The full conversation.
Adrian
0:00
I
raised
that
on
the
strength
of
a
large
logo
co-development
partner
who
then
–
the
relationship
literally
dissolved
30
days
after
we
had
closed
that
half
a
million
dollars.
I
had
half
a
million
dollars
of
investors
that
had
invested
on
the
strength
of
this
logo
co-development,
and
it
literally
fell
apart
30
days
later.
Pablo
0:16
Welcome
to
the
product
Market
Fit
Show,
brought
to
you
by
Mistrial,
a
seed-stage
firm
based
in
Canada.
I'm
Pablo.
I'm
a
founder
turned
VC.
My
goal
is
to
help
early
stage
founders
like
you
find
product
market
fit.
So
today
we
have
Adrian,
the
founder
and
CEO
of
Athenian.
Athenian
provides
a
data
management
platform
for
legal
and
finance
teams.
They're
based
in
Calgary.
They've
raised
about
$50
million
and
have
over
a
hundred
employees.
Adrian,
it's
a
pleasure
to
have
you
on
the
show
today.
Adrian
0:46
Thanks.
Good
to
be
here,
Pablo.
Pablo
0:47
So
the
topic
of
today's
episode
is
how
to
sell
into
mid-market.
I
think
there's,
in
the
world
of
B2B
SaaS
startups
a
kind
of
sweet
spot
space,
right?
People
oftentimes
don't
like
selling
enterprise
because
it's
too
slow,
it's
too
chunky,
and
SMBs
oftentimes
don't
really
have
the
structure
and
size
and
capital
to
be
meaningful
customers.
So
this
mid-market
tends
to
be
a
sweet
spot
for
many.
I'm
excited
to
dive
into
that
with
you.
Maybe
as
a
starting
point,
we
can
kind
of
go
back
a
little
bit
and
just
talk
about
how
you
came
up
with
the
idea
itself.
Adrian
1:27
So
The Idea that Birthed Athennian
Adrian
1:28
we're
going
back
to
like
2016.
I
was
a
lawyer
at
a
large
corporate
law
firm
in
Calgary.
I'm
originally
from
the
Toronto
area,
so
I
moved
to
Calgary
for
that.
What
surprised
and
shocked
me
when
I
started
working
as
a
lawyer
was
just
how
hard
it
was
for
companies
to
provide
basic
information
about
their
entities
when
we
were
trying
to
do
a
transaction.
So
any
business
of
any
material
size,
once
you
kind
of
get
past
SMB,
a
company
is
more
than
one
entity.
That's
typically
a
handful
or
more,
corporations,
limited
partnerships
all
stitched
together
into
some
type
of
corporate
structure.
We
were
up
all
night
trying
to
figure
out
what
the
formal
legal
name
of
certain
entities
are.
Companies
just
don't
have
that
data
internally.
It
got
recorded
on
a
spreadsheet
one
day,
and
it's
being
colloquial
and
abbreviated
so
many
times.
When
you're
trying
to
transact
and
do
formal
transactions,
it's
important
that
you
get
the
accurate
legal
data
point.
Even
basic
things
like
just
what
the
entity's
name
is
is
really
hard
for
organizations
to
manage.
When
you
get
into
more
complex
stuff
like
the
ownership
details,
the
control
details,
the
tax
details,
international
presence
details,
it
just
goes
downhill
from
there.
I
really
wanted
to
understand
why
this
problem
was
so
bad,
why
it
was
so
hard
for
tax,
finance
and
legal
professionals
who
are
all
very
smart
and
have
lots
of
resources
to
keep
all
this
organized.
We
really
just
discovered
it
was
really
just
a
data
management
issue.
The
systems
to
manage
all
this
information
were
binders
on
shelves
and
then
just
tons
of
old
legacy
software
spreadsheets.
It
was
just
a
lot
of
pre-internet
type
of
stuff.
The
problem
is
everybody
needs
this
information,
and
so
it
just
gets
highly
fragmented
and
just
standard
kind
of
business
workflow,
business
data
management
type
of
problem.
In
about
2017,
we
started
building
into
this
space
and
fast-forward,
here
we
are.
Pablo
3:38
Just
to
be
clear,
who
mainly
experiences
the
problem?
Is
it
the
legal
firm,
like
a
Gallings
or
something
like
that,
or
is
it
the
actual
client,
the
corporation?
Adrian
3:46
Yeah,
so
it's
everybody.
Everybody
experiences
it
in
a
little
bit
of
a
different
way.
The
way
to
think
about
it
that
is
maybe
more
a
little
bitaccessible
is
if
you're
bookkeeping
or
accounting
records
were
just
a
mess,
and
the
data
wasn't
accurate
and
you
have
a
spreadsheet
with
numbers
in
it,
but
you
have
no
receipts
or
contracts
to
back
–
to
evidence
any
of
that,
that's
a
problem
internally
for
the
company
in
various
departments.
It's
a
problem
for
the
accountant;
it's
a
problem
for
tax
advisors.
It's
a
problem
for
the
CRA
or
the
IRS,
who's
ever
your
tax
authority.
That's
a
really
good
analogy
to
the
type
of
problem
that
we
have
here.
To
kind
ofpaint
a
picture,
when
–
the
ah-ha
moment
for
me,
we
had
to
do
due
diligence
on
a
company
that's
now
actually
a
customer
with
Athenian,
when
I
was
back
to
the
law
firm.
On
their
legal
structure,
we
went
into
a
boardroom
and
there
were
500
binders
in
banker's
boxes
around
this
boardroom.
We
had
to
flip
through
every
single
page
of
these
500
binders
to
find
signature
–
documents
that
weren't
signed
by
the
board
of
directors
confirming
that
shareholders
had
approved
all
the
financial
statements
every
year.
Each
binder
was
an
entity
in
this
company's
corporate
structure.
It's
constant
rediscovery
and
re-validation
of
data
that
already
exists
just
so
you
can
take
–
execute
a
transaction
or
make
some
decision.
That's
felt
by
internal
legal
tax
finance
teams;
it's
felt
by
law
firms,
accounting
firms,
audit
and
tax
advisory,
anybody
who's
been
in
M&A,
banking
typically
experiences
this
problem.
Pablo
5:28
So
that's
helpful
in
terms
of
the
problem.
So
I
guess
my
big
question
is
what
do
you
do
at
that
point?
I
mean,
you're
a
lawyer,
right?
Do
you
find
someone
and
you
start
building
this?
The
other
side
to
that
same
question
is
the
customers
for
this,
like
you
said,
are
the
more
complicated
–
the
bigger
the
better
kind
of
thing.
I
mean,
the
small
SMB
doesn't
really
have
this
problem.
It's
more
like
the
legal
firms
and
the
bigger
corps.
So
where
do
you
go
from
here
to
just
get
started
on
solving
this?
Adrian
5:54
Yeah,
Focus Groups and Gaining Traction
Adrian
5:55
so
what
I
did
was
–
and
I
do
think
this
is
one
of
the
decisions
that
–
one
of
the
best
decisions
we
made
was
I
realized
that
this
is
not
a
problem.
The
management
of
this
data
is
not
something
that
lawyers
or
attorneys
deal
with
on
a
day-to-day
basis.
It's
what
paralegals
do.
I
wasn't
a
paralegal.
I
was
a
corporate
lawyer
at
the
time.
The
first
thing
I
did
was
I
started
to
talk
to
tons
and
tons
of
paralegals.
Pablo
6:22
Sorry,
let's
dive
into
that.
I
think
that's
a
little
important.
How
did
you
do
that?
How
many
paralegals
are
we
talking
about
and
did
you
just
cold
email
a
bunch
or
was
it
kind
of
in
your
network?
How
did
you
structure
that?
Adrian
6:30
I
cold
emailed.
Yeah,
so
I
cold
emailed.
We
we
did
city
tours.
So
we
went
to
Toronto,
we
went
to
Vancouver,
we
went
to
Chicago,
and
we
literally
emailed
as
many
paralegals
as
we
could.
When
we
got
a
law
firm,
we
got
one
of
them
to
give
us
their
boardroom
and
we
literally
sat
down
with
them
for
three
hours
and
just
had
10
or
15
paralegals
in
a
room
and
just
listening,
just
talk
and
just
try.
Pablo
7:02
Oh,
wow,
so
it's
like
a
focus
group.
Adrian
7:03
Yeah,
totally,
just
focus
groups,
right?
I
mean,
a
lot
of
those
people
ended
up
becoming
our
first
customers
that
created
a
lot
of
commercial
momentum
for
us.
All
those
ten
people
went
and
talked
to
five
friends
that
are
also
paralegals
and
said,
listen,
I
think
these
guys
are
going
to
try
to
solve
this
problem.
We
met
with
them,
et
cetera
and
you
just
started
to
build
that
commercial
momentum
around
we
are
a
team
trying
this.
We
don't
have
a
solution
today,
but
we
are
trying
to
solve
this
problem,
and
you
started
to
capture
some
of
that
attention.
Pablo
7:32
On
those
focus
groups,
how
did
you
structure
it?
Was
it
very
open-ended,
hey,
what
are
your
problems,
high
level
da-da-da?
Or
was
it
already
kind
of
centered
on
this
is
a
problem;
how
do
you
solve
it
today,
and
kind
of
a
little
bit
more
leading?
Adrian
7:44
We
Co-Development Partners
Adrian
7:45
had
a
series
of
meetings
and
then
we
would
meet
with
people
one
on
one.
In
those
formats,
it's
hard
to
get
really
deep
into
the
details.
You're
trying
to
get
variety.
I
mean,
really,
the
outcome
we
were
looking
for
is
can
we
get
ten
people
to
align
on
the
problem
and
how
to
describe
the
problem?
That'll
chew
up
two
hours
really
quickly.
Then
everybody's
tired
during
the
meeting.
What
we
did
to
get
in
the
details
is
we
found
–
through
that
process,
we
found
some
early,
very,
very,
very
early
customers
that
we
called
co-development
partners.
These
were
some
larger
law
firms.
Some
of
them
are
customers
today;
some
of
them
are
not
and
they
really
wanted
to
solve
the
problem.
What
a
lot
of
them
did
was
they
really
unlocked
a
ton
of
resources
for
us.
So
they
gave
us
paralegals
that
–
and
this
is
a
little
bit
technical
or
how
law
firms
or
fresh
services
firms
work,
but
these
people
have
to
bill
hours.
They
have
to
account
for
the
hours
in
their
day.
Anybody
that
understands
this
world
will
realize
how
important
what
this
was
for
us.
The
firms
gave
some
of
these
paralegals
matter
numbers
to
build
their
time
to
so
it
was
like
a
matter
number
you
assigned
to
a
client.
We
literally
sat
down
and
deconstructed
the
existing
legacy
tools
they
were
using
screen
by
screen
by
screen.
We
probably
sat
down
with
paralegals
that
were
billing
their
time
into
this
project
for,
I
don't
know,
probably
four
or
five
months.
They
would
walk
us
through
their
–
they
would
walk
us
through
their
legacy
software.
We
would
screenshot
every
page
and
they
would
narrate
to
us
what
they
were
doing
in
each
of
these
screens
and
giving
us
the
business
context
and
jobs
to
be
done
framework
and
stuff
like
that.
We
really
methodically
essentially
tore
down
status
quo
to
really
understand,
and
that
was
super
key
for
us
to
understand
the
scope
of
what
we
needed
to
build.
What
we
were
going
up
against
was
it's
about
–
the
market's
like
50/50
Brownfield
and
spreadsheets
where
Brownfield
is
legacy,
really
old
legacy
stuff
that
you
have
to
rip
and
replace
out
of
the
market.
It
was
important
that
we
understood
how
the
work
was
done.
There's
a
lot
of
wisdom
built
in
legacy
systems.
People
dismiss
them
as
old
and
clunky.
At
the
time,
they
weren't,
and
at
the
time,
someone
went
through
a
product
process
over
years
and
years
and
years
to
build
something,
and
there's
tons
of
wisdom
in
those
legacy
systems.
We
tried
to
extract
as
much
wisdom
as
we
could
out
of
both
the
system
and
also
how
the
users
were
using
it.
Pablo
10:16
I
think
there's
also
tons
of
wisdom
in
just
the
amount
of
time
you
devoted
what
you'd
call
customer
discovery
or
prom
validation.
You
were
already
a
lawyer.
I
get
you
weren't
a
paralegal,
but
you
were
close
enough
to
it
that
a
lot
of
people
might
have,
in
your
shoes,
just
started
building
and
kind
of
made
a
few
assumptions,
maybe
spoke
to
five
or
six
paralegals
and
showed
them
product
demos
and
gone
from
there.
You
went
really
deep.
How
important
was
that,
do
you
think,
to
the
ultimate
success
that
your
company
has?
Adrian
10:44
Oh,
critical.
Customer Discovery is Critical
Adrian
10:45
We
have
some
competitors
today
that
had
a
very
similar
origin
story
to
me
where
corporate
lawyers
observe
the
problem.
They
missed
that
step
of
okay,
we've
got
to
sit
down
and
spend
six
months
with
the
primary
users
of
this
product
and
tear
down
their
day-to-day
at
a
screen-by-screen,
button-by-button
level,
and
understand
the
story
and
the
business
context
behind
every
action
they
take
so
we
can
get
the
full
scope
and
prioritize
of
how
we
build
this.
We
have
competitors
that
miss
that
step
and
they
built
it
with
the
bias
of
how
they
look
at
the
problem
and
you
have
this
huge
disconnect.
This
product's
being
built
from
the
perspective
of
a
lawyer,
but
you
got
paralegals
have
to
use
it.
Creates
an
enormous
disconnect,
and
then
you
obviously
struggle
from
there,
right?
It
was
super
critical
for
us.
It
allowed
us
to
get
–
just
running
the
process
and
showing
those
early
customers
the
work
we
put
in,
that
was
my
sales
pitch.
I
literally
brought
up
those
Visio
charts,
which
was
just
like
a
mirrorboard
type
of
thing.
That
was
my
sales
pitch
for
the
first
year.
I
sat
down
with
prospects
in
a
boardroom.
This
is
obviously
pre-COVID.
You're
pounding
pavement.
I
put
that
up
on
a
mirrorboard
or
Visioat
the
time
and
I
pitched
to
them,
I
understand
this
problem.
This
is
the
work
I've
put
in.
That
immediately
establishes
credibility
with
these
users
and
with
these
buyers
that
you
understand
what
you're
talking
about.
Wen
you're
super
early
stage,
you
signal
no
credibility
at
all,
right?
You're
a
couple
people.
At
the
time,
we
didn't
even
have
an
office.
You're
trying
to
sell
to
these
bigger
organizations
and
you
have
to
establish
credibility.
That
was
one
of
the
ways
that
we
did
that,
and
it
was
really
effective.
Pablo
12:33
Did
you
just
–
you
started
these
focus
groups.
You
went
out
to
these
paralegals
to
learn.
It
ended
up
getting
you
customers
who
pay
these
paralegals
to
help
you
build
the
product.
Did
you
set
out
to
get
those
co-development
partners
or
was
that
basically
organic
and
it
just
kind
of
started
coming
to
you
as
you
went
through
this
process?
Adrian
12:50
Yeah,
I
mean,
it
started
coming
to
us.
I
think
probably
what
happened
was
when
we
realized
the
scope
of
this,
we
knew
in
order
to
get
funding,
we
needed
to
get
some
commitment
from
these
customers,
cash
commitments.
Our
first
iteration
of
our
first
customers,
they
were
contracts
with
deposits,
but
the
balance
was
due
on
delivery
of
the
product.
When
you're
selling
into
mid-market
or
enterprise,
that's
super
high
risk
because
the
definition
–
they
can
just
extend
delivery
until
they
get
every
single
button
they
want,
which
obviously
creates
a
lot
of
risk
for
you.
Mitigating Unreal Expectations
Pablo
13:31
The
way
I
think
about
it
is
if
you
co-develop,
the
upside
is
you
get
a
lot
of
information
and
a
lot
of
feedback.
I
think
the
downside
is
you
risk
turning
your
customers
into
product
managers,
right?
There's
a
reason
they're
not
building
software.
How
did
you
balance
that
and
what
were
some
of
the
issues
that
came
up?
Adrian
13:46
It
was
super
hard.
We
had
customers
that
had
unreal
expectations.
We
had
customers,
they
wanted
us
to
commit
more
than
they
were
prepared
to
commit
in
terms
of
they
wanted
us
to
build
all
this
stuff,
but
they
didn't
want
to
put
down
another
50
grand
or
a
hundred
grand.
Investors
don't
wanna
fund
that.
You're
constantly
trying
to
–
you're
kind
of
caught
between
three
tension
points
of
customer,
team
and
investors
because
you're
also
running
your
team
really
hard
during
this
period
of
time,
right?
There's
tons
of
pressure,
there's
tight
timelines,
et
cetera.
Yeah,
I
mean,
the
customers
end
up
wanting
to
become
product
managers
and
we
had
to
fire
a
bunch
of
those
customers.
We
had
to
walk
away
from
the
relationships
and
we
said,
listen,
this
doesn't
make
sense.
You're
asking
us
to
build
stuff
that
we
don't
think
the
broader
market
wants.
This
is
too
specific
to
you
and
even
at
an
early
stage,
you're
trying
to
learn
from
them,
but
you're
also
trying
to
teach
them
at
the
same
time.
Sometimes
we
found
–
we
were
lucky
to
find
two
customers
where
we
could
effectively
create
that
cycle.
I
think
it
was
also
just
risk
tolerance
in
the
customer,
right?
The
one
thing
that
I
realized
is
if
you
want
to
do
this
co-development
process
with
mid-market
or
enterprise,
you
have
to
find
people
in
those
organizations
that
are
willing
to
take
a
lot
of
risk.
I
didn't
realize
this
until
I
think
a
couple
years
later,
but
these
people,
these
director
of
paralegal
was
typically
their
title,
they
were
putting
their
necks
on
the
line.
They
were
prepared
to
get
fired
if
this
didn't
work
out
because
that's
how
big
organizations
work,
right?
You
have
a
failed
IT
project.
You
spent
a
bunch
of
money.
A
couple
people
quit
because
they
got
burned
out.
You
get
fired,
right?
I
didn't
appreciate
until
a
couple
years
later
how
much
risk
that
they
were
taking
at
the
time,
and
I
do
now.
Yeah,
I
mean,
this
is
the
stuff.
I
mean,
we
were
very
fortunate.
We
had
four
and
two.
Two
we
cut
paths
with
and
the
other
two
we
kept
working
with.
I
do
think
that
you
do
need
to
have
multiple
and
it's
more
work
because
you
have
more
projects
you're
trying
to
manage,
but
it
helps
you
manage
the
risk.
Pablo
15:53
That
makes
total
sense.
These
are
all
large
customers
that
you're
working
with.
You've
got
four
of
them
on
the
go.
Back
then,
were
you
bootstrapped
or
had
you
already
raised
some
money?
Adrian
16:04
So
we
raised
a
couple
hundred
grand
on
day
one,
just
from
–
I
think
it
was
$165,000,
which
in
2017
actually
bought
something.
W
used
that
to
kind
of
fund,
I
would
say,
the
first
–
like
it
was
just
a
–
it
was
a
small
group
of
us.
We
used
that
to
kind
of
fund
really
early
market
analysis,
really
early
conversations,
things
like
that.
Then
we
had
some
evidence
that
okay,
we
think
there's
a
market
here,
and
we
raised
half
a
million
dollars.
Then
we
started
the
co-development
stuff.
When
it
got
time
to
actually,
okay
we
have
a
product,
we
–
these
contracts
are
starting
to
produce
some
cash,
customers
are
starting
to
pay
deposit
invoices,
et
cetera.
Then
we
raised
a
$2
million
seed.
Timing
that
was
was
–
it's
really
like
threading
a
needle.
I
remember
on
our
half
a
million
dollar
seed,
we
–
or
I
guess
that
would've
been
a
pre-seed,
I
raised
that
on
the
strength
of
a
large
logo
co-development
partner
who
then
–
the
relationship
literally
dissolved
30
days
after
we
had
closed
that
half
a
million
dollars.
I
had
half
a
million
dollars
of
investors
that
had
invested
on
the
strength
of
this
logo
co-development
and
it
literally
fell
apart
30
days
later.
Pablo
17:22
Was
that
tough
to
manage
afterwards?
Was
there
some
outcry
or
not
really?
Adrian
17:27
Well,
I
mean,
you
just
need
to
figure
it
out,
right?
So
I
just
went
and
I
just
found
an
equivalent
amount
of
revenue
opportunity
and
I
backfilled
and
you
just
have
to
figure
it
out.
Timing
the
capital
to
the
co-development
milestones
to
the
customer
commitments,
et
cetera,
was
super
important,
obviously,
because
you
have
to
–
you're
burning
an
incredible
amount
of
money
to
do
this.
Pablo
17:51
How
did
you
–
what
were
the
conversations
like?
At
some
point
you
have
these
co-development
partners,
but
you
have
this
deposit
structure.
It's
not
ideal
and
you
decide
these
people
really
have
to
pay
if
they
want
to
be
customers.
That's
where,
if
I
understand
correctly,
two
of
them
churn.
What
were
those
conversations
like?
Can
you
give
us
some
of
the
details?
Adrian
18:07
Yeah,
I
How to get customers to pay
Adrian
18:08
mean,
the
conversations
at
the
time
were
very
–
I
don't
how
to
put
this.
They
were
like
–
they
were
not
very
sophisticated
conversations.
We
essentially
said
to
them
you
got
to
pay
a
deposit
because
we
don't
have
any
money
type
of
–
that
was
–
it
was
very
unsophisticated
at
the
time.
I
think
if
I
could
do
this
again,
I
think
what
I
would
say
is
something
along
the
lines
of
we're
both
taking
risk
here
and
there
and
we
need
cash
commitment
from
you
in
order
to
justify
us
to
take
the
risk
of
our
time
to
invest
in
this
area.
I
have
my
threshold
if
I
ever
do
this
again
would
be
–
I
would
not
start
cutting
a
line
of
code
unless
I
can
get
six-figure
order
form
deposits
on
the
basis
of
a
PowerPoint
deck.
If
I'm
unable
to
do
that,
I
either
have
not
identified
a
painful
enough
of
a
problem
for
the
customer
or
I
have
not
articulated
a
compelling
enough
solution
to
that
problem.
The
minute
you
start
this
process
and
you
start
learning,
and
building
spec,
and
writing
code,
you're
opening
the
biggest
can
of
worm
of
your
life
–
can
of
worms
of
your
life.
It
just
kind
of
spirals
into
five,
six
years
later
here
you
are.
You
really
need
to
extract
that
commitment
from
the
customer.
That's
really
your
evidence
that
this
is
a
serious
enough
problem.
Pablo
19:29
I
mean,
especially,
and
I
think
founders
often
forget
this.
The
larger
customers
spend
a
lot
of
money.
That's
the
simplest
way
to
put
it.
They
spend
a
lot
of
money
on
stuff.
I'm
not
going
to
go
say
a
hundred
K
is
a
drop
in
the
bucket.
It's
not,
but
at
the
same
time,
you're
not
the
only
thing
they're
spending
a
hundred
K
on.
If
they're
spending
a
hundred
K
over
here
and
over
there
and
over
there,
but
on
you,
they
won't
and
they
won't
even
spend
5K
or
10K
something's
wrong.
I's
not
like
the
next
feature's
gonna
get
them
over
the
night.
Adrian
19:55
Totally.
Yeah.
I
mean,
if
you're
talking
to
a
medium-sized
business,
which
let's
say
medium-sized
businesses,
I
don't
know,
is
over
250
employees.
For
them
to
spend
$25,000
on
a
deposit
is
not
a
lot
of
money.
If
it's
over
a
thousand
employees,
call
it
a
mid-market
organization.
A
hundred
thousand
dollars
and
it's
a
real
big
enterprise,
I'd
be
looking
for
mid-six-figure
commitments
from
them.
The
reason
is
–
and
I
think
this
is
what
you
don't
understand
is
as
a
first
time
founder
is
that
the
requirements
to
get
your
product
into
that
organization
and
get
cash
flowing
off
of
a
contract,
you
have
adoption,
you
have
cash,
you
have
payments
on
your
invoices
and
so
on,
you
have
that
cash
flow
cycle
starting,
it's
very
uncertain
because
the
total
requirements
of
the
organization
is
like
an
iceberg,
right?
What
they
tell
you
is
probably
30%
at
most
of
what
you
need
to
actually
build
to
get
that
cash
flowing.
That
60
to
70%
is
that
unspoken
requirement
of
assumptions.
They
just
assume
it's
going
to
have
it.
They're
not
technologists.
They
don't
–
they're
not
thinking
about
SSO
or
permissions,
all
these
things
they
take
for
granted
but
cost
millions
of
dollars
to
build
in
real
life.
Then
there's
all
these
people
that
are
going
to
pop
out
of
the
woodwork
from
IT,
or
legal,
or
other
business
units
and
they
require
back-end
infrastructure
and
security
certifications
and
all
these
things.
What
you're
being
told
is
that
what
you
need
to
build
is
that
most
30%
of
total
requirements,
right?
This
is
the
risk
where
as
a
capital
allocator,
which
is
fundamentally
a
founder's
job,
you
have
to
think
about
the
risk
of
that
and
you
have
to
think
about
what
amount
of
commitment
the
customer's
making
to
you
to
go
through
that
process.
Pablo
21:50
That's
a
really
good
analogy,the
iceberg
one,
and
it
makes
a
lot
of
sense.
Partly
is
what
you
said
and
partly
is
also
that
they're
potentially
not
used
to
buying
from
startups.
Other
vendors
that
they
buy
from
do
have
all
that
stuff,
and
it's
really
about
the
20%.
There's
a
lot
of
reasons
for
it.
You
raise
these
$2
million;
you
have
these
two
larger
enterprise
customers.
Why
do
you
decide
to
go
a
little
bit
down
market
into
the
mid-market?
Targeting the Mid-Market
Adrian
22:15
Yeah,
I
think
it
was
really
driven
by
two
decisions.
One
was
just
efficiency,
just
go-to-market
efficiency.
The
reality
of
these
very
long
sales
cycles
really
hit
us.
We
were
commanding
2,
3,
$400,000
annual
contract
values
but
on
a
realistically
18
to
36
month
sales
cycle,
if
you're
being
realistic
about
enterprise,
you
look
at
the
benchmarks.
It
says
12
to
18
months.
That's
best
case
scenario,
right?
It's
really
three
years
depending
where
–
it's
18
months
to
3
years.
As
an
early-stage
startup,
that
just
seemed
very
difficult
for
us,
and
we
didn't
think
we
had
the
track
record
to
raise
the
required
amount
of
capital
to
be
able
to
fund
that,
and
so
we
pivoted
into
mid-market
where
we
were
just
seeing
deals
closing
faster.
The
the
deals
–
a
big
one
was
there
weren't
as
many
product
requirements
on
the
contracts.
So
enterprise
said,
yeah,
we'll
buy
it,
but
here'ss
an
addendum
to
the
contract
with
like
15
pages
of
stuff
you
have
to
build.
It
just
was
more
efficient
from
an
acquisition
perspective.
What
we
did
is
we
just
–
we
just
started
targeting
mid-market.
Really
the
one
thing
there,
when
you're
targeting
mid-market
–
and
we
define
mid-market
as
anywhere
between
20,
25
million
of
revenue,
up
to
3
billion
of
revenue.
I
mean,
everybody
has
their
own
definition,
and
people
look
at
different
–
some
people
look
at
FTE
headcount
or
we
look
at
that
revenue
and
a
couple
other
factors.
We
do
go
a
little
bit
high
on
mid-market
with
–
from
a
revenue
threshold.
Really,
what
we
learned
is
it's
a
volume
game.
You
have
to
shift
into
thinking
about
volume,
so
your
pipeline
–
you're
going
to
start
needing
hundreds
of
opportunities
to
push
through.
Another
thing
we
learned
is
that
Canada
doesn't
have
a
very
big
mid-market,
but
the
United
States
does.
I
think
that's
one
thing
that
does
create
some
inefficiency
in
Canadian
founders
is
their
whole
market.
There's
not
a
great
mid-market.
When
you
go
to
cities
in
the
US
like
Cleveland
or
Indianapolis,
there's
an
ocean
of
companies
with
a
couple
hundred
employees
making
50
to
$500
million
a
year
of
revenue.
Pablo
24:35
Did
you
start
selling
into
the
US
right
away,
right
off
the
bat?
Adrian
24:39
No,
our
initial
customers
were
all
large
Canadian
law
firms,
and
then
our
mid-market
customers
were
increasingly
US.
We
got
some
mid-market
Canadian
customers
and
we
thought
this
is
great.
It's
so
much
faster.
There's
way
less
hair
on
these
deals.
We
can
make
them
happy
within
a
matter
of
weeks,
not
in
a
matter
of
months
or
years
type
of
timeline.
Then
just
as
we
kind
of
navigated
through
the
market,
we
just
realized
there
was
just
a
way
bigger
mid-market
in
the
US,
and
so
we
just
started
pointing
ourselves
in
that
direction.
Pablo
25:08
Looking
at
those
first,
let's
say,
ten
or
so
customers,
mid-market
customers,
which
sounds
like
were
mainly
Canadian,
how
did
you
get
those?
Was
that
you
started
outbound
process?
Was
it
you
calling
these
customers
at
first?
Did
you
have
a
salesperson
right
away?
How
did
you
line
those
first
10,
15
customers?
Adrian
25:22
Yeah,
so
they
just
started
inbounding.
It
was
a
lot
of
inbound;
it
was
a
lot
of
referral.
I
mean,
one
of
the
beautiful
things
about
law
firms
is
a
law
firm
or
an
accounting
firm
is
really
like
a
hub-and-spoke
type
of
thing
where
they're
interacting
with
hundreds
or
thousands
or
tens
of
thousands
of
other
organizations
that
likely
have
a
problem
similar
to
the
solution
that
you
have.
There's
just
tons
of
referral
coming
from
these
law
firms.
That
was
really
the
initial
wave
of
inbound
that
we
had.
It
was
organic,
paid,
and
referral
inbound
would
be
a
lot
of
it
getting
to
the
first
million
of
ARR.
Pablo
26:07
Now
a
few
years
later,
more
or
less,
how
many
mid-market
customers
are
you
serving?
Adrian
26:11
We
have
about
200
customers
right
now.
I
would
say
probably
like
75%
of
them
I
would
describe
as
mid-market.
We
still
do
enterprise
customers.
They
just
have
to
fit
inside
of
our
mid-market
commercial
motion
and
product
framework
and
stuff
like
that.
We
very
rarely
make
product
commitments
on
contracts
and
stuff
like
that,
unless
it's
something
that's
already
on
the
road
map
and
maybe
we're
bringing
it
forward
by
six
months.
We
were
going
to
do
it
in
Q4;
we'll
do
it
in
Q2
if
that's
what's
going
to
get
this
deal
across
the
line.
We
won't
do
these
enormous
addendums
like
we
had
to
do
in
the
early
stages.
True Product Market Fit
Pablo
26:53
Makes
sense,
perfect.
Well,
here's
the
last
question
that
we
always
like
to
end
on,
which
is
when
did
you
know
that
you
had
product
market
fit?
Adrian
27:03
When
I
saw
our
customers
–
well,
I
think
there
was
two
moments.
So
the
first
was
when
we
closed
our
first
–
it
was
a
$50,000
deal.
It
was
a
mid-market
law
firm
in
Saskatchewan,
and
they're
still
one
of
their
fantastic
customers.
They're
still
one
of
my
favorite
customers.
When
we
closed
the
deal
–
and
no
founders
were
involved
at
all,
right?
That
was
okay,
the
product
is
speaking
for
itself.
Somebody
we've
hired
and
have
given,
I
mean,
being
realistic,
minimal
amounts
of
training
was
able
to
sit
down
with
the
customer
and
say
here's
the
widget.
Do
you
want
to
buy
and
they
bought,
right?
I
think
that
was
a
big
milestone.
Then
the
next
one
for
me
that
was
–
is
when
I
saw
a
customer
post
a
job
description
for
a
paralegal,
and
on
it,
it
had
experience
with
Athenian
strongly
preferred
or
strong
asset,
some
type
of
language
like
that.
For
me,
I
saw
that
and
I
said,
wow,
the
customer
must
have
a
lot
of
commitment
to
this
product
to
be
including
it
in
the
job
requirements,
and
they
must
expect
that
the
rest
of
the
market
is
purchasing
this
product
at
sufficient
volume
that
there
would
be
other
–
there'd
be
talent
in
the
market
with
experience
using
the
product,
right?
I
think
those
two
things
were
kind
of
the
two
big
signals
to
me
that
we
had
product
market
fit.
Recap
Pablo
28:26
Okay,
well,
we'll
stop
it
there.
Just
as
a
quick
recap,
you
started
off
as
a
lawyer.
You
identified
a
problem.
You
went
super
deep
in
the
validation
and
the
customer
discovery
phase,
which
is
something
that
I
keep
hearing
about
in
the
successful
stories
is
a
phase
that
founders
that
are
successful
tend
not
to
skip.
You
spent
four
or
five
months
talking
to
paralegals,
doing
focus
groups,
did
some
co-development
with
some
large
enterprises,
and
ultimately
shifted
to
to
mid-market
and
have
grown
ever
since.
Thanks
a
lot
for
sharing
your
story
again.
It's
one
that
I
think
founders
will
learn
a
lot
from.
Adrian
28:59
Yeah,
thanks
for
having
me,
Pablo.
Pablo
29:00
Thank
you
so
much
for
listening
all
the
way
through.
It's
been
a
pleasure
having
you
here.
Make
sure
to
subscribe
so
you
don't
miss
the
next
episode.