Off to the Valley

Shruti Kapoor: You are not your startup.

And two is, your startup success
or failure is not just about you.

Right.

It's about so many other things and
therefore being much more open to saying

like, hey, you know, this is a playground
and there are many things that are going

to impact how this playground pans out.

Prateek Panda: Hello everyone and welcome
back to Off to the Valley where we explore

the stories of entrepreneurs, innovators,
and leaders who are shaping industries

and creating impact on a global scale.

I'm your host Prateek Panda
and we are honored to have

with us today Shruti Kapoor, a dynamic
leader with over 15 years of experience,

spanning across investment banking,
technology and sales enablement.

Shruti is the founder of Wingman,
a sales enablement platform that

was acquired by Clari in 2022.

She went on to lead Clari's
international business.

And she's currently also a mentor
and coach to other founders.

Her career is fascinating blend of
strategic leadership, tech driven

solutions, and personal development,
making her an inspiring figure in

both the startup world and beyond.

Shruti, it's a pleasure to have
you with us today and we are

eager to dive into your journey.

Shruti Kapoor: Thanks for the
generous introduction, Prateek.

Excited to be here.

Prateek Panda: Great.

So let's start with this, right?

You've had a very diverse career.

You were working in investment
banking, typically pays well,

a lot of travel, good projects.

What motivated you to move
into tech entrepreneurship?

Shruti Kapoor: Yeah, so I think,
tech was always my first love.

I, did my undergrad in life sciences.

So always, the science and technology
space was very exciting for me.

In fact, even my investment banking
was in the telecom and media sector,

which, of course, you know, back in,
2007, 2008 was undergoing a massive

shift, especially in Asia, with the
privatization happening across the board.

And in fact, one of the deals
that I worked with while I was

there was the Friendster deal.

So, that's kind of where we were at that
point in time, right, with social media

and, tech just beginning to spawn and have
kind of another life after the 2000 bust.

So at that point, when the opportunity
came up to actually work for the fund

that was investing in really early stage
tech working with university researchers,

that was pretty exciting for me.

And it basically was one
gradual shift at a time.

So went from investment banking
to investing in early stage tech

and that allowed me to continue to
be really close to the tech world

to the startup ecosystem as well.

And, slowly, I think that pull
got me all the way to starting

up my own company in tech.

Prateek Panda: That's amazing.

Did you have any kind of
background from the past, like

in the family or anyone that was
particularly inspirational to you?

Shruti Kapoor: There wasn't so
much an entrepreneurial thread as

you would traditionally imagine,
but my father is a dentist.

And, what you realize is that
if you want to build a private

practice it is actually very
much like, being an entrepreneur.

So I think seeing that closely
was very interesting for me.

And I would say that was maybe, the
closest thread I had, because he, re-

rooted himself from being in a small
town in up to moving to Lucknow to

establish his practice from scratch.

So just seeing that,
how did he build it up?

What was his way of doing marketing?

How do you do good NPS
scores with your customers?

The pre CRM era of having
cards and I was always closely

involved in his dental practice.

I was his so called
assistant through that.

And I would kind of help
him keep records of things.

So, yeah, that was, inspiration.

Prateek Panda: Awesome.

Thanks for sharing that Shruti.

Talking about CRMs and enablement
and sales, you founded this

company called Wingman.

Can you tell us a little
bit more about it?

Shruti Kapoor: Yeah, absolutely.

So, you know, the idea was really simple.

When I was in the business development
and sales side, one of the biggest

challenges I faced was the customer
would give us some feedback that could

be very interesting for marketing that
could be very interesting for product,

but it was very hard to actually channel
that back and, you know, by the time you

translated and shared that information,
it didn't kind of have the same impact

as the customer telling you what they
were thinking and why they were thinking

that, and so that was kind of one reason
why I was thinking like, hey, instead

of having to then arrange another call
with the customer and the product team

to get that feedback loop going, uh,
wouldn't it be great if like I could

actually just have that call recorded
and sharable with my product person,

and then the second thing, as I started
managing a sales team was like, I had

people who were working super hard,
but not seeing results in their sales.

And then there were people who would
just know where to put the effort and

they would always be hitting quota.

And as a person trying to manage
that sales team, I felt it

was my responsibility to help.

People figure out what was working,
what was not working, but it

was really hard to do that with
just post facto conversations.

So, fast forwarding a little bit
with Wingman, what we did was

we said, hey, there is a lot of
valuable information and sales calls.

And this is back in 2017, 2018, when
it wasn't so acceptable to be recording

every meeting, like today you have,
a bot literally on every meeting.

And the idea was like, hey, what if
we could record every sales call and

then get specific insights that could
help the business in that process of

either sharing the voice of customer
with other teams, making strategic

decisions based on voice of customer.

And of course, helping salespeople
and sales teams to get better in

their performance across the board.

And then, very specifically what we did
was, we developed a board that could.

Join these meetings that would
do the transcription of the calls

and that would give in real time
feedback to the salesperson.

So while the salesperson was on the
call, if a question got thrown at

that person, then it would surface
information saying, hey, this is how

you compare with this competitor or,
you know, these are the other customers

you've sold to in this industry.

So it would give them immediate
feedback, immediate access to content.

It would even give behavioral feedback.

So, you know, you've been speaking for
too long, or you're speaking too fast.

And of course, all of the post
call stuff that we are much more

familiar with today, which is,
create a follow up email for you.

Create call summarization and then do the
aggregate comparison across salespeople

across different deals and all of that.

Prateek Panda: That is amazing.

Yeah, like you rightly said, a lot of
this today, we almost have started to

take for granted, but it's amazing that
a few years ago you were able to sort of

build all of this into the product and
rightly it brought you to Y Combinator

and although it has been a few years since
you folks graduated out of the program

but can you tell me a little bit about
your experience with the YC program?

Shruti Kapoor: So this
was in summer of 2019.

We were literally the last batch that
was able to do it fully in person

before the pandemic, came upon us.

And it was really
exciting for many reasons.

And then there were, of course,
many practical takeaways.

I think just everybody
has always heard about YC.

I'd never really spent any time
in the valley at that point.

I'd work with companies in the U.

S.

I traveled.

But not really spend that much
time in the valley itself.

So that, you know, one was, it was
just a very prestigious program.

So getting into it
automatically opens doors.

So, I like to call it like, you do an MBA
and it's not so much about what you learn

there, but it's as much about the network
you build and the stamp it gives you.

YC is definitely a strong stamp.

No doubt about it.

Your fundraise process, it was very
smooth, at least in those days,

there was pretty good equation
between the demand and supply.

So that was fantastic.

But I think the most lasting
impact has been, just knowing how

difficult the founder journey is.

And I think YC does a really good
job in letting people understand

that, hey, there are going to be
ups and there are going to be downs.

And every founder like whether it's Brian
Chesky or Patrick Colson, everybody goes

through those ups and downs and hearing
it from their mouth on how they have gone

through it, how it's really changed them.

What are some of the lessons they've
learned is very useful because,

you know, invariably, you will go
through that in your own journey.

And then, like, you feel like,
okay, I'm not the only idiot.

I'm not completely incompetent.

It's just part of the founding journey.

So, yeah, I think it really brought
together a lot of appreciation for that.

And then I think the second part
of it, again, goes back to people

and their growth, right, which is
YC really makes it clear that the

most common reason why companies
fail is co founder relationships.

One is it became a forcing function
for us to anyway, spend three months

together living in the same apartment
through YC, but they kind of give you

some useful frameworks to work through
conflicts that you might have on how

to make sure that you anticipate those.

And I think, again, that's one of
the things that is going to outlast,

you know, your initial fundraise and
the theory of how to do your zero to

one GTM because those are things that
you're going to have to deal with

throughout your founding journey.

Prateek Panda: Yeah.

I would imagine that, in addition to the
things that you said, just having that

community where you have other people in
a similar journey, similar stage would

have been very helpful to really sort of
get that feeling that you're not the only

one experiencing all the highs and lows.

Shruti Kapoor: Yeah, that's true.

Um, though I would say like, back
home in India, we also had a pretty

good community with SaaSBoomi
helping a lot of the SaaS founders.

That's even more, I would say consolidated
group in terms of the learnings that can

cross over because, everybody is trying
to be in the same field, sell to the

similar kind of audiences going through
the same product journey, so to speak.

So, yes, I think broadly speaking,
extremely useful to build your

community around you that helps you both
tactically through the ups and lows.

And of course, mentally
through the ups and lows.

Prateek Panda: Yeah.

And I think, you know, you gave a
great example of SaaSBoomi and I've

seen them over the years become this
really helpful, close knit community.

I've had a chance to participate in
multiple of their events in the Bay Area.

But talking about communities, the U.

S.

or Silicon Valley in general also
has this sort of community vibe.

We spoke about SaaSBoomi in India.

You are currently sitting in Dubai.

Tell me what community means
in Dubai, at least as of today.

Shruti Kapoor: Yeah.

So, I've been in Dubai now for almost
three years, and I think Dubai has been an

interesting melting pot for people coming
in from different parts of the world.

There are things that are available here.

And I think there are things
in the ecosystem that are still

missing that need to build up at
least from an entrepreneurship or

tech entrepreneurship standpoint.

I would say that it's still a lot
more in the nascent stage, right?

Like maybe think of it as India,
maybe 5, 6, 7 years back, right?

When people were trying to figure
out, I think there are definitely

clusters in FinTech in the world of
cryptocurrency, et cetera, but more

broadly speaking, it's a lot more nascent.

And that's also because,
it's a very different market.

All right.

So in some ways, if you think
of it, especially as a tech

market, it's much smaller.

And also in it's tech adoption
curve, it's much earlier, right?

Which opens its different types of
opportunities because it's a market

that is different from India in the
sense that the ability to spend or

the per person cost is anyways high.

But it's similar to India in the
sense that the tech adoption is low,

right in some cases, even much lower
than India in a business context.

So it's an interesting dynamic of its own.

Prateek Panda: So for all the
other founders that are listening

to this episode, right, and I
know many of my founder friends in

India have all contemplated about
moving to Dubai at some point.

People keep thinking about
moving to the Valley.

That's where customers are.

The network is stronger,
more capital and so on.

Based on all the things that you said
right now about Dubai, do you think

that there is a segment of founders
that might benefit being in Dubai?

Is there like, what would you say
is the right reason to be in Dubai?

Shruti Kapoor: Yeah.

So I think, one of the things with
Dubai is, definitely it's the most well

connected city in the world, right?

So if you're still in the phase where
you're figuring out your market, and

I know a lot of people go through that
journey of saying, like, yes, US is a

pretty difficult,bet, maybe our product
will service a different market better.

And in that case, you know, Dubai is
a good spot for you to both figure

out the Middle Eastern market and
also the European market, right?

It's and also the talent pool access,
especially in terms of sales and their

language skills is pretty diverse.

Um, so, you know, if you're thinking about
like, hey, setting up a team that can sell

to different markets in Europe, et cetera.

It's going to be very easy for
you to find talent with whatever

language skills you're looking for.

Also the time zone tends to be quite
favorable say, as compared to people

who might be thinking between Singapore
versus Dubai, like one of my reasons

was like, hey, if I go to Singapore and
if I need to do anything with the West

Coast, I'm just going to like never sleep.

All right.

Whereas Dubai is a little bit in between.

India and, the U.

S.

So I think those factors definitely play.

And there is access to funding.

Funding ecosystem works a little
bit differently here than in the U.

S.

But, there are funds who do
want to invest in technology.

So I think that is another reason.

And then, definitely the proximity
and connectivity back to India, right?

So if you're thinking of having a
team in India and, you know, exploring

different markets, it's still a good
place to park yourself because you

could still be going back to any of the
Indian cities on a three hour flight.

And pretty well connected
to pretty much every place.

So I think those are some of the
big reasons and not to mention

the fact that it's fairly business
friendly, fairly tax friendly.

You don't have currency restrictions
like you do in India, in terms of like,

who can invest in you, who can't invest
in you, who can you issue ESOPs to.

I know a lot of founders
in India spend way

more time than they would ever,
ever want to, on figuring out like,

hey, RBI launched this new thing.

What does it mean?

And can I issue advisory equity?

And can I have people who are not
on my payroll have ESOPs like,

a lot of that mess that none of
us really enjoy dealing with,

Prateek Panda: Yeah.

I think all of that makes a lot
of sense and I'm definitely sure.

There's a lot of things that you mentioned
where, somebody can think a little bit

deeper and really pick if this is for
me and the good part about Dubai right

now is that it's so easy to access from
India, from so many different cities

that you can go spend some time and
get a feel for it before you really

decide, and it's not as significant as
a move as you have to move to the U.

S.

or Canada or whatever.

It still feels closer to home, at least
if you're from, moving from India.

On that note, switching context a
little bit, in about three years

from the time that you graduated out
of the YC program, you got acquired

by Clari, big name in the industry.

How did that acquisition come about?

Was that something that you folks as
founders planned or was it chance?

How did it come about?

Shruti Kapoor: Like, every good marriage,
there is always a little bit of chance

and a little bit of preparation.

But I mean, I think we were, like
the universe has to somewhat collude

to make certain things happen.

And I think acquisitions
are a bit like that.

In our case it's interesting
the timing, right?

So this was back in 2022.

I was like, okay, this is the time for me,
the world has finally opened up to travel.

Let me go and spend some more time in
the US and maybe meet some investors.

And while I was on that flight
from Bangalore to US, is when the

Russia Ukraine war started, right?

So I had no idea when, by the time I
landed in San Francisco, I got like

the first message I saw was, hey,
do you know Russia attacked Ukraine?

And I'm like, what?

And by the time I got out of the airport,
it was quite clear to me that the world

as we know was, feeling very different.

And like everybody was in this panic mode.

I think people had already been
talking about, hey, you know,

the markets are overpriced.

They're overheated and the valuations
are out of whack, and then like, this

was just the perfect kind of excuse
slash reason to say, okay, let's all

pull back and hold off and like not do
anything for a while, because nobody

knows what's going to happen in the world.

So just to say that, whenever you
think of stories of either, you know,

great successes, great failures, big
funding rounds, whatever it is, right,

there is so much else that impacts it.

That yes, people can go and say
that we built a great company or we

built a great product, but there's
like so much else outside of your

control that's always happening.

That was the context in
which I landed there.

And then, this was one
of the conversations as

part of my visit to the U.

S.

that I was having.

And at that point, given how everything
else was developing, it seemed like maybe

acquisition is a good option for us.

And as it transpired,
there were quite a few.

People who were interested
in the space, right?

So we had multiple potential acquirers.

And again, this is one of those things,
where something which seemingly looks

bad might actually be good, right?

So what was happening was that as an
industry, because the budgets for sales

tech were being cut, it meant that there
was a lot of pressure for people to

consolidate their sales, buying, right.

And sales tools were therefore
saying, like, let me give you a more

packaged offering that I am no longer
an expert in one thing, but, you know,

maybe I can give you like four tools
so that you don't have to go shop

for four different things, right?

So in that consolidation story is
where we therefore landed ourselves.

And again, the consolidation was somewhat
driven by the markets trying to come off.

The overheated situation
that they were in.

So, yeah, I think in the middle
of all of that, we became

somewhat desirable hot property.

And that's kind of how the whole
acquisition thing panned out.

Prateek Panda: Shruti, you said
something almost in passing, but I

feel like that is such a critical
skill to have, especially as founders.

You mentioned that you landed in the U.

S.

and heard about the war.

You already started reading
signals that the market is slowing

down and so many things, right?

And on the basis of which you figured
acquisition is a good opportunity.

I've made this mistake in my early days,
and I still meet with so many founders

who are so passionate about the problem
that they are solving that they are

almost oblivious to what is happening
outside, right, in the macro context.

Is there any sort of, since you've
been there in that sort of position

before, is there something that you
could tell other founders listening to

this on, why it's maybe also important
to, I know it's hard to emotionally

detach ourselves from our startups.

But at some points you need
to do a reality check perhaps.

And what is that time to do that, right?

Like, how do you be more open and
more receptive to all these things?

Shruti Kapoor: I think you as a
startup founder, you have to be

doing a reality check all the time.

And you have to be reading the signals.

And what each of those things could mean.

Sometimes they will play out.

Sometimes they won't, but it's
important to be trying to at least

mentally make those bets and make
those projections because it's, it's

almost like a muscle memory, right?

Like you slowly get better at it, right?

And say, take, for example, like
the Nvidia stock going down 20

percent or whatever in 24 hours.

Like, if you were looking at the situation
a week back, what was there anything that

would have made you think about this?

What would have made
you double down on it?

What would have made you
take a step back, right?

So

just things like that.

And I think it's,

it's important to be able to also
understand like what I said earlier,

right, which is there is so much out of
my control that whether there's a success

or a failure, it's not entirely on me.

So, there are several levels of
detachment, like you said, right?

One is you are not your startup.

And two is, your startup success
or failure is not just about you.

It's about so many other things and
therefore being much more open to saying

like, hey, this is a playground and
there are many things that are going

to impact how this playground pans out.

I think that's, kind of my one advice,
which is whatever story you read and

whatever story you're telling yourself
about your company is, your own part to

play in that is maybe 10 percent, right?

There is so much else
that's out of your control.

And I think just being able to
acknowledge and respect that eases a

lot of stuff mentally and hopefully
helps us make better decisions.

That's also some of the stuff that
when I work with founders now as a

coach, I try to do, which is like
try to help them understand what

other decisions that they're making.

Out of fear and what other decisions that
they are making out of real conviction.

And making sure that you over a period
of time, get better at making better

decisions and actually implementing
them because making the decision

is, sometimes easy, but making it
happen all the way through is harder.

Right?

So it was the same thing for us.

Like, even when the acquisition was an
option, it was still a lot of internal

dialogue on saying like, hey, is this the
time when we do want to consider this?

You know, we are growing well, there's
so much going for us, what if we just see

how this plays out for the next 18 months?

Prateek Panda: Getting co
founder alignment on that would

have been challenging too.

Shruti Kapoor: Yeah.

I mean, you have to get co founder
alignment, but you also have to get

yourself into a position where you're
like, okay, this is going to be

like a no regrets thing if I do it.

And, even if two years later, this
company is like, say, hey, 10x in its

revenues, will I go back beating myself
up or will I be like, yes, that was that.

And that's the two years of
my opportunity cost as well.

Prateek Panda: Yeah,
there's this quote, right.

You miss all the shots
that you don't take.

So, it's like, a lot of times
regret is there only because we

don't take an action on something.

It's rarely that you do
something and then have regret.

Why did I do it?

But typically when you are at a
crossroad, if you take an action,

you'll have usually less regret, but
because you at least gave it a chance,

for all the right reasons, hopefully.

You did mention a little bit
about you spending more time

with founders as a founder coach.

You are spending most of your
time as a coach these days.

Can you tell us a little bit
more about your practice and

what do you really specialize in?

Shruti Kapoor: Sure.

So, you know, the reason why I spent time
doing this is because when I was a founder

and the pandemic suddenly happened,
right, like, literally overnight.

I was like, okay, we are not really
well equipped to, deal with this

And I went and got like a coaching
service to help get coaching

support for everybody in my company.

And we were pretty small at that point.

Um, and I felt I really benefited from it.

It helped me understand things about like.

You know, basic things about how I make
decisions, how that relates to maybe

the beliefs I hold about myself and
how that might have absolutely nothing

to do with starting that business.

And so through that journey, I realized
like very often we have so many blind

spots of our own and especially as
founders, they get more and more layered

because over a period of time you get
so good at presenting the story that

you want others to believe in, that it
becomes hard for you to even know what

is the story that you believe in or
that you are questioning all the time.

So, yeah, I mean, today I basically
want to, hopefully reduce that misery

of the founder journey in some ways
for other people that I work with.

And the idea is really simple.

I spend, an hour or so every week
with each founder that I work with.

And the idea is you bring to the
table, whatever is top of mind for you.

We deconstruct it.

We work through either
tactical stuff around it.

So it could be a fundraise.

It could be like, I'm not
converting these pilots.

It could be, like you said, co founder
conflicts are pretty common as well.

So it could be any of those things.

And of course, that flavor keeps changing.

But the idea really is that can
somebody stand there and show you the

mirror and ask you the tough questions
that maybe you are running away from.

So, I look at myself more as, hey,
I'm here to show you the mirror.

I'm not here to solve your problems
because I know that you know how to

solve all those problems, but you might
not necessarily be doing a very good

job at identifying what that problem is.

And so, that's brought me what I do.

Prateek Panda: That's amazing, Shruti.

Thank you so much for sharing all of that.

And as we wrap up, any last pieces of
advice, if there's one thing you wanted

some of the founders listening to the show
to remember or follow, what would you say?

Shruti Kapoor: I think just remember
that you are not your company.

And things that are good or
things that are bad might happen,

but it's not all down to you.

So don't give yourself too much credit
and don't beat yourself too much either.

Prateek Panda: Yeah, I think that
is such great advice and so many

founders and since you mentioned
this right, I thought I'd just share

anyway and maybe you have more to add.

So many founders struggle with,
especially the bad days as founders.

Most of the times we see highs, yes.

But, the lows are like
just excruciatingly low.

The highs are high, but
the lows are terribly low.

And that's been consistent with so
many founders that I've spoken to.

And those are the days when you
feel so helpless also because you

keep tying or associating yourself
to the startup so strongly that

you think you are the startup.

And if that's going down, basically
you're going down, but that's not true.

And that's where we need that strong
community to help us realize, like

you just said that you have to
have that conscious detachment.

You have all the ability in you to turn
things back around or observe reality

trends and act accordingly, right?

And, I think, great piece of
advice, Shruti, thank you so

much for spending time with us.

It was amazing to hear from you
and I'm sure a lot of our listeners

are going to find this helpful.

Shruti Kapoor: Thanks Prateek.

Yeah, hopefully we get the right
messages and hopefully we have

fewer stressed out founders.

I don't know if that's possible, but yes.

Prateek Panda: Definitely.

Thank you so much again, Shruti.

And that wraps up today's episode.

Before we sign off, I would like
to thank you for your support

and thanks for tuning in.

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