Dana Safa Bernardino
On this episode of the Bring It In podcast, 1Huddle’s CEO and Founder, Sam Caucci, sat down with Sam Conniff, author of Be More Pirate: or How To Take On The World and Win.
Sam is a British entrepreneur, co-founder of Liberty and Digify Africa. Sam’s insights from Be More Pirate: or How To Take On The World and Win takes us back to the time of the best pirates in history. He speaks about how we often have leaders of organizations that are out of touch with their employees.
Sam emphasizes that in order to have a successful business, leaders must look through the lenses of their employees to discover what may be holding their business back. Sam’s book depicts how embracing pirate culture could be the solution for the future of work.
Audio available on Apple Podcasts, Google Podcasts, and Spotify.
Below are some of the insights Sam shared during our chat, edited for length and clarity. You can find more Bring It In podcast episodes here.
Sam Caucci: So Sam, why’d you write Be More Pirate?
Sam Conniff : Because I was very annoyed and growing increasingly bored with the conversation in work about change. It struck me having done God knows how many hundred away days to talk about change. People stick Post-It notes on the walls, call the same thing a different name, talk about innovation, and then go back to work and do exactly the same thing, putting all their ideas into an email or two, where everybody knows good ideas are sent to die.
So, eventually I decided that perhaps… maybe, rather than it be an irresponsible thing to do to break the rules, it might just be the responsible thing left to do to bring about any goddamn change. And I was trying to find some good examples of people who were great at breaking rules, and who is better than the pirates at not just breaking rules, but making new rules.
Sam Caucci: Why pirates?
Sam Conniff: I’ve been an entrepreneur all my life. Reluctantly the first half and enjoyably the second half. And I would often use pirates as a metaphor, as a kind of euphemism for get up and go zeal. And I’m sure lots of owner managers, lots of people who’ve done their own thing will have some kind of story they say, you know, or some kind of proxy, you know. What we’re going to be, we’ve got to get up and go about it, whatever it is.
Mine has always been pirates. And as I was leaving my biggest company, my longest running company, it had been a big part of my ego and my identity for many, many years, and I knew it was time to go, and I knew I needed a vehicle, right, for leaving that thing behind. So I thought I’d write a book.
I got a chip on my shoulder. I didn’t go to school or I didn’t go to college, what you would call school, and dyslexic and just always wanted to write books, right? So I started writing the most boring book on earth. I started writing the book that I thought was the grown up book having run my own businesses since I was a teenager and I was leaving this place as I turned 40 and it was like, right, okay, I’m going to do something grown up now because running my business and always saying that I was always the imposter. It was always too much fun. Even when it wasn’t fun. And so I thought this is me, right? I’ve got to do something growing up.
So I started to write a book about business, about my perspective on business. And it was the most boring book I think has ever been written. I got 20,000 words in. I’m not a business guru or a business leader, like my interest, my main interest throughout my life has always been entrepreneurs and entrepreneurial circles. And I read it to some colleagues and some guys I mentor and coach in entrepreneurial spaces, and they were like, “What the F has happened to you, man? Well, where’s all the, you know, where’s all the stories? What are the adventures you’ve had? Where’s all the near death experiences? Sam, where are all the pirates?”
And I’ve got, you know, I’ve got loads of stories, lots of experiences and loads of, you know, lucky, takes on things. And I went back to my desk and thought, yeah, where are all the pirates? And then I thought, why do I always talk about pirates?
And then I thought, you know what, I probably need to actually justify that. Like, people who call out their heroes or, you know, we cite, you know, people reference everyone from Gandhi to whatever. Like, who really knows the full, deep story? And so, because I was having increasing amounts of time on my hands as I was exiting the firm, I went to the British Library when I started to read about the true history of pirates. And It was like getting a slap in the face, right?
You spend your whole life thinking it’s Jack Sparrow and Captain Hook, and then you discover that the true history of pirates is not what you ever knew, and it couldn’t have been a better metaphor for the thing you wanted to learn. And honestly, then, for the next like nine months that I wrote the book, I was in a race against all the people in my head who must have made the same realization that I have who’d stepped on this bit of history that was otherwise unearthed.
And I thought, surely someone else is going to draw this analogy, but luckily I made it to the finish line first.
Sam Caucci: I mean, I got the book here and it’s marked up pretty good to be honest with you. So that’s a good thing. Do you have a favorite pirate? After going through everything you went through, is there a favorite pirate favorite pirate story you have?
Sam Conniff : Yeah. Anne Bonnie. She’s just got to be the one. She’s just incredible. This you know, very relatively, you know, mixed status, the life everyone, you know, kind of has. She almost is born in privilege, but she squanders the privilege. Her dad has an affair with the maid. You know, it’s just a brilliant story of like the English class system at the time, what’s totally unacceptable, you know, shunned for having an affair with the maid or what it’s all about.
And, and my guess is that she has, and because pirate history has to be interpreted, right? She has a realization of how unfair the world is. And with this, she has a fight, with her stepmother. She takes a knife to her step mom, her dad’s in love with a maid. She wants to champion love. She ends up running away, jumps on a ship, finds her way to the East Coast of America.
And then she’s just a tear away, right? She’s an absolute hooligan. But this stunning redhead Irish woman. And then Jallet Captain, Jallet Calico, Jack Rackham, one of the most famous pirates is coming down the Eastern seaboard causing mayhem. And he was like a real prince and all the stories about him and stealing clothes to get dressed up in his fineries and a remarkable guy, and actually allegedly, quite the entrepreneur because he’s one of the pirates that made the skull and crossbones, their brand.
And actually understood the idea that this brand stood for something and knew that it had a message. And they, they partnered up and they became this unbelievable–, they were like the Jay Z and Beyonce of the pirate world, like, you know, unstoppable force.
And she would lead from the front. There’s these stories of them under attack and she’s there, two pistols on the deck whilst everyone else is diving beneath. And she just continues on and then her story ends in this amazing, finally Jack gets captured. She, there’s this great legendary line that she tells him he’ll die like a dog because he couldn’t fight like a man and she’s still fighting.
Uh, and then she escapes prison at the very end of it. No one knows whatever happened to her. It’s like an utter movie. And if you throw in the bit with Mary Reed, who’s the other, famous female pirate and they both had to cross dress. Did they have an affair? Like, it’s just phenomenal.
Sam Caucci: You know, one of the things in the book that stood out to me is, you know, I picked it up having a bunch of pirate books on my shelf.
Immediately the book grabbed me talking about, as a leader, or an entrepreneur, a human, that kind of caught me as I started to process the book. And one of the things that stuck out to me was that I never thought about this way was how pirates were, they weren’t, I mean, the position that a lot of the story, you know, a lot of the, they were taught, a lot of the tales were, were expanded on or in many ways they had a marketing story or a brand story that was, you know, I think, was it was of the pirates mentioned, uh, had never actually been on record murdering or, or there was no violence on record from directly from him.
And yet they were really good storytellers.
Sam Conniff : Absolutely. I mean, the story I think is really the power of it. And the story is the power of any business. I mean, we know the essential ingredients are the people, the money, the culture and the customers. But it’s the stories that we tell determine as much as anything, our potential for growth the people that follow us.
And I think really importantly, talking to people who. are part of their business have a stake in their business, whether that’s financial or emotional, the story that you tell yourself about your business, your business is a story of you, right? You know, every story is an externalization of our identity.
And what I’ve found having gone through a couple of businesses, the story you tell yourself about the businesses you’ve had, the success and the failures becomes very important part of who you are. And certainly it’s the pirate success. That is their stories. Anne Bonny’s story, picking back on her, she was an amazing picture of her, you know, with one of her chest semi bare, her hand raised with a flag, the other with a sword.
It’s the exact same image of Lady Liberty leading the brave, which is the famous, famous picture of Les Miserables, right? And the book which had her etching in, it was called A Famous General History of Pirates, was found in the studio in Paris of the painter of that iconic image, which becomes Les Miserables. And then the image of Les Miserables is the most famous relationship that has is, of course, with the Statue of Liberty.
Now, that is not causal history, but, you know, there’s more than a correlation line there, and it’s about the stories. And it’s known that Anne Bonny’s story was told amongst the proto feminist literary circles of London, you know, that led to the suffragettes movement. And exactly the same, yeah, Blackbeard is the guy you’re citing.
Like, there couldn’t be a more famous pirate than Blackbeard. No record of him killing anyone whatsoever until the day of his death. And what makes it interesting is you go the other way with Blackbeard. He’s so famous because he really invents this icon. So the story goes, he was so committed to the pirate brand, he would set light to sulfurous fuses that he’d tie into the ends of his beard.
So when he appeared on the horizon, or climbing aboard your ship, you know, it was like absolute hell bearing down on you. And what better representation is that of someone taking a brand idea, living it to the full and then driving the bottom lines. If you don’t have to kill anyone, you know, there’s a massive profit increase, you know, you’re, you’re receiving less damage, you’re giving less damage and there they were, they were.
And this is the big mistake. Pirates exist on the long arc of certainly the English working class, but the English working class have a role to play in the long fight for equality and rights. And you can trace the dynamics of that through the trade union movement, the civil rights movement to suffragettes and fight for equality and rights that’s still ongoing and hasn’t been completed.
And what perpetuates them isn’t the fact that they were pirates. You know, that’s like the levelers or the chartists or any one of those, those important chapters that they told such a damn good story. Like, that was their real power, that people followed them, and we’re still to this day, they’re a multi million, million pound franchise, right?
There’s something about the romance, the idea, the individual against the enemy, and who doesn’t want to sometimes just pull out, you know, their cutlass and swashbuckle their way through the red tape bureaucracy and just general nonsense of life? Like, of course it stays with us. And that, my argument is, it was intentional.
They designed that. It was theatre.
Sam Caucci: So today we have great resignation, you have quiet quitting, you have boss loss, I’ve heard quiet hiring is one now. And I even heard, I think I heard two in one week, I heard quiet hiring and I heard rage applying this week, which is the next one. They’re just coming out all over the place.
And I gotta ask you, because you think about this, you work with brands, you work with leaders. The stories around work right now feel like more Royal Navy than pirate. I guess how do you connect what’s happening in the workforce right now from organizations who maybe built themselves up as pirates who were kind of almost going from revolving the other way.
Sam Conniff : Yeah. I think that’s certainly the case. And we can name check a few, you know, the big kind of pirate brands, you know. Steve Jobs famously called on the pirate brand repeatedly. They they flew a skull and crossbones over Apple HQ on the day that he died.
I don’t think there’s anywhere in the world that could say that Apple behaves like a pirate organization now. They certainly set the tone, right? And they’re way ahead. God, does it feel like a pirate? And so do is the Pirate Association, therefore, the upstart, the challenger, the new story, the story that drives innovation, perhaps.
And is it necessary and kind of noble for the larger organizations to kind of fall into these tracks of quiet quitting? And I think the story is bigger than all of that. And I think those kinds of slightly trite titles will be misleading. Always. My guess is that in a time of like, really tough change, change that’s outside the experience set of most leaders.
We as humans struggle with that, right? So we look for narratives. There’s a really great study that in times of uncertainty, human beings will choose an electric shock over the possibility of an electric shock. Like we really hate uncertainty and change so badly, we’d prefer the pain. And you see it, right?
In times of great upheaval, people will go through extremes of politics. We will, you know, the backward looking narratives of build back better and new normal, you know, that feels like something I can believe in, right? Rather than take the moment of this profound fragility to do something differently.
And what I’ve been looking at, because I think Be Pirate More Pirate got a lot of people to the place of change, but then when you actually make the change, it becomes quite scary. And, Being More Pirate allows you to do that. And, and as I look back on the success of Be More Pirate, I think it’s a bit like a fancy dress party.
You know, fancy dress parties are like, they’re like 15% more fun than any other party because you get to pretend you’re someone else, right? You do a few things that you wouldn’t normally do. And that’s really what I heard back from people who’ve been really successful be more part. They just took that bit extra risk because they were being cavalier.
They were calling themselves pirate and it was like a mask for the time. But in really profound change, you know, I met people who didn’t know how to navigate. And so one of the things I’ve been studying as I look increasingly at leaders selling, peddling these backward looking narratives or observers using these trite and really unhelpful terms.
I’ve been looking for leaders who have excelled in uncertainty, and it’s interesting because it’s something you said about people, you know, the workforce you walk by the more I looked at our own political leaders on the daily news over the last two years, and some of the narratives coming out lots of business and peddling this false certainty or backward looking stuff.
I started interviewing people gone through the experience of being refugees and then started their own business. People who’d been on the streets and started their own charity. People who’d run gangs and are now running business. People who’d been prisoners of war. And I’ve got this real idea of uncertainty experts.
And it follows on in my head from the work I did with Pirates, because I’m always interested in innovation from the edges. But we overlook and misunderstand millions of people every day who are experts in uncertainty. In the UK, there’s like, there’s 12 million people in poverty, which is 20… percent of population.
There’s 1.2 million homeless. There’s four million single parents. There’s 216,000 young adults in gangs. I mean, compared to your populations, this is crazy figures, but every single one of them masters uncertainty every single day. You know, it takes a fucking hell of a lot of tenacity and wisdom and knowledge and experience and balls to get from the beginning of the day to the end of the day, depending on your circumstances in some of those areas, right, they nail uncertainty and they don’t depend on backward looking ideas, there’s deep innovation happening.
So my interest in pirates has led me to a rather interesting place in uncertainty, which is a long way of saying I generally tend to ignore those explanations or those titles, because I think the weakness in the titling that’s being given is a demonstration that the observer doesn’t understand what’s going on beneath the situation.
Sam Caucci: I had a call with an HR person the other day. We were in conversation about how they advanced their software stack for workforce development. And by the way, on their website, one of their core values is innovation. And they ended up choosing a platform that was like a desktop product that only a certain amount of people could access. And they’re a restaurant brand, so heavy frontline, heavy, you know, low wage workforce that are, you know, definitely have a smartphone in their pocket, but are moving quick.
And her reaction was, yeah, so what? We’ll work with the, you know, we’ll work with what we got.
Sam Conniff : Yup.
And it’s this feeling, like you mentioned, there’s this feeling of those that get paid the least often pay the most, they are in certain societies. What story do we need to tell to get people to see those workers for more than just expendable or the first ones to go when it’s time to, you know, lay off or cut back?
In my experience, the best answers to the problems organizations face come from the people who are closest to those problems. So, you know, we’re talking about infrastructure or logistics, you know, we’re talking about the kind of efficiencies that the external consultants or whatever will be coming to be able to avoid.
If you look at it from a spreadsheet, you’ll often find numerical answers, but if you end up speaking to, I don’t know. The last time I did this exercise, it was a guy called Hans, and Hans actually sat next to the problem. And he’d sat next to the fucking problem, excuse my language, he sat next to the exact problem for the last three years.
And Hans had never told anyone what the answer was, because he didn’t believe anyone was going to listen. In the back of his mind, he thought if they did listen, they’d probably steal his idea. And so he continued his job inefficiently, well aware of it, and at the pub afterwards with a drink, maybe he’d talk about his answer and idea, you know, there’s an ideas box, you know, not, not too many meters away from Hans’s daily existence. And probably, and I don’t know the instance of this, what was paid to the consultants who came in to find innovation that didn’t get to the actual problem. Han watched them come and go.
I don’t, you know, this is a genuine story. I won’t name the company because they were clients of mine, and they did do good work, and they did let hands put the innovation in place. But it’s a true story, and it’s not an unusual story. But it’s a kind of caricature of where I think often happens.
If you want to know what’s really going on, the best company, the companies that I really love working for them, but there’s a firm called Nando’s in the UK. I really enjoy working for them. They’re doing really well, they’re expanding a South African firm. And you cannot, cannot get management position unless you do the shop floor.
You just can’t, they won’t let you do it. And then, on a regular basis, you’re back in the kitchen. And, you know, this is my belief, one of my first ever, well, my first ever roles were all front line. At McDonald’s, you know, reception, front of house, a bar, bar back. And through my business career, and I never actually fully executed it, but my belief was, if you want to get a senior role here, you’ve got to go and do a week on the front. Whether we’re, you know, that’s the bar or the door. I’ve been a doorman, you know, and it is in those experiences that you change your perspective and it’s far too easy to forget that if you haven’t had it.
So I think the answer is huge and the innovation that we need very often, the innovation that I think that changes businesses lies at the edges. So go and speak to the guys and girls who are at the edge. You know, the answers will often be there. If they’ll tell you the truth.
Sam Caucci: I think I even read in your bio that, you know, you worked in the restaurant industry coming up a little bit.
You had a stop. I had read Devil in the Kitchen.
Sam Conniff: Yeah.
Sam Caucci: A bunch of months ago with Marco Pierre White.
Sam Caucci: What was it like to be in an environment like that?
Sam Conniff: Ah, I was there very, very shortly. I spent a year and a half in kitchens, but they were very colloquial and local. I had a kind of love affair with what I thought was learning to chef with this insane family restaurant.
The stories there were just unbelievable. She’d once been Miss Barbados, the woman who runned it. And she never let you forget it. Like 20 years before, they’d never let you forget it. She was on her third husband. He used to drink beer out of teacups all day long. It was just the best ever place.
And so I kind of mistakenly fell in love with kitchens and what you can do. And I ended up running the, you know, running the kitchen, certainly designing menus, cooking. It was great. And then I thought, right, it’s my time to leave. I’ve got to go to the big city, you know, and this was just in South London.
And so, I thought I could do it. I can be, and at the time I was running nightclubs and events. So it was a great life. It really was a lot of fun. And I thought, no, I’m going to do it. I’m going to go from being a proper chef. And I got a job in a market, pure white restaurant. into that kitchen, completely different world.
You know, you’re just at the beginning, you just do prep. You just, just do, you just do practice, make everyone else’s food. And I just couldn’t handle it, man. I could not handle it. And this is 20 years ago. So the misogyny Like it was out and out, outrageous and the misogyny, racism, prejudice. The humor, let’s call it that if we’re trying to be generous, but it was a tough environment and I’m a, you know, I reckon I’m fairly thick skin.
I’ve had my near death experiences more than, more than most, but this was just like, wow. And then this huge break between the serves and that’s just the amount of booze that would get drunk between the serves and then the amount of booze that we get drunk after the service. I mean, it was a hardcore existence.
And actually what I loved, what I’ve always loved is making things. I love an empty plate and a half stuck fridge. And I like the freedom to do that. And I could not, the complete honest truth is I couldn’t hack being on a supply line, just making the carrots today. And under that pressure, man, I didn’t last more than about two weeks and one day.
So just under the amount of time I did at McDonald’s.
Sam Caucci: And a lot of people listening are in the hospitality sector and they’re running kitchens or front of house and, or trying to scale businesses. You mentioned working with Nando’s. I guess what’s one piece of advice, maybe you have, or maybe one pirate thing that a business leader in that world should employ today, again, given the climate, given the wage circumstance, given the given the economic moment, given where work is going, given how food is almost, you know, now you’ve got Top Chef season 400 coming out, you know.
So in London, by the way, what’s a piece of advice you have for a business leader that you think they should incorporate?
Sam Conniff: So that stayed with me that experience and that difference between in a kitchen environment where I felt like I had, you know, agency and capacity and control, and then being in an environment where that was taken away from me.
And I just didn’t feel like I had any say in what was going on. And it stayed with me profoundly. And so whilst I didn’t meet them out on that one, I certainly didn’t lose any respect for the people I work with. I found it, if anything. And I’ve always had that. And it’s, it’s left me with a skill, probably the thing that I’m most proud of, I would count myself fairly multilingual in business world.
And so every single business I’ve had that I’ve scaled or every bit of consultancy that I’ve done, it’s been that interplay, it’s actually the story that we just told, and it was, how do you take ideas at the edges and bring them back to the boardroom where decisions are made? And how do you celebrate that?
So that the people on the front line, on the shop floor, on the door, know that their ideas are being listened to. Because like I said earlier on the problems in a nightclub with capacity and getting people in efficiently and making money, you know, the girl on the door, or the guys that are the security, but they’ve worked it out months ago.
And then you’re there trying to work it out with a spreadsheet a while back. And that process, of getting ideas from the front line whilst they’re being knotted through, that’s where we, you know, that’s what play is, you know. It’s the exploration of how we often come up with our best thoughts.
And then there we are struggling, stressed. We haven’t met the targets. You know, we’re kind of always, there’s a lag with the problem. The problem has been bubbling along. The spreadsheet tells us it’s too much. And then we come up with a solution that’s based on a spreadsheet, which means it will be a cognitive based decision.
But the emotions, the new ones, the instinct, the intuition, everything that makes the best of human judgments is taking place at the epicenter of the problem. So I cited Nando’s and I didn’t know this question was coming out of genuine respect and I know how much innovation comes because time and again, they’re back on the shop floor.
So I think, where there’s capacity to the–, and I’ve done it when I was CEO of a 150 person, multimillion power business. I did deliveries, I did warehousing, they’re packing the unpacking. I catered for the entire team. I did two nights as a security guard. I regularly put myself back into that environment.
And it wasn’t just to kind of show that I’m one of the guys. It was to have the trust so that the guys and the girls absolutely would trust me to bring their ideas to me. Because I think that’s the most difficult thing. You can go down on the shop floor and I’ve done this with lots of CEOs taking them down to the factory floor and they won’t be told the truth.
You know, it takes a while to get that trust. So it’s not just the exercise of trading places, it’s doing so in a way that the communication channel is there. So the ideas that you’re missing that only show up on a spreadsheet down the line when money’s being lost. And they’re going through some smart guy’s head who’s watching this problem day in, day out.
So that’s the advice. Try and build that channel of communication and trust.
Sam Caucci: Love it. Sam, I appreciate your time. Last question for you. You know, we’re talking about future of work. What’s your hope for the future of work?
Sam Conniff: It probably follows on this idea, right? There’s a guy I know and he started a business called Sideways Six.
And it’s not business involvement, there’s no plug. But it suggests where this can go and sideways. It is like the old ideas box, but he’s digitized the ideas box and that trust network. And in the organizations that run it, it comes up– it’s like on your you know, you can have it as an app, if you’re in a kitchen, you can have it at a workstation.
And because it’s there and it’s ever present and because it’s slightly anonymized and it’s listened to you have this really amazing moment when new initiatives are started, you know, changes are made in something that’s tiny to the, to the, the exact but makes the biggest difference in the world like the day of payment, the hour and time of payment or the method in which is paid.
And so I see the future of work. There’s already a lot of thinking about the kind of hierarchies of it, but I’m really into this idea of splitting of the responsibilities and the decision making. I think the sense of agency that I have a say and a role in this thing that I’m listened to, it’s easily said, and I think it’s, you know, it is bandied about. But as the kind of war for talent comes along, as you know, in the UK there’s been a huge shift in the kind of workforce we’re talking about because of Brexit.
So there’s huge challenge getting the kind of skill, charisma, you know, there’s knowledge, language that’s needed on the shop floor, front of house. And when that happens, that sense of belief that I am a part of the function here. And, you know, it’s a cliche, it can be oversaid, but it’s, but it’s all important, but it has to be proven.
And so I get really excited when I see one of my outmost out there predictions is not just that kind of trading places moment I was talking about, but would be like real long term functional job splits. So, you know, it excites me when I see organizations who have lay people on the board. So they’ll have, you know, when I worked in youth development for young people, you’d make sure there were always young people on the board.
If it’s a business that’s, you know, majority of his revenue comes through front of house or front of shops, having those guys on the board, genuinely finding ways for this decision making to take place, whether it’s, CEOs and C suites spending real time on the floor, whether it’s techniques like Sideway Six, which digitizes it, or this kind of split role future that I think would be really really exciting way of seeing it.
But ultimately, yeah, it’s going to be about sharing of decision making, sharing of agency, and whether we mean it financially or emotionally, some degree of ownership to.
Sam Caucci: Sam, I love you. Got to end on a pirate quote, you got a pirate quote.
Sam Conniff: Yeah, my favorite line or thought that comes out of that book is that whole one about the biggest mistake that we can make is thinking the way things are is the way they have to be. And whenever you hear someone say, in response to your question, why don’t we try something new? Why don’t we do something different?
When they say, we’ve tried that, it didn’t work. That, my pirate friends, is the direction in which to go. Let that rail against you as we stand for doing something differently. Because, you know, I no longer think from writing that book and seeing the change, that breaking rules is the risky thing to do.
With the right people around you and the right intention, it’s become the responsible thing to do. It is upon us to rewrite the rules of business as they currently stand.
Sam Caucci: Sam, appreciate your brother. Great to meet you.
Sam Conniff: Really, really nice meeting you, man. Please stay in touch, Sam.
Topics Discussed: Future of Work, Leadership, Pirates, Training
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