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.
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.
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.
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.
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.
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.
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.
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.
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.
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.
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.
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.
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.