Off to the Valley

Tim Grassin: We're both doing
it, so we know it works.

whether or not you're doing direct sales
with your podcast, meaning the guest

is the target, or you're doing top of
funnel, meaning future listeners are

being nurtured into a sale, It works both
ways and it's pretty fantastic strategy.

Prateek Panda: Hello and welcome
back to Off To The Valley, a podcast

that brings to life the journeys
of extraordinary entrepreneurs who

have ventured beyond the familiar
path to create something remarkable.

I'm your host Prateek Panda, and today
we are thrilled to be joined by Tim

Grassin, a serial entrepreneur with
three successful exits under his belt.

Tim's latest venture, Next Big
Wave, is a growth program designed

to help B2B startup founders in
Southeast Asia scale their companies.

He has a fascinating background, having
grown up in places as diverse as Kenya

and Finland before making his mark
across Southeast Asia with ventures

like TendoPay and Candy Banners.

Over the last 15 years, he's honed
his skills as a growth strategist

and built a wealth of playbooks
to help B2B startups scale.

Beyond his ventures, he's also
an avid traveler, extreme sports

enthusiast, and an angel investor.

Tim, it's an absolute pleasure
to have you on the show.

Tim Grassin: Thanks Prateek.

Lovely introduction by the way,
well researched and very flattering.

I appreciate it.

Prateek Panda: Thank you so much.

And, you've been doing some amazing
work and you've had tremendous amount

of experience on the B2B growth side.

But before we get into that, tell
me a little bit about yourself.

You grew up in a household where
both your parents were diplomats.

How was that growing up?

Tim Grassin: Just my dad.

Sorry.

My mom was raising us kids.

She had the odd job.

She was working for charities like,
Orphans Without Borders and things like

that, but mostly, raising the kids.

And my dad was a diplomat.

He started being a diplomat later in time.

So, he was initially working for
the French Ministry of Education.

So, a teacher.

And then opportunities to work abroad
through the Ministry of Foreign Affairs.

So becoming a diplomat and yeah, that
kicked off my journey as a world traveler.

Like you mentioned, we traveled
in countries at least at the time,

foreign as Finland, Kenya, the
UK, Denmark, and a few others.

But, overall, I picked that habit
up and decided not to stop, uh, when

I eventually left the family home.

Decided to continue on and move to
Canada for myself and then later

Southeast Asia, like you mentioned.

Prateek Panda: That's amazing.

Tell me how Southeast Asia happened.

Was it because of a work opportunity
or were you exploring and

decided you liked living there?

Tim Grassin: So it was purely for work.

In my second company that you
mentioned earlier, Candy Banners, I

was looking for developers as well as
creatives that were more affordable

than what I could find in Toronto.

And I reached out to several
countries that are on the list of

near shore and offshore workers.

And the Philippines just
happened to be one of those.

And through various trials and tests,
I realized that the population in the

Philippine was very hardworking, spoke
English, they had all the skills that

I was looking for and the prices back
then were relatively affordable still.

I think things are changing rapidly, but.

Relatively affordable and that prompted
my first trip to the Philippines and

from then on I grew the team to close
to 40 And basically the majority of the

team for candy banners was in Manila.

So I was going back and forth
probably two-three times a year And

yeah, that's how I started getting
exposed to southeast asia overall

Prateek Panda: You did mention
about finding resources in the most

cost efficient way to be one of
the reasons that got you motivated.

You did also mention that
things might be changing.

What do you think is the current
Scenario with startups in Southeast Asia.

What do you observe that has
changed now versus a few years

ago when you first moved there?

Tim Grassin: So I was mostly referring
to the cost of labor that was evolving.

I think the Philippines got on
the map not that long ago in terms

of people leveraging, their skill
sets, for more than call centers.

And, a lot of people started
talking about the quality of the

work and all of those things.

So there was an influx of, or at
least a wave of hiring that happened.

And while I was in the Philippines
for the last six years, I noticed

that prices started to skyrocket.

I think that has calmed down a
lot because people started looking

elsewhere as the prices started to grow.

And also the ascent of AI has taken
or tackled that as well, because

a lot of the creative roles that
were coming out of the Philippines

are slowly being replaced by AI.

And unfortunately, That has sort
of put pressure on prices there.

So overall, I think it's going
up and down based on needs.

It's pretty basic supply and demand
game, but you're asking about

the startups in the Philippines.

So that is a different topic,
but I was one of the first

sort of batches of startups.

When I moved to the Philippines
for my last company, TendoPay, we

were one of the first startups.

When I say that there were probably
20 startups altogether when we

moved there, it was really small
and absolutely zero capital.

The VC scene in the
Philippines was close to none.

Angels were few and far apart.

That's changing quite a bit.

I'm seeing a lot of startups in
the Philippines lately, a lot more

capital flowing into the country.

I think for founders who are expat
founders, they've realized that it's

a country that operates in English.

So it makes it a lot easier if you
want to do something in Southeast Asia.

You really only have a few choices.

I mean, you have Hong Kong and
Singapore, of course, Malaysia is an

option, but Philippines is pretty much
the easiest one in terms of language.

So that's helped and then, There have
been a few successful exits in the

country as well as a few unicorns.

So smart money has started to look at the
Philippines a lot more, invest becoming a

lot more Interested in the country overall
so that has also led to a wave of local

founders that have awakened to the idea
that, Oh, the Philippines is a country

where I could start a company, which
was not really a reality before that.

So a lot of inspiration
for local founders.

And yeah, I would say one in 10
founders I speak to right now is

in the Philippines and I speak to
everyone across Southeast Asia.

So it's like more represented
than they used to be.

Let's put it that way.

Prateek Panda: That's pretty cool.

I spent a fair amount of time in Singapore
and, I spent three years there and my last

startup was headquartered in Singapore,
it's still headquartered in Singapore.

And we spent a lot of time moving
around in that region and working

with a lot of venture capitalists who
focus on the Southeast Asia region.

So I've seen it evolve quite a bit.

And I'm talking about 2014-15 when
we first started exploring Singapore

and Southeast Asia as a market.

You've been helping a lot of
B2B founders in the region with

your new startup Next Big Wave.

Tell me a little bit about that.

How did it come across and what
do you really help founders do?

Tim Grassin: So I wouldn't
call that one a startup per se.

I really created Next
Big Wave out of boredom.

After selling tendo pay, I knew that
I wanted to stay in Southeast Asia.

But I decided to move out of the
Philippines cause it was about

time in my life, every four years,
I consider where to move next.

And I decided to come to Bangkok.

I really liked Thailand.

I had spent a lot of time here
and the idea was for me to find

something to do while I was figuring
out my next product, let's say.

So I started writing a lot
of content on LinkedIn.

I decided to start a podcast.

Kind of similar to yours, founder
for founder type of thing, to

engage with the founder community
in Southeast Asia, which I feel was

quite underrepresented in podcasts.

And through that, I started talking
to lots of different founders

and started poking around and
understanding what their needs were.

And I realized that My background
in growth was a very in need

background for most startups.

A lot of smart CEOs, a lot of smart
ideas, but growing is something that

they didn't really learn properly.

And there was not a lot
of talent in that space.

So I started consulting
with a few startups, just to

see what was up with them.

And I realized that the man
was a lot higher that I could

handle as a single coach.

And I got introduced with the notion
of building programs through platforms

like school where you can sort of dump
all your brain or your knowledge into

a video course and enable like one too
many coaching so they would absorb your

playbooks and your different strategies
and then you would implement them in group

calls or occasional one on one calls.

And so that's what I did.

And again, this was really just out
of boredom or sort personal curiosity.

So I built that in probably the last
six months and started onboarding

companies just over a month ago.

And so that's what my day to day looks
like right now is just coaching B2B

startups and teaching them a few playbooks
that have worked for me in the past or

that I'm developing right now as I'm
seeing things evolve in the region.

And, That's not to say that, you know,
I'm not interested in, I really love

what I'm doing and teaching is kind
of new to me, but exciting, but I'm

probably still going to eventually build
an actual product, an actual startup.

It's just a matter of when.

So this is really a big transition
for me, which I love doing and I might

keep doing on the side, but I don't
know if this is my next startup per se.

Prateek Panda: Got it.

And there's a couple of things I want
to double-click on there, but first

things first, for all the B2B founders
that are listening to this, can you

share a couple of growth strategies that
you've seen work pretty consistently

that they can go ahead and try?

Tim Grassin: Yeah.

So the first one that I teach everyone
in my program is founder led sales.

Essentially what I noticed is that
there are a lot of great founders

that are getting a ton of traction,
whether it's from their customers

or from investors, simply by putting
themselves out there and being the

face and the voice of their company.

And it sounds obvious when you say it
like that, but a majority of people

that start companies shy away from
that idea and want to be the introvert,

hidden ceo whereas they should be the
front runner of their own companies and

their businesses and I give examples
like Elon Musk to illustrate this.

And obviously, Elon Musk has impacted
the sales, the stock prices, and

all of that for his companies while
being an actual like introvert.

And he's been trained to be
a public speaker, but his

personality doesn't scream that
he loves being in the limelight.

Right?

So every founder, in my opinion,
should put themselves out there

and there's no better salesperson
than them for their company.

And it's just such a low-hanging fruit.

People love being part of your
adventures and your stories and

getting to know you on a deeper level.

And at the end of the day, people buy
from people is what I like to say is

that you'll be able to sell a lot more
if it's coming from you rather than

Your company trying to promote itself,
just being an entity that has no soul.

And so, I teach people to, to
create founder-led sales strategies.

That's one of the main things that I've
been doing and it works quite well.

And then I have other
content-related playbooks.

So one of the playbooks that I used
at TendoPay, that was probably the

single most, powerful tactic that we
use was creating an industry podcast.

Not too far from this one.

And the idea was, we were hitting
a wall with our ICP and we couldn't

really get any response rates.

We had ran through thousands of
emails and we knew who they were.

We knew exactly where they were.

We just couldn't get them to
respond or be interested in us.

And then we had this idea to create
a podcast that would be of interest

to them, something that they wouldn't
mind talking about for 30 minutes, 45

minutes, something that they felt they
would bring value about and something

that would flatter their ego to be on.

And we created this very low key
branded podcast about something HR

professionals are interested in because
we were targeting HR professionals.

And we started reaching out to the
same group of people we had reached

out in the past, asking them to
appear on a podcast that would

be something of interest to them.

And the response rate shot up from
less than 2 percent to close to 30

percent on some of our campaigns,
with a positive response rate of 70

to 80 percent sometimes depending
on the campaigns, of course, but.

It's actually like, life change in type
of numbers compared to what we had before.

And the idea was I was doing the
podcast at a time and I could handle

maybe one or two a day, but then I
started training my SDRs to run these

podcasts because it wasn't that scary.

Like they were running through
five to seven questions,

making the guests feel good.

And then the idea was to groom that
guest into being sold on a demo call.

And so the way we did that
is we would make sure that

first of all, they liked us.

We built an authentic relationship
with them through the podcast.

And we had questions that would highlight
some of the pain points they might have.

And at the end of the conversation,
we'd be able to say, Hey, I realized,

you had this pain point and You know,
I don't know if you know, but we also

work on this other company because the
podcast was separate from the brand.

And this is a pain point that we're
used to solving for our clients.

And, maybe we could jump on a quick
demo call about our product to

see how we could solve it for you.

And more often than not, we would
get a positive response on going

on a demo call, but if not, we had
them in a nurturing sequence and

they're already warm because we had
spoken to them for 30 to 40 minutes.

So, yeah, that filled up our
pipeline quite significantly.

And that's a playbook that a few of the
people in my groups are using as well.

And then a lot of other stuff
around signal based sales.

So always using data or content to
create more warm outbound strategies.

That's the idea.

Prateek Panda: That's amazing.

It's interesting that you shared
the example of the podcast, Tim.

That was my experience in my
last startup that I was heading.

We use podcasts as a way to
exactly do what you said.

And it was mind blowing for me.

It came as an afterthought.

The idea for the podcast was more around
building thought leadership and awareness.

And there was a period when we were
not able to move enough deals through

the pipeline and we started figuring
out, Hey, we're knocking enough doors.

It's just sitting there and something's
not moving, or we are not able to

get in the attention of some of
the high value customers that we

want their attention on, right?

So podcast became a great way for us
to achieve very similar results as

what you mentioned, but I was smiling
when you were sharing this because A,

it reminded me of my experience a few
years ago, but B, I've been trying to

actively tell this to founders, but
there's been a significant amount of

resistance to doing something like this.

Largely because people think yes,
podcast is a lot of effort, which it is

having run this podcast now for a while.

I know it's a lot of effort, but like you
said, there is a method to the madness

and a great way in which you can Get
high ROI and it's absolutely worth it

Tim Grassin: Yep, I agree.

We're both doing it, so we know it works.

whether or not you're doing direct sales
with your podcast, meaning the guest

is the target, or you're doing top of
funnel, meaning future listeners are

being nurtured into a sale, It works both
ways and it's pretty fantastic strategy.

Prateek Panda: Yeah, tell me a little bit
about uh your experience running services

business as well You had an acquisition
with your service business also

Tim Grassin: Both my service businesses
got acquired, before TendoPay.

So Stinson design and Candy Banners,
and those are completely entirely

different businesses, right?

So what was interesting for me there was
finding a high-value service that I could

productize and essentially systemize every
single process around, scale it as much

as I could, within the timeframe where
I was going to run out of or what I was

going to become bored, which first service
businesses, let's say four to five years,

you start getting bored of the repetition.

So I would scale them, systemize
them and then sell them.

Majority of the sales happen out of
pure luck, but regardless, it was

really a game of just like automating
the business as much as possible.

And by the fourth year, usually I was
able to automate most of it, have people

in place to run it and it would have
become a cash cow if not acquired.

So I knew in the back of my mind that
it was a business I was building just

to leave in place and let it run.

I wasn't going to scale it forever.

Sorry.

What did you want to know about those?

I just went on a rant

Prateek Panda: So, yeah, I think one
thing to know is you mentioned, that you

knew when you started it off that at some
point you would either want to just let

it run on its own or potentially find
an exit and then go do another thing.

Did you do anything in
particular consciously to

prepare your startup for an exit?

Tim Grassin: Yep.

There's a great book that I
read, relatively early on.

It's called built to
sell by John Warrillow.

Does it ring a bell?

It's a great book.

And after reading that book, I
figured out that every process can be

automated, either fully automated or
make someone the piece of the automation

so that they can run it for you.

And the idea was that if a business runs
by itself and you don't get involved,

whether it's in sales or management
or anything, it's a sellable business

because it becomes very easy to prove to
the buyer that they're buying cashflow.

They're not buying you or
your brand equity, or at least

your personal brand equity.

And so in the back of my mind, I
said, look, if I build it that way,

at least I know that I can always exit
it and it'll be very easy to prove.

And that actually just happened to be
the case when we got approached for

candy banners by one of our clients who
wanted to internalize production of their

digital assets, they said, look, we're
going to have to keep you on board, we're

going to have to do an earn-out, etc.

Well, me and my partner, we said, well.

We don't want to do that and we can prove
to you that we don't need to do that.

And it was shocking to them
because it's just such a

standard thing to do it or not.

Right.

So people don't expect you to say no,
but then we showed them that the last

six months before they reached out to
us, we had not touched the business.

We did a bit of accounting, basic stuff
that, you know, bookkeeping is something

we could have replaced ourselves on,
but we just did it because we wanted to.

But everything else from client
management to new client acquisition,

to all operations, we had not
touched it one bit for six months.

And when we were able to prove that by
emails, by chat logs, all of that good

stuff, and also, employee interviews,
they realized that indeed we, like the

earn now is just, a way to punish us
almost for creating something good.

And instead there was
like a monetary earn out.

So like we had to reach our targets
to unlock a trench of the payout,

but everything else was pretty basic.

No work

Prateek Panda: I want to ask

Tim Grassin: needed.

.
Prateek Panda: When should you, start
approaching an exit sort of plan?

Because a lot of times founders
get emotionally attached.

And I used to be one of those in my early
twenties with my first couple of startups.

I was very emotionally attached and
wouldn't be able to identify the best

moment to, explore an exit option.

And one of my mentors once said
that, and this might sound harsh to

a lot of people that nobody wants
to marry a terminally ill patient.

So, that's the thing with startups.

A lot of times, founders would think
about an exit when they're doing

terribly, not able to raise money.

It's a sinking ship and you try
to scramble to find a buyer.

And it's the worst negotiation
place that you can be in.

Is there anything for all the
listeners here, whether they're

running B2B product companies or
services businesses, when is a good

time to start thinking about, an exit.

And does it make sense to keep yourself
emotionally detached to the transaction?

Tim Grassin: Yeah, I think timing and exit
is like timing the stock market, right?

It's very hard to do.

And we always hear about people who
successfully did it, but it doesn't

mean that they did it intentionally.

I think they were just lucky.

I think timing and exit, like you said,
it has to be done based on momentum.

When things are going really, really
well, you can negotiate a better multiple.

It's kind of like fundraising.

You, Rarely fundraise when
things are going badly, right?

It's going to be hard
to negotiate good terms.

If you're tanking, you have two months
runway and you desperately need the money.

Otherwise you're folding shop.

So I think it's the same thing.

And I think you have to consider
two things in a liquidity event.

Like first of all, there's
going to be the exit.

Sure.

But before that you could also look at
secondaries and a lot of founders omit the

idea that secondaries are a powerful way

..
To get some cash flow while
still operating the business

and de-risking yourself.

And for me, selling the business
just happened at a good time where

things were going well and I got
offered an opportunity, but I always

regretted selling those two businesses
because while the first business

I sold after I sold it, it went on
to grow by tenfold in five years.

And it was an insanely profitable,
probably 50 percent EBITDA business.

Kind of stung that I had to sell it.

And that one was a sale that
just happened out of necessity.

The second one, just as a
great opportunity, a client

comes to knock on your door.

Like if you want cash and you want to
do something else, that's a great idea.

If you're building a business for the
only purpose of selling, then you should

always brace yourselves for a sale.

Like, don't say, Hey, I'm only
selling in 10 years because

maybe the market will collapse.

And you know how AI wiped
out a lot of startups.

They weren't ready for that.

And if their only goal was to wait
10 years before they sold, they might

probably got wiped out and there's
nothing there to make money on.

So I would say always be ready to
sell and just make sure that You don't

wait for a negative inflection point
before you start considering a sale.

When things are going up, and things
are going well, probably after

series A, series B, already start
considering that a sale is on the table.

And just make sure your company is
prepared for a sale, so that everything is

clean, your data room is always up to date
because sales can happen very fast, right?

When you have a corporate buyer or
another startup trying to acquire you,

they move fairly fast and it's better
to be ready for that than for them

to shop around for your competitor.

Prateek Panda: Yeah, I think, that
last point is extremely valuable

and was my experience as well.

Having clean books and a clean
data room is supremely valuable in

helping build confidence in the sale
and also helping it move faster.

So I'm going to shift this conversation
to the complete start of the spectrum.

So we talked about exit.

Thank you.

Let's talk a little bit about MVPs because
you also help a lot of startups figure

out MVPs and how to test their products.

What's something that you see as
a common mistake a lot of founders

make when they're in their MVP stage
and something that people can do

to maybe not make the same mistake?

Tim Grassin: Yeah.

So

Prateek Panda: mistakes

Tim Grassin: MVP is a fluid concept
for me because I've been told that

I'm too early stage, even in my MVP.

So, I talk about validators more
than MVPs and I like to validate my

ideas through even single feature
or like fake Fake apps or fake fake

products to validate the interest of
people in your product or services.

MVPs, I think the main mistake people
make is that they don't really know

how to define an MVP and even if it's
in the title, minimum viable product,

everyone just wants to throw more at it
because they feel like the minimum viable

product still requires several features.

And so they don't really spend
enough time thinking about the

essence of what they're selling.

Like what is the one value added service
or feature that you're building that

Might be interesting for your ICP.

So I would say that's the biggest mistake
and to alleviate that mistake that's

why I prefer validators rather than MVPs
because validators you literally have one

hypothesis and you create an experiment
to validate that hypothesis and to

illustrate that point I can tell you that
when we started TendoPay We wanted to

validate one hypothesis after the other.

And so our idea when we started was
that the Philippines had a rising e

commerce market, and it was very new
because, players like Lazada, Shopee

wasn't even around when we started.

So Lazada was really dominating
and they had created a copycat

of Amazon for Southeast Asia.

And that was booming because
there was really no other e

commerce back in the days.

This is not even that far long ago.

This is like seven years ago.

So it tells you how behind
Southeast Asia was, right?

And to further illustrate how behind they
were, the credit card rate of penetration

in Southeast Asia was about 5%.

And in the Philippines was
probably lower than that.

And that meant that to pay for their
shopping on Lazada, people have to pay

with cash on delivery, meaning they
would have to wait for the delivery guy

to show up at their door, give them an
exact change, get like a proof of payment.

And I mean, the process was just
outrageous coming from North America

where everything is paid by Apple
pay or Google pay or credit card.

And so when we realized that we realized
there was a big gap in the payment space.

And Buy Now Pay Later was sort of growing
in North America, Europe, Australia.

And so we decided that a buy not pay
later option would be a good idea for

the Philippines and so what we wanted
to test was if someone lands on an e

commerce page and they see the option
to buy a product full price or pay an

installment for a slightly higher price,
would they choose the installments?

So we created a fake landing page for
a product or fake product page, product

display page for a pair of sneakers.

And in this page, we displayed the buy
now button and then the buy now pay

later, but, and the idea was, okay, we
want to validate if they would click on

one or the other, boom, we ran some ads
90 percent or more clicked buy now pay

later, that was the first hypothesis.

The second one was, okay, now we
want to test how much information

they'd be willing to give us.

In order to be approved for
a buy now pay later account.

So we created a type form and we started
asking all sorts of crazy questions

about their employment, background
checks, how much they made, what

their relatives information was like.

We wanted to test how
far they would take you.

We ran several experiments, but
essentially that's the second

validator is people were willing
to give a ton of information about

themselves to get approved for that.

And you get the idea, right?

We would create an experiment.

We had a hypothesis, we create an
experiment and we would validate.

And that's where the debate has been
with several people that I've had.

This is not an MVP in the sense
that you don't have a full product

that people would be willing to
pay by your building up towards it.

And you don't have to build that whole
MVP to test out all these things.

Like we could have built an MVP and
then no one wanted it because we

didn't validate all that information.

So, to lead to the MVP, you need
to build all these validation

or hypothesis validations, guide
what your MVP will look like.

Eventually we did build an MVP, which
was completely manual where we had a

plugin, like a, it was a WooCommerce
plugin and a few stores added it and

what it would display exactly those two
buttons on your product display page.

And run you through like a type form.

We would collect the information.

We would manually approve you and
we would send the money to the

store if we approved that account.

So the payment was made and the
person would receive their item.

That was the MVP.

It was that very low to like very
low code, all manual processes,

but at least there was a product.

Someone was getting value out
of it and they were willing to

pay us because we would charge
interest on hope that made sense

Prateek Panda: Yeah, I think
that makes a lot of sense.

I like the approach of validators
because Couple of takeaways there.

One is, as you said, MVP, what
is MVP for you is hard to define.

And I've seen numerous founders,
especially amazingly smart technical

founders, who can get into this
zone of continuing to build an MVP.

And you never get the product out.

Tim Grassin: Because they love building.

They hide behind building.

It's comfortable, you know?

Prateek Panda: So I think that and
then the other take away from this is

really doing those fast experiments
and creating one hypothesis at

a time and just moving quickly.

A lot of times we've, made this mistake.

I've done it too, where we're trying to
test too many things at the same time.

And it's hard to derive results because
you don't know what exactly happened.

Tim Grassin: hundred percent...

Prateek Panda: So you run an
experiment without knowing, okay,

what do I derive out of this?

Tim Grassin: Mm hmm.

Prateek Panda: So I think, I love that.

Thank you so much for sharing it.

You've also talked a little bit
about challenges with being judged,

about your founder journey and
misrepresentation and things like that.

Right.

Can you tell a little bit more about that?

I know a lot of founders struggle
through that, but rarely does

anyone speak out loud about it.

One of the things I'm trying to do
with this podcast is lot of things

that are nice and exciting are
obviously visible on the outside.

More often than not, the founder
journey is pretty stressful

and, you see a lot of lows.

And it can be a lot of times
a fairly big emotional blow.

Have you experienced any of that?

What did you do to handle it?

Tim Grassin: I mean, I think we
both know that, the main pressure

comes from your family, right?

Uh, especially when you've studied
something that is as stable as finance

and, well, you, you told them and fed
it to them that you were going on this

corporate trajectory that was going to pay
well, be very stable, be well recognized,

and all of a sudden you say, hey, I'm
dropping all that and I'm going to start

a business that You struggle to explain to
your older parents what these businesses

are because they're all digital.

They don't really understand it as
much as, they try to make an effort

and they want to be part of your life.

You dumb it down and they
still don't get it fully.

And that's a frustration for both parties.

And I think because of this disconnect.

Parents are proud to talk about
their kids to their friends.

And if they can't really explain
what their kids do, it makes

it difficult for them to absorb
and to be comfortable with it.

And so between them not understanding
what you do, not being explained to

what you do to their friends, and
then them feeling like you're taking

a big risk on your life when all they
want for you is stability and comfort.

I think that's where the sort of deep
pressure comes in and not to mention

the financial pressure of, not having
a comfortable cushion or salary.

So I lived through that,
especially in my first business.

After the first business, they
understood that, okay, this

guy, Knows what he's doing.

Now he has a cushion to, to fall back on.

So they stopped worrying about
it, but definitely there was a

lot of pressure to begin with.

and then I think from the rest of
my acquaintances and friends, there

was not as much cause, they all
understand the concept of startups.

They all understand the concept
of being self employed, but

internally I do struggle still
for having never had a salary.

I mean, after my studies, like I did have
a finance job for a little while, like

right during my studies and right after,
but that was really student salary, right?

Like I'm talking about a
comfortable salary equal to my

15 year professional experience.

I've never had that.

And sometimes I look at, my friends
or peers who are getting like

multiple six-figure salaries plus
bonuses, plus this, plus that.

I'm like, You know, like I wish
I had that sometimes just the

comfort of someone just telling you,
Hey, let's do this job well done.

Here's your monthly massive salary.

And you know, let's do
it again next month.

For me, it's like, I'll take whatever
I need to live and the rest of my money

I make during liquidity events and I
also don't really touch that money.

It's all reinvested immediately.

So I never feel like a huge comfort
where I'm like, Hey, I'm making 50

K a month and I can spend it because
I'm getting it again next month.

I'm just like, no, I sold my business.

Everything's going into stocks
or real estate because that's

my cushion when I retire.

Cause I won't have retirement basically.

So it's a different mindset.

So internally and externally
there are pressures and you

have to be ready for that.

But just the excitement of doing
what I want every day and building

things that excite me is enough
to compensate for all that.

.
Mm-Hmm.

Prateek Panda: That is invaluable.

Really.

A friend of mine just yesterday,
we were talking, he's wanting to do

his first startup and he was asking
me, how do you just keep going?

And I was like, I think every
founder agrees that the journey

is treacherous to say the least,
but it's exciting to do what you

really want to do at your own will.

And if you're truly passionate about
it, you have a pretty good journey, even

if you experience a lot of shitty days.

Overall, you would
never regret doing that.

On the contrary, if you don't do it,
probably you would still regret it.

And when you shared your experience,
it reminded me of my B-school days.

One of the things, one of my academic
directors was asking me is, I used to

head the entrepreneurship committee and
my job was to encourage more students

to start businesses out of B-school.

Tim Grassin: Mm-Hmm.

Prateek Panda: I think in my batch, it
was maybe just me and in my batches,

I had maybe a couple of folks and my
director was asking me, why aren't

we able to encourage more students
to start their own businesses?

I was like, we get such fancy
jobs and high pay that that carrot

is just too difficult to avoid.

You come into a B-school program, take
a lot of debt that you have to pay

off, and at the end of the program
you're getting what a lot of people

would consider a dream job, that pays
really well, it'll take care of your

debt, give you a great lifestyle.

And it's really, really hard at that
point to take, to make a choice that,

Hey, I'm going to give this all up
to go figure out a startup journey.

So, the other thing that was relatable
to me was from your story, this thing

about convincing or getting some
approval from your parents, right?

And we all see that at some point and
having come from an Asian household,

it was expected to go down a
particular path and I didn't do that.

And, a hack that I found eventually
was, the shift happened when my parents

started to take me more seriously
is when I started to appear in, news

shows, television shows, newspapers.

It didn't mean anything to me, to
be honest, but suddenly my parents

started to think, Oh, he must be doing
something, for real because he's on TV.

And I kept saying that to a lot of my
founder friends eventually, that if

you feel stressed about this, do some
good PR, doesn't matter if it helps

your business or not, you would settle
this thing with your parents and they

would probably feel more confident
that you're onto something more real.

Tim Grassin: Love it.

That's smart.

Never did that, but that's a good idea.

Prateek Panda: Yeah.

As we wrap things up, any last comments
for, People who are listening, there's

B2B founders who are in this journey.

Any tips and advice from you having
done this for such a long time?

Tim Grassin: I think it's
important to have good peers, good

mentors, people to bounce ideas
on, what I call sounding boards.

I never really had that many
when I was starting out.

So if you're listening and you
feel like you need someone to spar

with, feel free to reach out to me.

I'm more than happy to help at this
point in life, the whole idea behind

my podcast and even the next big wave
program I have, I don't charge a lot

because I want to be able to help people.

Rather than just make money.

And so just in general, if you just
want a sparring partner, someone

to talk to or a sounding board,
just feel free to reach out to me.

I'm always happy to give out free
help, and to have a quick discussion

with anyone, anyone who's a
founder B2B is more my specialty.

So I'll have more insights for you.

So yeah, feel free to reach
out to me too on LinkedIn.

I'm sure Prateek will share a link.

And yeah, always happy to chat.

Prateek Panda: Thank you so much, Tim,
for sharing all this amazing information.

Lots of helpful actionable
tips and advice.

It was a pleasure talking to you.

Tim Grassin: Well, thanks for having
me Prateek, really enjoyed it.

Prateek Panda: 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.

If you loved today's episode.

Then don't forget to subscribe to this
podcast and never miss an episode.

Be kind, be happy, challenge the norm.

I'll see you folks again for the next one.