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.
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.
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.
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.
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.
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.
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.
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.