April 14, 2025 • 49 mins
"Am I failing as a founder if I'm not constantly pushing for more growth?"
After achieving stability in his 5-year-old business, Will Pearson brings this question to our coaching session. With a 4-year-old daughter and 7-month-old son at home, Will has found a balance between work and family, but feels guilty about it.
This episode explores:
- The identity crisis that comes with business stability
- How founder narratives create unnecessary pressure
- Why rest periods are essential for sustainable growth
- Finding confidence in your own definition of success
For anyone who's ever wondered if they're "hungry enough" as an entrepreneur or felt guilty for prioritizing life outside their business, this episode will help!
Enjoyed this episode? Ready to take your leadership and personal growth to the next level? Please visit my website to learn more about coaching with me.
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Transcript
Episode Transcript
Available transcripts are automatically generated. Complete accuracy is not guaranteed.
Speaker 1 (00:00):
Welcome to Slow Down, to Speed Up, where we have real
one-time coaching sessions withstartup founders working
through the challenges ofleadership.
I'm your host and executivecoach, brian Wang.
Today I'm joined by WillPearson, a founder five and a
half years into his journeywho's reached a pivotal
inflection point.
After years of chasing growthand navigating uncertainty,
will's business has finallystabilized.
(00:20):
It's profitable systems are inplace and sustainable growth
continues.
Yet the stability he's longsought brings some unexpected
discomfort too.
With a four-year-old daughterand seven-month-old son at home,
will struggles with the tensionmany founders face but rarely
discuss.
Is maintaining balance betweenwork, family and self actually
okay, or should he be constantlypushing for more growth and
(00:42):
taking bigger risks?
Beneath this practical questionlies a deeper identity
challenge reconciling theentrepreneur's drive to maximize
potential with the reality of afull life outside the business.
During our session, willconfronts how the expectations
he's internalized about being areal founder quote unquote
conflict with the values heholds most dear.
(01:02):
If you've ever felt guilty fornot constantly pushing
boundaries in your business orwondered if you're leaving
opportunity on the table, Ithink you'll find some valuable
perspective here.
Let's dive in.
Hey Will, it's great to see you.
Hey, brian, good to see you.
Thanks for having me,absolutely so.
I'd love to just spend timejust getting to know what are
you bringing in and where are wegoing to take the conversation
(01:24):
today?
Speaker 2 (01:24):
spend time just getting to know what are you
bringing in and where are wegoing to take the conversation
today?
Absolutely Well.
I am a first-time founder, butI'm about five and a half years
into the journey and I feel likeI've hit an inflection point in
the path here and I really wantto get into what is risk as an
entrepreneur and then as afounder and what does that mean
as the business evolves and asyour personal life evolves.
(01:45):
So the other thing I'll addabout myself is, in addition to
a five and a half year oldcompany, I have a four year old
daughter and a seven month oldson, and I think being a dad and
having that become a hugepriority in my life is also
really key to this dilemma I'mhaving of how much to invest in
the business and what kind ofrisks to take around the
(02:06):
business and just kind of howthat relates to everything in my
life really.
Speaker 1 (02:12):
Yeah, I know that for many of us, the way that we
relate to risk changes.
You know, when we're startingto build a family versus when
you're kind of on your own andyou're in your 20s and you know
the world feels very different.
So I'm hearing from you, will.
It's like there's some questionof how to relate to risk.
You know, professionally, withthe business, especially in the
(02:36):
context of raising young kids.
You know, focusing on familyand so on and so forth.
Speaker 2 (02:43):
Yeah, that's right.
And we've really reached thefirst point where I would say
the business is relativelystable.
And you know, the first fourplus years is really focused on
growth, figuring out what do wehave, product market fit, what
is that product?
You know our journey has beenthrough building software,
offering services, differenttypes of services.
Some are very related, some arenot related at all.
(03:03):
You know our journey has beenthrough building software,
offering services, differenttypes of services.
Some are very related, some arenot related at all.
You know we tried a bunch ofdifferent stuff and really in
the interest of unlocking growthand around the four-year mark
we'd made a little bit of ashift because we felt like we
had that focus down, we knewwhat we were good at and it
(03:25):
became more about profitabilityand building a scalable business
and less about chasing growthnumbers.
And that has been prettyeffective over the last year
where we're still growing alittle bit but we are profitable
and it feels like structure'sin place to kind of continue
this business on for a long time.
And that's also sort of a newfeeling.
(03:45):
I've been so much into thisjourney thinking about growth
and just how big can this get,and now I'm a little bit torn of
.
Do I continue to invest or takebig risks and big swings in the
business to see how big it canget, or do I pull back?
And what does that mean formyself and my goals if things
(04:07):
are a little stable and I allowit to be stable?
I've never really thought aboutthat stage, but I'm
experiencing it right now.
Speaker 1 (04:14):
Okay, so I get the sense that being in this more
stable era let's call it feels alittle uncomfortable.
Is that an accurate way ofdescribing it?
Speaker 2 (04:24):
It does feel a little uncomfortable and one of the
reasons I brought up my familyinitially is that that is, you
know, anything but stable.
You know just sort of my day today of being around you know my
two young children and seeingthem grow and trying to help
them and develop them.
But, you know, knowing thatthere's a lot of chaos and just,
you know, getting and in thebed, that's a lot to manage on a
(04:46):
daily basis.
Then I get to work and I'm like, okay, this is a little calmer
here.
I don't have a million fires toput out, like maybe I did a few
years ago.
So, yeah, I'm a bituncomfortable and feeling like,
should I be creating a littlebit of that chaos at work as
well in order to, you know, hitthe next level of growth?
(05:06):
Like, what does thatopportunity cost if I'm, if I
don't do that, or should I just,you know, kind of enjoy this
period and let things happen asas they will?
Speaker 1 (05:15):
This might sound like an obvious question, but can I
ask?
So let's say you took some bigrisks and unlocked a lot of that
growth and you know, like thecurve, bending the curve in,
like the significant way, whatdoes that achieve for you?
Speaker 2 (05:28):
I guess it's.
It's more of feeling like I'vehit the potential.
An obvious answer to that forme, you know, I just feel like I
don't want to leave opportunityon the table, and I think
opportunity means a fewdifferent things.
I mean, like the obvious one isis financial reasons.
Um, you know, of course, if I10 X the business, do I 10 X my
(05:52):
net worth?
Like sure, that sounds, thatsounds great.
But you know the otheropportunities just around uh,
you know, as your business getsbigger, just more doors open,
you meet more people, um, youexperience more things like um.
You know I've really enjoyedthat aspect of being a founder
too and the connections I'vemade um over the last five years
.
So I don't want to uh miss outon on those potential
(06:14):
opportunities uh as well.
But it's not a uh, you knowit's not obvious how to do that
either.
Right, like I think to try to10 X uh the business would
require taking a lot of chanceson things that I don't know if
they would work or not, and thatcould be, you know, my, my time
(06:35):
, my money, et cetera.
Speaker 1 (06:37):
Yeah, yeah.
So I just want to reflect onthat, for a second Part of what
makes entrepreneurship somagical is that you like there's
like all this potential right,you use that word potential so
it's like you could make so manythings happen, and it's largely
up to you, and luck obviouslyis a huge part of it too, right,
you know that, and so what Ihear from you will is like, oh,
(07:00):
wow, like we're in a good placenow, but if we, if we made the
right moves, then this thingcould be like man, so much, 10x
bigger, and not even just on themoney component, but who you're
exposed to, who you collidewith, the opportunities that
might generate as a result ofthat effort.
And so there's something thereon the potential, and I hear
(07:23):
there's a tension, tension, atension in that too, which is
like, oh, we don't know how it'sgoing to turn out.
So there's like this riskcomponent to it, right.
And so I'll ask you anotherkind of maybe simple question so
when you consider, like therisk that you're fearing or like
the consequence that you'refearing on the other side of
that, like what does that looklike for you?
Speaker 2 (07:52):
Yeah, it's.
I think it's largely my time isa big thing that comes to mind
and you know, I really want tofind a balance, or have a
balance, you know, between myown mental health, being a dad,
being a founder, being able tomanage all of that, and I feel
like I have pretty good balanceright now.
So my fear is losing control ofthat balance, losing control of
my schedule in order to chasesomething that may or may not
(08:16):
exist in a way.
Speaker 1 (08:21):
What's really interesting about your answer
just now was what you didn't say, which was you didn't say oh
man, I'm afraid it's going tolike tank the business or that
we're going to take these shotsand like they just totally don't
work.
It was really like, oh man, wemight make these moves and it's
gonna demand so much of my timeand attention and knock me out
(08:43):
of balance.
So much of my time andattention and not going to get
out of balance, and so maybeunderneath that, I hear, like
having proper boundaries isreally important to you.
Speaker 2 (08:54):
Does that feel true?
Yeah, definitely, definitely.
And yeah, there is someinherent risk that the business
does suffer and we drop where weare are.
But just given that we are in alittle bit of a stable state, I
guess I'm less concerned aboutthat than you know.
I would have been in the pasthaving this conversation because
I feel like we can, even indifficult times, kind of dig out
(09:16):
of it and, you know, get backto a level of stability again.
Speaker 1 (09:20):
I guess okay, so all right, cool.
So let's say you're, you'remaking some of these moves we
don't have to define thespecific ones, but, like you're,
you're starting to make somechanges.
What is it that makes youbelieve that you won't be able
to own your time and attentionin the way that you want?
Speaker 2 (09:37):
I think what I've found is the growth of the
business has largely beenrelationship based.
You know, we're a B2B business,we're primarily selling
services.
We had a lot of referrals and alot of those referrals have
been kind of long cultivatedrelationships.
So my, my fear there is, if wehave, let's say, you know, 10 to
(10:04):
12 really good partners rightnow that refer us business and
vice versa, if I make that 20 to25 instead, am I the one to do
all of that?
And therefore do I need to beon the road a lot more than I am
?
Do I need to be at every singleconference?
And you know, I think theobvious response to that as well
(10:26):
, why don't you scale this andreplicate that?
And you know, have other peoplethat can do it.
But again, that goes back tothe risk because we haven't
really had other people do it.
It's my co founder and I havemaintained most of these
relationships, yeah, so the riskwould be bringing somebody in
and kind of having them try toreplicate us.
So far there's not evidence sothat we've been able to achieve
that okay.
Speaker 1 (10:48):
So let's just assume for a moment that it is possible
to hire and, you know, train uppeople and other people to like
sort of take some of that onright, um, and if you just
imagine that movie, so like okay, now your team is starting to
like actually step up so theycan scale, I'm curious, like
what's the sort of initialreaction that you have to that
(11:08):
mental image?
Speaker 2 (11:09):
The first reaction is that it's probably going to be
expensive.
You know that risk and would wejeopardize some of the
stability Again kind of goingback to that word by spending
more money?
Again, kind of going back tothat word by spending more money
and then knowing that it takesa while to really cultivate
(11:32):
relationships and figure outwhich ones are interesting and
helpful, it could get that wrongand it could take a while to
get the payback on thatinvestment.
Speaker 1 (11:38):
Yeah, yeah, totally.
So it could cost a lot of money, requires patience.
You might not know if it'sgoing to work out for some time,
right, I hear a lot of that inthere, right, and so what I'm
struck by is, like that there'sthe way I see it, you could kind
of remain where you are, andthere's a familiarity with that,
(11:59):
there's a comfort to that.
And then there's also like theventuring into the unknown.
You're not really sure how it'sgoing to look and feel, where
it's going to lead, right, yeah,I guess, um, one has to
consider, like what would makeit worth it to you, right?
So, like, if you consider, likethe idea of like stepping
(12:21):
beyond where you are now andinto that unknown zone, like I'm
curious for you personally,like what would make that choice
really worth it for you,knowing that you're not sure how
it's going to work out?
Speaker 2 (12:31):
right, yeah, I've never been one of those founders
that starts a company with theintent to make it a
billion-dollar unicorn company.
Being a founder to me has beenabout creating flexibility and
cultivating relationships andhopefully having financial
freedom as a result of that.
And I think the output of whatkind of success looks like in
(12:57):
growing yeah, you'll have toforgive me, that was the
question.
Right, keep going.
Okay, all right, success theoutput here is, yeah, it's.
I guess it's really justhitting the opportunity that
(13:18):
exists out there, maximizing thepotential of the company.
Wouldn't you know if you did?
Yeah, maybe you never do, andthat's the struggle here, I
guess, if I, maybe, I'm kind ofthinking right now that we're
(13:41):
approaching the potential of thecompany and that's why it's
sort of like, okay, are westable now?
Because we've we've got theoperations figured out and you
know this, this kind of steadycourse is going to kind of lead
us there, and going for muchhigher will maybe just lead us
to the same place.
So you know, I don't know ifI'll ever know how high things
(14:02):
can really get, but it feelslike the basics are in place now
and that's again kind of a newuncomfortable feeling for me,
where I've been used to takingwhat I would consider bigger
risks and chances to get higher.
Speaker 1 (14:17):
I'm going to ask you to reach back into memory just
for a moment, because I'mcurious when you look at how you
got to where you are now.
What was a key decision orchoice that you made in recent
memory that got you here?
Speaker 2 (14:29):
Yeah, we've taken outside investment in the form
of equity and debt before, andthat's because the growth
numbers were super, super highand it felt obvious that if we
added money, that we could spendthat money and keep that growth
rate high and maintain ourservices.
And basically we had a stretchwhere the growth slowed down,
(14:54):
even though we were stillspending that kind of money.
And that's really where thetransformation took place of
okay, maybe it's not justspending money, maybe there's
just some other things thatwe're doing, that's making this
work, and it's not all abouttaking on outside investment.
And so now that we're here,like taking a bunch of outside
(15:19):
money, I wouldn't really knowwhat to do with it right now,
whereas I think I knew what todo with it back then because we
were growing so fast and feltlike we had all these holes to
plug.
Speaker 1 (15:30):
Got it Okay.
So it sounds like in recentmemory you've sort of been
focusing on, like, tuning thebusiness.
Like getting recent memory.
You've sort of been focusing ontuning the business, getting
the fundamentals right.
The machine has sort of beenbuilt up in a way, but as it
stands right now, if someonehanded you a whole bucket of
money, you're not really surewhere that would go, necessarily
(15:50):
in terms of generating ameaningful return for the biz.
Is that right?
That's right.
Yeah, like a meaningful returnfor the biz, is that?
Is that right?
Speaker 2 (15:55):
That's right, yeah, and, and you know, when I talk
about my time, my money, as partof the risk here, hiring a
bunch of people, it's somethingwe did before and and some of
them worked out, a lot of themdidn't Right.
So that has led me again, youknow, to this point of how much,
how much risk do we takeknowing that it didn't all work
(16:18):
out before, even though some ofit did?
Speaker 1 (16:22):
Yeah, I just want to empathize with that for a moment
.
I mean, I think it's like a lotof this is trial by error and
experiments.
When you invest a bunch ofmoney into things that don't
(16:44):
work out, it can be really easyto feel like, well, man, I don't
want to take another swing,knowing that the hit rate,
looking back wasn't great.
There's like I have no idea ifit's going to work out.
Speaker 2 (16:49):
There's something that maybe we'll learn, but it
could be costly, yeah, and Iimagine a lot of founders feel
that way, and I imagine a lot offounders feel that way.
You know, you look at yourprevious balance sheets and P&Ls
and you're like, oh my gosh, Ispent millions of dollars on
this.
Like we got nothing out of that.
Yeah, you know, a little bitI'm feeling that.
Or it's not necessarily buyer'sremorse, because you learn a
(17:10):
lot from it and you adjustaccordingly.
But you know really concernedabout making the same mistakes
if they're, if they're notnecessary.
And just you know understandingthis, this new, new reality of
kind of accepting being stableand kind of letting things
happen more, more organicallythan than trying to force it as
(17:31):
we have in the past.
Speaker 1 (17:32):
Okay, so this might sound like a strange question,
but let's say you were single,you didn't have a family,
business was still in the past.
Okay, so this might sound likea strange question, but let's
say you were single, you didn'thave a family, business was
still in the same place as it isnow.
How would that change thiswhole situation, if at all?
Speaker 2 (17:48):
I would probably be more willing to give up my time,
first and foremost, and so Ithink about traveling and going
to conferences and events andthings I don't really enjoy
doing that much because I kindof miss being home right when I
when I'm out and I probably atleast try doing more of that to
(18:08):
see if, to see if it would work.
Speaker 1 (18:12):
Okay.
So there's like this thingabout traveling that feels like
it's necessary to, you know,push the business's growth.
You don't really enjoy it.
You'd actually much rather beat home, but if family weren't
actually the concern, then you'dmaybe go out there and do more
of that.
Speaker 2 (18:30):
Yeah, Because I think the reason I enjoy traveling
generally.
I don't enjoy traveling when itmeans I'm missing moments with
the family, essentially.
Speaker 1 (18:40):
Yeah, that makes sense.
So you're in this place whereyou have two young kids Really
you have an infant at home andof course the natural impulse is
to be there as much as you can.
Then there's just like yeah,but what do we do with the
business sort of thing?
This is not me giving youadvice at all, it's just more of
(19:03):
a curiosity.
So let's say you spent the nextyear or two just really focused
on being a dad, being a husband, enjoying your family as much
as you could and then saying,okay, cool, the business will
evolve as it evolves, I'm notgoing to push it too much over
the next couple of years.
What would have to be true inthat scenario for you to
actually feel satisfied withthat whole setup?
Speaker 2 (19:26):
It's hard to admit that for me It'd be hard to
admit I'm just going to be lessfocused on the business.
I mean, there's a hundredpercent chance.
I have done that over the lastfew years, but I don't really
outwardly say it because italmost feels like I'm letting
the business down, I'm lettingpeople down, letting our
partners down by uh, if I'm not,uh, a hundred percent invested,
(19:52):
um, but you know the way I'vethought about that is 100%
invested, um, but you know theway I've thought about that is
by a hundred percent, has justchanged.
You know the way, the way Ifocus on the business, you know
you're just in terms ofdelegation and focus, you know
as, uh, I think has improved alot because I don't have, you
know, the extra 25 hours on aweekend to work on stuff like I
(20:15):
used to, or I don't choose to, Iguess.
So, yeah, I think that's areasonable approach, but I hate
to cut you off, but I am curious.
Speaker 1 (20:26):
You said like this thing about hating to admit that
.
Can you just say more aboutthat, Like this notion that I
would hate to admit that that'sthe case.
I'm paraphrasing a little bit,but I'm curious if you went into
that a little bit more withthat, what you meant by it.
Speaker 2 (20:43):
Yeah, there's a, there's a vision for the company
that I've sold to people andthey've kind of made their own
investment into it, whetherthat's employment or a
partnership or you know aninvestment my co-founder as well
.
We've communicated a largevision for the company and it's
not there yet.
(21:03):
I don't know if it ever will be, but it's at a stage now that
again, it's stable, but we'renot a household name for every
email marketer in the world.
That was the original goal.
So then, that's why it feelslike it'd be a bit of a letdown
to say, all right, well, I don'treally have that vision now, I
just want it to organically growover the next few years.
(21:25):
Um, yeah, that's why it's a,that's why it's a letdown,
because am I still aiming forthat vision?
And are people really boughtinto the vision?
And all of a sudden, all of asudden, they're not if I tell
them that I'm not.
Speaker 1 (21:38):
Yeah, and I don't want to put words on your mouth.
I don't get the sense thatyou're not bought into it.
I get the sense that you'relike yeah, yeah.
So there's a little bit of athought experiment.
I was running with you, becauseit'd be one thing if you were
like, yeah, I'm just going tocoast guys, I don't get that
(22:00):
sense from you.
My sense is that you want to befully there for your family and
you want to be just ascommitted to your business.
Now maybe the priority hasshifted a little bit,
understandably, right, butyou're still fully committed to
the success of the business andso, yeah, I'm curious about what
it's like when you'reinteracting with your
stakeholders, your team.
You know you talked about thisvision and and they're all sort
(22:21):
of really committed to that.
They're bought into that, like,hmm, I'm sort of seeing what's
coming up.
Like if, if you went to themand you were like, guys, it's
really important to me that I'mthere with my family and like I
want to press this businessforward.
I don't know what it looks likeyet.
Maybe you've had some versionof this already but if you were
(22:41):
to say something to that effect,how, how do you think people
around you would react?
Speaker 2 (22:48):
I think they'd be like well, obviously that's
already happening.
Yeah, but the way you put that,you know I, I took, I took,
took time off when my son wasborn.
If one of my kids is home sick,like I always, you know, I tell
the team because I make sure,you know, I take care of my kid.
My wife works as well like, andshe's, you know, it takes on,
(23:08):
you know, even more with thekids.
But we do it together, we tryto make everything equal and so,
yeah, I think if I just cameout and said it, they'd say we
know you're doing that.
But again, it's just sort oflike this admission that I'm not
all in on the business, eventhough my actions probably show
(23:29):
that I'm all in, but I'm alsoall in on myself and my family
as well.
I don't want to lose sight of,like the, the, the me aspect of
this too.
You know, it's not just familyand business.
Like I do kind of take my ownhealth, you know, physical and
mental, really seriously too aspart of this equation, and I've
done a good job with that, Ithink.
(23:49):
So I wanted to mention that aswell.
But yeah, I mean it's, it's,it's how I act.
So they probably already seethis to a certain extent.
Speaker 1 (23:56):
Yes, how much of this you mentioned like the dilemma
in the beginning of this.
It's how much of the dilemma isguilt that you're not like
1000% on the business becauseyou actually care about yourself
and your, your, your family too.
Speaker 2 (24:13):
Yeah, I guess I don't know if I need to be a thousand
percent.
Yeah, I know it was anexaggeration out there, but yeah
, yeah, I think it's part of it.
I think there's things that I,you know, I'm maybe not, I'm not
doing that, I probably could be, and that's I think.
I think that's what you mean bythat, the, the a thousand
percent there's.
There's opportunities that Ikeep using travel but I think
(24:35):
it's beyond that.
It's it's, you know, certaingrowth and development things in
the business that I can do froma computer in my house that you
know I don't prioritize right.
I work on other stuff, uh,instead of that, and it's it's
it just goes to to what we'retalking about.
For the hours that I doallocate to the business.
(24:56):
I'm super focused and try todelegate as much as I can, but I
do think there's some stuffthat sort of sits at my desk
that I don't do right nowbecause I don't think it's worth
the time that I give thebusiness, that it's worth it to
do it Right right.
Speaker 1 (25:15):
Yeah, I'm pausing because I know we've taken some
twists and turns here, so let mejust come back to you.
I just want to tune in.
So what's the question?
That's still kind of burningfor you at the moment.
Speaker 2 (25:28):
Yeah, it's maybe less about how do we manage risk and
more about just kind of beingcomfortable in a situation where
adding hours to work is not anoption I want to necessarily
(25:48):
explore.
And you know, in a way that'sleaving stuff on the table, as
we just mentioned, but beingokay with that, that sort of
accepting that those thingsbeing left from the table aren't
necessarily going to move theneedle.
It's not like I sit here allday and work on stuff that
doesn't matter.
Right, I'm still working onimportant things, and the other
things maybe I'm not, maybe theyactually don't matter that much
, otherwise I would.
(26:08):
I would be doing them and Ihave to kind of accept that and
feel like I am doing, you know,as as much as I can to to to
allow the business to hit itspotential.
Speaker 1 (26:23):
Yeah, so to to paraphrase what I heard back
from you is is essentially likehow do I, how do I be okay with
the fact that I'm spending thetime I am with the business and
I'm not willing to put more in?
I'm spending the time I am withthe business and I'm not
willing to put more in yeah, Ithink so, yeah.
So what's making?
Again, it's going to sound likea sort of a basic question, but
(26:43):
what's making it not feelingokay right now?
Speaker 2 (26:45):
It doesn't feel.
It doesn't feel okay, becauseit's maybe not what you're
supposed to do as a founder.
You're supposed to.
Yeah, I think, uh, you knowyou're you're, you're supposed
to be really focused on growthand, uh, you know you want to
(27:06):
get everything to be a lotbigger than it is.
Um, and yeah, I guess I'vethought of myself kind of in
that singular focus for so longthat letting that go is
difficult, and what does thatmean for myself and how I think
(27:32):
about myself as a founder andhow I'm running the company?
Speaker 1 (27:37):
You're right that we're as founders.
There's no shortage of people'sideas of what it's supposed to
be and how you're supposed toact and decisions that you make
and so on and so forth.
This might be tricky, but let'ssay you magically stripped out
all other people's ideas of whatyou're supposed to be and how
(27:59):
you're supposed to be doingthings here, like what would
that change for you?
Speaker 2 (28:01):
it's part of it, but I I think what I still would
wrestle with is the never-endinglist of potential opportunities
to grow the business.
It's almost something like myco-founder and I have that list
(28:22):
and we have ideas, and yousometimes just throw something
out of the blue in the middle ofthe night to each other Like,
oh man, if this worked for us,that type of thing.
And then sometimes it requiresthe other person to say, okay,
let's, let's look at this in sixmonths.
Like this is just not somethingwe can do right now.
But sometimes you get reallyexcited about it and you want to
(28:42):
do something and then yourealize it's going to completely
take up all of my time or itrequires a new software or a new
person to do it, and that'swhen I get a little hesitant to
make that investment from there.
So yeah, I know I keep goingback to this theme, but there's
almost an opportunity cost.
Sometimes I feel, when I'm notpursuing all these extra ideas
for the business and that sortof drives me nuts to just let
(29:06):
all that sit there and notnecessarily get attacked not
necessarily get attacked.
Speaker 1 (29:12):
You know 100%.
I just want to stay with thatfor a moment.
Yeah, I think my sense of youis that you have no shortage of
ideas, especially if you'reriffing on them with your
co-founder.
I don't know them, but you'llhave this like infinite well of
a different ideas and plans andand and things that you could
tackle, and yet you have thiskind of limited amount of time,
this finite amount of time in 24hours in a day.
(29:34):
Right, you got to take care ofyourself, your family, and so
what I hear from you Will islike, oh, like the experience of
like coming up with the ideabut then deciding no, no, no,
we're not going to do that rightnow, or we're going to do that
later on or never.
That's like painful, it's like,ah man, like I have to feel
(29:58):
this, like I don't know what.
How would you describe it?
Is it like a disappointment?
Speaker 2 (30:06):
or like what's, what's the feeling of it?
For you?
It's a feeling of it's, it'salmost a loss in a way, like I
yeah I, it's an experience thatI, that I want to have, of just
of trying it and seeing if itworks, and and not having that
experience feels like I'm, youknow, I'm just really missing
out.
I'm losing this opportunity.
Um to to, Hmm.
Speaker 1 (30:27):
Yeah, yeah, yeah.
Um reminds me of, I think, ifyou look at the etymology of the
word decide, I believe it'ssomething to the effect of
killing all the other options.
You choose one course of action, but, like all the other
different paths you could havetaken, you've decided to kill
them essentially, and there's aloss to that.
There's like a grief to thatright, all the lives you could
have lived right, which is partof what makes decisions
(30:50):
difficult at times and makesdecisions difficult at times,
and that's what I hear in you,in what you're describing.
The other thing I think I'mhearing, though, is that there's
some sense of going after oneof those ideas feels really big
(31:10):
in terms of resources or havingto change course on something.
Does that feel true, like whenyou're describing this
experience?
It's oh, this is kind of like abig thing for us to invest in.
Speaker 2 (31:19):
Yeah, absolutely, and that is probably a result of
really tightening things uplately.
So, you know, when I had, whenyou're when you're having
massive growth and you've gotmoney coming in easily from
investors or banks or whateverit's, you know, it felt easier
to try things.
(31:39):
And now, yeah, I think we'rereally focused and, you know,
really tight on budgets, whichis probably a good thing, right.
Speaker 1 (31:50):
But at the same time, there is a little bit of that
experimentation and risk thatyou know it's has been pulled
back I this is a little liketactical, but I wonder, like,
what does it look like for youto make those experiments
smaller, right, in terms of sortof just for the sake of like
exploration and you know whenyou and your co-founder are
(32:12):
riffing, and that sort of thing?
Speaker 2 (32:18):
Yeah, I think, I think we can, I think there.
You know it's like you can'thave a podcast, you don't talk
about AI, right, but obviouslyyou know now, versus a few years
ago, it's a little easier toget started on things with, with
, with those tools that are outthere.
So, yeah, I think it's, I thinkit's, I think it's doable.
You know you talked about theword decide and you know
(32:39):
decision making as well, andthere's also just a little bit
of fatigue on my side ofdecision making and kind of
setting, setting course at times.
And you know this doesn't, if Idon't do it, it doesn't get
done.
You know that, that sort ofthing as well.
And yeah, if we, if we go aftersome new things, what you know
what gets sacrificed as a resultof it.
Speaker 1 (32:56):
I I often I think in those terms as well.
Yeah, that makes a lot of sense.
What's the saying?
It's like there are nosolutions or perfect solutions.
Something's effective.
There's no solutions, justtrade-offs.
So any, any, any path thatyou're taking, you're gonna have
to consider the trade-offs.
Yeah, so, given where you are,you talked about the constraints
.
Like there's like budgetconstraints or time constraints.
(33:17):
There's attention constraints.
Um, you know, we've explored abit about just like the
challenge of coming up withreally good ideas, but like not
necessarily moving on them.
I wonder if we can sort of like, given all that, all that like
maybe take a step back.
And I'm taking a moment to sortof sense what the question is
(33:40):
what does it look like for youto just enjoy all this?
You've got a lot of thingsgoing on.
I'm curious, like you'reconstructing your days, your
weeks or months.
What does this all look likefor you when you're enjoying it
all?
Speaker 2 (33:52):
I am enjoying it all right now and maybe there's a
little bit of guilt around thattoo I mean like having this
feels, it feels like I have goodbalance right now, as I said,
between me, family and and in away, there's not this massive
problem to solve or you knowthing, for what's been
(34:14):
challenging to understand iswhere we are now is not where
the vision was, but it issomewhere that's nice and stable
, and all that with the family.
So, yeah, I think my day-to-dayis quite enjoyable and I'm
working generally on the thingsI want to work on.
Um, and we're here todaybecause, uh, you know, I, I
(34:41):
there could be other stuff towork on, but I don't really uh
want to sacrifice the otherthings to do them yeah, what?
Speaker 1 (34:55):
what would change if you just gave your, gave
yourself permission to enjoywhere you are right now?
Speaker 2 (35:01):
yeah, just letting go a little bit of the of the new
ideas, you know, just looking atwhat's working and really
focusing on that and not tryingto innovate and do a lot of new
things in the business.
Just look at the the work we'veput in over the last years and
accept that that's what's goingto get us to the next phase.
(35:24):
It's not going to be some new,innovative, wild idea that's
going to require working allweekend.
So, uh, yeah, I think I thinkthat's definitely possible,
saying no more instead of maybelater.
Speaker 1 (35:40):
Yeah, if you did more of that, how would it feel?
Speaker 2 (35:44):
Yeah, I'd still be probably a little bugged at
times of missing out on things,but I think we have.
I have taken that approach inrecent times, as in, let's say,
six months or so, once we reallystarted focusing and became
more financially stable as acompany.
(36:04):
I did enjoy that period andthat different mindset.
So maybe it's a little bitcoming out of that Not even
coming out of it, but maybe it'shaving enjoyed that for a while
but all of a sudden I'mthinking, well, let's do
something else, let's do more.
This has been nice, you knowagain like I have a seven month
old son and I would say work hasnot overly taxed me over the
(36:28):
last seven months, which hasbeen great.
That's why I have somehow havebalance.
So, but but what I wrestle withis, um, just getting out of
that, getting out of thatbalance and having having the
FOMO that we described.
Speaker 1 (36:42):
Yeah.
Speaker 2 (36:43):
I get that.
Speaker 1 (36:43):
I'm just going to share this because it came up
for me.
Part of our conversation mademe think about sports and
athletics.
And so you know, when youconsider how athletes train,
there's going to be periods ofintense training and sprinting
and there's going to be anoverreaching, and then there
also has to be this rest andrecovery, you know.
(37:04):
And then that's where theadaptation takes place, and then
so the capacity sort of buildsover time.
It occurs to me and I couldjust totally be projecting a
bunch of stuff here but itoccurs to me that you've spent
the last five years like pushingand grinding and like going
really hard, and now you'vefound yourself in this place
where it's like, oh, we're sortof resting and this feels weird
(37:27):
and we shouldn't be doing it.
And it makes me wonder how muchof the most recent period and
the current period is also thecollective system sort of
building more capacity so thatit can go into the next sprint
later on.
You just don't know when it'sgoing to be.
Speaker 2 (37:44):
I think that's very well said.
You probably didn't know this,but I was a Division I college
athlete.
Speaker 1 (37:51):
I did not know that.
Speaker 2 (37:53):
Yeah, so I definitely understand and I think that's
part of my part of my processhere.
You know, as you said, is theuh, the intensity and the rest
and recovery, and yeah, I hadn'tthought of it in that kind of
direct way that that you havethat maybe I am just getting out
of the rest and recovery phasewhich coincided with the birth
(38:13):
of a child, but also it was alsoit was a time in the company
when we had really focused andnarrowed.
You know what we were, what wewere doing, so the timing just
might be aligned.
But it's actually, you know asmuch about the business as my,
my personal timing, yeah, and itcould be, could be that time
where, operationally, thingshave have become sound and we
could have the capacity to breakthrough.
(38:34):
So maybe that's the hunger thatI have right now that I don't
know if it's the right thing toexplore, as we've discussed here
the whole time.
Speaker 1 (38:43):
Yeah, I don't know the details about the hunger,
but it's interesting that yousaid I don't know if it's the
right thing to explore.
I'm personally wondering whatit would look like if you
allowed yourself to follow thehunger for a bit and just see
where it would take you.
Speaker 2 (38:57):
Yeah, yeah, I think in a way it's a similar answer
to what is, what is the downside, and you know the risk that
I've been talking about.
So I think pursuing the hungeralso could lead to losing the
balance that I have and justfeeling like I'm letting
(39:18):
something dissipate that isstrong right now.
I don't know what that is.
Again, we talked very generallyabout personal, family and
business, but there's a lot morenuance than that.
So, yeah, I think I thinkpursuing the hunger in a
efficient way, that's uh, youknow, I think that's where where
(39:42):
it's going, um, not notnecessarily like a crazy
aggressive way, but um, how dowe do it smartly?
And you know it still leads topotentially giving up
opportunities that um couldexist in different, with a
different level of aggression,but there's probably still some
(40:03):
ways to have that outlet.
Pursue the hunger, yeah, youknow, I guess I guess not pursue
hunger, but to follow it.
Speaker 1 (40:11):
Yeah, to listen to it .
You know we've kind of touchedon this a little bit already,
but a few times now Will you'vesaid something to the effect of
not wanting to let that thentake over your time.
Speaker 2 (40:38):
no-transcript yeah, I think it's less about like
sacrificing other things.
I don't think I'll let myselfdo that.
I think I would probablymaintain the balance.
So what probably getssacrificed is the pursuit of the
ideas in a way.
So if I'm I'm all in on a brandnew idea and spending all my
(41:01):
time there, eventually the otherstuff's just going to creep up
and I'm going to have to startaddressing everything else
that's going on, and then maybethe idea gets deprioritized
again.
Maybe what the end result wouldbe if I really went astray from
my normal day-to-day and wentafter these ideas, I think I'd
probably just sort of end upback where I am now, unless
(41:24):
there was this like incredibleresult.
And then maybe you, you shiftgears and everything.
You know things change, but whoknows, right, I don't know that
that'd be the likely outcomeyeah, so is it?
Speaker 1 (41:35):
the idea then is like , oh, I, you would explore,
you're looking at the differentpotential, and then you like
reach a point where you're like,hmm, like I gotta go back to
all the other stuff that'sasking for my attention, those
are my top priority.
And so it's like, well, there'sno reason to explore this now,
because I can't push it further.
I got to go back to my othercommitments.
Speaker 2 (41:57):
That's the concern, yeah.
Speaker 1 (41:59):
Yeah, how much have you allowed yourself to even try
that?
Speaker 2 (42:03):
I have a little bit.
I mean, there's some tacticalthings we don't, you know, have
to get specifically into.
But you know, we have taken afew risks over the last three to
six months in the business thathave led to a shift, you know,
of some sort.
It's happening, you know, butit's very calculated and again I
think that's fine.
But that is what I'm wrestlingwith.
(42:25):
It's just this level of riskand how that fluctuates all the
time, right, depending oneverything going on around you.
Speaker 1 (42:33):
Yeah, it's a lot to keep in your head, especially in
a quickly changing environment.
Yeah, sorry, you were about tosay something.
Speaker 2 (42:41):
Well, I was going to say I mean, I said I wouldn't
get tactically into it, but justmaybe it'll help understand
Like, we hired a consultant forthe first time in the company's
history recently you know, somepeople love consultants, I
haven't hired one before and wehired one and uncovered some
things and sort of shifted thepath and like so that was a
(43:02):
positive outcome from it to thepath and like so that was a
positive outcome from it.
Um, but it wasn't a uh, youknow somebody that we knew
personally and and had workedwith before in other capacities,
and so it felt like acalculated risk, um, to pay
somebody a lot of money just tolook at what's going on.
Um, so that that was theexample that really came to mind
(43:24):
of okay, we actually are goingto shift some things we're doing
because we pursued something wehadn't done before.
Speaker 1 (43:32):
Yeah, if we had more time, there's like a thread in
there I'd really want to pullaround, like the topic of like
change, like how do we allow asystem to change and and what
conditions are required for usto allow that.
But that's a maybe a time for adifferent, a different uh
(43:53):
conversation, and so just as westart to wrap, then I let me
just ask then will I'm curiouswhat, what things you're taking
away from from the explorationtoday.
I'm curious if there's anythingyou want to underscore there
yeah, uh, I have a lot to takeaway.
Speaker 2 (44:06):
for sure it's been, it's very interesting.
But yeah, I guess the like theway, the way different
constraints kind of impact, howI think about the path to take
and just acknowledging whatthose constraints are and and
sort of kind of uh workingwithin them, uh, in a way, and
(44:30):
that being okay, um, you know, Ithink it's just uh, uh.
It would be a different way ofof thinking um for me, as
opposed to thinking so so bigthat there's, there's so much to
pursue.
Um, uh as well.
Yeah, okay, can I put thequestion back to you too?
(44:50):
Can I some takeaways from fromyour end?
Speaker 1 (44:55):
I'll offer me some what I noticed.
I think what I noticed inspeaking to you is, um, there's
like you is, there's likethere's like this kid in a candy
store sort of thing.
You're like I can see it.
You're like, oh, you're like soexcited about all the different
(45:15):
things that are possible and,like a kid in a candy store, you
can't have all of it, Right,You'll just get sick.
And so, yeah, I'm just sort offeeling into what's coming up.
It's like, especially in a worldwhere it seems like it's just
(45:39):
noisier over time, there's sortof this maybe sense of, maybe an
illusion of infinite choiceover time.
There's sort of this maybesense of, maybe an illusion of
infinite choice over time.
It occurs to me that that makesit all the more important to
connect with what really matters, and you strike me as someone
who actually has no troubledoing that, Like you strike me
(46:01):
as someone who can really groundhimself in what matters to him
and what he values, and I wouldreally just emphasize that.
So what I would share with youWill, yeah, find ways to
continually connect and stayconnected to those things that
really really matter to you andwhat you want your life to be
(46:22):
about.
It sounds like family is a hugepart of that, of course, but
also many parts of your business.
I trust that you will discoveran infinite number of
possibilities over time with thebusiness, so there'll be no
shortage of that.
And so I think, as long asyou're staying grounded in what
you really care about and youtrust yourself to sort of
(46:43):
explore that, you know that kidin the candy shop thing is not a
bad thing.
I think it's great.
Like, like you know, I thinkElijah have to express that as
well, and and trust that howeveryou navigate is going to be
right for you.
Speaker 2 (46:54):
Yep, I appreciate that.
I think it's, I think it's wellsaid.
There's a lot to think about.
A lot of work, a lot workthrough.
You know, as a founder, there'sthere's never a, it's never an
end to your day, right, there'salways a lot of things you leave
on the table to do that day,and that's okay, right, and
there's uh, there's there'scertain things to uh that that
(47:17):
pull you in different directionsand kind of being again okay
with that.
But yeah, I think I think you'reright, I think my I have strong
values.
I'm able to stick to thosegenerally.
Uh, hopefully, the business isis a reflection of that in a way
.
And yeah, I think it's justpart of the part of the process
here.
I'm grateful to be at thisstage where I can say, okay,
(47:39):
we've got a pretty sustainablecompany, at least for one year,
we've done it and, and you know,there's a path to do it for
many years and I'm just figuringout how to be satisfied on that
in that path and, you know,uncover some different stones to
keep it interesting and and andcontinually grow and whatever
growth level is.
And being okay with that, Ithink, is what I'm, what I'm
(47:59):
picking through.
Speaker 1 (48:01):
Yeah, awesome.
Well, I hope you continue toenjoy it.
And, yeah, just continue toenjoy being a dad.
It's pretty clear to me thatyou love doing that.
Speaker 2 (48:10):
Absolutely yeah.
Thanks, brian.
I appreciate the conversation.
Thank you Will.
It was a pleasure.
Speaker 1 (48:14):
Founders often think their main challenges are about
strategy or tactics, but Will'ssession points to something more
personal the inner strugglewith identity and giving
ourselves permission to chooseour own path.
I was really moved by Will'swrestling with whether his
hesitation to pursue everyopportunity might actually be
coming from a place of wisdomrather than weakness.
We explored how, similar to anathlete who needs recovery
(48:36):
periods, this time of businessstability might be building
capacity for future growthrather than holding back.
Throughout our session, willkept circling back to a question
many of us face what kind offounder am I if I prioritize
balance over chasing everypotential opportunity?
As we talked, he seemed to findmore comfort with the idea that
defining success on his ownterms isn't letting anyone down.
(48:59):
It's honoring what matters mostto him.
If you have ever found yourselfcaught between pushing for
growth and maintaining lifebalance, you might ask where am
I measuring myself againstsomeone else's yardstick?
What might change if I trustedthat my current phase is exactly
what my business and life needright now?
I'm Brian Wang.
Thanks for listening and I'llsee you at the next episode of
(49:21):
Slow Down to Speed Up.
Welcome to Slow Down, to Speed Up, where we have real
one-time coaching sessions withstartup founders working
through the challenges ofleadership.
I'm your host and executivecoach, brian Wang.
Today I'm joined by WillPearson, a founder five and a
half years into his journeywho's reached a pivotal
inflection point.
After years of chasing growthand navigating uncertainty,
will's business has finallystabilized.
(00:20):
It's profitable systems are inplace and sustainable growth
continues.
Yet the stability he's longsought brings some unexpected
discomfort too.
With a four-year-old daughterand seven-month-old son at home,
will struggles with the tensionmany founders face but rarely
discuss.
Is maintaining balance betweenwork, family and self actually
okay, or should he be constantlypushing for more growth and
(00:42):
taking bigger risks?
Beneath this practical questionlies a deeper identity
challenge reconciling theentrepreneur's drive to maximize
potential with the reality of afull life outside the business.
During our session, willconfronts how the expectations
he's internalized about being areal founder quote unquote
conflict with the values heholds most dear.
(01:02):
If you've ever felt guilty fornot constantly pushing
boundaries in your business orwondered if you're leaving
opportunity on the table, Ithink you'll find some valuable
perspective here.
Let's dive in.
Hey Will, it's great to see you.
Hey, brian, good to see you.
Thanks for having me,absolutely so.
I'd love to just spend timejust getting to know what are
you bringing in and where are wegoing to take the conversation
(01:24):
today?
Speaker 2 (01:24):
spend time just getting to know what are you
bringing in and where are wegoing to take the conversation
today?
Absolutely Well.
I am a first-time founder, butI'm about five and a half years
into the journey and I feel likeI've hit an inflection point in
the path here and I really wantto get into what is risk as an
entrepreneur and then as afounder and what does that mean
as the business evolves and asyour personal life evolves.
(01:45):
So the other thing I'll addabout myself is, in addition to
a five and a half year oldcompany, I have a four year old
daughter and a seven month oldson, and I think being a dad and
having that become a hugepriority in my life is also
really key to this dilemma I'mhaving of how much to invest in
the business and what kind ofrisks to take around the
(02:06):
business and just kind of howthat relates to everything in my
life really.
Speaker 1 (02:12):
Yeah, I know that for many of us, the way that we
relate to risk changes.
You know, when we're startingto build a family versus when
you're kind of on your own andyou're in your 20s and you know
the world feels very different.
So I'm hearing from you, will.
It's like there's some questionof how to relate to risk.
You know, professionally, withthe business, especially in the
(02:36):
context of raising young kids.
You know, focusing on familyand so on and so forth.
Speaker 2 (02:43):
Yeah, that's right.
And we've really reached thefirst point where I would say
the business is relativelystable.
And you know, the first fourplus years is really focused on
growth, figuring out what do wehave, product market fit, what
is that product?
You know our journey has beenthrough building software,
offering services, differenttypes of services.
Some are very related, some arenot related at all.
(03:03):
You know our journey has beenthrough building software,
offering services, differenttypes of services.
Some are very related, some arenot related at all.
You know we tried a bunch ofdifferent stuff and really in
the interest of unlocking growthand around the four-year mark
we'd made a little bit of ashift because we felt like we
had that focus down, we knewwhat we were good at and it
(03:25):
became more about profitabilityand building a scalable business
and less about chasing growthnumbers.
And that has been prettyeffective over the last year
where we're still growing alittle bit but we are profitable
and it feels like structure'sin place to kind of continue
this business on for a long time.
And that's also sort of a newfeeling.
(03:45):
I've been so much into thisjourney thinking about growth
and just how big can this get,and now I'm a little bit torn of
.
Do I continue to invest or takebig risks and big swings in the
business to see how big it canget, or do I pull back?
And what does that mean formyself and my goals if things
(04:07):
are a little stable and I allowit to be stable?
I've never really thought aboutthat stage, but I'm
experiencing it right now.
Speaker 1 (04:14):
Okay, so I get the sense that being in this more
stable era let's call it feels alittle uncomfortable.
Is that an accurate way ofdescribing it?
Speaker 2 (04:24):
It does feel a little uncomfortable and one of the
reasons I brought up my familyinitially is that that is, you
know, anything but stable.
You know just sort of my day today of being around you know my
two young children and seeingthem grow and trying to help
them and develop them.
But, you know, knowing thatthere's a lot of chaos and just,
you know, getting and in thebed, that's a lot to manage on a
(04:46):
daily basis.
Then I get to work and I'm like, okay, this is a little calmer
here.
I don't have a million fires toput out, like maybe I did a few
years ago.
So, yeah, I'm a bituncomfortable and feeling like,
should I be creating a littlebit of that chaos at work as
well in order to, you know, hitthe next level of growth?
(05:06):
Like, what does thatopportunity cost if I'm, if I
don't do that, or should I just,you know, kind of enjoy this
period and let things happen asas they will?
Speaker 1 (05:15):
This might sound like an obvious question, but can I
ask?
So let's say you took some bigrisks and unlocked a lot of that
growth and you know, like thecurve, bending the curve in,
like the significant way, whatdoes that achieve for you?
Speaker 2 (05:28):
I guess it's.
It's more of feeling like I'vehit the potential.
An obvious answer to that forme, you know, I just feel like I
don't want to leave opportunityon the table, and I think
opportunity means a fewdifferent things.
I mean, like the obvious one isis financial reasons.
Um, you know, of course, if I10 X the business, do I 10 X my
(05:52):
net worth?
Like sure, that sounds, thatsounds great.
But you know the otheropportunities just around uh,
you know, as your business getsbigger, just more doors open,
you meet more people, um, youexperience more things like um.
You know I've really enjoyedthat aspect of being a founder
too and the connections I'vemade um over the last five years
.
So I don't want to uh miss outon on those potential
(06:14):
opportunities uh as well.
But it's not a uh, you knowit's not obvious how to do that
either.
Right, like I think to try to10 X uh the business would
require taking a lot of chanceson things that I don't know if
they would work or not, and thatcould be, you know, my, my time
(06:35):
, my money, et cetera.
Speaker 1 (06:37):
Yeah, yeah.
So I just want to reflect onthat, for a second Part of what
makes entrepreneurship somagical is that you like there's
like all this potential right,you use that word potential so
it's like you could make so manythings happen, and it's largely
up to you, and luck obviouslyis a huge part of it too, right,
you know that, and so what Ihear from you will is like, oh,
(07:00):
wow, like we're in a good placenow, but if we, if we made the
right moves, then this thingcould be like man, so much, 10x
bigger, and not even just on themoney component, but who you're
exposed to, who you collidewith, the opportunities that
might generate as a result ofthat effort.
And so there's something thereon the potential, and I hear
(07:23):
there's a tension, tension, atension in that too, which is
like, oh, we don't know how it'sgoing to turn out.
So there's like this riskcomponent to it, right.
And so I'll ask you anotherkind of maybe simple question so
when you consider, like therisk that you're fearing or like
the consequence that you'refearing on the other side of
that, like what does that looklike for you?
Speaker 2 (07:52):
Yeah, it's.
I think it's largely my time isa big thing that comes to mind
and you know, I really want tofind a balance, or have a
balance, you know, between myown mental health, being a dad,
being a founder, being able tomanage all of that, and I feel
like I have pretty good balanceright now.
So my fear is losing control ofthat balance, losing control of
my schedule in order to chasesomething that may or may not
(08:16):
exist in a way.
Speaker 1 (08:21):
What's really interesting about your answer
just now was what you didn't say, which was you didn't say oh
man, I'm afraid it's going tolike tank the business or that
we're going to take these shotsand like they just totally don't
work.
It was really like, oh man, wemight make these moves and it's
gonna demand so much of my timeand attention and knock me out
(08:43):
of balance.
So much of my time andattention and not going to get
out of balance, and so maybeunderneath that, I hear, like
having proper boundaries isreally important to you.
Speaker 2 (08:54):
Does that feel true?
Yeah, definitely, definitely.
And yeah, there is someinherent risk that the business
does suffer and we drop where weare are.
But just given that we are in alittle bit of a stable state, I
guess I'm less concerned aboutthat than you know.
I would have been in the pasthaving this conversation because
I feel like we can, even indifficult times, kind of dig out
(09:16):
of it and, you know, get backto a level of stability again.
Speaker 1 (09:20):
I guess okay, so all right, cool.
So let's say you're, you'remaking some of these moves we
don't have to define thespecific ones, but, like you're,
you're starting to make somechanges.
What is it that makes youbelieve that you won't be able
to own your time and attentionin the way that you want?
Speaker 2 (09:37):
I think what I've found is the growth of the
business has largely beenrelationship based.
You know, we're a B2B business,we're primarily selling
services.
We had a lot of referrals and alot of those referrals have
been kind of long cultivatedrelationships.
So my, my fear there is, if wehave, let's say, you know, 10 to
(10:04):
12 really good partners rightnow that refer us business and
vice versa, if I make that 20 to25 instead, am I the one to do
all of that?
And therefore do I need to beon the road a lot more than I am
?
Do I need to be at every singleconference?
And you know, I think theobvious response to that as well
(10:26):
, why don't you scale this andreplicate that?
And you know, have other peoplethat can do it.
But again, that goes back tothe risk because we haven't
really had other people do it.
It's my co founder and I havemaintained most of these
relationships, yeah, so the riskwould be bringing somebody in
and kind of having them try toreplicate us.
So far there's not evidence sothat we've been able to achieve
that okay.
Speaker 1 (10:48):
So let's just assume for a moment that it is possible
to hire and, you know, train uppeople and other people to like
sort of take some of that onright, um, and if you just
imagine that movie, so like okay, now your team is starting to
like actually step up so theycan scale, I'm curious, like
what's the sort of initialreaction that you have to that
(11:08):
mental image?
Speaker 2 (11:09):
The first reaction is that it's probably going to be
expensive.
You know that risk and would wejeopardize some of the
stability Again kind of goingback to that word by spending
more money?
Again, kind of going back tothat word by spending more money
and then knowing that it takesa while to really cultivate
(11:32):
relationships and figure outwhich ones are interesting and
helpful, it could get that wrongand it could take a while to
get the payback on thatinvestment.
Speaker 1 (11:38):
Yeah, yeah, totally.
So it could cost a lot of money, requires patience.
You might not know if it'sgoing to work out for some time,
right, I hear a lot of that inthere, right, and so what I'm
struck by is, like that there'sthe way I see it, you could kind
of remain where you are, andthere's a familiarity with that,
(11:59):
there's a comfort to that.
And then there's also like theventuring into the unknown.
You're not really sure how it'sgoing to look and feel, where
it's going to lead, right, yeah,I guess, um, one has to
consider, like what would makeit worth it to you, right?
So, like, if you consider, likethe idea of like stepping
(12:21):
beyond where you are now andinto that unknown zone, like I'm
curious for you personally,like what would make that choice
really worth it for you,knowing that you're not sure how
it's going to work out?
Speaker 2 (12:31):
right, yeah, I've never been one of those founders
that starts a company with theintent to make it a
billion-dollar unicorn company.
Being a founder to me has beenabout creating flexibility and
cultivating relationships andhopefully having financial
freedom as a result of that.
And I think the output of whatkind of success looks like in
(12:57):
growing yeah, you'll have toforgive me, that was the
question.
Right, keep going.
Okay, all right, success theoutput here is, yeah, it's.
I guess it's really justhitting the opportunity that
(13:18):
exists out there, maximizing thepotential of the company.
Wouldn't you know if you did?
Yeah, maybe you never do, andthat's the struggle here, I
guess, if I, maybe, I'm kind ofthinking right now that we're
(13:41):
approaching the potential of thecompany and that's why it's
sort of like, okay, are westable now?
Because we've we've got theoperations figured out and you
know this, this kind of steadycourse is going to kind of lead
us there, and going for muchhigher will maybe just lead us
to the same place.
So you know, I don't know ifI'll ever know how high things
(14:02):
can really get, but it feelslike the basics are in place now
and that's again kind of a newuncomfortable feeling for me,
where I've been used to takingwhat I would consider bigger
risks and chances to get higher.
Speaker 1 (14:17):
I'm going to ask you to reach back into memory just
for a moment, because I'mcurious when you look at how you
got to where you are now.
What was a key decision orchoice that you made in recent
memory that got you here?
Speaker 2 (14:29):
Yeah, we've taken outside investment in the form
of equity and debt before, andthat's because the growth
numbers were super, super highand it felt obvious that if we
added money, that we could spendthat money and keep that growth
rate high and maintain ourservices.
And basically we had a stretchwhere the growth slowed down,
(14:54):
even though we were stillspending that kind of money.
And that's really where thetransformation took place of
okay, maybe it's not justspending money, maybe there's
just some other things thatwe're doing, that's making this
work, and it's not all abouttaking on outside investment.
And so now that we're here,like taking a bunch of outside
(15:19):
money, I wouldn't really knowwhat to do with it right now,
whereas I think I knew what todo with it back then because we
were growing so fast and feltlike we had all these holes to
plug.
Speaker 1 (15:30):
Got it Okay.
So it sounds like in recentmemory you've sort of been
focusing on, like, tuning thebusiness.
Like getting recent memory.
You've sort of been focusing ontuning the business, getting
the fundamentals right.
The machine has sort of beenbuilt up in a way, but as it
stands right now, if someonehanded you a whole bucket of
money, you're not really surewhere that would go, necessarily
(15:50):
in terms of generating ameaningful return for the biz.
Is that right?
That's right.
Yeah, like a meaningful returnfor the biz, is that?
Is that right?
Speaker 2 (15:55):
That's right, yeah, and, and you know, when I talk
about my time, my money, as partof the risk here, hiring a
bunch of people, it's somethingwe did before and and some of
them worked out, a lot of themdidn't Right.
So that has led me again, youknow, to this point of how much,
how much risk do we takeknowing that it didn't all work
(16:18):
out before, even though some ofit did?
Speaker 1 (16:22):
Yeah, I just want to empathize with that for a moment
.
I mean, I think it's like a lotof this is trial by error and
experiments.
When you invest a bunch ofmoney into things that don't
(16:44):
work out, it can be really easyto feel like, well, man, I don't
want to take another swing,knowing that the hit rate,
looking back wasn't great.
There's like I have no idea ifit's going to work out.
Speaker 2 (16:49):
There's something that maybe we'll learn, but it
could be costly, yeah, and Iimagine a lot of founders feel
that way, and I imagine a lot offounders feel that way.
You know, you look at yourprevious balance sheets and P&Ls
and you're like, oh my gosh, Ispent millions of dollars on
this.
Like we got nothing out of that.
Yeah, you know, a little bitI'm feeling that.
Or it's not necessarily buyer'sremorse, because you learn a
(17:10):
lot from it and you adjustaccordingly.
But you know really concernedabout making the same mistakes
if they're, if they're notnecessary.
And just you know understandingthis, this new, new reality of
kind of accepting being stableand kind of letting things
happen more, more organicallythan than trying to force it as
(17:31):
we have in the past.
Speaker 1 (17:32):
Okay, so this might sound like a strange question,
but let's say you were single,you didn't have a family,
business was still in the past.
Okay, so this might sound likea strange question, but let's
say you were single, you didn'thave a family, business was
still in the same place as it isnow.
How would that change thiswhole situation, if at all?
Speaker 2 (17:48):
I would probably be more willing to give up my time,
first and foremost, and so Ithink about traveling and going
to conferences and events andthings I don't really enjoy
doing that much because I kindof miss being home right when I
when I'm out and I probably atleast try doing more of that to
(18:08):
see if, to see if it would work.
Speaker 1 (18:12):
Okay.
So there's like this thingabout traveling that feels like
it's necessary to, you know,push the business's growth.
You don't really enjoy it.
You'd actually much rather beat home, but if family weren't
actually the concern, then you'dmaybe go out there and do more
of that.
Speaker 2 (18:30):
Yeah, Because I think the reason I enjoy traveling
generally.
I don't enjoy traveling when itmeans I'm missing moments with
the family, essentially.
Speaker 1 (18:40):
Yeah, that makes sense.
So you're in this place whereyou have two young kids Really
you have an infant at home andof course the natural impulse is
to be there as much as you can.
Then there's just like yeah,but what do we do with the
business sort of thing?
This is not me giving youadvice at all, it's just more of
(19:03):
a curiosity.
So let's say you spent the nextyear or two just really focused
on being a dad, being a husband, enjoying your family as much
as you could and then saying,okay, cool, the business will
evolve as it evolves, I'm notgoing to push it too much over
the next couple of years.
What would have to be true inthat scenario for you to
actually feel satisfied withthat whole setup?
Speaker 2 (19:26):
It's hard to admit that for me It'd be hard to
admit I'm just going to be lessfocused on the business.
I mean, there's a hundredpercent chance.
I have done that over the lastfew years, but I don't really
outwardly say it because italmost feels like I'm letting
the business down, I'm lettingpeople down, letting our
partners down by uh, if I'm not,uh, a hundred percent invested,
(19:52):
um, but you know the way I'vethought about that is 100%
invested, um, but you know theway I've thought about that is
by a hundred percent, has justchanged.
You know the way, the way Ifocus on the business, you know
you're just in terms ofdelegation and focus, you know
as, uh, I think has improved alot because I don't have, you
know, the extra 25 hours on aweekend to work on stuff like I
(20:15):
used to, or I don't choose to, Iguess.
So, yeah, I think that's areasonable approach, but I hate
to cut you off, but I am curious.
Speaker 1 (20:26):
You said like this thing about hating to admit that
.
Can you just say more aboutthat, Like this notion that I
would hate to admit that that'sthe case.
I'm paraphrasing a little bit,but I'm curious if you went into
that a little bit more withthat, what you meant by it.
Speaker 2 (20:43):
Yeah, there's a, there's a vision for the company
that I've sold to people andthey've kind of made their own
investment into it, whetherthat's employment or a
partnership or you know aninvestment my co-founder as well
.
We've communicated a largevision for the company and it's
not there yet.
(21:03):
I don't know if it ever will be, but it's at a stage now that
again, it's stable, but we'renot a household name for every
email marketer in the world.
That was the original goal.
So then, that's why it feelslike it'd be a bit of a letdown
to say, all right, well, I don'treally have that vision now, I
just want it to organically growover the next few years.
(21:25):
Um, yeah, that's why it's a,that's why it's a letdown,
because am I still aiming forthat vision?
And are people really boughtinto the vision?
And all of a sudden, all of asudden, they're not if I tell
them that I'm not.
Speaker 1 (21:38):
Yeah, and I don't want to put words on your mouth.
I don't get the sense thatyou're not bought into it.
I get the sense that you'relike yeah, yeah.
So there's a little bit of athought experiment.
I was running with you, becauseit'd be one thing if you were
like, yeah, I'm just going tocoast guys, I don't get that
(22:00):
sense from you.
My sense is that you want to befully there for your family and
you want to be just ascommitted to your business.
Now maybe the priority hasshifted a little bit,
understandably, right, butyou're still fully committed to
the success of the business andso, yeah, I'm curious about what
it's like when you'reinteracting with your
stakeholders, your team.
You know you talked about thisvision and and they're all sort
(22:21):
of really committed to that.
They're bought into that, like,hmm, I'm sort of seeing what's
coming up.
Like if, if you went to themand you were like, guys, it's
really important to me that I'mthere with my family and like I
want to press this businessforward.
I don't know what it looks likeyet.
Maybe you've had some versionof this already but if you were
(22:41):
to say something to that effect,how, how do you think people
around you would react?
Speaker 2 (22:48):
I think they'd be like well, obviously that's
already happening.
Yeah, but the way you put that,you know I, I took, I took,
took time off when my son wasborn.
If one of my kids is home sick,like I always, you know, I tell
the team because I make sure,you know, I take care of my kid.
My wife works as well like, andshe's, you know, it takes on,
(23:08):
you know, even more with thekids.
But we do it together, we tryto make everything equal and so,
yeah, I think if I just cameout and said it, they'd say we
know you're doing that.
But again, it's just sort oflike this admission that I'm not
all in on the business, eventhough my actions probably show
(23:29):
that I'm all in, but I'm alsoall in on myself and my family
as well.
I don't want to lose sight of,like the, the, the me aspect of
this too.
You know, it's not just familyand business.
Like I do kind of take my ownhealth, you know, physical and
mental, really seriously too aspart of this equation, and I've
done a good job with that, Ithink.
(23:49):
So I wanted to mention that aswell.
But yeah, I mean it's, it's,it's how I act.
So they probably already seethis to a certain extent.
Speaker 1 (23:56):
Yes, how much of this you mentioned like the dilemma
in the beginning of this.
It's how much of the dilemma isguilt that you're not like
1000% on the business becauseyou actually care about yourself
and your, your, your family too.
Speaker 2 (24:13):
Yeah, I guess I don't know if I need to be a thousand
percent.
Yeah, I know it was anexaggeration out there, but yeah
, yeah, I think it's part of it.
I think there's things that I,you know, I'm maybe not, I'm not
doing that, I probably could be, and that's I think.
I think that's what you mean bythat, the, the a thousand
percent there's.
There's opportunities that Ikeep using travel but I think
(24:35):
it's beyond that.
It's it's, you know, certaingrowth and development things in
the business that I can do froma computer in my house that you
know I don't prioritize right.
I work on other stuff, uh,instead of that, and it's it's
it just goes to to what we'retalking about.
For the hours that I doallocate to the business.
(24:56):
I'm super focused and try todelegate as much as I can, but I
do think there's some stuffthat sort of sits at my desk
that I don't do right nowbecause I don't think it's worth
the time that I give thebusiness, that it's worth it to
do it Right right.
Speaker 1 (25:15):
Yeah, I'm pausing because I know we've taken some
twists and turns here, so let mejust come back to you.
I just want to tune in.
So what's the question?
That's still kind of burningfor you at the moment.
Speaker 2 (25:28):
Yeah, it's maybe less about how do we manage risk and
more about just kind of beingcomfortable in a situation where
adding hours to work is not anoption I want to necessarily
(25:48):
explore.
And you know, in a way that'sleaving stuff on the table, as
we just mentioned, but beingokay with that, that sort of
accepting that those thingsbeing left from the table aren't
necessarily going to move theneedle.
It's not like I sit here allday and work on stuff that
doesn't matter.
Right, I'm still working onimportant things, and the other
things maybe I'm not, maybe theyactually don't matter that much
, otherwise I would.
(26:08):
I would be doing them and Ihave to kind of accept that and
feel like I am doing, you know,as as much as I can to to to
allow the business to hit itspotential.
Speaker 1 (26:23):
Yeah, so to to paraphrase what I heard back
from you is is essentially likehow do I, how do I be okay with
the fact that I'm spending thetime I am with the business and
I'm not willing to put more in?
I'm spending the time I am withthe business and I'm not
willing to put more in yeah, Ithink so, yeah.
So what's making?
Again, it's going to sound likea sort of a basic question, but
(26:43):
what's making it not feelingokay right now?
Speaker 2 (26:45):
It doesn't feel.
It doesn't feel okay, becauseit's maybe not what you're
supposed to do as a founder.
You're supposed to.
Yeah, I think, uh, you knowyou're you're, you're supposed
to be really focused on growthand, uh, you know you want to
(27:06):
get everything to be a lotbigger than it is.
Um, and yeah, I guess I'vethought of myself kind of in
that singular focus for so longthat letting that go is
difficult, and what does thatmean for myself and how I think
(27:32):
about myself as a founder andhow I'm running the company?
Speaker 1 (27:37):
You're right that we're as founders.
There's no shortage of people'sideas of what it's supposed to
be and how you're supposed toact and decisions that you make
and so on and so forth.
This might be tricky, but let'ssay you magically stripped out
all other people's ideas of whatyou're supposed to be and how
(27:59):
you're supposed to be doingthings here, like what would
that change for you?
Speaker 2 (28:01):
it's part of it, but I I think what I still would
wrestle with is the never-endinglist of potential opportunities
to grow the business.
It's almost something like myco-founder and I have that list
(28:22):
and we have ideas, and yousometimes just throw something
out of the blue in the middle ofthe night to each other Like,
oh man, if this worked for us,that type of thing.
And then sometimes it requiresthe other person to say, okay,
let's, let's look at this in sixmonths.
Like this is just not somethingwe can do right now.
But sometimes you get reallyexcited about it and you want to
(28:42):
do something and then yourealize it's going to completely
take up all of my time or itrequires a new software or a new
person to do it, and that'swhen I get a little hesitant to
make that investment from there.
So yeah, I know I keep goingback to this theme, but there's
almost an opportunity cost.
Sometimes I feel, when I'm notpursuing all these extra ideas
for the business and that sortof drives me nuts to just let
(29:06):
all that sit there and notnecessarily get attacked not
necessarily get attacked.
Speaker 1 (29:12):
You know 100%.
I just want to stay with thatfor a moment.
Yeah, I think my sense of youis that you have no shortage of
ideas, especially if you'reriffing on them with your
co-founder.
I don't know them, but you'llhave this like infinite well of
a different ideas and plans andand and things that you could
tackle, and yet you have thiskind of limited amount of time,
this finite amount of time in 24hours in a day.
(29:34):
Right, you got to take care ofyourself, your family, and so
what I hear from you Will islike, oh, like the experience of
like coming up with the ideabut then deciding no, no, no,
we're not going to do that rightnow, or we're going to do that
later on or never.
That's like painful, it's like,ah man, like I have to feel
(29:58):
this, like I don't know what.
How would you describe it?
Is it like a disappointment?
Speaker 2 (30:06):
or like what's, what's the feeling of it?
For you?
It's a feeling of it's, it'salmost a loss in a way, like I
yeah I, it's an experience thatI, that I want to have, of just
of trying it and seeing if itworks, and and not having that
experience feels like I'm, youknow, I'm just really missing
out.
I'm losing this opportunity.
Um to to, Hmm.
Speaker 1 (30:27):
Yeah, yeah, yeah.
Um reminds me of, I think, ifyou look at the etymology of the
word decide, I believe it'ssomething to the effect of
killing all the other options.
You choose one course of action, but, like all the other
different paths you could havetaken, you've decided to kill
them essentially, and there's aloss to that.
There's like a grief to thatright, all the lives you could
have lived right, which is partof what makes decisions
(30:50):
difficult at times and makesdecisions difficult at times,
and that's what I hear in you,in what you're describing.
The other thing I think I'mhearing, though, is that there's
some sense of going after oneof those ideas feels really big
(31:10):
in terms of resources or havingto change course on something.
Does that feel true, like whenyou're describing this
experience?
It's oh, this is kind of like abig thing for us to invest in.
Speaker 2 (31:19):
Yeah, absolutely, and that is probably a result of
really tightening things uplately.
So, you know, when I had, whenyou're when you're having
massive growth and you've gotmoney coming in easily from
investors or banks or whateverit's, you know, it felt easier
to try things.
(31:39):
And now, yeah, I think we'rereally focused and, you know,
really tight on budgets, whichis probably a good thing, right.
Speaker 1 (31:50):
But at the same time, there is a little bit of that
experimentation and risk thatyou know it's has been pulled
back I this is a little liketactical, but I wonder, like,
what does it look like for youto make those experiments
smaller, right, in terms of sortof just for the sake of like
exploration and you know whenyou and your co-founder are
(32:12):
riffing, and that sort of thing?
Speaker 2 (32:18):
Yeah, I think, I think we can, I think there.
You know it's like you can'thave a podcast, you don't talk
about AI, right, but obviouslyyou know now, versus a few years
ago, it's a little easier toget started on things with, with
, with those tools that are outthere.
So, yeah, I think it's, I thinkit's, I think it's doable.
You know you talked about theword decide and you know
(32:39):
decision making as well, andthere's also just a little bit
of fatigue on my side ofdecision making and kind of
setting, setting course at times.
And you know this doesn't, if Idon't do it, it doesn't get
done.
You know that, that sort ofthing as well.
And yeah, if we, if we go aftersome new things, what you know
what gets sacrificed as a resultof it.
Speaker 1 (32:56):
I I often I think in those terms as well.
Yeah, that makes a lot of sense.
What's the saying?
It's like there are nosolutions or perfect solutions.
Something's effective.
There's no solutions, justtrade-offs.
So any, any, any path thatyou're taking, you're gonna have
to consider the trade-offs.
Yeah, so, given where you are,you talked about the constraints
.
Like there's like budgetconstraints or time constraints.
(33:17):
There's attention constraints.
Um, you know, we've explored abit about just like the
challenge of coming up withreally good ideas, but like not
necessarily moving on them.
I wonder if we can sort of like, given all that, all that like
maybe take a step back.
And I'm taking a moment to sortof sense what the question is
(33:40):
what does it look like for youto just enjoy all this?
You've got a lot of thingsgoing on.
I'm curious, like you'reconstructing your days, your
weeks or months.
What does this all look likefor you when you're enjoying it
all?
Speaker 2 (33:52):
I am enjoying it all right now and maybe there's a
little bit of guilt around thattoo I mean like having this
feels, it feels like I have goodbalance right now, as I said,
between me, family and and in away, there's not this massive
problem to solve or you knowthing, for what's been
(34:14):
challenging to understand iswhere we are now is not where
the vision was, but it issomewhere that's nice and stable
, and all that with the family.
So, yeah, I think my day-to-dayis quite enjoyable and I'm
working generally on the thingsI want to work on.
Um, and we're here todaybecause, uh, you know, I, I
(34:41):
there could be other stuff towork on, but I don't really uh
want to sacrifice the otherthings to do them yeah, what?
Speaker 1 (34:55):
what would change if you just gave your, gave
yourself permission to enjoywhere you are right now?
Speaker 2 (35:01):
yeah, just letting go a little bit of the of the new
ideas, you know, just looking atwhat's working and really
focusing on that and not tryingto innovate and do a lot of new
things in the business.
Just look at the the work we'veput in over the last years and
accept that that's what's goingto get us to the next phase.
(35:24):
It's not going to be some new,innovative, wild idea that's
going to require working allweekend.
So, uh, yeah, I think I thinkthat's definitely possible,
saying no more instead of maybelater.
Speaker 1 (35:40):
Yeah, if you did more of that, how would it feel?
Speaker 2 (35:44):
Yeah, I'd still be probably a little bugged at
times of missing out on things,but I think we have.
I have taken that approach inrecent times, as in, let's say,
six months or so, once we reallystarted focusing and became
more financially stable as acompany.
(36:04):
I did enjoy that period andthat different mindset.
So maybe it's a little bitcoming out of that Not even
coming out of it, but maybe it'shaving enjoyed that for a while
but all of a sudden I'mthinking, well, let's do
something else, let's do more.
This has been nice, you knowagain like I have a seven month
old son and I would say work hasnot overly taxed me over the
(36:28):
last seven months, which hasbeen great.
That's why I have somehow havebalance.
So, but but what I wrestle withis, um, just getting out of
that, getting out of thatbalance and having having the
FOMO that we described.
Speaker 1 (36:42):
Yeah.
Speaker 2 (36:43):
I get that.
Speaker 1 (36:43):
I'm just going to share this because it came up
for me.
Part of our conversation mademe think about sports and
athletics.
And so you know, when youconsider how athletes train,
there's going to be periods ofintense training and sprinting
and there's going to be anoverreaching, and then there
also has to be this rest andrecovery, you know.
(37:04):
And then that's where theadaptation takes place, and then
so the capacity sort of buildsover time.
It occurs to me and I couldjust totally be projecting a
bunch of stuff here but itoccurs to me that you've spent
the last five years like pushingand grinding and like going
really hard, and now you'vefound yourself in this place
where it's like, oh, we're sortof resting and this feels weird
(37:27):
and we shouldn't be doing it.
And it makes me wonder how muchof the most recent period and
the current period is also thecollective system sort of
building more capacity so thatit can go into the next sprint
later on.
You just don't know when it'sgoing to be.
Speaker 2 (37:44):
I think that's very well said.
You probably didn't know this,but I was a Division I college
athlete.
Speaker 1 (37:51):
I did not know that.
Speaker 2 (37:53):
Yeah, so I definitely understand and I think that's
part of my part of my processhere.
You know, as you said, is theuh, the intensity and the rest
and recovery, and yeah, I hadn'tthought of it in that kind of
direct way that that you havethat maybe I am just getting out
of the rest and recovery phasewhich coincided with the birth
(38:13):
of a child, but also it was alsoit was a time in the company
when we had really focused andnarrowed.
You know what we were, what wewere doing, so the timing just
might be aligned.
But it's actually, you know asmuch about the business as my,
my personal timing, yeah, and itcould be, could be that time
where, operationally, thingshave have become sound and we
could have the capacity to breakthrough.
(38:34):
So maybe that's the hunger thatI have right now that I don't
know if it's the right thing toexplore, as we've discussed here
the whole time.
Speaker 1 (38:43):
Yeah, I don't know the details about the hunger,
but it's interesting that yousaid I don't know if it's the
right thing to explore.
I'm personally wondering whatit would look like if you
allowed yourself to follow thehunger for a bit and just see
where it would take you.
Speaker 2 (38:57):
Yeah, yeah, I think in a way it's a similar answer
to what is, what is the downside, and you know the risk that
I've been talking about.
So I think pursuing the hungeralso could lead to losing the
balance that I have and justfeeling like I'm letting
(39:18):
something dissipate that isstrong right now.
I don't know what that is.
Again, we talked very generallyabout personal, family and
business, but there's a lot morenuance than that.
So, yeah, I think I thinkpursuing the hunger in a
efficient way, that's uh, youknow, I think that's where where
(39:42):
it's going, um, not notnecessarily like a crazy
aggressive way, but um, how dowe do it smartly?
And you know it still leads topotentially giving up
opportunities that um couldexist in different, with a
different level of aggression,but there's probably still some
(40:03):
ways to have that outlet.
Pursue the hunger, yeah, youknow, I guess I guess not pursue
hunger, but to follow it.
Speaker 1 (40:11):
Yeah, to listen to it .
You know we've kind of touchedon this a little bit already,
but a few times now Will you'vesaid something to the effect of
not wanting to let that thentake over your time.
Speaker 2 (40:38):
no-transcript yeah, I think it's less about like
sacrificing other things.
I don't think I'll let myselfdo that.
I think I would probablymaintain the balance.
So what probably getssacrificed is the pursuit of the
ideas in a way.
So if I'm I'm all in on a brandnew idea and spending all my
(41:01):
time there, eventually the otherstuff's just going to creep up
and I'm going to have to startaddressing everything else
that's going on, and then maybethe idea gets deprioritized
again.
Maybe what the end result wouldbe if I really went astray from
my normal day-to-day and wentafter these ideas, I think I'd
probably just sort of end upback where I am now, unless
(41:24):
there was this like incredibleresult.
And then maybe you, you shiftgears and everything.
You know things change, but whoknows, right, I don't know that
that'd be the likely outcomeyeah, so is it?
Speaker 1 (41:35):
the idea then is like , oh, I, you would explore,
you're looking at the differentpotential, and then you like
reach a point where you're like,hmm, like I gotta go back to
all the other stuff that'sasking for my attention, those
are my top priority.
And so it's like, well, there'sno reason to explore this now,
because I can't push it further.
I got to go back to my othercommitments.
Speaker 2 (41:57):
That's the concern, yeah.
Speaker 1 (41:59):
Yeah, how much have you allowed yourself to even try
that?
Speaker 2 (42:03):
I have a little bit.
I mean, there's some tacticalthings we don't, you know, have
to get specifically into.
But you know, we have taken afew risks over the last three to
six months in the business thathave led to a shift, you know,
of some sort.
It's happening, you know, butit's very calculated and again I
think that's fine.
But that is what I'm wrestlingwith.
(42:25):
It's just this level of riskand how that fluctuates all the
time, right, depending oneverything going on around you.
Speaker 1 (42:33):
Yeah, it's a lot to keep in your head, especially in
a quickly changing environment.
Yeah, sorry, you were about tosay something.
Speaker 2 (42:41):
Well, I was going to say I mean, I said I wouldn't
get tactically into it, but justmaybe it'll help understand
Like, we hired a consultant forthe first time in the company's
history recently you know, somepeople love consultants, I
haven't hired one before and wehired one and uncovered some
things and sort of shifted thepath and like so that was a
(43:02):
positive outcome from it to thepath and like so that was a
positive outcome from it.
Um, but it wasn't a uh, youknow somebody that we knew
personally and and had workedwith before in other capacities,
and so it felt like acalculated risk, um, to pay
somebody a lot of money just tolook at what's going on.
Um, so that that was theexample that really came to mind
(43:24):
of okay, we actually are goingto shift some things we're doing
because we pursued something wehadn't done before.
Speaker 1 (43:32):
Yeah, if we had more time, there's like a thread in
there I'd really want to pullaround, like the topic of like
change, like how do we allow asystem to change and and what
conditions are required for usto allow that.
But that's a maybe a time for adifferent, a different uh
(43:53):
conversation, and so just as westart to wrap, then I let me
just ask then will I'm curiouswhat, what things you're taking
away from from the explorationtoday.
I'm curious if there's anythingyou want to underscore there
yeah, uh, I have a lot to takeaway.
Speaker 2 (44:06):
for sure it's been, it's very interesting.
But yeah, I guess the like theway, the way different
constraints kind of impact, howI think about the path to take
and just acknowledging whatthose constraints are and and
sort of kind of uh workingwithin them, uh, in a way, and
(44:30):
that being okay, um, you know, Ithink it's just uh, uh.
It would be a different way ofof thinking um for me, as
opposed to thinking so so bigthat there's, there's so much to
pursue.
Um, uh as well.
Yeah, okay, can I put thequestion back to you too?
(44:50):
Can I some takeaways from fromyour end?
Speaker 1 (44:55):
I'll offer me some what I noticed.
I think what I noticed inspeaking to you is, um, there's
like you is, there's likethere's like this kid in a candy
store sort of thing.
You're like I can see it.
You're like, oh, you're like soexcited about all the different
(45:15):
things that are possible and,like a kid in a candy store, you
can't have all of it, Right,You'll just get sick.
And so, yeah, I'm just sort offeeling into what's coming up.
It's like, especially in a worldwhere it seems like it's just
(45:39):
noisier over time, there's sortof this maybe sense of, maybe an
illusion of infinite choiceover time.
There's sort of this maybesense of, maybe an illusion of
infinite choice over time.
It occurs to me that that makesit all the more important to
connect with what really matters, and you strike me as someone
who actually has no troubledoing that, Like you strike me
(46:01):
as someone who can really groundhimself in what matters to him
and what he values, and I wouldreally just emphasize that.
So what I would share with youWill, yeah, find ways to
continually connect and stayconnected to those things that
really really matter to you andwhat you want your life to be
(46:22):
about.
It sounds like family is a hugepart of that, of course, but
also many parts of your business.
I trust that you will discoveran infinite number of
possibilities over time with thebusiness, so there'll be no
shortage of that.
And so I think, as long asyou're staying grounded in what
you really care about and youtrust yourself to sort of
(46:43):
explore that, you know that kidin the candy shop thing is not a
bad thing.
I think it's great.
Like, like you know, I thinkElijah have to express that as
well, and and trust that howeveryou navigate is going to be
right for you.
Speaker 2 (46:54):
Yep, I appreciate that.
I think it's, I think it's wellsaid.
There's a lot to think about.
A lot of work, a lot workthrough.
You know, as a founder, there'sthere's never a, it's never an
end to your day, right, there'salways a lot of things you leave
on the table to do that day,and that's okay, right, and
there's uh, there's there'scertain things to uh that that
(47:17):
pull you in different directionsand kind of being again okay
with that.
But yeah, I think I think you'reright, I think my I have strong
values.
I'm able to stick to thosegenerally.
Uh, hopefully, the business isis a reflection of that in a way
.
And yeah, I think it's justpart of the part of the process
here.
I'm grateful to be at thisstage where I can say, okay,
(47:39):
we've got a pretty sustainablecompany, at least for one year,
we've done it and, and you know,there's a path to do it for
many years and I'm just figuringout how to be satisfied on that
in that path and, you know,uncover some different stones to
keep it interesting and and andcontinually grow and whatever
growth level is.
And being okay with that, Ithink, is what I'm, what I'm
(47:59):
picking through.
Speaker 1 (48:01):
Yeah, awesome.
Well, I hope you continue toenjoy it.
And, yeah, just continue toenjoy being a dad.
It's pretty clear to me thatyou love doing that.
Speaker 2 (48:10):
Absolutely yeah.
Thanks, brian.
I appreciate the conversation.
Thank you Will.
It was a pleasure.
Speaker 1 (48:14):
Founders often think their main challenges are about
strategy or tactics, but Will'ssession points to something more
personal the inner strugglewith identity and giving
ourselves permission to chooseour own path.
I was really moved by Will'swrestling with whether his
hesitation to pursue everyopportunity might actually be
coming from a place of wisdomrather than weakness.
We explored how, similar to anathlete who needs recovery
(48:36):
periods, this time of businessstability might be building
capacity for future growthrather than holding back.
Throughout our session, willkept circling back to a question
many of us face what kind offounder am I if I prioritize
balance over chasing everypotential opportunity?
As we talked, he seemed to findmore comfort with the idea that
defining success on his ownterms isn't letting anyone down.
(48:59):
It's honoring what matters mostto him.
If you have ever found yourselfcaught between pushing for
growth and maintaining lifebalance, you might ask where am
I measuring myself againstsomeone else's yardstick?
What might change if I trustedthat my current phase is exactly
what my business and life needright now?
I'm Brian Wang.
Thanks for listening and I'llsee you at the next episode of
(49:21):
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