June 23, 2025 • 41 mins
Will and Ryan talk about the fascinating and often overlooked journey of reinventing oneself. Will shares his diverse background, from being an ad guy to becoming a multi-time startup founder, and stresses the importance of embracing various roles to build a comprehensive skill set. The duo emphasizes that becoming a founder isn't a job you get hired for but one you create yourself. They explore how personal and professional reinvention can be the key to success in the startup world, encouraging founders to see themselves as a composite of their varied experiences. The episode is filled with personal anecdotes, practical advice, and an inspiring message: you are not confined to one identity or role — your potential is ever-evolving.
Resources:
Startup Therapy Podcast
https://www.startups.com/community/startup-therapy
Website
https://www.startups.com/begin
LinkedIn
https://www.linkedin.com/company/startups-co/
Join our Network of Top Founders
Wil Schroter
https://www.linkedin.com/in/wilschroter/
Ryan Rutan
https://www.linkedin.com/in/ryan-rutan/
What to listen for:
00:43 The Journey to Becoming a Founder
01:28 Reinventing Yourself as a Founder
02:31 The Value of Diverse Experiences
03:55 A Humorous Job List
08:11 The Role of Exposure in Career Choices
13:06 Breaking Free from Career Constraints
19:46 Early Career Hustles
20:22 Learning from Experience
20:53 First Sales Job
21:30 Unexpected Opportunities
23:22 Reinvention Starts Small
24:06 Curiosity and Career Growth
26:14 Building Skills Over Time
28:04 The Power of Starting Small
30:10 Embracing Continuous Learning
32:21 The Value of Diverse Experiences
39:59 Reinventing Yourself as a Founder
Mark as Played
Transcript
Episode Transcript
Available transcripts are automatically generated. Complete accuracy is not guaranteed.
(00:00):
Welcome back to the episode ofthe 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, amember of a typist pool, a
salesperson, a carpenter.
Let's not forget, multi-timestartup founder, but like
(00:20):
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 upbeing founders, right?
And how does it that that likesomehow we keep running into
all these founders who arelike, well, but I don't feel
like I'm qualified for this.
Or I wanna do somethingelse, but this is
what I know how to do.
How do I reconcile that whenthat is kind of how we got
(00:43):
here in the first place?
Right.
I agree it, it's fascinatingbecause fun fact, most of the
people that come to startups.comthat are starting whatever
company, a consumer productscompany, enterprise, SaaS
company, you name it didn'tcome from that industry.
You would think it wouldbe part and parcel.
Yep.
You would think like it'd be10% or something like that.
But I wanna give like twolayers of abstraction for
(01:03):
the folks in the audience.
Number one, almost noone was a founder before.
'cause that that actuallyisn'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 oneinterviews for the founder job.
You create the job, whichmeans you always get hired.
I was just thinking aboutlike, how many times has
somebody had a headhuntercall them and be like, Hey,
(01:25):
we're looking for founders.
Right, right.
Exactly.
Exactly.
Ever.
So, but the second partof that is because you
create the job, you are bydefinition inventing yourself.
Yeah.
In, in most cases,reinventing yourself.
Yeah.
Yet there's a massiveamount of, uh, pushback
that folks have on the ideaof reinventing themselves.
You know?
Sure.
You've got this kind of hardcoded feeling that we are
(01:47):
this one thing, you know,I went to law school, I'm a
lawyer and that's what I am.
Yeah,
no, that's justsomething you did.
I think what would be, whatwould be fun today is to talk
about where this comes from.
This notion of I can only bethis one thing, uh, what it
takes to reinvent yourself to,and we've done it many, many,
many, many times, evenwith a single startup, like
(02:08):
within a single startup.
I think that's somethingsuper important.
It's like how many timeshave we had to morph and
evolve just because thestartup did so, right?
Like by nature we know likeif your startup pivoted.
Which a lot of them do.
You likely had to reinventyourself at that point to
survive the pivot because thebusiness completely changes.
Likelihood is you need tochange at least something
(02:30):
at that point, right?
Absolutely.
And, and I think what'simportant to understand, and,
and I I I wanna make sure we getinto this, is every one of those
pivots, those changes, those,you know, those reinventions.
Becomes part of abigger thing, right?
Becomes part of a bigger thing.
And we become this sortof Swiss army knife of
capabilities and experiences.
And personally I embrace that.
(02:51):
I've got a list somewhere.
I, I'm gonna, I'm gonna seeif 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 yearsago 'cause she was talking
about what she wanted to becomeand I said, uh, give me a day.
'cause it would take me aminute to, to reach out Uhhuh.
I'm gonna come back toyou with every job that
(03:13):
your father has had.
Yeah.
In his life.
And Ryan, I could, itwas 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 thingscome forward, right?
Like, yeah.
Are you a carpenter every day?
Well.
Right now.
Yes.
So bad example, but like you'renot a carpenter every day, but
you still bring your measuretwice, cut once mentality, the
(03:34):
tools, the things that you'velearned through that to what we
do at a, at a startup, right?
It's, it's all of thesethings have their place.
We don't stop being one.
I think this is the thingwhen people get really caught
up and scared about likereinventing themselves, like
we have to stop being that.
You may stop doing that ona daily basis, but you're
gonna stop being that person.
I will always have done thosethings, and so that will
(03:54):
always be part of who I am.
I, I gotta share this list.
I'm not gonna gothrough all of it.
I, I, I
hope a big part of me hopesthat you're actually just
gonna start singing That'sLife by Frank Sinatra.
And, and go through the, I'vebeen a poet, a pop, and, uh,
where I feel like this is
great.
This is in, in no particularorder, in this actual list.
I, I actually put allthe, the dates, stamps,
and where I did this.
(04:15):
Okay.
Uh, you, you ready for this?
I'm ready.
I'm gonna read it fast.
Commercial actor, podcasthost, what do you say?
Basketball coach,high school teacher.
Telemarketer sandwich.
Chef parking lot.
Bouncer.
Casting director, collegelecturer, digital art,
museum curator, creativedirector, database engineer.
Dungeon master hockey player.
Radio, dj, triathlete.
(04:36):
Uh, public company, boardmember school mascot.
Head of businessdevelopment, BBS.
Cis Op dude are we go ourreality show, finalist, middle
school teacher, children'sbook, art author Carpenter,
the CFO, nightclub owner,receptionist president, SBA
young entrepreneur of the year.
Professional speaker.
RPG.
Game designer.
(04:57):
Yes.
3D, modeler architect, nightclubpromoter, interior designer,
general contractor, softwareengineer, field hockey goalie.
And this list goes on.
I'm like.
I, I feel, based on, I, Ithink you missed one, and
this is all very recent.
I a crash test, dummy.
I feel like with your luckwith vehicles lately that,
that you absolutely have been,you've at least been doing
(05:18):
some engineering testing for acouple 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 hasit, it was a Chuck E.
Cheese.
Is that accurate?
No, that was my first job.
My first job was, it was fora pizza place in Connecticut.
(05:40):
They had a parking lotsituation where everybody
kept using their parking lot.
So the owner, uh, Lenopaid me like a few dollars
an hour to kick peopleout of the parking lot.
Weren't supposed tobe parking there.
Amazing.
And I
was, I, I was like 12 years oldat the time, you know, trying
to, trying to be a bouncer andknock people outta parking lots.
That, that,
that, there's some interestinglessons learned there, I'm sure.
But let's talk aboutreinventing yourself.
(06:01):
Yeah.
Okay.
Because every one of thosewere jobs I had, mostly
jobs I got paid for, andall of those required me
to have some learning orexpertise in order to have
those jobs and do those jobs.
But that's not even all of them.
Like I say, I only got likehalfway 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 thatwould be fun to see.
(06:23):
But it tells a story of how weare both what we make ourselves,
but as importantly a composite.
All the things we tryand, 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 thatanybody else doesn't have.
Right.
Like I'm just verywilling to try everything.
(06:43):
Yeah,
yeah.
To just say, 'cause I feellike, I don't know Ryan, like
at some level, yes, I have theidentity of a founder, but to
me that's like saying I havethe 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 yourselfand you think about some of
(07:04):
the different directions you'vegone, what are some of the
highlights that that come out?
You know, it's interesting.
I mean, the, in, in terms ofthe directions I've gone, I
have to give that some morethought in terms of like the,
the, the highlight reel there.
But there's an interesting thingthat I found and, and I think
it was like the point at which.
I started to wantto reinvent myself.
(07:25):
Were places where all of asudden I realized that like
it had become really familiarand maybe safe as a result.
Like this, this sensethat like familiarity
equals safety, right?
Like I'm a lawyer, I'lljust always be a lawyer
and that's somehow safe.
And, and what I realizedwas that it was just
sort of complacencyor wrapped in inertia.
And I didn't like that.
(07:45):
I didn't like that.
And so for me, there've beenthese, like, these triggers
where it's like, if I haven'tbeen pushed or haven't had to
try something new, or haven'tfailed at anything in a while,
like I get really uncomfortable.
I'm like, I get, I getuncomfortable with the comfort.
It's like, okay, this has justbecome commonplace, right?
Like, you know, the minuteI, I I, I master something
on relative basis, I'mlike, I'd like to move on.
(08:06):
I wanna try something else.
I think that's probablypart of the founder
ethos in, in general.
You know, I, I think what'sinteresting is, um, a lot
of our career is shaped bywhat we have exposure to.
Okay?
Yeah.
Yeah.
So, so let, let me give you justa, a, a quick little vignette
that's always just inspired me.
Years and years ago when I waspursuing one of my job titles,
(08:29):
which was board member of theRock and Roll Hall of Fame, um.
Super random peoplelike, wait, what?
Yeah, yeah.
They, they, they had recruitedme to become, to join the
board of the Rock and RollHall of Fame in the, the
most fluke opportunity ever.
It made no sense for anybody.
But the reason I'm tellingyou that is because as part
of the recruiting process,they would give us tickets
to these private concerts.
(08:50):
So like when someone gotinducted into the Rock and
Roll Hall of Fame, therewas a public concert.
Yep.
There was also aprivate concert.
A private show.
Yeah.
Yeah.
One of the inductions wegot to, to be at, which
was amazing, was Metallica.
Oh, wow.
It was unbelievable.
Right?
It's like 200 people in aroom and me and my wife,
like two idiots from Ohio.
Like, what, whatwhatcha doing here?
Anyway, not thepoint of the story.
(09:11):
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 were18, if my memory serves me.
Yeah.
Anyway, he's sitting upthere and he's like, kind of
teary-eyed and he's, he's givinga speech directly to his parents
(09:34):
sitting in front of him and hesaid, 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 thinkof you and your family
because I know there's musicin the house, et cetera.
I've got an anecdote I'llshare 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 wantsto have their kid be a
(09:54):
drummer of all things.
Yeah.
You know, I've actually resisted
that one specificallybecause it's strums
me too.
Right.
Me too.
Yeah.
And so he said, but I'mhere because of you.
And I remember when he wasgiving that speech that like,
everyone's like teary eyed.
'cause like it was one of thoseamazing things to turn to your
parents uhhuh and genuinelythank them for the highest
achievement you've ever made.
Yeah.
Yeah.
Like it was incredible.
But.
(10:15):
Beyond that.
I just kept thinking as hewas saying it, I was like,
what if, what if his parentswere 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 andlike, yeah, but, but what
if his parents, you know,again, talking about like
how we could become anything.
(10:36):
Yeah.
We're just like, no,you're not a drummer.
Yeah.
Yeah.
You're an accountant AndI'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 lotof musical stuff.
The kids, the kids by andlarge like to perform a
(10:58):
lot, but kind of to yourpoint, his parents weren't.
Stuffing drumsticks intohis hand either, right?
They weren't like you,some drummer, right?
They weren't Tiger Wood's dad.
It was like, you willplay 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 veryfirst time ever, Jack decided
I was out playing piano andthe girls come out and were
(11:20):
singing a little bit as I wasplaying, and then Jack shows up.
Now Jack loves to play pianowith me, loves to sit down.
He's, he's learnedto accompany me.
He's, he's sevenloves to accompany.
And then all of asudden he was like, dad.
You know, the songthat 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 westarted playing it.
He wanted to sing it.
(11:40):
He's never done this before,but the girls love to sing.
My wife is amazing singer.
And so just like he all of asudden wanted to do this and we
have this beautiful, I, I willshare with you, I will not put
it out on, on broad social, butI will share with you the, we
Nars just grabbed like a littleclip at the end of him singing.
It was so beautiful, but one ofthe most beautiful parts of it
was she recorded this and dudeabsolutely hits the notes at the
(12:02):
end, which like, I love that.
And it made me really proud.
What made me more proud wasthe entire family erupted
into like just full on joyat him hitting that note.
The girls, you hear thegirls in the background,
you hear me shouting,you hear Nagas screaming
because he just crushed it.
It's such a cool thinglike that is now part of,
of Jack's fabric, right?
Like that is part of what hewas exposed to, and it will
(12:23):
become part of who he is now.
Does he become, uh, youknow, a Eurovision star?
I have no idea.
And I don't care.
Right.
But because of thatexposure, but also because
we didn't force it on, right?
We all had the friend who'slike, couldn't come out to play
because he had to go to pianolessons and hated his parents.
Great pianist.
Now I, I, they love to hearhim play, but like, it was
a very different thing.
So I think this, this,this notion of exposure
(12:44):
is super important.
I also think there'sthis conditioning Yeah.
That, that we allcome up with you.
You mentioned it just whenyou were saying, you know,
the parent who makes thekid play piano, whether,
whether they love it or not.
Yes.
I say this to say we'veall been conditioned and
have a bias of our, of ourupbringing, um, that comes
from wherever it comes from,but how we choose to manage
that bias makes us who we are.
(13:06):
I grew up thinking that I wouldbecome nothing, but I wasn't
willing to, to live with thatbias, if that makes sense.
Right.
Like expectations were me, were.
At an all time lowheading into life.
I think that's super importantbecause I think that, and
look, we can, we can assumewe're gonna become nothing.
We can assume we're gonnabecome something great, like
whether our parents are theones driving that discussion
or we're the ones driving it.
And somehow we, like froma really early age and, and
(13:29):
relatively speaking, could bethe start of your career, could
be start of year recreation, butwe start to pretend that we can
draw these like really straightlines around what happens.
When in the reality lifeand career is just like this
series of scribbles thatare 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 saythat like, look, all these
(13:49):
things are gonna form who I am.
I don't have to acceptthat because I took
piano lessons as a kid.
I'm going to become a pianist.
I also don't have todecide 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 allin the batter at the end.
So, um, like I said, weeasily get stuck and I
think as we get further intoour careers, it hardens.
Sure.
That concerns me the most.
(14:10):
Somebody believes,you know, they're 32,
which isn't that old.
Especially within your career.
It's like the firstquarter of your career.
Barely.
I thought you were gonna say it.
Which isn't that young.
'cause I was thinkingabout how young I was.
I was like, no,it's not that young.
You're early in your careerand 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 thingin consumer packaged goods.
I've, I've inventedthis new, new product.
(14:31):
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'snot how this works.
And I know for myself, at firstI didn't realize, like I didn't
think I was meant for anything.
So like any work I was takingwas good enough for me.
It was like if it waspaying, that was my job.
Parking lot bouncer.
(14:51):
Fantastic.
Done.
Done.
Like, oh, okay.
So hold on, let me pausethere for a second.
I just gave a kid his firstjob 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 previouslyin my entrepreneurship
class, kids' school.
Uh, great dude.
He was trying to figure outwhat he wants to do for the
summer and I said, well, hey,on the weekends if you're
(15:13):
free, I'm building a house.
If you want to come learncarpentry, 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 neverasked that at 15,
right?
Yeah.
It's like
what I, what I would've saidis, it pays, do I get paid?
Yeah, yeah, yeah.
It pays fantastic.
(15:35):
Like, like my credo was,if it pays the answers yes,
then you can tell me what itis or how much I get paid.
Right.
Just different era.
But, but I thoughtthat was funny.
But, but he showsup on Saturday.
And, um, and, and I'm having himdo work around the house and he
said, Hey, Mr. Schroeder, it'sweird that he calls you Mr.
Schroeder.
I was like, what's up man?
He said, what wasyour first job?
(15:55):
And, and I told him, you knowthis parking lot, bouncer.
And I was like, uh, TimCho, what's your first job?
He said, uh.
This is it.
This is it.
I was like, bro, thisis your first job.
First job.
Yeah, yeah, yeah.
He's like, yep, this is myfirst day and my first job.
Like, man, that'sa lot of pressure.
I'm gonna have to, I'm gonnahave 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.
(16:15):
Yeah.
Yeah.
Dammit.
Made my life harder.
Anyway.
You, Natalie, to your listof 50 now you can, uh,
child labor crew manager.
No, this is, this is so funny.
'cause when I, when I wasworking with him, I was showing
him how to do, uh, framing,like, uh, Uhhuh doing framing.
And I said, Tim, have youever seen the Karate Kid?
He's like, oh yeah,the Will Smith movie.
I'm like, God damn dude.
So
(16:37):
he said, oh yeah, the oldmovie with Will Smith.
I was like.
No, that's like, no.
And I was joking to him.
I was like, my, my fearhere is that I'm gonna
teach you all these coolskills, but you will not
know karate at the end of it.
And he, to totally lost that.
He didn't understandmy Mr. Miyagi at all.
But the whole point of thatstory is that right now I. He's
figuring out who he wants to be.
(16:57):
Yeah.
Right.
He's a phenomenal,well, who he thinks
he wants to be
right for today.
But you know what I'mexplaining 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 cancounterbalance, which
is so funny, right?
Like we sort of understandthat at the beginning because
we're not bound by anything.
At the earlier stages.
The early stages, it'slike, well, okay, I can,
I can be whatever I want'cause I'm not anything yet.
(17:19):
Right.
So this is where like we,we know that like curiosity
starts to die, creativitystarts to die as we get older,
like on a relative scale.
Some of us' still verycreative, some of us less so.
But I think that like wehave to start thinking of
those experiences and thatresume as an inventory.
But I see so many people,particularly founders, because
they wanna make a big change.
To your point, they come fromone industry, they wanna do
something completely different.
(17:40):
Instead of treating that aslike a toolkit and an inventory,
they treat it like a chain.
Right.
And it, and it holds themto 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 weare as solely, uh, put
toward our, um, our career.
Yeah.
What we get paid for.
Right.
When I, when I tell people I'ma carpenter, they're like, oh,
(18:01):
you do carpentry for a living.
I, I was like, I don't get paidfor it, but I probably do more
carpentry than most carpenters.
Like, it, it doesn'tlike me getting a check
for it doesn't, doesn'tlike make me a carpenter.
Right.
That's
not what defines it.
Yeah.
Yeah, exactly.
Right.
Any more than your wifegetting paid to perform, um,
makes her a performer or not.
Yeah.
I mean, she's, she's, she'sgreat at what she does.
(18:23):
Yep.
But the, the, the paycheckdoesn't change it.
Exactly.
I say that to say most ofus only have one or maybe
two things that we can dothe, uh, capabilities we
possess that are pay worthy.
Um, again, like, becausewe understand accounting or
law or something like that,but that doesn't define the
constrictions of, of whowe are or who we can be.
I've had like 50 careers.
(18:45):
Some of them paid, youknow, some of them.
Pursuits me choosing to go,uh, professionally with it
or, you know, get paid for it.
Right.
Is incidental, the reasonI bring this up is because
I think a lot of peopleassociate their identity
with what they get paid for.
A hundred percent they do.
Right?
Uh, it's again, somepeople I would argue.
Most founders do, at leastat the point where they're
(19:08):
making decisions around whatthey're doing with their
lives as founders, right?
I, because they're, they'resaying, I'm now gonna go
do this other thing that'scompletely 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 andthey start to say, well, because
that's what I did before.
It's what I, I should keepdoing, and, and now that's who
I am because that's what I got.
(19:29):
Paid to do, which I think isrelatively easy to understand,
like why it happens.
Right.
This is, this is how theworld values you monetarily.
I get it.
I, I, I think early in mycareer by accident, I got pulled
into lots of things mm-hmm.
That I somehow got paid forbecause I was like hustling.
Right?
Yeah.
I was just trying to figureanything that would make money.
Yep.
(19:49):
So if it made money, I wouldfigure out how to do it.
When I graduated highschool, right before I
graduated high school, Igot two full-time jobs.
During the day I was doingtelemarketing, essentially
selling mainframe computers.
And at night I wouldgo make sandwiches.
And so neither of thosewas a career that I wanted
to have for, but theywere the first person that
offered to pay me anything.
(20:10):
And so I just
became that, that, yeah,I don't have a job now.
I don't have money.
Now you have a jobthat offers money.
Okay, that'll work.
Those were youchecked both my boxes.
You know something that'sreally funny about everything
we talk about here isthat none of it is new.
Everything you're dealingwith right now has been done a
(20:31):
thousand times before you, whichmeans the answer already exists.
You may just not know it.
But that's okay.
That's kind of whatwe're here to do.
We talk about this stuff onthe show, but we actually
solve these problems alldayLong@groups.startups.com.
So if any of this soundsfamiliar, stop guessing about
what to do, let us just giveyou the answers to the test
(20:52):
and, and be done with it.
But what was interesting aboutit, and this is really what
kind of set me off like onjust this chain of events,
was that it didn't occur to methat I couldn't do something.
And that wasn't because Iwas bursting with confidence.
I, it was just more ignorance.
I just, it.
I didn't know enoughabout what that thing was.
I'll give an example.
So I'm 17 years old.
(21:13):
I get this job.
I'm selling mainframecomputers now.
It just so happened on thisbizarre chain of events going
through the eighties andwhat would now be the early
nineties, that I knew waymore about computers than
most of the people at thiscompany that I was working for.
Sure.
Right, because I justgot into it early.
Right?
Yeah.
Another chain of events.
And so I get on the phone, andmind you, I'm 17 years old.
(21:34):
My voice is like this,but I'm talking like this.
Right.
And, but it's all overthe phone so no one knew.
Right.
And so I'm calling whatused to be considered MIS
managers, if you can thinkback 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 DPS9,000 Honey Bull Honeywell
machine, whatever it was.
Right.
(21:54):
And they were like, yeah.
So I'm like, okay, wellI'll just, I'll go write up
a quote for it for $20,000and um, I'll send it to you.
And my boss is like,what are you doing?
Yeah.
You're just supposed tocall, you know, and see
if there's a lead andthen pass it over to me.
And I'm like, well, if hesays he wants the product
and the We have the product.
Yeah.
We have it.
Right.
Sell it to him.
Yeah.
Like, isn't that whatwe're doing here?
(22:15):
Yeah.
Right.
Yeah.
And, and I remember the,the, the president of the
company, of this, thiscomputer company was like.
Wait a minute, you justclosed all your own sales.
I was like, yeah, whatelse would I be doing here?
Yeah.
Why else am I on the phone?
Right?
And, and I wasn't sayingit 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 ofthe company and it took,
took me under his wing.
(22:36):
And he was like, I'm,I'll never forget.
He's like, I'm gonna makeyou 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 $5an hour to $10 an hour.
Boom.
You will now have a sales quota.
Double your income, butyou'll now have a sales quota.
10 bucks an hour.
I had no idea that Icould ever make $10 to
(22:57):
an hour in number two.
I actually didn't knowwhat a sales quota was.
Yeah.
Didn't matter.
I, I know.
I know what the doubling in inmy hourly pay is and whatever it
needs to happen, I'll do that.
You had me at quittingmy sandwich job.
What was fascinating aboutthat experience, and I say
this because these thingscome in such uns like
nonspecific random ways.
Ryan, next day I wake up and I'mcomputer sales guy and I'm like,
(23:19):
how the hell did this happen?
What happened?
Yeah.
I started to watch thispattern 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 likeoverwhelming commitment, right?
I'm now a dancer, right?
(23:39):
Yeah.
It was never that.
Yeah.
It was a tiny event.
Uh, you know, the, the wholeidea of how do you move a
mountain one pebble at a time.
A tiny event that justimperceptibly at the time
shifted me towards somethingand became something more.
Have you gone through the samething where like, I mean, think
about it like what you didhere, like when, when you're
(24:00):
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 inand now you're a CMO.
Yeah.
I think it's been largelythe same thing for me, man.
It's like you, these littleopportunities come along right?
To maybe kind ofstretch things a bit.
Step into a step into aroom that you, you haven't
been in in the past.
Like there's just littletiny things and, and I guess
(24:23):
in my case, a lot of itcame 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 waslike, maybe even personal
necessity, like, I wantto go do something else.
I want to be somewhere else.
But in, in most cases.
Going back, it was lessabout necessity and
more about curiosity.
(24:44):
Right.
And desire.
Like it was likethings that I, I wanted
legitimately wanted to try.
And, and I think that likekinda in, in your own case,
you know, in that one, alittle bit more opportunistic,
but in the story you weretelling, it came from I.
Prior knowledge of computers.
Right.
Which came from yourcuriosity, right?
And at a time where you were akid and you could just explore
kinda the same thing for me.
And we were both kicking around,you know, TRS eighties or
(25:05):
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 thephones talking to folks and
doing some consulting work.
Then went over, we realized weneeded to, to kind of re reframe
the entire consulting divisionjumped in on, on that side.
(25:28):
And then, uh, that led to,gosh, what were they like?
That's actually pretty funny.
If you look back throughthe, the LinkedIn,
there was like content.
Innovation.
Uh, I feel like therewas another, another
one in there somewhere.
Uh, and then, and theneventually, 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
(25:50):
it doesn't feel funny.
I think other peoplelook at that and go
like, what the right?
I. That just feels totallynormal and natural to me.
Like, well, of course I'vedone a bunch of different shit.
We've been doingthis for 15 years.
What you think, like,I'm not an accountant.
Yeah.
Well, okay, so thinkabout it like this.
The more we realize I.
We can take on somethingelse, the more it
(26:12):
exacerbates that feeling.
Yeah.
I'll give you an example.
You know, you've watchedme through this journey
becoming a carpenternow, general contractor.
Yeah.
Architect three modeler,like you name it.
And you know, when, whenI walk people through this
house that we're building, I'mhighly specific about all the
different parts of the house.
About how like I designedthe electrical systems or
the network map or like Yep.
How we did the architecture acertain way and they're like,
(26:34):
how do you know all this stuff?
Yeah.
Right.
Like how are you the.
GC of this general contractorof 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 knewnone of this going into it.
Yeah.
Not even a little bit.
And no one schooledme on it either.
But you know, like aswe were getting into the
architecture, I had this idea,this caveman painting, what
this house would be, and Ibrought it to an architect.
(26:54):
And the architect gave mesomething totally different
than what I was looking for.
And so I brought to anotherarchitect and after months and
months and months, he gave mesomething totally different.
And I'm sitting theregetting frustrated.
By the time we're at thethird architect, if you
remember this, Ryan, this islike years into the process.
I, I see this, this, thisguy on the team and he's
doing like a 3D model.
I. Of the concept Yeah.
Of what they weretrying to put together.
And I asked him, I said,Hey, how, how, how are you
(27:16):
doing that said, I'm usinga program called SketchUp.
SketchUp.
Right, right.
And I was like, I was like, youknow, I, I've used that a little
bit for woodworking in the past.
Let me figure it out now.
Nobody in their right mindwould sit down and say,
I'm gonna learn how to do3D 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'sa lot to take on the same
(27:39):
person wouldn't say, and I'mgoing to build it myself, and
I'm gonna learn how to buildcabinetry and I'm gonna learn
how to, you know, do all thesethings and do it all myself.
The reason I was ableto do all that stuff.
Is because I started reallysmall every single time.
That's been my super likesecret move to that long, long
resume that, that I read off.
What I learned is you cando almost anything if you
(28:01):
start with the 1% at a time.
That, that's what I think isfascinating and I, and I try
to teach my kids this, I tryto explain to them that, that
the journey through everythingstarts with a single step.
That's the most basicunintimidating step.
And I'll give youan example there.
'cause I, I shared thiswith you earlier today.
My son comes to me in, in,in one of you were talking
about Jack coming to you, andso I, you know, will comes to
(28:23):
me and he says, dad, I foundthese nunchucks in storage.
Right?
The fact that that waseven something he could
say makes me really happy.
I found thesenunchucks in storage.
Of course you did.
Sun.
They've been waiting for you.
Anyone in our audience that mayhave been so fortunate to grow
up in the eighties likely wentthrough the same ninja training
(28:45):
that I did, whether it was foam,rubber stars, nunchucks, baff
skills, computer hacking skills.
Yeah.
Anyway, he comes to meand he is like, dad, do
you know how to use these?
I was like, buddy, if you onlyknew, and we put on a Bruce
Lee video, I was like, this iswhere this is supposed to go.
Yeah.
And let your father showyou how to use the nunchaku.
So I'm, I'm whipping himaround you doing all this crazy
(29:06):
stuff, like literally living my8-year-old cell all over again.
And he's like, canI learn to do that?
And I said,
yes, yes.
One step at a time.
Ryan, what doeshe 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 whichis spinning comes around.
(29:28):
Dude,
almost on cue my daughter.
Summer.
Picks up another pairand spins it around.
Wait, you had, you hadenough for full combat,
you had the combat set.
More than one.
One does not only holdone pair of nunchaku.
True, true, true.
It's clearly youneed backup anyway.
Thankfully they're foam padded.
Point is, you know, evenin something as silly as I
tell the story, just becauseit's a funny story, but
(29:49):
what I tell 'em wheneverwe're getting into anything.
You can absolutely do this.
You can absolutely reinventyourself so long as you
start with one tiny step.
Yeah, little bit.
Little bit.
And let those buildprogressively.
And I've used that techniqueto get into a dozen
different industries thatI had from pharmaceuticals
to entertainment, toyou name it, right?
(30:10):
I've used that technique,especially now combined with ai.
To be able to learn stuff.
I should have nobusiness, even 1% knowing,
right,
right.
Like when I had to do all theelectrical engineering for this
new house, you know, it's, it's,there's a lot of house there.
There's a lot ofelectrical engineering.
When I was doing all theload calculations and
everything, the electricalengineer was like, how the
hell did you do any of this?
(30:30):
I'm like, I don't, I don'teven know what it means.
I just went to chat.
GPTI, I put in all my inputsand, 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 dostuff that I would never
be able to touch before.
Yeah, it's awesome.
It is, and I think it'san important fundamental
skill for founders to have.
(30:50):
It's probably one of themost important, right?
Because again, like if you'resetting out to build something
that's never been done,forget about like all the
kind of requisite skills youhave to have, like you have
to know how to code things.
You have to know howto design things.
You have to, you have tounderstand finance, you have
to understand management,leadership, all that stuff.
That's great.
But there's always gonna bethat layer of, but no one
has ever built exactly whatwe're building right now in
the way that we've built it.
(31:11):
So.
It is a process of invention.
And so like, I think again,to your point, having that
muscle that says, anytime Iwanna do something new, I'm
gonna start with what's themost basic step I can take?
And then how do I buildthat into 2, 3, 4, 5, right?
Like, how do I go from justbeing non chaka to BO staff
(31:32):
and knowing how to sharpenmy 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 weare building the startup.
And it, it requires reinvention.
I know very few founders who'vebuilt something that I would
say is like super interestingor like, of course, like if
(31:52):
you were an accountant andyou're like, I'm gonna go start
an accounting consultancy.
Yeah,
right.
Like of course you knewhow to do that 'cause
you were already in one.
But if you're anaccountant and you're like.
I'm gonna go build an autooptimizing personal finance
widget, um, that listens tohousehold conversations, uh,
through your Amazon devicesto figure out how we could
better manage your finances.
(32:13):
That's somethingtotally different.
And just because you havean accounting background and
understand the financial pieceof it, doesn't mean you how
to do any of the rest of it,
but run.
Let's talk about how allthese 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 mostfascinating, I, I think what
has been the, the cornerstoneof our careers has been
how all of those differentfacets and personalities
(32:36):
and job titles have.
Come together to makeus the Swiss Army knife
that we are today.
My curiosity across so manydifferent disciplines and
industries, et cetera, hasactually made me a really
good startup advisor.
Sure.
Because 90% of the time when Iget in front of a a, a founder,
the world that they're in.
I have some directconnection to.
(32:58):
Yep.
Right.
It's very rare that they say,Hey, this is what I'm working
in, that I haven't had someexperience in that field, not
making me an expert, just havingsome sort of connectivity.
And when I look back, I wouldprobably tell you that it wasn't
until like my fifth careerchange that all the pieces
started working for each other.
Let, let me explain.
(33:18):
I told you I took that job,uh, telemarketing in that
job I was learning sales.
Sure.
But it turns out I wasalready great at sales
Uhhuh
because in the, in the previousroles that I had throughout
high school, they werealways presentation worthy.
I was always person on stage.
I was class president.
Yeah.
I was always person likepitching, so to speak.
Yeah.
Yeah.
Right.
And so, so that kind ofhelped me in what would
(33:38):
become a formative sales role.
Well, that sales experiencethat 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 thefirst interactive agencies.
Right.
You'd be able to go in, infront of clients and pitch Yep.
Pitch right at 19 uhhuh.
How many 19 year oldshave pitched anything?
Yeah, I'd been pitchingfor years, right?
Like I was actuallypretty good at it.
(33:59):
I pitched a couplefits at that point.
No, I, I, I too had had alot of those same kind of
roles where it's like I wasresponsible for pitching stuff.
I was the idea person.
I had to go again, go conveythe, the ideas to the powers
that be to make them dowhat we needed them to do.
But yeah, most, mostpeople will not have gone
through that at that age.
And then when I started theagency, you started one as well.
So you can appreciate this.
Yes.
(34:19):
All of a sudden I hadthree disciplines,
technology, marketing, anddesign that I needed to
be good at all of them.
'cause I was the onlyperson working there.
God,
I But man, how much moredid you love that phase?
That I literally feltlike I was being drawn and
quartered or whatever thehell drawn into three pieces
would be at some point.
That that was literally whenlike the impetus for me to,
(34:39):
to stop having the agency cameluckily an opportunity to sell.
It came along, but like.
There came a point wherejust having to manage those
three distinct disciplines,being able to speak their
languages was the core skill.
Like I knew the job, Iknew all three of the
jobs so I could keep themfrom killing each other.
That was, that became my role.
But who would've guessed thattechnology, marketing, and
(35:01):
design are the fundamentalsof being a startup founder.
Yeah, right.
It just so happened that thosethree disciplines around product
and UX design, around customeracquisition and of course
around technology for a lotof what we build would become
the cornerstones of being,becoming a startup founder.
Like didn't see that coming
back to my straight linesversus scribbles thing, right?
Like this is exactly wherethat starts to come into focus.
(35:24):
And I guess because I embracedall of these different roles,
if I were to like kind of peelthis back to, to at a core,
what I've always been, I'vealways been a creator, right?
Mm-hmm.
I'm just a creative person.
I like creating things,whether I'm writing, whether
I'm building, whetherwe're designing a new, uh,
company idea, whatever.
I just like it in creatingand inventing stuff.
Yep.
And it didn't reallymatter what it was.
(35:44):
Still doesn't.
Yeah.
I don't care if I'm building ahouse or I'm building a company.
I just like building stuff.
Building stuff.
Yep.
And because of that, I neverreally tried to pigeonhole
myself to say, well, I'mjust 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'mjust gonna do everything
I want.
As many ingredients aspossible for measures.
(36:05):
Yes.
Yeah.
Yeah.
And, and I would say, Ryan,at this stage in my life,
uh, now that I'm in my ripefifties, I am more open-minded.
I. To exploring how to learnmore stuff than I have ever
been because now I realizethe value of the composite.
You know what I mean?
Yeah,
yeah, yeah.
Well, and what a lovely time tocome to that discovery, given
(36:25):
that we've got more ability tolearn at our fingertips than.
Ever before, like I've beenhaving this challenge lately
where I keep running intopeople who I would say are like
under informed, under-skilled.
Like they just don't seemto, to know how to do things.
And I keep, I'mjust like, but how?
Like you got all of this.
(36:47):
Like, if, if I could getone 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 hoursadded to the day where I can
just lock myself away andlearn things and nerd out?
Like I literally wanna goback to like, and I'm sure
you remember this too, likewhen I was 15, 16, 17, I could
(37:09):
direct a lot of my time now.
We, we had the farm at thatpoint, so I was working
hard, uh, for, for sure.
I was also buildingthe, the, the, the
first tiny tech company.
And so there were a lot ofthings, but, but part of
that was the exploration.
Like the tech company came outtame 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 tojust have a little more of that,
(37:32):
like lock myself in a room.
And I did this likethree Sundays ago.
I was like, all right, family.
Normally this is you time.
Today, it's this guy time andI just spent the day with N
eight N. I was just like, Iwant to sit down and really just
like figure out how to build acouple things that I, I think
are possible, but I haven'thad a time, had time to do.
(37:52):
And that's it.
Like, because there'sso, there's so many tools
out there right now.
So many interesting waysto connect information.
So many things we can gobuild and the ability to do.
It's never been,never been higher.
So great time to come tothat 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 stoppingand saying, wow, I'm actually
(38:13):
not just this one archetype.
Sure I'm not, you know,just, just this one thing.
And I don't think, fora lot of people that's
heretical, like, like whatare you talking about again?
I, I'm accountant, I'm a lawyer.
I, no, yeah.
You understand law that doesn'tmake you just a lawyer, right?
Right.
You, you're not this one thing.
And when you let that go and yousay, Hey, the past is the past,
(38:33):
you know, uh, my, my future andmy resume is when I make it,
that opens up incredible doors.
And, and I think as foundersRyan, like, can you imagine
a founder that that doesn'tgive 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 meit's, it's always like.
I think it come, someof it goes back to that
safety thing, right?
They're like, look,this is what I knew.
This is what's gotten meto here, so this must be
(38:55):
the good thing, right?
So I can't fully let go of that.
And at some point you'rejust watching what's
happening as a result ofthat inability to let go.
And I always see the samemetaphor in my head, which
is like they're holdingonto the anchor thinking
it's the ship, right?
This is the thing that'sgonna get me where w.
Where I'm gonna go.
And it's not, it'sthe thing that's gonna
keep you where you are.
And in fact, it's gonna, it'sinstead of keeping you safe and
(39:16):
keeping you above water, it'sthe thing, it's gonna sink you.
I see this all the time.
Talked to a founder eitherlate last week or early
this week, absolutelysuffering from exactly this.
So I hope they're listening.
I will definitelysend 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 becausethis is what people know me for.
This is what they believe.
I was like, but it's not thatconnected to what you wanna do.
(39:37):
Right?
And they're like, yeah, butI've gotta find a way to
make this the foundation.
Why, like, and because I thinkit just comes back to safety.
I, I agree.
And I, I, I think safetyis not a luxury, uh, in,
in our business, right?
Nature of being a founder.
When, when people say a couplewords that come to mind,
safety is never one of them.
Not, not one.
The pull opposite.
(39:58):
But let's take itlike this, Ryan.
If we're in the businessof inventing, yeah.
Creating things that havenever been created before in
markets that have never existedbefore, with teams that have
never existed before, it wouldstand to reason that the thing
we should be most concernedabout reinventing and creating.
Is ourselves.
Yes.
And I think if we can't putourselves in the mentality
that anything is possible forreinvention, that anything can
(40:19):
be changed based on what the themarkets are or what our passions
are, then that's not reallysynonymous with being a founder.
So I think for all of us beingable to zoom out and say,
what I've been isn't who I am.
Well, what I wanna be iswho I am, which is the
fundamentals of being a founder.
Then we set a path.
Then we set a course, whichallows anything we could
possibly imagine to be possible,especially with ourselves
(40:44):
overthinking your startup,because you're going it alone.
You don't have to, and honestlyyou shouldn't because instead,
you can learn directly frompeers who've been in your shoes.
Connect with bootstrapfounders and the advisors
helping them win in thestartups.com community.
Check out the startups.comcommunity@www.startups.com
to see if it's for you.
Could be just thething you need.
(41:04):
I hope to see you inside.
Welcome back to the episode ofthe 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, amember of a typist pool, a
salesperson, a carpenter.
Let's not forget, multi-timestartup founder, but like
(00:20):
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 upbeing founders, right?
And how does it that that likesomehow we keep running into
all these founders who arelike, well, but I don't feel
like I'm qualified for this.
Or I wanna do somethingelse, but this is
what I know how to do.
How do I reconcile that whenthat is kind of how we got
(00:43):
here in the first place?
Right.
I agree it, it's fascinatingbecause fun fact, most of the
people that come to startups.comthat are starting whatever
company, a consumer productscompany, enterprise, SaaS
company, you name it didn'tcome from that industry.
You would think it wouldbe part and parcel.
Yep.
You would think like it'd be10% or something like that.
But I wanna give like twolayers of abstraction for
(01:03):
the folks in the audience.
Number one, almost noone was a founder before.
'cause that that actuallyisn'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 oneinterviews for the founder job.
You create the job, whichmeans you always get hired.
I was just thinking aboutlike, how many times has
somebody had a headhuntercall them and be like, Hey,
(01:25):
we're looking for founders.
Right, right.
Exactly.
Exactly.
Ever.
So, but the second partof that is because you
create the job, you are bydefinition inventing yourself.
Yeah.
In, in most cases,reinventing yourself.
Yeah.
Yet there's a massiveamount of, uh, pushback
that folks have on the ideaof reinventing themselves.
You know?
Sure.
You've got this kind of hardcoded feeling that we are
(01:47):
this one thing, you know,I went to law school, I'm a
lawyer and that's what I am.
Yeah,
no, that's justsomething you did.
I think what would be, whatwould be fun today is to talk
about where this comes from.
This notion of I can only bethis one thing, uh, what it
takes to reinvent yourself to,and we've done it many, many,
many, many times, evenwith a single startup, like
(02:08):
within a single startup.
I think that's somethingsuper important.
It's like how many timeshave we had to morph and
evolve just because thestartup did so, right?
Like by nature we know likeif your startup pivoted.
Which a lot of them do.
You likely had to reinventyourself at that point to
survive the pivot because thebusiness completely changes.
Likelihood is you need tochange at least something
(02:30):
at that point, right?
Absolutely.
And, and I think what'simportant to understand, and,
and I I I wanna make sure we getinto this, is every one of those
pivots, those changes, those,you know, those reinventions.
Becomes part of abigger thing, right?
Becomes part of a bigger thing.
And we become this sortof Swiss army knife of
capabilities and experiences.
And personally I embrace that.
(02:51):
I've got a list somewhere.
I, I'm gonna, I'm gonna seeif 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 yearsago 'cause she was talking
about what she wanted to becomeand I said, uh, give me a day.
'cause it would take me aminute to, to reach out Uhhuh.
I'm gonna come back toyou with every job that
(03:13):
your father has had.
Yeah.
In his life.
And Ryan, I could, itwas 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 thingscome forward, right?
Like, yeah.
Are you a carpenter every day?
Well.
Right now.
Yes.
So bad example, but like you'renot a carpenter every day, but
you still bring your measuretwice, cut once mentality, the
(03:34):
tools, the things that you'velearned through that to what we
do at a, at a startup, right?
It's, it's all of thesethings have their place.
We don't stop being one.
I think this is the thingwhen people get really caught
up and scared about likereinventing themselves, like
we have to stop being that.
You may stop doing that ona daily basis, but you're
gonna stop being that person.
I will always have done thosethings, and so that will
(03:54):
always be part of who I am.
I, I gotta share this list.
I'm not gonna gothrough all of it.
I, I, I
hope a big part of me hopesthat you're actually just
gonna start singing That'sLife by Frank Sinatra.
And, and go through the, I'vebeen a poet, a pop, and, uh,
where I feel like this is
great.
This is in, in no particularorder, in this actual list.
I, I actually put allthe, the dates, stamps,
and where I did this.
(04:15):
Okay.
Uh, you, you ready for this?
I'm ready.
I'm gonna read it fast.
Commercial actor, podcasthost, what do you say?
Basketball coach,high school teacher.
Telemarketer sandwich.
Chef parking lot.
Bouncer.
Casting director, collegelecturer, digital art,
museum curator, creativedirector, database engineer.
Dungeon master hockey player.
Radio, dj, triathlete.
(04:36):
Uh, public company, boardmember school mascot.
Head of businessdevelopment, BBS.
Cis Op dude are we go ourreality show, finalist, middle
school teacher, children'sbook, art author Carpenter,
the CFO, nightclub owner,receptionist president, SBA
young entrepreneur of the year.
Professional speaker.
RPG.
Game designer.
(04:57):
Yes.
3D, modeler architect, nightclubpromoter, interior designer,
general contractor, softwareengineer, field hockey goalie.
And this list goes on.
I'm like.
I, I feel, based on, I, Ithink you missed one, and
this is all very recent.
I a crash test, dummy.
I feel like with your luckwith vehicles lately that,
that you absolutely have been,you've at least been doing
(05:18):
some engineering testing for acouple 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 hasit, it was a Chuck E.
Cheese.
Is that accurate?
No, that was my first job.
My first job was, it was fora pizza place in Connecticut.
(05:40):
They had a parking lotsituation where everybody
kept using their parking lot.
So the owner, uh, Lenopaid me like a few dollars
an hour to kick peopleout of the parking lot.
Weren't supposed tobe parking there.
Amazing.
And I
was, I, I was like 12 years oldat the time, you know, trying
to, trying to be a bouncer andknock people outta parking lots.
That, that,
that, there's some interestinglessons learned there, I'm sure.
But let's talk aboutreinventing yourself.
(06:01):
Yeah.
Okay.
Because every one of thosewere jobs I had, mostly
jobs I got paid for, andall of those required me
to have some learning orexpertise in order to have
those jobs and do those jobs.
But that's not even all of them.
Like I say, I only got likehalfway 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 thatwould be fun to see.
(06:23):
But it tells a story of how weare both what we make ourselves,
but as importantly a composite.
All the things we tryand, 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 thatanybody else doesn't have.
Right.
Like I'm just verywilling to try everything.
(06:43):
Yeah,
yeah.
To just say, 'cause I feellike, I don't know Ryan, like
at some level, yes, I have theidentity of a founder, but to
me that's like saying I havethe 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 yourselfand you think about some of
(07:04):
the different directions you'vegone, what are some of the
highlights that that come out?
You know, it's interesting.
I mean, the, in, in terms ofthe directions I've gone, I
have to give that some morethought in terms of like the,
the, the highlight reel there.
But there's an interesting thingthat I found and, and I think
it was like the point at which.
I started to wantto reinvent myself.
(07:25):
Were places where all of asudden I realized that like
it had become really familiarand maybe safe as a result.
Like this, this sensethat like familiarity
equals safety, right?
Like I'm a lawyer, I'lljust always be a lawyer
and that's somehow safe.
And, and what I realizedwas that it was just
sort of complacencyor wrapped in inertia.
And I didn't like that.
(07:45):
I didn't like that.
And so for me, there've beenthese, like, these triggers
where it's like, if I haven'tbeen pushed or haven't had to
try something new, or haven'tfailed at anything in a while,
like I get really uncomfortable.
I'm like, I get, I getuncomfortable with the comfort.
It's like, okay, this has justbecome commonplace, right?
Like, you know, the minuteI, I I, I master something
on relative basis, I'mlike, I'd like to move on.
(08:06):
I wanna try something else.
I think that's probablypart of the founder
ethos in, in general.
You know, I, I think what'sinteresting is, um, a lot
of our career is shaped bywhat we have exposure to.
Okay?
Yeah.
Yeah.
So, so let, let me give you justa, a, a quick little vignette
that's always just inspired me.
Years and years ago when I waspursuing one of my job titles,
(08:29):
which was board member of theRock and Roll Hall of Fame, um.
Super random peoplelike, wait, what?
Yeah, yeah.
They, they, they had recruitedme to become, to join the
board of the Rock and RollHall of Fame in the, the
most fluke opportunity ever.
It made no sense for anybody.
But the reason I'm tellingyou that is because as part
of the recruiting process,they would give us tickets
to these private concerts.
(08:50):
So like when someone gotinducted into the Rock and
Roll Hall of Fame, therewas a public concert.
Yep.
There was also aprivate concert.
A private show.
Yeah.
Yeah.
One of the inductions wegot to, to be at, which
was amazing, was Metallica.
Oh, wow.
It was unbelievable.
Right?
It's like 200 people in aroom and me and my wife,
like two idiots from Ohio.
Like, what, whatwhatcha doing here?
Anyway, not thepoint of the story.
(09:11):
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 were18, if my memory serves me.
Yeah.
Anyway, he's sitting upthere and he's like, kind of
teary-eyed and he's, he's givinga speech directly to his parents
(09:34):
sitting in front of him and hesaid, 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 thinkof you and your family
because I know there's musicin the house, et cetera.
I've got an anecdote I'llshare 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 wantsto have their kid be a
(09:54):
drummer of all things.
Yeah.
You know, I've actually resisted
that one specificallybecause it's strums
me too.
Right.
Me too.
Yeah.
And so he said, but I'mhere because of you.
And I remember when he wasgiving that speech that like,
everyone's like teary eyed.
'cause like it was one of thoseamazing things to turn to your
parents uhhuh and genuinelythank them for the highest
achievement you've ever made.
Yeah.
Yeah.
Like it was incredible.
But.
(10:15):
Beyond that.
I just kept thinking as hewas saying it, I was like,
what if, what if his parentswere 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 andlike, yeah, but, but what
if his parents, you know,again, talking about like
how we could become anything.
(10:36):
Yeah.
We're just like, no,you're not a drummer.
Yeah.
Yeah.
You're an accountant AndI'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 lotof musical stuff.
The kids, the kids by andlarge like to perform a
(10:58):
lot, but kind of to yourpoint, his parents weren't.
Stuffing drumsticks intohis hand either, right?
They weren't like you,some drummer, right?
They weren't Tiger Wood's dad.
It was like, you willplay 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 veryfirst time ever, Jack decided
I was out playing piano andthe girls come out and were
(11:20):
singing a little bit as I wasplaying, and then Jack shows up.
Now Jack loves to play pianowith me, loves to sit down.
He's, he's learnedto accompany me.
He's, he's sevenloves to accompany.
And then all of asudden he was like, dad.
You know, the songthat 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 westarted playing it.
He wanted to sing it.
(11:40):
He's never done this before,but the girls love to sing.
My wife is amazing singer.
And so just like he all of asudden wanted to do this and we
have this beautiful, I, I willshare with you, I will not put
it out on, on broad social, butI will share with you the, we
Nars just grabbed like a littleclip at the end of him singing.
It was so beautiful, but one ofthe most beautiful parts of it
was she recorded this and dudeabsolutely hits the notes at the
(12:02):
end, which like, I love that.
And it made me really proud.
What made me more proud wasthe entire family erupted
into like just full on joyat him hitting that note.
The girls, you hear thegirls in the background,
you hear me shouting,you hear Nagas screaming
because he just crushed it.
It's such a cool thinglike that is now part of,
of Jack's fabric, right?
Like that is part of what hewas exposed to, and it will
(12:23):
become part of who he is now.
Does he become, uh, youknow, a Eurovision star?
I have no idea.
And I don't care.
Right.
But because of thatexposure, but also because
we didn't force it on, right?
We all had the friend who'slike, couldn't come out to play
because he had to go to pianolessons and hated his parents.
Great pianist.
Now I, I, they love to hearhim play, but like, it was
a very different thing.
So I think this, this,this notion of exposure
(12:44):
is super important.
I also think there'sthis conditioning Yeah.
That, that we allcome up with you.
You mentioned it just whenyou were saying, you know,
the parent who makes thekid play piano, whether,
whether they love it or not.
Yes.
I say this to say we'veall been conditioned and
have a bias of our, of ourupbringing, um, that comes
from wherever it comes from,but how we choose to manage
that bias makes us who we are.
(13:06):
I grew up thinking that I wouldbecome nothing, but I wasn't
willing to, to live with thatbias, if that makes sense.
Right.
Like expectations were me, were.
At an all time lowheading into life.
I think that's super importantbecause I think that, and
look, we can, we can assumewe're gonna become nothing.
We can assume we're gonnabecome something great, like
whether our parents are theones driving that discussion
or we're the ones driving it.
And somehow we, like froma really early age and, and
(13:29):
relatively speaking, could bethe start of your career, could
be start of year recreation, butwe start to pretend that we can
draw these like really straightlines around what happens.
When in the reality lifeand career is just like this
series of scribbles thatare 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 saythat like, look, all these
(13:49):
things are gonna form who I am.
I don't have to acceptthat because I took
piano lessons as a kid.
I'm going to become a pianist.
I also don't have todecide 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 allin the batter at the end.
So, um, like I said, weeasily get stuck and I
think as we get further intoour careers, it hardens.
Sure.
That concerns me the most.
(14:10):
Somebody believes,you know, they're 32,
which isn't that old.
Especially within your career.
It's like the firstquarter of your career.
Barely.
I thought you were gonna say it.
Which isn't that young.
'cause I was thinkingabout how young I was.
I was like, no,it's not that young.
You're early in your careerand 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 thingin consumer packaged goods.
I've, I've inventedthis new, new product.
(14:31):
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'snot how this works.
And I know for myself, at firstI didn't realize, like I didn't
think I was meant for anything.
So like any work I was takingwas good enough for me.
It was like if it waspaying, that was my job.
Parking lot bouncer.
(14:51):
Fantastic.
Done.
Done.
Like, oh, okay.
So hold on, let me pausethere for a second.
I just gave a kid his firstjob 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 previouslyin my entrepreneurship
class, kids' school.
Uh, great dude.
He was trying to figure outwhat he wants to do for the
summer and I said, well, hey,on the weekends if you're
(15:13):
free, I'm building a house.
If you want to come learncarpentry, 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 neverasked that at 15,
right?
Yeah.
It's like
what I, what I would've saidis, it pays, do I get paid?
Yeah, yeah, yeah.
It pays fantastic.
(15:35):
Like, like my credo was,if it pays the answers yes,
then you can tell me what itis or how much I get paid.
Right.
Just different era.
But, but I thoughtthat was funny.
But, but he showsup on Saturday.
And, um, and, and I'm having himdo work around the house and he
said, Hey, Mr. Schroeder, it'sweird that he calls you Mr.
Schroeder.
I was like, what's up man?
He said, what wasyour first job?
(15:55):
And, and I told him, you knowthis parking lot, bouncer.
And I was like, uh, TimCho, what's your first job?
He said, uh.
This is it.
This is it.
I was like, bro, thisis your first job.
First job.
Yeah, yeah, yeah.
He's like, yep, this is myfirst day and my first job.
Like, man, that'sa lot of pressure.
I'm gonna have to, I'm gonnahave 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.
(16:15):
Yeah.
Yeah.
Dammit.
Made my life harder.
Anyway.
You, Natalie, to your listof 50 now you can, uh,
child labor crew manager.
No, this is, this is so funny.
'cause when I, when I wasworking with him, I was showing
him how to do, uh, framing,like, uh, Uhhuh doing framing.
And I said, Tim, have youever seen the Karate Kid?
He's like, oh yeah,the Will Smith movie.
I'm like, God damn dude.
So
(16:37):
he said, oh yeah, the oldmovie with Will Smith.
I was like.
No, that's like, no.
And I was joking to him.
I was like, my, my fearhere is that I'm gonna
teach you all these coolskills, but you will not
know karate at the end of it.
And he, to totally lost that.
He didn't understandmy Mr. Miyagi at all.
But the whole point of thatstory is that right now I. He's
figuring out who he wants to be.
(16:57):
Yeah.
Right.
He's a phenomenal,well, who he thinks
he wants to be
right for today.
But you know what I'mexplaining 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 cancounterbalance, which
is so funny, right?
Like we sort of understandthat at the beginning because
we're not bound by anything.
At the earlier stages.
The early stages, it'slike, well, okay, I can,
I can be whatever I want'cause I'm not anything yet.
(17:19):
Right.
So this is where like we,we know that like curiosity
starts to die, creativitystarts to die as we get older,
like on a relative scale.
Some of us' still verycreative, some of us less so.
But I think that like wehave to start thinking of
those experiences and thatresume as an inventory.
But I see so many people,particularly founders, because
they wanna make a big change.
To your point, they come fromone industry, they wanna do
something completely different.
(17:40):
Instead of treating that aslike a toolkit and an inventory,
they treat it like a chain.
Right.
And it, and it holds themto 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 weare as solely, uh, put
toward our, um, our career.
Yeah.
What we get paid for.
Right.
When I, when I tell people I'ma carpenter, they're like, oh,
(18:01):
you do carpentry for a living.
I, I was like, I don't get paidfor it, but I probably do more
carpentry than most carpenters.
Like, it, it doesn'tlike me getting a check
for it doesn't, doesn'tlike make me a carpenter.
Right.
That's
not what defines it.
Yeah.
Yeah, exactly.
Right.
Any more than your wifegetting paid to perform, um,
makes her a performer or not.
Yeah.
I mean, she's, she's, she'sgreat at what she does.
(18:23):
Yep.
But the, the, the paycheckdoesn't change it.
Exactly.
I say that to say most ofus only have one or maybe
two things that we can dothe, uh, capabilities we
possess that are pay worthy.
Um, again, like, becausewe understand accounting or
law or something like that,but that doesn't define the
constrictions of, of whowe are or who we can be.
I've had like 50 careers.
(18:45):
Some of them paid, youknow, some of them.
Pursuits me choosing to go,uh, professionally with it
or, you know, get paid for it.
Right.
Is incidental, the reasonI bring this up is because
I think a lot of peopleassociate their identity
with what they get paid for.
A hundred percent they do.
Right?
Uh, it's again, somepeople I would argue.
Most founders do, at leastat the point where they're
(19:08):
making decisions around whatthey're doing with their
lives as founders, right?
I, because they're, they'resaying, I'm now gonna go
do this other thing that'scompletely 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 andthey start to say, well, because
that's what I did before.
It's what I, I should keepdoing, and, and now that's who
I am because that's what I got.
(19:29):
Paid to do, which I think isrelatively easy to understand,
like why it happens.
Right.
This is, this is how theworld values you monetarily.
I get it.
I, I, I think early in mycareer by accident, I got pulled
into lots of things mm-hmm.
That I somehow got paid forbecause I was like hustling.
Right?
Yeah.
I was just trying to figureanything that would make money.
Yep.
(19:49):
So if it made money, I wouldfigure out how to do it.
When I graduated highschool, right before I
graduated high school, Igot two full-time jobs.
During the day I was doingtelemarketing, essentially
selling mainframe computers.
And at night I wouldgo make sandwiches.
And so neither of thosewas a career that I wanted
to have for, but theywere the first person that
offered to pay me anything.
(20:10):
And so I just
became that, that, yeah,I don't have a job now.
I don't have money.
Now you have a jobthat offers money.
Okay, that'll work.
Those were youchecked both my boxes.
You know something that'sreally funny about everything
we talk about here isthat none of it is new.
Everything you're dealingwith right now has been done a
(20:31):
thousand times before you, whichmeans the answer already exists.
You may just not know it.
But that's okay.
That's kind of whatwe're here to do.
We talk about this stuff onthe show, but we actually
solve these problems alldayLong@groups.startups.com.
So if any of this soundsfamiliar, stop guessing about
what to do, let us just giveyou the answers to the test
(20:52):
and, and be done with it.
But what was interesting aboutit, and this is really what
kind of set me off like onjust this chain of events,
was that it didn't occur to methat I couldn't do something.
And that wasn't because Iwas bursting with confidence.
I, it was just more ignorance.
I just, it.
I didn't know enoughabout what that thing was.
I'll give an example.
So I'm 17 years old.
(21:13):
I get this job.
I'm selling mainframecomputers now.
It just so happened on thisbizarre chain of events going
through the eighties andwhat would now be the early
nineties, that I knew waymore about computers than
most of the people at thiscompany that I was working for.
Sure.
Right, because I justgot into it early.
Right?
Yeah.
Another chain of events.
And so I get on the phone, andmind you, I'm 17 years old.
(21:34):
My voice is like this,but I'm talking like this.
Right.
And, but it's all overthe phone so no one knew.
Right.
And so I'm calling whatused to be considered MIS
managers, if you can thinkback 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 DPS9,000 Honey Bull Honeywell
machine, whatever it was.
Right.
(21:54):
And they were like, yeah.
So I'm like, okay, wellI'll just, I'll go write up
a quote for it for $20,000and um, I'll send it to you.
And my boss is like,what are you doing?
Yeah.
You're just supposed tocall, you know, and see
if there's a lead andthen pass it over to me.
And I'm like, well, if hesays he wants the product
and the We have the product.
Yeah.
We have it.
Right.
Sell it to him.
Yeah.
Like, isn't that whatwe're doing here?
(22:15):
Yeah.
Right.
Yeah.
And, and I remember the,the, the president of the
company, of this, thiscomputer company was like.
Wait a minute, you justclosed all your own sales.
I was like, yeah, whatelse would I be doing here?
Yeah.
Why else am I on the phone?
Right?
And, and I wasn't sayingit 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 ofthe company and it took,
took me under his wing.
(22:36):
And he was like, I'm,I'll never forget.
He's like, I'm gonna makeyou 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 $5an hour to $10 an hour.
Boom.
You will now have a sales quota.
Double your income, butyou'll now have a sales quota.
10 bucks an hour.
I had no idea that Icould ever make $10 to
(22:57):
an hour in number two.
I actually didn't knowwhat a sales quota was.
Yeah.
Didn't matter.
I, I know.
I know what the doubling in inmy hourly pay is and whatever it
needs to happen, I'll do that.
You had me at quittingmy sandwich job.
What was fascinating aboutthat experience, and I say
this because these thingscome in such uns like
nonspecific random ways.
Ryan, next day I wake up and I'mcomputer sales guy and I'm like,
(23:19):
how the hell did this happen?
What happened?
Yeah.
I started to watch thispattern 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 likeoverwhelming commitment, right?
I'm now a dancer, right?
(23:39):
Yeah.
It was never that.
Yeah.
It was a tiny event.
Uh, you know, the, the wholeidea of how do you move a
mountain one pebble at a time.
A tiny event that justimperceptibly at the time
shifted me towards somethingand became something more.
Have you gone through the samething where like, I mean, think
about it like what you didhere, like when, when you're
(24:00):
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 inand now you're a CMO.
Yeah.
I think it's been largelythe same thing for me, man.
It's like you, these littleopportunities come along right?
To maybe kind ofstretch things a bit.
Step into a step into aroom that you, you haven't
been in in the past.
Like there's just littletiny things and, and I guess
(24:23):
in my case, a lot of itcame 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 waslike, maybe even personal
necessity, like, I wantto go do something else.
I want to be somewhere else.
But in, in most cases.
Going back, it was lessabout necessity and
more about curiosity.
(24:44):
Right.
And desire.
Like it was likethings that I, I wanted
legitimately wanted to try.
And, and I think that likekinda in, in your own case,
you know, in that one, alittle bit more opportunistic,
but in the story you weretelling, it came from I.
Prior knowledge of computers.
Right.
Which came from yourcuriosity, right?
And at a time where you were akid and you could just explore
kinda the same thing for me.
And we were both kicking around,you know, TRS eighties or
(25:05):
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 thephones talking to folks and
doing some consulting work.
Then went over, we realized weneeded to, to kind of re reframe
the entire consulting divisionjumped in on, on that side.
(25:28):
And then, uh, that led to,gosh, what were they like?
That's actually pretty funny.
If you look back throughthe, the LinkedIn,
there was like content.
Innovation.
Uh, I feel like therewas another, another
one in there somewhere.
Uh, and then, and theneventually, 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
(25:50):
it doesn't feel funny.
I think other peoplelook at that and go
like, what the right?
I. That just feels totallynormal and natural to me.
Like, well, of course I'vedone a bunch of different shit.
We've been doingthis for 15 years.
What you think, like,I'm not an accountant.
Yeah.
Well, okay, so thinkabout it like this.
The more we realize I.
We can take on somethingelse, the more it
(26:12):
exacerbates that feeling.
Yeah.
I'll give you an example.
You know, you've watchedme through this journey
becoming a carpenternow, general contractor.
Yeah.
Architect three modeler,like you name it.
And you know, when, whenI walk people through this
house that we're building, I'mhighly specific about all the
different parts of the house.
About how like I designedthe electrical systems or
the network map or like Yep.
How we did the architecture acertain way and they're like,
(26:34):
how do you know all this stuff?
Yeah.
Right.
Like how are you the.
GC of this general contractorof 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 knewnone of this going into it.
Yeah.
Not even a little bit.
And no one schooledme on it either.
But you know, like aswe were getting into the
architecture, I had this idea,this caveman painting, what
this house would be, and Ibrought it to an architect.
(26:54):
And the architect gave mesomething totally different
than what I was looking for.
And so I brought to anotherarchitect and after months and
months and months, he gave mesomething totally different.
And I'm sitting theregetting frustrated.
By the time we're at thethird architect, if you
remember this, Ryan, this islike years into the process.
I, I see this, this, thisguy on the team and he's
doing like a 3D model.
I. Of the concept Yeah.
Of what they weretrying to put together.
And I asked him, I said,Hey, how, how, how are you
(27:16):
doing that said, I'm usinga program called SketchUp.
SketchUp.
Right, right.
And I was like, I was like, youknow, I, I've used that a little
bit for woodworking in the past.
Let me figure it out now.
Nobody in their right mindwould sit down and say,
I'm gonna learn how to do3D 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'sa lot to take on the same
(27:39):
person wouldn't say, and I'mgoing to build it myself, and
I'm gonna learn how to buildcabinetry and I'm gonna learn
how to, you know, do all thesethings and do it all myself.
The reason I was ableto do all that stuff.
Is because I started reallysmall every single time.
That's been my super likesecret move to that long, long
resume that, that I read off.
What I learned is you cando almost anything if you
(28:01):
start with the 1% at a time.
That, that's what I think isfascinating and I, and I try
to teach my kids this, I tryto explain to them that, that
the journey through everythingstarts with a single step.
That's the most basicunintimidating step.
And I'll give youan example there.
'cause I, I shared thiswith you earlier today.
My son comes to me in, in,in one of you were talking
about Jack coming to you, andso I, you know, will comes to
(28:23):
me and he says, dad, I foundthese nunchucks in storage.
Right?
The fact that that waseven something he could
say makes me really happy.
I found thesenunchucks in storage.
Of course you did.
Sun.
They've been waiting for you.
Anyone in our audience that mayhave been so fortunate to grow
up in the eighties likely wentthrough the same ninja training
(28:45):
that I did, whether it was foam,rubber stars, nunchucks, baff
skills, computer hacking skills.
Yeah.
Anyway, he comes to meand he is like, dad, do
you know how to use these?
I was like, buddy, if you onlyknew, and we put on a Bruce
Lee video, I was like, this iswhere this is supposed to go.
Yeah.
And let your father showyou how to use the nunchaku.
So I'm, I'm whipping himaround you doing all this crazy
(29:06):
stuff, like literally living my8-year-old cell all over again.
And he's like, canI learn to do that?
And I said,
yes, yes.
One step at a time.
Ryan, what doeshe 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 whichis spinning comes around.
(29:28):
Dude,
almost on cue my daughter.
Summer.
Picks up another pairand spins it around.
Wait, you had, you hadenough for full combat,
you had the combat set.
More than one.
One does not only holdone pair of nunchaku.
True, true, true.
It's clearly youneed backup anyway.
Thankfully they're foam padded.
Point is, you know, evenin something as silly as I
tell the story, just becauseit's a funny story, but
(29:49):
what I tell 'em wheneverwe're getting into anything.
You can absolutely do this.
You can absolutely reinventyourself so long as you
start with one tiny step.
Yeah, little bit.
Little bit.
And let those buildprogressively.
And I've used that techniqueto get into a dozen
different industries thatI had from pharmaceuticals
to entertainment, toyou name it, right?
(30:10):
I've used that technique,especially now combined with ai.
To be able to learn stuff.
I should have nobusiness, even 1% knowing,
right,
right.
Like when I had to do all theelectrical engineering for this
new house, you know, it's, it's,there's a lot of house there.
There's a lot ofelectrical engineering.
When I was doing all theload calculations and
everything, the electricalengineer was like, how the
hell did you do any of this?
(30:30):
I'm like, I don't, I don'teven know what it means.
I just went to chat.
GPTI, I put in all my inputsand, 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 dostuff that I would never
be able to touch before.
Yeah, it's awesome.
It is, and I think it'san important fundamental
skill for founders to have.
(30:50):
It's probably one of themost important, right?
Because again, like if you'resetting out to build something
that's never been done,forget about like all the
kind of requisite skills youhave to have, like you have
to know how to code things.
You have to know howto design things.
You have to, you have tounderstand finance, you have
to understand management,leadership, all that stuff.
That's great.
But there's always gonna bethat layer of, but no one
has ever built exactly whatwe're building right now in
the way that we've built it.
(31:11):
So.
It is a process of invention.
And so like, I think again,to your point, having that
muscle that says, anytime Iwanna do something new, I'm
gonna start with what's themost basic step I can take?
And then how do I buildthat into 2, 3, 4, 5, right?
Like, how do I go from justbeing non chaka to BO staff
(31:32):
and knowing how to sharpenmy 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 weare building the startup.
And it, it requires reinvention.
I know very few founders who'vebuilt something that I would
say is like super interestingor like, of course, like if
(31:52):
you were an accountant andyou're like, I'm gonna go start
an accounting consultancy.
Yeah,
right.
Like of course you knewhow to do that 'cause
you were already in one.
But if you're anaccountant and you're like.
I'm gonna go build an autooptimizing personal finance
widget, um, that listens tohousehold conversations, uh,
through your Amazon devicesto figure out how we could
better manage your finances.
(32:13):
That's somethingtotally different.
And just because you havean accounting background and
understand the financial pieceof it, doesn't mean you how
to do any of the rest of it,
but run.
Let's talk about how allthese 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 mostfascinating, I, I think what
has been the, the cornerstoneof our careers has been
how all of those differentfacets and personalities
(32:36):
and job titles have.
Come together to makeus the Swiss Army knife
that we are today.
My curiosity across so manydifferent disciplines and
industries, et cetera, hasactually made me a really
good startup advisor.
Sure.
Because 90% of the time when Iget in front of a a, a founder,
the world that they're in.
I have some directconnection to.
(32:58):
Yep.
Right.
It's very rare that they say,Hey, this is what I'm working
in, that I haven't had someexperience in that field, not
making me an expert, just havingsome sort of connectivity.
And when I look back, I wouldprobably tell you that it wasn't
until like my fifth careerchange that all the pieces
started working for each other.
Let, let me explain.
(33:18):
I told you I took that job,uh, telemarketing in that
job I was learning sales.
Sure.
But it turns out I wasalready great at sales
Uhhuh
because in the, in the previousroles that I had throughout
high school, they werealways presentation worthy.
I was always person on stage.
I was class president.
Yeah.
I was always person likepitching, so to speak.
Yeah.
Yeah.
Right.
And so, so that kind ofhelped me in what would
(33:38):
become a formative sales role.
Well, that sales experiencethat 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 thefirst interactive agencies.
Right.
You'd be able to go in, infront of clients and pitch Yep.
Pitch right at 19 uhhuh.
How many 19 year oldshave pitched anything?
Yeah, I'd been pitchingfor years, right?
Like I was actuallypretty good at it.
(33:59):
I pitched a couplefits at that point.
No, I, I, I too had had alot of those same kind of
roles where it's like I wasresponsible for pitching stuff.
I was the idea person.
I had to go again, go conveythe, the ideas to the powers
that be to make them dowhat we needed them to do.
But yeah, most, mostpeople will not have gone
through that at that age.
And then when I started theagency, you started one as well.
So you can appreciate this.
Yes.
(34:19):
All of a sudden I hadthree disciplines,
technology, marketing, anddesign that I needed to
be good at all of them.
'cause I was the onlyperson working there.
God,
I But man, how much moredid you love that phase?
That I literally feltlike I was being drawn and
quartered or whatever thehell drawn into three pieces
would be at some point.
That that was literally whenlike the impetus for me to,
(34:39):
to stop having the agency cameluckily an opportunity to sell.
It came along, but like.
There came a point wherejust having to manage those
three distinct disciplines,being able to speak their
languages was the core skill.
Like I knew the job, Iknew all three of the
jobs so I could keep themfrom killing each other.
That was, that became my role.
But who would've guessed thattechnology, marketing, and
(35:01):
design are the fundamentalsof being a startup founder.
Yeah, right.
It just so happened that thosethree disciplines around product
and UX design, around customeracquisition and of course
around technology for a lotof what we build would become
the cornerstones of being,becoming a startup founder.
Like didn't see that coming
back to my straight linesversus scribbles thing, right?
Like this is exactly wherethat starts to come into focus.
(35:24):
And I guess because I embracedall of these different roles,
if I were to like kind of peelthis back to, to at a core,
what I've always been, I'vealways been a creator, right?
Mm-hmm.
I'm just a creative person.
I like creating things,whether I'm writing, whether
I'm building, whetherwe're designing a new, uh,
company idea, whatever.
I just like it in creatingand inventing stuff.
Yep.
And it didn't reallymatter what it was.
(35:44):
Still doesn't.
Yeah.
I don't care if I'm building ahouse or I'm building a company.
I just like building stuff.
Building stuff.
Yep.
And because of that, I neverreally tried to pigeonhole
myself to say, well, I'mjust 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'mjust gonna do everything
I want.
As many ingredients aspossible for measures.
(36:05):
Yes.
Yeah.
Yeah.
And, and I would say, Ryan,at this stage in my life,
uh, now that I'm in my ripefifties, I am more open-minded.
I. To exploring how to learnmore stuff than I have ever
been because now I realizethe value of the composite.
You know what I mean?
Yeah,
yeah, yeah.
Well, and what a lovely time tocome to that discovery, given
(36:25):
that we've got more ability tolearn at our fingertips than.
Ever before, like I've beenhaving this challenge lately
where I keep running intopeople who I would say are like
under informed, under-skilled.
Like they just don't seemto, to know how to do things.
And I keep, I'mjust like, but how?
Like you got all of this.
(36:47):
Like, if, if I could getone 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 hoursadded to the day where I can
just lock myself away andlearn things and nerd out?
Like I literally wanna goback to like, and I'm sure
you remember this too, likewhen I was 15, 16, 17, I could
(37:09):
direct a lot of my time now.
We, we had the farm at thatpoint, so I was working
hard, uh, for, for sure.
I was also buildingthe, the, the, the
first tiny tech company.
And so there were a lot ofthings, but, but part of
that was the exploration.
Like the tech company came outtame 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 tojust have a little more of that,
(37:32):
like lock myself in a room.
And I did this likethree Sundays ago.
I was like, all right, family.
Normally this is you time.
Today, it's this guy time andI just spent the day with N
eight N. I was just like, Iwant to sit down and really just
like figure out how to build acouple things that I, I think
are possible, but I haven'thad a time, had time to do.
(37:52):
And that's it.
Like, because there'sso, there's so many tools
out there right now.
So many interesting waysto connect information.
So many things we can gobuild and the ability to do.
It's never been,never been higher.
So great time to come tothat 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 stoppingand saying, wow, I'm actually
(38:13):
not just this one archetype.
Sure I'm not, you know,just, just this one thing.
And I don't think, fora lot of people that's
heretical, like, like whatare you talking about again?
I, I'm accountant, I'm a lawyer.
I, no, yeah.
You understand law that doesn'tmake you just a lawyer, right?
Right.
You, you're not this one thing.
And when you let that go and yousay, Hey, the past is the past,
(38:33):
you know, uh, my, my future andmy resume is when I make it,
that opens up incredible doors.
And, and I think as foundersRyan, like, can you imagine
a founder that that doesn'tgive 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 meit's, it's always like.
I think it come, someof it goes back to that
safety thing, right?
They're like, look,this is what I knew.
This is what's gotten meto here, so this must be
(38:55):
the good thing, right?
So I can't fully let go of that.
And at some point you'rejust watching what's
happening as a result ofthat inability to let go.
And I always see the samemetaphor in my head, which
is like they're holdingonto the anchor thinking
it's the ship, right?
This is the thing that'sgonna get me where w.
Where I'm gonna go.
And it's not, it'sthe thing that's gonna
keep you where you are.
And in fact, it's gonna, it'sinstead of keeping you safe and
(39:16):
keeping you above water, it'sthe thing, it's gonna sink you.
I see this all the time.
Talked to a founder eitherlate last week or early
this week, absolutelysuffering from exactly this.
So I hope they're listening.
I will definitelysend 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 becausethis is what people know me for.
This is what they believe.
I was like, but it's not thatconnected to what you wanna do.
(39:37):
Right?
And they're like, yeah, butI've gotta find a way to
make this the foundation.
Why, like, and because I thinkit just comes back to safety.
I, I agree.
And I, I, I think safetyis not a luxury, uh, in,
in our business, right?
Nature of being a founder.
When, when people say a couplewords that come to mind,
safety is never one of them.
Not, not one.
The pull opposite.
(39:58):
But let's take itlike this, Ryan.
If we're in the businessof inventing, yeah.
Creating things that havenever been created before in
markets that have never existedbefore, with teams that have
never existed before, it wouldstand to reason that the thing
we should be most concernedabout reinventing and creating.
Is ourselves.
Yes.
And I think if we can't putourselves in the mentality
that anything is possible forreinvention, that anything can
(40:19):
be changed based on what the themarkets are or what our passions
are, then that's not reallysynonymous with being a founder.
So I think for all of us beingable to zoom out and say,
what I've been isn't who I am.
Well, what I wanna be iswho I am, which is the
fundamentals of being a founder.
Then we set a path.
Then we set a course, whichallows anything we could
possibly imagine to be possible,especially with ourselves
(40:44):
overthinking your startup,because you're going it alone.
You don't have to, and honestlyyou shouldn't because instead,
you can learn directly frompeers who've been in your shoes.
Connect with bootstrapfounders and the advisors
helping them win in thestartups.com community.
Check out the startups.comcommunity@www.startups.com
to see if it's for you.
Could be just thething you need.
(41:04):
I hope to see you inside.
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