59: Gabrielle Darbyshire
“And the three of us stood there, looked at each other, and said, ‘we can’t do this.’”
About Gaby
Gaby Darbyshire’s life reads like an adventure novel infused with a dash of British wit and a big helping of entrepreneurial spirit. Born in Beirut and raised in London, Gaby's early years were anything but conventional. Her precociousness was evident when she constructed an electric car at the tender age of 15—and was allowed to drive it despite not having an actual drivers license. This glimpse of ingenuity would foreshadow a career marked by innovation and boundary-pushing achievements.
Gaby’s academic journey took her to the hallowed halls of the University of Cambridge, but, not content with a single alma mater, she also holds a degree from City University, and a JD from the Inns of Court School of Law. This collection of degrees would lay a solid foundation for her adventurous career at the intersection of media, technology, and law.
Gaby’s professional career began with… a wig and gown, which she wore in her role as a barrister working on environmental cases involving nuclear power and land contamination. From there, she moved on to being a management consultant, while somehow finding time to co-found a charity supporting Death Row inmates in the Caribbean and working pro bono on death row appeals to the Privy Council.
Moving to Silicon Valley in 1999 and quickly getting, in her words, “caught up in the internet world,” she worked on a number of startups as her roommate Nick Denton kept trying to get her to join his fledgling media company. She finally joined as a co-founder and went all in at the new startup, Gawker Media.
Gawker, which included brands like Gizmodo, Jezebel, and Lifehacker, soon took off. In an era when digital media was still finding its footing, Gaby helped to transform Gawker into a formidable force, characterized by its fearless journalism and unflinching commentary. With Gaby at the helm, the company not only survived but thrived amidst the evolving digital landscape.
Gaby's creative pursuits are as varied as her professional endeavors. In 2015, she executive produced the documentary "Steve Jobs: The Man in the Machine," offering a nuanced exploration of the tech icon’s life and legacy. The documentary was praised for its depth and critical perspective, reflecting Gaby’s commitment to thoughtful and impactful storytelling.
But Gaby's talents aren't confined to the boardroom. Whether scaling mountains, kayaking through rapids, or exploring remote trails, Gaby’s love for adventure mirrors her professional philosophy: always push the boundaries and embrace the unknown.
Her culinary skills, particularly in the art of pickling, are another testament to her eclectic interests. What started as a hobby has evolved into a passion, with Gaby experimenting with flavors and techniques to create unique and delicious pickled delicacies.
Beyond her professional and personal achievements, Gaby is deeply committed to giving back to the community. She volunteers as a crisis counselor, underscoring her empathy and dedication to making a positive impact on the world around her. Even in her spare time, she’s driven by purpose and compassion.
With all that being said, Gaby Darbyshire’s story is far from finished, and as she continues to forge new paths and embrace new challenges, we can only imagine what her next chapter will hold.
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Max Chopovsky: 0:02
This is Moral of the Story interesting people telling their favorite short stories and then breaking them down to understand what makes them so good. I'm your host, max Japosky. Today's guest is Gabrielle Derbyshire, whose life reads like an adventure novel, infused with a dash of British wit and a big helping of entrepreneurial spirit. Born in Beirut and raised in London, gabby's early years were anything but conventional. Her precociousness was evident when she constructed an electric car at the tender age of 15 and was allowed to drive it despite not having an actual driver's license. This glimpse of ingenuity would foreshadow a career marked by innovation and boundary-pushing achievements. Gabby's academic journey took her to the hallowed halls of the University of Cambridge, but not content with a single alma mater, she also holds a degree from City University and a JD from the Inns of Court School of Law. This collection of degrees would lay a solid foundation for her adventurous career at the intersection of media technology and law.
Max Chopovsky: 1:01
Gabby's professional career began with a wig and gown, which she wore in her role as a barrister, working on environmental cases involving nuclear power and land contamination. From there she moved on to being a management consultant, while somehow finding time to co-found the charity supporting death row inmates in the Caribbean and working pro bono on death row appeals to the Privy Council. Moving to Silicon Valley in 1999 and quickly getting, in her words, caught up in the internet world, she worked on a number of startups as her roommate, nick Denton, kept trying to get her to join his fledgling media company. She finally joined as a co-founder and went all in at the new startup Gawker Media. Gawker, which included brands like Gizmodo, jezebel and Lifehacker, soon took off In an era when digital media was still finding its footing. Gabby helped to transform Gawker into a formidable force characterized by its fearless journalism and unflinching commentary. With Gabby at the helm, the company not only survived but thrived amidst the evolving digital landscape.
Max Chopovsky: 2:00
Her creative pursuits are as varied as her professional endeavors. In 2015, she executive produced the documentary Steve Jobs the man in the Machine, offering a nuanced exploration of the tech icon's life and legacy. The documentary was praised for its depth and critical perspective, reflecting Gabby's commitment to thoughtful and impactful storytelling. But her talents aren't confined to the boardroom or the editing suite. Whether scaling mountains, kayaking through rapids or exploring remote trails, her love for adventure mirrors her professional philosophy Always push the boundaries and embrace the unknown.
Max Chopovsky: 2:33
Her culinary skills, particularly the art of pickling are another testament to her eclectic interests. What started as a hobby has evolved into a passion, with Gabby experimenting with flavors and techniques to create unique and delicious pickled delicacies. Beyond her professional and personal achievements, gabby is deeply committed to giving back to the community. She volunteers as a crisis counselor, underscoring her empathy and dedication to making a positive impact on the world around her, even in her spare time. With all that being said, gabby Derbyshire's story is far from finished, and as she continues to forge new paths and embrace new challenges, we can only imagine what her next chapter will hold. So multitasking, maverick and true Renaissance woman, gabby Derbyshire, welcome to the show.
Gaby Darbyshire: 3:17
Thank you, max. I'm not sure I even recognize myself in that wonderful description, but it's a real pleasure to be here and my gosh, you tell a wonderful story.
Max Chopovsky: 3:27
Well, I appreciate that. At the same time, the story we are here to listen to today is your story. So set the stage. Is there anything that we should know before we get into your story?
Gaby Darbyshire: 3:41
Well, the context of the story is really the timing is 2013. In 2012, I had decided to leave Gorka Media and I was a little burnt out and I wanted to de-stress and leave the city. So I decided that, rather than having to answer to any questions or figure out a new job or something like that, I should remove myself from New York altogether. So I went on a year's trip around the world, which is a grand adventure that I'd wanted to do for a long time, and I spent six months in Asia and six months in South America, and I would get various friends to come and meet me along the way. So I did a whole bunch of different adventures. I hiked Machu Picchu with a friend. I went up to Vietnam you know motorcycles up to Sapa with another friend, et cetera. I had people come to Italy, my mother came to Italy. I hiked the Cinque Terre with a friend, but the big grand adventure of the year was my sister coming to meet me in Ecuador for three weeks, and so that's the context for this story.
Max Chopovsky: 4:35
Incredible. I can't wait. All right, tell me a story.
Gaby Darbyshire: 4:39
Okay, so my sister comes out to meet me in Ecuador and we're going to do a whole bunch of different adventurous things. Like you know, I jumped off a bridge, which is a kind of jump bungee thing, but you swing instead of fall. It's all very bizarre. My sister refused to do that one because she's wiser than me. But the grand adventure of the whole trip was for me and my sister, my sister Alex, to climb Cotopaxi, which is a snow-capped volcano in Ecuador. It's part of the Pacific Rim of Fire, of volcanoes. It's 19,300 feet, it's like 6,000 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 and when you go out for a hike with her and her husband you think it's going to be three or four hours and it's usually like eight or nine. So that's the sort of context of my sister. She's kind of brilliant and she's got Duracell batteries in her and she never runs out of steam. So we decided to climb Cotopaxi. So she arrives in Quito and the first mistake we made was realizing afterwards, of course was that we shouldn't have planned this climb of this 19,000 foot volcano for two days after my sister arrived, because I'd been in Ecuador already for a few weeks and I was acclimatized. But Quito is actually one of the highest cities in the world. It's a really highly elevated country. And so you arrive in Quito you're already out of breath. And then we go to this place where we're climbing this mountain and my sister's like, oh, this is actually kind of hard to breathe.
Gaby Darbyshire: 6:10
Anyway, we're all sitting in the refuge the night before the ascent of this snow-capped mountain. You need ice axes and crampons and 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 going to have a few hours sleep before we set off at two in the morning and the point is you go up in the dark and then you see the sunrise and then you come down before it gets too bright and too sort of slushy and a bit dangerous in the sun.
Gaby Darbyshire: 6:39
And as we're sitting there, one of the guides from another group there's several groups in this refuge comes over to our guide and starts talking to him and basically we discover that he's telling him that a snow bridge across a crevasse has collapsed, which is part of the route, and that they are suggesting there's a couple of alternate possibilities of what you could do, alternate possibilities of what you could do. And someone says that they have laid a ladder. Some other guide had laid a ladder across the crevasse like an eight foot long ladder, and our guide sort of talking to this other guy and he comes to talk to us and he says well, 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 there and we don't know how many times it's been used in the last day. So that's completely out of the question.
Gaby Darbyshire: 7:28
So there's two options. One is we could go the long way around and that would probably add an hour, hour and a half to our journey, so we'd have to go faster. And he said I don't think you guys are going to be able to do that because you're not fully acclimatized and you're not experienced climbers. So I don't think that's a good idea. And he said and the only other option is you're going to jump, but you're going to be fine, I'm going to be with you and it's all going to be safe, but you're going to jump across the crevasse. So my sister and I look at each other and there's another woman, jenny, and another couple in our group of five and we all sort of look at each other and say, well, I guess we came all this way, so I guess we're going to do this right. So we say, fine, we're going to do this. And he's very calm, very sort of safe seeming person, very experienced. So you know, I feel like I'm in safe hands.
Gaby Darbyshire: 8:18
Anyway, we start climbing up this mountain and, sure enough, eventually we get to the point where the crevasse is. And don't forget, it's pitch black, it's the middle of the night and it's really, really cold. So there's no hanging around situation. 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 I don't know if I can describe a crevasse very well, but imagine two bits of paper. You know they're like this. I'm trying to get it right. And that's sort of the gap, because you've got a mountain that's sheared off like this, so from the downside edge, the top of the edge, here, if you think about it, there's a sort of there's a field that you could land on if you were jumping from here to here. And if you're jumping straight down it's a shorter distance than jumping straight across, right, just by sort of mathematics and physics.
Gaby Darbyshire: 9:05
And so he gets us to the top of this ridge and he says I'm going to jump across, I'm going to put a nice axe in, I'm going to tie us all tight. You're going to be tied around the waist. And then when I say you're going to leap, and then if you slip, I'm going to pull you tight. So for some reason I drew the short straw and I had to go first. And so I throw myself across this crevasse in the dark. It's exhilarating, it's terrifying. And I'm like okay, I'm safe, it's fine.
Gaby Darbyshire: 9:29
So my sister and Jenny come to, and then the other couple say we're not doing this, we just can't do this, we're not interested. And at the same time another group had come with a guide and they had all decided they weren't doing this either and they were going to turn back. So the other guy takes the couple back with them to the refuge and the three of us go on. So we go up the mountain. We fall short of the summit by about a hundred feet because we just ran out of time and we weren't going fast enough and my sister couldn't breathe properly, and so there's no shame in that. It was the most magical thing in the world to see the sunrise on this gorgeous mountain, overlooking these snow sort of flanked beautiful rocks below us.
Gaby Darbyshire: 10:13
And then, eventually, it's time to turn around and go back, and as we're coming down, we get to this field and it suddenly dawns on us and we've been so full of adrenaline getting to the top that we hadn't really thought about the future. As we get to the point where we had jumped before, we look at this and we realize that this time we've got to jump upwards, and the lower you are here, the higher up you have to jump, which is the shortest distance. And if you don't want to jump up, you've got to jump a longer distance, which is maybe like nine feet. And suddenly my sister and I look at each other. I'm like what the fuck are we doing? And I was terrified, and the three of us stood there and we were like what are we doing? We can't do this, we just can't do this.
Gaby Darbyshire: 11:01
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 to hold you, and if you slip, and if you slip into the crevasse, I've got you, it's great, you're fine. He said.
Gaby Darbyshire: 11:14
But this time there's really no room for error. There's no room for the rope to swing, because if the rope swings and you fall, then the weight of your fall is going to be too heavy for me to hold you. So you have to leap extremely closely to the ice axe, which I'm going to place on the other side, because that's the minimum amount of rope. And he said but I don't want you to cut your arm off, so please don't put your arms out when you jump, because you don't want to hit the axe.
Gaby Darbyshire: 11:43
So he's telling us this and my sister and I and Jenny are looking at each other and I'm thinking I honestly don't know how I do this and I think I'm going to have to go down another way, even if it takes 10 hours longer. But he's super encouraging and he says you can do it, you can do it. And so the time was obviously too cold, too sort of urgent, that you can't really take your camera out and take a video. So my sister is the only person who has this memory in the head of what happened, throwing myself across this crevasse after a little running jump with my arms clamped firmly to my side and literally landing like a penguin on the top of this ridge, about six inches from an ice axe, and then doing a slight, tiny slip and then he tugs the rope and I go sliding off the other side. So you made it back down.
Gaby Darbyshire: 12:44
Well, obviously I made it back down, I'm here, but the point about it is my sister basically says that she saw a penguin take flight and that's how I got across an eight foot crevasse.
Max Chopovsky: 12:54
That is outstanding, man. I wish somebody got out a camera.
Gaby Darbyshire: 12:58
Yes, I have a photograph of the crevasse itself, but not any video of anyone 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 a rambunctious tomboy at heart, and I'm not someone who gives up easily, and so I felt like it's terrifying. But the point is that you do it anyway, because that's what adventure is right. Adventure usually involves you being a little bit scared, and I think the three of us trusted him. So this is what the story ultimately comes down to a few things, but when you know it's been done before you know that you're capable of it, it's just a mental fear and your knees are knocking. Then there's something that sort of clicks in me, that sort of says damn it, I'm not giving in, 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 guides also didn't want to use that ladder and I'm pretty certain that they had other groups before us the day before the same day had probably done the same thing. All these guides are very experienced and they were all pretty certain that they knew how to handle their groups and what their groups were capable of.
Max Chopovsky: 14:15
That is outstanding. That is outstanding, at least it was light.
Gaby Darbyshire: 14:22
That's the point for me of this story. It's actually the light that scared me. It was easy to do it in the dark because I couldn't see it. It was terrifying to do it in the light because I knew what I was in for and I think that's a sort of metaphor for me. Actually, it's a real metaphor for entrepreneurship, which is what I do now. I'm a VC and I work with founders all the time. I think that if you knew what you were in for, you often wouldn't start the journey. So starting in the dark and having a little bit of ignorance about what's coming is the thing that makes you brave enough to start pursuing your dream. Doing the thing that is that scares you most.
Max Chopovsky: 15:07
That's true. And then when you so sort of like that naivete, that not knowing actually how hard it's going to be, that gets you to kind of take the first step. And I've talked to a lot of people that say, honestly, if I knew what I know now when I started, if I knew what my chances actually were, I don't know if I would have done that again.
Gaby Darbyshire: 15:31
Right. So I think courage is often described as not being afraid, but being afraid and doing it anyway, 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 get started, and being uncertain is always par for the course. It's true when you give your heart to someone, or when you start a new job or when you put yourself out in public in any way where you might face obstacles or rejection, and you just have to simply believe that you will find a way to figure it out. And if it doesn't kill you and of course there are some things which might actually kill you, but if it doesn't kill you, it will make you stronger, which is a platitude. But there are elements of truth in all platitudes and I feel like there's an element about trust too. If you can trust others and you can trust yourself, then you can do it. So I'm generally an optimist. I usually assume things will work out and I actually really trust experts, and I think this is one of the great sadnesses about society at the moment is we seem to have lost our faith in experts. But you have to surround yourself with experts to be your best self and do your best work, and no one who's really great doesn't always say that they stand on the shoulders of giants, right? So trusting other people, I think, is really key to being brave Now in the Olympics.
Gaby Darbyshire: 16:51
The reason I chose this story this morning rather than the other one I was going to tell you about meeting a shark when I was 11, or some other story about trading dirty limericks with Christopher Hitchens, but I chose this one actually because Scott this morning said oh, this is really interesting. Op Doc in the New York Times is actually from 2017, but they brought it back because of the Olympics and the Swedish researchers paid volunteers to go to a 10 meter high diving board and see if they would jump off, and they recorded it. And it was all about doubt, human doubt and how you act in that moment of fear. And some jump and some don't about 70% jump and 30% don't, and a lot of them say they jump because of the peer pressure, of not wanting to make other people wait for them or having a girlfriend that they didn't want to embarrass or something like that.
Gaby Darbyshire: 17:39
So it's around doing things that scare you, and when I saw that 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 from the universe that that was the right story, and I sort of feel like the Olympics are a perfect, another perfect reason for telling this now, because I was thinking about the highboard diving or the gymnastics and I was wondering why do we love and are so thrilled by those sports? It's because that has that added jeopardy. Right, you actually could paralyze yourself. They're dangerous. You're not going to paralyze yourself 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 and that's why there's such exciting things to watch I agree, in the winter olympics, you know the ski long jump when they start on that huge hill and then they speed up to I don't know 100 miles an hour, something crazy, and they do this man. They're just soaring through the air like a bird. I've never thought about it that way, but I think you're 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 would happen if they fell and being happy that they don't have to experience it. But they could just watch this sort of human drama unfold on TV.
Gaby Darbyshire: 18:59
Yeah, and I think that you get excited about things when your heart's beating and you're tense. It's what makes great TV shows is you get tense. It's really so beloved because you don't know what's going to happen and you're sort of on edge and I feel like that's sort of the sports I love have that element in them and I sort of think that the reason I like the story and people sort of are on edge when I tell it is that you can imagine that they're thinking what would I do if I was standing on that edge? Would I jump or not? And so they fill in the gauge and people have told me afterwards it makes me break out in 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 they start to put themselves in that situation and they're like, oh shit, I can picture myself standing right there looking back the other way. And, by the way, when you illustrated for me what the crevasse looks like when you have to cross it going up the mountain, the immediate question I 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 on the trip. It didn't cross my mind to think about that At the time. I only cared about getting to the top.
Max Chopovsky: 20:03
Yeah, this is completely different. You're on a mountain, your adrenaline is running already, you're committed to this thing. You're not going to think about necessarily the way back, you're just going to think about the challenge that's right in front of you. And then that actually makes it even more interesting when you come back and you're like, oh shit, now I have to get back over it. Yeah, that's fantastic. So it's interesting.
Max Chopovsky: 20:29
When you talk about putting trust in experts and the challenge we have with that, I think you also I mean this kind of goes without saying, cause it's the assumption that the statement is based on. You have to assume that the experts are actually experts, right, like that guy. Your guide said I don't trust that ladder, and you trusted that statement. But there was another guide who said I think we can. I'll just put this ladder down and we can cross using this ladder.
Max Chopovsky: 20:58
There's a part in the Everest climb where they have to walk across a ladder. I'm sure you've seen pictures of it and though I'm sure that was put in place with probably more forethought than this ladder. But the people that were with this guide on that mountain probably trusted that guide when he said I'm going to put down this ladder and we're going to be fine. So you have to actually surround yourself with experts who are experts whom you can trust, and the assumption was this guy knew what he was doing when he was like no, go on the ladder number one and number two, I got you. 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 who puts the ladder down was doing it for his group, whether it's going 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's going to be used over and over again, you just don't know what its point of failure is.
Gaby Darbyshire: 21:52
So our guy was saying I just don't know how many people have crossed it and it could have moved. That's the issue. Not that it would necessarily be an untrustworthy guide who put it down in the first place. It might've been perfect for his small number of people, but it clearly, if it was done in a hurry, wasn't being done in a conscious way of oh, this has got to sustain for hundreds of people to do this over the next three weeks. And that's why he was like I'm just not sure, because I haven't seen it myself, and so I want you to be prepared for this other alternative. So I think in my scenario, both of them could be experts, but the circumstances can change.
Max Chopovsky: 22:25
That's fair. That's fair. So, as you think about this story, the way you tell it, what makes the story so good in your mind? 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 are just about things that happen to you and they don't really have that sort of communal part of involving other people that you care about. So that's number one. But I feel like when I tell this story people, just like I said, they put themselves there. It gives this sense and this frisson of danger. They can't quite believe that we didn't turn back. They love the fact that the grit means you just keep going because you just can't back out, because you're too proud, something like that, and so the visuals of it, I think, just make people laugh. The idea of me landing like a penguin on the other side of this crevasse is a memory that people have said. I kind of think of you as a penguin and as a result it sort of becomes a fun, familiar story that your friends sort of appreciate and over the years people have loved.
Max Chopovsky: 23:25
Love that, Love it Did the story. I mean, this happened now over a decade ago. Has this story changed over time? 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's actual photographic evidence of the crevasse, but I'm certain if you ask my sister what happened it would probably differ a little bit. In fact I know that's generally true of a lot of my childhood stories. So a little context. I have seven siblings. I grew up in the Middle East. My family were born and brought up all over the world. Most of them are great travelers, but my mother is one of the best raconteurs I've ever known my mother and my grandfather, and I learned from the best. And my mother has such incredible stories.
Gaby Darbyshire: 24:14
I usually tell her stories. They all have a one-line sentence headline, like my mother was the only person in England ever to have been booked for speeding on a horse in a public place, or the time when my mother stole the Shah of Iran's stallion, or you know stories like this, like endless stories that my mother has. And so once she was visiting me in New York and I had a dinner party for her and at one end of the dinner party I started telling my friends a story about being kidnapped in Beirut and my mother was like that's not what happened. She pipes up from the other end of the table and this got everyone going into like hang on a second. And I was like, really, are all my stories false? And she said said well, I don't know.
Gaby Darbyshire: 24:59
So I said well, what about this one? And I told her a story. She goes no, that's not what happened. You're mixing up two people. And so my friends started going well, this is ridiculous. And so we were going back and forth and then one of my friends said you know, you guys should write a book together. And so we decided we could write a story about what I thought had happened. And my mother would correct me because she's not going to write her own book. She says she signed the official secrets act and she can't tell her own stories. But she can damn well correct me if I'm wrong. And so we were going to do this series 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 change enough that my mother's telling me that a lot of the stories I remember from childhood, or remember being told from childhood, are not in fact accurate entirely.
Max Chopovsky: 25:45
I've had that same conversation with my parents. There's stories that I remember so clearly in my mind and when I talk to them they correct me on multiple important parts of each story. And I think that's you know. Malcolm Gladwell talks about this. Our memories are malleable and things shift over time and it's not. In some cases we want to embellish the story. The further away from it we get chronologically, the more grandiose it becomes. But even if that's not the intent, a lot of the time stories do sort of shift because our memories are malleable. But before we go on, what is the 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 had to 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 for that.
Max Chopovsky: 26:42
No, Okay, so you have, throughout all the different sort of parts of your career, you have heard some fantastic stories, as we just discussed and with your mother. So, as you think about all of these reconteurs that you have encountered, that you've talked to, that you've heard stories from, what do their great stories have in common?
Gaby Darbyshire: 27:11
I think the element of guessing and surprise and you're not sure what's coming next and you're sort of on the edge of your chair waiting to find out and you're always uncertain, maybe surprised, about the twists and turns it takes. I love a story that is such a shaggy dog tale that it's so far from where it began that you can't even imagine how their dots are connected. I love stories like that, like really good jokes, like long jokes are fantastic because they're so winding and I like I think people love stories where the listener feels that they could empathize, it could have happened to them. It makes them think about what they might've done in that situation. You know whether it's embarrassing or sweet, you know there's, there's a sort of the connection piece I think is really important. If you feel that it was, it could have been you in those shoes. I think that makes it really sort 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 as you're telling the story, imagining themselves in the protagonist's shoes is sort of as you're telling the story, imagining themselves in the protagonist's shoes, they are so much more engaged because now they're wondering well, how do the decisions diverge? What I would do and what the storyteller would do? So what makes for a good storyteller?
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 plain embarrassing, it comes across better when it's just, it feels really natural. If it feels too rehearsed, if it feels too produced, then it's. You know, it's a standup routine or it's a scripted show or something. I think when you're storytelling around a campfire, being sort of a bit raw if you like telling a story that you love to tell, so it comes so naturally that you don't have to think about how to say it. That's a great hallmark and I think it could be about the simplest events. Don't overthink it, just pick something that really mattered to you and your personality will show through it. And then you know obviously be being aware of your audience and pitching the right story to the right people and listening and trying to gauge their reaction, especially if you're going to tell the story over and over again. You can learn a lot from the cues of how people respond.
Gaby Darbyshire: 29:25
And you know there's a it's not another story, but there's a lovely family legend that my grandfather knew JR Tolkien very well and Tolkien was very famous for wanting feedback on his work and he was an academic at Oxford and he was an etymologist and was really an expert in the origin of language, and so when he wrote the Lord of the Rings and the Hobbit and the Silmarillion, he was really trying to see if he could create a fully contained language that was internally consistent, and so he sent a copy of the first draft of the Hobbit to my grandfather to ask for feedback, and this family legend has it that he, grandpa, read it to my mother and her two sisters when my mother was about seven years old and took copious notes and said they didn't like this character, they wanted to hear more about this character. They fell asleep here. They were wide awake here this is what you need to change and apparently wrote pages of notes and Tolkien rewrote the Hobbit based on my mom's feedback as a seven-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 when you talk about what makes for a good storyteller. The unrehearsed nature of a good story gives the storyteller freedom because not because they would deviate from the story, but because there's something inherently sort of freeing about not having to regurgitate what is in front of you, you know, not to read what's been rehearsed or not to be so strict about the actual telling of the story. And I used to do these events where I would moderate panels with CEOs and I would always have these index cards that I would use with my sort of opening remarks and I would give you know I would speak for five to 10 minutes, so not insignificant. And looking back on the videos of those opening remarks you can tell that you know, even the jokes don't land as well, even when it's witty, and I thought so hard about how to deliver a specific punchline. It's just not as good as when I am speaking organically, because I'm sort of bound by this predetermined plan of what I'm trying to say.
Gaby Darbyshire: 31:56
I really dislike presentations and speeches and find myself much more comfortable when it's like a panel or a chat, where you're responding to somebody else's question or somebody else's thought. I feel like prepared keynotes make me incredibly nervous because they don't feel natural enough. So it's an interesting thing in my professional life I try and avoid those altogether.
Max Chopovsky: 32:21
Yeah, it's not a bad thing. I think for me when I was sort of shifting away from those prepared keynotes is first I had to get over the sort of nervousness that I was going to deliver every main point that I wanted to deliver. But once I got past that it really was freeing. I found myself being more comfortable, being more witty, being able to respond to whatever's happening in the audience or sort of interact with them a little bit more organically, and I think that probably makes it more enjoyable for them too. So how do you use storytelling in your personal life? Having given so much thought to what makes a good story and having heard so many great stories, 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'm definitely have a bunch of friends all really great raconteurs and storytelling is a great joy. You sit at a dinner table, you tell funny stories, you tell funny jokes. I was taught by the best. My grandfather taught me to write limericks and dog roll verse, and so I write all sorts of poetry just for fun many bad songs, so I don't do it as a habit that I must do. It's one of those things that comes out in a social situation.
Gaby Darbyshire: 33:39
You've had Scott on the podcast. He's obviously a great storyteller as well, and it's one of those things that I feel like your entire life is essentially surrounded by and immersed in storytelling. The stories you tell yourself every day about what you're going to do that day, or whether you feel good or bad about something, is that they're all a narrative, and obviously some people are really good at telling them stories that get them to move forward with great vigor and others tell them stories that can hold them back because they are afraid of things, and so ultimately, we're telling ourselves stories every day and professionally I work with startups and founders and they are obviously telling stories to the world that what they're doing is going to be world changing and it's going to be important. And they're telling a story to investors and they're telling a story to customers, and so, however you cut it, you can't get away from having to tell a good story every day in your life.
Gaby Darbyshire: 34:34
And so there's a difference between doing it professionally and just doing it for the joy of it in your social life, and I sort of don't think of the storytelling I do professionally as being a job. It's just weaved into the fabric of day-to-day life, right, whereas socially you actually do think, oh, what's a good story for this appropriate scenario Like who wants to hear it? Are they interested? What kind of people are they? And so there's this conscious choice when you decide to tell a story socially, but I think professionally, it just sort of happens organically. Day in, day out, every email you write is a story.
Max Chopovsky: 35:12
That's true. Hopefully, the more concise the better. That actually is an art form without understatement is an art form without understatement To be able to, in a social setting, think of a story that is relevant to that setting and relevant to the audience is absolutely priceless. There's a guy I used to work for who could do that and, to your earlier point, he could tell a story about something completely mundane or banal that is just. You know, just happened to transpire in the last few days, you know, the last couple of days leading up to the story, and you could just make it sound so hilarious, so impactful that everybody would, you know, be rolling on the floor laughing right. And then you would try to retell that story to somebody else and it wouldn't hit the same 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 where a friend of ours told a joke which was the most ridiculous joke you have ever heard. And it goes on for a very long time and you have no idea what the punchline is going to be. And there's literally only one person in the world that could tell this joke, and it's David, because, honestly, we've tried and it doesn't work. It has to be him and it may have been only possible in that circumstance. And it's really interesting because it's the difference between a joy and a great raconteur and a bore right. So one who knows his audience and how to pitch it and knows how to be concise or knows how to be shaggy at the right time, versus someone who just wants to tell their story when they want to.
Max Chopovsky: 36:55
And in fact you made an interesting point that I think is also true. In some cases there's literally only one point in time when a story could be told and told well and told impactfully. The same story from the same person could only has sort of one telling in it. Like we were at dinner with a couple almost a year ago and I told this random story about flying back from Florida on business and sitting in the middle seat and what it was like to sit in the middle seat between the person on my right and the person on my left and how it was just the most absurd experiences, given what those two people were doing, and we were crying at the dinner table, laughing so hard. And I don't think I could even tell that same story now, even if I remembered all the facts, because there was just something magical about that moment that it just made it right to tell that specific story and that was it. It had a telling count of one before it expired.
Gaby Darbyshire: 37:51
Right, right. Well, I think this is why I'm so envious of people who are just funny people, not whether they're comedians or not. But you can tell a good story and you can be funny, and sometimes you can be both, and sometimes you're really good at one and not the other. But truly funny people can turn taking their dog for a walk into an uproarious tale, and that's a genuine skill. That's a marvelous thing to behold.
Max Chopovsky: 38:15
It really, really is. So I'm sure that you are an avid reader. What is one of your favorite books that gets storytelling right?
Gaby Darbyshire: 38:29
This was a tricky one to think about. I'm, in fact, such a nerd that I have kept a list of every book I've ever read since I moved to America more than 25 years ago. So I actually know exactly how many books I read in any given year and how busy I was and what kind of mood I was in and what I was interested in by the book list from each year, and I'm going to do some analysis on it at some point. But it's definitely flipped from 80% fiction, 20% nonfiction to the other way around, which I think is common as you get older, so really interesting patterns in your own reading history. So I'm sort of very aware of my favorite books. But I found it hard to answer this specifically without wanting to mention two. So recently I read the Overstory, which is a very large book about trees and about the natural world, and the thing I think is extraordinary about that is that it's essentially a scientific treatise wrapped up in a great big novel, and if it had been a scientific treatise nobody would have read it. It would have been seen too earnest or beating people over the head about climate change. But because it's wrapped up in this delicious, beautiful novel, it really gets a point across.
Gaby Darbyshire: 39:47
And there's a line in the book where he says it's by Richard Powers. He says the best arguments in the world won't change a person's mind. The only thing that can do that is a good story. And I think about that a lot in terms of politics and why politics is so driven by emotion these days. And it's because he's right. People aren't interested in facts sometimes, they're just interested in a good story, and so really great storytellers can move hearts and minds.
Gaby Darbyshire: 40:15
But that book was a marvelous book. Hearts and minds, but that book was a marvelous book. And I won't give away the secret surprise, which took much debate afterwards about whether it was true or not. But it's a lovely book about the natural world and about trees and about the history of America, and it's beautiful. And my other favorite book, which has always been on my top list, is Winter's Tale by Mark Halperin. I don't know if you've ever read 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 you not love a novel that starts with a white horse galloping through the streets of lower Manhattan? And it's this sweeping saga, historical, scientific, romantic. It's beautiful, but it's also a very long slog.
Max Chopovsky: 41:07
When you describe it as a sweeping saga, I kind of assumed it was going to be a war and peace kind of situation.
Gaby Darbyshire: 41:13
Yeah.
Max Chopovsky: 41:14
Amazing. So I know this one might be a tricky question to answer because you have to make some assumptions. But if you could say one thing to 20-year-old Gabby assuming 20-year-old Gabby would not brush you off and would listen to you, and setting aside the grandfather paradox and all that stuff if you could say one thing 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't doing enough of that when you were 20?
Gaby Darbyshire: 41:53
Yeah, I think that, like many people who are well-educated and come from supportive parents who think that education is important, you think that you've got to do certain things, and I think when I was 20, I thought I was going to have a career as a lawyer, and I thought that was the right thing to do, and it took me not that long to realize I didn't want to be a lawyer.
Gaby Darbyshire: 42:19
In England, if you're a lawyer for too long, if you're a barrister for too long, the two ultimate goals are to become a judge or a politician, and neither really appealed to me.
Gaby Darbyshire: 42:27
I don't want to sit in judgment on other people. I certainly didn't feel that I was cut out for politics, and so it was definitely the case that I felt that if I wasn't an expert in something, then I wouldn't be valued and that I wouldn't be successful and that I had to do something down the straight and narrow. And I think it takes a lot of time and wisdom to realize that doing a whole bunch of different things and being a generalist and sort of being a bit polymathic, if you like, and trying a bunch of different things that make you happy is actually a better way to live your life, and so I feel like I wish I had trusted myself earlier to leap into doing unknown, unconventional things, and it led me ultimately to entrepreneurship and doing all the different things I've done, which has been fabulous, but I probably would have liked to have learned that lesson earlier scenario?
Max Chopovsky: 43:18
Yeah Well, I certainly don't think. My opinion, having put together your bio, I do not think that you took too long, because the number of things, the variety of the things that you've done have made for a life so far, that really lends itself to some pretty damn good stories, you know. I mean, some people don't realize that until much later in their life. And I think that it's also really really good advice to younger people who and I was one of those people and you were for a time as well think that there is honor in predictability, right, and that is sad, because actually letting go and sort of seeing where the universe takes you is a really powerful thing and, frankly, it's a great muscle to exercise, because some of the time it actually will not lead you in a better direction, and that's okay too. And I think if people say there are some people, I'm sure, out there that say you know what?
Max Chopovsky: 44:37
I'm just going to try something totally different, I'm going to take a very sort of not passive, but I'm going to try to seed some control, and their first adventure after seeding control is not a great one and they just use that data point to confirm that actually their previous approach was correct. I have to stay on the straight and narrow, as you said, and that's the way to do it. But I think, beyond the original sort of step of hey, I'm going to let go and I'm going to see where the universe takes me, it's equally important to understand that not every place it's going to take you is going to be a better place. But as long as you take something away from that, as long as you learn a lesson, that's a net positive. I think a lot of people just give up.
Gaby Darbyshire: 45:29
Well, I think that's exactly right. I think it comes back to this thing about fear and trust. So you can be afraid, but you can trust yourself to figure it out. And I think some people are instilled with fear from whatever circumstances they grew up in or things not working out, and they become afraid to essentially get back on the horse.
Gaby Darbyshire: 45:51
And I think the hallmark of my business now the word we use most often is resilience.
Gaby Darbyshire: 45:59
And we're talking about it in terms of climate resilience, because I invest in climate, companies and how to make the planet and people more resilient.
Gaby Darbyshire: 46:05
But on a human, personal level, the founders and the companies have to be resilient and you as individuals have to be resilient. And resilience to me means being prepared to expect that there will be obstacles and there will be things that go wrong and that they don't knock you sideways, that you are okay with expectation of rejection, of surprise, of uncertainty, of bad things happening, but that they don't rock your fundamental core and that you still have enough trust and faith in yourself to keep going, even when things are not easy. And I think resilience is something where it's a muscle. I think you can exercise it, make people stronger and better people and probably more humble and probably more accommodating and tolerant of other people's foibles and failings, and I think that that makes you more easy to navigate life. So resilience is really the core characteristic I would wish young people to have. Yeah, I think it's fantastic and I couldn't agree more, because too many young people to have.
Max Chopovsky: 47:19
Yeah, I think it's fantastic and I couldn't agree more, because too many young people these days are raised without resilience and that is a challenge as they head into the real world Just don't fall into the crevasse, yes, well, that does it, gabby Darbyshire. Polymath, renaissance woman and taker 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.