startup Therapy Podcast,Ryan and Will delve into the emotional journey of startup founders who feel out of place in the very companies they built from scratch. They discuss the guilt and struggle founders experience when their roles change and they no longer enjoy their jobs. They share personal anecdotes and examine the impact of forced roles, from management misfits to a loss of personal fulfillment. The duo also explores the concept of evolving with or beyond your startup, and how to come to terms with these difficult but often necessary transitions.
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:
00:48 The Shift from Building to Managing
01:29 The Struggles of Management
02:13 The Evolution of Roles
04:17 The Peter Principle in Action
05:29 The Emotional Toll of Management
08:34 Reflecting on the Past and Moving Forward
09:57 The Realization and Acceptance
12:39 The Dilemma of Founder Evolution
13:10 Learning from the Past
13:42 Commitment and Introspection
15:02 The Cost of Doing What You Hate
17:40 Recognizing and Embracing Change
20:16 The Hard Decision to Move On
25:03 Celebrating Growth and Moving Forward
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 joint,as always by my friend, the
founder, and CO of startups.com.
Will Schroeder will haveyou ever walked into
something that you've builtentirely from scratch?
Ground up, zero to one moment.
Then wandered through thedoors and just felt like
you no longer belong there.
(00:20):
A lot.
There was not like manytimes, but like, like an
overwhelming feeling of that.
Early in my career, uh, whenI was building a company,
companies started gettingbig, like real big as it's
getting bigger, you know,I'm still young at time.
I'm like 26 as it'sgetting bigger.
I'm sitting there going.
Okay.
Well, you know, I used tobuild websites that was,
you know, part, part ofwhat we did as an agency.
(00:41):
And I, yeah.
I don't really doany code anymore.
And now I don't doany design anymore.
Yeah.
And now I don't really dothe, the strategy anymore.
And one day I walk in andI'm like, what do I do here?
Right.
Yeah.
Like, I'm managing, I'm, I'mhaving meetings about meetings.
I don't produce a goddamn thing.
Yeah.
And it was miserable.
Yeah.
Miserable.
Right.
It's funny, ma'am,you just described it.
(01:02):
I had the samething happen to me.
I've seen this happen withcountless founders where
it's like one day you justwalk in, it's as if you
walk into a glass wall.
It felt that way to me.
It was like, it was such asudden sort of thing where
it's like I was the lastone to kind of know that the
company had had moved on andthat I no longer fit there.
And it, it felt likesuch a betrayal of
everything I'd built.
(01:22):
I'm like.
This is only all herebecause of me, but now
I don't need to be here.
Like, what the
f Like I
didn't know how to deal with it.
Let me tee that up a bit.
So a lot of times what'llhappen is, you know, you and
I'll talk to founders andyou can tell that like they
appreciate what they've built.
Yeah.
But they don't liketheir job anymore.
Yeah, yeah.
Oh, a hundred percent.
And,
and I guarantee we've got afair amount of people that are
(01:43):
listening to this, this episodebe like, yeah, that's me.
And but here's the problem.
We feel guilty about it.
We feel guilty.
That we don't like the jobbecause it makes us ungrateful.
I walk in and I remember atthe time, you know, we just
built these two new a hundredthousand square foot buildings.
We had, you know, six or 700people at the time, and I'm
like, I should be so proudof what we have here, and I
(02:03):
am, and I don't like my job.
And, and this isn't me beinglike, entitled, I just didn't
like what I was doing anymore.
Like, there's nothingwrong with that.
I, but.
Definitely didn't know that.
It's funny, we go throughsome of those things at the
early stages too, right?
Where it's like there are lotsof jobs that have to be done.
As a startup founder,you're doing it all right?
It's chef cook,bottle washer, right?
You're doing it all.
And we're sort of used to it atthat phase, but I think we get
(02:24):
into like where we start to hitour stride and our superpower,
the company starts to growbased on that, and then all of
a sudden that goes away again.
And you're like, butnow what I'm doing?
Isn't what I like to be doing.
I, I know I've shared thiswith you before, but there
was a point at which I wasrunning my agency, you know,
back in the dark ages and ithad been like a two week period
when I was looking back atlike my, my daily journals.
It'd been like a two week periodwhere I had done absolutely
(02:47):
nothing but keep the three mostimportant teams in the business
from fighting with each other.
I had just become like,I was just dad and I was
unprepared to be a father.
At that point, I was right.
20 at this point.
21,
yeah.
And look, and, andsome people love it.
Some people like that'swhat they wanna do.
Like I remember, I rememberwhen I was growing up and
I was reading about likesuperstar CEOs, right?
(03:09):
The Jack Welch era, right?
Where it was like youwere prided on being
an employee, right?
Like now it's all, if you'renot the founder, no one cares.
Right.
But that was a different erawhere like it, you were the
silver-haired 60-year-oldthat finally made it to the,
the corner office type thing.
Yeah.
Climbed your way from,yeah, from nowhere to you.
I It
was all about the, acareer trajectory, right?
(03:30):
Yeah.
Like that all got turned onits head in the startup world
where you're like 23 in theCE and you kind of started
backward, but not too long ago,or maybe it was a long time
ago, and I'm just getting old.
Not too long ago, it was allabout moving up to the C-suite.
Those people werecareer managers.
Like the way you got there,like, here's the thing,
you couldn't have possiblybeen prior to that, right?
(03:51):
You couldn't have possiblybeen Mark Zuckerberg
and you just coded yourway to the top, right?
Like you coded and youwound up at the top 'cause
you started at the top.
And so it fascinates methat like in this, in
kinda this new world.
These folks that came in aslike the really talented coder,
let's say just as an example,wake up one day and they're
(04:11):
like, I'm a manager now.
Like, what thehell just happened?
It's thrust on you.
It's thrust on you.
Yeah.
I mean that's the, the, goingback to management philosophy
from that same period oftime, that's when the Peter
principle was born, right?
Where you get promotedup to your highest
level of inefficiency.
You're, you are agreat junior coder.
We'll make you a,a senior coder.
You're a great senior coder.
We'll make you a, whateverthe next level of that is.
Then you become a directorof technology or something
(04:34):
where now you're nolonger coding, you're
managing the other coders.
'cause you were a great coder.
Turns out you've nevermanaged anybody before.
I watched that happen.
Right, because as we werescaling you, as we were
adding more and more people,same exact thing you said.
Yeah.
Specifically.
I remember one of our, oursenior developers kept getting
promoted Uhhuh, and when Isay kept getting promoted, it
didn't happen outta nowhere.
I was promoting, but as I waswatching it happen, I saw him
(04:56):
get more and more uncomfortable.
Mm-hmm.
Good, smart guy, right?
Yep.
I could tell he was gettingmoved to the top of the ranks
only because he had the seniormost technical knowledge.
Yeah.
Right.
Like he was more technicalthan anyone else.
But as a manager, like he,he wasn't gifted in any way.
Yeah, right.
(05:16):
To your point, he justkept getting pushed there.
The irony was the guy pushinghim was having the same
exact problem, which was me.
Right.
I was like, maybeyou just wanted
company for the misery.
Like,
yeah, yeah, Igotta make sure I'm
not alone in this misery.
So we get to this point wherelike the company that we
built right, was built forwho we were, not who we are.
(05:36):
And I think that's ahard thing for us to
step back and say, huh.
And I think for a lotof reasons, one of
them for me was that.
When I realized I was doingmanagement, and you've drawn
this distinction before too,which is the difference between
management and leadership.
I'm not even gonna goas far as as leadership.
It wasn't that I was likethere were points where I was
leading the company versusversus managing these people.
(05:58):
My own individual abilityto produce felt taken away.
And so for me, right.
That feeling that was the mostoverwhelming, like the literal,
like choking out my oxygenanxiety level, like worrying
about this stuff was when itwould feel like because I had
to manage people, I couldn'tgo do things that I found more
important, more engaging, moreexciting, more valuable, right?
(06:21):
Like whether that was going andtrying to land a new client,
whether that was figuring outa new way to deliver something,
whether that was figuring outwhether we should move from,
you know, move to cold fusion,whatever it was, you know, a
hundred thousand years ago in.
So, you know, like that tome was a big part of it.
And so I think fold.
Like I also wasn't atalented manager by any
stretch of the imagination.
I was not right.
(06:41):
I, I'd had no experience.
I had never even reallybeen managed because
I was so damn young.
I'd never had a real, real job.
And so part of it was.
Absolutely a lack of skill and,and probably a rightful amount
of fear against management.
Sure, sure.
Because I didn't knowwhat I was doing.
But the other part of itwas it, like it took the
fun away from me even hadI been a talented manager.
It's sort of like this, Ilook at it this way, if you're
Christiana Ronaldo, and he'sgetting old now, so we may be
(07:04):
getting close to this point,but let's say Christiana
Ronaldo from, from five yearsago, six years ago, prime peak
performance, and all of a suddenyou're like, you know what?
This guy's the bestplayer in the world.
We should make him a coachso we can have a bunch
more really great players.
Hold aside that he may noteven be a good manager.
Do you think that guy wantsto be watching the game?
That's how I felt every singletime I was managing people felt
(07:26):
like I'm watching the game andhaving to coach them through it.
I'm like, I want togo kick the damn ball.
I don't wanna be off the field.
Painful, super painful.
I was like, in short order.
I was like, man, I missed thedays when we'd all stay up
all night, like working on aproject and just crushing it.
Yes.
And and now it's like, yeah,no one wants to do that.
No.
Right.
Like the only reason we did thatis 'cause you, you did it right.
(07:47):
Like, you know, youpushed us to that end.
I don't know ifyou'll remember this.
There was a point at whichyou remember when we.
We were refinishingthe upper floors in the
offices on Manning, right?
Mm-hmm.
And we had to moveeverybody to the basement.
You remember that?
Where everybody wentto the basement for a
little bit and like wewere down there basement.
It was a war zone.
We had video gamemachines down there.
We had weight racks.
We had desks piledon top of each other.
(08:09):
Yep.
And on two or three occasionsI tried to rally, like,
let's pull an all-nighterand get this done.
Let's bang throughthese clients, whatever.
And it was like, I waslike, yeah, I felt like,
who was the politicianthat did that awful yell.
Do you remember that?
Scream heard aroundthe world where he was.
Anyways, there was noanswer to my rally cry.
I was like, let's do it.
And everybody else is like,um, uh, time for drinks or
(08:31):
whatever, and they're pew gone.
Right.
Such a bad feeling.
I think it's hard for us,uh, you know, as the founders
to take stock in that.
Yeah.
And to be able to say, ah, okay.
The good old days.
We're, we're only good for me.
Right.
Or said differently.
Like, you know, there's alwayspeople like, oh my God, I
remember when the companywas smaller and we all hung
out and blah, blah, blah.
And that's great.
Yeah.
But it's also, you have totake stock and recognize
(08:53):
that like, that's over.
It's the guy who keepstalking about that one
party from college, andyou're like, no, I get it.
I, I get it.
It was fun.
That was 20 years ago.
You were great.
Yeah,
but I get it right.
Uh, like that part of islong since over, and I think
as managers, as founders,we, we get into this spot
where we long for those days.
And what's so hard is we'rethe one in control of where
(09:15):
this company is gone, but thecompany evolves beyond us.
Yeah.
That's what this is all about.
The company evolves beyond us.
It's one thing when it evolves,evolves beyond everybody else.
It's really hard whenit evolves beyond us.
So the question becomes.
Do we wanna grow with it?
Do we wanna change?
It's hard, and I think thisis, it's, it's a question that
it can be really difficultto answer at that point.
(09:38):
The point where youhave to answer it.
Because you might notbe well armed for it.
Right.
You're, you're nowrealizing that there's
a new, new world order.
I have to have adifferent set of skills.
I have to have a different set.
Yep.
And, and so you're,you're simultaneously
asked, being asked, doyou want to do this thing?
Are you capable of doing this?
You know, even if you sayyou want to, can you do it?
We've seen this happen too,like sometimes companies
(09:58):
legitimately outgrow thefounder or we see it outgrow
one of the founding members.
I, I think you and I haveused the example before where
like, your best buddy fromuniversity was a talented coder.
So you make him yourtechnical co-founder at CTO.
Five years later when hehas to run a dev team,
it doesn't work anymore.
It's just broken.
It can't do it.
Right?
It doesn't work.
And so it's at that pointwhere I think it becomes
(10:21):
really difficult to say.
Do I even have enoughinformation now to
assess whether or not Ishould want to do this?
And we feel guiltyfor not doing it.
Yeah.
'cause we're like, you know,let's say we've raised,
raised money right now,we're like, look, the whole
point was to grow this thing.
Or at least, so I thought, um,I hadn't, I hadn't experienced
this part where I didn'trealize that as this thing
grew, I'd become less happy.
But now this thing has grown.
(10:41):
It's a real Joby type job.
I don't like it.
Like I just like, I don'tget to do the things that I
enjoyed and how we got here.
I'm surrounded by a bunchof people that I kind
of had to hire 'causewe needed the HR person.
Yeah, we neededthe CFO we needed.
But I don't really like them.
I don't wanna spendmore time with them.
I don't think a lot ofpeople talk about this.
You start to lookaround and you're like.
If this company washiring, I wouldn't apply.
(11:02):
Right?
Yeah, exactly.
It's my own company.
Right, because it's Becauseit's changed so much.
Yeah.
You've gone from, you wentfrom Play-Doh to Legos, right?
It went from fullon, freeform, messy.
Make it into whatever youwant, smashed it up, start
over again easily as youcan to something where
everything's now standardized.
Everything came with aninstruction set there.
There's a clear thing we haveto go do, and we just have
(11:23):
to repeat that over and overand over again, and all of
a sudden it's like, yeah, Idon't wanna do that anymore.
I sat across from the, the guyI mentioned that we'd kinda
made like a CTO, if you will.
I had definitely, he wouldn'tsay it, but I could definitely
read it on his face that hewas clearly in a place where
like he just wasn't happy.
Yeah.
And so I sat down with him.
We were sitting downwith him in my office
(11:43):
and what's funny is like.
I'm talking to him like now.
I remember talking to him as ifhe was like this really old guy.
Right.
And I felt awkward that Iwas 26 and he was really
old and he had a family.
Like, again, don't tell me the
age.
Please don't tell us the age.
Don't say it out loud.
Will
32. Oh, he was 32.
God.
Right.
I was talking tohim like he was 72.
(12:04):
Okay.
And I, I remember being like,you know, at this point in
your career, in your life.
Yeah.
You know, like where thingshave changed or I mean.
I gotta give you an idea wheremy perspective was, right?
Anyway, anyway, I'mlike, you know, you don't
have to be a manager.
You're, you're anamazing developer.
You amazing code, amazinga, uh, systems architect.
Do you want to just do that?
And, and I remember like.
Just this moment, this lookon his face, like I can,
(12:27):
I can.
Yeah.
Like, like, yeah, I
can just do what I enjoy.
And again, I couldtell we'd kind of like
pushed him into this,
but how lucky was he in thatmoment to have somebody else
that could tell him that?
Yeah.
As a founder, no one tells
you that.
No one tells you that.
Right, right.
And and I think that a bigpart of that is because
if you think about thatdecision, if you think about
what's wrapped up in that.
It's a highly contrastedcoin with two sides, right?
(12:50):
Because if you refuse to evolve,is that just founder immaturity?
Are you just not matureenough to do this?
Or is it like the exactopposite, which is that you
are so self-aware that you knowyou're not capable of, of doing
this thing and damn, are thosetwo things a long way apart with
you sitting in the middle going,I don't know, I just don't know.
(13:10):
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.
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.
(13:34):
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.
Okay?
So, so if we're beingintrospective about it and
we say, Hey, on the one hand,like, I'm kind of committed
to this thing, right?
You know, uh, whether Iraise money or whether I
use my own money, whatever.
Like it's, it's my baby, right?
Like, I'm kind ofcommitted to it.
(13:55):
If I don't moveforward with this.
What does that actually mean?
Like, it, it's one thing foryou and I to say, like, like
kind of amorphously, Hey,you don't have to, you know,
love it or you, you might notlike your job, but you still
have to respond in some way.
And so here are like the, thetwo critical decision points.
One is, here'swhat I want to do.
Like, maybe I just wanna goback to building product or
(14:16):
do sales, or do whatever.
And then here's what I thinkI have to do when and when
I say I think I have to do,because in my mind, I believe
that if I don't keep doingthat thing, that thing that
I don't want to do, that I'mgonna be in a position where I'm
gonna get fired or, you know,uh, the board or, or my, my
employees or whatever are gonnalook down on me part of it.
(14:37):
And most people justdon't understand this.
It's just being honest.
If this is a job, you knowthat, that I'm, I'm here to
do the CEO job or, you know,c-level job, whatever it is.
I get it.
I get it.
And, and, and I'mwilling to do it.
Right.
I think part of it is, thisisn't me just being arrogant,
like, you know, or entitled.
Right.
I'm willing to do the job I am.
Yeah.
Yeah.
However, the job that I'd reallylike to do, the one that I think
(15:00):
I could be more effective at.
Is this, by the way, justbefore I complete that
thought, a lot of times whatthat thing is, Ryan, and I
think you've seen this withplenty of other companies, is
like day-to-day management.
Yeah.
Like, like ops.
Yeah.
Right?
Like and so there are some
people that love it.
No, really that's to thepoint that go find them.
And I remember at the time.
(15:21):
I had found a, a person thatwas working for us, uh, that
was on the staff, I should say.
And she was amazing.
And I remember,
I remember thinking,she's so experienced.
She's been around for so long.
She was 31.
And, and again, she was61 in my mind, you know?
Right, right.
It's an
entirely different decade.
Yeah, exactly.
(15:41):
And, uh, and so, you know, Ibrought her in to kind of be
that, that, that ops COO person.
And it worked out great.
And it worked out great.
But it made me realize howmuch I hated that job and how
much it becomes obvious toeveryone that works with you,
that you don't like that job.
Yeah.
And becomes pretty obviousthat they also don't like
the way you do that job.
That's what I'm cases, right?
(16:01):
Yeah.
Right.
Like not only do you notlike it, I don't like it
when you do it either.
Right.
You're just not a great manager.
Go away.
Which is the, the the otherpart that I wanna put in here.
Think about the cost.
Oh yeah.
Of doing the job youdon't like poorly.
Like if you're phoning it inor trying your hardest and
you're just not that good at it.
Right.
Take, go back to mydeveloper guy, my CTO guy.
(16:22):
Right.
In his case, he's shown upevery day and he's doing
a job, the the CTO managerjob, or he's doing, you
know, performance reportsand all this bullshit, right?
And, but what he wants tobe doing is writing code,
so it becomes pretty obviousto all the people that
work with him that he'drather be writing code Yep.
Than doing yourperformance review.
Right.
(16:43):
And so I think the samewith the, you know, the, the
leadership, the founders,what, what have you.
Your team can tell ifyou're doing a job you
don't want to do for sure.
And that's a really bad look.
Yeah.
And then sometimes there's sucha huge contrast to it too, which
I think part of why they canunderstand that, that you're,
you're mailing it in becausethey have seen you on fire.
They have seen you.
At peak performance, they haveseen you doing a thing that you
(17:05):
really love, which is probablywhy they decided to follow
you into startup, dim in thefirst place a hundred percent.
And now you're thisentirely different human
that no longer fits.
Yeah.
And, and again, there'san enthusiasm that
comes with it, right?
Yeah.
Never at any point did Iwalk into a meeting about
an upcoming meeting withany level of enthusiasm.
Right.
Like I'm checking my phoneor my watch the entire time.
(17:25):
Yeah.
Uh, during the meeting.
Be like, how can I get outtathe meeting that I started?
Whereas like if we're,if you and I are on a
whiteboard developing product
Yeah,
we're brainstorming.
I could be there forever.
Yeah, exactly.
Like someone willhave to come in
and tube fetus at somepoint, like we're Yeah,
exactly.
Right.
So part of what we're talkingabout is how it affects us
as founders so that you know,whether or not we've grown.
(17:46):
I think also by proxy, you know,we're also talking about how
do we see this in, in our team.
Right where we've essentiallyput people in positions that
they probably shouldn't be in,or we, we haven't stopped to
maybe reaffirm, is this reallywhat you want to keep doing?
Yeah.
And, and again, I thinkit's, it can be a really hard
question because there's somany other influences I. You
know, depending on like, isthe business on an upswing?
(18:08):
Is the business on a downswing?
Has it plateaued andjust been doing the same
thing for a long time?
That can absolutely changeyour emotional state, which is
clearly gonna impact your, yourability to make the decision.
And look, I think partof it for me was, was the
realization that I. Adaptingmy role didn't mean changing
who I was at that point.
It meant letting go ofsomething that, that I was
(18:29):
hating so that I could do whatI loved, and I, I was able to
find a way to, to do that atthat point, which was nice.
But it was difficult, right?
The first was theacknowledgement of, oh, I'm
actually not good at this.
And then having to make thedecision that yes, there
was probably some effortthat I could put into it,
that I could, you know, the,the irony being that I was
in a business managementtrack at the time, right.
I was in university for, right,for this specifically, uh, it
(18:52):
tells you something about thequality of that education.
Um, and so.
It really came down to mehaving to just recognize it
first and then become okaywith the idea of letting it go
versus saying, well, no, I, Ifigured this other stuff out.
I'll have to figure thisout too, and not forcing
myself through that keyhole.
Right.
That was, that was thereally hard part for me.
(19:13):
I looked at it as a failure.
I looked at it as a hundredpercent, and again, and
I was young in my career,so I, I honestly just
didn't know any better yet.
I looked at it as, look,you did this thing.
You're now a CEO of a company.
Here's how you're expectedto act and behave and, and,
and how you're supposedto enjoy it and embrace
it, and all these things.
And I, I was just like, yeah,but I don't, like, I get
it and I'm, I'm grateful.
(19:35):
This wasn't a lack of gratitude.
I'm grateful yeah, forthis opportunity, but
I don't want this job.
Yeah.
It's a very weird thingto say as the leadership
of an organization.
Yeah.
Like I get it, but Idon't want this job.
I mean, like your parents sayinglike, I get that we're supposed
to look after you, but yeah,you're kind of on your own.
Well, it goes back to what,what I said before when you
(19:55):
were, you were going throughthe, that scenario, it's
like, but luckily somebodyelse told them that, right?
Mm-hmm.
Somebody else was ableto say like, Hey, what if
you just didn't do this?
Like there's just nobodyelse to, not only is there
nobody else to tell youthat there isn't even really
anybody else for you to tell.
It's a conversation you havewith yourself and nobody else.
Like that's super uncomfortable.
Right.
Particularly at at a time whereyou're questioning who you are.
(20:16):
Also, this is a tough one.
Sometimes the best place for youisn't at that company at all.
That's the path that I took.
I. Right.
I essentially quitmy own company.
Now, with that being said,I realized that the company
had grown to a point whereit didn't really matter
if I was there anymore.
So like when I say quit, itwasn't like I was rage quitting.
I was like, you know,it kind of, I've done
what I needed to do.
There's like, if, if,if we grow 10 x more.
(20:40):
It'll make no difference.
What's me being there willmake no difference whatsoever.
Yeah.
Which is kind of hard, uh,self-realization, but, so I just
went and go, did something else.
Right.
Started eight other companies.
Yeah.
I think I had at least the,the self-awareness to realize
that what I was doing, eventhough it was successful, I.
It wasn't really whatI wanted to be doing.
Yeah.
And, and I think thatthat's a hard call to make.
(21:00):
That could have gone very wrong.
I could have spent the next 20years of my life ruining the
day that you know, that, thatI made the dumbest decision
to, to not work at the onething in my life that worked.
What happens when.
This, 'cause this cansometimes be taken
outta your hands, right?
We, I, I said before thatnobody's gonna come to
you and say, Hey, what ifyou just did this thing?
But there are times where peopledo come and say, Hey, you're
not gonna do this thing anymore.
(21:21):
Right?
It's called the board,it's called investors.
So what happens at,at that point, right?
Is this a betrayal of, of,of the baby you raised?
Or is this, you know, anecessary move to ensure
this survival of the company?
Right.
Like
I, I, I'm not a big fanof ever taking the founder
outta the business.
Yeah.
And don't get me wrong, I'mnot saying every founder
is uniquely qualified.
You know, I wasn't Right.
But you know, you know, I'vetalked about this a lot.
(21:42):
I, I, I, I think when youmess with the DNA, like
that, it rarely works.
Like I, I get the argumentevery time, the argument,
every time is like, look,we brought this person in.
They, they would've never beenable to get this job if they
hadn't started the company.
Totally get it, right?
Yeah.
Get it.
And now that they're here,uh, the company's grown beyond
them, uh, they can't see it.
We can see it.
Name your problem, right?
(22:04):
I get it.
I do.
But I rarely see thenext person that comes
in hit it outta the park.
This is always withprivate equity.
Private equity is whole thingis they come in, they buy a
company, they shred it apart, solike they, to get the cost down
so they can sell it to profit.
And I rarely see a company whereit's like, and then private
equity came in and, and it wasso much better of a company.
(22:24):
I'm sure thefinances got better.
But I'm talking, workingthere better on paper.
Yes.
Actual company.
Right.
In
any other way?
Rarely.
Every time I hear somebody's,I'm working for a company and
they're private equity backed,my first words are, I'm sorry,
I'm sorry about your loss.
Right.
Like, because, and they allinstantly know what I'm saying?
I've never had somebodygo, yeah, yeah.
Oh no.
It's wonderful.
(22:44):
It's great.
I've never hadsomeone so Oh, oh no.
It's wonderful.
Yeah, right.
They're always like,yeah, you get it.
Here's what I would say.
I think the hardest thing forus is again, this concept that
the change isn't a failure.
The change isn't a failure.
Right.
It's an evolution.
It sucks.
It's hard.
It'd be great if things werejust always the way they
were in our halcyon days.
(23:05):
Right?
But they're not, and herewe are and we We have
to make a transition.
Yeah.
We have to make atransition and look
like if your dream wasbig enough to outgrow you.
That's not a shame, that's abadge of honor, if anything.
Right?
It's a sign of like theultimate success, right?
Yeah.
You built something that managedto pick up enough steam that
it outgrew you and can out goon without you emotionally.
(23:26):
That might be tough, butlike if you just look at
that from a purely objectivestandpoint, pretty damn cool.
It's sending thekids off to college.
Right?
The the whole goal was to,was to that, to too close to
home.
Now will, we're gettingreal close to that buddy.
That's that.
To be like, ha ha, so farin future, doesn't matter.
Not talking about me,are you sir? Damn.
(23:47):
I.
My daughter Summer walkedinto the room the other day,
and I don't know if you'vegotten this, I'm sure you have
with your daughter Hannah.
'cause they'reabout the same age.
I saw a teenager walk in theroom and she's teenage 13.
Right, dude.
But I mean, I saw a,yeah, a young woman.
I didn't see, I didn't seemy little girl anymore.
I saw a young, I double.
I had to dig a double take.
Yeah.
Because how was it?
What the hell?
We just walked through.
(24:07):
Yeah.
Who was that?
Right?
It was weird.
And so.
All these emotions come crashingthrough the same thing, right?
Where I'm like, oh my God.
Like to your point,she's gonna be in college
in like five seconds.
They're outgrowing whatwe currently know now.
Like as a parent, we don'tget to choose whether we wanna
continue that role, right?
We have to continueto, to level up.
Like I figured outfinally how to be the, the
parent of an adolescent.
(24:28):
Now I have to learn how tobe the parent of a teacher.
Pretty soon have to learnhow to be the parent
of a college student.
Um, I suppose some of it getseasier as it goes on because
they start to take over more andmore, but very similar feeling.
Very, very similar feeling.
That's the thing,like it's a trophy.
The fact that we made it thisfar, like is is heart wrenching?
It is.
To, to, to watch our daughterslike pack up for college.
Right.
On the other hand, andthis is again the analogy,
(24:51):
we have to realize whatit took to get us here.
Yes.
It's tough.
Yes.
It's, it's a very difficultpart for all of us to be able
to see something we built andnourished, kind of grow beyond
us and in some cases without us.
But here's what I would say.
Step back for aminute, step back.
I don't wanna mournwhat happened, okay?
I wanna celebrate what happened.
I wanna celebratewhat we've built.
(25:13):
How we've built it and thefact that, and you said it,
Ryan, the fact that we evenhave the optionality of being
able to make this transitionbecause a tiny fraction of a
percentage of entrepreneurswill ever get this opportunity.
And if we are one of thefew, few, few that ever
gets this opportunity,cherish the opportunity and
make an important decisionto move the hell on.
(25:37):
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 bootstrappedfounders and the advisors
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.
(25:57):
I hope to see you inside.
Welcome back to their episodeof the Startup Therapy Podcast.
This is Ryan Rutan joint,as always by my friend, the
founder, and CO of startups.com.
Will Schroeder will haveyou ever walked into
something that you've builtentirely from scratch?
Ground up, zero to one moment.
Then wandered through thedoors and just felt like
you no longer belong there.
(00:20):
A lot.
There was not like manytimes, but like, like an
overwhelming feeling of that.
Early in my career, uh, whenI was building a company,
companies started gettingbig, like real big as it's
getting bigger, you know,I'm still young at time.
I'm like 26 as it'sgetting bigger.
I'm sitting there going.
Okay.
Well, you know, I used tobuild websites that was,
you know, part, part ofwhat we did as an agency.
(00:41):
And I, yeah.
I don't really doany code anymore.
And now I don't doany design anymore.
Yeah.
And now I don't really dothe, the strategy anymore.
And one day I walk in andI'm like, what do I do here?
Right.
Yeah.
Like, I'm managing, I'm, I'mhaving meetings about meetings.
I don't produce a goddamn thing.
Yeah.
And it was miserable.
Yeah.
Miserable.
Right.
It's funny, ma'am,you just described it.
(01:02):
I had the samething happen to me.
I've seen this happen withcountless founders where
it's like one day you justwalk in, it's as if you
walk into a glass wall.
It felt that way to me.
It was like, it was such asudden sort of thing where
it's like I was the lastone to kind of know that the
company had had moved on andthat I no longer fit there.
And it, it felt likesuch a betrayal of
everything I'd built.
(01:22):
I'm like.
This is only all herebecause of me, but now
I don't need to be here.
Like, what the
f Like I
didn't know how to deal with it.
Let me tee that up a bit.
So a lot of times what'llhappen is, you know, you and
I'll talk to founders andyou can tell that like they
appreciate what they've built.
Yeah.
But they don't liketheir job anymore.
Yeah, yeah.
Oh, a hundred percent.
And,
and I guarantee we've got afair amount of people that are
(01:43):
listening to this, this episodebe like, yeah, that's me.
And but here's the problem.
We feel guilty about it.
We feel guilty.
That we don't like the jobbecause it makes us ungrateful.
I walk in and I remember atthe time, you know, we just
built these two new a hundredthousand square foot buildings.
We had, you know, six or 700people at the time, and I'm
like, I should be so proudof what we have here, and I
(02:03):
am, and I don't like my job.
And, and this isn't me beinglike, entitled, I just didn't
like what I was doing anymore.
Like, there's nothingwrong with that.
I, but.
Definitely didn't know that.
It's funny, we go throughsome of those things at the
early stages too, right?
Where it's like there are lotsof jobs that have to be done.
As a startup founder,you're doing it all right?
It's chef cook,bottle washer, right?
You're doing it all.
And we're sort of used to it atthat phase, but I think we get
(02:24):
into like where we start to hitour stride and our superpower,
the company starts to growbased on that, and then all of
a sudden that goes away again.
And you're like, butnow what I'm doing?
Isn't what I like to be doing.
I, I know I've shared thiswith you before, but there
was a point at which I wasrunning my agency, you know,
back in the dark ages and ithad been like a two week period
when I was looking back atlike my, my daily journals.
It'd been like a two week periodwhere I had done absolutely
(02:47):
nothing but keep the three mostimportant teams in the business
from fighting with each other.
I had just become like,I was just dad and I was
unprepared to be a father.
At that point, I was right.
20 at this point.
21,
yeah.
And look, and, andsome people love it.
Some people like that'swhat they wanna do.
Like I remember, I rememberwhen I was growing up and
I was reading about likesuperstar CEOs, right?
(03:09):
The Jack Welch era, right?
Where it was like youwere prided on being
an employee, right?
Like now it's all, if you'renot the founder, no one cares.
Right.
But that was a different erawhere like it, you were the
silver-haired 60-year-oldthat finally made it to the,
the corner office type thing.
Yeah.
Climbed your way from,yeah, from nowhere to you.
I It
was all about the, acareer trajectory, right?
(03:30):
Yeah.
Like that all got turned onits head in the startup world
where you're like 23 in theCE and you kind of started
backward, but not too long ago,or maybe it was a long time
ago, and I'm just getting old.
Not too long ago, it was allabout moving up to the C-suite.
Those people werecareer managers.
Like the way you got there,like, here's the thing,
you couldn't have possiblybeen prior to that, right?
(03:51):
You couldn't have possiblybeen Mark Zuckerberg
and you just coded yourway to the top, right?
Like you coded and youwound up at the top 'cause
you started at the top.
And so it fascinates methat like in this, in
kinda this new world.
These folks that came in aslike the really talented coder,
let's say just as an example,wake up one day and they're
(04:11):
like, I'm a manager now.
Like, what thehell just happened?
It's thrust on you.
It's thrust on you.
Yeah.
I mean that's the, the, goingback to management philosophy
from that same period oftime, that's when the Peter
principle was born, right?
Where you get promotedup to your highest
level of inefficiency.
You're, you are agreat junior coder.
We'll make you a,a senior coder.
You're a great senior coder.
We'll make you a, whateverthe next level of that is.
Then you become a directorof technology or something
(04:34):
where now you're nolonger coding, you're
managing the other coders.
'cause you were a great coder.
Turns out you've nevermanaged anybody before.
I watched that happen.
Right, because as we werescaling you, as we were
adding more and more people,same exact thing you said.
Yeah.
Specifically.
I remember one of our, oursenior developers kept getting
promoted Uhhuh, and when Isay kept getting promoted, it
didn't happen outta nowhere.
I was promoting, but as I waswatching it happen, I saw him
(04:56):
get more and more uncomfortable.
Mm-hmm.
Good, smart guy, right?
Yep.
I could tell he was gettingmoved to the top of the ranks
only because he had the seniormost technical knowledge.
Yeah.
Right.
Like he was more technicalthan anyone else.
But as a manager, like he,he wasn't gifted in any way.
Yeah, right.
(05:16):
To your point, he justkept getting pushed there.
The irony was the guy pushinghim was having the same
exact problem, which was me.
Right.
I was like, maybeyou just wanted
company for the misery.
Like,
yeah, yeah, Igotta make sure I'm
not alone in this misery.
So we get to this point wherelike the company that we
built right, was built forwho we were, not who we are.
(05:36):
And I think that's ahard thing for us to
step back and say, huh.
And I think for a lotof reasons, one of
them for me was that.
When I realized I was doingmanagement, and you've drawn
this distinction before too,which is the difference between
management and leadership.
I'm not even gonna goas far as as leadership.
It wasn't that I was likethere were points where I was
leading the company versusversus managing these people.
(05:58):
My own individual abilityto produce felt taken away.
And so for me, right.
That feeling that was the mostoverwhelming, like the literal,
like choking out my oxygenanxiety level, like worrying
about this stuff was when itwould feel like because I had
to manage people, I couldn'tgo do things that I found more
important, more engaging, moreexciting, more valuable, right?
(06:21):
Like whether that was going andtrying to land a new client,
whether that was figuring outa new way to deliver something,
whether that was figuring outwhether we should move from,
you know, move to cold fusion,whatever it was, you know, a
hundred thousand years ago in.
So, you know, like that tome was a big part of it.
And so I think fold.
Like I also wasn't atalented manager by any
stretch of the imagination.
I was not right.
(06:41):
I, I'd had no experience.
I had never even reallybeen managed because
I was so damn young.
I'd never had a real, real job.
And so part of it was.
Absolutely a lack of skill and,and probably a rightful amount
of fear against management.
Sure, sure.
Because I didn't knowwhat I was doing.
But the other part of itwas it, like it took the
fun away from me even hadI been a talented manager.
It's sort of like this, Ilook at it this way, if you're
Christiana Ronaldo, and he'sgetting old now, so we may be
(07:04):
getting close to this point,but let's say Christiana
Ronaldo from, from five yearsago, six years ago, prime peak
performance, and all of a suddenyou're like, you know what?
This guy's the bestplayer in the world.
We should make him a coachso we can have a bunch
more really great players.
Hold aside that he may noteven be a good manager.
Do you think that guy wantsto be watching the game?
That's how I felt every singletime I was managing people felt
(07:26):
like I'm watching the game andhaving to coach them through it.
I'm like, I want togo kick the damn ball.
I don't wanna be off the field.
Painful, super painful.
I was like, in short order.
I was like, man, I missed thedays when we'd all stay up
all night, like working on aproject and just crushing it.
Yes.
And and now it's like, yeah,no one wants to do that.
No.
Right.
Like the only reason we did thatis 'cause you, you did it right.
(07:47):
Like, you know, youpushed us to that end.
I don't know ifyou'll remember this.
There was a point at whichyou remember when we.
We were refinishingthe upper floors in the
offices on Manning, right?
Mm-hmm.
And we had to moveeverybody to the basement.
You remember that?
Where everybody wentto the basement for a
little bit and like wewere down there basement.
It was a war zone.
We had video gamemachines down there.
We had weight racks.
We had desks piledon top of each other.
(08:09):
Yep.
And on two or three occasionsI tried to rally, like,
let's pull an all-nighterand get this done.
Let's bang throughthese clients, whatever.
And it was like, I waslike, yeah, I felt like,
who was the politicianthat did that awful yell.
Do you remember that?
Scream heard aroundthe world where he was.
Anyways, there was noanswer to my rally cry.
I was like, let's do it.
And everybody else is like,um, uh, time for drinks or
(08:31):
whatever, and they're pew gone.
Right.
Such a bad feeling.
I think it's hard for us,uh, you know, as the founders
to take stock in that.
Yeah.
And to be able to say, ah, okay.
The good old days.
We're, we're only good for me.
Right.
Or said differently.
Like, you know, there's alwayspeople like, oh my God, I
remember when the companywas smaller and we all hung
out and blah, blah, blah.
And that's great.
Yeah.
But it's also, you have totake stock and recognize
(08:53):
that like, that's over.
It's the guy who keepstalking about that one
party from college, andyou're like, no, I get it.
I, I get it.
It was fun.
That was 20 years ago.
You were great.
Yeah,
but I get it right.
Uh, like that part of islong since over, and I think
as managers, as founders,we, we get into this spot
where we long for those days.
And what's so hard is we'rethe one in control of where
(09:15):
this company is gone, but thecompany evolves beyond us.
Yeah.
That's what this is all about.
The company evolves beyond us.
It's one thing when it evolves,evolves beyond everybody else.
It's really hard whenit evolves beyond us.
So the question becomes.
Do we wanna grow with it?
Do we wanna change?
It's hard, and I think thisis, it's, it's a question that
it can be really difficultto answer at that point.
(09:38):
The point where youhave to answer it.
Because you might notbe well armed for it.
Right.
You're, you're nowrealizing that there's
a new, new world order.
I have to have adifferent set of skills.
I have to have a different set.
Yep.
And, and so you're,you're simultaneously
asked, being asked, doyou want to do this thing?
Are you capable of doing this?
You know, even if you sayyou want to, can you do it?
We've seen this happen too,like sometimes companies
(09:58):
legitimately outgrow thefounder or we see it outgrow
one of the founding members.
I, I think you and I haveused the example before where
like, your best buddy fromuniversity was a talented coder.
So you make him yourtechnical co-founder at CTO.
Five years later when hehas to run a dev team,
it doesn't work anymore.
It's just broken.
It can't do it.
Right?
It doesn't work.
And so it's at that pointwhere I think it becomes
(10:21):
really difficult to say.
Do I even have enoughinformation now to
assess whether or not Ishould want to do this?
And we feel guiltyfor not doing it.
Yeah.
'cause we're like, you know,let's say we've raised,
raised money right now,we're like, look, the whole
point was to grow this thing.
Or at least, so I thought, um,I hadn't, I hadn't experienced
this part where I didn'trealize that as this thing
grew, I'd become less happy.
But now this thing has grown.
(10:41):
It's a real Joby type job.
I don't like it.
Like I just like, I don'tget to do the things that I
enjoyed and how we got here.
I'm surrounded by a bunchof people that I kind
of had to hire 'causewe needed the HR person.
Yeah, we neededthe CFO we needed.
But I don't really like them.
I don't wanna spendmore time with them.
I don't think a lot ofpeople talk about this.
You start to lookaround and you're like.
If this company washiring, I wouldn't apply.
(11:02):
Right?
Yeah, exactly.
It's my own company.
Right, because it's Becauseit's changed so much.
Yeah.
You've gone from, you wentfrom Play-Doh to Legos, right?
It went from fullon, freeform, messy.
Make it into whatever youwant, smashed it up, start
over again easily as youcan to something where
everything's now standardized.
Everything came with aninstruction set there.
There's a clear thing we haveto go do, and we just have
(11:23):
to repeat that over and overand over again, and all of
a sudden it's like, yeah, Idon't wanna do that anymore.
I sat across from the, the guyI mentioned that we'd kinda
made like a CTO, if you will.
I had definitely, he wouldn'tsay it, but I could definitely
read it on his face that hewas clearly in a place where
like he just wasn't happy.
Yeah.
And so I sat down with him.
We were sitting downwith him in my office
(11:43):
and what's funny is like.
I'm talking to him like now.
I remember talking to him as ifhe was like this really old guy.
Right.
And I felt awkward that Iwas 26 and he was really
old and he had a family.
Like, again, don't tell me the
age.
Please don't tell us the age.
Don't say it out loud.
Will
32. Oh, he was 32.
God.
Right.
I was talking tohim like he was 72.
(12:04):
Okay.
And I, I remember being like,you know, at this point in
your career, in your life.
Yeah.
You know, like where thingshave changed or I mean.
I gotta give you an idea wheremy perspective was, right?
Anyway, anyway, I'mlike, you know, you don't
have to be a manager.
You're, you're anamazing developer.
You amazing code, amazinga, uh, systems architect.
Do you want to just do that?
And, and I remember like.
Just this moment, this lookon his face, like I can,
(12:27):
I can.
Yeah.
Like, like, yeah, I
can just do what I enjoy.
And again, I couldtell we'd kind of like
pushed him into this,
but how lucky was he in thatmoment to have somebody else
that could tell him that?
Yeah.
As a founder, no one tells
you that.
No one tells you that.
Right, right.
And and I think that a bigpart of that is because
if you think about thatdecision, if you think about
what's wrapped up in that.
It's a highly contrastedcoin with two sides, right?
(12:50):
Because if you refuse to evolve,is that just founder immaturity?
Are you just not matureenough to do this?
Or is it like the exactopposite, which is that you
are so self-aware that you knowyou're not capable of, of doing
this thing and damn, are thosetwo things a long way apart with
you sitting in the middle going,I don't know, I just don't know.
(13:10):
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.
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.
(13:34):
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.
Okay?
So, so if we're beingintrospective about it and
we say, Hey, on the one hand,like, I'm kind of committed
to this thing, right?
You know, uh, whether Iraise money or whether I
use my own money, whatever.
Like it's, it's my baby, right?
Like, I'm kind ofcommitted to it.
(13:55):
If I don't moveforward with this.
What does that actually mean?
Like, it, it's one thing foryou and I to say, like, like
kind of amorphously, Hey,you don't have to, you know,
love it or you, you might notlike your job, but you still
have to respond in some way.
And so here are like the, thetwo critical decision points.
One is, here'swhat I want to do.
Like, maybe I just wanna goback to building product or
(14:16):
do sales, or do whatever.
And then here's what I thinkI have to do when and when
I say I think I have to do,because in my mind, I believe
that if I don't keep doingthat thing, that thing that
I don't want to do, that I'mgonna be in a position where I'm
gonna get fired or, you know,uh, the board or, or my, my
employees or whatever are gonnalook down on me part of it.
(14:37):
And most people justdon't understand this.
It's just being honest.
If this is a job, you knowthat, that I'm, I'm here to
do the CEO job or, you know,c-level job, whatever it is.
I get it.
I get it.
And, and, and I'mwilling to do it.
Right.
I think part of it is, thisisn't me just being arrogant,
like, you know, or entitled.
Right.
I'm willing to do the job I am.
Yeah.
Yeah.
However, the job that I'd reallylike to do, the one that I think
(15:00):
I could be more effective at.
Is this, by the way, justbefore I complete that
thought, a lot of times whatthat thing is, Ryan, and I
think you've seen this withplenty of other companies, is
like day-to-day management.
Yeah.
Like, like ops.
Yeah.
Right?
Like and so there are some
people that love it.
No, really that's to thepoint that go find them.
And I remember at the time.
(15:21):
I had found a, a person thatwas working for us, uh, that
was on the staff, I should say.
And she was amazing.
And I remember,
I remember thinking,she's so experienced.
She's been around for so long.
She was 31.
And, and again, she was61 in my mind, you know?
Right, right.
It's an
entirely different decade.
Yeah, exactly.
(15:41):
And, uh, and so, you know, Ibrought her in to kind of be
that, that, that ops COO person.
And it worked out great.
And it worked out great.
But it made me realize howmuch I hated that job and how
much it becomes obvious toeveryone that works with you,
that you don't like that job.
Yeah.
And becomes pretty obviousthat they also don't like
the way you do that job.
That's what I'm cases, right?
(16:01):
Yeah.
Right.
Like not only do you notlike it, I don't like it
when you do it either.
Right.
You're just not a great manager.
Go away.
Which is the, the the otherpart that I wanna put in here.
Think about the cost.
Oh yeah.
Of doing the job youdon't like poorly.
Like if you're phoning it inor trying your hardest and
you're just not that good at it.
Right.
Take, go back to mydeveloper guy, my CTO guy.
(16:22):
Right.
In his case, he's shown upevery day and he's doing
a job, the the CTO managerjob, or he's doing, you
know, performance reportsand all this bullshit, right?
And, but what he wants tobe doing is writing code,
so it becomes pretty obviousto all the people that
work with him that he'drather be writing code Yep.
Than doing yourperformance review.
Right.
(16:43):
And so I think the samewith the, you know, the, the
leadership, the founders,what, what have you.
Your team can tell ifyou're doing a job you
don't want to do for sure.
And that's a really bad look.
Yeah.
And then sometimes there's sucha huge contrast to it too, which
I think part of why they canunderstand that, that you're,
you're mailing it in becausethey have seen you on fire.
They have seen you.
At peak performance, they haveseen you doing a thing that you
(17:05):
really love, which is probablywhy they decided to follow
you into startup, dim in thefirst place a hundred percent.
And now you're thisentirely different human
that no longer fits.
Yeah.
And, and again, there'san enthusiasm that
comes with it, right?
Yeah.
Never at any point did Iwalk into a meeting about
an upcoming meeting withany level of enthusiasm.
Right.
Like I'm checking my phoneor my watch the entire time.
(17:25):
Yeah.
Uh, during the meeting.
Be like, how can I get outtathe meeting that I started?
Whereas like if we're,if you and I are on a
whiteboard developing product
Yeah,
we're brainstorming.
I could be there forever.
Yeah, exactly.
Like someone willhave to come in
and tube fetus at somepoint, like we're Yeah,
exactly.
Right.
So part of what we're talkingabout is how it affects us
as founders so that you know,whether or not we've grown.
(17:46):
I think also by proxy, you know,we're also talking about how
do we see this in, in our team.
Right where we've essentiallyput people in positions that
they probably shouldn't be in,or we, we haven't stopped to
maybe reaffirm, is this reallywhat you want to keep doing?
Yeah.
And, and again, I thinkit's, it can be a really hard
question because there's somany other influences I. You
know, depending on like, isthe business on an upswing?
(18:08):
Is the business on a downswing?
Has it plateaued andjust been doing the same
thing for a long time?
That can absolutely changeyour emotional state, which is
clearly gonna impact your, yourability to make the decision.
And look, I think partof it for me was, was the
realization that I. Adaptingmy role didn't mean changing
who I was at that point.
It meant letting go ofsomething that, that I was
(18:29):
hating so that I could do whatI loved, and I, I was able to
find a way to, to do that atthat point, which was nice.
But it was difficult, right?
The first was theacknowledgement of, oh, I'm
actually not good at this.
And then having to make thedecision that yes, there
was probably some effortthat I could put into it,
that I could, you know, the,the irony being that I was
in a business managementtrack at the time, right.
I was in university for, right,for this specifically, uh, it
(18:52):
tells you something about thequality of that education.
Um, and so.
It really came down to mehaving to just recognize it
first and then become okaywith the idea of letting it go
versus saying, well, no, I, Ifigured this other stuff out.
I'll have to figure thisout too, and not forcing
myself through that keyhole.
Right.
That was, that was thereally hard part for me.
(19:13):
I looked at it as a failure.
I looked at it as a hundredpercent, and again, and
I was young in my career,so I, I honestly just
didn't know any better yet.
I looked at it as, look,you did this thing.
You're now a CEO of a company.
Here's how you're expectedto act and behave and, and,
and how you're supposedto enjoy it and embrace
it, and all these things.
And I, I was just like, yeah,but I don't, like, I get
it and I'm, I'm grateful.
(19:35):
This wasn't a lack of gratitude.
I'm grateful yeah, forthis opportunity, but
I don't want this job.
Yeah.
It's a very weird thingto say as the leadership
of an organization.
Yeah.
Like I get it, but Idon't want this job.
I mean, like your parents sayinglike, I get that we're supposed
to look after you, but yeah,you're kind of on your own.
Well, it goes back to what,what I said before when you
(19:55):
were, you were going throughthe, that scenario, it's
like, but luckily somebodyelse told them that, right?
Mm-hmm.
Somebody else was ableto say like, Hey, what if
you just didn't do this?
Like there's just nobodyelse to, not only is there
nobody else to tell youthat there isn't even really
anybody else for you to tell.
It's a conversation you havewith yourself and nobody else.
Like that's super uncomfortable.
Right.
Particularly at at a time whereyou're questioning who you are.
(20:16):
Also, this is a tough one.
Sometimes the best place for youisn't at that company at all.
That's the path that I took.
I. Right.
I essentially quitmy own company.
Now, with that being said,I realized that the company
had grown to a point whereit didn't really matter
if I was there anymore.
So like when I say quit, itwasn't like I was rage quitting.
I was like, you know,it kind of, I've done
what I needed to do.
There's like, if, if,if we grow 10 x more.
(20:40):
It'll make no difference.
What's me being there willmake no difference whatsoever.
Yeah.
Which is kind of hard, uh,self-realization, but, so I just
went and go, did something else.
Right.
Started eight other companies.
Yeah.
I think I had at least the,the self-awareness to realize
that what I was doing, eventhough it was successful, I.
It wasn't really whatI wanted to be doing.
Yeah.
And, and I think thatthat's a hard call to make.
(21:00):
That could have gone very wrong.
I could have spent the next 20years of my life ruining the
day that you know, that, thatI made the dumbest decision
to, to not work at the onething in my life that worked.
What happens when.
This, 'cause this cansometimes be taken
outta your hands, right?
We, I, I said before thatnobody's gonna come to
you and say, Hey, what ifyou just did this thing?
But there are times where peopledo come and say, Hey, you're
not gonna do this thing anymore.
(21:21):
Right?
It's called the board,it's called investors.
So what happens at,at that point, right?
Is this a betrayal of, of,of the baby you raised?
Or is this, you know, anecessary move to ensure
this survival of the company?
Right.
Like
I, I, I'm not a big fanof ever taking the founder
outta the business.
Yeah.
And don't get me wrong, I'mnot saying every founder
is uniquely qualified.
You know, I wasn't Right.
But you know, you know, I'vetalked about this a lot.
(21:42):
I, I, I, I think when youmess with the DNA, like
that, it rarely works.
Like I, I get the argumentevery time, the argument,
every time is like, look,we brought this person in.
They, they would've never beenable to get this job if they
hadn't started the company.
Totally get it, right?
Yeah.
Get it.
And now that they're here,uh, the company's grown beyond
them, uh, they can't see it.
We can see it.
Name your problem, right?
(22:04):
I get it.
I do.
But I rarely see thenext person that comes
in hit it outta the park.
This is always withprivate equity.
Private equity is whole thingis they come in, they buy a
company, they shred it apart, solike they, to get the cost down
so they can sell it to profit.
And I rarely see a company whereit's like, and then private
equity came in and, and it wasso much better of a company.
(22:24):
I'm sure thefinances got better.
But I'm talking, workingthere better on paper.
Yes.
Actual company.
Right.
In
any other way?
Rarely.
Every time I hear somebody's,I'm working for a company and
they're private equity backed,my first words are, I'm sorry,
I'm sorry about your loss.
Right.
Like, because, and they allinstantly know what I'm saying?
I've never had somebodygo, yeah, yeah.
Oh no.
It's wonderful.
(22:44):
It's great.
I've never hadsomeone so Oh, oh no.
It's wonderful.
Yeah, right.
They're always like,yeah, you get it.
Here's what I would say.
I think the hardest thing forus is again, this concept that
the change isn't a failure.
The change isn't a failure.
Right.
It's an evolution.
It sucks.
It's hard.
It'd be great if things werejust always the way they
were in our halcyon days.
(23:05):
Right?
But they're not, and herewe are and we We have
to make a transition.
Yeah.
We have to make atransition and look
like if your dream wasbig enough to outgrow you.
That's not a shame, that's abadge of honor, if anything.
Right?
It's a sign of like theultimate success, right?
Yeah.
You built something that managedto pick up enough steam that
it outgrew you and can out goon without you emotionally.
(23:26):
That might be tough, butlike if you just look at
that from a purely objectivestandpoint, pretty damn cool.
It's sending thekids off to college.
Right?
The the whole goal was to,was to that, to too close to
home.
Now will, we're gettingreal close to that buddy.
That's that.
To be like, ha ha, so farin future, doesn't matter.
Not talking about me,are you sir? Damn.
(23:47):
I.
My daughter Summer walkedinto the room the other day,
and I don't know if you'vegotten this, I'm sure you have
with your daughter Hannah.
'cause they'reabout the same age.
I saw a teenager walk in theroom and she's teenage 13.
Right, dude.
But I mean, I saw a,yeah, a young woman.
I didn't see, I didn't seemy little girl anymore.
I saw a young, I double.
I had to dig a double take.
Yeah.
Because how was it?
What the hell?
We just walked through.
(24:07):
Yeah.
Who was that?
Right?
It was weird.
And so.
All these emotions come crashingthrough the same thing, right?
Where I'm like, oh my God.
Like to your point,she's gonna be in college
in like five seconds.
They're outgrowing whatwe currently know now.
Like as a parent, we don'tget to choose whether we wanna
continue that role, right?
We have to continueto, to level up.
Like I figured outfinally how to be the, the
parent of an adolescent.
(24:28):
Now I have to learn how tobe the parent of a teacher.
Pretty soon have to learnhow to be the parent
of a college student.
Um, I suppose some of it getseasier as it goes on because
they start to take over more andmore, but very similar feeling.
Very, very similar feeling.
That's the thing,like it's a trophy.
The fact that we made it thisfar, like is is heart wrenching?
It is.
To, to, to watch our daughterslike pack up for college.
Right.
On the other hand, andthis is again the analogy,
(24:51):
we have to realize whatit took to get us here.
Yes.
It's tough.
Yes.
It's, it's a very difficultpart for all of us to be able
to see something we built andnourished, kind of grow beyond
us and in some cases without us.
But here's what I would say.
Step back for aminute, step back.
I don't wanna mournwhat happened, okay?
I wanna celebrate what happened.
I wanna celebratewhat we've built.
(25:13):
How we've built it and thefact that, and you said it,
Ryan, the fact that we evenhave the optionality of being
able to make this transitionbecause a tiny fraction of a
percentage of entrepreneurswill ever get this opportunity.
And if we are one of thefew, few, few that ever
gets this opportunity,cherish the opportunity and
make an important decisionto move the hell on.
(25:37):
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 bootstrappedfounders and the advisors
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.
(25:57):
I hope to see you inside.
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