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Dear Founders,
Builders, and
Bold
Dreamers,
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Meet Arjun
Mahadevan, the founder of Doola
— a platform that
enables anyone in
the world to
launch a U.S.
business, now
valued at over $100 million.
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His journey is
not defined by
privilege or
shortcuts, but by
relentless focus,
consistent
execution, and a
deep understanding
of what it truly
means to build
something from
scratch.
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Arjun’s story
offers powerful
lessons for every
startup founder
navigating
uncertainty:
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What it looks
like to fail
with a first
startup — and
still keep
building
How a
well-crafted
pitch can raise
$1 million in
just 2
minutes
Why storytelling
and building in
public are no
longer optional,
but essential
How mastering a
few
high-leverage
moves can unlock
exponential
growth
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To help distill
the lessons, we’ve
broken down
Arjun’s journey
into five
founder-first
sections, designed
to give you
clarity,
strategies, and
actionable
insights at every
stage of your
startup
path:
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Founder
Framework
— dive deeper into
the mindset and
operating system
behind Doola’s
$100M climb
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Master the
Move
— explore five
high-leverage
strategies any
founder can apply
to gain traction
and scale
smarter
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Pitch
Perfect
— analyze Doola’s
Series A pitch
deck to learn how
Arjun crafted a
compelling story
that closed
capital and built
conviction
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The
Founder’s
Edge
— watch the
interview with key
timestamps to see
how Arjun thinks,
moves, and makes
decisions in real
time
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Inside the
Playbook
— access a curated
vault of Arjun’s
pitch decks,
interviews, and
strategic insights
for further
study
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Arjun
Mahadevan’s
$100M Founder
Framework
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Imagine you're
standing on
stage.
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There are bright
lights, a 2-minute
timer ticking
down, and judges
from HubSpot
sitting in front
of you, deciding
whether or not to
give you $1 million.
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This is exactly
where Arjun
Mahadevan, founder of Doola, stood — and he walked off
with a $1
million check.
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❌ Not because
he was the
most polished
speaker. ❌ Not because
he had the
most complex
slides.
But because he
understood one
thing:
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“People
don’t
buy
from
businesses.
They
buy
from
people.”
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Founder
Reflection:
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Are
you
overthinking
your
pitch
or
product…
and
underestimating
how
you make
people
feel
when
they
experience
your
brand?
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From Failed
Startups to a
$100M
Business
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Before Doola,
Arjun tried (and
failed at) other
ideas.
A social fitness
app? Didn’t
work.
A video messaging
tool for remote
teams? Crashed — even after
getting into
Y
Combinator.
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But every failure
taught him
something.
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He didn’t
quit.
He rolled the
dice again.
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And with Doola,
he didn’t just
find a business
idea. He found asymmetric
upside
— tiny actions
that led to
massive
outcomes.
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“Startups
don’t
die
from
running
out
of
money.
They
die
when
the
founder
loses
motivation.”
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Founder
Check-In:
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Are
you
still
motivated?
If
not,
are
you
surrounded
by
chimps
(your
tribe)
or
stuck
in
a
bucket
full
of
crabs
who
keep
pulling
you
back?
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How He Built a
Founder Brand
That Fuels the
Business
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You don’t need to
be an
influencer.
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You need to be a documenter.
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Arjun started
small — batching
tweets on weekends
and repurposing
them to LinkedIn.
Over time, he
built a following of
880,000+
people
across social
platforms.
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The
outcome?
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“Your
personal
brand
is
not
fluff.
It’s
distribution,
trust,
and
hiring
—
rolled
into
one.”
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Think Like a
Founder:
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️♂️
Are
you
hiding
behind
your
product
or
building
in
public?
️
What’s
one
thing
you
could
share
today
about
your
journey?
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How He Uses AI,
Systems &
Delegation to
Scale
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Most founders are
stuck doing
low-leverage
tasks.
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Arjun made a
$3,000 decision:
outsource
everything about
company formation,
bookkeeping,
taxes, and
analytics — and
built that as a
service for
others.
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This gave
founders back
their time to build products,
land customers,
and grow
— not do
paperwork.
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“The
hardest
lesson
is
unlearning
the
belief
that
you
have
to
do
everything
yourself.”
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️ Founder Gut
Check:
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What’s
one
part
of
your
startup
you’re
still
doing
just
because
you
always
have?
️
What
could
happen
if
you
let
go
of
it?
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From LLC to
Long-Term
Growth
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The genius behind
Doola wasn’t just
helping people
incorporate.
That’s a one-time
transaction.
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The brilliance
was in asking
customers:
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“What
are
you
struggling
with
next?”
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The answer?
Bookkeeping. Taxes.
Analytics.
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So Arjun built
the back-office
engine
— a full suite of
services wrapped
in trust,
community, and
brand.
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Founder
Decision:
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Are
you
trying
to
scale
a
product…
or
are
you
solving
a
whole
problem
journey
for
your
customer?
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The Truth About
Success? Just
Keep Rolling.
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Arjun believes
success in
entrepreneurship
is like rolling a
100-sided
dice.
At first, you may
only have 1 green side
— and 99
reds.
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But every time
you roll, you
learn.
And every red
eventually turns
green.
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“The
greats
have
failed
more
times
than
most
people
have
even
tried.”
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✨
Final Takeaway:
Fortune Favors
the Bold
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If you’re a
startup founder,
solopreneur, or
small business
owner — here’s the
truth:
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You don’t need
the best
idea. ⏰
You don’t need
the perfect
timing.
You don’t even
need YC.
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You just need to take action.
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Because
a
bold
dumbass
beats
a
shy
genius
— every
single
time.
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5 Strategies to
Level Up as a
Founder
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Every founder
hits a moment
where they realize
—
This isn’t just
about building a
product.
It’s about
building yourself
into the kind of
person who can
navigate
uncertainty, lead
others, and create
leverage where
none exists.
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So how do you master your
move
— especially when
every day feels
like controlled
chaos?
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Here are 5
high-leverage
strategies
founders like
Arjun Mahadevan
have used to stay
sharp, move fast,
and build with
purpose.
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1️⃣ Default to
Action
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“Action
produces
information.
Overthinking
produces
doubt.”
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Start small, but
start now. If
you're unsure
whether an idea
will work, don’t
stew — ship.
Whether it's a
cold email, a
landing page, or a
pricing test, the
moment you act,
you start
learning.
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Micro-move:
Launch something
uncomfortably
early. Your next
big breakthrough
might look like a
scrappy tweet or a
clunky
prototype.
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2️⃣ Build in
Public
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“If
no
one
knows
what
you're
building,
you're
leaving
luck
on
the
table.”
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Share your
journey online.
Not to show off,
but to build
trust. To attract
early users,
collaborators, and
believers. The bar
is low — just 1%
of people post, so
showing up
consistently gives
you exponential
visibility.
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Micro-move: Post once a week
about what you’re
learning or
building.
Repurpose it
across LinkedIn
and X.
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3️⃣ Talk to Your
Users —
Weekly
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“Most
startup
problems
can
be
solved
by
talking
to
more
users.”
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Your product
roadmap doesn’t
come from your
head — it lives in
your customers’
frustrations,
wishes, and
workarounds. Doola
only grew because
Arjun listened
deeply and acted
fast.
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Micro-move:
Schedule 3
customer discovery
calls this week.
Don’t sell —
listen. Ask,
“What’s the most
frustrating part
of your
workflow?”
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4️⃣ Automate the
Back Office,
Focus on the
Frontline
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“Your
highest-leverage
work
lives
in
product,
sales,
and
vision
—
not
in
reconciling
Stripe
with
QuickBooks.”
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Successful
founders
ruthlessly protect
their time.
Delegate taxes,
bookkeeping,
admin, and
compliance to pros
so you can focus
on what moves the
needle.
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Micro-move:
Audit your week.
Circle the tasks
someone else could
do 80% as well.
Systemize or
outsource
them.
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5️⃣ Design for
Asymmetric
Upside
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“Some
moves
change
everything.
Focus
on
those.”
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Write the blog
post that brings
in 1,000
customers. Pitch
the podcast that
lands your first
investor. Say yes
to the 2-minute
pitch that turns
into $1 million.
Be biased toward
moves that cost
little — but could
return
massively.
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Micro-move: Identify one
asymmetric move
you can make this
week — then go all
in.
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Doola’s Series
A Pitch Deck
Breakdown
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This pitch deck
is a clear example
of how simplicity,
storytelling, and
structure can win
over investors. It
shows how Arjun
Mahadevan
positioned Doola’s
mission,
communicated
traction, and
framed a
compelling vision
for the future.
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Founders can use
it as a reference
to craft stronger
narratives,
sharpen their
decks, and raise
with clarity and
confidence.
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Slide 1:
Title Slide:
Aspirational
one-liner
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Slide 2: Social Proof:
Show our
fundraising
history
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Slide 3: Problem: What
is the world
today / status
quo?
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Slide 4: Solution:
What does the
world look like
with doola?
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Slide 5-9: Vision: What
is our master
plan (multiple
slides)?
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Slide 10: Monetization:
How do we make
money?
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Slide 11: TAM: What is
the total
addressable
market?
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Slide 12:
Differentiator:
What makes us
different?
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Slide 13: Team: Why is
this team
special?
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Slide 14: Thank You:
Outro slide with
contact info
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Doola’s Series A
deck shows that
the most effective
pitches are the
ones that resonate
with clarity and
conviction. It
reflects a strong
understanding of
the founder
journey, a focused
vision, and the
ability to inspire
investor belief.
For any founder
preparing to
raise, this serves
as a valuable
example of how to
combine
storytelling with
real
traction.
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Learn Directly
from the
Source
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Why just read
about a founder’s
journey when you
can experience it
firsthand?
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The Founder’s
Edge
section is
designed to bring
startup wisdom
straight from the
source — in this
case, from Arjun
Mahadevan’s
powerful
conversation
that breaks down
how he built Doola
from scratch,
raised $1M in 2
minutes, and
scaled to a $100M+
valuation.
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Watch the full
video
and follow along
with the Founder
Compass to go
beyond inspiration
— and gain real,
tactical insight
you can apply to
your startup
journey.
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I
Raised
$1
MILLION
In
2
MINUTES
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To help founders
extract the most
valuable lessons,
we’ve created a Founder
Compass
— a curated set of key moments and
timestamps
from the full
interview. These
moments spotlight
Arjun’s mindset,
strategy, pivots,
and the systems he
used to win.
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Don’t miss: Founder Compass
– Key Moments
with
Timestamps
right below.
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⏱️
Timestamp
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Key
Insight
|
What’s In
It for
Founders?
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0:00
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Arjun
introduces
how he
helped
over
10,000
startups
with
Doola.
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Sets the
tone: From
zero to
$100M with
tactical
insights.
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1:00
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How he
raised $1M
in 2
minutes
from
HubSpot.
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Pitching
secrets
revealed —
body
language,
tone,
simple
slides.
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2:30
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The
"KISS"
pitch
method and
Albert
Mehrabian's
93%
non-verbal
rule.
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Learn how
to win
pitches
before
you even
speak.
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4:50
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Building
a founder
brand on
social:
“People
buy from
people.”
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Why
content ≠
fluff,
it’s
distribution
and
trust.
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6:40
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The shift
from
product
obsession
to
purpose:
“From
negative
one to
zero.”
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Reframe
your
founder
journey.
Start
before
product-market
fit.
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7:50
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Why Doola
niched
down into
e-commerce
and how
they
picked
their
focus.
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Learn to boil a
spoon
before
boiling
the
ocean.
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10:00
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Why
analytics
is a daily
founder
habit:
“You can't
manage
what you
don't
measure.”
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Set up
insights
that are
too
obvious to
ignore.
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11:50
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"Untouchable
truths":
hire slow,
fire fast,
niche
down.
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Learn
what you only
discover
the hard
way.
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12:50
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Ignore
the crabs:
“People
will try
to pull
you
down.”
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Motivation
to keep
rolling
despite
judgment.
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14:40
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How to
use
customer
interviews
to solve any
business
problem.
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Actionable
customer
development
strategy.
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17:00
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Does
every
founder
need YC or
On Deck?
“No. You
just need
action.”
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Reassurance
for
bootstrapped
or
rejected
founders.
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21:00
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How he
knew it
was time
to pivot
during
YC.
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When your
product
isn’t the
solution
users are
willing to
pay
for.
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22:45
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The $0
lesson:
Always ask
customers
to pay
upfront.
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Pre-sell
before you
build.
Save
months of
dev
time.
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27:00
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Arjun’s
"Dice of
Entrepreneurship"
analogy.
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Brilliant
metaphor
on
perseverance
and
compounding.
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31:00
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Asymmetric
upside:
Examples
that
matter
(tweets,
meetups,
DMs).
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How to
maximize
return
from tiny
bets.
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34:00
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The "3
C’s" of
content
strategy:
Customers,
Colleagues,
Capital.
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Why every
founder
needs a
personal
brand.
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37:00
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Arjun’s
content
system:
Weekend
batching +
repurposing.
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Build a
content
engine
without
burning
out.
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41:00
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Turning
one-time
users into
long-term
clients
through
services
like
bookkeeping.
|
Add
layers of
recurring
revenue
from
founder
pain
points.
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44:00
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Mistake:
Doola
built a
website
builder no
one
used.
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Learn when
not to
build. Product
vs.
platform
discipline.
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47:00
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LLC vs.
C-Corp +
State
selection
for US and
international
founders.
|
Straightforward
legal
strategy —
skip the
confusion.
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49:00
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Why
30–40% of
businesses
churn
after
forming.
|
Real
talk: It’s
not just
money —
it’s
motivation
that kills
most.
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50:40
|
Why taxes
+
bookkeeping
aren’t
optional.
|
Focus on
growth,
outsource
the
grind.
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Learn from Arjun
Mahadevan’s
Winning Moves
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Here, we’ve
curated the most
insightful and
authentic
resources from
Arjun Mahadevan’s
journey —
including pitch
decks, podcast
clips, viral
posts, and
exclusive video
breakdowns.
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|
Whether you're
launching,
scaling, or
pivoting, we’ve
gathered
everything you
need to study the
mindset, strategy,
and systems behind
Doola’s rise to a
$100M+
company.
|
1. How Arjun
Mahadevan Raised
$1M in 2 Minutes
(Full
Interview)
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Watch on
YouTube
|
|
A
raw,
honest
conversation
with
Doola’s
founder
on
failure,
fundraising,
and
building
a
brand
that
sells.
|
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2. Doola on Y
Combinator: From
Idea to Global
Startup
Infrastructure
|
|
Explore on
YC
|
|
Discover
Doola’s
official
Y
Combinator
company
profile
—
insights
into
their
product,
mission,
and
traction.
|
|
|
3. How I Raised
$1M in 2 Minutes
– Visual
Breakdown
|
|
Read on
LinkedIn
|
|
Arjun
walks
through
the
strategy,
mindset,
and
visuals
that
made
his
million-dollar
pitch
unforgettable.
|
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4. The Revenue
Room: Learn
Sales Psychology
from First
Touch
|
|
Read on
First
Touch
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|
Build
your
revenue
muscle
by
understanding
modern
sales
motion,
buyer
psychology,
and
high-conversion
tactics.
|
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5. The Story
Behind Doola’s
$1M Pitch –
HubSpot's
Feature Video
|
|
Watch on
YouTube
|
|
HubSpot
Startup’s
official
feature
on
how
Doola
stood
out
and
won
the
$1M
pitch
competition.
|
|
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6. Arjun’s
Winning Pitch
Featured by
HubSpot for
Startups
|
|
Read the
Story
|
|
Learn
what
made
Arjun’s
pitch
irresistible
to
judges
—
and
how
you
can
replicate
the
formula.
|
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7. Doola’s
Series A Pitch
Deck Breakdown
(SlideShare)
|
|
View the
Deck
|
|
A
teardown
of
Doola’s
investor
pitch
deck
with
notes
on
what
works,
why
it
works,
and
how
to
learn
from
it.
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✅
Ready to Step
Into Action?
|
|
If this story lit
a spark, here’s
how you can fan it
into a
flame:
|
|
Follow us at
Foundevo
– where we share
real stories,
tactical insights,
and growth ideas
from founders like
Arjun every
week.
|
|
Subscribe to
our
newsletter
– and get
startup-ready tips
on building,
scaling, funding,
and
storytelling.
|
|
Share this with
one founder you
care about
– maybe they’re
waiting to roll
their next
green.
|
|
Join thousands of
founders getting
tactical insights,
pitch breakdowns,
and mindset shifts
from startup
operators who’ve
scaled from 0 to
$100M+. Subscribe
to Foundevo
and turn bold
ideas into real
momentum.
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