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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.
You've been an ad guy, a
member of a typist pool, a
salesperson, a carpenter.
Let's not forget, multi-time
startup founder, but like
in a world where, you know,
we were told like, pick
your path, pick your trade.
Go learn it and do it like.
How do we even end up
being founders, right?
And how does it that that like
somehow we keep running into
all these founders who are
like, well, but I don't feel
like I'm qualified for this.
Or I wanna do something
else, but this is
what I know how to do.
How do I reconcile that when
that is kind of how we got
here in the first place?
Right.
I agree it, it's fascinating
because fun fact, most of the
people that come to startups.com
that are starting whatever
company, a consumer products
company, enterprise, SaaS
company, you name it didn't
come from that industry.
You would think it would
be part and parcel.
Yep.
You would think like it'd be
10% or something like that.
But I wanna give like two
layers of abstraction for
the folks in the audience.
Number one, almost no
one was a founder before.
'cause that that actually
isn't a job that you just
get, it's when you create.
Yeah.
I'm gonna say that again.
A founder isn't a job you get.
No one gets the founder, no one
interviews for the founder job.
You create the job, which
means you always get hired.
I was just thinking about
like, how many times has
somebody had a headhunter
call them and be like, Hey,
we're looking for founders.
Right, right.
Exactly.
Exactly.
Ever.
So, but the second part
of that is because you
create the job, you are by
definition inventing yourself.
Yeah.
In, in most cases,
reinventing yourself.
Yeah.
Yet there's a massive
amount of, uh, pushback
that folks have on the idea
of reinventing themselves.
You know?
Sure.
You've got this kind of hard
coded feeling that we are
this one thing, you know,
I went to law school, I'm a
lawyer and that's what I am.
Yeah,
no, that's just
something you did.
I think what would be, what
would be fun today is to talk
about where this comes from.
This notion of I can only be
this one thing, uh, what it
takes to reinvent yourself to,
and we've done it many, many,
many, many times, even
with a single startup, like
within a single startup.
I think that's something
super important.
It's like how many times
have we had to morph and
evolve just because the
startup did so, right?
Like by nature we know like
if your startup pivoted.
Which a lot of them do.
You likely had to reinvent
yourself at that point to
survive the pivot because the
business completely changes.
Likelihood is you need to
change at least something
at that point, right?
Absolutely.
And, and I think what's
important to understand, and,
and I I I wanna make sure we get
into this, is every one of those
pivots, those changes, those,
you know, those reinventions.
Becomes part of a
bigger thing, right?
Becomes part of a bigger thing.
And we become this sort
of Swiss army knife of
capabilities and experiences.
And personally I embrace that.
I've got a list somewhere.
I, I'm gonna, I'm gonna see
if I can, I can bring it up
while we're doing our episode,
but I've got a list somewhere,
job role that I've ever had.
It is hilarious.
I made it for my daughter years
ago 'cause she was talking
about what she wanted to become
and I said, uh, give me a day.
'cause it would take me a
minute to, to reach out Uhhuh.
I'm gonna come back to
you with every job that
your father has had.
Yeah.
In his life.
And Ryan, I could, it
was like 50 things.
50. Yeah.
Yeah, yeah.
That's a thing though.
But that's, that is our resume.
Right?
Right.
And all of those things
come forward, right?
Like, yeah.
Are you a carpenter every day?
Well.
Right now.
Yes.
So bad example, but like you're
not a carpenter every day, but
you still bring your measure
twice, cut once mentality, the
tools, the things that you've
learned through that to what we
do at a, at a startup, right?
It's, it's all of these
things have their place.
We don't stop being one.
I think this is the thing
when people get really caught
up and scared about like
reinventing themselves, like
we have to stop being that.
You may stop doing that on
a daily basis, but you're
gonna stop being that person.
I will always have done those
things, and so that will
always be part of who I am.
I, I gotta share this list.
I'm not gonna go
through all of it.
I, I, I
hope a big part of me hopes
that you're actually just
gonna start singing That's
Life by Frank Sinatra.
And, and go through the, I've
been a poet, a pop, and, uh,
where I feel like this is
great.
This is in, in no particular
order, in this actual list.
I, I actually put all
the, the dates, stamps,
and where I did this.
Okay.
Uh, you, you ready for this?
I'm ready.
I'm gonna read it fast.
Commercial actor, podcast
host, what do you say?
Basketball coach,
high school teacher.
Telemarketer sandwich.
Chef parking lot.
Bouncer.
Casting director, college
lecturer, digital art,
museum curator, creative
director, database engineer.
Dungeon master hockey player.
Radio, dj, triathlete.
Uh, public company, board
member school mascot.
Head of business
development, BBS.
Cis Op dude are we go our
reality show, finalist, middle
school teacher, children's
book, art author Carpenter,
the CFO, nightclub owner,
receptionist president, SBA
young entrepreneur of the year.
Professional speaker.
RPG.
Game designer.
Yes.
3D, modeler architect, nightclub
promoter, interior designer,
general contractor, software
engineer, field hockey goalie.
And this list goes on.
I'm like.
I, I feel, based on, I, I
think you missed one, and
this is all very recent.
I a crash test, dummy.
I feel like with your luck
with vehicles lately that,
that you absolutely have been,
you've at least been doing
some engineering testing for a
couple of, uh, major companies.
Hey, by the way, you know what?
Didn't make that list.
I mean, it's on the list,
but I, you need to say it.
Founder?
Uh, yeah.
I, I was waiting for Yes.
Didn't hear it.
Yeah.
That was
without even saying like,
what you, what I can do
for a, forgot that one.
Yeah.
Parking lot.
Bouncer Rumor has
it, it was a Chuck E.
Cheese.
Is that accurate?
No, that was my first job.
My first job was, it was for
a pizza place in Connecticut.
They had a parking lot
situation where everybody
kept using their parking lot.
So the owner, uh, Leno
paid me like a few dollars
an hour to kick people
out of the parking lot.
Weren't supposed to
be parking there.
Amazing.
And I
was, I, I was like 12 years old
at the time, you know, trying
to, trying to be a bouncer and
knock people outta parking lots.
That, that,
that, there's some interesting
lessons learned there, I'm sure.
But let's talk about
reinventing yourself.
Yeah.
Okay.
Because every one of those
were jobs I had, mostly
jobs I got paid for, and
all of those required me
to have some learning or
expertise in order to have
those jobs and do those jobs.
But that's not even all of them.
Like I say, I only got like
halfway through the list.
Right, and And even I'm laughing
'cause I haven't looked at
that list in years, right?
I just brought it up right now.
I thought that
would be fun to see.
But it tells a story of how we
are both what we make ourselves,
but as importantly a composite.
All the things we try
and, and taste test and
absolutely get into.
But we're also not limited be,
I don't have like any, don't
be special capability that
anybody else doesn't have.
Right.
Like I'm just very
willing to try everything.
Yeah,
yeah.
To just say, 'cause I feel
like, I don't know Ryan, like
at some level, yes, I have the
identity of a founder, but to
me that's like saying I have
the identity of a creator.
Right.
It's what I create, what I find.
It's highly in specific.
Yeah, yeah.
Right.
It it just says directionally.
Yeah.
I like to build stuff.
When you think about yourself
and you think about some of
the different directions you've
gone, what are some of the
highlights that that come out?
You know, it's interesting.
I mean, the, in, in terms of
the directions I've gone, I
have to give that some more
thought in terms of like the,
the, the highlight reel there.
But there's an interesting thing
that I found and, and I think
it was like the point at which.
I started to want
to reinvent myself.
Were places where all of a
sudden I realized that like
it had become really familiar
and maybe safe as a result.
Like this, this sense
that like familiarity
equals safety, right?
Like I'm a lawyer, I'll
just always be a lawyer
and that's somehow safe.
And, and what I realized
was that it was just
sort of complacency
or wrapped in inertia.
And I didn't like that.
I didn't like that.
And so for me, there've been
these, like, these triggers
where it's like, if I haven't
been pushed or haven't had to
try something new, or haven't
failed at anything in a while,
like I get really uncomfortable.
I'm like, I get, I get
uncomfortable with the comfort.
It's like, okay, this has just
become commonplace, right?
Like, you know, the minute
I, I I, I master something
on relative basis, I'm
like, I'd like to move on.
I wanna try something else.
I think that's probably
part of the founder
ethos in, in general.
You know, I, I think what's
interesting is, um, a lot
of our career is shaped by
what we have exposure to.
Okay?
Yeah.
Yeah.
So, so let, let me give you just
a, a, a quick little vignette
that's always just inspired me.
Years and years ago when I was
pursuing one of my job titles,
which was board member of the
Rock and Roll Hall of Fame, um.
Super random people
like, wait, what?
Yeah, yeah.
They, they, they had recruited
me to become, to join the
board of the Rock and Roll
Hall of Fame in the, the
most fluke opportunity ever.
It made no sense for anybody.
But the reason I'm telling
you that is because as part
of the recruiting process,
they would give us tickets
to these private concerts.
So like when someone got
inducted into the Rock and
Roll Hall of Fame, there
was a public concert.
Yep.
There was also a
private concert.
A private show.
Yeah.
Yeah.
One of the inductions we
got to, to be at, which
was amazing, was Metallica.
Oh, wow.
It was unbelievable.
Right?
It's like 200 people in a
room and me and my wife,
like two idiots from Ohio.
Like, what, what
whatcha doing here?
Anyway, not the
point of the story.
So Lars Ulrich, who's,
uh, a phenomenal,
phenomenal drummer, right?
And, you know, just like a a,
a rock got in his own right.
Went to Julliard, by the way.
Yes.
Like, like not a, uh,
and I think they put out.
Classically trained rock God.
Yeah.
Yeah.
I was, but I think like,
like they put out their first
album, I think when they were
18, if my memory serves me.
Yeah.
Anyway, he's sitting up
there and he's like, kind of
teary-eyed and he's, he's giving
a speech directly to his parents
sitting in front of him and he
said, uh, you guys were always
playing music in the house,
uh, when I was growing up.
Right.
You made music a,
a part of things.
And Ryan, I, I always think
of you and your family
because I know there's music
in the house, et cetera.
I've got an anecdote I'll
share right after this that
just happened last night.
But here's what he said.
He said, mom and dad,
I'm here because of you.
Not everybody wants
to have their kid be a
drummer of all things.
Yeah.
You know, I've actually resisted
that one specifically
because it's strums
me too.
Right.
Me too.
Yeah.
And so he said, but I'm
here because of you.
And I remember when he was
giving that speech that like,
everyone's like teary eyed.
'cause like it was one of those
amazing things to turn to your
parents uhhuh and genuinely
thank them for the highest
achievement you've ever made.
Yeah.
Yeah.
Like it was incredible.
But.
Beyond that.
I just kept thinking as he
was saying it, I was like,
what if, what if his parents
were a bunch of dicks?
Yeah.
And they were like, no drumming.
Right, right.
You're gonna be coming.
Stop tapping on
stuff.
Lars, it noises shit outta me.
Like back to the Abacus and
like, yeah, but, but what
if his parents, you know,
again, talking about like
how we could become anything.
Yeah.
We're just like, no,
you're not a drummer.
Yeah.
Yeah.
You're an accountant And
I'm not, not an accountant,
but I'm just saying like.
But like if you can be
Lars or an accountant,
be Lars please.
Just like every time.
God's sake.
What was your vignette?
You said you had an idea.
Yeah, so last night and it's,
it's interesting 'cause it's
a nice illustration of this.
So yeah, we do a lot
of musical stuff.
The kids, the kids by and
large like to perform a
lot, but kind of to your
point, his parents weren't.
Stuffing drumsticks into
his hand either, right?
They weren't like you,
some drummer, right?
They weren't Tiger Wood's dad.
It was like, you will
play golf or die.
Uh, I think that's how it went.
I don't actually know.
He's probably a gray guy.
So last night for the very
first time ever, Jack decided
I was out playing piano and
the girls come out and were
singing a little bit as I was
playing, and then Jack shows up.
Now Jack loves to play piano
with me, loves to sit down.
He's, he's learned
to accompany me.
He's, he's seven
loves to accompany.
And then all of a
sudden he was like, dad.
You know, the song
that won the Eurovision
this year Wasted Love.
I was like, yeah, yeah.
Do you know it?
I'm like, no.
He's like, can you find it?
So we found it and we
started playing it.
He wanted to sing it.
He's never done this before,
but the girls love to sing.
My wife is amazing singer.
And so just like he all of a
sudden wanted to do this and we
have this beautiful, I, I will
share with you, I will not put
it out on, on broad social, but
I will share with you the, we
Nars just grabbed like a little
clip at the end of him singing.
It was so beautiful, but one of
the most beautiful parts of it
was she recorded this and dude
absolutely hits the notes at the
end, which like, I love that.
And it made me really proud.
What made me more proud was
the entire family erupted
into like just full on joy
at him hitting that note.
The girls, you hear the
girls in the background,
you hear me shouting,
you hear Nagas screaming
because he just crushed it.
It's such a cool thing
like that is now part of,
of Jack's fabric, right?
Like that is part of what he
was exposed to, and it will
become part of who he is now.
Does he become, uh, you
know, a Eurovision star?
I have no idea.
And I don't care.
Right.
But because of that
exposure, but also because
we didn't force it on, right?
We all had the friend who's
like, couldn't come out to play
because he had to go to piano
lessons and hated his parents.
Great pianist.
Now I, I, they love to hear
him play, but like, it was
a very different thing.
So I think this, this,
this notion of exposure
is super important.
I also think there's
this conditioning Yeah.
That, that we all
come up with you.
You mentioned it just when
you were saying, you know,
the parent who makes the
kid play piano, whether,
whether they love it or not.
Yes.
I say this to say we've
all been conditioned and
have a bias of our, of our
upbringing, um, that comes
from wherever it comes from,
but how we choose to manage
that bias makes us who we are.
I grew up thinking that I would
become nothing, but I wasn't
willing to, to live with that
bias, if that makes sense.
Right.
Like expectations were me, were.
At an all time low
heading into life.
I think that's super important
because I think that, and
look, we can, we can assume
we're gonna become nothing.
We can assume we're gonna
become something great, like
whether our parents are the
ones driving that discussion
or we're the ones driving it.
And somehow we, like from
a really early age and, and
relatively speaking, could be
the start of your career, could
be start of year recreation, but
we start to pretend that we can
draw these like really straight
lines around what happens.
When in the reality life
and career is just like this
series of scribbles that
are really hard to connect
until you can lean back.
Sometimes you see a pattern,
but I think that's, I think
that's a big part of it, right?
Which is being willing to say
that like, look, all these
things are gonna form who I am.
I don't have to accept
that because I took
piano lessons as a kid.
I'm going to become a pianist.
I also don't have to
decide that I'm not going
to do that, or Right.
That it isn't part of who I am.
Right.
It, it's all, it's all
in the batter at the end.
So, um, like I said, we
easily get stuck and I
think as we get further into
our careers, it hardens.
Sure.
That concerns me the most.
Somebody believes,
you know, they're 32,
which isn't that old.
Especially within your career.
It's like the first
quarter of your career.
Barely.
I thought you were gonna say it.
Which isn't that young.
'cause I was thinking
about how young I was.
I was like, no,
it's not that young.
You're early in your career
and like, oh, you know,
this is all I've done.
I will pick out accountants.
Um, all I've done is accounting.
Yeah.
And now I wanna do this thing
in consumer packaged goods.
I've, I've invented
this new, new product.
Right.
But I'm an accountant.
Right.
It's like.
No, you did accounting.
You are not an accountant.
Right, right.
Like it's, that's
not how this works.
And I know for myself, at first
I didn't realize, like I didn't
think I was meant for anything.
So like any work I was taking
was good enough for me.
It was like if it was
paying, that was my job.
Parking lot bouncer.
Fantastic.
Done.
Done.
Like, oh, okay.
So hold on, let me pause
there for a second.
I just gave a kid his first
job this past weekend, a
family that that, that we're,
we're real close to, and
they've got a 15-year-old son.
He is actually been previously
in my entrepreneurship
class, kids' school.
Uh, great dude.
He was trying to figure out
what he wants to do for the
summer and I said, well, hey,
on the weekends if you're
free, I'm building a house.
If you want to come learn
carpentry, et cetera, uh, happy
to, to take you out and pay you.
But, but here's what he said.
And he's right by the way.
He's like, what does it pay?
And it was so funny,
Ryan, 'cause like it's a
very reasonable question.
It is.
But I would've never
asked that at 15,
right?
Yeah.
It's like
what I, what I would've said
is, it pays, do I get paid?
Yeah, yeah, yeah.
It pays fantastic.
Like, like my credo was,
if it pays the answers yes,
then you can tell me what it
is or how much I get paid.
Right.
Just different era.
But, but I thought
that was funny.
But, but he shows
up on Saturday.
And, um, and, and I'm having him
do work around the house and he
said, Hey, Mr. Schroeder, it's
weird that he calls you Mr.
Schroeder.
I was like, what's up man?
He said, what was
your first job?
And, and I told him, you know
this parking lot, bouncer.
And I was like, uh, Tim
Cho, what's your first job?
He said, uh.
This is it.
This is it.
I was like, bro, this
is your first job.
First job.
Yeah, yeah, yeah.
He's like, yep, this is my
first day and my first job.
Like, man, that's
a lot of pressure.
I'm gonna have to, I'm gonna
have to drop some nuggets
from golden nuggets of,
yeah, that's, I got, this
is, this is no longer,
I'm no longer an employer.
I'm a mentor.
Damnit.
Yeah.
Yeah.
Dammit.
Made my life harder.
Anyway.
You, Natalie, to your list
of 50 now you can, uh,
child labor crew manager.
No, this is, this is so funny.
'cause when I, when I was
working with him, I was showing
him how to do, uh, framing,
like, uh, Uhhuh doing framing.
And I said, Tim, have you
ever seen the Karate Kid?
He's like, oh yeah,
the Will Smith movie.
I'm like, God damn dude.
So
he said, oh yeah, the old
movie with Will Smith.
I was like.
No, that's like, no.
And I was joking to him.
I was like, my, my fear
here is that I'm gonna
teach you all these cool
skills, but you will not
know karate at the end of it.
And he, to totally lost that.
He didn't understand
my Mr. Miyagi at all.
But the whole point of that
story is that right now I. He's
figuring out who he wants to be.
Yeah.
Right.
He's a phenomenal,
well, who he thinks
he wants to be
right for today.
But you know what I'm
explaining is that the
field is wide open, man.
Right.
And here's what I say.
Be lots of things.
Be lots of things.
So, so that you can
counterbalance, which
is so funny, right?
Like we sort of understand
that at the beginning because
we're not bound by anything.
At the earlier stages.
The early stages, it's
like, well, okay, I can,
I can be whatever I want
'cause I'm not anything yet.
Right.
So this is where like we,
we know that like curiosity
starts to die, creativity
starts to die as we get older,
like on a relative scale.
Some of us' still very
creative, some of us less so.
But I think that like we
have to start thinking of
those experiences and that
resume as an inventory.
But I see so many people,
particularly founders, because
they wanna make a big change.
To your point, they come from
one industry, they wanna do
something completely different.
Instead of treating that as
like a toolkit and an inventory,
they treat it like a chain.
Right.
And it, and it holds them
to this place that they're
in, which I think is super,
super painful to watch.
Yeah, absolutely.
Lemme expand on that.
We tend to think who we
are as solely, uh, put
toward our, um, our career.
Yeah.
What we get paid for.
Right.
When I, when I tell people I'm
a carpenter, they're like, oh,
you do carpentry for a living.
I, I was like, I don't get paid
for it, but I probably do more
carpentry than most carpenters.
Like, it, it doesn't
like me getting a check
for it doesn't, doesn't
like make me a carpenter.
Right.
That's
not what defines it.
Yeah.
Yeah, exactly.
Right.
Any more than your wife
getting paid to perform, um,
makes her a performer or not.
Yeah.
I mean, she's, she's, she's
great at what she does.
Yep.
But the, the, the paycheck
doesn't change it.
Exactly.
I say that to say most of
us only have one or maybe
two things that we can do
the, uh, capabilities we
possess that are pay worthy.
Um, again, like, because
we understand accounting or
law or something like that,
but that doesn't define the
constrictions of, of who
we are or who we can be.
I've had like 50 careers.
Some of them paid, you
know, some of them.
Pursuits me choosing to go,
uh, professionally with it
or, you know, get paid for it.
Right.
Is incidental, the reason
I bring this up is because
I think a lot of people
associate their identity
with what they get paid for.
A hundred percent they do.
Right?
Uh, it's again, some
people I would argue.
Most founders do, at least
at the point where they're
making decisions around what
they're doing with their
lives as founders, right?
I, because they're, they're
saying, I'm now gonna go
do this other thing that's
completely different
than what I've ever done.
Go back to that whole like,
safety, familiarity dynamic
that we talked about earlier.
I get all feeds together and
they start to say, well, because
that's what I did before.
It's what I, I should keep
doing, and, and now that's who
I am because that's what I got.
Paid to do, which I think is
relatively easy to understand,
like why it happens.
Right.
This is, this is how the
world values you monetarily.
I get it.
I, I, I think early in my
career by accident, I got pulled
into lots of things mm-hmm.
That I somehow got paid for
because I was like hustling.
Right?
Yeah.
I was just trying to figure
anything that would make money.
Yep.
So if it made money, I would
figure out how to do it.
When I graduated high
school, right before I
graduated high school, I
got two full-time jobs.
During the day I was doing
telemarketing, essentially
selling mainframe computers.
And at night I would
go make sandwiches.
And so neither of those
was a career that I wanted
to have for, but they
were the first person that
offered to pay me anything.
And so I just
became that, that, yeah,
I don't have a job now.
I don't have money.
Now you have a job
that offers money.
Okay, that'll work.
Those were you
checked both my boxes.
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
dayLong@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, and be done with it.
But what was interesting about
it, and this is really what
kind of set me off like on
just this chain of events,
was that it didn't occur to me
that I couldn't do something.
And that wasn't because I
was bursting with confidence.
I, it was just more ignorance.
I just, it.
I didn't know enough
about what that thing was.
I'll give an example.
So I'm 17 years old.
I get this job.
I'm selling mainframe
computers now.
It just so happened on this
bizarre chain of events going
through the eighties and
what would now be the early
nineties, that I knew way
more about computers than
most of the people at this
company that I was working for.
Sure.
Right, because I just
got into it early.
Right?
Yeah.
Another chain of events.
And so I get on the phone, and
mind you, I'm 17 years old.
My voice is like this,
but I'm talking like this.
Right.
And, but it's all over
the phone so no one knew.
Right.
And so I'm calling what
used to be considered MIS
managers, if you can think
back to your Ohio State.
Oh yeah.
When IS was Oh yeah.
And I'm basically saying,
Hey, do you need, um,
memory boards for your DPS
9,000 Honey Bull Honeywell
machine, whatever it was.
Right.
And they were like, yeah.
So I'm like, okay, well
I'll just, I'll go write up
a quote for it for $20,000
and um, I'll send it to you.
And my boss is like,
what are you doing?
Yeah.
You're just supposed to
call, you know, and see
if there's a lead and
then pass it over to me.
And I'm like, well, if he
says he wants the product
and the We have the product.
Yeah.
We have it.
Right.
Sell it to him.
Yeah.
Like, isn't that what
we're doing here?
Yeah.
Right.
Yeah.
And, and I remember the,
the, the president of the
company, of this, this
computer company was like.
Wait a minute, you just
closed all your own sales.
I was like, yeah, what
else would I be doing here?
Yeah.
Why else am I on the phone?
Right?
And, and I wasn't saying
it like being cocky.
I actually just,
I was, I was like,
hi, you wanna buy something?
Yeah.
Okay, we'll call you later.
And so, president of
the company and it took,
took me under his wing.
And he was like, I'm,
I'll never forget.
He's like, I'm gonna make
you the deal of your life.
I'm like, oh, Donald Trump.
What?
What have you?
He's like, go on.
I'm moving.
You get this right?
I'm moving you from $5
an hour to $10 an hour.
Boom.
You will now have a sales quota.
Double your income, but
you'll now have a sales quota.
10 bucks an hour.
I had no idea that I
could ever make $10 to
an hour in number two.
I actually didn't know
what a sales quota was.
Yeah.
Didn't matter.
I, I know.
I know what the doubling in in
my hourly pay is and whatever it
needs to happen, I'll do that.
You had me at quitting
my sandwich job.
What was fascinating about
that experience, and I say
this because these things
come in such uns like
nonspecific random ways.
Ryan, next day I wake up and I'm
computer sales guy and I'm like,
how the hell did this happen?
What happened?
Yeah.
I started to watch this
pattern in life of what
it takes to reinvent.
Okay.
And it always started tiny.
It was never this big thing.
And I think this is important.
It was never this big like
overwhelming commitment, right?
I'm now a dancer, right?
Yeah.
It was never that.
Yeah.
It was a tiny event.
Uh, you know, the, the whole
idea of how do you move a
mountain one pebble at a time.
A tiny event that just
imperceptibly at the time
shifted me towards something
and became something more.
Have you gone through the same
thing where like, I mean, think
about it like what you did
here, like when, when you're
doing, uh, sales initially Yep.
And we needed help marketing.
Yeah.
And you're like, yeah,
I can help marketing.
Right?
Yeah.
And you started Chip in
and now you're a CMO.
Yeah.
I think it's been largely
the same thing for me, man.
It's like you, these little
opportunities come along right?
To maybe kind of
stretch things a bit.
Step into a step into a
room that you, you haven't
been in in the past.
Like there's just little
tiny things and, and I guess
in my case, a lot of it
came from, some of it just
came from necessity, right?
Like something needed to happen.
I'm like, well,
I'll try to do that.
Do you know how to do that?
Well, I'll try to do that.
Yeah.
Right, right.
Or things where it was
like, maybe even personal
necessity, like, I want
to go do something else.
I want to be somewhere else.
But in, in most cases.
Going back, it was less
about necessity and
more about curiosity.
Right.
And desire.
Like it was like
things that I, I wanted
legitimately wanted to try.
And, and I think that like
kinda in, in your own case,
you know, in that one, a
little bit more opportunistic,
but in the story you were
telling, it came from I.
Prior knowledge of computers.
Right.
Which came from your
curiosity, right?
And at a time where you were a
kid and you could just explore
kinda the same thing for me.
And we were both kicking around,
you know, TRS eighties or
whatever, back in the, uh, uh,
back in the, the early eighties.
And, and so like, Ryan,
think about your journey here.
Yeah.
Right.
Yeah.
You didn't join as our CMO?
No, no, no, no, no.
I, no, no.
Started, started on the
phones talking to folks and
doing some consulting work.
Then went over, we realized we
needed to, to kind of re reframe
the entire consulting division
jumped in on, on that side.
And then, uh, that led to,
gosh, what were they like?
That's actually pretty funny.
If you look back through
the, the LinkedIn,
there was like content.
Innovation.
Uh, I feel like there
was another, another
one in there somewhere.
Uh, and then, and then
eventually, you know, CMO and
so, but, but this is like,
it's, it's so common, right?
Like it doesn't, that,
it's funny to me that
it doesn't feel funny.
I think other people
look at that and go
like, what the right?
I. That just feels totally
normal and natural to me.
Like, well, of course I've
done a bunch of different shit.
We've been doing
this for 15 years.
What you think, like,
I'm not an accountant.
Yeah.
Well, okay, so think
about it like this.
The more we realize I.
We can take on something
else, the more it
exacerbates that feeling.
Yeah.
I'll give you an example.
You know, you've watched
me through this journey
becoming a carpenter
now, general contractor.
Yeah.
Architect three modeler,
like you name it.
And you know, when, when
I walk people through this
house that we're building, I'm
highly specific about all the
different parts of the house.
About how like I designed
the electrical systems or
the network map or like Yep.
How we did the architecture a
certain way and they're like,
how do you know all this stuff?
Yeah.
Right.
Like how are you the.
GC of this general contractor
of this thing, and I was like, I
didn't, I didn't know any of it.
That's the point.
Yeah.
The, the point is I knew
none of this going into it.
Yeah.
Not even a little bit.
And no one schooled
me on it either.
But you know, like as
we were getting into the
architecture, I had this idea,
this caveman painting, what
this house would be, and I
brought it to an architect.
And the architect gave me
something totally different
than what I was looking for.
And so I brought to another
architect and after months and
months and months, he gave me
something totally different.
And I'm sitting there
getting frustrated.
By the time we're at the
third architect, if you
remember this, Ryan, this is
like years into the process.
I, I see this, this, this
guy on the team and he's
doing like a 3D model.
I. Of the concept Yeah.
Of what they were
trying to put together.
And I asked him, I said,
Hey, how, how, how are you
doing that said, I'm using
a program called SketchUp.
SketchUp.
Right, right.
And I was like, I was like, you
know, I, I've used that a little
bit for woodworking in the past.
Let me figure it out now.
Nobody in their right mind
would sit down and say,
I'm gonna learn how to do
3D modeling architecture.
I'm gonna design my,
literally design my own house.
And it's a good sized house.
So like, it's, it's, it's
a lot to take on the same
person wouldn't say, and I'm
going to build it myself, and
I'm gonna learn how to build
cabinetry and I'm gonna learn
how to, you know, do all these
things and do it all myself.
The reason I was able
to do all that stuff.
Is because I started really
small every single time.
That's been my super like
secret move to that long, long
resume that, that I read off.
What I learned is you can
do almost anything if you
start with the 1% at a time.
That, that's what I think is
fascinating and I, and I try
to teach my kids this, I try
to explain to them that, that
the journey through everything
starts with a single step.
That's the most basic
unintimidating step.
And I'll give you
an example there.
'cause I, I shared this
with you earlier today.
My son comes to me in, in,
in one of you were talking
about Jack coming to you, and
so I, you know, will comes to
me and he says, dad, I found
these nunchucks in storage.
Right?
The fact that that was
even something he could
say makes me really happy.
I found these
nunchucks in storage.
Of course you did.
Sun.
They've been waiting for you.
Anyone in our audience that may
have been so fortunate to grow
up in the eighties likely went
through the same ninja training
that I did, whether it was foam,
rubber stars, nunchucks, baff
skills, computer hacking skills.
Yeah.
Anyway, he comes to me
and he is like, dad, do
you know how to use these?
I was like, buddy, if you only
knew, and we put on a Bruce
Lee video, I was like, this is
where this is supposed to go.
Yeah.
And let your father show
you how to use the nunchaku.
So I'm, I'm whipping him
around you doing all this crazy
stuff, like literally living my
8-year-old cell all over again.
And he's like, can
I learn to do that?
And I said,
yes, yes.
One step at a time.
Ryan, what does
he immediately do?
Spins it around.
Hits himself in the eye.
Right,
right in the face.
Yeah.
I mean like that's,
that is lesson one.
That is lesson one.
Okay.
Nunchuck comes back, right?
Like that.
That's what you learn.
That, that, that which
is spinning comes around.
Dude,
almost on cue my daughter.
Summer.
Picks up another pair
and spins it around.
Wait, you had, you had
enough for full combat,
you had the combat set.
More than one.
One does not only hold
one pair of nunchaku.
True, true, true.
It's clearly you
need backup anyway.
Thankfully they're foam padded.
Point is, you know, even
in something as silly as I
tell the story, just because
it's a funny story, but
what I tell 'em whenever
we're getting into anything.
You can absolutely do this.
You can absolutely reinvent
yourself so long as you
start with one tiny step.
Yeah, little bit.
Little bit.
And let those build
progressively.
And I've used that technique
to get into a dozen
different industries that
I had from pharmaceuticals
to entertainment, to
you name it, right?
I've used that technique,
especially now combined with ai.
To be able to learn stuff.
I should have no
business, even 1% knowing,
right,
right.
Like when I had to do all the
electrical engineering for this
new house, you know, it's, it's,
there's a lot of house there.
There's a lot of
electrical engineering.
When I was doing all the
load calculations and
everything, the electrical
engineer was like, how the
hell did you do any of this?
I'm like, I don't, I don't
even know what it means.
I just went to chat.
GPTI, I put in all my inputs
and, you know, and, and
I got load calculations.
He's like, it's spot on.
I'm like, well, don't blame me.
Played Jet GBT.
The point is I can now do
stuff that I would never
be able to touch before.
Yeah, it's awesome.
It is, and I think it's
an important fundamental
skill for founders to have.
It's probably one of the
most important, right?
Because again, like if you're
setting out to build something
that's never been done,
forget about like all the
kind of requisite skills you
have to have, like you have
to know how to code things.
You have to know how
to design things.
You have to, you have to
understand finance, you have
to understand management,
leadership, all that stuff.
That's great.
But there's always gonna be
that layer of, but no one
has ever built exactly what
we're building right now in
the way that we've built it.
So.
It is a process of invention.
And so like, I think again,
to your point, having that
muscle that says, anytime I
wanna do something new, I'm
gonna start with what's the
most basic step I can take?
And then how do I build
that into 2, 3, 4, 5, right?
Like, how do I go from just
being non chaka to BO staff
and knowing how to sharpen
my own cow traps and you
know, all that stuff, right?
So it's.
It's important, but you gotta,
but you have to take it.
You have to take it stepwise.
Just like building the startup,
we are building ourselves
in parallel as much as we
are building the startup.
And it, it requires reinvention.
I know very few founders who've
built something that I would
say is like super interesting
or like, of course, like if
you were an accountant and
you're like, I'm gonna go start
an accounting consultancy.
Yeah,
right.
Like of course you knew
how to do that 'cause
you were already in one.
But if you're an
accountant and you're like.
I'm gonna go build an auto
optimizing personal finance
widget, um, that listens to
household conversations, uh,
through your Amazon devices
to figure out how we could
better manage your finances.
That's something
totally different.
And just because you have
an accounting background and
understand the financial piece
of it, doesn't mean you how
to do any of the rest of it,
but run.
Let's talk about how all
these stack, what we've
been talking about is, Hey,
you're doing this, but now
you're gonna do this thing.
Yep.
What I think is most
fascinating, I, I think what
has been the, the cornerstone
of our careers has been
how all of those different
facets and personalities
and job titles have.
Come together to make
us the Swiss Army knife
that we are today.
My curiosity across so many
different disciplines and
industries, et cetera, has
actually made me a really
good startup advisor.
Sure.
Because 90% of the time when I
get in front of a a, a founder,
the world that they're in.
I have some direct
connection to.
Yep.
Right.
It's very rare that they say,
Hey, this is what I'm working
in, that I haven't had some
experience in that field, not
making me an expert, just having
some sort of connectivity.
And when I look back, I would
probably tell you that it wasn't
until like my fifth career
change that all the pieces
started working for each other.
Let, let me explain.
I told you I took that job,
uh, telemarketing in that
job I was learning sales.
Sure.
But it turns out I was
already great at sales
Uhhuh
because in the, in the previous
roles that I had throughout
high school, they were
always presentation worthy.
I was always person on stage.
I was class president.
Yeah.
I was always person like
pitching, so to speak.
Yeah.
Yeah.
Right.
And so, so that kind of
helped me in what would
become a formative sales role.
Well, that sales experience
that I gained from a job that
I really didn't even want,
which was the telemarketing
job, was paramount.
In when I started one of the
first interactive agencies.
Right.
You'd be able to go in, in
front of clients and pitch Yep.
Pitch right at 19 uhhuh.
How many 19 year olds
have pitched anything?
Yeah, I'd been pitching
for years, right?
Like I was actually
pretty good at it.
I pitched a couple
fits at that point.
No, I, I, I too had had a
lot of those same kind of
roles where it's like I was
responsible for pitching stuff.
I was the idea person.
I had to go again, go convey
the, the ideas to the powers
that be to make them do
what we needed them to do.
But yeah, most, most
people will not have gone
through that at that age.
And then when I started the
agency, you started one as well.
So you can appreciate this.
Yes.
All of a sudden I had
three disciplines,
technology, marketing, and
design that I needed to
be good at all of them.
'cause I was the only
person working there.
God,
I But man, how much more
did you love that phase?
That I literally felt
like I was being drawn and
quartered or whatever the
hell drawn into three pieces
would be at some point.
That that was literally when
like the impetus for me to,
to stop having the agency came
luckily an opportunity to sell.
It came along, but like.
There came a point where
just having to manage those
three distinct disciplines,
being able to speak their
languages was the core skill.
Like I knew the job, I
knew all three of the
jobs so I could keep them
from killing each other.
That was, that became my role.
But who would've guessed that
technology, marketing, and
design are the fundamentals
of being a startup founder.
Yeah, right.
It just so happened that those
three disciplines around product
and UX design, around customer
acquisition and of course
around technology for a lot
of what we build would become
the cornerstones of being,
becoming a startup founder.
Like didn't see that coming
back to my straight lines
versus scribbles thing, right?
Like this is exactly where
that starts to come into focus.
And I guess because I embraced
all of these different roles,
if I were to like kind of peel
this back to, to at a core,
what I've always been, I've
always been a creator, right?
Mm-hmm.
I'm just a creative person.
I like creating things,
whether I'm writing, whether
I'm building, whether
we're designing a new, uh,
company idea, whatever.
I just like it in creating
and inventing stuff.
Yep.
And it didn't really
matter what it was.
Still doesn't.
Yeah.
I don't care if I'm building a
house or I'm building a company.
I just like building stuff.
Building stuff.
Yep.
And because of that, I never
really tried to pigeonhole
myself to say, well, I'm
just gonna build technology.
I'm just gonna a coder guy.
Right?
Or I'm just gonna do UX design.
I'm just, that, that person,
I was like, I don't know.
I like to create, I'm
just gonna do everything
I want.
As many ingredients as
possible for measures.
Yes.
Yeah.
Yeah.
And, and I would say, Ryan,
at this stage in my life,
uh, now that I'm in my ripe
fifties, I am more open-minded.
I. To exploring how to learn
more stuff than I have ever
been because now I realize
the value of the composite.
You know what I mean?
Yeah,
yeah, yeah.
Well, and what a lovely time to
come to that discovery, given
that we've got more ability to
learn at our fingertips than.
Ever before, like I've been
having this challenge lately
where I keep running into
people who I would say are like
under informed, under-skilled.
Like they just don't seem
to, to know how to do things.
And I keep, I'm
just like, but how?
Like you got all of this.
Like, if, if I could get
one more thing outta life
right now, one more thing.
If, if somebody was like, okay,
we will grant you something,
what would you love right now?
I'd be like.
Could I have five more hours
added to the day where I can
just lock myself away and
learn things and nerd out?
Like I literally wanna go
back to like, and I'm sure
you remember this too, like
when I was 15, 16, 17, I could
direct a lot of my time now.
We, we had the farm at that
point, so I was working
hard, uh, for, for sure.
I was also building
the, the, the, the
first tiny tech company.
And so there were a lot of
things, but, but part of
that was the exploration.
Like the tech company came outta
me nerding out about databases
and connectivity and, and,
and accounting systems, right?
And so, like part of me, like,
that's the thing I would really
love outta life right now is to
just have a little more of that,
like lock myself in a room.
And I did this like
three Sundays ago.
I was like, all right, family.
Normally this is you time.
Today, it's this guy time and
I just spent the day with N
eight N. I was just like, I
want to sit down and really just
like figure out how to build a
couple things that I, I think
are possible, but I haven't
had a time, had time to do.
And that's it.
Like, because there's
so, there's so many tools
out there right now.
So many interesting ways
to connect information.
So many things we can go
build and the ability to do.
It's never been,
never been higher.
So great time to come to
that realization Will.
I'd say then also comes with,
um, a freedom of letting go.
The, the, the freedom.
Oh, yeah.
Freedom of, of, of stopping
and saying, wow, I'm actually
not just this one archetype.
Sure I'm not, you know,
just, just this one thing.
And I don't think, for
a lot of people that's
heretical, like, like what
are you talking about again?
I, I'm accountant, I'm a lawyer.
I, no, yeah.
You understand law that doesn't
make you just a lawyer, right?
Right.
You, you're not this one thing.
And when you let that go and you
say, Hey, the past is the past,
you know, uh, my, my future and
my resume is when I make it,
that opens up incredible doors.
And, and I think as founders
Ryan, like, can you imagine
a founder that that doesn't
give themselves that latitude?
That's dangerous to me.
It, it's, it is dangerous.
And, and we do see it.
Right.
And like to, to me
it's, it's always like.
I think it come, some
of it goes back to that
safety thing, right?
They're like, look,
this is what I knew.
This is what's gotten me
to here, so this must be
the good thing, right?
So I can't fully let go of that.
And at some point you're
just watching what's
happening as a result of
that inability to let go.
And I always see the same
metaphor in my head, which
is like they're holding
onto the anchor thinking
it's the ship, right?
This is the thing that's
gonna get me where w.
Where I'm gonna go.
And it's not, it's
the thing that's gonna
keep you where you are.
And in fact, it's gonna, it's
instead of keeping you safe and
keeping you above water, it's
the thing, it's gonna sink you.
I see this all the time.
Talked to a founder either
late last week or early
this week, absolutely
suffering from exactly this.
So I hope they're listening.
I will definitely
send in this episode.
But the same kind of thing,
it was like, well, because
this is what I already know.
I need to lean on this because
this is what people know me for.
This is what they believe.
I was like, but it's not that
connected to what you wanna do.
Right?
And they're like, yeah, but
I've gotta find a way to
make this the foundation.
Why, like, and because I think
it just comes back to safety.
I, I agree.
And I, I, I think safety
is not a luxury, uh, in,
in our business, right?
Nature of being a founder.
When, when people say a couple
words that come to mind,
safety is never one of them.
Not, not one.
The pull opposite.
But let's take it
like this, Ryan.
If we're in the business
of inventing, yeah.
Creating things that have
never been created before in
markets that have never existed
before, with teams that have
never existed before, it would
stand to reason that the thing
we should be most concerned
about reinventing and creating.
Is ourselves.
Yes.
And I think if we can't put
ourselves in the mentality
that anything is possible for
reinvention, that anything can
be changed based on what the the
markets are or what our passions
are, then that's not really
synonymous with being a founder.
So I think for all of us being
able to zoom out and say,
what I've been isn't who I am.
Well, what I wanna be is
who I am, which is the
fundamentals of being a founder.
Then we set a path.
Then we set a course, which
allows anything we could
possibly imagine to be possible,
especially with ourselves
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@www.startups.com
to see if it's for you.
Could be just the
thing you need.
I hope to see you inside.