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The "No BS" version of how startups are really built, taught by actual startup Founders who have lived through all of it. Hosts Wil Schroter and Ryan Rutan talk candidly about the intense struggles Founders face both personally and professionally as they try to turn their idea into something that will change the world.
Welcome back to the episode of
the Startup Therapy Podcast.
This is Ryan Rutan, joined
as always by my friend, the
founder and CEO of startups.
com, Will Schroeder.
Will, we talk about the
sacrifices, the costs, the
benefits, all the complicated
calculus of what it means to
be a founder a lot, but how
often does it come around
where we're really like,
it's thrown in our face.
We're forced to examine this
whole question of, okay,
now, even if we're on the
other side of it and we've,
we've achieved some success.
Was it worth it?
How did it all net out?
Right.
You know, it's interesting
because we all have like a
reflection or, or, or like,
you know, moments where we're
kind of just thinking about the
past and kind of where we are
right now and things like that.
But it's, I think it's rare
that you have like, call
it a moment of gratitude
where, where, where something
specifically like a, a very
seminal moment makes you go.
That was kind of worth it or
or the opposite which was damn
that was absolutely not worth it
Yeah, and that actually happened
to me totally unexpectedly
like a week ago I'm doing
this this middle middle school
class on entrepreneurship
in my daughter's school
for their school.
It's fifth through eighth
grade That comprises the middle
school and I you know, I teach
this class on entrepreneurship
Well at the beginning of the
class I do like a little like
TED talk about my journey and
things like that and kind of
how I became an entrepreneur
and really all the crazy stuff
that I had to go through.
And it's rare.
And I know we talked about
this in a previous episode that
you get to do a Ted talk about
your life in front of your kid.
It was cool though,
because like she didn't
have to respond to it.
Right.
You know, my, my, my daughter's
awesome, but like, she was
in a room full of kids.
So it wasn't like I was
sitting in the living room,
lecturing her, you didn't
corner her at dinner.
Right.
Yeah.
Yeah.
Yeah.
And so she could
just take it in.
We paid
for this roast beef
we're eating tonight.
That's
usually where it comes from.
Right.
So we do this whole thing,
uh, class sober, and we get
out and we hop in the car
and she's a little bit quiet
initially and we're, we're
driving home and she's like,
Dad, what you said was amazing.
Like, I had no idea what you
went through to create the
life that we have for us.
And I just want to say,
I'm really grateful.
And I never expected that.
And it was unprompted.
And it just like, I was like
beside myself and it occurred to
me like, 40 years of grinding.
You know, uh, 30 years of
my career, 10 years of just
trying to get out of the
shit situation that I was in.
Yeah.
I finally got a thank
you, so to speak.
Or, or more, more specifically,
it wasn't about the thank
you, I shouldn't say that.
I finally got a, damn dude,
that was kind of worth it.
In five seconds.
It was amazing.
I, I never saw that coming.
But it was one of the
rare moments, and it just
happened a week ago, where
it all came full circle.
And it felt like, yeah, that
was 100 percent worth it.
But I'm curious how When we're
making these decisions, like
making the sacrifices, et
cetera, when and if we get
to a point where we get to
have that, that assessment
of, was it worth it?
So I think it'd be kind of cool
if you and I did it now, right.
In, in real time and look
back, what wasn't worth
it and what was worth it.
What were the costs?
And yeah, yeah, no,
it's, it's interesting.
And I think, you know, it's,
it's, it's fortunate when we
do get to have these moments
where that reflection comes
back and does sort of say
like, you know, taking on
the whole, it was worth it.
Right now.
Here's what's
really interesting.
If you had asked 22 year old
will like, right, you're going
to spend the next 30 years of
your life to achieve a moment.
Here's the moment.
Would you have gone?
Hell yeah, I'm
signing up for that.
So that's, I think that's the
other thing that's interesting
is that some of this, like
some of the value in that
moment you had with summer.
Came from all of the sacrifices
came from the things that were
and weren't worth it, right?
Yeah, it wasn't like I was going
through hardship and working
all those hours so that one
day I could you know Have my 13
year old daughter say thank you
Yeah,
but on the other hand There
was a part of me when I
was sacrificing all of this
stuff That hoped like hell
there would be a payout.
Yeah No, I think but that's
I think that's what's so
interesting about it in some
cases is that that the payout
Is amorphous or it's not what
we thought it was going to be.
Right.
The payout is the house and
the Lambo and the whatever.
Right.
Yeah.
Right.
Right.
Those things happen and they
go away and you're like, well,
okay, those did make me happy
for a minute or two or five
years or whatever it was.
Yeah, but it
wasn't the payoff that I needed.
It wasn't the thing that made
me feel like it was worth it.
Those felt like
transactionally worth it.
There was a bit of a
give back, but it didn't
feel like a full payback.
You know, I, I get these
moments a couple times a year.
It feels like at this
point where something
happens in life, right?
Often comes from, from my wife
or reflective moment where
we're together, uh, where
it's, it's coming out of one
of these moments where like.
Life either feels like
really great and we're
super happy for it.
Like you're just sitting there
and you're just looking around.
You're like, you know what,
things are doing what they're
supposed to be doing or what we
would hope that they would do.
Like we're getting what we
want right now out of life.
And this feels good.
And, and there's moments
of gratitude will come.
Like some of them are internal
for me and those feel great.
Sometimes it's just her
like turning to me and
saying like, you know what?
Thank you for what you've built.
This is, this is amazing.
Like we're, we, you know,
we wouldn't be doing
this without you clearly.
Other times it's actually
in moments of hardship.
Where this all also
feels worth it.
All right, because and we've
talked about this before too,
which is like the ability
to navigate and survive
some of these disasters
that life throws at us.
Like one of the things
that I learned by living a
life of disaster for a long
time, building companies is
that you can survive them.
You can get through them.
Right.
So when I think back and
reflect on moments like when
my father had his stroke
and that was an extremely
difficult life, but like.
I was really grateful that
not only I had the resilience
and and the patience and the
fortitude and the resources to
do it, but patience from people
like you right and all of this
other stuff like this support
that I needed that wasn't
just taken for granted and and
wasn't just there by default.
Right.
Other sacrifices we made that
said in this moment, now you
can, you can have some, you
can have some payback for this.
That made it worth
it.
Let's break this into,
let's start with the things
that weren't worth it.
Yeah.
Right.
Uh, because I, I think that
things either we couldn't get
back or we wish we could go back
in time and change, et cetera.
I think a lot about
it in terms of like.
Missed experiences, and I think
everybody has missed experiences
by, by definition, but these
were very intentionally
missed experiences.
Like the, the first thing
that comes to mind is I didn't
have a college experience.
I went to a college.
Yeah.
Right?
I took classes.
I had nothing.
I, I don't have a single moment
where I was walking across the
quad and just got involved in
a spontaneous volleyball game.
Right?
Right.
That happened never for me.
I didn't play beer
pong until I was 36 years old.
Like, late in the
career for that one.
I talked to
so many people that
like, that pine about how
incredible college was.
Here's what I
remember of college.
I remember not
getting into college.
I remember being forced to go
to college, self inflicted, on
the weekends full time, while
working two full time jobs.
And I remember like, college
was a thing that existed.
While I was working, it was just
getting in the way of working.
Right?
I started my company
when I was 19.
So really throughout my
entire college career.
I had a very full time job in
then some like classes were
just something that I had to
ghost To because I was still
paying for this thing called
college and I had no idea that
I was going to build a company
You know, in other words that
I was gonna work all of the
fun parts that people talk
about like spring breaks I've
never went on a spring break.
They don't occur to me In fact,
I spent my first spring break
learning to code right like
hold up in the graduate dorms
I had nowhere else to live
Now, when you look back on,
let's start with college just
because that's a seminal moment.
What
do you remember?
What is it to you?
Oh, a lot of the same things.
Like I remember like one of
my, one of my happiest college
moments actually was figuring
out that I could cheat the
system a little bit because,
uh, you know, the university
we went to had a cap on,
had a cap on credit hours.
And kind of like you at that
point, I was, I was in a
position where like, I felt
like University was kind of
getting in the way of this
other thing that I was doing.
Yeah.
I had committed to it.
Everybody expected
that I'd do it.
Yeah.
And all the advice I was getting
from the people around me was
that you should keep doing that.
You shouldn't, shouldn't
sacrifice that.
Okay.
I'll keep doing it.
But I figured out that I could
go and take some of these, like.
general curriculum
nonsense classes at a
community college nearby.
And
ergo, like I could get
to 30 credit hours.
You're only allowed
to have 20, I think.
And I could get to 30.
Right.
So my, one of my crowning
college moments, my happiest
moments in university was
when I figured out I could
kill myself a little faster by
adding more of a class load.
But you know, what was
cool about that, man?
One of the things that like, it
definitely taught me something.
It cost me to definitely
cost me, but it gained
this, this thing that I
realized, like there's a
superpower that I can like.
Go into hyper focus mode by
virtue of not having any time
doing anything else with 30
credit hours and a business.
I didn't have a single moment
to screw around, which was cool.
Because I crushed those, those
semesters, like great grades,
great business outcomes.
What did I lose?
Well, like girlfriends
were kind of tough.
Um, you know, shooting pool with
my friends was kind of tough.
Uh, doing anything like, and
having any kind of fun, like
going to, going to parties.
I also distinctly remember
this moment, uh, in, in like
my, my junior year where
three good friends of mine.
What one of whom was a roommate
were talking about this party
they were going to that I
hadn't even heard about and
all of a sudden I realized
I'm not even getting invited
anymore you're not even there
not even there literally you're
I am I am a ghost that pays
a higher proportion of the
rent because I had started to
use their house as my office.
Um, so by virtue of taking
over 80 percent of the
household, I started paying
80 percent of the rent.
And so, yeah, there
were just a ton, right?
Like spring breaks
weren't a thing.
Um, I, I, I, I remember,
oh my God, uh, I won't name
the company, uh, local,
local Columbus company.
Well, you may know them.
We had built something pretty
significant for them and then
it broke and I spent, I spent.
finals week.
Yeah.
And then spring break.
Yep.
Trying to fix that shit.
And it, that was one of those
points where when we say like
it nearly killed us, I mean,
like it nearly killed me.
I was, I was
exhausted afterwards.
I was a ball of anxiety.
Yeah.
So there were, there were a
lot of missed experiences.
Let me build on that.
So let's, let's say college
was wiped off the map.
Yeah.
College, what was college?
I have a degree
that said I went.
Yeah, right, right.
I do not.
For a lot of people who
had phenomenal college
experiences, you know, got
to go on the spring breaks,
the big trips, the gap years,
etc. The idea of that just
being deleted from their
history sounds insane, right?
So again, when I say not
worth it, I almost think it's
more not worth it, you know,
to have lost that experience
to people who had it.
I never had it, so it's
hard to say that, you know,
what it would have been.
Um, I just know that
I didn't have it.
If I fast forward a few years
later, I'm like 25, right?
And now we have hundreds
and hundreds of employees.
And one day, and mind you,
like, I'm 25, but like, maturity
wise, imagine you're maturing
at different thresholds.
In different ways.
From a business standpoint, I
had matured extremely quickly.
But I was still a
25 year old kid.
Right, so emotional
maturity, right?
Emotional maturity was
far from that, okay?
I still had no
worldview whatsoever.
So let me give you an example.
One day, I'm talking to one
of my new employees, and
he's like, he's an old guy.
He's gotta be like 38.
And he's talking, um, about
how Right, right, right.
He's talking about how
he's so excited that he
just got a, you know, a new
promotion with our company.
And that it means that his,
uh, that they'll be able to
cover more of his daughter's
expense for college.
And, I know that sounds like
a weird, like, moment in
time for something to occur
to you, but I was like,
whoa, hold on a second.
Like, your job here is going
to pay for someone else's
college, or more specifically,
if you lose this job, your
daughter can't go to college?
Yeah.
I'm responsible for
that?
Yeah, thanks for the weight
on the shoulders there, pal.
Like,
yeah, like, I know it sounds
dumb, and eventually every,
something has to occur
to you for the first time
every time, and that was it.
And I remember, Like just
feeling this crushing
weight at 25, like, like
at 25 you have problems.
But you don't have crushing
weight of responsibility
problems, right?
Now, everybody's crushing
weight and everybody's
pain is their own.
So, if your crushing weight is,
and I don't mean to downplay
this, but if your crushing
weight is you're a developer
and you have to ship code, and
your boss is an a hole, right?
I get that, right?
I'm just saying, like,
I was responsible for an
awful lot of people, and I
was like, whoa, and I had a
hard time dealing with that.
At the same time, okay, this
is around the same year,
I decided that I wanted to
build like a, um, a network, a
local network, of other people
in the technology business.
Back then, there was
no LinkedIn, there was
no, you know, whatever.
I picked up a local paper,
Business First, if you remember,
and I looked at some lists
they had created of all the
companies that were like the
top technology companies of
Columbus, Ohio, of like 1998 or
whatever the time period was.
And I did a weird thing.
I called every single
one of those people.
Like, I would call the main
line of the company, I would
get transferred to that
person, and I'd be like,
Hey, I'm Will Schroeder, you
have no idea who I am, but
I'm in technology, you're in
technology, would you like to
come to my house for a drink?
I can't imagine if someone
called me, and I guess I'd
be cooler about it, but like,
it was a very random call.
Within the first year, these
events that I was doing
had like 200 CEOs at them,
CEOs and, um, CTOs, okay?
Of all companies and all
connected in all different
ways, like a huge guest list.
The reason I'm bringing this up
is because the average age in
that room was like 48 years old.
And then there was me, who
still had pimples, right?
And I remember thinking like,
this isn't how a 25 year
old is supposed to live.
Right, yeah.
Right?
I'm now recreating the
college parties that I missed,
but in the most absolutely
bizarre way possible.
There's
really old men!
There's almost old dudes.
Um, and that's how
I met Elliot's dad.
Oh,
wow.
That's funny.
Yeah, yeah, yeah.
It makes sense.
I met his dad sitting in
my, he was sitting in my
living room, and I met him
10 years before I met Elliot.
And, uh, but my point is,
that party makes absolute
sense for me at 50.
Yeah.
But at 25, ironically, I
would have never gotten
invited to that party.
It doesn't even make
half as much sense at 25.
Right?
It doesn't.
But what I'm saying is that
period of my life where
it should have been spent
going to other parties or
doing other things, right?
I had this bizarre life
where I was living like
a 50 year old man at 25.
Same conversations, the same
weights, etc. Meaning I never
got to have the carefree 20s.
I was always saddled
with a massive weight of
having to live a different
life at a different time.
It'd be like having
kids when you were 8.
Right.
Right?
Like it just didn't make sense.
You get
it.
Sometimes I feel like my
emotional maturity was
probably around 8 when
I had my first kids.
It's super interesting too
because I unsaddled myself
with the business right at
the time I was graduating.
But what was super interesting
about it was Then did I go
back and recreate all of that?
Did I go wild out?
Like I'm free?
No.
What did I do
right back into it?
Right.
We walked straight back in, but
saddled myself with bigger and
different responsibilities now
on an international stage where
we're building stuff across
borders with teams that I talk
about emotional maturity being
low and worldview being low.
Now I'm spreading this
lack of knowledge across
multiple cultures, which
always makes it easier.
All right.
So it was, it was super
interesting to me, kind of the
point you were making before.
It's like, we didn't know
what we had lost, right?
Like if we were to go back
and we're to take like
one of our friends and say
like, I'm going to delete
your college experiences.
Yeah, it's a very different
human, but we didn't have
those to kind of compare to.
And so it didn't even occur to
me at the time, it was like,
Oh, now I could take a beat.
I could pause a bit and
I could go back and I
could maybe do something.
I can't really, can't really get
most of the stuff back, but I
didn't even have that reaction.
It wasn't like, okay,
now I'm unsaddled.
Let me run wild a little bit.
No, it was like, I'm unsaddled.
I feel naked.
Where's the next saddle?
Yeah, it's interesting
because all of my habits got
built based on that, right?
Like, uh, I've never had a
couple months off where I
didn't have a job, right?
You know, I was in
between, now I get it.
That's also stressful.
I'm saying it, I'd never had a
moment where a work wasn't like
absolutely the priority, right?
Ever, like ever, ever,
ever, ever, ever.
There's been not one second
where it's ever been the case
and it doesn't occur to me.
That you can't just be
permanently stressed about that.
Like, that is my baseline.
Like, the anxiety that comes
with knowing that on any given
day something can go wrong.
Like, exponentially wrong.
I don't just mean life wrong.
I mean, we all have that.
But I've never had the, yeah,
if I just show up at my job,
I'll get, keep getting paid
unless I fuck something up.
Right?
I've never had that.
I'm not saying it
wasn't worth it.
I'm saying, but
I never had that.
Right?
That I'm sure.
Yeah, for sure.
No, but I think that's
an important, kind of an
interesting transition there.
So, you know, we talked about
missed experiences, but let's
talk about then kind of like.
This definitely carved some
stuff in stone into our, into
our habits, our personalities,
our psyche, our bodies, right?
Like, and in fact, I think in
this category, because again,
like some of the experience
I look back on and I go like,
had I gone to 20 frat parties,
wouldn't my life be measurably
different or better now?
I don't know.
I, I honestly don't know.
Right.
Like there are, there
are fun stories.
Like I get together with some
of my friends and they're
like, no time when so and so
pulled the tree out of, uh, you
know, going across the quad.
I'm like, no, I don't actually,
but only by, by secondhand.
So, but there are other things
where like that we did or
were done to us that I think.
We could arguably say
we're, we're significantly
like less worth it.
Right.
The fact that at, at
21 years old, I think
I've shared the story.
I know you have
shared it with you.
Well, I don't know if I've
shared on the podcast before my
business cell phone, super sweet
Motorola star tech, uh, by the
way, when that thing would ring,
I would immediately get tired.
Yeah.
Didn't know that that was an
anxiety response and depression.
My phone would ring and
immediately when I say tired,
I wasn't like, Oh, I don't
feel like answering that.
I mean like nearly passing out.
Yeah.
It's an
anxiety response, right?
Like I was like, what is
the fainting goats when
you clap your hands?
It falls over.
My phone rings, Ryan falls over.
Why?
Because of so much
stress that came through
that tiny little age.
Yeah.
I think about, like, uh,
the habits that, that
were ingrained in me.
Yeah.
Um, but not good habits, okay?
Nothing where you can say, Well,
you're disciplined and you're
a bit Yeah, fuck all that.
No.
This is not that.
No.
No.
Like, I have hard coded
into my psyche two modes.
I'm either working
or I'm guilty.
I've never been not working
and also not felt guilty
unless there was some condition
where I couldn't possibly
Be reasonably working.
For example, like I
was I was coming out of
surgery Or it's Christmas.
All right, like in in either
case and I've worked through
Christmas before I'm not proud
of that But my point is that
it built, you know, when I
talk about things not worth
it, it built a psyche that
made it Conditionally hard.
Yes for me to enjoy
free time Without guilt,
without guilt.
And again, I get it.
You're like, Oh, you should
see a therapist, but I get it.
Like I understand why it exists,
but it's existed for 30 years.
Right.
And like, there's a whole
bunch of reasons for that,
but that was, that's a
lot of mental weight to
permanently carry and it all
stems from entrepreneurship.
Yeah, it does.
And I think that's one of the,
the, the big dangers there was
that again, there's always this
weird, well, not always, if
you have some success, there's
always this weird mix of, well,
I got that because of this.
Right.
And so there's this,
Justification of some of
these, these bad behaviors,
some of which were just, you
know, byproducts of all the
action activity that we were
engaged in, but you don't
even think about changing
them like it didn't even
occur to me that maybe these
things aren't healthy, right?
I think it's part of the
reason like where, as we came
through that period where all
of a sudden millennials were
flooding the workforce and now
we've gone on and on and on.
And there's a lot more
discussion around like,
you know, workplace
health and behaviors and
cultures and all this.
And I think in the
beginning, You and I
were kind of like, what,
like,
what
do you mean?
Like we should
lead with purpose.
Like, what is that?
Like, didn't we just getting
some shit done right now?
Like we just hammered
through this.
Yeah.
That sounds disgusting.
Yeah.
Right.
Kind of lazy trope.
Is that right?
And again, we're
laughing about it.
Just so folks are listening.
We're laughing because we
understood poorly programmed.
We were, I was rewarded for
decades for hurting myself.
Right.
Like, and I was proud of it.
When I would say, hey guys,
uh, can't come to work because
I've worked so hard that
I'm sick, I was like, oh,
now I have justification for
not working as much because
now I'm laying in bed, sis.
When I say proud of it, that's,
that's a perverted term to say
it, but like, I felt justified.
Like, I felt justified
in taking time off.
Like, for a good 20 years,
it would never occur to
me to just take a day off
because I felt like it.
Yeah, just because he felt like
it, but like, think about it.
Well, you and I spend 95 percent
of our time together working
the 5 percent of the time
where you and I are like, Hey,
let's do something leisurely.
What do we do?
We go into a workshop.
We build things.
We mulched your
yard once, right?
Like even, even when we're
like, let's go leisure.
What should leisure look like?
How about hard labor?
Yeah, that sounds right.
Right.
That we don't need to
feel guilty about it.
And we can still have some fun.
That was
me today.
Right?
You know, you and I talked about
it, like, so, I get up at 4am
this morning, and I always get
up at 4am, and my planning for
my day is how I can squeeze in
enough work between my work.
You know, so I'm, I'm, I'm
building a house, and like,
I'm not even kidding, like,
my, my thought process this
morning, as soon as I wake up
was, okay, sunrise is at 7.
30am, so if I can get to
the construction site,
uh, my house before 7.
30, if I leave my house at 7,
I'll get there exactly at, at
daybreak, so that I can start.
Doing work, but before
that, since I'm going to
have a couple extra hours,
like between four and seven
daybreak.
Yeah,
I'm like, okay, I can get
at least an hour, an hour
and a half of like all my
busy work for startups.
com, uh, knocked out.
Then I can go into my
workshop and I can build a
bunch of stuff that I could
then take to the job site.
And then, no, this is the
best part though, while
I'm at the job site.
Right?
This is this morning.
I'm sitting in my Bobcat
skid steer, moving earth.
Right?
I'm literally, like,
like, uh, shoveling earth
all over the jobsite.
And it's like, 8.
15. Uh huh.
And while I'm trying to operate
this heavy machinery, I'm
checking my slack to make sure
there's nothing I'm missing.
Right?
You know when they say don't
take medicine, uh, if you're
gonna operate heavy machinery?
This is what they're talking
about, like specifically
this kind of stuff.
And I'm thinking to myself,
if I end up dying like
this, Ha, ha, ha, ha!
This would be so poetic, right?
Well, you
would have been
proud of yourself.
Pecking work while
he was working.
But, but my point is, The reason
I was checking my phone, and
mind you, as you know, we don't
get started, like, technically,
officially, until 9am.
The reason I was
checking my phone at 8.
15, while I'm operating
heavy machinery, is because
I felt guilty that I might
not be present for someone
else at work, in case they
had a question before ours.
Right.
Which makes no sense, but
that is my default condition.
That is how I'm programmed.
Yeah.
Yeah.
That came from that period.
We just did daylight
savings, right?
Last, uh, couple
days ago, right?
We don't do that here.
And so now you guys are
two hours ahead of me.
So like when I wake up at
5 o'clock in the morning,
one of the very first
things I do is check.
Does anybody need me?
Right.
There it is.
Does anybody really, really
need me in that, in that regard?
Probably not generally
not equal to good enough
business and stable enough
and have good teams.
And yet, because going back
to 21 year old Ryan who falls
asleep when his phone rings.
Because that's probably
something really serious,
like you, it's, it's
hard to shake this stuff.
You know, something that's
really funny about everything
we talk about here, is
that none of it is new.
Everything you're dealing
with right now has been done
a thousand times before you.
Which means the answer
already exists, you
may just not know it.
But that's okay.
That's kind of what
we're here to do.
We talk about this stuff on
the show, but we actually
solve these problems
all day long at groups.
startups.
com.
So if any of this sounds
familiar, stop guessing
about what to do.
Let us just give you the answers
to the test and be done with it.
And so when we talk about, you
know, the cost, you know, when
I say things not worth it, you
can, you know, I don't know if I
want to say not worth it to put
it against the justification,
but if you talk about the hard
coded costs of what it took
to do what we do, you know,
going back to that story with
my daughter, that they weren't
insignificant in when people
look at the outcomes, they're
like, Hey, you're running a
successful business, or maybe
you have some nice stuff or,
you know, something like that.
They only look at the outcome.
They don't look at
everything behind
it.
That's why, like, I kind of
joke when I say this, and I say,
show me any successful founder
and I'll show you somebody
in need of deep therapy.
Yeah, right.
Because, like, you don't
get there, right, without a
significant amount of sacrifice.
Hey, Will, what's the
name of our podcast?
Yeah, Startup Therapy, yeah.
Ah, why did we pick that?
Yeah, yeah, pretty
specific, right?
So, okay, we definitely got into
the tough parts, why it wasn't.
Let's talk about.
What was worth it?
What were the sacrifices
or what were the outcomes
for those sacrifices that
honestly, you know, everything
we just said, like not taking
care of ourselves or missed
experiences, et cetera, the
worth it was so worth it.
That we do it again, we
would take on that level of
pain and suffering again,
because we got these things.
What comes to mind that
where you go, honestly,
this part was worth it.
Yeah, look, I think you
and I both have talked
about this before, and
we agree on this one.
It's, it's the freedom,
it's the flexibility.
Yeah,
yeah.
Like, I had one of those little
moments of gratitude, today,
Tuesday, Monday, yesterday.
Jack, my seven year old,
comes home from school.
Pops into my office, happy
as can be, got something
he wants to show me, pulls
it out of his backpack.
Before he does, he stops
and he goes, Dad, I'm glad
you're home when I get home.
That's cool.
I thought, you know what?
Me too, buddy.
Me too.
Right?
And I don't take
that for granted.
Now, there are other
ways of achieving that.
Right?
So I think one of the important
things that we should point out
here is the sacrifices you and
I made are not necessarily only
specific to entrepreneurship.
Right?
I know doctors, lawyers,
other people who have done.
Oh yeah.
Sacrifices.
Universal sacrifice everywhere.
Parents.
Neither are the benefits, right?
There are other ways.
You can have a remote work
job and get exactly what
I got with Jack yesterday.
But this is one of,
one of the things that
has come out of this.
So like for me, it's been
freedom at a lot of levels.
All right, which is, you know,
some of it is control, right?
So it is being able to say,
like, I define certain things.
Like, while all of my friends
were out trying to have the
right haircut, which was a crew
cut at the time, to be able to
get hired by Procter Gamble,
coming out of business school.
Literally, there was like
a haircut you had to have.
And I was building things
my way and defining my
path, what I wanted to do.
I had control.
Nobody could take
that away from me.
I liked that.
Some of it is beyond control.
Actually, some of it is being
able to be A little out of
control at times, right?
The freedom to do that when, and
when, and where it's necessary.
And you know, like for me, the
life design has been a huge
part of, of what's, what's
occupied kind of my, my forties.
And trying to figure out, like,
now that we've done all this
stuff, like, how do we start to,
A, repair the body, repair the
psyche, uh, make sure that, you
know, that the time with family
is as high quality as it can be.
In my case, that's
involved, like, moving
all over the world, right?
Which is about to happen again.
We're getting ready to
change hemispheres once more.
And so, I think for me,
the freedom is probably the
one at the very, very top.
Yeah, and I think, uh, when we
say freedom, freedom means so
many things to so many different
people and a lot of it has to do
with where you came from before
that freedom, to appreciate
what that freedom means to you.
Some people may say, hey,
I just wanted, you know,
financial freedom from my
parents, and I get that.
Again, everybody's
journey is their own.
Mine was, I just want to be able
to do whatever I want to do.
At any given moment.
Now, if you can see, most of
that involves work anyway.
But that, that's
also part of it.
Like, I want to be able to work
on whatever I want to work on
at any given possible moment.
In, you know, this podcast
is a reflection of that.
We've been doing this for
what, five, six years?
And it's been a long time.
More.
We're in our
seventh year of this
podcast.
Whoa!
I didn't even know that.
I actually just
guessed at the number.
Also, for all the, those
of you that have been
listening to us for at
least that long, thank you.
Thank you.
Much appreciated.
Thank you all.
Uh, yes, but, um, but that said,
it's in that time, you know,
we've been able to do all kinds
of, of different things and
the podcast was one of them,
the podcast, I always say, and
we had a boss, they would have
made us stop doing it, right?
100 percent
Right?
Like, the ROI on
this is terrible.
Yeah, right,
right.
What's interesting about the
ROI on it, on this podcast
for folks that are, that
are listening is whenever
someone comes to me, and I
know you feel the same way,
And they're like, dude, I've
been listening to your podcast
now for like, you know, since
the beginning of hundreds of
episodes, I'm blown away by it.
And I know you are too,
but that's the ROI.
Yeah.
I'm like, we got to sit
down with somebody, let them
inside our heads in a very
vulnerable way, but also,
you know, get to hopefully
validate some of the things
that they're going through.
Every time we get one of those
emails, tweets, whatever it
is that speaks to that, like
it's again, it's that five
seconds of gratitude that
made the seven years worth it.
A
hundred percent.
And so our freedom couldn't
control our day for me to be
able to do that for me to be
able to, um, sit down with
you every week and be able to
share these ideas and kind of,
you know, what's going on in
our lives and just do whatever
the hell we want with it is.
Now that's just one tiny
bit of a bigger mosaic,
but it's, it's kind of what
this freedom is for me.
Whenever I didn't want to
do something, no matter
what the consequence was,
I just stopped doing it.
Now, sometimes that costs
me millions of dollars,
you know, lost revenue.
Right.
But honestly, worth it.
Totally worth it.
Right.
Like if I had the decision to
do, I do it exactly the same.
And I say that because having
the agency and the freedom,
To be able to operate, wake
up in the morning and say,
this is what I want to do.
This morning I wanted to
go operate a skid steer
and move earth, right?
Like, that's what
I wanted to do.
And knowing that there's
no reason that I can't.
Let me separate, there's
no authority to tell me
that I can't, like an
actual, you can't do this.
Now, maybe a whole reasons
why I shouldn't from running,
uh, killing myself in the
skids to yours, whatever else.
So be it, but no one's there
to say that I can't, and I
think that's, that's so, that
is by far top of my list and
there's barely a number two.
And what was interesting to
me around this freedom, right,
you know, that you and I were
able to create in our lives,
is that It didn't cost much.
A lot of people think freedom
as I sell for 10, 10 million.
And, you know, I get 10 million
and I never have to work in.
Yes.
That is a level.
It is a level of freedom.
Yeah.
It's not the level of freedom.
My freedom came at 19
when I started a company.
Same.
Now, granted, I was getting
paid nearly nothing at the
time, but I also didn't really
have that much in expenses.
We were getting paid, we were
just getting paid in different
ways, and I'm not talking
about the Damon's Ribs that you
got, or the massive tab that
Victorians Midnight Cafe gave
me in return for their website.
I'm talking about the
unlocks they gave us, man.
I, to me That period in time,
yeah, there was cash at the end
of that business when I sold and
that was great and I got to pay
off a bunch of friends and they
got to pay off student loans
and all sorts of cool stuff.
But man, the thing that I
got handed that during that
period that made it all
worth it was that key on it.
It was the freedom, but
it was the key that said
agency on it, right?
Where I now knew I
can go do a thing.
I can do it on my terms
and I can find a way to
make it work and yeah.
Did I have other friends
who were making more money
than I was at that point?
All right, they all, they
wouldn't, they wouldn't
got good jobs at top three
consulting firms or whatever.
And we're making good cash
in this first couple of years
where I was just sacrificing.
But it, that didn't,
didn't bother me.
Right?
Like, and ultimately I've,
it's worked out to where I'm
happy doing what I'm doing.
I've had three different cases
that come to mind as I'm just
brainstorming top of mind where
I had an opportunity to make
essentially more money at a job.
Then I could have doing
the startup that I
was doing at the time.
And as I recall them, uh,
the first one was essentially
my first company where
we're going to get, uh, uh,
bought out and we're gonna
take the company public.
And essentially, you know,
you're working for the
stockholders at that point.
And, and I would have
made exponentially
more money doing that.
I wasn't even 1 percent
excited about it.
Here's somebody saying here's
untold fortunes that you
can make and you were in a
position to make them But you
have to accept this you have
to accept Hierarchy and I was
like nope not even 1 percent
interested and I bailed and
I'm proud of that another case
This is random where someone
who didn't know what I was
doing at the time, right?
This is after we'd sold the
agency offered me a C level
job, like a CEO level job,
making a ridiculous salary.
And I was like, and again, they
didn't, they didn't understand
where I was at the time.
And I was, I appreciated
the fact that they offered.
And I thought to myself,
man, I could do this
job standing on my head.
I could make like
just gobs of money.
It was a seven
figure offer, right?
Like I could make gobs
of money, not work crazy
hours and all these things.
And I was like, I can't
think of anything I'd
want to do less because
it involved having a boss.
And the boss
might've been great.
Right, for all I know.
I don't, you know,
dislike people.
I just, I wasn't doing
it because what I got,
I was getting paid.
I was doing it because
I wanted the freedom.
You know, here's the irony.
I'll take the freedom of doing
whatever I want and get zero
dollars over any level of
control over any level of money.
If you said I'll pay you 10x
more than you're making now,
like whatever you're making.
I had a friend of mine, I
won't say his name because
it's not fair because he shared
this with me in confidence.
But he got offered a million
dollars to go take over an
internet company as the CEO
and he's a great guy Uh, he's a
previous entrepreneur himself.
Okay, and one day we're sitting
in his office at at this
company I said I gotta ask man.
Like why'd you take this job?
Right.
Like you're an entrepreneur,
like it's what you do.
And he's like, I hate risk.
I was like, bro, literally
you're an entrepreneur.
I mean, cause he had started
and sold two companies.
Right.
And he's like, I
can't stand risk.
He's like, I can take down
a seven figure salary plus
bonuses and stuff like that
at a very high profile job
and not think about it, right.
I'm just going to get paid.
I don't have to worry about it.
And we paid a lot.
And I was like, damn,
it would never even
occur to me to do that.
To do that.
Yeah.
I don't even have those gears.
You know what I mean?
Once you have freedom,
it's, it's a hard thing.
Now I think in, you know,
everybody's going to have
different mileage in this stuff.
In his case, freedom
wasn't free, right?
Freedom came with the
shackles of risk and the
fear of the risk, right?
It's not really the risk, right?
It's the fear of the
outcome of risk, right?
Like risk itself
doesn't matter, right?
It's, it's what, it's what
happens in their side of it.
So I get it.
I get it.
But interesting though.
So I'm thinking now in
hindsight, I can go back and
I sort of know that it was at
that moment at 18, wandering
the halls of university where
the chance encounter led
to me starting a business.
And that was where
freedom started.
Well, in my case, I
think freedom started a
little bit before that.
We'll, we'll dig into it, but
I don't know that I realized
that, like, I realized that
that was the moment of freedom.
When was the first
time, do you remember?
And I'm struggling now to do it.
Do you remember the first
time you realized you had
the freedom, not, not in
hindsight, but in that moment
where you're like, I'm free.
I, do you remember that?
I don't, I don't either.
No, it
wasn't like, uh, there
wasn't like a seminal
moment where I was like,
Oh my God, I'm now free.
Yeah.
I do remember like early in my
career, there was moments where
I'm like, I'm going to otherwise
have to look for a job.
Yeah.
And
that sounds terrifying.
Not just the job search,
but the idea of being put
into a corporate machine.
Sure.
For a lot of the folks
that, that have worked
here at startups.
com cause we tend to.
Sell the idea of being free.
If they leave here,
you know, two paths.
A lot of the folks that
leave here, leave here
to start something new.
Which is kind of our goal.
That is the ultimate, like,
If you leave here and you
start something new, you have
graduated from this company.
Yeah, nothing feels better.
Exactly, it's exactly what
we'd love to see you do.
Now that doesn't mean that if
you leave here and take a job
that you failed in some way.
But when folks leave here and
they take a job somewhere,
It's always very begrudgingly.
Yeah.
Right?
It almost feels like,
Ugh, I gotta take a job.
In the same way that founders,
when things don't go well,
and they gotta go take a
job, they do it begrudgingly.
Even when the job pays a ton of
money, especially, or pays any
money, just pays money, right?
Because you weren't
getting paid before.
It was like a step back,
yeah.
Yeah, yeah, yeah.
I hear this from founders
constantly that have
gone through this.
They're a year into job,
whatever it is, from
where they were, and
they're always miserable.
They're always lamenting.
Now the first six months,
they're over the moon.
Because they're like, I get paid
and I have health insurance.
This is amazing, right?
They forget what that means.
I took a vacation.
I didn't know what
that was anymore.
Right.
I get it.
But after a year or so, once
the pixie dust wears off and
they realize that they're
just a cog in a wheel,
it's impossible to put that
genie back in the bottle and
forget that, that existed.
We've had
so many of those conversations,
both from, you know, founders
that we know who've had to
go back to the J O B or for
people who've left and gone
on to a job, which of course,
like, they were excited about
when they didn't, right?
I think the begrudging piece
comes a little bit later.
Three to six months or
wherever the first performance
review was, or wherever the
first time like they didn't
get to do what they wanted
to go do, they realized
how much freedom they had.
Yeah, those, those conversations
have meant a lot, but like, I
think, you know, that's, that's
kind of another, another fun,
fun segue, uh, which is like.
That's one of the, the
things that have made
all of this worth it.
Right.
Yeah.
I'm watching people go to jobs
that they don't like, but the
impact that we've had unlocking
that door to freedom for so
many people, because the vast
majority of folks that we know
have not gone back to a JLB.
And they haven't gone back to,
you know, a typical career path.
They've gone on to start their
own stuff or they were already
starting their own stuff.
By the time we met them as
founders, we were talking
about employees or clients.
It's particularly interesting
for us because we both
help founders directly.
I mean, so we have a very
specific impact, like
of countless founders
that we've helped.
And then like we've watched
some of the founders or the
companies where we've had a hand
in their journey, you know, go
public or have a big outcome.
And it's like, damn, I keep
a spreadsheet of all the
people that have worked for
me for all the years that
have gone on to become CEOs.
And there's over a hundred
people in that spreadsheet.
That's wild.
It's crazy to think
about that, right?
Like a lot of people that have
worked for anyone at any given
time, they went on to become
VPs or they went on to become
CTOs or something like that.
And that's all awesome.
There's nothing wrong with that.
But I'm saying there's at least
a hundred people specifically
that specifically became CEOs.
Yeah, yeah.
And it makes sense.
They were sitting around going
like, well, shit, if we'll
can do it
far so low or so low.
But the reason I say that
is because I feel really
connected to that journey.
Yeah.
And and I'm 100 percent sure.
And almost every one of
those cases, if you ask them,
because I've actually had a
lot of these conversations,
they would say, I mapped back
that path to specifically
the time that I had with you.
Yeah.
Right.
And what I learned in
what you showed me, I was
capable of and et cetera.
Open doors.
Awesome.
Yeah.
That is awesome.
That doesn't mean I couldn't
have done that if I didn't
become an entrepreneur,
but like what I'm saying
is there, there are aspects
of what building your own
thing allows you to do that.
Like if I was VP of chase
bank, I just couldn't say that.
Like I just couldn't right now
you could say, well, if impact
was important, you wouldn't
have gone to chase bank.
Fair.
Right.
Yeah.
But there's no guarantee that
I would have a job that would
have exactly the impact I want.
Here, we get to design that.
Exactly.
You know, it's funny.
I'm going to, I'm going to
use a comparison that you
use a lot actually, which is
this, the difference between
Steve jobs and Tim cook, Tim
cook, super, super talented
CEO done great things.
Yep.
But like when you think about
the number of times, this is
pure anecdotal there, there I
could be way off empirically,
I might be absolutely wrong
here, but anecdotally.
The number of people that
you talk about, like having
been inspired by jobs,
built their own things
because of jobs, changed
their life because of jobs.
Versus the number of people
that you hear say that about
Tim Cook in, in my world.
Like again, maybe, maybe
there's an echo chamber that
I'm part of that I'm going
to wear out at this point,
but I know I'm part of some,
but it's interesting, right?
The, the impact
that that has, why?
Because he showed them
something different.
Like Tim Cook's an
excellent practitioner,
wonderful operator.
Right?
But jobs did something
different for people, right?
We do something different.
You can go work for Chase Bank.
Does that mean you'll
never start something?
No, but if you hang out with
the two of us, I'd say the
likelihood you're going to
go on to start something
goes up exponentially
versus, you know, working
for Doug and HR at Chase.
You know, I gotta say,
one thing I always take
off the table is wealth.
The reason I say that is like,
I'm very thankful and grateful
for, you know, the financial
opportunities that being an
entrepreneur has afforded me.
However, It's a dumb
way to make money.
I always tell you, like,
they're like, what's the
easiest way to make money, Ryan?
Get a job.
That's what they're
designed to do.
It's literally made just
for that transaction of
put work in, get money out.
Right?
Dead simple.
I was
like, this is the dumbest
way to get wealthy.
Um, and I'm not saying
that, like, obviously when
it works, it works, right?
It's the same way I feel.
Years ago, I used to
run a casting company,
uh, in Hollywood.
And we cast for
tons of shows on TV.
And I would get all these
people, you know, that would
come to our site that we're
trying to get on these shows.
Be like, well, should
I move to Hollywood?
You know, to become
famous, essentially.
And I was like, absolutely not!
Yeah.
I was like How are your barista
skills?
Yeah, exactly.
I was like, let me
put it this way.
If you don't move here,
you will never get cast.
Uh, uh, straight up, okay?
Yeah.
No one is sending their casting
director to Hoboken for talent.
Right.
Unless you're doing reality.
It's also the dumbest
way to build a career.
Because the probability that
it's going to end in anything
but being a barista, not
knocking baristas by the way,
is pretty much zero, right?
And so, when I think
about career path, or I'm
sorry, wealth path, this
is a dumb idea, right?
Now obviously when it
works, different story.
Actually, it's funny.
So today, uh, I'm on the
job site and there's tons of
people on the job site today.
Um, there's, there's
framers, there's, um,
electricians, whatever.
And one of the guys
comes up to me, okay?
And he has no idea
that it's my house.
Uh huh.
Right?
You're just the guy
that drives the Bobcat.
Yeah, exactly.
He has no idea I'm covered
in, in shit, right?
And so, he walks up to me and
we're just talking, right?
And he's like, man, I have
no idea what this guy does,
but this house is amazing.
Right.
And I'm like, yeah,
it's all right.
Right.
Yeah.
I just like totally blow it off.
I've worked on bigger.
Yeah.
Right.
Yeah.
Yeah.
But, but in his mind, he's
looking at this going,
it must all be worth it.
Yeah.
Right.
Because, because
this guy is a thing.
Right.
Like a big house.
Right.
Like a thing.
And I think to myself, like
the way you perceive that
outcome is that this guy
just started on day one.
He just did a lot of work every
day and just kept getting paid
and this was the final outcome.
Yeah.
Yeah.
As if it's guaranteed.
Right.
Now, to be fair, there are lots
of other jobs where it's not
guaranteed you're gonna become
like the next CEO like Tim Cook
did, but it's a fairly good
chance that if you continue on
this path, you'll wind up in a
very good financial position.
Yeah, yeah.
If you're a senior partner,
a managing partner at a law
firm, or a consulting firm,
etc. Now, if we had those
folks, oh my god, okay, uh,
let me give you this one.
A management consultant at
a big firm, okay, could be
accounting, could be McKinsey
style thing, that is 45 years
old and has made senior partner,
managing partner status.
Literally has no soul.
And, and by the way, I'm saying
because this person worked so
hard and sacrificed so much.
And Ryan, I saw the best,
one of the best ads I've
ever seen in my life, and
being a former ad guy, I have
so much respect for this.
It was getting off the
plane in, uh, LaGuardia.
Getting off the plane in
LaGuardia, this giant sign, like
mural, uh, I'm sorry, billboard
rather, right, that was on the
wall, was just a little kid.
I can't remember what
they were holding, like a
gift or something, okay?
And get this, the copy,
and you know I love copy,
the copy was, remember me?
Dude, are you kidding?
Right?
And then the bottom was
like, Boston Consulting,
I probably wasn't, but you
know, uh, Boston Consulting
Group, we keep you at home.
I was like, the most
genius placement, the
most genius
copy.
Yeah, because they're
talking to the people
getting off that plane.
Who probably don't, I mean,
of course they're being a
little hyperbolic, but not
by much.
That's exactly what, what
that person's worried about.
Now, the reason I bring
that up is cause I'm,
we're talking about, was
it worth it, et cetera.
At which point you've
chosen a career where that
ad makes sense to you.
That ad hits home.
You fucked up.
I'm saying it cost you something
and that is the ultimate cost.
So it is.
So I think this is the, but,
but go back to what you said
before, which is that, but at
least that came with, right?
At least that came with, I
mean, like, and not that it was
worth it, but again, but there
was like some certainty around
that financial path, right?
There wasn't that person
also didn't get paid.
Right.
Right.
I think this is one of those
things where like, when you look
back at some of the sacrifices
we made, Would I have been
unwilling to make them again
to get exactly what I got now?
No, I would do most
of the same things.
I think there are some
sacrifices that I made that
I didn't have to, and I
still could have gotten here.
I think that's where we have
to be a little careful, right?
We didn't know, we didn't
know, but I think that's
where like what part of what
we're trying to help people
do now is to understand
that like you should have a
life and a startup, right?
Because here's the thing,
the financial outcome
is not guaranteed.
The costs and
sacrifices are right.
Those are guaranteed.
Those come with the
territory, the outcome.
May or may not right.
I agree.
And so I think for us when
you know when we're looking
back on our own backgrounds or
folks that are listening and
whether they're kind of running
through this the same math.
I think the important thing to
know is like what you said that.
Yes, absolutely.
The costs are going to be
there, but you have to remember.
What would be worth it?
By the way, it's
usually not the money.
There has to be some heuristic
that you're optimizing for
that is more than money.
Because when it comes
back to it, that's what's
going to be worthwhile.
That's what you're
going to look back on.
It's going to be a kid that
says, hey dad, I'm so grateful,
etc. But it's going to be that
sense of Pride that you feel
that you, that you made those
sacrifices and it was worth it
without the cost of something
like seeing that goddamn
photo on the wall of that kid
saying, Hey, by the way, you
missed my entire childhood.
So for us as founders, we
do have to have a threshold,
whether it's worth it and if it
is go all in and at what point
it's costing you something more
than it's going to buy you.
Get the hell out because
it'll never be worth it.
No matter how much you make
overthinking your startup
because you're going it
alone, you don't have to.
And honestly you shouldn't
because instead you can learn
directly from peers who've
been in your shoes, connect
with bootstrap founders
and the advisors helping
them win in the startups.
com community, check
out the startups.
com community at www.
startups.
com to see if it's for you.
Could be just the
thing you need.
I hope to see you inside.