January 7, 2025 • 50 mins
When is your protective instinct trying to tell you something important? In this coaching session, an experienced founder shares their internal struggle with fundraising - not because they can't raise money, but because something deeper is holding them back.
We uncover how past experiences of loss and betrayal shape our present choices, and how what feels like resistance might actually be wisdom. This conversation opens up crucial questions about control, growth, and staying true to your vision while building a venture-scale company.
Whether you're currently fundraising or not, this episode offers valuable insights about how to interpret and work with your protective instincts as a founder.
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
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Speaker 1 (00:00):
Welcome to Slow Down and 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's episode is specialwe're featuring our first
anonymous guest, who we'll callJohn.
In our session, john brings upone of the most profound
tensions in entrepreneurship therelationship between control
and growth.
When you take venture capital,you're making a devil's bargain,
(00:23):
trading away pieces of yourcompany's destiny for the fuel
to grow faster.
John has been in startups over adecade, building multiple
companies.
Now with a thriving businessthat may not need investment,
he's wrestling with this verydilemma.
But every time they sit downwith investors, something
visceral takes over.
He has this internal reactionthat says get away from my
business.
And John is afraid thisreaction is holding him back.
(00:44):
That's why he's here toconfront the emotional scar
tissue from past rejections andthe pressure to keep control
over his vision.
Together we explore the pushand pull of staying independent
versus raising money, his deeproot of fears of compromise and
that fierce protective instinctmany founders feel toward their
vision.
Through our session, john beginsto uncover what it means to
approach these investorinteractions from a place of
(01:04):
strength, not fear.
This is a powerful session onreconnecting with the core
vision, navigating vulnerabilityand redefining what it means to
stay open while protecting whatmatters most.
I hope you enjoy it.
Hey, john, it's great to bewith you today.
Thanks for having me.
Yeah, so we spoke a little bitabout what you want to get into
today, but why don't you spend alittle bit of time sharing what
(01:29):
you're bringing in and what youwant to explore as we sit down
together?
Speaker 2 (01:31):
in tech, starting companies or having jobs at
different kind of startups phasecompanies for my whole career,
which is over 10 years, and I'velearned a lot in that time.
For sure, at the beginning ofmy career, I was very ambitious.
(01:54):
I was like kind of one of thoseright out of college
entrepreneurs and I got a lot ofrejection from investors and I
think now I'm in a much betterposition.
My company has, I've got a lotmore experience in my career,
I'm feeling a lot more confidentand even the company that I
have founded and I'm working onnow is in a good spot where we
(02:15):
may not even really needinvestment but it feels like it
would help us grow and it'sdefinitely like we're down the
venture path and I'm happy withthat path and I really liked
that path, um.
So I'm thinking about what thenext round might look like and,
as I've started talking to someinvestors, a little bit like
kind of building earlyrelationships and, um talking to
our current investors, a lot ofstuff is coming up that I'm
(02:37):
realizing would be helpful forme to explore around kind of um
scar tissue I think that Iformed, especially early in my
career and some more recentaround rejection Not only from
investors, but kind of likespecifically from investors is
probably the best place to focusit, and just the feeling of
like being kind of misunderstoodor underestimated or it's so
(03:02):
frustrating that people don'tsee what you see and people
don't get it.
And I think part of what happensI've realized is I found that I
feel a little tense sometimesin those conversations.
I feel like it's actuallyreally hard for me to develop a
lot of warm feelings or evenlike respect sometimes when I'm
(03:22):
talking to investors feelings oreven like respect.
Sometimes when I'm talking toinvestors, I kind of look, I
don't look down on them, but Ijust find it hard to um, I think
I went through a phase earlierin my career where I probably
put them too much on a pedestaland now I'm probably doing too
much the opposite.
It's like investors reallydon't know anything at all and
they're here for, like my kindof a thing yeah.
Speaker 1 (03:39):
Yeah, no offense to any investors listening to this
right now.
Speaker 2 (03:48):
Yeah and and um, you know, they know some things.
There's some investors that arereally great to work with.
Of course, like intellectuallyI know that, but emotionally in
the moment, when I'm talking toan investor and I'm realizing,
like in the moment, I'm kind oflike losing respect for them.
They're not really following,they're not keeping up, uh, it's
, it's I, I sort of pre-rejectthem before they have a chance
to reject me, which is a commonuh, I think, uh, emotional
survival strategy that happenswhen people have been through
rejection is, it's, like youknow, once bitten, twice shy, or
whatever.
(04:08):
Like you know, I'll reject youbefore you can reject me, kind
of a thing.
And I feel like it wouldprobably be useful for me to
talk through a lot of this stuffso that I can go through
whatever fundraise process mayhappen at some point in the
nearish future more balanced,more more grounded, more open to
people, just being awesomebecause there are a lot of
(04:29):
awesome investors out there andalso like, yeah, there are
certainly not great investors,but not to, like you know, have
it really affect me so much ifsomeone, uh, just you know,
isn't picking up what I'mputting down in conversation,
it's not necessarily anindictment of me or them.
It's just not fit, probably,and it's totally fine um so, uh,
probably.
(04:49):
The one last thing I'll put onthis is um, and I think, overall
, this is a healthy thing, butit's interesting to think
through is um.
I think one layer deeper islike how this feeling of like a
fundraise is going to be hardemotionally affects my overall
strategy.
Because I think there is um aworld, you know, in 2021 and
(05:13):
around then, when people werejust raising enormous sums
really easily seemingly, and, um, kind of messing up for
companies in the process, yeah,with enormous valuations, and I
definitely don't want to do that.
But I think there's also it ispossible, especially if you are
like committed to the venturepath, to go too far, to the
other extreme, where you're justyou're in survival mode, you're
in cockroach mode and thecompany it's kind of like too
(05:35):
hungry to eat, kind of a thingwhere you don't have enough
resources to actually like doyour plan yeah there's like this
pure scarcity thing going onyour plan.
Yeah, there's like this purescarcity thing going on, exactly
, and so I think there's part ofit is about just I want to go
into a fundraise process, um youknow, with good chances of
building great relationships andresonating with good people and
(05:55):
all that kind of stuff andgetting the capital.
I need or want to acceleratethe business.
But also there's kind of thisfeeling of like, what if I
didn't think a fundraiser wassuch a?
you know, alternating betweenannoying and frustrating or
scary thing, and I thought of itmore as something that could be
, uh, a useful, like more of anoption.
(06:15):
It's like it's a.
It's a not an easy optionnecessarily, but like, uh, it's.
Speaker 1 (06:19):
it's not like a dark corner of the entrepreneurship
journey, it's more of like, yeah, that's a thing that's totally
there and doesn't have to wedon't have to shape our whole
strategy around avoiding needingto do it or something.
Yeah, I mean wow, so.
So there's a lot to unpack inwhat you just shared.
Um and so like, in noparticular order.
I just want to reflect a littlebit before we dive in.
(06:42):
I know I know a lot of founderswho can relate to exactly what
you're describing, john, thiswhole sense of like wow, like
fundraising as a function of thefounder seat.
The CEO seat is dark and scaryand painful and terrible, and
it's interesting because Iactually know quite a few
founders who enjoy it.
They take delight in it andit's fascinating.
Speaker 2 (07:03):
It's like the total opposite.
For some people they're likereally good at fundraising, and
sometimes there's people who areamazing at fundraising and like
not so good at the other partsof running a company.
That's right, that's right.
Yeah, the opposite problem theyshould be more great at both.
Speaker 1 (07:14):
Yeah, that's right.
And I bring that up becausewhat occurs to me is that it's
possible to inhabit and embodydifferent orientations and
perspectives on that whole thing, right.
And when I go back to what youwere sharing, john, this whole
sense of I mean the first, thefirst thing that strikes me as,
(07:35):
as I'm listening to you, is thatyou're really well aware of
yourself in terms of the mental,emotional patterns that you
have.
You mentioned scar tissue.
You're even very articulate indescribing yeah, there's some
self-defense going on there,defensive reactions there, yeah,
right.
(07:55):
And so my intuition tells methat what we'll look at is
probably going to go a littlebit underneath that surface,
like below, just like theintellectual, cognitive knowing
of it.
But maybe, just to set thestage here for a moment, if we
can just articulate it, like ifyou were to go and just define
(08:18):
in words the attitude that youwant to bring into a fundraise,
how would you describe it?
Speaker 2 (08:28):
Great question.
Um, I would say openness tofeedback, while at the same time
not it doesn't necessarilychange our plans, but it's there
could be interesting stuffthat's worth looking into deeper
or doing something with.
Know.
Um, I would say openness tosome investors being really
(08:51):
great and have being like areally positive force for the
trajectory of the company yeah,um, and at the same time,
handling people who clearlyaren't, because I'm going to
encounter them with a bit oflike, it doesn't ruin my day and
it's not so annoying that Ihave to deal with these people
and whatever it's just like yeahthere's going to be some people
who aren't in a good positionto be a positive force for our
(09:13):
company, and the cost of findingthe ones who are is to talk to
some of the ones who aren't.
It's like interviewing employees.
You know, it's not nearly asstressful to interview 20
candidates for a role and have15 of them not really be in the
running in a serious way.
Uh, for whatever reason, talkingto 20 investors and having 15
(09:33):
of them like not get it.
I think it's because implicitlyit's it doesn't feel like I'm
in power.
Uh, tell me more about that.
Well, if I have a budget tohire someone and it's my choice
who to hire like finding peoplewho aren't qualified but, you
know, having a phone screen withthem or whatever, where I kind
(09:53):
of quickly figure out they'reprobably not right for the role,
I just feel totally comfortable.
I feel in the driver's seat.
Maybe there's something to learnabout like our screening
process or whatever else, butlike it's not a huge deal at all
, Right yeah about like ourscreening process or whatever
else, but like it's not a hugedeal at all, right yeah.
But, um, if it feels like, wow,you know, maybe we don't need
this money, but this money wouldbe really useful, um and uh,
(10:16):
but it's, you know, it's their,it's their money, it's their,
their sort of hiring forfounders, in a way, right, it's
kind of like the mental modelthey have the budget but they're
deciding where to spend it interms of capital and in terms of
time that they spend withcompanies, and it feels like I
don't expect.
(10:36):
I mean, it's possible.
I haven't really, in anyserious way, gone to market with
this idea yet.
Sometimes, when you do, youfind yourself in a competitive
bid, and it's kind of you.
Do you know?
Like you find yourself in acompetitive bid, it's kind of
you and you're more like theperson with the budget making
the hire.
Speaker 1 (10:48):
Usually the case is, though, you're kind of you're
more making the sale, at leastfor the first part, right okay,
so there's a sense that whenyou're in that pitch or in that
conversation, they have more ofthe power.
Uh, it's just a the kind oflike gross generalization, but
that's how it feels.
Speaker 2 (11:04):
Exactly that's how it feels but it's funny because
it's kind of like, as soon as Isay that I'm like, why am I
giving them that?
Why are you giving them?
Speaker 1 (11:13):
that.
Let's just, let's take thatseriously.
Why are you giving them that um?
Speaker 2 (11:22):
I think, um, I think it's really funny because what's
coming to mind is that myinstinct is to.
I desperately don't want togive them that, and I feel like
the only way to not give themthat is to just build a company
that's growing incrediblyquickly and is profitable, so
(11:42):
that we don't need to raisemoney.
But we might choose to, but wedon't need to, and so every
fiber of my being wants to focuson that.
Yeah, and I probably would growa little bit slower and the
company might not be off to anamazing trajectory if I did that
versus was willing or able orwhatever to raise a little bit
(12:05):
more, ahead of some of thoselike oh, yeah, we're already
profitable and we don't need youat all, but just to be able to
go into those conversations like, yeah, like we're growing
really fast, we've proven a lotof stuff, but like we're not
profitable because we chose tospend more, because we chose to
invest in growing faster,because we thought we'd have a
great chance of raising moneyand we could always dial it back
.
It's not existential kind of athing, but if you operate in a
(12:29):
little bit more of a fear-basedway, then you don't make the
investments because you'reavoiding being in a position
where you sort of quote needmoney and there's varying
degrees of need, but pushing itmore into the yellow zone.
We never want to get to the redzone.
The green zone is like you know, we raised two and a half
million and we have two millionin the bank still two years
later, or whatever.
Sure, but like, basically, ifyou push it a little bit more to
(12:50):
the yellow zone, we're likebecause we've got lots of ideas
we could probably hire a littlebit more aggressively or spend a
little bit more aggressively topursue some of those ideas, or
pursue the same set of ideas ina sort of more comprehensive way
or bigger way, the same set ofideas in a sort of more
comprehensive way or bigger way.
Um, yeah, it's.
(13:10):
I do think a pattern that I'veseen is a lot of founders push
it a little bit more into theyellow zone, not risking death
of the company, but anyway, it'sinteresting.
You can kind of see the, the,the, the loop that goes between.
It's the way I operate thecompany, based on the way I want
to relate to investors, where Iwant to have the power in those
conversations, based on the wayI want to relate to investors
or I want to have the power inthose conversations.
Speaker 1 (13:24):
So I think what you're describing is a very real
dynamic.
What I will assert is that itdoesn't have to be that way, and
maybe what I would say on topof that is it doesn't have to be
so, dictated by the externalcircumstances is the premise
I'll start with.
I know founders who they go outfundraising and they have five
(13:48):
months of runway to like theiryellow-red zone.
Speaker 2 (13:52):
I'll call five months red, yeah, yeah.
Yeah, I'll call very red.
Yeah, it depends on your riskprofile.
Speaker 1 (13:58):
But they also can go out with this openness that
you're describing.
Yeah, and without this sense ofthis person really has power
over me, yeah, right, and so I'mcurious for you if we take a
look, what is it that you'rebelieving about yourself in that
(14:18):
interaction?
That's saying this personreally has power over me.
I don't have the power, sayingthis person really has power
over me.
Speaker 2 (14:28):
I don't have the power.
The extent to which I feel liketheir choice dictates whether I
get to keep working on thiscompany or not, probably, and so
that's why I'm like I justreally love doing it.
I really want to keep workingon this for a long time.
I've had a lot of things in mycareer that I've loved working
on, but for one reason oranother I wasn't able to see it
through to the extent that Ireally wanted to.
Speaker 1 (14:50):
Let me pause for a second though.
Yeah, so I just want to zoom inon that.
You said there's this sensethat it's up to this person on
whether or not I get to continueworking on this.
Speaker 2 (15:01):
Well, not this person , but I need someone to say yes
kind of a thing, not any oneperson, but I need.
I need someone to say yes kindof a thing, not any one
particular person, but you needsomeone to say yes to keep going
.
That sense that it's not justabout anymore my choices, about,
like, my ability to build aproduct that generates enough
revenue to sustain the team andthe infrastructure necessary to
keep running the thing.
Yeah, it's about outsideinvestment needs to come in for
(15:23):
this thing to continue there's areal dependency.
Speaker 1 (15:25):
Yeah, yeah, it's a very, it's a very real, like
brass tacks, yes, like we'redependent on external capital,
uh, like in this scenario thatwe're constructing in order for
us to continue.
Yeah, exactly.
And so in that world where,like, let's say like, yeah,
objectively, there is thisdependency, let's just call it
that I would imagine thatthere's like a certain sense of
vulnerability that comes withthat totally totally and what's
(15:48):
that like for?
Speaker 2 (15:49):
you, um, a heightened one for me because, uh, my last
company or a previous company,not my very last company, but in
in my past I've had a companythat I love working on and I
really believed in, and you know, we raised a pre-seed but we
couldn't raise a seed and so wejust ran out of cash and it was
(16:11):
like my bank account was empty,the company bank account was
empty.
There was nothing I could doexcept for try and sell it for
scraps and like go get a job,basically, yeah, and lay
everybody off and shut down theservice and all that kind of
stuff.
And it just was heart-wrenchingbecause I love that thing and I
wanted to keep working on it,but I just didn't.
Money, you know, like I had tobe able to pay rent and I had to
(16:32):
.
You know, I couldn't find anyother way.
I was sort of the other thingis by the end of it because I
focused the last you know monthsof the company's life on
fundraising.
Of course, you know, knowthat's kind of uh, it's too late
and I was like out of energyand like it's, it's always
possible, like now I feel likeI'm in a much better spot where
I'm like, okay, I'm never gonnalet it get to that point again,
(16:54):
sure, but even then it's kind ofand it's it's good that I'm
technical so I can kind of likejust keep the thing running
myself and take it down to likeskeleton crew for a little while
, sure, um, so I don't reallyfeel like that this has a chance
of that happening again.
But that was a deep scar tissueof just like it was so sad to
not be able to work on thatthing anymore and to have to go
get the job you know yeah, Itotally get that.
Speaker 1 (17:16):
I totally get that.
I've been through that.
I know many people have beenthrough that.
And if we go back to how westarted this, you talked about a
desire to go into theseconversations with openness,
with the.
You know, there's like anopenness to really connecting to
the person in front of you.
Um, not letting the feedback,whether whatever it is like,
(17:39):
sway you too much.
Speaker 2 (17:40):
Yeah, take me evenly the same way I would take
feedback from like a friend butthat's the feeling is, if a
friend tells me some stuff thatI don't think is great advice,
I'll either like if, dependingon the type of friend, be candid
with them, like I don't knowabout this for this reasons, or
just, oh, that's a good idea,but either way it doesn't really
affect my mood too much and I'mable to be pretty open and
process the information that isin front of me in like an even
(18:01):
way or like same thing.
Speaker 1 (18:02):
If an employee or you know, uh, yeah investor it's
different so how much of thatemotional scar tissue that
you're referring to earlier iscoloring the present around
taking these things, you knowpersonally um, I mean, yeah, I
feel like that's the whole thingright.
Speaker 2 (18:21):
It's basically like I've been in this situation
before.
You know, I don't know, capitalt lowercase t trauma ensued and
uh, it's uh scary to go back tothat possibility space, you
know, and to be in that positionwhere it's like, all right, I
have to convince you that youshould put money into this
company, otherwise I don't getto keep working on this company
(18:44):
or not.
I have to convince you, but Ihave to convince somebody to put
money in this company.
So that's why I'm kind of likesteering very clear of maybe a
little too clear, of being in aposition of needing to raise to
the point where it's like Ishould be investing a little bit
more aggressively, not totalcockroach mode kind of a thing I
(19:04):
would imagine, like theprevious experience was really
painful and you're really tryingto avoid it.
Speaker 1 (19:07):
Yeah, exactly, yeah.
So what I'm, what I'm noticing,is that when we consider how
you're showing up to thesituation raising money, let's
call it the thing that's largelyinfluencing you right now is
(19:28):
the fear.
Yes, there's some sense thatfear is.
Fundamentally, I'm trying toavoid a particular outcome, and
one could argue that we're notjust avoiding an outcome, but
we're avoiding a feeling in thatoutcome.
Right, and so what's thefeeling of that situation that
(19:50):
you're trying to avoid?
Like what that?
Or I should just freeze that.
It's like what's the feelingyou're trying to avoid here?
Speaker 2 (19:55):
painting a picture of like the world that I'm kind of
like that sucked and I don'twant to go there again.
Is this sense that I, um, now Ihave to go get a job and I
don't really want to get a job.
I want to keep working on thisthing.
(20:15):
I love working on it, I believein the potential of it and I
love sort of being in control.
I think is a huge part of ittoo.
When you have a job, a lot moreis out of your control.
When you're whatever, even ifit's like a, it has to go down
to the skeleton crew and it'sjust me.
(20:36):
Okay, fine, I'm still incontrol.
Speaker 1 (20:38):
I'm happy you know so it's a loss of control that
that you're probably.
Speaker 2 (20:42):
That's the underlying thing is just this feeling of
not being in control.
I and it's a thing that I'vehated about previous jobs at
times is like it's amazing whenyou're aligned with what the
people who kind of have power inthe company usually the
founders right want, and thenwhen you're not, it's really
painful, um, and so I'd ratherjust avoid that and do the
(21:06):
things that I think make senseand hopefully they work out in
the marketplace kind of deal umyeah, rather than have to
convince someone of a thing ortry and convince myself to get
aligned with their thing.
You know, I basically that'sthat's a problem I've had in my
life generally is I'm not verygood at convincing myself to get
aligned with something thatdeep down I'm not aligned with.
Uh, if I don't think it's agreat idea, but someone else
(21:29):
wants me to do it, it's hard forme to set it aside and be like,
oh, maybe I'm wrong, I'll go doit, let's see how it goes.
Speaker 1 (21:34):
Yeah, so I the.
The key thing I hear in that isthat there's this, there's a
situation where you end uptrying to convince yourself to
get aligned right and in myexperience, you're either
aligned with something or you'renot.
Trying to convince yourself toget aligned is almost like a
contradiction in terms.
Speaker 2 (21:53):
I also find that I have weirdly specific
preferences.
Like I think maybe it's easierfor other types of people who
are like really happy havingjobs you know where someone else
is their boss.
Telling them what to do for along period of time is like they
just don't.
It's kind of fine with themeither way, like they have some
things they care about, but likethe thing that I kind of care
about is like overall, what arewe doing?
What is what are we betting on?
(22:14):
Yeah, that's what I ultimatelycare about most is like what's
our bet?
And that's like a founder levelcall right, um, if I was like
just, oh, I love writing code orI love designing really cool
interfaces, then it would bevery easy for me to be like tell
me what interface to design.
Like what's a good interface?
What's a good problem I shouldsolve?
I'll go solve it.
But I'm like I want to pick theproblem you know, um, and so
(22:36):
it's.
I find myself frequently.
I think you're right that ifyou are in a position where
you're kind of needing toconvince yourself to get aligned
, like that's just that's a hardposition to be in and maybe
it's better for everyone ifyou're like well, we're not
aligned, so maybe it doesn'tmake sense for me to be in this
role.
I feel like I'd be switchingroles a lot, you know, because I
, like, have specific thingsthat get me excited, uh, and by
default, things don't get meexcited so.
Speaker 1 (22:57):
So part of what I hear in that is this sense that
I can't get sufficient controland alignment unless I'm a
founder.
Speaker 2 (23:06):
Yeah, intellectually it's less like I can't and it's
more like it's hard and it'sless probable, it's less likely.
Whereas as a founder or youknow the other like the times in
my career when I've had a besttime being an employee is I
reported directly to a founderand I had wide leeway over a big
(23:29):
thing that I was working on andbasically in charge of, and we
had a great relationship and hewas almost more like an investor
than a boss.
He was just like do your thing,I trust you, it's working, keep
going.
You know, that's the kind ofI'd be totally happy in a
situation like that.
Probably Okay, you know, untilsomething else happens and the
board decides something or thatfounder leaves or whatever.
Speaker 1 (23:49):
Sure, but a high degree of autonomy, agency
control is really important toyou and, more specifically,
there's a certain scope ofautonomy.
That's really important.
Yep, yeah, and so what I heargoing, connecting back to the
investor conversation, is thatwhen you're in that investor
conversation, there's like a lotof stakes there for you.
(24:10):
It's like if you don't get thisright or if you don't get that
person on your side, you mightlose that ultimately.
Speaker 2 (24:17):
Totally, because not only maybe they don't make the
decision to put money in, butmaybe they do, and then they
have the ability to exert a lotof control, not necessarily any
one person or at this stage orwhatever, but like, over time
you're adding more, you'redecreasing your control.
Speaker 1 (24:34):
Basically, yeah, especially if you're on the
venture funded route.
Speaker 2 (24:37):
Yeah, so, like you know, that's the other part of
it.
that makes it scary is what, ifI have this person that I now
have no ability to fire, thatends up like not being aligned,
so it's a little like damned ifyou do, damned if you don't
almost a little, yeah, I mean,but the thing is it's damned if
I do, damned if I don't, kind of, but it's more like there are
(25:00):
risks of it working that I'mwary of and there are risks of
it not working, but I'm alsovery wary of, yeah, and I'm just
heightened sensitivity to therisks.
I don't believe that there areno upsides or that the risks
will definitely happen, so it'sit's kind of less like damned if
I do, damned if I don't, it'smore like it's just risky.
You know, of course and I haveheightened attunement to the
(25:21):
risks because of my pastexperiences- yeah, absolutely.
Speaker 1 (25:26):
And so, like, as you're mapping this out and
you're getting, you know, intouch with all this, I'm just
going to keep going back to thatquestion then.
So, when you describe thissense of like being open, warm,
connected, perhaps right, beingable to see, like, oh, this
person I could really get themon board and partner with them,
(25:50):
like yes, I hear like there's ascar tissue, there's this high
attunement to the risk there.
What would have to change inorder for you to actually have
that openness that you'redescribing?
Speaker 2 (26:05):
well, that's the thing I don't know and this is
what I always get to in variouspoints of therapy is I feel like
, like you said, I can kind ofarticulate the deal like if you
were, like I can, I can, I canrecite the sort of like
cognitive behavioral therapy,like reframe, of like more
accurately, kind ofunderstanding the situation,
like I can do a lot.
I'm very good at doing that andthen I have a meeting with an
(26:25):
investor and I sit down and westart talking in 10 minutes and
I'm just like fuck this personlet's stay with that.
Speaker 1 (26:32):
Let's stay with that for a second.
Yeah, fuck this person.
Yeah, so so when you say fuckthis person, what?
How do you feel in your bodyangry, great.
Where do you feel that anger inyour body?
Uh?
Speaker 2 (26:48):
gut, shoulders, chest .
It's like a.
It's like a visceral get thefuck away from my business kind
of a feeling, like it's like aprotective, like you like the
whole like mama bear oxytocinthing, it's like that.
Speaker 1 (27:03):
Okay, great yeah.
So it's like fight or flight.
It's protecting.
Speaker 2 (27:08):
Yeah, it's more on the fight than the flight, to be
honest.
Now, sure, and it's funny,because earlier in my career it
was way more flight and now it'smore like leave me alone so I
can build this business I don'twant you infecting it kind of a.
Speaker 1 (27:22):
Thing I want to invite you to get closer to that
feeling, though, yeah.
So rather than talking about it, I want to just be with it,
yeah, and so just as you're withthat.
You said it's protecting what.
Is it protecting what needsprotection?
Um?
Speaker 2 (27:41):
the, the, the vision, like the thing that I want to
build there's like I think theexperience I have is like
there's this precious, reallyfragile thing that's worth
pulling on and it's so easilymisunderstood, so hard to see
Like some people get it.
Speaker 1 (28:00):
I find, in general, Is that the thing that you're
protecting against the feelingof being misunderstood some
people get it.
Speaker 2 (28:08):
I find, in general, is that the thing that you're
protecting against the feelingof being misunderstood?
No, well, maybe I guess myfirst instinct is more just like
what I'm protecting against issomeone who doesn't get it and
shouldn't be a part of itbecoming inextricably a part of
it, or depending on someone toget it, who they think they get
(28:30):
it, or whatever maybe they.
I'm almost more afraid ofpeople of, like, the wrong type
of person getting excited aboutit and needing to take their
money than I am about people notgetting excited about it,
because then it's like there'sno transaction that's taken
place.
Now it's actually.
This is very useful because nowthat I'm really getting into
the feeling of it, it is afeeling of I don't care if I'm
misunderstood as long as I'm notstopped from doing the thing.
Speaker 1 (28:53):
Yeah, so there's a scenario where this person
doesn't really get it.
They're getting involved, andthen what happens?
Speaker 2 (29:06):
What is it that you're imagining happens?
Then it becomes this is such astrong and extreme word that
sounds weird, but like debasedright Right, there's something
pure and they're debasing it.
Speaker 1 (29:13):
Okay, so I just want you to pause, slow down and stay
with that.
Yeah, so something gets debased, and then the feeling that
comes up for you internally thenis what probably a little bit
of shame.
Speaker 2 (29:29):
Why did I, with this person, fuck this up?
You know, like we had somethingthat was very good, it was on
the right track, and out of fearwe like brought these other
people in.
They didn't quite get it.
They pushed for us to build itin the wrong way Not wrong, just
different.
They didn't get it.
We're not unfolding our thinganymore.
(29:49):
It's this other thing.
That's what is that?
Speaker 1 (29:51):
Yeah, it's no longer the thing that you were really
envisioning.
It's not the baby anymore.
Speaker 2 (29:56):
It's not the baby, it's just this, you know piece
of their portfolio, that they'repushing for it to become, based
on their ideas, what they thinkit should be, but they don't
actually understand they're likea money person and tell me more
about the shame that you justuh saw uh, the shame.
The shame is for kind of likethe weakness of not rejecting
(30:16):
that early.
Yeah, um, and so that's why Ithink I get so like the whole
mama bear oxytocin thing of likeget the fuck away is um like
wanting to be strong and protect.
The thing which I do think is alike again, I think it's a
venture scale thing.
(30:36):
The thing I'm excited about isa big thing also, all sorts of
it's like tale as old as time.
Entrepreneur is excited about athing.
They want to build it in acertain way.
They want to do it right.
There's like a person who seemsaligned but like ultimately kind
of isn't but has probably aoverlapping but kind of
different vision for it Ends up,through subtle and unsubtle
(31:00):
ways, influencing it towardsthat path.
Entrepreneur gets disillusioned, no longer is happy running
their own business, no longerfeels at home in their own
business.
They probably feel shame orregret about choices they've
made.
They don't feel like they'vedone right by their customers.
They don't feel like theyreally built the thing they
wanted to build.
And then they leave and they'relike maybe they even make a lot
of money out of it.
But they and they're like maybethey even make a lot of money
(31:21):
out of it, but they're like whatthe hell happened?
Speaker 1 (31:22):
So is that the thing ultimately?
Speaker 2 (31:23):
you think there's something almost spiritual about
unfolding an idea in the waythat makes sense to you,
according to your own trueprinciples, and I think that's
what people admire about, likeSteve Jobs or like even like
right now, like much obviouslysmaller example, but like linear
.
It's like, yeah, they're doingit their way, you know, and like
(31:45):
people like that becausethere's something inspirational
about it.
There's something spiritualabout building a thing that you
dream of.
Yeah, and I think that'sactually getting emotional now.
I want to build the thing I'mdreaming of.
I don't want to build the thingthat the money person dreams of
.
Speaker 1 (31:58):
Yeah, you know, I want to invite you to stay with
that.
It's just yeah, you know, yeah,stay with that, yeah, yeah,
there's a feeling here that theyjust came up.
Speaker 2 (32:09):
It's just that, um I think it's sadness that some of
the other things that I'vewanted to build, that I've
dreamt of that, have kind ofdied.
You know, yeah, not kind ofthey died, yeah, and I could
maybe resurrect them or do a newversion of them or whatever,
but um, there's a loss there.
Speaker 1 (32:28):
Yeah, yeah, it's like one of the hard things like
it's my baby kind of a thing.
Speaker 2 (32:35):
It's obviously not.
I have kids.
This is not the same, but thereis the sense of like.
Not the same, but there is thissense of like when you really
pour your heart into somethingand then it doesn't work but you
still feel like it could've.
It's sad there's a grievingprocess there and I really don't
want that to happen for this.
(32:56):
So hence, the mom bear, get thefuck away.
Speaker 1 (32:58):
Yeah yeah, I can totally see that.
Being a repeat founder,especially is, is uh tightly
fused with having to deal withthat loss.
The sadness, things not workingout, yeah for sure, but I want
(33:21):
to reflect something real quick.
Joe, Joe, John.
The other thing that I want toreflect here is that part of
that sadness that you're intouch with is only possible
because you deeply, deeply care.
Yeah for sure, like you deeplycare, I can tell, and so it's
(33:51):
probably part of what makes youreally effective, and it's also
what is going into theseinvestor meetings that it's
going to be rocket fuel, right,this level of caring, right, and
you're present to thisprotective instinct, so that you
don't have to feel that lossagain.
Speaker 2 (34:11):
I think also this is so important.
This is becoming more clear tome.
I've had a couple ofexperiences in my career where I
felt like, oh, I'm trying tolike be open to this way or
whatever, and like it would bebetter for everyone if I like
grew to be open to this thing,and in the end actually like I
should have just said fuck thatthing.
All along, like I kind of Isort of thought you were
(34:32):
supposed to have co-founders.
I thought like it's, it'simportant to have co-founders
you know, like Y Combinator saysit, so it's gotta be true.
Speaker 1 (34:47):
Oh yeah says it, so it's gotta be true.
Oh yeah, obviously yeah, it'slike make something people want
and like have two 20 somethingtechnical co-founders.
Speaker 2 (34:49):
you know what I mean.
Yeah, the unquestioned doctrine, yeah, anyway, I'm so much
happier this is the first timeI've been a solo founder and I'm
so much happier and I'm justlike I'm.
I might have a co-founder gamefor something I do in the future
, but like, default is no forsure and and like I, I kinda I
kinda feel like, um, maybethere's something similar about,
(35:09):
like I'm supposed to raise thatother round right now.
I should be open to it.
It's, you know, blah, blah,blah.
But it's like, maybe I'm notlike and it doesn't mean
actually that I'm not interestedin building a venture scale big
thing or whatever Cause like,if I tell you about the thing
I'm dreaming of, it's obviousthat if it works, even in like a
kind of well, we got part ofthe way there, way, but like
(35:32):
something about it worked, likethat it is a venture scale idea.
But, um, maybe it's that samekind of deal.
But I can just, instead oflearning the lesson the super
hard way, uh like go with myinstinct again and just be like,
focus on getting toprofitability first and then
it's truly like a if you want it, it's on our terms kind of a
(35:52):
deal and there's no, like we'rein all the position of strength,
you know, um let's test it outfor a second.
Speaker 1 (36:00):
So so let's just say that we had the magical ability
to delete any sense that youshould be raising money, and now
all I'm going to do is ask youto just sense, feel into, like,
what is that you want to do withthis business in the present
moment?
(36:20):
What comes up?
Speaker 2 (36:23):
there's kind of two things, one for sure.
The primary thing is like justgrow revenue, get profitable.
We don't need to spend a lotmore, we just need to execute.
We need time.
We've got time.
We are executing.
Growth has picked up lately.
It feels great.
Let's just keep doing whatwe're doing.
Heads down right.
That's like 80 20 is yeah, butwe're gonna cut.
We're cutting it a little closeand like probably, unless
(36:44):
things really really start topick up, I'm gonna have to dial
some stuff back.
That's gonna be a little bitpainful to dial back.
It's not like going to totalcockroach mode, but it's.
You know, it would be so niceif I could like.
The thing that would be greatis if I could just have, like,
our existing people put more inat terms that I like, because
then it's kind of like there'sno new people in the deal.
(37:05):
But, like you know, the model ifyou're a seed fund is kind of
like you have to be prettycareful about if you're gonna
like do these sort of extensionsand whatever and it's really
nice to get the validation fromfollowing investors that, like
you're not the only one whothinks this is exciting, and,
although I understand why theyhave the model that they have,
um, but um it yeah, that wouldbe the snap my fingers thing is
(37:28):
like I'm willing to take on alittle more dilution and it
would be nice to have a littlemore padding to do the things
we're currently doing in like aslightly more robust, nicer way,
because we're uh, we've gotwe've got an ambitious like
thing that we're building andwe've got a really, really small
team.
Speaker 1 (37:44):
When we tell people our team size, it's kind of like
wow let's assume that thosethings could like you knew you
could get that.
Let's assume that you couldthat 80.
Like you knew you could execute, and then you knew that you
could go make a deal happen withyour existing insiders.
How would that feel?
Speaker 2 (38:04):
Great, yeah, just great.
I would immediately be able totake two people that are
part-time and make themfull-time and just know that we
have that much more revenue toexecute Sorry, a much more
runway to execute to get toprofitability or whatever else.
But that would be great.
Now it's kind of like we can doit, but it's kind of it's kind
of pretty close.
We're scraping by with a lot ofthings.
Speaker 1 (38:25):
yeah, yeah so let's just imagine, like, step into
that movie for a moment, so likeyou're there fully, let's just
say that, firing all cylinders,you got the extra uh padding.
Let's just pretend that's truefor a moment.
And then you go back to thiswhole thing, going out to the
market, raising the next realquote-unquote round.
(38:46):
What do you notice, you feel,as you're looking toward that Am
?
Speaker 2 (38:53):
I assuming that we raise the extra money now from
the same people.
We got the extra padding, wehired the people full-time, we
accelerated in the way that wethink we'll accelerate if we put
our foot on the gas a littleharder on some of the things
that we're currently working onand then now we're like
profitable or really close toyeah, like kind of yeah.
That's great, honestly, if Ican go to investors with just
like I'm profitable and I'mgrowing fast and I'm open to
(39:19):
taking on some more dilutionbecause we've got some specific
things we want to do and itwould be great to add more
really great people around, uh,the board, but you know, only if
they're really great peoplekind of a thing.
That's amazing.
I feel in control.
I feel great, um, because thenit's like it's truly like no
skin on my back if you don'twant to invest, or if I don't
want you to invest, or if welike each other but there's we
(39:42):
can't come to terms.
That feel like that makes sense,right, um, that feels great.
Um, if I'm kind of like I'masking you to bet early, you
know, a lot of a lot of stuff islike working but like in a
nascent way, like six moments.
Data would probably really meana lot to see if the growth
continues with this stuff,versus like it was the pop and
then kind of flattened orwhatever.
Um, it's just kind of like itfeels a lot less.
(40:05):
I feel like I'm asking them tobet on something that's more
like.
Um, there's a spectrum fromlike team and dream to traction.
Yeah and I, it would be muchnicer for the next round to be
like just total traction andwe're profitable anyway.
Speaker 1 (40:20):
So yeah, what I hear from that is, if you were to get
to that the other side of thattraction story you also you
personally would be feeling muchmore confident about what
you're asking them to invest in.
Speaker 2 (40:31):
Totally Cause yeah, I mean that's.
The other thing is if let's saythey well, they put in the
money and then a lot of thestuff that we're doing like
doesn't work as well as we hope,which sometimes that happens,
you know that's like oh shit,you know and that's also when
investors tend to get moreinvolved.
Yeah, exactly, exactly, exactly,um.
(40:53):
So anyway, um, yeah, to me thatthat's why I'm kind of like it
makes sense to just keepfocusing and that's our.
To be clear, that's like ourplan.
Like I'm not like gearing up tofundraise, you know, before the
end of the year or somethinglike that, like we're speaking
at the end of October, if it wassort of like I got a whole
bunch of convos lined up forNovember.
We want to close the round inlike December, january or
(41:15):
whatever.
On growth, but yeah, I know thatI think the calm in general,
even the conversation with ourexisting investors about what
the next round would look like,it already brought up all this
stuff, which is why I wanted totalk about it.
But it is kind of interesting.
I do think I'm feeling morelike conviction around, like
yeah, let's like let's justreally keep focusing on growing
(41:38):
revenue.
It's working, let's just keepmaking it work.
It's really hard to make itwork.
It takes a lot of focus.
I'm going to worry about thatand also manage the business in
such a way that assuming wedon't get any more money,
assuming no more investment, soaggressive but it can't die,
(42:00):
kind of a thing.
Speaker 1 (42:01):
Right.
Speaker 2 (42:01):
So yeah, yeah.
Speaker 1 (42:06):
Well, john, as we start to wrap, I want to check
in with you and ask you know wetouched quite a few different
things here today what are youtaking away from the
conversation?
What are you taking away from?
Speaker 2 (42:20):
the conversation.
The most important thing islike actually to listen to the
mama bear thing that's like getaway from my business and to
just keep unfolding, the thingthat only our team can really
see Right.
And it's a really sensitive anddelicate thing to ask someone
(42:45):
before it really is obvious tobuy in, and inevitably they have
to do so somewhat blindly.
Miracle, when that does workwith someone that wouldn't like
a seed or pre-seed investor likeactually ends up.
I think it's probably best forpre-seed and seed investors to
be just basically supportive andyou're kind of betting on
(43:08):
founders and that's the way thatthe best ones do it.
You know they're not trying tolike manage it too much um and
um.
I mean I could probably be, Icould probably be a little bit
more open to like well, thereare some people who might do the
next round that's kind of likea seed extension or series seed
(43:30):
or whatever that do share thatphilosophy and they provide
really great ideas, but theydon't threaten any real like
we're going to make you do itour way, kind of a we're gonna
try, you know, uh, kind of athing.
Um, and so I probably should bemore open to the existence of
those people.
But it's probably actuallyright for me 10 minutes in a
meeting when someone doesn't getit and they seem like not
(43:53):
really aligned, to just be.
I could be nice about it.
But it doesn't have to ruin.
It, doesn't have to make mefeel nervous at all because I
think I've got a little bit ofresidual, like I'm depending on
them, but I'm really notsignificantly anymore.
Like I think we're already atthe point revenue-wise where,
like if I had to take it down toskeleton crew, I would be able
(44:17):
to and keep it going andfinancially, like I'm in a much
better place now and there'sjust a lot of stuff that's
different about now versus yeahit's easy to forget.
Speaker 1 (44:25):
That's an option.
Speaker 2 (44:26):
The last thing but you know, it's like been, yeah,
it's been, that's been more.
It's been like eight yearssince that scenario.
So it's like, yeah, so much haschanged.
But emotionally it's like, well, it's the last time I did that
was.
So I guess it's like theemotions are kind of cached
somewhere in my life.
You're in this situation,here's what to feel, kind of
thing.
Yeah, yeah.
Speaker 1 (44:47):
And if we had more time together, I would also just
invite you to spend more timewith those feelings, so that
they wouldn't have to be socached.
Speaker 2 (44:53):
Yeah, that is very true too.
What do you think is the like?
Because the thing that Inoticed that was really
interesting is you're asking meto like stay with, like, get the
fuck away from my business.
Feeling what?
Um, it seems like there's athing that's like oh, we tend to
resist wanting to go thereemotionally, like if it starts
(45:15):
to come up, it's like, ooh, putthat away, that's dangerous,
because then it'll make me superrude during these investor
meetings and pre-reject peopleand all this stuff.
And you're kind of like, ooh,put that away, that's dangerous,
because then it will make mesuper rude during these investor
meetings and pre-reject peopleand all this stuff.
And you're kind of like no,stay with it.
I'm curious what the deal is.
Speaker 1 (45:27):
How does that work?
So, generally, when we'rerepressing an emotion because
that's in some sense that makessense for us to do that, it's
protective, it's reallyuncomfortable, yeah, you know,
we might convince ourselves thatthe emotion is like too
(45:48):
dangerous to have, it's gonna oh, it's gonna ruin my meeting.
Well, emotions are meant to befelt.
Yeah, um, they're theexperiences that are are
demanding to be felt one way orthe other, and so when we are in
, let's call them like much moreactivating scenarios, um, then
that's where we're going to belikely.
It's more likely we're going toget triggered and reactive,
versus the alternative, which is, oh, if we can actually
intentionally, consciously,allow ourselves to feel whatever
(46:10):
it is that we've beensuppressing, whether that's
anger, fear, sadness, joy I mean, there's a whole number of
these things then, in essence,what we allow ourselves to do is
build our capacity to be withthose feelings.
Right, they're not so scaryanymore for us, right?
And then, as a result, whenthey do pop up again, they're
(46:32):
not going to overwhelm us somuch.
Yeah, interesting, interesting.
Speaker 2 (46:36):
So the thing that's very new for me here is um, I
probably I didn't realize cominginto this conversation that I
kind of thought, oh, I've gotthis mama bear instinct, which
is bad.
I need your help with itbecause it's going to ruin my
chances of raising money frominvestors because I like
pre-reject them, yeah, andactually it's kind of like no,
the mama bear instinct's prettygood, and like if you have
(46:56):
someone that you're just reallynot vibing with, just go with
with it and like whatever.
Maybe there's a differentversion of you that would vibe
with them for whatever otherreason, but like whatever, it's
fine.
Like do the thing of focusingon just making a really great
business, that you're in controlof your own destiny when you
(47:16):
feel comfortable doing that,cause you're sort of embracing
that all of a sudden.
Maybe I'm a little bit more open.
Maybe when I'm talking toinvestors, it's, it's I'm I'm
less worried about am I going topre-reject them or are they
going to reject me or whatever.
I'm just focused on my businessand good things could happen.
Um, but it's kind of funnycause it's sort of like um, the
the solution is almost likethere's a thing I'm worried
(47:40):
about.
But if I actually just kind oflean into that, then it's less
likely to happen.
Speaker 1 (47:46):
More often than not it's the resistance that
actually is the obstacle and, toparaphrase it, it's what we
resist persists.
And so what I would encourageyou to do, john, is,
specifically with that mama bearimpulse, is to get more
familiar with it, move closertoward it Really, see if you can
(48:07):
inquire into its contours.
When does it come up, whattends to activate it, what are
the things about it that you canappreciate, and also where the
places where perhaps it's notserving your interests?
(48:27):
There's a whole field ofexploration that's possible
there.
Speaker 2 (48:28):
So that's that's what I encourage you to to consider
makes sense.
Love, that, I think that's.
I think that's going to help,because it's definitely not just
investors that trigger that,it's just anything that feels
like a threat to the vision.
You know, yeah, yeah, whichevolves.
You know that's right, which iskind of funny, because one
thing that seemed like a hugethreat to the vision a year ago,
now we're doing and I'm excitedabout it, yeah, so it changes.
Speaker 1 (48:54):
Yeah, yeah, absolutely Awesome.
Well, john, thank you so muchfor spending the time today.
Thank you Really appreciate it.
Today's conversation opened upsomething fascinating about how
we relate to our protectiveinstincts as founders.
When we began, john viewedtheir visceral get away from my
business response as a liability, an emotional reaction that
needed fixing.
Yet as we dug deeper, adifferent picture emerged that
(49:17):
protective instinct wasn't justemotional baggage from past
experiences.
It was actually pointing towarda deeper truth about their
vision for the company.
The venture capital pathpresents founders with a
profound paradox.
The very investment that couldaccelerate a company's growth
often comes with the risk oflosing control over its
direction.
Stories abound of founderswhose companies grew beyond
their original vision, shaped bythe pressures and expectations
(49:39):
of their investors.
Some founders look back andbarely recognize the company
they started.
Yet what our guests discoveredwas that their protective
response, this instinct tomaintain control, wasn't
necessarily at odds withbuilding a venture-scale
business.
Rather than fighting against it, they realized they could use
it as guidance to build acompany on their own terms,
first engaging with investorsfrom a position of strength
(50:02):
rather than necessity For thefounders.
Listening, think about your ownprotective responses, those
instincts that feel almostprimal in their intensity
Instead of seeing them asproblems to solve what might
happen.
If you got curious about whatthey're trying to tell you about
the company that you want tobuild, thanks for tuning in
today.
If you found value in thisepisode, I'd love for you to
share it with another founder inyour life and, if you have a
(50:22):
moment, leaving a rating orreview, helps other founders
discover these conversations.
Until next time, this has beenSlow Down to Speed Up.
Welcome to Slow Down and 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's episode is specialwe're featuring our first
anonymous guest, who we'll callJohn.
In our session, john brings upone of the most profound
tensions in entrepreneurship therelationship between control
and growth.
When you take venture capital,you're making a devil's bargain,
(00:23):
trading away pieces of yourcompany's destiny for the fuel
to grow faster.
John has been in startups over adecade, building multiple
companies.
Now with a thriving businessthat may not need investment,
he's wrestling with this verydilemma.
But every time they sit downwith investors, something
visceral takes over.
He has this internal reactionthat says get away from my
business.
And John is afraid thisreaction is holding him back.
(00:44):
That's why he's here toconfront the emotional scar
tissue from past rejections andthe pressure to keep control
over his vision.
Together we explore the pushand pull of staying independent
versus raising money, his deeproot of fears of compromise and
that fierce protective instinctmany founders feel toward their
vision.
Through our session, john beginsto uncover what it means to
approach these investorinteractions from a place of
(01:04):
strength, not fear.
This is a powerful session onreconnecting with the core
vision, navigating vulnerabilityand redefining what it means to
stay open while protecting whatmatters most.
I hope you enjoy it.
Hey, john, it's great to bewith you today.
Thanks for having me.
Yeah, so we spoke a little bitabout what you want to get into
today, but why don't you spend alittle bit of time sharing what
(01:29):
you're bringing in and what youwant to explore as we sit down
together?
Speaker 2 (01:31):
in tech, starting companies or having jobs at
different kind of startups phasecompanies for my whole career,
which is over 10 years, and I'velearned a lot in that time.
For sure, at the beginning ofmy career, I was very ambitious.
(01:54):
I was like kind of one of thoseright out of college
entrepreneurs and I got a lot ofrejection from investors and I
think now I'm in a much betterposition.
My company has, I've got a lotmore experience in my career,
I'm feeling a lot more confidentand even the company that I
have founded and I'm working onnow is in a good spot where we
(02:15):
may not even really needinvestment but it feels like it
would help us grow and it'sdefinitely like we're down the
venture path and I'm happy withthat path and I really liked
that path, um.
So I'm thinking about what thenext round might look like and,
as I've started talking to someinvestors, a little bit like
kind of building earlyrelationships and, um talking to
our current investors, a lot ofstuff is coming up that I'm
(02:37):
realizing would be helpful forme to explore around kind of um
scar tissue I think that Iformed, especially early in my
career and some more recentaround rejection Not only from
investors, but kind of likespecifically from investors is
probably the best place to focusit, and just the feeling of
like being kind of misunderstoodor underestimated or it's so
(03:02):
frustrating that people don'tsee what you see and people
don't get it.
And I think part of what happensI've realized is I found that I
feel a little tense sometimesin those conversations.
I feel like it's actuallyreally hard for me to develop a
lot of warm feelings or evenlike respect sometimes when I'm
(03:22):
talking to investors feelings oreven like respect.
Sometimes when I'm talking toinvestors, I kind of look, I
don't look down on them, but Ijust find it hard to um, I think
I went through a phase earlierin my career where I probably
put them too much on a pedestaland now I'm probably doing too
much the opposite.
It's like investors reallydon't know anything at all and
they're here for, like my kindof a thing yeah.
Speaker 1 (03:39):
Yeah, no offense to any investors listening to this
right now.
Speaker 2 (03:48):
Yeah and and um, you know, they know some things.
There's some investors that arereally great to work with.
Of course, like intellectuallyI know that, but emotionally in
the moment, when I'm talking toan investor and I'm realizing,
like in the moment, I'm kind oflike losing respect for them.
They're not really following,they're not keeping up, uh, it's
, it's I, I sort of pre-rejectthem before they have a chance
to reject me, which is a commonuh, I think, uh, emotional
survival strategy that happenswhen people have been through
rejection is, it's, like youknow, once bitten, twice shy, or
whatever.
(04:08):
Like you know, I'll reject youbefore you can reject me, kind
of a thing.
And I feel like it wouldprobably be useful for me to
talk through a lot of this stuffso that I can go through
whatever fundraise process mayhappen at some point in the
nearish future more balanced,more more grounded, more open to
people, just being awesomebecause there are a lot of
(04:29):
awesome investors out there andalso like, yeah, there are
certainly not great investors,but not to, like you know, have
it really affect me so much ifsomeone, uh, just you know,
isn't picking up what I'mputting down in conversation,
it's not necessarily anindictment of me or them.
It's just not fit, probably,and it's totally fine um so, uh,
probably.
(04:49):
The one last thing I'll put onthis is um, and I think, overall
, this is a healthy thing, butit's interesting to think
through is um.
I think one layer deeper islike how this feeling of like a
fundraise is going to be hardemotionally affects my overall
strategy.
Because I think there is um aworld, you know, in 2021 and
(05:13):
around then, when people werejust raising enormous sums
really easily seemingly, and, um, kind of messing up for
companies in the process, yeah,with enormous valuations, and I
definitely don't want to do that.
But I think there's also it ispossible, especially if you are
like committed to the venturepath, to go too far, to the
other extreme, where you're justyou're in survival mode, you're
in cockroach mode and thecompany it's kind of like too
(05:35):
hungry to eat, kind of a thingwhere you don't have enough
resources to actually like doyour plan yeah there's like this
pure scarcity thing going onyour plan.
Yeah, there's like this purescarcity thing going on, exactly
, and so I think there's part ofit is about just I want to go
into a fundraise process, um youknow, with good chances of
building great relationships andresonating with good people and
(05:55):
all that kind of stuff andgetting the capital.
I need or want to acceleratethe business.
But also there's kind of thisfeeling of like, what if I
didn't think a fundraiser wassuch a?
you know, alternating betweenannoying and frustrating or
scary thing, and I thought of itmore as something that could be
, uh, a useful, like more of anoption.
(06:15):
It's like it's a.
It's a not an easy optionnecessarily, but like, uh, it's.
Speaker 1 (06:19):
it's not like a dark corner of the entrepreneurship
journey, it's more of like, yeah, that's a thing that's totally
there and doesn't have to wedon't have to shape our whole
strategy around avoiding needingto do it or something.
Yeah, I mean wow, so.
So there's a lot to unpack inwhat you just shared.
Um and so like, in noparticular order.
I just want to reflect a littlebit before we dive in.
(06:42):
I know I know a lot of founderswho can relate to exactly what
you're describing, john, thiswhole sense of like wow, like
fundraising as a function of thefounder seat.
The CEO seat is dark and scaryand painful and terrible, and
it's interesting because Iactually know quite a few
founders who enjoy it.
They take delight in it andit's fascinating.
Speaker 2 (07:03):
It's like the total opposite.
For some people they're likereally good at fundraising, and
sometimes there's people who areamazing at fundraising and like
not so good at the other partsof running a company.
That's right, that's right.
Yeah, the opposite problem theyshould be more great at both.
Speaker 1 (07:14):
Yeah, that's right.
And I bring that up becausewhat occurs to me is that it's
possible to inhabit and embodydifferent orientations and
perspectives on that whole thing, right.
And when I go back to what youwere sharing, john, this whole
sense of I mean the first, thefirst thing that strikes me as,
(07:35):
as I'm listening to you, is thatyou're really well aware of
yourself in terms of the mental,emotional patterns that you
have.
You mentioned scar tissue.
You're even very articulate indescribing yeah, there's some
self-defense going on there,defensive reactions there, yeah,
right.
(07:55):
And so my intuition tells methat what we'll look at is
probably going to go a littlebit underneath that surface,
like below, just like theintellectual, cognitive knowing
of it.
But maybe, just to set thestage here for a moment, if we
can just articulate it, like ifyou were to go and just define
(08:18):
in words the attitude that youwant to bring into a fundraise,
how would you describe it?
Speaker 2 (08:28):
Great question.
Um, I would say openness tofeedback, while at the same time
not it doesn't necessarilychange our plans, but it's there
could be interesting stuffthat's worth looking into deeper
or doing something with.
Know.
Um, I would say openness tosome investors being really
(08:51):
great and have being like areally positive force for the
trajectory of the company yeah,um, and at the same time,
handling people who clearlyaren't, because I'm going to
encounter them with a bit oflike, it doesn't ruin my day and
it's not so annoying that Ihave to deal with these people
and whatever it's just like yeahthere's going to be some people
who aren't in a good positionto be a positive force for our
(09:13):
company, and the cost of findingthe ones who are is to talk to
some of the ones who aren't.
It's like interviewing employees.
You know, it's not nearly asstressful to interview 20
candidates for a role and have15 of them not really be in the
running in a serious way.
Uh, for whatever reason, talkingto 20 investors and having 15
(09:33):
of them like not get it.
I think it's because implicitlyit's it doesn't feel like I'm
in power.
Uh, tell me more about that.
Well, if I have a budget tohire someone and it's my choice
who to hire like finding peoplewho aren't qualified but, you
know, having a phone screen withthem or whatever, where I kind
(09:53):
of quickly figure out they'reprobably not right for the role,
I just feel totally comfortable.
I feel in the driver's seat.
Maybe there's something to learnabout like our screening
process or whatever else, butlike it's not a huge deal at all
, Right yeah about like ourscreening process or whatever
else, but like it's not a hugedeal at all, right yeah.
But, um, if it feels like, wow,you know, maybe we don't need
this money, but this money wouldbe really useful, um and uh,
(10:16):
but it's, you know, it's their,it's their money, it's their,
their sort of hiring forfounders, in a way, right, it's
kind of like the mental modelthey have the budget but they're
deciding where to spend it interms of capital and in terms of
time that they spend withcompanies, and it feels like I
don't expect.
(10:36):
I mean, it's possible.
I haven't really, in anyserious way, gone to market with
this idea yet.
Sometimes, when you do, youfind yourself in a competitive
bid, and it's kind of you.
Do you know?
Like you find yourself in acompetitive bid, it's kind of
you and you're more like theperson with the budget making
the hire.
Speaker 1 (10:48):
Usually the case is, though, you're kind of you're
more making the sale, at leastfor the first part, right okay,
so there's a sense that whenyou're in that pitch or in that
conversation, they have more ofthe power.
Uh, it's just a the kind oflike gross generalization, but
that's how it feels.
Speaker 2 (11:04):
Exactly that's how it feels but it's funny because
it's kind of like, as soon as Isay that I'm like, why am I
giving them that?
Why are you giving them?
Speaker 1 (11:13):
that.
Let's just, let's take thatseriously.
Why are you giving them that um?
Speaker 2 (11:22):
I think, um, I think it's really funny because what's
coming to mind is that myinstinct is to.
I desperately don't want togive them that, and I feel like
the only way to not give themthat is to just build a company
that's growing incrediblyquickly and is profitable, so
(11:42):
that we don't need to raisemoney.
But we might choose to, but wedon't need to, and so every
fiber of my being wants to focuson that.
Yeah, and I probably would growa little bit slower and the
company might not be off to anamazing trajectory if I did that
versus was willing or able orwhatever to raise a little bit
(12:05):
more, ahead of some of thoselike oh, yeah, we're already
profitable and we don't need youat all, but just to be able to
go into those conversations like, yeah, like we're growing
really fast, we've proven a lotof stuff, but like we're not
profitable because we chose tospend more, because we chose to
invest in growing faster,because we thought we'd have a
great chance of raising moneyand we could always dial it back
.
It's not existential kind of athing, but if you operate in a
(12:29):
little bit more of a fear-basedway, then you don't make the
investments because you'reavoiding being in a position
where you sort of quote needmoney and there's varying
degrees of need, but pushing itmore into the yellow zone.
We never want to get to the redzone.
The green zone is like you know, we raised two and a half
million and we have two millionin the bank still two years
later, or whatever.
Sure, but like, basically, ifyou push it a little bit more to
(12:50):
the yellow zone, we're likebecause we've got lots of ideas
we could probably hire a littlebit more aggressively or spend a
little bit more aggressively topursue some of those ideas, or
pursue the same set of ideas ina sort of more comprehensive way
or bigger way, the same set ofideas in a sort of more
comprehensive way or bigger way.
Um, yeah, it's.
(13:10):
I do think a pattern that I'veseen is a lot of founders push
it a little bit more into theyellow zone, not risking death
of the company, but anyway, it'sinteresting.
You can kind of see the, the,the, the loop that goes between.
It's the way I operate thecompany, based on the way I want
to relate to investors, where Iwant to have the power in those
conversations, based on the wayI want to relate to investors
or I want to have the power inthose conversations.
Speaker 1 (13:24):
So I think what you're describing is a very real
dynamic.
What I will assert is that itdoesn't have to be that way, and
maybe what I would say on topof that is it doesn't have to be
so, dictated by the externalcircumstances is the premise
I'll start with.
I know founders who they go outfundraising and they have five
(13:48):
months of runway to like theiryellow-red zone.
Speaker 2 (13:52):
I'll call five months red, yeah, yeah.
Yeah, I'll call very red.
Yeah, it depends on your riskprofile.
Speaker 1 (13:58):
But they also can go out with this openness that
you're describing.
Yeah, and without this sense ofthis person really has power
over me, yeah, right, and so I'mcurious for you if we take a
look, what is it that you'rebelieving about yourself in that
(14:18):
interaction?
That's saying this personreally has power over me.
I don't have the power, sayingthis person really has power
over me.
Speaker 2 (14:28):
I don't have the power.
The extent to which I feel liketheir choice dictates whether I
get to keep working on thiscompany or not, probably, and so
that's why I'm like I justreally love doing it.
I really want to keep workingon this for a long time.
I've had a lot of things in mycareer that I've loved working
on, but for one reason oranother I wasn't able to see it
through to the extent that Ireally wanted to.
Speaker 1 (14:50):
Let me pause for a second though.
Yeah, so I just want to zoom inon that.
You said there's this sensethat it's up to this person on
whether or not I get to continueworking on this.
Speaker 2 (15:01):
Well, not this person , but I need someone to say yes
kind of a thing, not any oneperson, but I need.
I need someone to say yes kindof a thing, not any one
particular person, but you needsomeone to say yes to keep going
.
That sense that it's not justabout anymore my choices, about,
like, my ability to build aproduct that generates enough
revenue to sustain the team andthe infrastructure necessary to
keep running the thing.
Yeah, it's about outsideinvestment needs to come in for
(15:23):
this thing to continue there's areal dependency.
Speaker 1 (15:25):
Yeah, yeah, it's a very, it's a very real, like
brass tacks, yes, like we'redependent on external capital,
uh, like in this scenario thatwe're constructing in order for
us to continue.
Yeah, exactly.
And so in that world where,like, let's say like, yeah,
objectively, there is thisdependency, let's just call it
that I would imagine thatthere's like a certain sense of
vulnerability that comes withthat totally totally and what's
(15:48):
that like for?
Speaker 2 (15:49):
you, um, a heightened one for me because, uh, my last
company or a previous company,not my very last company, but in
in my past I've had a companythat I love working on and I
really believed in, and you know, we raised a pre-seed but we
couldn't raise a seed and so wejust ran out of cash and it was
(16:11):
like my bank account was empty,the company bank account was
empty.
There was nothing I could doexcept for try and sell it for
scraps and like go get a job,basically, yeah, and lay
everybody off and shut down theservice and all that kind of
stuff.
And it just was heart-wrenchingbecause I love that thing and I
wanted to keep working on it,but I just didn't.
Money, you know, like I had tobe able to pay rent and I had to
(16:32):
.
You know, I couldn't find anyother way.
I was sort of the other thingis by the end of it because I
focused the last you know monthsof the company's life on
fundraising.
Of course, you know, knowthat's kind of uh, it's too late
and I was like out of energyand like it's, it's always
possible, like now I feel likeI'm in a much better spot where
I'm like, okay, I'm never gonnalet it get to that point again,
(16:54):
sure, but even then it's kind ofand it's it's good that I'm
technical so I can kind of likejust keep the thing running
myself and take it down to likeskeleton crew for a little while
, sure, um, so I don't reallyfeel like that this has a chance
of that happening again.
But that was a deep scar tissueof just like it was so sad to
not be able to work on thatthing anymore and to have to go
get the job you know yeah, Itotally get that.
Speaker 1 (17:16):
I totally get that.
I've been through that.
I know many people have beenthrough that.
And if we go back to how westarted this, you talked about a
desire to go into theseconversations with openness,
with the.
You know, there's like anopenness to really connecting to
the person in front of you.
Um, not letting the feedback,whether whatever it is like,
(17:39):
sway you too much.
Speaker 2 (17:40):
Yeah, take me evenly the same way I would take
feedback from like a friend butthat's the feeling is, if a
friend tells me some stuff thatI don't think is great advice,
I'll either like if, dependingon the type of friend, be candid
with them, like I don't knowabout this for this reasons, or
just, oh, that's a good idea,but either way it doesn't really
affect my mood too much and I'mable to be pretty open and
process the information that isin front of me in like an even
(18:01):
way or like same thing.
Speaker 1 (18:02):
If an employee or you know, uh, yeah investor it's
different so how much of thatemotional scar tissue that
you're referring to earlier iscoloring the present around
taking these things, you knowpersonally um, I mean, yeah, I
feel like that's the whole thingright.
Speaker 2 (18:21):
It's basically like I've been in this situation
before.
You know, I don't know, capitalt lowercase t trauma ensued and
uh, it's uh scary to go back tothat possibility space, you
know, and to be in that positionwhere it's like, all right, I
have to convince you that youshould put money into this
company, otherwise I don't getto keep working on this company
(18:44):
or not.
I have to convince you, but Ihave to convince somebody to put
money in this company.
So that's why I'm kind of likesteering very clear of maybe a
little too clear, of being in aposition of needing to raise to
the point where it's like Ishould be investing a little bit
more aggressively, not totalcockroach mode kind of a thing I
(19:04):
would imagine, like theprevious experience was really
painful and you're really tryingto avoid it.
Speaker 1 (19:07):
Yeah, exactly, yeah.
So what I'm, what I'm noticing,is that when we consider how
you're showing up to thesituation raising money, let's
call it the thing that's largelyinfluencing you right now is
(19:28):
the fear.
Yes, there's some sense thatfear is.
Fundamentally, I'm trying toavoid a particular outcome, and
one could argue that we're notjust avoiding an outcome, but
we're avoiding a feeling in thatoutcome.
Right, and so what's thefeeling of that situation that
(19:50):
you're trying to avoid?
Like what that?
Or I should just freeze that.
It's like what's the feelingyou're trying to avoid here?
Speaker 2 (19:55):
painting a picture of like the world that I'm kind of
like that sucked and I don'twant to go there again.
Is this sense that I, um, now Ihave to go get a job and I
don't really want to get a job.
I want to keep working on thisthing.
(20:15):
I love working on it, I believein the potential of it and I
love sort of being in control.
I think is a huge part of ittoo.
When you have a job, a lot moreis out of your control.
When you're whatever, even ifit's like a, it has to go down
to the skeleton crew and it'sjust me.
(20:36):
Okay, fine, I'm still incontrol.
Speaker 1 (20:38):
I'm happy you know so it's a loss of control that
that you're probably.
Speaker 2 (20:42):
That's the underlying thing is just this feeling of
not being in control.
I and it's a thing that I'vehated about previous jobs at
times is like it's amazing whenyou're aligned with what the
people who kind of have power inthe company usually the
founders right want, and thenwhen you're not, it's really
painful, um, and so I'd ratherjust avoid that and do the
(21:06):
things that I think make senseand hopefully they work out in
the marketplace kind of deal umyeah, rather than have to
convince someone of a thing ortry and convince myself to get
aligned with their thing.
You know, I basically that'sthat's a problem I've had in my
life generally is I'm not verygood at convincing myself to get
aligned with something thatdeep down I'm not aligned with.
Uh, if I don't think it's agreat idea, but someone else
(21:29):
wants me to do it, it's hard forme to set it aside and be like,
oh, maybe I'm wrong, I'll go doit, let's see how it goes.
Speaker 1 (21:34):
Yeah, so I the.
The key thing I hear in that isthat there's this, there's a
situation where you end uptrying to convince yourself to
get aligned right and in myexperience, you're either
aligned with something or you'renot.
Trying to convince yourself toget aligned is almost like a
contradiction in terms.
Speaker 2 (21:53):
I also find that I have weirdly specific
preferences.
Like I think maybe it's easierfor other types of people who
are like really happy havingjobs you know where someone else
is their boss.
Telling them what to do for along period of time is like they
just don't.
It's kind of fine with themeither way, like they have some
things they care about, but likethe thing that I kind of care
about is like overall, what arewe doing?
What is what are we betting on?
(22:14):
Yeah, that's what I ultimatelycare about most is like what's
our bet?
And that's like a founder levelcall right, um, if I was like
just, oh, I love writing code orI love designing really cool
interfaces, then it would bevery easy for me to be like tell
me what interface to design.
Like what's a good interface?
What's a good problem I shouldsolve?
I'll go solve it.
But I'm like I want to pick theproblem you know, um, and so
(22:36):
it's.
I find myself frequently.
I think you're right that ifyou are in a position where
you're kind of needing toconvince yourself to get aligned
, like that's just that's a hardposition to be in and maybe
it's better for everyone ifyou're like well, we're not
aligned, so maybe it doesn'tmake sense for me to be in this
role.
I feel like I'd be switchingroles a lot, you know, because I
, like, have specific thingsthat get me excited, uh, and by
default, things don't get meexcited so.
Speaker 1 (22:57):
So part of what I hear in that is this sense that
I can't get sufficient controland alignment unless I'm a
founder.
Speaker 2 (23:06):
Yeah, intellectually it's less like I can't and it's
more like it's hard and it'sless probable, it's less likely.
Whereas as a founder or youknow the other like the times in
my career when I've had a besttime being an employee is I
reported directly to a founderand I had wide leeway over a big
(23:29):
thing that I was working on andbasically in charge of, and we
had a great relationship and hewas almost more like an investor
than a boss.
He was just like do your thing,I trust you, it's working, keep
going.
You know, that's the kind ofI'd be totally happy in a
situation like that.
Probably Okay, you know, untilsomething else happens and the
board decides something or thatfounder leaves or whatever.
Speaker 1 (23:49):
Sure, but a high degree of autonomy, agency
control is really important toyou and, more specifically,
there's a certain scope ofautonomy.
That's really important.
Yep, yeah, and so what I heargoing, connecting back to the
investor conversation, is thatwhen you're in that investor
conversation, there's like a lotof stakes there for you.
(24:10):
It's like if you don't get thisright or if you don't get that
person on your side, you mightlose that ultimately.
Speaker 2 (24:17):
Totally, because not only maybe they don't make the
decision to put money in, butmaybe they do, and then they
have the ability to exert a lotof control, not necessarily any
one person or at this stage orwhatever, but like, over time
you're adding more, you'redecreasing your control.
Speaker 1 (24:34):
Basically, yeah, especially if you're on the
venture funded route.
Speaker 2 (24:37):
Yeah, so, like you know, that's the other part of
it.
that makes it scary is what, ifI have this person that I now
have no ability to fire, thatends up like not being aligned,
so it's a little like damned ifyou do, damned if you don't
almost a little, yeah, I mean,but the thing is it's damned if
I do, damned if I don't, kind of, but it's more like there are
(25:00):
risks of it working that I'mwary of and there are risks of
it not working, but I'm alsovery wary of, yeah, and I'm just
heightened sensitivity to therisks.
I don't believe that there areno upsides or that the risks
will definitely happen, so it'sit's kind of less like damned if
I do, damned if I don't, it'smore like it's just risky.
You know, of course and I haveheightened attunement to the
(25:21):
risks because of my pastexperiences- yeah, absolutely.
Speaker 1 (25:26):
And so, like, as you're mapping this out and
you're getting, you know, intouch with all this, I'm just
going to keep going back to thatquestion then.
So, when you describe thissense of like being open, warm,
connected, perhaps right, beingable to see, like, oh, this
person I could really get themon board and partner with them,
(25:50):
like yes, I hear like there's ascar tissue, there's this high
attunement to the risk there.
What would have to change inorder for you to actually have
that openness that you'redescribing?
Speaker 2 (26:05):
well, that's the thing I don't know and this is
what I always get to in variouspoints of therapy is I feel like
, like you said, I can kind ofarticulate the deal like if you
were, like I can, I can, I canrecite the sort of like
cognitive behavioral therapy,like reframe, of like more
accurately, kind ofunderstanding the situation,
like I can do a lot.
I'm very good at doing that andthen I have a meeting with an
(26:25):
investor and I sit down and westart talking in 10 minutes and
I'm just like fuck this personlet's stay with that.
Speaker 1 (26:32):
Let's stay with that for a second.
Yeah, fuck this person.
Yeah, so so when you say fuckthis person, what?
How do you feel in your bodyangry, great.
Where do you feel that anger inyour body?
Uh?
Speaker 2 (26:48):
gut, shoulders, chest .
It's like a.
It's like a visceral get thefuck away from my business kind
of a feeling, like it's like aprotective, like you like the
whole like mama bear oxytocinthing, it's like that.
Speaker 1 (27:03):
Okay, great yeah.
So it's like fight or flight.
It's protecting.
Speaker 2 (27:08):
Yeah, it's more on the fight than the flight, to be
honest.
Now, sure, and it's funny,because earlier in my career it
was way more flight and now it'smore like leave me alone so I
can build this business I don'twant you infecting it kind of a.
Speaker 1 (27:22):
Thing I want to invite you to get closer to that
feeling, though, yeah.
So rather than talking about it, I want to just be with it,
yeah, and so just as you're withthat.
You said it's protecting what.
Is it protecting what needsprotection?
Um?
Speaker 2 (27:41):
the, the, the vision, like the thing that I want to
build there's like I think theexperience I have is like
there's this precious, reallyfragile thing that's worth
pulling on and it's so easilymisunderstood, so hard to see
Like some people get it.
Speaker 1 (28:00):
I find, in general, Is that the thing that you're
protecting against the feelingof being misunderstood some
people get it.
Speaker 2 (28:08):
I find, in general, is that the thing that you're
protecting against the feelingof being misunderstood?
No, well, maybe I guess myfirst instinct is more just like
what I'm protecting against issomeone who doesn't get it and
shouldn't be a part of itbecoming inextricably a part of
it, or depending on someone toget it, who they think they get
(28:30):
it, or whatever maybe they.
I'm almost more afraid ofpeople of, like, the wrong type
of person getting excited aboutit and needing to take their
money than I am about people notgetting excited about it,
because then it's like there'sno transaction that's taken
place.
Now it's actually.
This is very useful because nowthat I'm really getting into
the feeling of it, it is afeeling of I don't care if I'm
misunderstood as long as I'm notstopped from doing the thing.
Speaker 1 (28:53):
Yeah, so there's a scenario where this person
doesn't really get it.
They're getting involved, andthen what happens?
Speaker 2 (29:06):
What is it that you're imagining happens?
Then it becomes this is such astrong and extreme word that
sounds weird, but like debasedright Right, there's something
pure and they're debasing it.
Speaker 1 (29:13):
Okay, so I just want you to pause, slow down and stay
with that.
Yeah, so something gets debased, and then the feeling that
comes up for you internally thenis what probably a little bit
of shame.
Speaker 2 (29:29):
Why did I, with this person, fuck this up?
You know, like we had somethingthat was very good, it was on
the right track, and out of fearwe like brought these other
people in.
They didn't quite get it.
They pushed for us to build itin the wrong way Not wrong, just
different.
They didn't get it.
We're not unfolding our thinganymore.
(29:49):
It's this other thing.
That's what is that?
Speaker 1 (29:51):
Yeah, it's no longer the thing that you were really
envisioning.
It's not the baby anymore.
Speaker 2 (29:56):
It's not the baby, it's just this, you know piece
of their portfolio, that they'repushing for it to become, based
on their ideas, what they thinkit should be, but they don't
actually understand they're likea money person and tell me more
about the shame that you justuh saw uh, the shame.
The shame is for kind of likethe weakness of not rejecting
(30:16):
that early.
Yeah, um, and so that's why Ithink I get so like the whole
mama bear oxytocin thing of likeget the fuck away is um like
wanting to be strong and protect.
The thing which I do think is alike again, I think it's a
venture scale thing.
(30:36):
The thing I'm excited about isa big thing also, all sorts of
it's like tale as old as time.
Entrepreneur is excited about athing.
They want to build it in acertain way.
They want to do it right.
There's like a person who seemsaligned but like ultimately kind
of isn't but has probably aoverlapping but kind of
different vision for it Ends up,through subtle and unsubtle
(31:00):
ways, influencing it towardsthat path.
Entrepreneur gets disillusioned, no longer is happy running
their own business, no longerfeels at home in their own
business.
They probably feel shame orregret about choices they've
made.
They don't feel like they'vedone right by their customers.
They don't feel like theyreally built the thing they
wanted to build.
And then they leave and they'relike maybe they even make a lot
of money out of it.
But they and they're like maybethey even make a lot of money
(31:21):
out of it, but they're like whatthe hell happened?
Speaker 1 (31:22):
So is that the thing ultimately?
Speaker 2 (31:23):
you think there's something almost spiritual about
unfolding an idea in the waythat makes sense to you,
according to your own trueprinciples, and I think that's
what people admire about, likeSteve Jobs or like even like
right now, like much obviouslysmaller example, but like linear
.
It's like, yeah, they're doingit their way, you know, and like
(31:45):
people like that becausethere's something inspirational
about it.
There's something spiritualabout building a thing that you
dream of.
Yeah, and I think that'sactually getting emotional now.
I want to build the thing I'mdreaming of.
I don't want to build the thingthat the money person dreams of
.
Speaker 1 (31:58):
Yeah, you know, I want to invite you to stay with
that.
It's just yeah, you know, yeah,stay with that, yeah, yeah,
there's a feeling here that theyjust came up.
Speaker 2 (32:09):
It's just that, um I think it's sadness that some of
the other things that I'vewanted to build, that I've
dreamt of that, have kind ofdied.
You know, yeah, not kind ofthey died, yeah, and I could
maybe resurrect them or do a newversion of them or whatever,
but um, there's a loss there.
Speaker 1 (32:28):
Yeah, yeah, it's like one of the hard things like
it's my baby kind of a thing.
Speaker 2 (32:35):
It's obviously not.
I have kids.
This is not the same, but thereis the sense of like.
Not the same, but there is thissense of like when you really
pour your heart into somethingand then it doesn't work but you
still feel like it could've.
It's sad there's a grievingprocess there and I really don't
want that to happen for this.
(32:56):
So hence, the mom bear, get thefuck away.
Speaker 1 (32:58):
Yeah yeah, I can totally see that.
Being a repeat founder,especially is, is uh tightly
fused with having to deal withthat loss.
The sadness, things not workingout, yeah for sure, but I want
(33:21):
to reflect something real quick.
Joe, Joe, John.
The other thing that I want toreflect here is that part of
that sadness that you're intouch with is only possible
because you deeply, deeply care.
Yeah for sure, like you deeplycare, I can tell, and so it's
(33:51):
probably part of what makes youreally effective, and it's also
what is going into theseinvestor meetings that it's
going to be rocket fuel, right,this level of caring, right, and
you're present to thisprotective instinct, so that you
don't have to feel that lossagain.
Speaker 2 (34:11):
I think also this is so important.
This is becoming more clear tome.
I've had a couple ofexperiences in my career where I
felt like, oh, I'm trying tolike be open to this way or
whatever, and like it would bebetter for everyone if I like
grew to be open to this thing,and in the end actually like I
should have just said fuck thatthing.
All along, like I kind of Isort of thought you were
(34:32):
supposed to have co-founders.
I thought like it's, it'simportant to have co-founders
you know, like Y Combinator saysit, so it's gotta be true.
Speaker 1 (34:47):
Oh yeah says it, so it's gotta be true.
Oh yeah, obviously yeah, it'slike make something people want
and like have two 20 somethingtechnical co-founders.
Speaker 2 (34:49):
you know what I mean.
Yeah, the unquestioned doctrine, yeah, anyway, I'm so much
happier this is the first timeI've been a solo founder and I'm
so much happier and I'm justlike I'm.
I might have a co-founder gamefor something I do in the future
, but like, default is no forsure and and like I, I kinda I
kinda feel like, um, maybethere's something similar about,
(35:09):
like I'm supposed to raise thatother round right now.
I should be open to it.
It's, you know, blah, blah,blah.
But it's like, maybe I'm notlike and it doesn't mean
actually that I'm not interestedin building a venture scale big
thing or whatever Cause like,if I tell you about the thing
I'm dreaming of, it's obviousthat if it works, even in like a
kind of well, we got part ofthe way there, way, but like
(35:32):
something about it worked, likethat it is a venture scale idea.
But, um, maybe it's that samekind of deal.
But I can just, instead oflearning the lesson the super
hard way, uh like go with myinstinct again and just be like,
focus on getting toprofitability first and then
it's truly like a if you want it, it's on our terms kind of a
(35:52):
deal and there's no, like we'rein all the position of strength,
you know, um let's test it outfor a second.
Speaker 1 (36:00):
So so let's just say that we had the magical ability
to delete any sense that youshould be raising money, and now
all I'm going to do is ask youto just sense, feel into, like,
what is that you want to do withthis business in the present
moment?
(36:20):
What comes up?
Speaker 2 (36:23):
there's kind of two things, one for sure.
The primary thing is like justgrow revenue, get profitable.
We don't need to spend a lotmore, we just need to execute.
We need time.
We've got time.
We are executing.
Growth has picked up lately.
It feels great.
Let's just keep doing whatwe're doing.
Heads down right.
That's like 80 20 is yeah, butwe're gonna cut.
We're cutting it a little closeand like probably, unless
(36:44):
things really really start topick up, I'm gonna have to dial
some stuff back.
That's gonna be a little bitpainful to dial back.
It's not like going to totalcockroach mode, but it's.
You know, it would be so niceif I could like.
The thing that would be greatis if I could just have, like,
our existing people put more inat terms that I like, because
then it's kind of like there'sno new people in the deal.
(37:05):
But, like you know, the model ifyou're a seed fund is kind of
like you have to be prettycareful about if you're gonna
like do these sort of extensionsand whatever and it's really
nice to get the validation fromfollowing investors that, like
you're not the only one whothinks this is exciting, and,
although I understand why theyhave the model that they have,
um, but um it yeah, that wouldbe the snap my fingers thing is
(37:28):
like I'm willing to take on alittle more dilution and it
would be nice to have a littlemore padding to do the things
we're currently doing in like aslightly more robust, nicer way,
because we're uh, we've gotwe've got an ambitious like
thing that we're building andwe've got a really, really small
team.
Speaker 1 (37:44):
When we tell people our team size, it's kind of like
wow let's assume that thosethings could like you knew you
could get that.
Let's assume that you couldthat 80.
Like you knew you could execute, and then you knew that you
could go make a deal happen withyour existing insiders.
How would that feel?
Speaker 2 (38:04):
Great, yeah, just great.
I would immediately be able totake two people that are
part-time and make themfull-time and just know that we
have that much more revenue toexecute Sorry, a much more
runway to execute to get toprofitability or whatever else.
But that would be great.
Now it's kind of like we can doit, but it's kind of it's kind
of pretty close.
We're scraping by with a lot ofthings.
Speaker 1 (38:25):
yeah, yeah so let's just imagine, like, step into
that movie for a moment, so likeyou're there fully, let's just
say that, firing all cylinders,you got the extra uh padding.
Let's just pretend that's truefor a moment.
And then you go back to thiswhole thing, going out to the
market, raising the next realquote-unquote round.
(38:46):
What do you notice, you feel,as you're looking toward that Am
?
Speaker 2 (38:53):
I assuming that we raise the extra money now from
the same people.
We got the extra padding, wehired the people full-time, we
accelerated in the way that wethink we'll accelerate if we put
our foot on the gas a littleharder on some of the things
that we're currently working onand then now we're like
profitable or really close toyeah, like kind of yeah.
That's great, honestly, if Ican go to investors with just
like I'm profitable and I'mgrowing fast and I'm open to
(39:19):
taking on some more dilutionbecause we've got some specific
things we want to do and itwould be great to add more
really great people around, uh,the board, but you know, only if
they're really great peoplekind of a thing.
That's amazing.
I feel in control.
I feel great, um, because thenit's like it's truly like no
skin on my back if you don'twant to invest, or if I don't
want you to invest, or if welike each other but there's we
(39:42):
can't come to terms.
That feel like that makes sense,right, um, that feels great.
Um, if I'm kind of like I'masking you to bet early, you
know, a lot of a lot of stuff islike working but like in a
nascent way, like six moments.
Data would probably really meana lot to see if the growth
continues with this stuff,versus like it was the pop and
then kind of flattened orwhatever.
Um, it's just kind of like itfeels a lot less.
(40:05):
I feel like I'm asking them tobet on something that's more
like.
Um, there's a spectrum fromlike team and dream to traction.
Yeah and I, it would be muchnicer for the next round to be
like just total traction andwe're profitable anyway.
Speaker 1 (40:20):
So yeah, what I hear from that is, if you were to get
to that the other side of thattraction story you also you
personally would be feeling muchmore confident about what
you're asking them to invest in.
Speaker 2 (40:31):
Totally Cause yeah, I mean that's.
The other thing is if let's saythey well, they put in the
money and then a lot of thestuff that we're doing like
doesn't work as well as we hope,which sometimes that happens,
you know that's like oh shit,you know and that's also when
investors tend to get moreinvolved.
Yeah, exactly, exactly, exactly,um.
(40:53):
So anyway, um, yeah, to me thatthat's why I'm kind of like it
makes sense to just keepfocusing and that's our.
To be clear, that's like ourplan.
Like I'm not like gearing up tofundraise, you know, before the
end of the year or somethinglike that, like we're speaking
at the end of October, if it wassort of like I got a whole
bunch of convos lined up forNovember.
We want to close the round inlike December, january or
(41:15):
whatever.
On growth, but yeah, I know thatI think the calm in general,
even the conversation with ourexisting investors about what
the next round would look like,it already brought up all this
stuff, which is why I wanted totalk about it.
But it is kind of interesting.
I do think I'm feeling morelike conviction around, like
yeah, let's like let's justreally keep focusing on growing
(41:38):
revenue.
It's working, let's just keepmaking it work.
It's really hard to make itwork.
It takes a lot of focus.
I'm going to worry about thatand also manage the business in
such a way that assuming wedon't get any more money,
assuming no more investment, soaggressive but it can't die,
(42:00):
kind of a thing.
Speaker 1 (42:01):
Right.
Speaker 2 (42:01):
So yeah, yeah.
Speaker 1 (42:06):
Well, john, as we start to wrap, I want to check
in with you and ask you know wetouched quite a few different
things here today what are youtaking away from the
conversation?
What are you taking away from?
Speaker 2 (42:20):
the conversation.
The most important thing islike actually to listen to the
mama bear thing that's like getaway from my business and to
just keep unfolding, the thingthat only our team can really
see Right.
And it's a really sensitive anddelicate thing to ask someone
(42:45):
before it really is obvious tobuy in, and inevitably they have
to do so somewhat blindly.
Miracle, when that does workwith someone that wouldn't like
a seed or pre-seed investor likeactually ends up.
I think it's probably best forpre-seed and seed investors to
be just basically supportive andyou're kind of betting on
(43:08):
founders and that's the way thatthe best ones do it.
You know they're not trying tolike manage it too much um and
um.
I mean I could probably be, Icould probably be a little bit
more open to like well, thereare some people who might do the
next round that's kind of likea seed extension or series seed
(43:30):
or whatever that do share thatphilosophy and they provide
really great ideas, but theydon't threaten any real like
we're going to make you do itour way, kind of a we're gonna
try, you know, uh, kind of athing.
Um, and so I probably should bemore open to the existence of
those people.
But it's probably actuallyright for me 10 minutes in a
meeting when someone doesn't getit and they seem like not
(43:53):
really aligned, to just be.
I could be nice about it.
But it doesn't have to ruin.
It, doesn't have to make mefeel nervous at all because I
think I've got a little bit ofresidual, like I'm depending on
them, but I'm really notsignificantly anymore.
Like I think we're already atthe point revenue-wise where,
like if I had to take it down toskeleton crew, I would be able
(44:17):
to and keep it going andfinancially, like I'm in a much
better place now and there'sjust a lot of stuff that's
different about now versus yeahit's easy to forget.
Speaker 1 (44:25):
That's an option.
Speaker 2 (44:26):
The last thing but you know, it's like been, yeah,
it's been, that's been more.
It's been like eight yearssince that scenario.
So it's like, yeah, so much haschanged.
But emotionally it's like, well, it's the last time I did that
was.
So I guess it's like theemotions are kind of cached
somewhere in my life.
You're in this situation,here's what to feel, kind of
thing.
Yeah, yeah.
Speaker 1 (44:47):
And if we had more time together, I would also just
invite you to spend more timewith those feelings, so that
they wouldn't have to be socached.
Speaker 2 (44:53):
Yeah, that is very true too.
What do you think is the like?
Because the thing that Inoticed that was really
interesting is you're asking meto like stay with, like, get the
fuck away from my business.
Feeling what?
Um, it seems like there's athing that's like oh, we tend to
resist wanting to go thereemotionally, like if it starts
(45:15):
to come up, it's like, ooh, putthat away, that's dangerous,
because then it'll make me superrude during these investor
meetings and pre-reject peopleand all this stuff.
And you're kind of like, ooh,put that away, that's dangerous,
because then it will make mesuper rude during these investor
meetings and pre-reject peopleand all this stuff.
And you're kind of like no,stay with it.
I'm curious what the deal is.
Speaker 1 (45:27):
How does that work?
So, generally, when we'rerepressing an emotion because
that's in some sense that makessense for us to do that, it's
protective, it's reallyuncomfortable, yeah, you know,
we might convince ourselves thatthe emotion is like too
(45:48):
dangerous to have, it's gonna oh, it's gonna ruin my meeting.
Well, emotions are meant to befelt.
Yeah, um, they're theexperiences that are are
demanding to be felt one way orthe other, and so when we are in
, let's call them like much moreactivating scenarios, um, then
that's where we're going to belikely.
It's more likely we're going toget triggered and reactive,
versus the alternative, which is, oh, if we can actually
intentionally, consciously,allow ourselves to feel whatever
(46:10):
it is that we've beensuppressing, whether that's
anger, fear, sadness, joy I mean, there's a whole number of
these things then, in essence,what we allow ourselves to do is
build our capacity to be withthose feelings.
Right, they're not so scaryanymore for us, right?
And then, as a result, whenthey do pop up again, they're
(46:32):
not going to overwhelm us somuch.
Yeah, interesting, interesting.
Speaker 2 (46:36):
So the thing that's very new for me here is um, I
probably I didn't realize cominginto this conversation that I
kind of thought, oh, I've gotthis mama bear instinct, which
is bad.
I need your help with itbecause it's going to ruin my
chances of raising money frominvestors because I like
pre-reject them, yeah, andactually it's kind of like no,
the mama bear instinct's prettygood, and like if you have
(46:56):
someone that you're just reallynot vibing with, just go with
with it and like whatever.
Maybe there's a differentversion of you that would vibe
with them for whatever otherreason, but like whatever, it's
fine.
Like do the thing of focusingon just making a really great
business, that you're in controlof your own destiny when you
(47:16):
feel comfortable doing that,cause you're sort of embracing
that all of a sudden.
Maybe I'm a little bit more open.
Maybe when I'm talking toinvestors, it's, it's I'm I'm
less worried about am I going topre-reject them or are they
going to reject me or whatever.
I'm just focused on my businessand good things could happen.
Um, but it's kind of funnycause it's sort of like um, the
the solution is almost likethere's a thing I'm worried
(47:40):
about.
But if I actually just kind oflean into that, then it's less
likely to happen.
Speaker 1 (47:46):
More often than not it's the resistance that
actually is the obstacle and, toparaphrase it, it's what we
resist persists.
And so what I would encourageyou to do, john, is,
specifically with that mama bearimpulse, is to get more
familiar with it, move closertoward it Really, see if you can
(48:07):
inquire into its contours.
When does it come up, whattends to activate it, what are
the things about it that you canappreciate, and also where the
places where perhaps it's notserving your interests?
(48:27):
There's a whole field ofexploration that's possible
there.
Speaker 2 (48:28):
So that's that's what I encourage you to to consider
makes sense.
Love, that, I think that's.
I think that's going to help,because it's definitely not just
investors that trigger that,it's just anything that feels
like a threat to the vision.
You know, yeah, yeah, whichevolves.
You know that's right, which iskind of funny, because one
thing that seemed like a hugethreat to the vision a year ago,
now we're doing and I'm excitedabout it, yeah, so it changes.
Speaker 1 (48:54):
Yeah, yeah, absolutely Awesome.
Well, john, thank you so muchfor spending the time today.
Thank you Really appreciate it.
Today's conversation opened upsomething fascinating about how
we relate to our protectiveinstincts as founders.
When we began, john viewedtheir visceral get away from my
business response as a liability, an emotional reaction that
needed fixing.
Yet as we dug deeper, adifferent picture emerged that
(49:17):
protective instinct wasn't justemotional baggage from past
experiences.
It was actually pointing towarda deeper truth about their
vision for the company.
The venture capital pathpresents founders with a
profound paradox.
The very investment that couldaccelerate a company's growth
often comes with the risk oflosing control over its
direction.
Stories abound of founderswhose companies grew beyond
their original vision, shaped bythe pressures and expectations
(49:39):
of their investors.
Some founders look back andbarely recognize the company
they started.
Yet what our guests discoveredwas that their protective
response, this instinct tomaintain control, wasn't
necessarily at odds withbuilding a venture-scale
business.
Rather than fighting against it, they realized they could use
it as guidance to build acompany on their own terms,
first engaging with investorsfrom a position of strength
(50:02):
rather than necessity For thefounders.
Listening, think about your ownprotective responses, those
instincts that feel almostprimal in their intensity
Instead of seeing them asproblems to solve what might
happen.
If you got curious about whatthey're trying to tell you about
the company that you want tobuild, thanks for tuning in
today.
If you found value in thisepisode, I'd love for you to
share it with another founder inyour life and, if you have a
(50:22):
moment, leaving a rating orreview, helps other founders
discover these conversations.
Until next time, this has beenSlow Down to Speed Up.
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