Lawyers
love
certainty.
Startups
run
on
everything
but.
That
gap
is
where
many
legal
careers
either
stagnate
or
accelerate.
The
difference
is
rarely
about
raw
talent.
It
is
about
how
honestly
you
see
the
bet
you
are
placing
on
your
own
time,
judgment,
and
resilience.
In
a
recent
“Notes
to
My
(Legal)
Self”
episode,
I
spoke
with
Rina
Wang,
most
recently
assistant
general
counsel
at
AI
startup
Prepared,
which
was
acquired
by
Axon.
Rina
has
lived
the
full
cycle
many
in-house
counsel
fantasize
about:
federal
clerkships,
litigation,
multiple
venture-backed
startups,
an
AI
boom
role,
and
a
fast
acquisition.
Underneath
the
glossy
version
of
that
path
is
a
more
honest
reality
that
most
lawyers
never
hear
before
they
jump.
This
is
an
attempt
to
correct
that.
Thinking
In
Bets
When
You
Only
Get
One
Chip
Rina
said
something
that
should
be
printed
on
every
startup
job
description
for
lawyers:
“I
really
am
an
investor
going
into
this
startup.
I
am
investing
my
time
and
my
career.
It
is
human
capital,
but
it
is
just
as
important,
if
not
more
so,
than
being
a
VC
investor
and
throwing
in
money.”
VCs
spread
bets
across
10
to
20
companies.
Lawyers
place
one
bet
at
a
time.
If
a
fund’s
single
unicorn
offsets
nine
failures,
that
is
a
win.
If
your
one
job
implodes,
that
is
your
income,
your
resume,
and
your
emotional
bandwidth
for
the
year.
During
the
pandemic,
Rina
read
“Thinking
in
Bets”
by
Annie
Duke
and
began
to
see
career
choices
the
way
poker
players
see
decisions
made
under
pressure.
You
never
have
perfect
information.
Outcomes
rarely
track
effort.
Luck
and
timing
shape
more
than
we
want
to
admit.
“How
do
we
make
the
best
decisions
in
terms
of
uncertainty
or
a
limited
amount
of
data?”
she
asked.
That
is
the
core
question
of
startup
life.
The
problem
is
that
lawyers
are
trained
to
avoid
uncertainty.
We
are
rewarded
for
spotting
risks,
issuing
careful
warnings,
and
forecasting
every
scenario.
In
startups,
that
mindset
is
felt
as
a
delay.
The
work
still
demands
rigor,
but
the
posture
has
to
change
from
“prove
this
is
safe”
to
“place
a
smart
bet
knowing
it
never
will
be.”
If
you
are
considering
a
startup
move,
the
first
step
is
internal.
You
are
not
choosing
between
certainty
and
uncertainty.
You
are
choosing
the
type
of
uncertainty
you
want
and
how
concentrated
you
want
your
bet
to
be.
Graduating
Into
Recession,
Practicing
Inside
Turbulence
Rina
is
clear
that
the
2008
recession
shaped
everything
that
came
later.
She
started
law
school
in
2007.
By
graduation,
“no
one
was
working.
There
was
certainly
no
deal
work
going
on.”
She
calls
herself
a
“recession
graduate”
who
learned
early
that
macro
conditions
will
disregard
your
plans.
Employment
litigation
during
a
recession
gave
her
a
flood
of
work
and
immediate
responsibility.
“There
are
a
lot
of
juicy
cases
all
the
time,”
she
said.
She
was
taking
and
defending
depositions
and
drafting
motions
from
the
start.
That
pace
and
pressure
later
made
startup
life
feel
familiar,
not
destabilizing.
If
you
trained
in
environments
with
more
insulation,
be
honest
about
that.
You
can
build
the
muscles.
You
will
feel
the
intensity
more
quickly.
The
key
isn’t
asking
“am
I
resilient”
in
theory.
It
is
asking
whether
you
have
had
to
own
outcomes
before
in
situations
where
no
one
could
buffer
the
fallout
for
you.
Mission
Is
Not
Fluff.
It
Is
How
You
Survive
the
Middle.
On
paper,
Rina’s
path
looks
scattered:
spirits
made
in
a
lab,
construction
tech,
and
then
an
AI
platform
for
911
emergency
response.
The
through
line
is
mission.
Environmental
sustainability.
Practical
tools
for
real-world
infrastructure.
Public
safety.
She
also
chose
male-dominated
industries.
“I
had
this
urge,
and
this
need
to
kick
down
doors
for
myself
and
create
a
seat
for
myself
at
the
table
in
these
spaces
where
there
was
not
a
lot
of
diversity.”
That
choice
made
her
path
harder
and
sharper
by
design.
Mission
is
not
a
soft
factor
for
lawyers
in
startups.
It
is
what
carries
you
through
the
middle
chapters:
a
tough
funding
round,
a
volatile
market,
a
surprise
product
shift,
or
in
Prepared’s
case,
an
acquisition
process
triggered
in
part
by
the
CEO
being
hospitalized
with
a
spider
bite
that
nearly
cost
him
his
leg.
This
is
the
deeper
point
behind
thinking
in
bets.
You
cannot
predict
the
details.
You
can
only
decide
whether
the
mission,
team,
and
customers
matter
enough
that
the
volatility
is
acceptable.
If
you
are
evaluating
a
startup,
ask
yourself
plainly:
Do
I
want
to
think
about
this
problem
for
three
to
five
years?
Do
I
respect
the
customer?
Do
I
believe
the
world
is
better
if
this
product
scales?
If
the
answer
is
lukewarm,
the
bet
is
mispriced
before
it
even
starts.
The
Emotional
Reality
Of
Being
‘Calm’
During
An
Acquisition
Prepared
announced
its
acquisition
by
Axon
on
September
23,
and
the
acquisition
closed
on
October
1.
Internally,
the
intensity
had
been
building
for
months.
None
of
that
shows
up
in
the
press
release.
Rina
described
the
internal
experience
this
way:
“Everybody
expects
legal
to
be
calm
in
the
eyes
of
the
storm.”
You
become
the
anchor
for
a
team
that
may
be
anxious,
disoriented,
and
overwhelmed
by
the
unknowns.
That
expectation
comes
at
the
exact
moment
your
own
role
may
be
at
risk.
She
added,
“I
am
more
than
comfortable
admitting,
hey,
this
is
a
new
situation
for
all
of
us.
We
are
building
the
plane
as
we
are
flying
it.”
The
company
did
not
know
an
acquisition
was
coming
months
in
advance.
Conversations
with
Axon
moved
quickly.
Internal
reorganizations
were
happening
in
real
time.
Staying
functional
required
honesty
instead
of
forced
certainty.
The
leadership
team
respected
that
more
than
pretense.
If
your
company
is
heading
toward
an
acquisition
or
operating
in
a
consolidating
market,
prepare
yourself
emotionally
as
well
as
legally.
You
need
peers
who
can
normalize
what
you
are
going
through,
mentors
who
have
lived
M&A
integrations,
and
enough
personal
structure
to
process
the
experience
without
letting
it
consume
you.
From
Risk
Avoidance
To
Value
Creation
This
is
the
pivot
that
matters
most.
In
a
firm
or
a
large
company,
you
can
succeed
by
being
a
highly
accurate
legal
technician.
In
a
startup,
that
is
not
enough.
“If
you
are
just
pointing
out
the
law
and
regulations,
you
are
not
adding
any
value
separate
and
apart
from
outside
counsel,”
Rina
said.
Startups
need
generalists
who
can
negotiate
commercial
deals,
structure
partnerships,
build
privacy
and
security
foundations,
and
support
product
decisions.
Your
value
shifts
from
risk
minimization
to
enabling
the
company
to
move.
You
are
no
longer
a
step
in
a
workflow.
You
are
part
of
the
engine.
Before
joining
a
startup,
ask
yourself:
Do
I
enjoy
working
directly
with
sales,
product,
and
engineering
teams?
Do
I
know
how
to
connect
legal
risk
to
revenue
and
growth?
Can
I
move
at
a
speed
that
sometimes
feels
uncomfortable?
These
are
learned
skills,
but
only
if
you
want
to
learn
them.
Seeing
Your
Career
As
A
Series
Of
Intentional
Experiments
At
the
end
of
our
conversation,
I
asked
Rina
for
a
final
takeaway.
She
said,
“Be
humble
to
uncertainties.
A
lot
is
not
within
your
control.
A
lot
is
luck
and
timing.”
That
humility
is
not
resignation.
It
is
clarity.
If
you
understand
that
you
are
making
a
bet
every
time
you
choose
a
job,
you
can
make
better
and
more
intentional
choices.
You
can
evaluate
missions
more
honestly.
You
can
prepare
for
volatility
instead
of
resisting
it.
You
can
show
up
as
a
legal
operator
who
helps
the
company
move,
not
one
who
braces
against
every
risk.
Startups
are
not
for
everyone.
They
are
also
not
inherently
reckless
or
chaotic.
They
are
experiments
in
speed,
mission,
market
timing,
and
people.
If
you
choose
well
and
place
your
bet
consciously,
one
intense
year
can
stretch
your
career
further
than
10
quiet
years
anywhere
else.
Olga
V.
Mack
is
the
CEO
of
TermScout,
where
she
builds
legal
systems
that
make
contracts
faster
to
understand,
easier
to
operate,
and
more
trustworthy
in
real
business
conditions.
Her
work
focuses
on
how
legal
rules
allocate
power,
manage
risk,
and
shape
decisions
under
uncertainty.
A
serial
CEO
and
former
General
Counsel,
Olga
previously
led
a
legal
technology
company
through
acquisition
by
LexisNexis.
She
teaches
at
Berkeley
Law
and
is
a
Fellow
at
CodeX,
the
Stanford
Center
for
Legal
Informatics. She
has
authored
several
books
on
legal
innovation
and
technology,
delivered
six
TEDx
talks,
and
her
insights
regularly
appear
in
Forbes,
Bloomberg
Law,
VentureBeat,
TechCrunch,
and
Above
the
Law.
Her
work
treats
law
as
essential
infrastructure,
designed
for
how
organizations
actually
operate.