Episode Transcript
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emily-sander_1_05-08-2025_ (00:25):
Remy
Guarini is on our show today.
Welcome all the way from NewYork City.
remi-guarini_1_05-08-2025_1 (00:30):
you
for having me.
I'm, I'm really excited to bechatting.
emily-sander_1_05-08-2025_1 (00:32):
I'm
looking forward to this one.
So you are a three time chief ofstaff, so can you just give us
an overview of how you gotyourself into the chief of staff
role three times.
remi-guarini_1_05-08-2025 (00:44):
Yeah,
so.
I would say I've been a chief ofstaff, as you said, three times
in really different contexts.
Um, just to give a bit ofbackground, so first I was, um,
the chief of staff at Bayes onKitney, which is a Facia brand,
music label and hospitalitybrand.
then I was the chief of staff atCapital Factory, which is a.
(01:06):
More established VC firm andstartup incubator in Austin,
Texas with other Texas locationstoo.
And then I was at Neon, a soloGP early stage VC fund where I
was the first hire.
And then I recently stepped intoa VP of operations role.
But in terms of kind of likegetting into the roles, getting
(01:27):
into my first role, I wasactually.
Introduced to the CEO of Mathrough his wife, um, who I
worked with at Madewell at thetime.
Um, I had met him once before,like we had gone out to dinner
together.
Um.
Really, he, he took a chance onme in, in hiring me.
(01:50):
I hadn't ever been in a likechief of staff role.
I, I actually really didn't knowanything about the role prior to
that, but really I was likesuper hungry for responsibility.
I wanted something I could growinto really quickly.
The idea of working with the CEOacross all aspects of the
business was really exciting andappealing to me, and I knew that
it was gonna be demanding, like.
(02:11):
It was a hundred hour weeks.
I probably made like$5 an hourif you broke down
emily-sander_1_05-08-2025_ (02:15):
Wow.
remi-guarini_1_05-08-2025_16 (02:16):
to
hourly.
But I also knew I'd be doing alot of things for the first time
without any roadmap, and thatjust really excited me, the
learning potential and, um, itreally changed my trajectory, of
my career and, and kind of ledme into my next roles.
emily-sander_1_05-08-2025_ (02:32):
It's
so funny, like all the chiefs of
staff I've had on, it's theconnection.
It's the, I knew his wife, wewent out to dinner, knew him
socially and then.
Boom, and then it opened up allthese doors.
So it really is who you knowsometimes, and it's, it's the
person you least expect at timesas well.
So, um,
remi-guarini_1_05-08-20 (02:49):
hundred
percent.
emily-sander_1_05-08-20 (02:50):
gotcha.
How, so how did your, how didyour chief of staff roles build
on each other?
You kind of alluded to it there,but what was the, what was the
next piece in the puzzle?
remi-guarini_1_05-08-2025 (02:59):
Yeah,
so I think like at kids a.
Well, I would say like, I feellike every chief of Saff roles
kind of like getting like anMBA, but paid and, and without
having to take the time off.
But you get to get this likereally incredible typically
like, yeah, like 1, 2, 3 yearexperience.
Um, and each role has taught medefinitely something really
different.
(03:19):
Um, I think like at Pit A one Ireally like.
Build up my ops like chops.
It was a fashion brand, like firfirst and foremost, but also
hospitality and like, so I didreally every aspect of
operations from, you know, HRand people operations to, um,
(03:41):
manufacturing and production andlogistics on the fashion side
emily-sander_1_05-08-2025_ (03:45):
Were
you learning all this on the
fly?
Like, did you know any of thisbefore?
remi-guarini_1_05-08-2025_160 (03:49):
I
knew some of the fashion, like
kind of logistics and like howlong it took for certain things
to happen because I'd been adesign like operations
emily-sander_1_05-08-2025 (03:58):
Okay.
remi-guarini_1_05-08-2025_ (03:58):
kind
of coordinator at Madewell
before, but a lot of it wasquite new.
Um, and I will say likefashion's one of the most
complex businesses from an opsperspective, so it was a really
great way to like dig in and getexperience across all of that,
like in p and l management andeverything.
And I think.
That's something that I reallylike learned there.
(04:19):
and then I think, you know.
I at Capital Factory, it waswithout like network building
and visibility.
The CEO was more seasoned.
I had to manage up, they wouldnavigate kind of internal
politics and be really outwardfacing with super high profile
stakeholders, which was reallyuncomfortable to me, especially
at the time.
Like I'm, I'm more shy and Idon't like to be at the
(04:41):
forefront, but it kind of likeforced me in into that.
Um, so I kind of built up thatskillset alongside the op skill
set, and also got a one-on-oneand like all things venture
capital through that role.
Um, and then I'd say that likeneon kind of like brought all of
it together.
You know, I couldn't have likedone the zero to one without
having.
(05:02):
I've done, you know, a lot ofthings across all operations
before and working with a, a lotof different people and, and
really like high kind of levelof people internally out to
externally before.
And so I think like the firsttwo definitely prepared me for
this one.
And also the first two taught methat I really wanted to be a fa,
like I wanna be a founder oneday.
(05:22):
I wanna build something on myown.
And Neon was this opportunity tolike that zero to one
experience.
Build something but not have totake on the risk.
You know, I got paid a salarythe whole time.
I've, you know, it's not my nameon the firm, it's, it's my gp
Kimmy's.
But still getting to get allthat like frontline everything.
Experience from, from day one,
emily-sander_1_05-08-2025_1 (05:42):
You
get a front row seat.
Yeah, you get a front row seatto it all.
I wanna highlight something yousaid, which is you felt
uncomfortable going in with likeall these senior people, and
thank you for sharing thatbecause I know chiefs of staff
that I speak with one-on-one.
Most of them have thatexperience yet a lot of people
think they're supposed to kindof front in this way.
Like, I can take on the worldand I'm not scared of anything.
(06:02):
I remember walking into my firstboard meeting, I was like
sweating and I was like, oh mygosh.
Like this is like, I'm just alittle old me and these are very
professional, very seniorseason.
Like everyone knows what they'retalking about.
Um, so I appreciate you sharingthat and the fact that it seems
like it translated into.
I grew from that.
I learned how to be in thesesituations.
(06:23):
Now I know about VC stuff, nowI'm in these conversations with
the front row seat.
So I just wanted to highlightthat for listeners because I
know that goes through people'sminds.
remi-guarini_1_05-08-2025 (06:31):
Yeah,
definitely.
It's good to do things thatscare the crap outta you.
emily-sander_1_05-08-2025_ (06:36):
Yes.
So you mentioned, um, your gp,Kimmy Scott.
Can you tell us a little bitabout her and how long you've
been working with her and all ofthose, all of those good things.
remi-guarini_1_05-08-2025 (06:44):
Yeah,
so she's incredible.
Um, we've been working togethernow two years of, like two
months.
Um, and so it's, it's been alittle while, but we actually
met about a year and a halfbefore I started at Neon.
Um, I was at Capital Factory atthe time.
I met her through my now husbandactually, which
emily-sander_1_05-08-2025_1 (07:04):
Ah.
remi-guarini_1_05-08-2025_16 (07:05):
of
funny.
Um, yeah.
Which I'm like, I always loveto, to bring him into the mix.
But, um.
I, I was at Capital Factory.
I really wanted to connect withlike a woman in vc, but also
somebody that like came fromkind of a non-traditional
background.
Like I didn't come from banking,pe, like anything like that,
consulting into vc.
(07:25):
I came through fashion that'svery odd.
And so I really wanted to liketalk to someone that maybe also
had that kind of, uh, backgroundthat was a bit unique and.
My Ashcon, my husband was like,you have to meet Kimmy.
She was a founding partner, soshe co-founded the firm eight VC
Life sciences, a technology firmwith Joe Lonsdale and a number
of other partners.
But she, you know, started herfirst company, a jewelry
(07:48):
company.
When she was 15, she went to theFashion Institute of Technology
for college, and then she movedinto, uh, incubating and, and,
and investing.
Um, and so like when we talked,we instantly clicked and it was
just like a relationshipbuilding combo, but I was like.
She was wearing a, a, a dresslike from Hill House Home,
that's current, that's what Iwear right now.
(08:09):
But I love the brand.
We were like, you know, geekingout over that and then really
just like shared kind of likevalues, ambition, nontraditional
past, and I just respected also,like she has this sense of being
really bold, really smart.
Curious, but also, and serious,but fun.
Like she enjoys it.
And, and that's something that Ikind of aspire to out of my like
(08:30):
career and, and roles is to likebe really excited and, and have
work, be fun, even if it's alsoserious.
And so kind of how we met.
Um, and then I reached out toher about a year later, so I
guess I've known her fortechnically like four-ish years
or, or so.
Um, and.
(08:52):
I really feel like a mentorship.
Hey, I'm, I'm leaving, you know,Austin, I'm leaving Capital
Factory at Boogie Bat to NewYork.
I, I wanna do something zero toone.
What do you think?
and it just so happened that shewas actually about rolling out
of eight VC to spin out theinvestment practice She built
there and, and watch her ownfirm.
(09:12):
And we spent a bunch of timetogether and, and then we're
kinda like, Hey, let's, let'sjump in and, and do this
together.
She knew she needed like aoperational right hand and.
We fit.
So that's kind of, that's how I,I joined and have been there
ever since.
emily-sander_1_05-08-2025_ (09:25):
Wow.
Now, how had she had a chief ofstaff before or was this her
first one?
remi-guarini_1_05-08-2025_1 (09:30):
She
had had a chief of staff at
eight VC and actually like, Ithink two one though she had for
like years, who after about twoyears transitioned to more of an
investor role, but still work tolike really close with her,
which I think is like soimportant.
Uh, it's really great to nothave to like break it exec
emily-sander_1_05-08-2025_ (09:49):
Yes.
remi-guarini_1_05-08-2025_ (09:49):
what
a chief of staff is.
Yeah.
emily-sander_1_05-08-2025_1 (09:51):
She
knew what she, she knew what she
wanted and she was like, I wantyou for that role.
That's awesome.
Okay, so, um, and then youmentioned investor, so you're in
a dual role.
You've got chief of staff hatand then investor hat.
Can you talk about how youapproach those, those two roles?
remi-guarini_1_05-08-2025_16 (10:06):
So
I think like on, you know, the
ops side I've, I've built andthen I manage all of the firm
operations at Neon and that, andthat really sits with, it sits
with me.
and that's kind of a range of,of different things from, you
know, I.
Everything with like the ven taxaudit, you know, every kind of
vendor that you, that you chooseto, to onboard, to launch a
(10:30):
fund, but even like businesstools, things like that, to like
managing the budget and that,and actually managing the audit
and the quarterly closes andthere's a lot of financial like
work that goes into fundmanagement.
And so, um, it's all of that,but it's also like firm
building.
And hiring and, you know, ourvalues and who we are and how we
(10:52):
show up.
and our main business line isventure investing.
Right.
It's, it's working, it'sinvesting in early stage
companies.
It's, it's partnering with LPsand, and getting into great
deals and generating returns andreally like each inform each
other.
Right.
The investing work is, is thestrategy in what we do, but the
(11:13):
operational work needs to be setup and strong for us to execute
on the, that investing work andbeing able to kind of like have
my hand in both, I actuallythink informs each other, makes
me better as an investor, makesme better as an operator because
I know the firm level goals, um,when I'm talking with companies
(11:34):
or digging into the portfolio.
Um.
on the other side, I knowoperationally what's coming, oh,
we have to send a wire next week'cause we're about to close on a
deal.
You know, it kind of shortensthe communication timeline, but
I would say it's a lot of like,definitely multitasking and kind
of wearing different hats andbeing able to context switch a
lot.
Neither you like that or youdon't.
I happen to, to like that and itenergizes me and so I've, I've
(11:57):
found that it's something that Ienjoy doing.
emily-sander_1_05-08-2025_130 (12:00):
I
think that's important to know
because for some people it wouldlike drive them insane and I'd
be like, I'm burnt out becausethis is like frazzling my wires.
But for a lot of people it'senergizing and it's not a good
or bad thing to, to do that ornot, but you have to know that
I.
Is I hear people going for achief of staff role and they're
like, I kind of like things tobe like stable and predictable.
I'm like, mm, no, not for you.
(12:21):
Go go a different direction.
But, um, I think it's,
remi-guarini_1_05-08-2025 (12:24):
else?
emily-sander_1_05-08-2025 (12:25):
yeah,
go ahead.
remi-guarini_1_05-08-2025_1 (12:26):
No,
no, no.
I'm just saying like anythingelse if you want stable,
emily-sander_1_05-08-2025 (12:29):
Yeah.
Yeah.
Not, not, uh, one thing I'll sayfor chiefs of staff, never
boring, you're never bored.
You have, you have variety allthe time.
And it's interesting.
For you, it sounds like you'redoing like the LP kind of
fundraising and partnerships andall of those different rounds,
and you're also doing the PortCos.
So in those, I'm assuming have,you know, different rounds and
(12:49):
things to them.
So you're doing both ends of theequation there.
remi-guarini_1_05-08-20 (12:54):
Mm-hmm.
emily-sander_1_05-08-2025_ (12:55):
Wow.
Would you say like it's 50 50 oris it just kind of like, it just
depends on what the need is orhow does that go?
remi-guarini_1_05-08-2025 (13:02):
Yeah,
that's a great question.
I mean like, I think that myanswer depends on the week,
honestly.
Like some weeks are like, wejust got through our audit,
right?
Our first ever audit.
Great.
Like so glad that's done.
But like that meant that for atime I was.
Pretty focused on operationsbecause our audit
emily-sander_1_05-08-2025 (13:18):
yeah.
remi-guarini_1_05-08-2025_ (13:19):
time
as a quarterly, like close that
we have to send out to LPs, youknow, at the same time as, as
some other kind of like LP work.
So that was like a lot of likeops heavy lp, like communication
heavy work.
Uh, but then there's times when.
You know, we're working on alive deal and we need to move
really quickly so we don't loseit.
(13:40):
Or our portfolio company needssupport on something and, you
know, I'm, I'm jumping in anddoing that.
So I think it, the, thepriorities really change week to
week.
But I would say generallyspeaking right now it's about,
it's about 50 50.
Um.
emily-sander_1_05-08-2025 (13:54):
Okay,
remi-guarini_1_05-08-2025_16 (13:55):
It
started out more focused on the
ops and the fundraising stuff asthe firm was getting
emily-sander_1_05-08-2025 (14:01):
sure.
remi-guarini_1_05-08-2025 (14:02):
we've
raised a bunch of money and the
structures set up, um, it's kindof shifted a bit.
emily-sander_1_05-08-2025_1 (14:07):
And
then whatever you're, you're
comfortable and willing to say,where does Kimmy spend most of
her time?
remi-guarini_1_05-08-2025 (14:12):
Yeah,
so Kimmy's the GT the firm, and
so big role of hers isfundraising.
She's the front facing person.
Um, you know, taking every,like, fundraising, uh, meeting
and,
emily-sander_1_05-08-2025 (14:23):
Yeah.
remi-guarini_1_05-08-2025_ (14:23):
like
being that relationship manager
on the front facing side, um,which is a ton of.
in itself is, is a lot of workand, and, and gps are kind of
always fundraising.
Even if you've closed your fund,you're,
emily-sander_1_05-08-2025 (14:35):
Yeah.
remi-guarini_1_05-08-2025_16 (14:36):
of
never, not fundraising.
Um, and so that has been areally big focus for her.
Um, as well as obviously she's agp, so anything deal related,
she's the ultimate decisionmaker.
and so she's getting pulled inas we're doing diligence and,
and creating relationships withfounders.
And then she holds also all theboard seats, um, you know, for
(14:58):
portfolio companies.
And she's a, because she's anoperator and has started a bunch
of companies, she's veryoperationally inclined.
And so she digs in withportfolio companies, I would say
like likely a lot more thanmaybe what you would see.
Um.
You know, kind of across themarket.
Um, and so that's, I feel likethose three things where she
spends her time and then ofcourse, you know, hiring and,
(15:21):
and meeting candidates and, andlike the firm building things as
well, that, that's something wepartner on together.
emily-sander_1_05-08-2025 (15:27):
Yeah.
Very cool.
Let me take one step back.
Just uh.
We're throwing out acronyms andI'm, I'm aware that some people
might not know what we'retalking about.
Um, so LPs are limited partnersand in like a very nutshell,
they fund the VC firm.
And then the VC firm will makeinvestments to, uh, nascent
companies and hopefully thatthey grow.
So just like think of threelayers, LPs, vc, and then the
(15:48):
portfolio companies calledPortco.
So if you're like listening andyou're lost, hopefully that
helps you, um, drive this.
But what Remy is saying, sheworks on both the LP side.
And the port coast side, whichhappens in some cases and not
others.
And then it sounds like your gp,your principal, Kimmy, is very,
um, very involved in both sidesas well.
Obviously fundraising throughthe different rounds of LPs, and
(16:09):
then also being involved in thedue diligence for the port
coast.
Did I have that right?
remi-guarini_1_05-08-2025_ (16:14):
Yes,
emily-sander_1_05-08-2025_ (16:14):
Here
we go.
remi-guarini_1_05-08-2025_1 (16:15):
And
also like really like there's a
lot of similarities with whatshe does and what a CEO does.
Like think very commercial, youknow, driving and winning
business.
emily-sander_1_05-08-2025 (16:24):
Yeah.
remi-guarini_1_05-08-20 (16:25):
there's
a lot of overlap there.
emily-sander_1_05-08-2025_13 (16:26):
So
you and I were talking about
this earlier, but I've seen VCfirms and some PE firms
honestly,
remi-guarini_1_05-08-2025 (16:31):
yeah.
emily-sander_1_05-08-2025_1 (16:31):
um,
have, uh, chief of staff as an
operating partner at the firmlevel.
So sometimes they're chief ofstaffing for the PE firm or for
the VC firm, and then sometimesthey have them.
I.
Deployed into their Port cos,and I've seen this where you're
doing a hundred percent of yourtime in this one portfolio
company for like 18 months.
And then I've seen it also whereyou're gonna do fractional work
(16:53):
for maybe three or four of ourportfolio companies.
And I was wondering like, haveyou seen this, have you thought
about this?
What are, what's your, what areyour thoughts on, on how VC
firms use chiefs of staff?
remi-guarini_1_05-08-2025 (17:05):
Yeah,
great question and it's cool,
interesting too.
'cause I feel like the chief ofstaff role has grown a lot in BC
over,
emily-sander_1_05-08-2025 (17:11):
Yeah.
remi-guarini_1_05-08-2025 (17:12):
don't
know the, like, number of years,
but I've just seen it becomelike more and and more common.
I think, I mean this is alwayskind of the answer to chief of
staff related things, but itreally depends on the general
partner, you
emily-sander_1_05-08-2025 (17:23):
Yeah.
remi-guarini_1_05-08-2025_ (17:23):
like
kind of the ultimate decision
maker firm and also thestructure of the firm.
You know, like is it multiplepartners, is it, is it one gp?
Like how, how does it all kindof work?
Um.
You know, at, at the firm level,especially with like solo gps or
lean teams or, or younger VCfirms, I think a chief of staff
with an ops backgroundespecially could be like
(17:45):
extremely impactful
emily-sander_1_05-08-2025 (17:46):
Yeah.
remi-guarini_1_05-08-2025_160 (17:47):
a
lot of VC firms don't.
Always have the management fees.
basically what your budget is,right?
Management fees, um, that youkind of call on a quarterly
basis.
Think of that as like yourincome or revenue in a way.
That's what's paying salariesand things like that, that you
often don't have the fees tolike cover.
Having an HR person having this,you know, every single function
(18:08):
if, and so if you could have autility player that could fill
those.
Kind of gaps and holes and stillcreate a best in class structure
that provides a lot of value tothe team, the portfolio, the
like leaders of the firm.
Um, I think like in terms ofthen getting, I've seen more of
like that kind of model.
emily-sander_1_05-08-2025 (18:28):
Yeah.
remi-guarini_1_05-08-2025_1 (18:29):
And
then I also see, you know,
chiefs of staff that are alsoreally like deal, you know, they
work with a partner, maybe notthe GP that's overseeing the
whole firm, but a partner incharge of like the healthcare
vertical.
And they are really like.
The deal kind of, uh, likeassociate to that partner, but
also operationally keeping themon track with all of their
(18:50):
to-dos for their portfolio orother things within the firm.
I've seen a little less in theVC context of people, VC firms
deploying chiefs of staff intothe portfolio companies.
I see that a bit more in pe,
emily-sander_1_05-08-2025 (19:06):
Yeah.
remi-guarini_1_05-08-2025_ (19:06):
I'll
say, I think like generally.
It's likely better for, um,companies like for portfolio
companies to hire their ownchief of staff if that's
something that they need.
emily-sander_1_05-08-2025_ (19:19):
Yep.
remi-guarini_1_05-08-2025_160 (19:19):
I
think it can be tough to like.
Come in and, and deploy somebodyin to do like a certain project
or something like that and notbe like completely hands-on and
involved in everything.
I think that's where a chief ofstaff really adds value and
impact.
Um, and they'd likely be betterserved by like that, that
founder, knowing exactly whatthey need as a chief of staff
(19:41):
and, and bringing that person in
emily-sander_1_05-08-2025 (19:45):
Yeah.
Do you see a lot of foundershave a chief of staff by the
time they get to you?
remi-guarini_1_05-08-2025_16 (19:51):
So
it depends.
We invest seed in seed roundsand series A rounds.
And so seed is and and is prettyearly.
And so sometimes we're, and evenwe do some kind of pre-seed,
even though we
emily-sander_1_05-08-2025_ (20:03):
Hmm.
remi-guarini_1_05-08-2025_16 (20:03):
it
seed, but we still invest, we
invest in some companies thatare like pre-product,
pre-revenue, you know, like
emily-sander_1_05-08-2025_130 (20:09):
A
dream.
It's an idea.
Yeah.
remi-guarini_1_05-08-2025_1 (20:12):
And
so sometimes that's like they
just, it's the founder and theyhaven't hired anybody yet at
this series A stage, which islike they've raised Capital one
or two rounds of cap of capitalbefore and they, they have a
team that's, yes, I'm seeing alot of chief of staffs like at
that stage and then chief ofstaff, some being a higher, at
(20:35):
that like.
Kind of initial funding roundstage, but it depends on the
type of company.
If it's a really highlytechnical company, they're often
maybe bringing on engineeringtalent, or other kind of folks
like that.
But chief of Staff is like avery popular role right now,
even at the seed early stage.
emily-sander_1_05-08-2025_1 (20:52):
For
sure.
Okay.
I'm seeing that too.
And then you had mentioned thescenario where maybe a partner,
like a healthcare.
Um, vertical or division has achief of staff.
And then can you say more aboutlike, what they would be doing?
Are they, um, like let's sayhealthcare is a main, uh, is a
main industry or as a main kindof focus for the VC firm?
Is that why that partner wouldhave a chief of staff?
remi-guarini_1_05-08-2025 (21:14):
Yeah,
exactly.
So like.
So, for example, at a VC Kimmywas one of the like founding,
you know, co-founders, foundingpartners.
She was not the GP of that firm.
That's,
emily-sander_1_05-08-2025_1 (21:23):
Um.
remi-guarini_1_05-08-2025_1 (21:23):
um,
Joe Lonsdale, she had a chief of
staff, she, for her investmentpractice, which was healthcare
and consumer.
Um, and really it's like a dealassociate, like somebody sitting
on all calls with you, diggingin really intensely into
diligence and really just beinga direct resource because you
have like a certain level of.
(21:44):
Steal like velocity and thingsyou're looking at that having
somebody that's completely intune with, with everything that
like you're working on and anddiligence and how you're
thinking about the world isreally helpful, especially if
they have a complementaryskillset.
So say you like need someonethat's quite like quantitative
because you're spending a lotmore time on the relationship
side,
emily-sander_1_05-08-2025 (22:05):
Yeah.
remi-guarini_1_05-08-2025_ (22:05):
like
allow you to that, uh, partner
to like multiply their impact byhaving, having this person in
lockstep with them,
emily-sander_1_05-08-2025_1 (22:13):
And
I'm more familiar with like the
PE deal teams, where they wouldalways have an associate who was
like the analyst and like thequant guy, and then they would
have like the managing directorand so forth for the more so the
relationships.
But VCs typically have.
Like 10 x the number ofporticos.
So you're like, the amount ofcompanies that you're working
with is just massive.
(22:33):
Uh, and so I'm only, I'm tryingto imagine what it would be like
to be a chief of staff with like200 plus in some cases for some
VC um, firms.
Like how you even manage that.
Uh, and I guess it's justaltitude of involvement for each
portco, but that's a wholedifferent animal when it's 200
in VC land in some cases versus.
(22:54):
10, 12 in a fund in PE world,so.
remi-guarini_1_05-08-2 (22:58):
Totally.
emily-sander_1_05-08-2025_ (22:58):
Wow.
Okay.
Okay.
remi-guarini_1_05-08-2025_16 (23:01):
it
depends again, also like on like
how the firm itself getsinvolved with companies.
Like do they take board seats?
Are
emily-sander_1_05-08-202 (23:09):
Right.
remi-guarini_1_05-08-2025 (23:09):
know,
real, what kind of like.
How do they interact with thecompany too?
and that will define it on topof like just like number of
companies as well, and also likedifferent life cycles.
You might have 200 theportfolio, but maybe some of
them are, you know, like stagehave exit, you
emily-sander_1_05-08-2025 (23:26):
Yeah.
remi-guarini_1_05-08-2025_1 (23:27):
are
like on their way to exit and
you're working really closely tohelp help them with that.
Or, you know, companies needdifferent things at different
times, I guess
emily-sander_1_05-08-2025 (23:34):
Yeah,
for sure.
So if, if someone's listeningand saying, oh, okay, I'm
interested in potentially beinga chief of staff at a VC firm.
It's.
There's some similarities tobeing a chief of staff for one
individual organization, andthen there's some big
differences.
What would you say in yourexperience that people would
need to be aware of, like, thisis a difference.
Like you, you will still have aprincipal, you'll still be, you
(23:56):
know, seeing across the boardand connecting dots and building
relationships.
But like, this is pretty uniqueto, to VC world.
remi-guarini_1_05-08-202 (24:04):
That's
a good question.
I would say like one compared tolike an an operating company,
like, um.
It's, you just have different,like kpi, like it's kind of a
different language.
One, like if
emily-sander_1_05-08-2025 (24:18):
Yeah.
remi-guarini_1_05-08-2025_ (24:19):
from
like me coming from fashion, you
know, for us it was like allabout like the customer and like
average order value and how muchtime are they spending on the
site and what's a conversion andstore traffic and all these
things.
And for vc it's a wholedifferent set of KPIs and, and
terminology and, and all ofthat, which is different.
(24:40):
Um, and also you don'tnecessarily, you know, there's
not like a direct you, you'renot like selling a product to a
customer
emily-sander_1_05-08-202 (24:46):
Right.
remi-guarini_1_05-08-2025_16 (24:46):
of
like managing this dual
relationship between portfoliocompanies and, and LPs.
Um, and in some ways LPs are,are really your.
Customer.
'cause you know, if, if they'renot giving you any money, then
you no longer have a fund.
Um, but I would say that's,that's a pretty, that's a pretty
big difference.
And then two, the investmentwork is obviously different.
(25:07):
It's project based.
You're real, like you're diggingin on something maybe really
intensely for a week or two, andthen you're moving on, you know,
to the next thing versus.
Um, you know, I'm working onthis like rollout across the
company that's taking months andmonths of time, I would say is,
is also quite different.
(25:28):
Um, I feel like there's otherthings that comes to mind
emily-sander_1_05-08-2025 (25:31):
Yeah,
those, no, those were helpful.
Do you think that there's, um,more of a financial emphasis,
like you have to at least have aworking knowledge of kind of p
and ls or budgets or forecastingor things like that?
Or is it like, eh, like itdoesn't hurt, but there's
certain chiefs of staff in VCfirms who deal nothing with that
side of the business.
remi-guarini_1_05-08-2025_160 (25:52):
I
am sure that there are like
definitely roles in venturewhere the chief of staff is more
of like the pure like.
I do the HR kind of oversight.
I'm doing like working, youknow, managing like LP
communications and, andrelationships and like internal
employee experience and thingslike that, which that skillset
(26:13):
like, you know, you don't needas much of that, like modeling
and, you know, p and l skillset.
emily-sander_1_05-08-2025 (26:19):
Yeah.
remi-guarini_1_05-08-2025_1 (26:19):
Um,
and then I think then there's
the other end of the spectrum,which is like they really want
you to actually be an investor,you know, kind of alongside
them.
I, I didn't actually have, like,I didn't come from baking or pea
or anything like that, and, andI came from like, you know.
Understanding and building out pand ls and managing p ls in a
(26:40):
business context.
So what I will say is like evenif you are like, oh, I haven't,
you know, been an investorbefore or I haven't like done
that specific workflow, ifyou've been an operator and
you've like interacted with orbuilt a p and l or you know,
done that kind of work within acompany, you have the skillset
to be able to figure it out.
(27:01):
You don't need to have like, youknow, years and years of.
Certain banking or whateverexperience, and so I don't want
that to like hinder peopleeither.
emily-sander_1_05-08-2025 (27:10):
Yeah,
yeah, for sure.
I, I didn't know anything.
I knew I operated teams and ranteams and did basic stuff like
that.
But for my experience with, um,growth equity, usually on the PE
side, like their language is,are like spreadsheets in some
cases.
Like you have to speak financein order to like get through to
them or to ask for budget or toget different approval for
things.
And so that really.
(27:31):
Um, as any chief of staff does,you learn on the fly and you
figure it out and like, oh,okay, if you want this, then I'm
gonna tee it up for you in, inyour language.
Um, so I was just curious ifthat was similar in the VC
world.
Oh, I'm also interested, so.
For me, for chief of staff, Ihad the whole like, internal
side of things.
(27:52):
And then there was the external,um, you know, strategic
partners, strategic, um,vendors, kind of the media and
press and things like this.
And I'm wondering is, is therethat split for you and like,
what does that external piecelook like for you?
And, or maybe more so Kimmy
remi-guarini_1_05-08-2025 (28:08):
Yeah,
so kind of in terms of like
partnerships and things likethat.
Definitely.
It's also just like a lot ofecosystem relationships,
emily-sander_1_05-08-2025 (28:15):
Yeah.
remi-guarini_1_05-08-2025 (28:15):
other
firms that we have great
relationships with operators inthe ecosystem.
For deal flow, you know, that wehave relationships with.
So there's a lot.
Relationship mapping in VC is soimportant and you spend a lot of
time doing that, honestly, nomatter what role you're in,
because it's so relationshipbased.
So I would say like that isdefinitely a huge part of just
(28:37):
like VC in general, it's been ahuge part of this role.
when it comes to things likepartnerships, that's something
that sits with, with me and, andyou know, with Kimmy, um, and
for us.
That's been to date, like lessof a focus, right?
Because we've been focused onthe fundraise and, and the
launch and everything like that.
And it will become kind of moreof a focus as time goes on.
(28:58):
But where we've kind of hadpartnerships is, you know, more
so also like with studentorganizations, um, on college
campuses where Kimmy can go andspeak.
But what that also does is itgives us access to a great group
of like emerging entrepreneurs.
Um, that we can createrelationships with, that we can
help get into vc, um, you know,or place in a job.
(29:23):
And so there's a lot of workthat we do around that.
Um, and then also a lot ofevents.
We've done a number of events,um, either with other firms or
with companies for operators andfounders and investors and
things like that.
And then on the PR side, firmstake different approaches.
decided to be, this is reallydriven by Kimmy this strategy.
(29:45):
Um, which I think is reallysmart.
We've decided to kind of abackseat and not have a massive,
like push.
Um.
That's not like a huge focus forus yet.
We're kind of, we're gonna likehave our website like launch
officially in our LinkedIn, butwe're not gonna do a massive
push behind that, um, becausewe're like still young and
(30:07):
building.
And that's not to say that wewon't in the future.
Um, but that's kind of how wewanna approach things from the
start, um, is to be a little bitmore kind of like heads down
and, and incognito.
But when we do get there, that'sdefinitely something that.
I'll be very involved in, butthat Kimmy will direct the
strategy of.
emily-sander_1_05-08-20 (30:27):
Gotcha.
And if you're talking to, um,maybe an aspiring chief of staff
or current chief of staff, butlooking specifically to get into
vc, what kind of advice or justkind of lessons learned or
things that you would wantsomeone to know going into that?
I.
remi-guarini_1_05-08-2025_16 (30:43):
So
you don't have operating
experience, get it.
Like it, it will make you betterfor your part, your like GP to
your portfolio companies to thelike firm as a whole.
Um.
Again, like a lot of firms haveto operate without, you know, a
lot of operational supportinternally.
And so having that experienceand being able to provide some
(31:06):
of that I think could beactually a big differentiator,
um, for vc.
And so also it'll make you abetter investor.
It'll make you actually havelike great impact, um, with your
portfolio.
So I'd say that, and then I'dsay like, spend a lot of time
like.
One, talking to a lot of people.
(31:27):
Like I probably had hundreds ofof people that I talked to, you
know, alongside Kimia as I wasdeciding kind of what was next.
Um, it's it kind that's likekind of how you get there in vc
because there's not always, it'sa little bit occlusive, like
jobs aren't always posted.
It could sometimes bechallenging to know where to
start.
Things usually happen throughpeople and they're usually the
(31:51):
key.
And so even if you're like, Ugh,I don't wanna go get another
coffee, like, go get that coffee'cause you never know.
Um, and then I'd say like reallystarting to zero in on like kind
of what kind of fund would youalso wanna work for.
You know, as you go through thatconversation, that process of
having all those conversations,like do you wanna work for a
solo GP where there's reallylike one person in charge?
(32:13):
Do you want it to be an earlyplatform?
you know, you have more abilityto grow because there's, it's
less top heavy.
Do you wanna go to a reallyestablished firm, um, because
you wanna like, learn, you know,kind of from the best of the
best or you like that more, youlike a more hierarchical and
less flat environment?
Um, do you wanna be really earlystage, later stage?
(32:36):
You know, what areas excite you?
Um, it's just like a companylike.
If you are working at a companywhere you're not passionate
about the thing that you'reselling, it is quite hard to
work hard for that company.
emily-sander_1_05-08-2025 (32:48):
Yeah.
remi-guarini_1_05-08 (32:48):
similarly,
I think that transcends to VC
too, where if, if I wasn'tinterested in, in healthcare and
consumer companies, it'd bereally hard to talk to these
founders all the time and, andto underwrite businesses.
So that's important too.
Um, and then, yeah, I think justlike knowing your own strengths,
you know, are you.
Are you that operator?
(33:09):
Are you an extremely, like, areyou a Do you have a great like
ability to network?
Are you really strong withnumbers?
And then like, find that firmthat's looking for that to, to
match their needs.
emily-sander_1_05-08-2025_13 (33:22):
So
I think just to recap what you
said, like there's so manydifferent kinds of VC firms out
there, and there's like boutiquefirms that specialize in one
super niche area, and thenthere's ones that are more
broad.
There's different stages, likeyou said.
Um, if like the, the board seatmakeup is important to you, some
people have like policies aroundhow they do that with all of
their, so kind of filter andpick the ones that you wanna go
(33:45):
in that direction.
And then I love your advice oflike, what are you good at?
What are you naturally good at?
What are you the go-to personfor other people for, and like,
what lights you up and makes youexcited to go work on something?
And if you kind of do the Venndiagram for those two things,
whatever's in the middle isprobably a good direction for
you to explore.
So I, I love that advice.
Um, if you are talking to a GPor a principal who has a chief
(34:09):
of staff in a VC firm, and it'slike some of these decisions
are.
Really high level, they'reimpactful.
It's high pressure moving fast.
What would you say in terms ofadvice for managing a chief of
staff?
remi-guarini_1_05-08-2025_160 (34:25):
I
think like just build trust
early.
Prioritize that.
I think that the chief of staffrole may work like the, the
chief of staff is fully in theloop and they're empowered to
act give them the context.
Don't just give tasks.
There's a lot going on.
I know, like it's, it's a veryhectic, busy environment, but
(34:45):
context really matters.
and it's gonna make them better.
Um, and then I'd also say like,investing in their growth, know.
Student staff roles can burnpeople out if you're, if you're
not careful.
And I also think generally too,staff tend to be kind of like
people pleasing.
We wanna help.
It's a service oriented role.
Right.
(35:06):
And, and sometimes a little bitof perfectionist, um.
So it can be really challenging.
You're working a lot and youalways have to be on, and you're
involved in really high impactthings.
So if your manager, you know,comes to you and is also like
investing in you, um, thinkingabout helping think about where
you're headed next and not justlike, what can this person do
(35:28):
for me today?
I think that goes a really longway too.
emily-sander_1_05-08-2 (35:31):
Context,
it can take an extra 30 to 90
seconds, but that time couldsave you so much in both like
production time and likeeffectiveness, quality, just
back and forth.
So I love the fact that youmentioned context.
And then is there anything thatyou and Kimmy do just to kind of
make sure that you're, I.
In open communication and you'resinging off the same sheet of
music.
I mean, I remember with myprincipal, CEO and our COO, when
(35:55):
we would get stressed, we'd belike, let's just go out and play
some Topgolf.
And we would go out in theevening, just go like, play some
fun, like silly, stupid Topgolf,eat really bad nachos and you
know, drinks and just kind ofspend time together doing
something that we're all prettybad at, but have fun doing.
So I'm just wondering, is thereanything like that with you and
Kimmy.
remi-guarini_1_05-08-2025 (36:13):
Gosh.
Yeah, I mean, like, probablytalked to her more than anyone
else for like constantlycommunication and, and I think
that's just the nature of therole.
Um, but I would say like, yes,doing those things that are, you
know, a little bit morepersonal, go a long way.
Like for us that's a lot oftimes like.
(36:35):
Talking about like the next, uh,like clothing drop at Hill
House, like what's coming outand what are you gonna buy and
what am I gonna buy?
And we're both interested infashion.
So like, oh, did you see thisnew collection that came out?
And kind of like taking 10minutes and doing that.
Um, you know, versus banging ourheads against the wall about
something else.
Um, or going on a walk, going tograb lunch, like getting time
(36:57):
kind of out of, out of theoffice together too.
Um, but I find that like.
the relationship building at thefront where you have that trust
and you're able to.
Feel comfortable likecommunicating, kind of getting
what you need in any moment canalso alleviate, you know, some
(37:17):
of that.
And so, like for example, I feelvery comfortable if, even if
it's like 8:00 PM but if Ireally need an answer on
something, just calling Kimmyand being like, Hey, sorry, five
minutes, like need, need thisanswer.
And she gets that and is open tothat.
But I think it's hard to do thatunless you.
First build up the relationshipand the trust and empower the
(37:37):
person to do that.
And she empowered me to do that,like from the beginning.
emily-sander_1_05-08-2025 (37:41):
Yeah,
remi-guarini_1_05-08-2025_16 (37:42):
so
I think that's important too.
emily-sander_1_05-08-2025_13 (37:44):
it
is the, the upfront work is so
important'cause it sets thefoundation and then it's like, I
know that it's important if Remyis calling me at 8:00 PM at
night, it's not just like I'mringing my bell for no reason.
remi-guarini_1_05-08-2025_ (37:53):
you.
emily-sander_1_05-08-2025 (37:54):
Yeah.
Beautiful.
Remy, as we wrap up here, isthere anything else, uh, across
all the things we've talkedabout, vc, chief of Staff,
fashion Neon that you would wantpeople to know?
remi-guarini_1_05-08-2025_1 (38:07):
No,
just that I think, um, I think
the chief of staff role isreally special.
I think like if you're curiousand if it seems exciting to you,
like.
Go for it.
I think it can change thetrajectory of your career.
Um, I think it can accelerateit.
Um, and I think there's also anincredibly, like amazing group
(38:28):
of chiefs of staff, you know,across industries.
That are all like, really readyto dig in and, and talk and
help.
Um, especially somebody that's,that's newer to the role.
Um, it's pretty awesome, likehow kind and like open, most
chiefs of SAP are.
And so I'd also say like, don'tbe afraid to like reach out to
(38:49):
that person on LinkedIn thatyou're curious about their
career path and, and kind oftalk through it or you know,
something like that.
Um, and I'm always open to thattoo.
emily-sander_1_05-08 (38:57):
Beautiful.
And, uh, last question here.
If someone is kind of like, oh,like neon, and that sounds, that
kind of sounds interesting, uh,I might wanna reach out.
Like, what types of people wouldyou be excited to partner with
and what types of people shouldreach out to you or Kimmy or
Neon?
I.
remi-guarini_1_05-08-2025 (39:12):
Great
question.
I mean, definitely like anyonethat's looking to break into vc.
Um.
Or like kind of career, likemake a career shift, even if
it's not right into vc.
Both Kimmy and I spend time eachweek, like individually meeting
with people, making careerchanges, and, and helping make
intros and think about what'snext because both people have
both, like people have both, uh,taken checks on both of us
(39:35):
rather.
And so we like to do that andkind of be thoughtful that way.
So I'd say that generally, I'dsay definitely a.
Consumer early stage, likeconsumer healthcare founders,
um, would love to meet folksthat in, in those realms.
And then also, you know, wespend a lot of time on this, uh,
like a side fund called NeonPink, which is, um, we built to
(40:01):
kind of close the confidence gapand, and educate women on.
VC investing, get more women oncap tables.
And so we do like quarterly kindof education uh, like round
tables around like VC memos,like 1 0 1 language, what's a,
like, safe document, things likethat.
So anyone that's interested inlike learning more about angel
(40:23):
investing or VC in general,always happy to, to chat with
them too.
emily-sander_1_05-08-2025_1 (40:28):
Be.
Fantastic.
I love that name too.
So we'll have all of thatinformation in the show notes.
But Remy, this has beenfantastic, so thank you so much
for being on.
remi-guarini_1_05-08-2025 (40:36):
Thank
you so much.
I really appreciate it.