February 20, 2024 • 45 mins
Founders that embark on a fundraise are often met with a mix of electrifying hope and gnawing doubts. In my coaching session with Nestor Solari, CEO of Sigo Seguros, we tap into that dichotomy, revealing the raw emotional journey founders undergo while chasing startup funding.
When you're in full on pitch mode, skepticism and pushback can throw you off your game. The negative emotions and stories that turn up are to be expected, but how we relate to them is what makes all the difference in our performance.
Watch the full episode on YouTube.
We cover...
- What happens when an investor pushes back
- How we typically respond internally
- How our reaction can backfire
- How to escape the trap of emotional defensiveness
Timestamps
00:50 Nestor's Intro
03:30 Losing Energy in An Investor Pitch
06:30 Negative Spiraling During The Fundraising Process
13:33 Navigating Adversarial Dynamics in Fundraising
20:04 Confronting Insecurities
31:52 Building Presence and Welcoming Emotions
44:00 Key Lessons
Enjoyed this episode? Ready to take your leadership and personal growth to the next level? Please visit my website to learn more about coaching with me.
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Transcript
Episode Transcript
Available transcripts are automatically generated. Complete accuracy is not guaranteed.
Brian Wang (00:00):
Startups are an emotional roller coaster and the
most gut wrenching parts areduring fundraising.
One moment you're riding highand the next you feel like
you're about to die.
When we're pitching, we'reoften on the edge of our seats
and we're working really hard toprove ourselves right in the
face of investor skepticism.
But is this defensive stanceuseful or might it do more harm
than good?
In today's episode, we divedeep on these questions with
(00:22):
Nesor Solari, co-founder and CEOof Cigo Seguros.
We explore the turbulentfeelings that come up during the
fundraising process and theimpact they can have on our
success.
We get into what happens whenan investor pushes back, the
ways that we typically handleourselves and how we can escape
the trap that can cripple anyfundraising effort.
Let's dive in.
Hey Nesor, great to see youtoday.
(00:42):
Hey Brian, good to see you too.
So just to give the audience alittle bit of a sense of who you
are, nesor, you're the founderand CEO of a great company
called Sigo.
You and I have been workingtogether for some time now, and
what's really interesting aboutour history is that we worked
together for a while, we took abreak and then, when you came
back to pick up the work with me, the company had really shifted
(01:05):
.
You guys had just started toreally hit the accelerator in
your growth, and so, as yourcoach, I've had a lot of fun
just watching the differentphases of the company in its
journey and the twists and turns, and, of course, just watching
you grow through that wholeprocess.
And so, yeah, I'm really justexcited to get on this
particular session with you onthe show, and I just wanted to
(01:27):
give you a chance to justintroduce yourself and, of
course, maybe talk a little bitabout just what we're here to do
today.
Nestor Solari (01:34):
Thanks.
Brian Wang (01:34):
Brian.
Nestor Solari (01:35):
Thanks for having me.
Always a pleasure to spend sometime together.
I guess quick background on meborn and raised in New Jersey,
parents are Uruguayan immigrants.
I think, after working my wholecareer in finance, saw an
opportunity to help theimmigrant communities with
(01:56):
better insurance or a betterauto insurance option and kind
of.
That's what launched my journeyinto building Sigo during
business school.
I think as I started researchingkind of the founder journey and
following founders I reallyrespected and looked up to,
(02:17):
coaching was one thing that cameup and particularly a founder
that I had been following andhad a lot of respect for spoke
very highly of you and sothankful we were able to get in
touch and start working together.
I think it's been an incrediblejourney building and so very
professionally rewarding but Ithink, very personally rewarding
(02:40):
as well, and a lot of thatthanks to some of the work we've
done.
As I reflected on the thingsweighing down on me and the
things that I wanted to talk toyou about, obviously a big part
of my job is fundraising andhaving investor conversations
(03:07):
from day one through maybe thelife of the company, but
particularly through these earlystages and no matter how well
the company is doing and howstrongly I feel about our
performance and how strong myconviction in the opportunity is
.
I tend to find myself losing alot of energy in some investor
(03:31):
conversations that might not gothe way I expected them to go.
So I thought we might be ableto explore that a bit together
and dig and see, maybe, whatbiases I have or what things
might be impacting my mood or myperformance ultimately.
Brian Wang (03:50):
Yeah, great.
So you're no stranger tofundraising.
I know you've really beenthrough that process quite a few
times.
You guys have raised actuallyquite a bit of money, so I know
that also.
You're pretty good at it too.
And so you mentioned thisenergy thing how it can feel
draining for you, and I knowthat there's this concern around
(04:12):
performance.
I'm wondering if you can maybejust expand on that, talk a
little bit about what youexperience in so many situations
where it doesn't meet yourexpectation, energy shifts, and
just go back into this partwhere it's like oh yeah, now I'm
not performing the way I wantJust say more about that.
Nestor Solari (04:32):
Yeah, and I think it's a lot of.
It starts with kind of psychingmyself up, I think, for getting
myself excited for a lot ofthese conversations.
But I think, going intoconversations, especially
recently, I've been veryconfident again about the
(04:53):
business.
I think I've been very excitedabout the business and I go in
expecting to share amazingmetrics and growth and what have
you with an investor.
And I find that if that doesn'tseem to land the way I intend
(05:18):
or if the investor's reactiondoesn't seem as positive as I
would expect, that that feels inmy mind like it throws me off
balance.
I think I kind of go in with aclear game plan.
Fundraising is a game of beingmeticulously detail oriented and
(05:41):
planning out your investor listand your materials and being
very thoughtful about how you doall of that and putting it all
together.
And so it feels like when you gofrom the structured Excel file
and data room and kind of clearframework or equation for a good
pitch deck for your series A,then I kind of go into maybe
(06:03):
this less structuredconversation or environment
expecting that kind of my A plusB is going to equal C and what
it equals X.
I find to kind of get maybethrown off balance and I find
that that maybe translatesitself to being flustered in a
(06:29):
conversation or not answeringquestions as crisply as I would
like to, and I feel like maybethat kind of sets me into maybe
some sort of spiral.
But then one conversation goespoorly and then it seems like
that bleeds into the nextconversation and then it bleeds
(06:50):
into my preparation for nextweek Whenever I take a second to
reflect on it.
I know there's a lot of factorsoutside of my control here, but
it tends to feel like a bit ofa bit of that failure and I
(07:10):
think as founders a lot of ushave a fear of failure and kind
of feeling in that conversation,maybe as a peak into what
happens if you don't put thisfundraise together.
Brian Wang (07:23):
Okay.
So you're already jumping intothe uh-oh, I'm feeling like a
failure part.
You're skipping ahead.
So let me reflect a little biton what I just heard you say,
nestor.
So one of the things that jumpedout at me was the word
expectation.
So the way that you framed it,it sounded like, oh, there's a
(07:47):
game that I'm playing, which isI put together the right pitch
with the right narrative and thedata room and the process and
the investor list, and once Iexecute these steps in the right
sequence, then you know it'slike I hit these keystrokes and
(08:07):
then out comes money Right, notto be too reductive and then
when the reality doesn't meetyour expectation you talked
about that messy, unstructuredinteraction you go in thinking,
if I say the right things, theeyes will light up and then
there's going to be the money.
(08:27):
Then in that unstructured placewhere perhaps it feels a lot
more dynamic right, I don't knowwhat's going to happen in here.
That's where it feels like youlose your footing a little bit
and your mind starts to go intomore of this kind of negative,
contracted place.
Uh-oh, not going well, maybeI'm going to fail that sort of
(08:50):
thing, right?
So the big thing I'm hearing isthis expectation thing?
I'm wondering, just as I makethat simple reflection, what's
coming up for you as I point outthis expectation component.
Nestor Solari (09:08):
Yeah, I think a lot of what we talk about as a
team at CEO is kind of settingexpectations with each other,
with ourselves, with our clients, their customers, and it's
funny and sometimes you kind ofdon't realize the expectations
you're setting for yourself.
But that resonates for me and Iguess what that takes me to is
(09:35):
well, if my expectations aren'tmet, it feels like I might
immediately start searching for,okay, what's the right formula
here, what's the right next step, or how do I get this back on
track when maybe it's not offtrack?
Yeah, that's kind of what cameup for me is kind of, what does
(09:57):
this look like if I go into itwithout expectations?
or with less expectations ormore flexible expectations.
Brian Wang (10:07):
Have you ever been in a conversation with somebody
where it felt like they werecoming into it with a whole
bunch of expectations of how itwas going to turn out?
Like they had an agenda withhow it was going to go.
Sure, yeah, how did that feelfor you.
Nestor Solari (10:28):
Off-putting is the first word that comes to
mind.
If I know someone comes to thecall with an agenda, you're kind
of on guard.
And I mean I guess especiallyin the checkwriter, check
receiver kind of founder,builder, investor type
(10:51):
relationship, it almost seemslike there's those preconceived
notions, the notion of an agendakind of baked in.
Brian Wang (11:01):
Right, yeah, there's some dance that we do some part
to play.
Nestor Solari (11:10):
But if we take it out of that context, kind of
being in a conversation withsomeone that seems to already
have an agenda or have a waythat they think they should go,
kind of puts me on the defensivea bit.
Brian Wang (11:22):
How do you start to feel toward that person in
particular in that moment?
Nestor Solari (11:26):
Well, you kind of almost get the sense that
they're trying to manipulate you, right?
I think that getting put inthat guard also, it's
antagonistic, almost right.
It's, yeah, you feel like youshould be putting pressure back,
(11:47):
almost, that you need to slowthis agenda down a bit or slow
this person down to make sureyou're not being taken advantage
of.
Brian Wang (11:58):
Yeah, so the word that came up for me was like
that feels adversarial.
Nestor Solari (12:04):
Yeah.
Brian Wang (12:05):
Right, you versus me .
Let's see who's going to win.
Yeah, so yeah, you've got tolook on your face.
For those who are justlistening to audio, they can't
see this, but I'm curious what'srunning through your mind and
your heart as this is processingthrough you.
Nestor Solari (12:25):
Well, I think the first thing that I'm thinking
about is kind of thisadversarial nature of these
conversations.
It really doesn't feel likethat is how it is with my
largest investors and with mostsuccessful founders and their
(12:47):
best kind of investorrelationships, and kind of
adversarial doesn't seem toquite accurately describe kind
of how the relationship shouldbe right.
Ideally we're both winning andthere's a couple scenarios where
one wins and the other oneloses.
But I think in the bestoutcomes the investors and the
(13:09):
founders kind of are both kindof aligned and trying to move in
the same direction, right, andso I wonder how it gets there
from here.
A bit is kind of what I wastrying to work through in my
mind and was putting that lookon my face.
Brian Wang (13:27):
Yeah, yeah, yeah, great.
So I think you're totally right.
Ultimately, when you're raisingmoney, you're looking for
partners.
You're looking for people whoare aligned with your vision,
they're excited about yourvision, they're going to support
you with capital and resourcesand all sorts of things.
To start that off from anadversarial frame feels like an
(13:51):
uphill battle, right, Because itbecomes like a you versus me
thing, and that's pretty faraway from hey, we're on the same
team, we're allies now, right.
So I guess the question that'scoming up for me now is, when
you find yourself in thosesituations, right, where it ends
up feeling a little adversarial, this is an open question.
(14:16):
But what is it that's drivingthat on your end?
Nestor Solari (14:24):
And I'm thinking about a couple of different
conversations and I'm thinkingabout, okay, when I felt this,
what memories this feelingbrings, but I think there are a
couple.
I think sometimes it might feellike it's triggered by I don't
(14:46):
know if it's a question or areaction to something I say,
which I think is the first onewhere I'll present something as
a truth or as my experience oras something as I know.
And then the person across thetable maybe the story I'm
(15:08):
telling myself is that they'rebeing cynical and disagreeing
with me, just to be kind of playdevil's advocate, possibly, and
I feel like that kind of setsus up to butt heads.
That feels like it might be themost common experience, the
most common story I have in myhead about when this happens.
Brian Wang (15:30):
Can you?
I'm wondering if you can maybeput yourself in a specific
situation where that happenedrecently, one where this kind of
feels real to you.
You don't need to name names,of course, Sure.
Nestor Solari (15:42):
You know, I think one that feels common, almost
like a recurring dream right now, is, I think, in the auto
insurance sector in general.
It's very competitive.
Some see it often as a kind ofcommodity product, whereas the
truth is it's quite nuanced andthere's a lot of variation in
(16:06):
auto insurance and the type ofcoverage, and I think that's
something I've learned throughmy experience and working with
immigrant communities andselling lower coverage limits
versus maybe what I'm used tobuying from Geico, and so a lot
of times when I try tocommunicate that nuance or that
(16:27):
difference, I think I sense, orthe story I tell myself about
how others react, is that theydon't believe me.
They believe that these largecompetitors will easily put us
out of the business once weprove that we can do this
(16:49):
profitably or whatever it is,and that seems to be something
that I've practiced a lot sinceearly days in trying to explain
the nuance and speak around, butstill something that feels like
it's a challenge to get aninvestor to digest, especially
if they're learning about thissegment for the first time.
Brian Wang (17:12):
Okay, so you've got this experience where you've
gleaned some important, nuancedinsights about this market.
And then you go into thesemeetings and you say, hey,
here's something reallyinteresting that we've learned,
that we've learned that weunderstand a certain truth about
the space that we're working in.
We'd like to share it with you.
And then the response is almostit sounds like there's a
(17:39):
dismissal, there's a yeah, but Ithink you guys are going to get
crushed and I want to see if wecan maybe then take that moment
that I'm describing and zoom ina little bit into your
experience here.
So in the moment where you,where that resistance comes up
now here's why that's not goingto work, et cetera, right, what
(18:02):
do you notice?
You start to feel in yourinternal reaction there.
Nestor Solari (18:08):
Get defensive.
Almost feels like I lean in andput my shoulder down a bit.
It feels a certain tightness inmy, in my shoulders and chest
Feels like my, my almost kneejerk or immediate response is to
(18:29):
start trying to spit out thedozen reasons why I quote
unquote.
No, they're wrong.
Brian Wang (18:38):
Okay, so there's a defensiveness, your body starts
to shift.
It's like it's almost like it'skind of like almost collapsing
a little bit.
If I heard that correctly,there's a little bit of a
curling, there's a, there's aneed to defend something we
could spend some time namingthat but you're, you're now,
you're on the defense, and thenalso like but wait, let me
(19:01):
explain why you're wrong, right,which then sounds like it's
like a little bit of this now isback and forth, right, and so,
if you can just stay in thatspace for a moment, that
defensiveness, connect with thatdefensiveness now.
Now I want to ask, underneaththat, what are you starting to
believe about yourself and whatare you starting to believe
about that person in thatsituation?
Nestor Solari (19:22):
So, like there, this is maybe a little mix
between what I believe and theybelieve, or maybe what I believe
about what they believe.
Sure, yeah.
Brian Wang (19:30):
Yeah, what you're projecting onto them, sure.
Nestor Solari (19:32):
Yeah, exactly, I think there is.
Well, I must not be credible asa founder if they don't believe
what I'm saying to them, orthis investor is not
sophisticated or is not or isintentionally offensive.
I'm not intentionallyobfuscating my point because
(19:59):
they have some bias against whatme or what I'm doing.
The other one that comes up iskind of almost kind of a need or
a or it feels like a thirst toprove myself right.
If this person doesn't believeme, then that means I'm wrong,
whereas that, saying that outloud, all of us like.
(20:24):
Well, I don't need them tobelieve me for me to believe me,
to believe myself and know thatthis is my truth or my
experience.
Brian Wang (20:32):
Yeah, I know you get that on an intellectual level.
Nestor Solari (20:37):
That's the challenge.
Brian Wang (20:38):
Yeah, but it sounds like, just to paraphrase, if
this person you see this datapoint this person doesn't seem
to believe me.
And now this must meansomething about me.
I'm not credible, I'm notbelievable.
I must be wrong here.
And I just want to slow downand notice just let us both
(21:03):
notice how you jump from thisperson.
It doesn't get what I'm sayingor disagrees, and then the
conclusion jumps right to oh,that must mean something about
me, that must mean somethingabout my own competence or
credibility.
And then the move to defendoneself, to prove oneself.
Nestor Solari (21:28):
So what that makes me think about is well, if
I were competent and credible,then why wouldn't they believe,
right?
And then I guess there's well,there's a step between me being
competent and credible andseeming, in another person's
eyes, to be competent, credible.
Those are two different things.
And then there's also the well,whether it seems or I am,
(21:59):
there's other reasons why theymay not believe something,
despite my competence andcredibility.
Brian Wang (22:06):
Sure, yeah, I can see you jump into the
alternative reasons.
Absolutely.
What I hear is that there's anexperience that you have about
around this feeling of, oh, I'mnot credible, I need to prove
myself.
Where has he felt that?
Does that feel familiar to you,even outside of this context?
Nestor Solari (22:25):
Reminds me of interview processes throughout
my career before being a founder, Interviewing and not getting
the job that feels that's astrong feeling.
Brian Wang (22:39):
Yeah, what's the feeling if you were to name it?
Nestor Solari (22:46):
Is it inadequacies?
I think is.
The thing is well, I know I cando this job and I'm trying to
communicate that but I can't, soI'm inadequate in some form and
then I don't get the job.
Brian Wang (22:57):
So that confirms that, this inadequacy- when did
you first get that message Insome sense that you're
inadequate?
Nestor Solari (23:07):
Going back failing tests.
I can't remember necessarilygetting an F on a test ever, but
I do remember not getting theA's that I expected to or wanted
to.
Let me see if there's somethingfurther back.
I can even kind of maybe likefriend groups as a kid.
(23:32):
It feels like that's as likeyou're kind of embarrassed in
school for whatever reason and Ican't can't come up with a
specific example but you thinkabout like yeah, you know, we
almost feel similarly to theinterview.
It feels like when you're a kidand you tell the the, the girl
(23:52):
you like, that you like them andthere's no reciprocation there,
right?
It almost feels like well, by bydefault.
A lot of the the investorconversations feel like it's
almost like an opt-in by thefounder and then it's up to the
investor to make the decision,until that's the point that that
(24:16):
power dynamic shifts right.
Brian Wang (24:20):
Right, it feels like there's this person has power
over you.
I need to get their approval, Ineed to win their approval.
And then, when you don't getthat, it feels like that.
There's that feeling ofinadequacy.
I didn't, I didn't win theapproval because I'm somehow
inadequate.
And when you're, when you're inthat, in the middle of that
(24:42):
feeling, live, what's the?
What's the urge, right, what'sthe, what's the thing that your,
your system is like justspringing to want to do, then
Feeling frustration, feelinggritting, grinding my teeth,
(25:03):
maybe sadness, tears even.
Nestor Solari (25:07):
It's just kind of like above level of frustration
.
Brian Wang (25:12):
Yeah, I wonder if you can connect with that a
little bit, the cherry feeling,the sadness, and what's that
bringing up for you.
Nestor Solari (25:28):
Whenever that sadness comes to mind and I
don't know if it's I'm feelingbad about myself or I feel like
I'm being a little too mean tomyself I think one thing from
previous coaching I think Ithink of myself as a little kid
(25:50):
with those emotions.
Sure, it's just feeling thatcompassion, that's kind of what.
Those feeling, that emotion andfeeling that I may be exposing
myself to or kind of, or kind ofputting myself in that, in that
(26:11):
headspace or that position.
It feels almost like I'm notshaming myself, I'm punishing
myself, and then that kind ofmakes me step off and be like,
well, chill out, man.
Sure, don't be so hard onyourself.
A little bit is the.
(26:32):
Thing that comes to mind.
Brian Wang (26:34):
Yeah, so you just walked us through a kind of a
series of steps here.
Right, the way you start torelate to yourself or different
parts of yourself, but I don'twant us to necessarily skip over
the part where you feel thatfrustration and sadness.
I think I hear that it's likeokay, don't be so hard on
(26:55):
yourself.
Yeah.
Nestor Solari (26:57):
I think one thing that's triggered there is.
Well, I don't want to be toohard on myself because I don't
want to feel this.
Brian Wang (27:07):
Feel what exactly.
Nestor Solari (27:09):
Feel this kind of frustration, or this sadness,
or this gritting my teeth, kindof fighting, crying, kind of
feeling.
Brian Wang (27:19):
What I hear in that is there's like I'm gritting my
teeth hard to hold back fromsomething.
It's like you're clenching sothat, so as to not feel
something under that.
What's that?
Nestor Solari (27:33):
Almost and maybe it's that sadness or that.
Yeah, it's funny that just thatreaction to not let yourself
feel this, so anythingunpleasant seems like your first
.
My first reaction is let me tryto do something or say
(27:56):
something to not let myself feelthat.
Brian Wang (28:01):
I think you're doing it right now.
Nestor Solari (28:02):
Yeah.
Brian Wang (28:03):
Yeah, what happens if you just allow any of that in
for a moment?
Nestor Solari (28:11):
I feel lighter.
Brian Wang (28:16):
You might ask this part of yourself that feels sad.
What does it want you to know?
Nestor Solari (28:23):
I don't know if this is just the reaction to not
feeling it, but maybe kind ofdon't be hard on yourself, don't
be so hard on yourself, don'tinflict this.
Brian Wang (28:42):
Because you're sad about how hard you are on
yourself.
Nestor Solari (28:47):
Maybe, or that I'm sad because I'm being hard
on myself for not achieving whatI expected to achieve in that
moment, and so I tell myselfthat I'm not good enough or that
I'm not performing as well as Ishould be and that makes me sad
(29:07):
.
But then, kind of exploringthat sadness, it's like, well,
maybe you need to reevaluatethat reaction, right, reevaluate
that it's not the lowerstandard.
I think that it starts gettingreally cloudy when you think
about kind of keeping mystandards high and working hard
(29:29):
and making myself kind ofoutperform versus this kind of
maybe extreme, like hard lyingstance of anything not going my
way is immediately my fault.
That needs to be corrected.
Brian Wang (29:51):
Well, there's a world where you can have a lot
of high standards and reallyseek to achieve without really
ripping into yourself when youdon't actually succeed in some
of those things.
If I'm tracking you, there'ssome party that feels sad that
(30:12):
you're not hitting some of thoseoutcomes.
Is that?
Nestor Solari (30:16):
accurate.
I think that's right yeah.
Brian Wang (30:18):
Okay, yeah, yeah.
What's wrong with feeling sadabout those things?
Nestor Solari (30:28):
I smile because I think this is that fear, pain,
sad avoidance oftentimes createsa lot of these challenges and
just not being willing to feelsomething in a moment or sit
with something in a moment.
So I start reacting and kind ofgo on autopilot a bit.
Brian Wang (30:55):
What I hear is that the disappointment and the
sadness in that moment where youdon't meet the expectation,
feels so bad that you resist it,and then that resistance
creates the knee-jerk reaction.
I have to defend myself now.
I have to prove myself now.
Yeah, does that land?
Nestor Solari (31:21):
It does Just always, kind of coming back to
this, a lot of the unwantedbehaviors that we work through
together, I think, stem fromavoiding a feeling or kind of
(31:41):
maybe escaping thatconsciousness almost Sure, and
hey, I don't want to sit withthis because it's uncomfortable
or it doesn't feel nice.
Brian Wang (31:52):
Yeah.
Nestor Solari (31:54):
But not that what you do to avoid that feels too
much better, right.
Brian Wang (31:58):
Sure, but it's familiar.
Nestor Solari (32:02):
Yeah, yeah, yeah.
Brian Wang (32:05):
So let's play with this.
How might these situationschange, these conversations,
these interactions withinvestors change, if you didn't
fight yourself so hard Like?
Fight that sad reaction, fightthe disappointment, instead of
just allow yourself to have that?
Nestor Solari (32:25):
It feels like they would slow down a bit,
which might play to my favor tobe able to clearly communicate
what the point I want to getthrough and maybe owning that
conversation a little more.
But the first thing that reallycame to mind was right now it
feels like these become a bit ofa chain of events where it kind
(32:50):
of keeps compounding and justkind of like running through and
pushing through and just doingwhat you're feeling or want to
do and through and then hopingit kind of comes out on the
other end versus works out onthe at the end of like all,
versus almost handling thesemore on a conversation per
(33:11):
conversation basis and maybeunblinking them.
Brian Wang (33:16):
It's like you go on autopilot through the rest of
your conversations, almost likesomething takes, something takes
over, and you're like what Igot to?
Just kind of like power throughthese.
Now, right, I would imaginethat that would leave you
feeling probably less connectedto not just yourself but also to
the person that you're talkingto.
Nestor Solari (33:39):
Exhausted thinking about it.
Yeah, just have these kind ofback to back to back phone call
days and that's just not givingyourself that space or that room
to breathe and reflect and sitwith yourself for a moment.
Brian Wang (34:01):
What comes up for me is the word presence.
When we enter into thatautopilot state, often because
there's some feeling that wereally don't want to be with, we
lose presence with ourselvesand we certainly lose presence
with the people that we're with.
Those conversations lose a lotof their dynamic potential.
(34:26):
Very, very hard for us to dancein the moment with whatever's
coming up, because our agenda isjust to move on through there.
Let's get to the thing here.
We all experience that when welose presence and that starts
with ourselves we lose presenceand then everyone else around us
(34:48):
can feel that.
Nestor Solari (34:51):
It's funny, one of our values at CGO is to be
engaged and I think it'sprecisely speaks to kind of
being present with each otherand making that time together
valuable by being there witheach other.
I think a lot of times it's inthe kind of especially in the
(35:12):
virtual world and the phonecalls it kind of feels like
you're kind of alone, eventhough you're on kind of the
other side with somebody, andeven not being engaged with
yourself by yourself.
Like avoiding those feelingsseems like it's almost like a
(35:34):
kind of self perpetuating kindof vicious cycle.
Brian Wang (35:40):
Oh sure, yeah, we're constantly inviting others to
engage in certain behaviors.
We model so much of thebehavior that then occurs around
us.
I want to ask you what are youseeing at the moment?
That wasn't so clear when westarted.
Nestor Solari (36:00):
A couple of things come up for me.
I think one is maybe thinkingabout the triggers here and
thinking about different ways tomaybe recognize when I'm in
that triggered state and whetherit's taking a breath or taking
a moment and kind of thinkingabout, okay, how can I come out
(36:22):
of it.
But I think kind of going intothat triggered state is
something that I feel that I'vehad it really appreciated.
I felt, okay, I'm going intothis level headed and I'm
approaching this and our streetfolks are going forward fashion,
but the outcome is what'sweighing on me, whereas it's
(36:47):
obviously feels a bit morecomplex, in that it's not just
the, it's not really the outcomethat's weighing on me, it's the
whole process and kind of addsup.
So I think if I at thebeginning of this I probably
would have said the outcomes ofthese conversations are weighing
down on me, because now itfeels like maybe, well, my
reaction to others, reactionskind of take me out of being
(37:12):
present, which leads me downthis, this kind of maybe dark
alley and so, whereas before Imay have been more prone to
accept, well, like this is justwhat happens when I have a bad
conversation, maybe say, well,was that a bad conversation.
(37:35):
Really, it's okay if it was abad conversation and it's okay
if I feel bad about whateverhappened, but that doesn't
translate to all theseconversations having to be bad.
It doesn't translate to mycredibility or my confidence or
(37:57):
my conviction in what I'm doing.
Brian Wang (38:00):
I don't have to translate into this adversarial
thing.
Now I have to really provemyself.
Nestor Solari (38:07):
Yeah, what if I was okay, not knowing exactly
what they thought?
And even if I knew what theythought, what if I was okay with
it, even if it wasn't what Ithink?
Brian Wang (38:20):
I'll simplify that for you.
What if I was just okay?
Nestor Solari (38:26):
Sounds tough.
What if I was just okay?
Brian Wang (38:35):
That, by the way, also includes whatever the
emotional state is.
What if my sadness was okay?
What if my disappointment wasokay?
Nestor Solari (38:57):
What's coming for me is thinking about okay if my
disappointment or my sadness isokay, yet still want to use
those as tools.
Right, you kind of use sadnessto push towards happiness or you
use disappointment to pushtowards success or
accomplishment.
Feels like the toolkit thatI've long used.
(39:18):
Maybe it isn't necessarily aseffective of a toolkit anymore.
Brian Wang (39:27):
What you just said was let me go take this emotion
and change it or fix it orsomething.
Versus what if it was just okayfor me to be sad right now and
then, if I just allow myself tofeel that eventually it'll move
through me and then I can moveon.
Nestor Solari (39:47):
Yeah, you kind of look at, I think happy inside
is a good, a good way to playwith, right, because you almost
think, okay, if I'm feeling sadand I don't do anything about it
, then I might never be happy,right, okay, if you're sad and
(40:08):
it goes through you, you canalso be happy in the future, and
it doesn't necessarily have tobe a result of you forcing your
sadness away, right.
Brian Wang (40:19):
Yeah, emotions are kind of funny.
That impulse is, oh I'm feelingthis feeling, I'd better go fix
it.
And in my experience that's notreally how emotions work.
They're not there to be doneaway with or to be treated as a
problem.
They might point to certainthings that matter to us.
(40:41):
They point to needs and help usmove toward the things that we
need and that we value.
But when we treat them asproblems inherently, that's
where all of the avoidancebehaviors start to come in, or
the numbing behaviors start tocome in, or the defensive
behaviors start to come in,right.
(41:02):
But if we knew that, thefeeling itself, that's okay, let
me have it, let me see whatit's about.
We'll commit maybe and we startto shift the way that we relate
to it, and then all theavoidance stuff doesn't become
necessary anymore.
Nestor Solari (41:25):
And the avoided stuff is where the problem lies,
right.
Brian Wang (41:30):
No, that's up for you to decide.
Nestor Solari (41:33):
I'll make sure I'm okay with my feelings.
Brian Wang (41:38):
Let me just check in with you as we start to wrap
here.
So take a step back.
Kind of covered a lot here.
What would it look like for youjust to move this forward a
little bit?
Take this forward.
Nestor Solari (41:51):
I guess the one thing that I'd take away from
here it's okay to feel myfeelings and let's kind of
practice doing that, so kind ofsome sort of maybe mindfulness
practice or some kind of justsome checking in with myself on
my feelings and my reactions Ithink is what I need to do and
(42:17):
kind of maybe be moreintentional about it.
I think this space, thiscoaching space, is always very
helpful to slow down and thinkabout these things, and I think
I need to be more consciousabout working this into my
personal toolkit, because itfeels like we were able to just
(42:39):
kind of unpack something andkind of bring it to this core
issue of avoiding this feeling,and I think that the key thing
is working on not avoiding thefeeling.
Brian Wang (42:57):
Yeah, and just to build on top of that, there is
this, the fundamental checkingin.
Can I check in and see whatemotions are present here,
what's wanting my attention,what wants to be felt here?
And I like to use the wordwelcome, can I welcome this that
(43:18):
there's an activeness to thatright Rather than it's like I'm
not going to resist there's awelcoming and then see what
happens there.
Nestor Solari (43:24):
You know what else comes up for me when you
say welcoming kind of evenhonoring kind of the evolution
of the human brain, the factthat those feelings are there
for a reason that would sufferall of us to maybe comprehend,
(43:47):
but being okay with it and kindof sitting with it and exploring
it and appreciating it.
Brian Wang (43:56):
That feels like a good note to end on.
Nestor Solari (44:00):
Thank you as always, Brian.
Brian Wang (44:02):
Most people know that raising money requires you
to tell a great story, but italso requires you to connect
with the investor on the otherside.
That's really hard to do whenyou get thrown off during the
meeting.
Make no mistake, savvyinvestors will push back and ask
questions.
It's part of their job.
In Nestor's case, when he gotpushed back, he internalized it
as inadequacy and rejection, aswell as feelings of sadness and
(44:24):
frustration.
All of these are perfectlynormal reactions.
The trouble comes when we clampdown on those emotions and then
we get really rigid in themeeting and then we start to
bring an unproductive energy tothe rest of that conversation as
well as subsequent meetings Inour session.
Once Nestor allowed himself tofeel his own sadness, it started
to get lighter for him.
His feelings had less weightand his stories had less grip on
(44:46):
him.
The welcoming of his innerexperience led to more freedom
and resourcefulness for him.
As the saying goes, what youresist persists.
Fundraising is a full contactsport.
You have to be willing to fullyembrace the experience,
emotions and all.
So if you are or are about togo fundraising, ask yourself if
you're willing to fully embracethe experience and if you're not
(45:08):
, ask yourself what you wouldrequire in order to do so.
Thank you for listening.
To Slow Down, to Speed Up.
If you enjoyed this episode,please rate it in your favorite
podcasting app, and if you're afounder looking to get to the
next level through coaching orcome on the show, please contact
me at dashingleadershipcom.
Startups are an emotional roller coaster and the
most gut wrenching parts areduring fundraising.
One moment you're riding highand the next you feel like
you're about to die.
When we're pitching, we'reoften on the edge of our seats
and we're working really hard toprove ourselves right in the
face of investor skepticism.
But is this defensive stanceuseful or might it do more harm
than good?
In today's episode, we divedeep on these questions with
(00:22):
Nesor Solari, co-founder and CEOof Cigo Seguros.
We explore the turbulentfeelings that come up during the
fundraising process and theimpact they can have on our
success.
We get into what happens whenan investor pushes back, the
ways that we typically handleourselves and how we can escape
the trap that can cripple anyfundraising effort.
Let's dive in.
Hey Nesor, great to see youtoday.
(00:42):
Hey Brian, good to see you too.
So just to give the audience alittle bit of a sense of who you
are, nesor, you're the founderand CEO of a great company
called Sigo.
You and I have been workingtogether for some time now, and
what's really interesting aboutour history is that we worked
together for a while, we took abreak and then, when you came
back to pick up the work with me, the company had really shifted
(01:05):
.
You guys had just started toreally hit the accelerator in
your growth, and so, as yourcoach, I've had a lot of fun
just watching the differentphases of the company in its
journey and the twists and turns, and, of course, just watching
you grow through that wholeprocess.
And so, yeah, I'm really justexcited to get on this
particular session with you onthe show, and I just wanted to
(01:27):
give you a chance to justintroduce yourself and, of
course, maybe talk a little bitabout just what we're here to do
today.
Nestor Solari (01:34):
Thanks.
Brian Wang (01:34):
Brian.
Nestor Solari (01:35):
Thanks for having me.
Always a pleasure to spend sometime together.
I guess quick background on meborn and raised in New Jersey,
parents are Uruguayan immigrants.
I think, after working my wholecareer in finance, saw an
opportunity to help theimmigrant communities with
(01:56):
better insurance or a betterauto insurance option and kind
of.
That's what launched my journeyinto building Sigo during
business school.
I think as I started researchingkind of the founder journey and
following founders I reallyrespected and looked up to,
(02:17):
coaching was one thing that cameup and particularly a founder
that I had been following andhad a lot of respect for spoke
very highly of you and sothankful we were able to get in
touch and start working together.
I think it's been an incrediblejourney building and so very
professionally rewarding but Ithink, very personally rewarding
(02:40):
as well, and a lot of thatthanks to some of the work we've
done.
As I reflected on the thingsweighing down on me and the
things that I wanted to talk toyou about, obviously a big part
of my job is fundraising andhaving investor conversations
(03:07):
from day one through maybe thelife of the company, but
particularly through these earlystages and no matter how well
the company is doing and howstrongly I feel about our
performance and how strong myconviction in the opportunity is
.
I tend to find myself losing alot of energy in some investor
(03:31):
conversations that might not gothe way I expected them to go.
So I thought we might be ableto explore that a bit together
and dig and see, maybe, whatbiases I have or what things
might be impacting my mood or myperformance ultimately.
Brian Wang (03:50):
Yeah, great.
So you're no stranger tofundraising.
I know you've really beenthrough that process quite a few
times.
You guys have raised actuallyquite a bit of money, so I know
that also.
You're pretty good at it too.
And so you mentioned thisenergy thing how it can feel
draining for you, and I knowthat there's this concern around
(04:12):
performance.
I'm wondering if you can maybejust expand on that, talk a
little bit about what youexperience in so many situations
where it doesn't meet yourexpectation, energy shifts, and
just go back into this partwhere it's like oh yeah, now I'm
not performing the way I wantJust say more about that.
Nestor Solari (04:32):
Yeah, and I think it's a lot of.
It starts with kind of psychingmyself up, I think, for getting
myself excited for a lot ofthese conversations.
But I think, going intoconversations, especially
recently, I've been veryconfident again about the
(04:53):
business.
I think I've been very excitedabout the business and I go in
expecting to share amazingmetrics and growth and what have
you with an investor.
And I find that if that doesn'tseem to land the way I intend
(05:18):
or if the investor's reactiondoesn't seem as positive as I
would expect, that that feels inmy mind like it throws me off
balance.
I think I kind of go in with aclear game plan.
Fundraising is a game of beingmeticulously detail oriented and
(05:41):
planning out your investor listand your materials and being
very thoughtful about how you doall of that and putting it all
together.
And so it feels like when you gofrom the structured Excel file
and data room and kind of clearframework or equation for a good
pitch deck for your series A,then I kind of go into maybe
(06:03):
this less structuredconversation or environment
expecting that kind of my A plusB is going to equal C and what
it equals X.
I find to kind of get maybethrown off balance and I find
that that maybe translatesitself to being flustered in a
(06:29):
conversation or not answeringquestions as crisply as I would
like to, and I feel like maybethat kind of sets me into maybe
some sort of spiral.
But then one conversation goespoorly and then it seems like
that bleeds into the nextconversation and then it bleeds
(06:50):
into my preparation for nextweek Whenever I take a second to
reflect on it.
I know there's a lot of factorsoutside of my control here, but
it tends to feel like a bit ofa bit of that failure and I
(07:10):
think as founders a lot of ushave a fear of failure and kind
of feeling in that conversation,maybe as a peak into what
happens if you don't put thisfundraise together.
Brian Wang (07:23):
Okay.
So you're already jumping intothe uh-oh, I'm feeling like a
failure part.
You're skipping ahead.
So let me reflect a little biton what I just heard you say,
nestor.
So one of the things that jumpedout at me was the word
expectation.
So the way that you framed it,it sounded like, oh, there's a
(07:47):
game that I'm playing, which isI put together the right pitch
with the right narrative and thedata room and the process and
the investor list, and once Iexecute these steps in the right
sequence, then you know it'slike I hit these keystrokes and
(08:07):
then out comes money Right, notto be too reductive and then
when the reality doesn't meetyour expectation you talked
about that messy, unstructuredinteraction you go in thinking,
if I say the right things, theeyes will light up and then
there's going to be the money.
(08:27):
Then in that unstructured placewhere perhaps it feels a lot
more dynamic right, I don't knowwhat's going to happen in here.
That's where it feels like youlose your footing a little bit
and your mind starts to go intomore of this kind of negative,
contracted place.
Uh-oh, not going well, maybeI'm going to fail that sort of
(08:50):
thing, right?
So the big thing I'm hearing isthis expectation thing?
I'm wondering, just as I makethat simple reflection, what's
coming up for you as I point outthis expectation component.
Nestor Solari (09:08):
Yeah, I think a lot of what we talk about as a
team at CEO is kind of settingexpectations with each other,
with ourselves, with our clients, their customers, and it's
funny and sometimes you kind ofdon't realize the expectations
you're setting for yourself.
But that resonates for me and Iguess what that takes me to is
(09:35):
well, if my expectations aren'tmet, it feels like I might
immediately start searching for,okay, what's the right formula
here, what's the right next step, or how do I get this back on
track when maybe it's not offtrack?
Yeah, that's kind of what cameup for me is kind of, what does
(09:57):
this look like if I go into itwithout expectations?
or with less expectations ormore flexible expectations.
Brian Wang (10:07):
Have you ever been in a conversation with somebody
where it felt like they werecoming into it with a whole
bunch of expectations of how itwas going to turn out?
Like they had an agenda withhow it was going to go.
Sure, yeah, how did that feelfor you.
Nestor Solari (10:28):
Off-putting is the first word that comes to
mind.
If I know someone comes to thecall with an agenda, you're kind
of on guard.
And I mean I guess especiallyin the checkwriter, check
receiver kind of founder,builder, investor type
(10:51):
relationship, it almost seemslike there's those preconceived
notions, the notion of an agendakind of baked in.
Brian Wang (11:01):
Right, yeah, there's some dance that we do some part
to play.
Nestor Solari (11:10):
But if we take it out of that context, kind of
being in a conversation withsomeone that seems to already
have an agenda or have a waythat they think they should go,
kind of puts me on the defensivea bit.
Brian Wang (11:22):
How do you start to feel toward that person in
particular in that moment?
Nestor Solari (11:26):
Well, you kind of almost get the sense that
they're trying to manipulate you, right?
I think that getting put inthat guard also, it's
antagonistic, almost right.
It's, yeah, you feel like youshould be putting pressure back,
(11:47):
almost, that you need to slowthis agenda down a bit or slow
this person down to make sureyou're not being taken advantage
of.
Brian Wang (11:58):
Yeah, so the word that came up for me was like
that feels adversarial.
Nestor Solari (12:04):
Yeah.
Brian Wang (12:05):
Right, you versus me .
Let's see who's going to win.
Yeah, so yeah, you've got tolook on your face.
For those who are justlistening to audio, they can't
see this, but I'm curious what'srunning through your mind and
your heart as this is processingthrough you.
Nestor Solari (12:25):
Well, I think the first thing that I'm thinking
about is kind of thisadversarial nature of these
conversations.
It really doesn't feel likethat is how it is with my
largest investors and with mostsuccessful founders and their
(12:47):
best kind of investorrelationships, and kind of
adversarial doesn't seem toquite accurately describe kind
of how the relationship shouldbe right.
Ideally we're both winning andthere's a couple scenarios where
one wins and the other oneloses.
But I think in the bestoutcomes the investors and the
(13:09):
founders kind of are both kindof aligned and trying to move in
the same direction, right, andso I wonder how it gets there
from here.
A bit is kind of what I wastrying to work through in my
mind and was putting that lookon my face.
Brian Wang (13:27):
Yeah, yeah, yeah, great.
So I think you're totally right.
Ultimately, when you're raisingmoney, you're looking for
partners.
You're looking for people whoare aligned with your vision,
they're excited about yourvision, they're going to support
you with capital and resourcesand all sorts of things.
To start that off from anadversarial frame feels like an
(13:51):
uphill battle, right, Because itbecomes like a you versus me
thing, and that's pretty faraway from hey, we're on the same
team, we're allies now, right.
So I guess the question that'scoming up for me now is, when
you find yourself in thosesituations, right, where it ends
up feeling a little adversarial, this is an open question.
(14:16):
But what is it that's drivingthat on your end?
Nestor Solari (14:24):
And I'm thinking about a couple of different
conversations and I'm thinkingabout, okay, when I felt this,
what memories this feelingbrings, but I think there are a
couple.
I think sometimes it might feellike it's triggered by I don't
(14:46):
know if it's a question or areaction to something I say,
which I think is the first onewhere I'll present something as
a truth or as my experience oras something as I know.
And then the person across thetable maybe the story I'm
(15:08):
telling myself is that they'rebeing cynical and disagreeing
with me, just to be kind of playdevil's advocate, possibly, and
I feel like that kind of setsus up to butt heads.
That feels like it might be themost common experience, the
most common story I have in myhead about when this happens.
Brian Wang (15:30):
Can you?
I'm wondering if you can maybeput yourself in a specific
situation where that happenedrecently, one where this kind of
feels real to you.
You don't need to name names,of course, Sure.
Nestor Solari (15:42):
You know, I think one that feels common, almost
like a recurring dream right now, is, I think, in the auto
insurance sector in general.
It's very competitive.
Some see it often as a kind ofcommodity product, whereas the
truth is it's quite nuanced andthere's a lot of variation in
(16:06):
auto insurance and the type ofcoverage, and I think that's
something I've learned throughmy experience and working with
immigrant communities andselling lower coverage limits
versus maybe what I'm used tobuying from Geico, and so a lot
of times when I try tocommunicate that nuance or that
(16:27):
difference, I think I sense, orthe story I tell myself about
how others react, is that theydon't believe me.
They believe that these largecompetitors will easily put us
out of the business once weprove that we can do this
(16:49):
profitably or whatever it is,and that seems to be something
that I've practiced a lot sinceearly days in trying to explain
the nuance and speak around, butstill something that feels like
it's a challenge to get aninvestor to digest, especially
if they're learning about thissegment for the first time.
Brian Wang (17:12):
Okay, so you've got this experience where you've
gleaned some important, nuancedinsights about this market.
And then you go into thesemeetings and you say, hey,
here's something reallyinteresting that we've learned,
that we've learned that weunderstand a certain truth about
the space that we're working in.
We'd like to share it with you.
And then the response is almostit sounds like there's a
(17:39):
dismissal, there's a yeah, but Ithink you guys are going to get
crushed and I want to see if wecan maybe then take that moment
that I'm describing and zoom ina little bit into your
experience here.
So in the moment where you,where that resistance comes up
now here's why that's not goingto work, et cetera, right, what
(18:02):
do you notice?
You start to feel in yourinternal reaction there.
Nestor Solari (18:08):
Get defensive.
Almost feels like I lean in andput my shoulder down a bit.
It feels a certain tightness inmy, in my shoulders and chest
Feels like my, my almost kneejerk or immediate response is to
(18:29):
start trying to spit out thedozen reasons why I quote
unquote.
No, they're wrong.
Brian Wang (18:38):
Okay, so there's a defensiveness, your body starts
to shift.
It's like it's almost like it'skind of like almost collapsing
a little bit.
If I heard that correctly,there's a little bit of a
curling, there's a, there's aneed to defend something we
could spend some time namingthat but you're, you're now,
you're on the defense, and thenalso like but wait, let me
(19:01):
explain why you're wrong, right,which then sounds like it's
like a little bit of this now isback and forth, right, and so,
if you can just stay in thatspace for a moment, that
defensiveness, connect with thatdefensiveness now.
Now I want to ask, underneaththat, what are you starting to
believe about yourself and whatare you starting to believe
about that person in thatsituation?
Nestor Solari (19:22):
So, like there, this is maybe a little mix
between what I believe and theybelieve, or maybe what I believe
about what they believe.
Sure, yeah.
Brian Wang (19:30):
Yeah, what you're projecting onto them, sure.
Nestor Solari (19:32):
Yeah, exactly, I think there is.
Well, I must not be credible asa founder if they don't believe
what I'm saying to them, orthis investor is not
sophisticated or is not or isintentionally offensive.
I'm not intentionallyobfuscating my point because
(19:59):
they have some bias against whatme or what I'm doing.
The other one that comes up iskind of almost kind of a need or
a or it feels like a thirst toprove myself right.
If this person doesn't believeme, then that means I'm wrong,
whereas that, saying that outloud, all of us like.
(20:24):
Well, I don't need them tobelieve me for me to believe me,
to believe myself and know thatthis is my truth or my
experience.
Brian Wang (20:32):
Yeah, I know you get that on an intellectual level.
Nestor Solari (20:37):
That's the challenge.
Brian Wang (20:38):
Yeah, but it sounds like, just to paraphrase, if
this person you see this datapoint this person doesn't seem
to believe me.
And now this must meansomething about me.
I'm not credible, I'm notbelievable.
I must be wrong here.
And I just want to slow downand notice just let us both
(21:03):
notice how you jump from thisperson.
It doesn't get what I'm sayingor disagrees, and then the
conclusion jumps right to oh,that must mean something about
me, that must mean somethingabout my own competence or
credibility.
And then the move to defendoneself, to prove oneself.
Nestor Solari (21:28):
So what that makes me think about is well, if
I were competent and credible,then why wouldn't they believe,
right?
And then I guess there's well,there's a step between me being
competent and credible andseeming, in another person's
eyes, to be competent, credible.
Those are two different things.
And then there's also the well,whether it seems or I am,
(21:59):
there's other reasons why theymay not believe something,
despite my competence andcredibility.
Brian Wang (22:06):
Sure, yeah, I can see you jump into the
alternative reasons.
Absolutely.
What I hear is that there's anexperience that you have about
around this feeling of, oh, I'mnot credible, I need to prove
myself.
Where has he felt that?
Does that feel familiar to you,even outside of this context?
Nestor Solari (22:25):
Reminds me of interview processes throughout
my career before being a founder, Interviewing and not getting
the job that feels that's astrong feeling.
Brian Wang (22:39):
Yeah, what's the feeling if you were to name it?
Nestor Solari (22:46):
Is it inadequacies?
I think is.
The thing is well, I know I cando this job and I'm trying to
communicate that but I can't, soI'm inadequate in some form and
then I don't get the job.
Brian Wang (22:57):
So that confirms that, this inadequacy- when did
you first get that message Insome sense that you're
inadequate?
Nestor Solari (23:07):
Going back failing tests.
I can't remember necessarilygetting an F on a test ever, but
I do remember not getting theA's that I expected to or wanted
to.
Let me see if there's somethingfurther back.
I can even kind of maybe likefriend groups as a kid.
(23:32):
It feels like that's as likeyou're kind of embarrassed in
school for whatever reason and Ican't can't come up with a
specific example but you thinkabout like yeah, you know, we
almost feel similarly to theinterview.
It feels like when you're a kidand you tell the the, the girl
(23:52):
you like, that you like them andthere's no reciprocation there,
right?
It almost feels like well, by bydefault.
A lot of the the investorconversations feel like it's
almost like an opt-in by thefounder and then it's up to the
investor to make the decision,until that's the point that that
(24:16):
power dynamic shifts right.
Brian Wang (24:20):
Right, it feels like there's this person has power
over you.
I need to get their approval, Ineed to win their approval.
And then, when you don't getthat, it feels like that.
There's that feeling ofinadequacy.
I didn't, I didn't win theapproval because I'm somehow
inadequate.
And when you're, when you're inthat, in the middle of that
(24:42):
feeling, live, what's the?
What's the urge, right, what'sthe, what's the thing that your,
your system is like justspringing to want to do, then
Feeling frustration, feelinggritting, grinding my teeth,
(25:03):
maybe sadness, tears even.
Nestor Solari (25:07):
It's just kind of like above level of frustration
.
Brian Wang (25:12):
Yeah, I wonder if you can connect with that a
little bit, the cherry feeling,the sadness, and what's that
bringing up for you.
Nestor Solari (25:28):
Whenever that sadness comes to mind and I
don't know if it's I'm feelingbad about myself or I feel like
I'm being a little too mean tomyself I think one thing from
previous coaching I think Ithink of myself as a little kid
(25:50):
with those emotions.
Sure, it's just feeling thatcompassion, that's kind of what.
Those feeling, that emotion andfeeling that I may be exposing
myself to or kind of, or kind ofputting myself in that, in that
(26:11):
headspace or that position.
It feels almost like I'm notshaming myself, I'm punishing
myself, and then that kind ofmakes me step off and be like,
well, chill out, man.
Sure, don't be so hard onyourself.
A little bit is the.
(26:32):
Thing that comes to mind.
Brian Wang (26:34):
Yeah, so you just walked us through a kind of a
series of steps here.
Right, the way you start torelate to yourself or different
parts of yourself, but I don'twant us to necessarily skip over
the part where you feel thatfrustration and sadness.
I think I hear that it's likeokay, don't be so hard on
(26:55):
yourself.
Yeah.
Nestor Solari (26:57):
I think one thing that's triggered there is.
Well, I don't want to be toohard on myself because I don't
want to feel this.
Brian Wang (27:07):
Feel what exactly.
Nestor Solari (27:09):
Feel this kind of frustration, or this sadness,
or this gritting my teeth, kindof fighting, crying, kind of
feeling.
Brian Wang (27:19):
What I hear in that is there's like I'm gritting my
teeth hard to hold back fromsomething.
It's like you're clenching sothat, so as to not feel
something under that.
What's that?
Nestor Solari (27:33):
Almost and maybe it's that sadness or that.
Yeah, it's funny that just thatreaction to not let yourself
feel this, so anythingunpleasant seems like your first
.
My first reaction is let me tryto do something or say
(27:56):
something to not let myself feelthat.
Brian Wang (28:01):
I think you're doing it right now.
Nestor Solari (28:02):
Yeah.
Brian Wang (28:03):
Yeah, what happens if you just allow any of that in
for a moment?
Nestor Solari (28:11):
I feel lighter.
Brian Wang (28:16):
You might ask this part of yourself that feels sad.
What does it want you to know?
Nestor Solari (28:23):
I don't know if this is just the reaction to not
feeling it, but maybe kind ofdon't be hard on yourself, don't
be so hard on yourself, don'tinflict this.
Brian Wang (28:42):
Because you're sad about how hard you are on
yourself.
Nestor Solari (28:47):
Maybe, or that I'm sad because I'm being hard
on myself for not achieving whatI expected to achieve in that
moment, and so I tell myselfthat I'm not good enough or that
I'm not performing as well as Ishould be and that makes me sad
(29:07):
.
But then, kind of exploringthat sadness, it's like, well,
maybe you need to reevaluatethat reaction, right, reevaluate
that it's not the lowerstandard.
I think that it starts gettingreally cloudy when you think
about kind of keeping mystandards high and working hard
(29:29):
and making myself kind ofoutperform versus this kind of
maybe extreme, like hard lyingstance of anything not going my
way is immediately my fault.
That needs to be corrected.
Brian Wang (29:51):
Well, there's a world where you can have a lot
of high standards and reallyseek to achieve without really
ripping into yourself when youdon't actually succeed in some
of those things.
If I'm tracking you, there'ssome party that feels sad that
(30:12):
you're not hitting some of thoseoutcomes.
Is that?
Nestor Solari (30:16):
accurate.
I think that's right yeah.
Brian Wang (30:18):
Okay, yeah, yeah.
What's wrong with feeling sadabout those things?
Nestor Solari (30:28):
I smile because I think this is that fear, pain,
sad avoidance oftentimes createsa lot of these challenges and
just not being willing to feelsomething in a moment or sit
with something in a moment.
So I start reacting and kind ofgo on autopilot a bit.
Brian Wang (30:55):
What I hear is that the disappointment and the
sadness in that moment where youdon't meet the expectation,
feels so bad that you resist it,and then that resistance
creates the knee-jerk reaction.
I have to defend myself now.
I have to prove myself now.
Yeah, does that land?
Nestor Solari (31:21):
It does Just always, kind of coming back to
this, a lot of the unwantedbehaviors that we work through
together, I think, stem fromavoiding a feeling or kind of
(31:41):
maybe escaping thatconsciousness almost Sure, and
hey, I don't want to sit withthis because it's uncomfortable
or it doesn't feel nice.
Brian Wang (31:52):
Yeah.
Nestor Solari (31:54):
But not that what you do to avoid that feels too
much better, right.
Brian Wang (31:58):
Sure, but it's familiar.
Nestor Solari (32:02):
Yeah, yeah, yeah.
Brian Wang (32:05):
So let's play with this.
How might these situationschange, these conversations,
these interactions withinvestors change, if you didn't
fight yourself so hard Like?
Fight that sad reaction, fightthe disappointment, instead of
just allow yourself to have that?
Nestor Solari (32:25):
It feels like they would slow down a bit,
which might play to my favor tobe able to clearly communicate
what the point I want to getthrough and maybe owning that
conversation a little more.
But the first thing that reallycame to mind was right now it
feels like these become a bit ofa chain of events where it kind
(32:50):
of keeps compounding and justkind of like running through and
pushing through and just doingwhat you're feeling or want to
do and through and then hopingit kind of comes out on the
other end versus works out onthe at the end of like all,
versus almost handling thesemore on a conversation per
(33:11):
conversation basis and maybeunblinking them.
Brian Wang (33:16):
It's like you go on autopilot through the rest of
your conversations, almost likesomething takes, something takes
over, and you're like what Igot to?
Just kind of like power throughthese.
Now, right, I would imaginethat that would leave you
feeling probably less connectedto not just yourself but also to
the person that you're talkingto.
Nestor Solari (33:39):
Exhausted thinking about it.
Yeah, just have these kind ofback to back to back phone call
days and that's just not givingyourself that space or that room
to breathe and reflect and sitwith yourself for a moment.
Brian Wang (34:01):
What comes up for me is the word presence.
When we enter into thatautopilot state, often because
there's some feeling that wereally don't want to be with, we
lose presence with ourselvesand we certainly lose presence
with the people that we're with.
Those conversations lose a lotof their dynamic potential.
(34:26):
Very, very hard for us to dancein the moment with whatever's
coming up, because our agenda isjust to move on through there.
Let's get to the thing here.
We all experience that when welose presence and that starts
with ourselves we lose presenceand then everyone else around us
(34:48):
can feel that.
Nestor Solari (34:51):
It's funny, one of our values at CGO is to be
engaged and I think it'sprecisely speaks to kind of
being present with each otherand making that time together
valuable by being there witheach other.
I think a lot of times it's inthe kind of especially in the
(35:12):
virtual world and the phonecalls it kind of feels like
you're kind of alone, eventhough you're on kind of the
other side with somebody, andeven not being engaged with
yourself by yourself.
Like avoiding those feelingsseems like it's almost like a
(35:34):
kind of self perpetuating kindof vicious cycle.
Brian Wang (35:40):
Oh sure, yeah, we're constantly inviting others to
engage in certain behaviors.
We model so much of thebehavior that then occurs around
us.
I want to ask you what are youseeing at the moment?
That wasn't so clear when westarted.
Nestor Solari (36:00):
A couple of things come up for me.
I think one is maybe thinkingabout the triggers here and
thinking about different ways tomaybe recognize when I'm in
that triggered state and whetherit's taking a breath or taking
a moment and kind of thinkingabout, okay, how can I come out
(36:22):
of it.
But I think kind of going intothat triggered state is
something that I feel that I'vehad it really appreciated.
I felt, okay, I'm going intothis level headed and I'm
approaching this and our streetfolks are going forward fashion,
but the outcome is what'sweighing on me, whereas it's
(36:47):
obviously feels a bit morecomplex, in that it's not just
the, it's not really the outcomethat's weighing on me, it's the
whole process and kind of addsup.
So I think if I at thebeginning of this I probably
would have said the outcomes ofthese conversations are weighing
down on me, because now itfeels like maybe, well, my
reaction to others, reactionskind of take me out of being
(37:12):
present, which leads me downthis, this kind of maybe dark
alley and so, whereas before Imay have been more prone to
accept, well, like this is justwhat happens when I have a bad
conversation, maybe say, well,was that a bad conversation.
(37:35):
Really, it's okay if it was abad conversation and it's okay
if I feel bad about whateverhappened, but that doesn't
translate to all theseconversations having to be bad.
It doesn't translate to mycredibility or my confidence or
(37:57):
my conviction in what I'm doing.
Brian Wang (38:00):
I don't have to translate into this adversarial
thing.
Now I have to really provemyself.
Nestor Solari (38:07):
Yeah, what if I was okay, not knowing exactly
what they thought?
And even if I knew what theythought, what if I was okay with
it, even if it wasn't what Ithink?
Brian Wang (38:20):
I'll simplify that for you.
What if I was just okay?
Nestor Solari (38:26):
Sounds tough.
What if I was just okay?
Brian Wang (38:35):
That, by the way, also includes whatever the
emotional state is.
What if my sadness was okay?
What if my disappointment wasokay?
Nestor Solari (38:57):
What's coming for me is thinking about okay if my
disappointment or my sadness isokay, yet still want to use
those as tools.
Right, you kind of use sadnessto push towards happiness or you
use disappointment to pushtowards success or
accomplishment.
Feels like the toolkit thatI've long used.
(39:18):
Maybe it isn't necessarily aseffective of a toolkit anymore.
Brian Wang (39:27):
What you just said was let me go take this emotion
and change it or fix it orsomething.
Versus what if it was just okayfor me to be sad right now and
then, if I just allow myself tofeel that eventually it'll move
through me and then I can moveon.
Nestor Solari (39:47):
Yeah, you kind of look at, I think happy inside
is a good, a good way to playwith, right, because you almost
think, okay, if I'm feeling sadand I don't do anything about it
, then I might never be happy,right, okay, if you're sad and
(40:08):
it goes through you, you canalso be happy in the future, and
it doesn't necessarily have tobe a result of you forcing your
sadness away, right.
Brian Wang (40:19):
Yeah, emotions are kind of funny.
That impulse is, oh I'm feelingthis feeling, I'd better go fix
it.
And in my experience that's notreally how emotions work.
They're not there to be doneaway with or to be treated as a
problem.
They might point to certainthings that matter to us.
(40:41):
They point to needs and help usmove toward the things that we
need and that we value.
But when we treat them asproblems inherently, that's
where all of the avoidancebehaviors start to come in, or
the numbing behaviors start tocome in, or the defensive
behaviors start to come in,right.
(41:02):
But if we knew that, thefeeling itself, that's okay, let
me have it, let me see whatit's about.
We'll commit maybe and we startto shift the way that we relate
to it, and then all theavoidance stuff doesn't become
necessary anymore.
Nestor Solari (41:25):
And the avoided stuff is where the problem lies,
right.
Brian Wang (41:30):
No, that's up for you to decide.
Nestor Solari (41:33):
I'll make sure I'm okay with my feelings.
Brian Wang (41:38):
Let me just check in with you as we start to wrap
here.
So take a step back.
Kind of covered a lot here.
What would it look like for youjust to move this forward a
little bit?
Take this forward.
Nestor Solari (41:51):
I guess the one thing that I'd take away from
here it's okay to feel myfeelings and let's kind of
practice doing that, so kind ofsome sort of maybe mindfulness
practice or some kind of justsome checking in with myself on
my feelings and my reactions Ithink is what I need to do and
(42:17):
kind of maybe be moreintentional about it.
I think this space, thiscoaching space, is always very
helpful to slow down and thinkabout these things, and I think
I need to be more consciousabout working this into my
personal toolkit, because itfeels like we were able to just
(42:39):
kind of unpack something andkind of bring it to this core
issue of avoiding this feeling,and I think that the key thing
is working on not avoiding thefeeling.
Brian Wang (42:57):
Yeah, and just to build on top of that, there is
this, the fundamental checkingin.
Can I check in and see whatemotions are present here,
what's wanting my attention,what wants to be felt here?
And I like to use the wordwelcome, can I welcome this that
(43:18):
there's an activeness to thatright Rather than it's like I'm
not going to resist there's awelcoming and then see what
happens there.
Nestor Solari (43:24):
You know what else comes up for me when you
say welcoming kind of evenhonoring kind of the evolution
of the human brain, the factthat those feelings are there
for a reason that would sufferall of us to maybe comprehend,
(43:47):
but being okay with it and kindof sitting with it and exploring
it and appreciating it.
Brian Wang (43:56):
That feels like a good note to end on.
Nestor Solari (44:00):
Thank you as always, Brian.
Brian Wang (44:02):
Most people know that raising money requires you
to tell a great story, but italso requires you to connect
with the investor on the otherside.
That's really hard to do whenyou get thrown off during the
meeting.
Make no mistake, savvyinvestors will push back and ask
questions.
It's part of their job.
In Nestor's case, when he gotpushed back, he internalized it
as inadequacy and rejection, aswell as feelings of sadness and
(44:24):
frustration.
All of these are perfectlynormal reactions.
The trouble comes when we clampdown on those emotions and then
we get really rigid in themeeting and then we start to
bring an unproductive energy tothe rest of that conversation as
well as subsequent meetings Inour session.
Once Nestor allowed himself tofeel his own sadness, it started
to get lighter for him.
His feelings had less weightand his stories had less grip on
(44:46):
him.
The welcoming of his innerexperience led to more freedom
and resourcefulness for him.
As the saying goes, what youresist persists.
Fundraising is a full contactsport.
You have to be willing to fullyembrace the experience,
emotions and all.
So if you are or are about togo fundraising, ask yourself if
you're willing to fully embracethe experience and if you're not
(45:08):
, ask yourself what you wouldrequire in order to do so.
Thank you for listening.
To Slow Down, to Speed Up.
If you enjoyed this episode,please rate it in your favorite
podcasting app, and if you're afounder looking to get to the
next level through coaching orcome on the show, please contact
me at dashingleadershipcom.
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