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October 29, 2024 • 47 mins

Gabrielle Darbyshire's life is a whirlwind of daring ventures and groundbreaking achievements. Picture this: Gaby built an electric car, setting the stage for a career that would straddle media, technology, and law with aplomb. From co-founding Gawker Media to producing a documentary on Steve Jobs, Gabby's journey is a tapestry of audacious pursuits. Embark on a global adventure with her as she recounts the thrill of climbing Cotopaxi volcano, and find out how such experiences echo the entrepreneurial spirit.


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Max Chopovsky (00:02):
This is Moral of the Story interesting people
telling their favorite shortstories and then breaking them
down to understand what makesthem so good.
I'm your host, max Japosky.
Today's guest is GabrielleDerbyshire, whose life reads
like an adventure novel, infusedwith a dash of British wit and
a big helping of entrepreneurialspirit.
Born in Beirut and raised inLondon, gabby's early years were

(00:24):
anything but conventional.
Her precociousness was evidentwhen she constructed an electric
car at the tender age of 15 andwas allowed to drive it despite
not having an actual driver'slicense.
This glimpse of ingenuity wouldforeshadow a career marked by
innovation and boundary-pushingachievements.
Gabby's academic journey tookher to the hallowed halls of the

(00:44):
University of Cambridge, butnot content with a single alma
mater, she also holds a degreefrom City University and a JD
from the Inns of Court School ofLaw.
This collection of degreeswould lay a solid foundation for
her adventurous career at theintersection of media technology
and law.
Gabby's professional careerbegan with a wig and gown, which

(01:05):
she wore in her role as abarrister, working on
environmental cases involvingnuclear power and land
contamination.
From there she moved on tobeing a management consultant,
while somehow finding time toco-found the charity supporting
death row inmates in theCaribbean and working pro bono
on death row appeals to thePrivy Council.
Moving to Silicon Valley in1999 and quickly getting, in her

(01:26):
words, caught up in theinternet world, she worked on a
number of startups as herroommate, nick Denton, kept
trying to get her to join hisfledgling media company.
She finally joined as aco-founder and went all in at
the new startup Gawker Media.
Gawker, which included brandslike Gizmodo, jezebel and
Lifehacker, soon took off In anera when digital media was still

(01:50):
finding its footing.
Gabby helped to transformGawker into a formidable force
characterized by its fearlessjournalism and unflinching
commentary.
With Gabby at the helm, thecompany not only survived but
thrived amidst the evolvingdigital landscape.
Her creative pursuits are asvaried as her professional
endeavors.
In 2015, she executive producedthe documentary Steve Jobs the
man in the Machine, offering anuanced exploration of the tech

(02:11):
icon's life and legacy.
The documentary was praised forits depth and critical
perspective, reflecting Gabby'scommitment to thoughtful and
impactful storytelling.
But her talents aren't confinedto the boardroom or the editing
suite.
Whether scaling mountains,kayaking through rapids or
exploring remote trails, herlove for adventure mirrors her
professional philosophy Alwayspush the boundaries and embrace

(02:32):
the unknown.
Her culinary skills,particularly the art of pickling
are another testament to hereclectic interests.
What started as a hobby hasevolved into a passion, with
Gabby experimenting with flavorsand techniques to create unique
and delicious pickleddelicacies.
Beyond her professional andpersonal achievements, gabby is
deeply committed to giving backto the community.
She volunteers as a crisiscounselor, underscoring her

(02:55):
empathy and dedication to makinga positive impact on the world
around her, even in her sparetime.
With all that being said, gabbyDerbyshire's story is far from
finished, and as she continuesto forge new paths and embrace
new challenges, we can onlyimagine what her next chapter
will hold.
So multitasking, maverick andtrue Renaissance woman, gabby
Derbyshire, welcome to the show.

Gaby Darbyshire (03:17):
Thank you, max.
I'm not sure I even recognizemyself in that wonderful
description, but it's a realpleasure to be here and my gosh,
you tell a wonderful story.

Max Chopovsky (03:27):
Well, I appreciate that.
At the same time, the story weare here to listen to today is
your story.
So set the stage.
Is there anything that weshould know before we get into
your story?

Gaby Darbyshire (03:41):
Well, the context of the story is really
the timing is 2013.
In 2012, I had decided to leaveGorka Media and I was a little
burnt out and I wanted tode-stress and leave the city.
So I decided that, rather thanhaving to answer to any
questions or figure out a newjob or something like that, I
should remove myself from NewYork altogether.
So I went on a year's triparound the world, which is a

(04:05):
grand adventure that I'd wantedto do for a long time, and I
spent six months in Asia and sixmonths in South America, and I
would get various friends tocome and meet me along the way.
So I did a whole bunch ofdifferent adventures.
I hiked Machu Picchu with afriend.
I went up to Vietnam you knowmotorcycles up to Sapa with
another friend, et cetera.
I had people come to Italy, mymother came to Italy.
I hiked the Cinque Terre with afriend, but the big grand

(04:28):
adventure of the year was mysister coming to meet me in
Ecuador for three weeks, and sothat's the context for this
story.

Max Chopovsky (04:35):
Incredible.
I can't wait.
All right, tell me a story.

Gaby Darbyshire (04:39):
Okay, so my sister comes out to meet me in
Ecuador and we're going to do awhole bunch of different
adventurous things.
Like you know, I jumped off abridge, which is a kind of jump
bungee thing, but you swinginstead of fall.
It's all very bizarre.
My sister refused to do thatone because she's wiser than me.
But the grand adventure of thewhole trip was for me and my
sister, my sister Alex, to climbCotopaxi, which is a

(05:02):
snow-capped volcano in Ecuador.
It's part of the Pacific Rim ofFire, of volcanoes.
It's 19,300 feet, it's like6,000 meters high, and my sister
Alex is extremely adventurous,very sporty, very fit In our
family.
She's called the mountain goat.
We hike in Scotland a lot andwhen you go out for a hike with

(05:24):
her and her husband you thinkit's going to be three or four
hours and it's usually likeeight or nine.
So that's the sort of contextof my sister.
She's kind of brilliant andshe's got Duracell batteries in
her and she never runs out ofsteam.
So we decided to climb Cotopaxi.
So she arrives in Quito and thefirst mistake we made was
realizing afterwards, of coursewas that we shouldn't have

(05:47):
planned this climb of this19,000 foot volcano for two days
after my sister arrived,because I'd been in Ecuador
already for a few weeks and Iwas acclimatized.
But Quito is actually one ofthe highest cities in the world.
It's a really highly elevatedcountry.
And so you arrive in Quitoyou're already out of breath.
And then we go to this placewhere we're climbing this
mountain and my sister's like,oh, this is actually kind of

(06:08):
hard to breathe.
Anyway, we're all sitting in therefuge the night before the
ascent of this snow-cappedmountain.
You need ice axes and cramponsand proper equipment, and we're
not mountain climbers.
It's not what we've done before, but we're told this one is
achievable.
So we're sitting in the refuge,we've packed our rucksacks,
we're ready to go, we're goingto have a few hours sleep before

(06:29):
we set off at two in themorning and the point is you go
up in the dark and then you seethe sunrise and then you come
down before it gets too brightand too sort of slushy and a bit
dangerous in the sun.
And as we're sitting there, oneof the guides from another group
there's several groups in thisrefuge comes over to our guide
and starts talking to him andbasically we discover that he's
telling him that a snow bridgeacross a crevasse has collapsed,

(06:54):
which is part of the route, andthat they are suggesting
there's a couple of alternatepossibilities of what you could
do, alternate possibilities ofwhat you could do.
And someone says that they havelaid a ladder.
Some other guide had laid aladder across the crevasse like
an eight foot long ladder, andour guide sort of talking to
this other guy and he comes totalk to us and he says well,

(07:21):
here's the deal.
You're not using the ladder.
I didn't set it.
I don't trust it.
I don't know who put it thereand we don't know how many times
it's been used in the last day.
So that's completely out of thequestion.
So there's two options.
One is we could go the long wayaround and that would probably
add an hour, hour and a half toour journey, so we'd have to go
faster.
And he said I don't think youguys are going to be able to do
that because you're not fullyacclimatized and you're not

(07:42):
experienced climbers.
So I don't think that's a goodidea.
And he said and the only otheroption is you're going to jump,
but you're going to be fine, I'mgoing to be with you and it's
all going to be safe, but you'regoing to jump across the
crevasse.
So my sister and I look at eachother and there's another woman
, jenny, and another couple inour group of five and we all
sort of look at each other andsay, well, I guess we came all

(08:04):
this way, so I guess we're goingto do this right.
So we say, fine, we're going todo this.
And he's very calm, very sortof safe seeming person, very
experienced.
So you know, I feel like I'm insafe hands.
Anyway, we start climbing upthis mountain and, sure enough,
eventually we get to the pointwhere the crevasse is.

(08:24):
And don't forget, it's pitchblack, it's the middle of the
night and it's really, reallycold.
So there's no hanging aroundsituation.
You have to go pretty fast.
And also, to get to the top,you've got to go fast.
So we get to this point and Idon't know if I can describe a
crevasse very well, but imaginetwo bits of paper.
You know they're like this.
I'm trying to get it right.

(08:45):
And that's sort of the gap,because you've got a mountain
that's sheared off like this, sofrom the downside edge, the top
of the edge, here, if you thinkabout it, there's a sort of
there's a field that you couldland on if you were jumping from
here to here.
And if you're jumping straightdown it's a shorter distance
than jumping straight across,right, just by sort of
mathematics and physics.
And so he gets us to the top ofthis ridge and he says I'm going

(09:08):
to jump across, I'm going toput a nice axe in, I'm going to
tie us all tight.
You're going to be tied aroundthe waist.
And then when I say you'regoing to leap, and then if you
slip, I'm going to pull youtight.
So for some reason I drew theshort straw and I had to go
first.
And so I throw myself acrossthis crevasse in the dark.
It's exhilarating, it'sterrifying.
And I'm like okay, I'm safe,it's fine.

(09:29):
So my sister and Jenny come to,and then the other couple say
we're not doing this, we justcan't do this, we're not
interested.
And at the same time anothergroup had come with a guide and
they had all decided theyweren't doing this either and
they were going to turn back.
So the other guy takes thecouple back with them to the
refuge and the three of us go on.
So we go up the mountain.

(09:50):
We fall short of the summit byabout a hundred feet because we
just ran out of time and weweren't going fast enough and my
sister couldn't breatheproperly, and so there's no
shame in that.
It was the most magical thingin the world to see the sunrise
on this gorgeous mountain,overlooking these snow sort of
flanked beautiful rocks below us.

(10:13):
And then, eventually, it's timeto turn around and go back, and
as we're coming down, we get tothis field and it suddenly dawns
on us and we've been so full ofadrenaline getting to the top
that we hadn't really thoughtabout the future.
As we get to the point where wehad jumped before, we look at
this and we realize that thistime we've got to jump upwards,

(10:36):
and the lower you are here, thehigher up you have to jump,
which is the shortest distance.
And if you don't want to jumpup, you've got to jump a longer
distance, which is maybe likenine feet.
And suddenly my sister and Ilook at each other.
I'm like what the fuck are wedoing?
And I was terrified, and thethree of us stood there and we

(10:57):
were like what are we doing?
We can't do this, we just can'tdo this.
And the guide says yes, you can,you're just going to do it in
reverse.
I'm going to jump across.
I'm going to secure the axes.
And he said and I'm going tohold you, and if you slip, and
if you slip into the crevasse,I've got you, it's great, you're
fine.
He said.
But this time there's really noroom for error.

(11:18):
There's no room for the rope toswing, because if the rope
swings and you fall, then theweight of your fall is going to
be too heavy for me to hold you.
So you have to leap extremelyclosely to the ice axe, which
I'm going to place on the otherside, because that's the minimum
amount of rope.
And he said but I don't wantyou to cut your arm off, so

(11:39):
please don't put your arms outwhen you jump, because you don't
want to hit the axe.
So he's telling us this and mysister and I and Jenny are
looking at each other and I'mthinking I honestly don't know
how I do this and I think I'mgoing to have to go down another
way, even if it takes 10 hourslonger.
But he's super encouraging andhe says you can do it, you can

(11:59):
do it.
And so the time was obviouslytoo cold, too sort of urgent,
that you can't really take yourcamera out and take a video.
So my sister is the only personwho has this memory in the head
of what happened, throwingmyself across this crevasse

(12:22):
after a little running jump withmy arms clamped firmly to my
side and literally landing likea penguin on the top of this
ridge, about six inches from anice axe, and then doing a slight
, tiny slip and then he tugs therope and I go sliding off the
other side.
So you made it back down.

(12:44):
Well, obviously I made it backdown, I'm here, but the point
about it is my sister basicallysays that she saw a penguin take
flight and that's how I gotacross an eight foot crevasse.

Max Chopovsky (12:54):
That is outstanding, man.
I wish somebody got out acamera.

Gaby Darbyshire (12:58):
Yes, I have a photograph of the crevasse
itself, but not any video ofanyone doing the actual act.

Max Chopovsky (13:04):
Why did you not go back the long way, when you
could have come up the long way?

Gaby Darbyshire (13:09):
Well, I mean, I think, as your intro may have
indicated, I'm nothing if not arambunctious tomboy at heart,
and I'm not someone who gives upeasily, and so I felt like it's
terrifying.
But the point is that you do itanyway, because that's what
adventure is right.
Adventure usually involves youbeing a little bit scared, and I

(13:31):
think the three of us trustedhim.
So this is what the storyultimately comes down to a few
things, but when you know it'sbeen done before you know that
you're capable of it, it's justa mental fear and your knees are
knocking.
Then there's something thatsort of clicks in me, that sort
of says damn it, I'm not givingin, I'm going to do it.

Max Chopovsky (13:54):
And it had been done before.

Gaby Darbyshire (13:56):
I mean yes, I mean people had been doing this,
obviously because other guidesalso didn't want to use that
ladder and I'm pretty certainthat they had other groups
before us the day before thesame day had probably done the
same thing.
All these guides are veryexperienced and they were all
pretty certain that they knewhow to handle their groups and
what their groups were capableof.

Max Chopovsky (14:15):
That is outstanding.
That is outstanding, at leastit was light.

Gaby Darbyshire (14:22):
That's the point for me of this story.
It's actually the light thatscared me.
It was easy to do it in thedark because I couldn't see it.
It was terrifying to do it inthe light because I knew what I
was in for and I think that's asort of metaphor for me.
Actually, it's a real metaphorfor entrepreneurship, which is

(14:44):
what I do now.
I'm a VC and I work withfounders all the time.
I think that if you knew whatyou were in for, you often
wouldn't start the journey.
So starting in the dark andhaving a little bit of ignorance
about what's coming is thething that makes you brave
enough to start pursuing yourdream.

(15:04):
Doing the thing that is thatscares you most.

Max Chopovsky (15:07):
That's true.
And then when you so sort oflike that naivete, that not
knowing actually how hard it'sgoing to be, that gets you to
kind of take the first step.
And I've talked to a lot ofpeople that say, honestly, if I
knew what I know now when Istarted, if I knew what my

(15:27):
chances actually were, I don'tknow if I would have done that
again.

Gaby Darbyshire (15:31):
Right.
So I think courage is oftendescribed as not being afraid,
but being afraid and doing itanyway, and I think that that's
true.
But there's a nuance in there,which is that sometimes just not
knowing is the best way to getstarted, and being uncertain is
always par for the course.
It's true when you give yourheart to someone, or when you

(15:53):
start a new job or when you putyourself out in public in any
way where you might faceobstacles or rejection, and you
just have to simply believe thatyou will find a way to figure
it out.
And if it doesn't kill you andof course there are some things
which might actually kill you,but if it doesn't kill you, it
will make you stronger, which isa platitude.
But there are elements of truthin all platitudes and I feel

(16:15):
like there's an element abouttrust too.
If you can trust others and youcan trust yourself, then you
can do it.
So I'm generally an optimist.
I usually assume things willwork out and I actually really
trust experts, and I think thisis one of the great sadnesses
about society at the moment iswe seem to have lost our faith
in experts.
But you have to surroundyourself with experts to be your

(16:36):
best self and do your best work, and no one who's really great
doesn't always say that theystand on the shoulders of giants
, right?
So trusting other people, Ithink, is really key to being
brave Now in the Olympics.
The reason I chose this storythis morning rather than the
other one I was going to tellyou about meeting a shark when I
was 11, or some other storyabout trading dirty limericks

(16:59):
with Christopher Hitchens, but Ichose this one actually because
Scott this morning said oh,this is really interesting.
Op Doc in the New York Times isactually from 2017, but they
brought it back because of theOlympics and the Swedish
researchers paid volunteers togo to a 10 meter high diving
board and see if they would jumpoff, and they recorded it.

(17:22):
And it was all about doubt,human doubt and how you act in
that moment of fear.
And some jump and some don'tabout 70% jump and 30% don't,
and a lot of them say they jumpbecause of the peer pressure, of
not wanting to make otherpeople wait for them or having a
girlfriend that they didn'twant to embarrass or something
like that.
So it's around doing things thatscare you, and when I saw that

(17:43):
this morning, I'm like, oh yes,I've got to tell the crevasse
story.
That's the one I have to tell.
So it was like the sign fromthe universe that that was the
right story, and I sort of feellike the Olympics are a perfect,
another perfect reason fortelling this now, because I was
thinking about the highboarddiving or the gymnastics and I
was wondering why do we love andare so thrilled by those sports

(18:07):
?
It's because that has thatadded jeopardy.
Right, you actually couldparalyze yourself.
They're dangerous.
You're not going to paralyzeyourself if you row too hard or
if you run a second faster,probably unless you fall over.

Max Chopovsky (18:21):
But gymnastics and diving is sort of terrifying
your heart's in your mouth andthat's why there's such exciting
things to watch I agree, in thewinter olympics, you know the
ski long jump when they start onthat huge hill and then they
speed up to I don't know 100miles an hour, something crazy,
and they do this man.
They're just soaring throughthe air like a bird.
I've never thought about itthat way, but I think you're

(18:41):
absolutely right.
I think part of it is people.
I think they're kind of 98%rooting for the person and sort
of 2% wondering what wouldhappen if they fell and being
happy that they don't have toexperience it.
But they could just watch thissort of human drama unfold on TV
.

Gaby Darbyshire (18:59):
Yeah, and I think that you get excited about
things when your heart'sbeating and you're tense.
It's what makes great TV showsis you get tense.
It's really so beloved becauseyou don't know what's going to
happen and you're sort of onedge and I feel like that's sort
of the sports I love have thatelement in them and I sort of
think that the reason I like thestory and people sort of are on
edge when I tell it is that youcan imagine that they're

(19:20):
thinking what would I do if Iwas standing on that edge?
Would I jump or not?
And so they fill in the gaugeand people have told me
afterwards it makes me break outin hives just listening to you
tell that story.
It makes me so scared.

Max Chopovsky (19:34):
That's exactly why they break out in hives when
they get scared, because theystart to put themselves in that
situation and they're like, ohshit, I can picture myself
standing right there lookingback the other way.
And, by the way, when youillustrated for me what the
crevasse looks like when youhave to cross it going up the
mountain, the immediate questionI had in my mind was how the
hell do you go back?

Gaby Darbyshire (19:54):
See, you were thinking that already and I just
didn't think it when I was onthe trip.
It didn't cross my mind tothink about that At the time.
I only cared about getting tothe top.

Max Chopovsky (20:03):
Yeah, this is completely different.
You're on a mountain, youradrenaline is running already,
you're committed to this thing.
You're not going to think aboutnecessarily the way back,
you're just going to think aboutthe challenge that's right in
front of you.
And then that actually makes iteven more interesting when you
come back and you're like, ohshit, now I have to get back

(20:25):
over it.
Yeah, that's fantastic.
So it's interesting.
When you talk about puttingtrust in experts and the
challenge we have with that, Ithink you also I mean this kind
of goes without saying, causeit's the assumption that the
statement is based on.
You have to assume that theexperts are actually experts,
right, like that guy.

(20:46):
Your guide said I don't trustthat ladder, and you trusted
that statement.
But there was another guide whosaid I think we can.
I'll just put this ladder downand we can cross using this
ladder.
There's a part in the Everestclimb where they have to walk
across a ladder.
I'm sure you've seen picturesof it and though I'm sure that
was put in place with probablymore forethought than this

(21:09):
ladder.
But the people that were withthis guide on that mountain
probably trusted that guide whenhe said I'm going to put down
this ladder and we're going tobe fine.
So you have to actuallysurround yourself with experts
who are experts whom you cantrust, and the assumption was
this guy knew what he was doingwhen he was like no, go on the
ladder number one and number two, I got you.

(21:31):
When you do this other way.

Gaby Darbyshire (21:35):
I mean, I think if I was surmising what was
going on, I imagine the guy whoputs the ladder down was doing
it for his group, whether it'sgoing up or coming down, and
they'd just seen it collapse,and he probably was like it's
good and it's fine, but if it'sgoing to be used over and over
again, you just don't know whatits point of failure is.
So our guy was saying I justdon't know how many people have
crossed it and it could havemoved.

(21:56):
That's the issue.
Not that it would necessarilybe an untrustworthy guide who
put it down in the first place.
It might've been perfect forhis small number of people, but
it clearly, if it was done in ahurry, wasn't being done in a
conscious way of oh, this hasgot to sustain for hundreds of
people to do this over the nextthree weeks.
And that's why he was like I'mjust not sure, because I haven't

(22:17):
seen it myself, and so I wantyou to be prepared for this
other alternative.
So I think in my scenario, bothof them could be experts, but
the circumstances can change.

Max Chopovsky (22:25):
That's fair.
That's fair.
So, as you think about thisstory, the way you tell it, what
makes the story so good in yourmind?
What makes it a good story?

Gaby Darbyshire (22:36):
I love the fact that it sort of involves my
sister.
It's this grand adventure.
Some stories you can tell arejust about things that happen to
you and they don't really havethat sort of communal part of
involving other people that youcare about.
So that's number one.
But I feel like when I tellthis story people, just like I
said, they put themselves there.
It gives this sense and thisfrisson of danger.

(22:57):
They can't quite believe thatwe didn't turn back.
They love the fact that thegrit means you just keep going
because you just can't back out,because you're too proud,
something like that, and so thevisuals of it, I think, just
make people laugh.
The idea of me landing like apenguin on the other side of
this crevasse is a memory thatpeople have said.
I kind of think of you as apenguin and as a result it sort

(23:19):
of becomes a fun, familiar storythat your friends sort of
appreciate and over the yearspeople have loved.

Max Chopovsky (23:25):
Love that, Love it Did the story.
I mean, this happened now overa decade ago.
Has this story changed overtime?
Have you tweaked it, you know,made it shorter or changed any
details in the story?

Gaby Darbyshire (23:39):
Well, I haven't changed much of the factual
stuff because obviously there'sactual photographic evidence of
the crevasse, but I'm certain ifyou ask my sister what happened
it would probably differ alittle bit.
In fact I know that's generallytrue of a lot of my childhood
stories.
So a little context.
I have seven siblings.

(23:59):
I grew up in the Middle East.
My family were born and broughtup all over the world.
Most of them are greattravelers, but my mother is one
of the best raconteurs I've everknown my mother and my
grandfather, and I learned fromthe best.
And my mother has suchincredible stories.
I usually tell her stories.
They all have a one-linesentence headline, like my

(24:20):
mother was the only person inEngland ever to have been booked
for speeding on a horse in apublic place, or the time when
my mother stole the Shah ofIran's stallion, or you know
stories like this, like endlessstories that my mother has.
And so once she was visiting mein New York and I had a dinner
party for her and at one end ofthe dinner party I started

(24:42):
telling my friends a story aboutbeing kidnapped in Beirut and
my mother was like that's notwhat happened.
She pipes up from the other endof the table and this got
everyone going into like hang ona second.
And I was like, really, are allmy stories false?
And she said said well, I don'tknow.
So I said well, what about thisone?
And I told her a story.
She goes no, that's not whathappened.
You're mixing up two people.
And so my friends started goingwell, this is ridiculous.

(25:03):
And so we were going back andforth and then one of my friends
said you know, you guys shouldwrite a book together.
And so we decided we couldwrite a story about what I
thought had happened.
And my mother would correct mebecause she's not going to write
her own book.
She says she signed theofficial secrets act and she
can't tell her own stories.
But she can damn well correctme if I'm wrong.

(25:24):
And so we were going to do thisseries of letters and call it.
I'll tell it my way.

Max Chopovsky (25:29):
Oh my God, I would totally get that.
I would totally buy that book.

Gaby Darbyshire (25:32):
So I don't know how these stories change over
time, but obviously they changeenough that my mother's telling
me that a lot of the stories Iremember from childhood, or
remember being told fromchildhood, are not in fact
accurate entirely.

Max Chopovsky (25:45):
I've had that same conversation with my
parents.
There's stories that I rememberso clearly in my mind and when
I talk to them they correct meon multiple important parts of
each story.
And I think that's you know.
Malcolm Gladwell talks aboutthis.
Our memories are malleable andthings shift over time and it's
not.
In some cases we want toembellish the story.

(26:06):
The further away from it we getchronologically, the more
grandiose it becomes.
But even if that's not theintent, a lot of the time
stories do sort of shift becauseour memories are malleable.
But before we go on, what isthe official secret act and why
did your mother have to sign it?

Gaby Darbyshire (26:28):
Oh, it's a law in the UK that says you're not
allowed to tell state secrets,and my mother worked for the
intelligence services so she hadto sign it.

Max Chopovsky (26:36):
Oh man, okay Well , I think we need to have your
mother.

Gaby Darbyshire (26:39):
There's a whole bunch of other stories about
that, but that's not the right.
This is not the right forum forthat.

Max Chopovsky (26:42):
No, Okay, so you have, throughout all the
different sort of parts of yourcareer, you have heard some
fantastic stories, as we justdiscussed and with your mother.
So, as you think about all ofthese reconteurs that you have

(27:03):
encountered, that you've talkedto, that you've heard stories
from, what do their greatstories have in common?

Gaby Darbyshire (27:11):
I think the element of guessing and surprise
and you're not sure what'scoming next and you're sort of
on the edge of your chairwaiting to find out and you're
always uncertain, maybesurprised, about the twists and
turns it takes.
I love a story that is such ashaggy dog tale that it's so far
from where it began that youcan't even imagine how their

(27:32):
dots are connected.
I love stories like that, likereally good jokes, like long
jokes are fantastic becausethey're so winding and I like I
think people love stories wherethe listener feels that they
could empathize, it could havehappened to them.
It makes them think about whatthey might've done in that
situation.
You know whether it'sembarrassing or sweet, you know

(27:54):
there's, there's a sort of theconnection piece I think is
really important.
If you feel that it was, itcould have been you in those
shoes.
I think that makes it reallysort of meaningful and connects
with people at this base level.

Max Chopovsky (28:08):
Totally.
Yeah, I agree with that.
I love that.
That drives engagement too.
If somebody is sort of asyou're telling the story,
imagining themselves in theprotagonist's shoes is sort of
as you're telling the story,imagining themselves in the
protagonist's shoes, they are somuch more engaged because now
they're wondering well, how dothe decisions diverge?
What I would do and what thestoryteller would do?

(28:28):
So what makes for a goodstoryteller?

Gaby Darbyshire (28:31):
I think honesty right.
So if you're telling a story,whether it's funny or scary or
brilliant or just plainembarrassing, it comes across
better when it's just, it feelsreally natural.
If it feels too rehearsed, ifit feels too produced, then it's
.
You know, it's a standuproutine or it's a scripted show
or something.

(28:51):
I think when you'restorytelling around a campfire,
being sort of a bit raw if youlike telling a story that you
love to tell, so it comes sonaturally that you don't have to
think about how to say it.
That's a great hallmark and Ithink it could be about the
simplest events.
Don't overthink it, just picksomething that really mattered
to you and your personality willshow through it.
And then you know obviously bebeing aware of your audience and

(29:15):
pitching the right story to theright people and listening and
trying to gauge their reaction,especially if you're going to
tell the story over and overagain.
You can learn a lot from thecues of how people respond.
And you know there's a it's notanother story, but there's a
lovely family legend that mygrandfather knew JR Tolkien very
well and Tolkien was veryfamous for wanting feedback on

(29:38):
his work and he was an academicat Oxford and he was an
etymologist and was really anexpert in the origin of language
, and so when he wrote the Lordof the Rings and the Hobbit and
the Silmarillion, he was reallytrying to see if he could create
a fully contained language thatwas internally consistent, and
so he sent a copy of the firstdraft of the Hobbit to my

(30:01):
grandfather to ask for feedback,and this family legend has it
that he, grandpa, read it to mymother and her two sisters when
my mother was about seven yearsold and took copious notes and
said they didn't like thischaracter, they wanted to hear
more about this character.
They fell asleep here.
They were wide awake here thisis what you need to change and

(30:23):
apparently wrote pages of notesand Tolkien rewrote the Hobbit
based on my mom's feedback as aseven-year-old.

Max Chopovsky (30:31):
Outstanding.

Gaby Darbyshire (30:34):
Like I tell you , most of my good stories are
actually about my mother.

Max Chopovsky (30:37):
That is crazy.
You know it's interesting whenyou talk about what makes for a
good storyteller.
The unrehearsed nature of agood story gives the storyteller
freedom because not becausethey would deviate from the

(30:58):
story, but because there'ssomething inherently sort of
freeing about not having toregurgitate what is in front of
you, you know, not to readwhat's been rehearsed or not to
be so strict about the actualtelling of the story.
And I used to do these eventswhere I would moderate panels
with CEOs and I would alwayshave these index cards that I

(31:21):
would use with my sort ofopening remarks and I would give
you know I would speak for fiveto 10 minutes, so not
insignificant.
And looking back on the videosof those opening remarks you can
tell that you know, even thejokes don't land as well, even
when it's witty, and I thoughtso hard about how to deliver a

(31:43):
specific punchline.
It's just not as good as when Iam speaking organically,
because I'm sort of bound bythis predetermined plan of what
I'm trying to say.

Gaby Darbyshire (31:56):
I really dislike presentations and
speeches and find myself muchmore comfortable when it's like
a panel or a chat, where you'reresponding to somebody else's
question or somebody else'sthought.
I feel like prepared keynotesmake me incredibly nervous
because they don't feel naturalenough.
So it's an interesting thing inmy professional life I try and

(32:19):
avoid those altogether.

Max Chopovsky (32:21):
Yeah, it's not a bad thing.
I think for me when I was sortof shifting away from those
prepared keynotes is first I hadto get over the sort of
nervousness that I was going todeliver every main point that I
wanted to deliver.
But once I got past that itreally was freeing.

(32:41):
I found myself being morecomfortable, being more witty,
being able to respond towhatever's happening in the
audience or sort of interactwith them a little bit more
organically, and I think thatprobably makes it more enjoyable
for them too.
So how do you use storytellingin your personal life?
Having given so much thought towhat makes a good story and
having heard so many greatstories, how do you do that?

Gaby Darbyshire (33:05):
I feel like storytelling isn't my profession
, but it's a great joy and I'mdefinitely have a bunch of
friends all really greatraconteurs and storytelling is a
great joy.
You sit at a dinner table, youtell funny stories, you tell
funny jokes.
I was taught by the best.
My grandfather taught me towrite limericks and dog roll

(33:26):
verse, and so I write all sortsof poetry just for fun many bad
songs, so I don't do it as ahabit that I must do.
It's one of those things thatcomes out in a social situation.
You've had Scott on the podcast.
He's obviously a greatstoryteller as well, and it's
one of those things that I feellike your entire life is

(33:48):
essentially surrounded by andimmersed in storytelling.
The stories you tell yourselfevery day about what you're
going to do that day, or whetheryou feel good or bad about
something, is that they're all anarrative, and obviously some
people are really good attelling them stories that get
them to move forward with greatvigor and others tell them
stories that can hold them backbecause they are afraid of

(34:08):
things, and so ultimately, we'retelling ourselves stories every
day and professionally I workwith startups and founders and
they are obviously tellingstories to the world that what
they're doing is going to beworld changing and it's going to
be important.
And they're telling a story toinvestors and they're telling a
story to customers, and so,however you cut it, you can't

(34:29):
get away from having to tell agood story every day in your
life.
And so there's a differencebetween doing it professionally
and just doing it for the joy ofit in your social life, and I
sort of don't think of thestorytelling I do professionally
as being a job.
It's just weaved into thefabric of day-to-day life, right
, whereas socially you actuallydo think, oh, what's a good

(34:53):
story for this appropriatescenario Like who wants to hear
it?
Are they interested?
What kind of people are they?
And so there's this consciouschoice when you decide to tell a
story socially, but I thinkprofessionally, it just sort of
happens organically.
Day in, day out, every emailyou write is a story.

Max Chopovsky (35:12):
That's true.
Hopefully, the more concise thebetter.
That actually is an art formwithout understatement is an art
form without understatement Tobe able to, in a social setting,
think of a story that isrelevant to that setting and
relevant to the audience isabsolutely priceless.
There's a guy I used to workfor who could do that and, to

(35:35):
your earlier point, he couldtell a story about something
completely mundane or banal thatis just.
You know, just happened totranspire in the last few days,
you know, the last couple ofdays leading up to the story,
and you could just make it soundso hilarious, so impactful that
everybody would, you know, berolling on the floor laughing

(35:57):
right.
And then you would try toretell that story to somebody
else and it wouldn't hit thesame way and you're like, oh,
it's not me, it's not the story,it is him, he's the one that
can deliver it so well.

Gaby Darbyshire (36:11):
Yeah, scott has a favorite memory of a dinner
party from a few years ago wherea friend of ours told a joke
which was the most ridiculousjoke you have ever heard.
And it goes on for a very longtime and you have no idea what
the punchline is going to be.
And there's literally only oneperson in the world that could
tell this joke, and it's David,because, honestly, we've tried

(36:33):
and it doesn't work.
It has to be him and it mayhave been only possible in that
circumstance.
And it's really interestingbecause it's the difference
between a joy and a greatraconteur and a bore right.
So one who knows his audienceand how to pitch it and knows
how to be concise or knows howto be shaggy at the right time,
versus someone who just wants totell their story when they want

(36:54):
to.

Max Chopovsky (36:55):
And in fact you made an interesting point that I
think is also true.
In some cases there's literallyonly one point in time when a
story could be told and toldwell and told impactfully.
The same story from the sameperson could only has sort of
one telling in it.
Like we were at dinner with acouple almost a year ago and I

(37:16):
told this random story aboutflying back from Florida on
business and sitting in themiddle seat and what it was like
to sit in the middle seatbetween the person on my right
and the person on my left andhow it was just the most absurd
experiences, given what thosetwo people were doing, and we
were crying at the dinner table,laughing so hard.
And I don't think I could eventell that same story now, even

(37:37):
if I remembered all the facts,because there was just something
magical about that moment thatit just made it right to tell
that specific story and that wasit.
It had a telling count of onebefore it expired.

Gaby Darbyshire (37:51):
Right, right.
Well, I think this is why I'mso envious of people who are
just funny people, not whetherthey're comedians or not.
But you can tell a good storyand you can be funny, and
sometimes you can be both, andsometimes you're really good at
one and not the other.
But truly funny people can turntaking their dog for a walk
into an uproarious tale, andthat's a genuine skill.

(38:13):
That's a marvelous thing tobehold.

Max Chopovsky (38:15):
It really, really is.
So I'm sure that you are anavid reader.
What is one of your favoritebooks that gets storytelling
right?

Gaby Darbyshire (38:29):
This was a tricky one to think about.
I'm, in fact, such a nerd thatI have kept a list of every book
I've ever read since I moved toAmerica more than 25 years ago.
So I actually know exactly howmany books I read in any given
year and how busy I was and whatkind of mood I was in and what
I was interested in by the booklist from each year, and I'm

(38:50):
going to do some analysis on itat some point.
But it's definitely flippedfrom 80% fiction, 20% nonfiction
to the other way around, whichI think is common as you get
older, so really interestingpatterns in your own reading
history.
So I'm sort of very aware of myfavorite books.
But I found it hard to answerthis specifically without

(39:12):
wanting to mention two.
So recently I read theOverstory, which is a very large
book about trees and about thenatural world, and the thing I
think is extraordinary aboutthat is that it's essentially a
scientific treatise wrapped upin a great big novel, and if it

(39:33):
had been a scientific treatisenobody would have read it.
It would have been seen tooearnest or beating people over
the head about climate change.
But because it's wrapped up inthis delicious, beautiful novel,
it really gets a point across.
And there's a line in the bookwhere he says it's by Richard
Powers.
He says the best arguments inthe world won't change a

(39:56):
person's mind.
The only thing that can do thatis a good story.
And I think about that a lot interms of politics and why
politics is so driven by emotionthese days.
And it's because he's right.
People aren't interested infacts sometimes, they're just
interested in a good story, andso really great storytellers can
move hearts and minds.
But that book was a marvelousbook.

(40:16):
Hearts and minds, but that bookwas a marvelous book.
And I won't give away thesecret surprise, which took much
debate afterwards about whetherit was true or not.
But it's a lovely book aboutthe natural world and about
trees and about the history ofAmerica, and it's beautiful.
And my other favorite book,which has always been on my top

(40:36):
list, is Winter's Tale by MarkHalperin.
I don't know if you've everread that.
It's a big saga, magic realism,fantasy, set in New York at the
turn of the century.
And I just think how can younot love a novel that starts
with a white horse gallopingthrough the streets of lower

(40:56):
Manhattan?
And it's this sweeping saga,historical, scientific, romantic
.
It's beautiful, but it's also avery long slog.

Max Chopovsky (41:07):
When you describe it as a sweeping saga, I kind
of assumed it was going to be awar and peace kind of situation.

Gaby Darbyshire (41:13):
Yeah.

Max Chopovsky (41:14):
Amazing.
So I know this one might be atricky question to answer
because you have to make someassumptions.
But if you could say one thingto 20-year-old Gabby assuming
20-year-old Gabby would notbrush you off and would listen
to you, and setting aside thegrandfather paradox and all that

(41:37):
stuff if you could say onething to your 20-year year old
self, what would it be?

Gaby Darbyshire (41:42):
Leap and the net will appear.

Max Chopovsky (41:44):
I love that.
Do you feel like you weren'tdoing enough of that when you
were 20?

Gaby Darbyshire (41:53):
Yeah, I think that, like many people who are
well-educated and come fromsupportive parents who think
that education is important, youthink that you've got to do
certain things, and I think whenI was 20, I thought I was going
to have a career as a lawyer,and I thought that was the right

(42:13):
thing to do, and it took me notthat long to realize I didn't
want to be a lawyer.
In England, if you're a lawyerfor too long, if you're a
barrister for too long, the twoultimate goals are to become a
judge or a politician, andneither really appealed to me.
I don't want to sit in judgmenton other people.
I certainly didn't feel that Iwas cut out for politics, and so
it was definitely the case thatI felt that if I wasn't an

(42:38):
expert in something, then Iwouldn't be valued and that I
wouldn't be successful and thatI had to do something down the
straight and narrow.
And I think it takes a lot oftime and wisdom to realize that
doing a whole bunch of differentthings and being a generalist
and sort of being a bitpolymathic, if you like, and
trying a bunch of differentthings that make you happy is
actually a better way to liveyour life, and so I feel like I

(43:00):
wish I had trusted myselfearlier to leap into doing
unknown, unconventional things,and it led me ultimately to
entrepreneurship and doing allthe different things I've done,
which has been fabulous, but Iprobably would have liked to
have learned that lesson earlierscenario?

Max Chopovsky (43:18):
Yeah Well, I certainly don't think.
My opinion, having put togetheryour bio, I do not think that
you took too long, because thenumber of things, the variety of
the things that you've donehave made for a life so far,
that really lends itself to somepretty damn good stories, you

(43:42):
know.
I mean, some people don'trealize that until much later in
their life.
And I think that it's alsoreally really good advice to
younger people who and I was oneof those people and you were
for a time as well think thatthere is honor in predictability

(44:07):
, right, and that is sad,because actually letting go and
sort of seeing where theuniverse takes you is a really
powerful thing and, frankly,it's a great muscle to exercise,
because some of the time itactually will not lead you in a

(44:31):
better direction, and that'sokay too.
And I think if people say thereare some people, I'm sure, out
there that say you know what?
I'm just going to try somethingtotally different, I'm going to
take a very sort of not passive,but I'm going to try to seed
some control, and their firstadventure after seeding control

(44:53):
is not a great one and they justuse that data point to confirm
that actually their previousapproach was correct.
I have to stay on the straightand narrow, as you said, and
that's the way to do it.
But I think, beyond theoriginal sort of step of hey,
I'm going to let go and I'mgoing to see where the universe

(45:14):
takes me, it's equally importantto understand that not every
place it's going to take you isgoing to be a better place.
But as long as you takesomething away from that, as
long as you learn a lesson,that's a net positive.
I think a lot of people justgive up.

Gaby Darbyshire (45:29):
Well, I think that's exactly right.
I think it comes back to thisthing about fear and trust.
So you can be afraid, but youcan trust yourself to figure it
out.
And I think some people areinstilled with fear from
whatever circumstances they grewup in or things not working out
, and they become afraid toessentially get back on the

(45:50):
horse.
And I think the hallmark of mybusiness now the word we use
most often is resilience.
And we're talking about it interms of climate resilience,
because I invest in climate,companies and how to make the
planet and people more resilient.
But on a human, personal level,the founders and the companies
have to be resilient and you asindividuals have to be resilient

(46:14):
.
And resilience to me meansbeing prepared to expect that
there will be obstacles andthere will be things that go
wrong and that they don't knockyou sideways, that you are okay
with expectation of rejection,of surprise, of uncertainty, of
bad things happening, but thatthey don't rock your fundamental

(46:38):
core and that you still haveenough trust and faith in
yourself to keep going, evenwhen things are not easy.
And I think resilience issomething where it's a muscle.
I think you can exercise it,make people stronger and better

(47:05):
people and probably more humbleand probably more accommodating
and tolerant of other people'sfoibles and failings, and I
think that that makes you moreeasy to navigate life.
So resilience is really thecore characteristic I would wish
young people to have.
Yeah, I think it's fantasticand I couldn't agree more,
because too many young people tohave.

Max Chopovsky (47:19):
Yeah, I think it's fantastic and I couldn't
agree more, because too manyyoung people these days are
raised without resilience andthat is a challenge as they head
into the real world Just don'tfall into the crevasse, yes,
well, that does it, gabbyDarbyshire.

(47:39):
Polymath, renaissance woman andtaker of risks despite her fear
.
Thank you for being on the show.

Gaby Darbyshire (47:47):
Max, it's been a real pleasure, thank you.

Max Chopovsky (47:50):
The pleasure is all mine For show notes and more
.
Head over to mosspodorg.
Find us on Apple Podcasts,spotify, wherever you get your
podcast on.
This was Moral of the Story.
I'm Max Tchaikovsky.
Thank you for listening.
Talk to you next time.
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