Be More Pirate
1. HERE BE DRAGONS
New Horizons, New Heroes
Three hundred years ago a small group of frustrated and underappreciated, mostly young professionals finally had enough of living in a society run badly by a self-interested and self-serving establishment. Disruption had become the constant backdrop to their lives as they faced ongoing uncertainty and mass redundancy in a world plagued by ideologically influenced international conflict. This generation felt entirely abandoned, and they were right. The odds were stacked high against them and in every single way, the rules of the day favored an elite few, and for the majority of people life was unclear, unfair, and unfulfilling.
Rather than simply voice their complaints, they chose instead to do something about the situation. No longer prepared to sit quietly and accept the bad deal on the table, they decided to break the rules and then remake the rules. Along the way, they came up with a new social code built on purposeful principles such as fair pay, fair say, social equality, freedom, and justice. And rum.
You see, the action these particular disenchanted professionals took was to turn pirate. Although such an extreme-sounding career change was arguably justifiable, these rebels,
who emerged from both the Merchant and the Royal Navy, were soon denounced as “enemies of humanity” by the establishment they struck fear into, not only because of their unlawful buccaneering but also because of the radical and progressive ideas they represented.
These were the “Golden Age” pirates, and they created enough disruption at the edges of society and politics during this, the dawn of capitalism, to leave a legacy that has changed the way we live forever. Which is handy, because, some three centuries down the line, we’re once again in need of inspiration about the best way to give the current establishment a metaphorical kick up the backside, to better tackle the world’s looming crises.
Today we have a similarly self-interested political and business elite pressing the buttons of power, who for the most part show no sign of stepping up to the challenge in any meaningful sense. Rather than gracefully handing over a little more authority to the generations destined to live with their mistakes the longest, the folks who have already overcooked the future continue to run the show (a) in their own interests and (b) badly.
In their defense, it hasn’t all been completely disastrous. From antibiotics to nanosurgery to the realization of the internet to lifting a billion people out of poverty to the Spice Girls, some of the progress in the late twentieth century truly demonstrated humankind at its best. But then we left the great fridge door of history open and everything started to go off. Today a multitude of futures await, most of them apocalyptic: environmental degradation, economic disintegration, unprecedented levels of human migration, or the rise of the robots—just take your pick.
In direct response to this turbulence, uncertainty, and the resulting emptiness many us face, much of society is afflicted by an epidemic of anxiety and a crisis of identity. Living costs are rising while real incomes are falling and the distribution of both wealth and opportunity grow more unequal than ever. Whole generations feel excluded from their own future. They are sick of being told “that’s just the way things are” and that they’re “naive” for expecting such basic amenities as decent housing or accessible health care or affordable higher education.
There’s a lot of people we could blame for the mess we’re in, but so far that’s got us nowhere fast. What happens next is up to us; we each have to decide whether we’re part of the problem or part of the solution, and when I say we, I mean you.
A lot of people might tell you not to worry, that technology will save us and everything will be okay in the end. But it’s not true. No one is coming to save you. It’s going to get worse before it gets better. There’s an urgency in the air and a need for change. Today, if we want to improve this picture of our future, we have to do it ourselves. The only way out of this mess is a little less Instagram and a lot more action.
The upside to an age of uncertainty is that it is fertile ground for opportunity. Most of us are familiar with the feeling that if we could just get focused, come up with a plan, hustle a bit harder, and seize the opportunity, we could do good, if not great, things. There are smart people doing interesting things everywhere, but instead of being inspired by them, we find it easy to feel overwhelmed or intimidated.
So many successful people look more like superheroes than real-life characters whose steps you could realistically
follow in. The typical role models that often get served up are well meant, but let’s face it, they’re also a little predictable. I want us to go further than the standard Stanford University dropouts with great teeth, quirky surnames, and heads full of world-changing technology. The thing is, every exciting unicorn galloping out of Silicon Valley leaves a lot of horse shit behind the scenes. I think we deserve more than the uberization of everything as our default universal future model of anything, and that’s why I’ve looked to a different set of rebels, not just for inspiration but for practical ideas that anyone can take, adapt, and implement in order to change whatever it is that needs fixing, overhauling, or scrapping.
We’re going to look back in time to the secrets of a unique set of pirates in order for you to navigate a more promising path for the future, one that sets you on the right track for the fortune you seek.
Whether you aspire to be a world-class change-maker or you’d just like a new career, whether you’re trying to make your name, up your game, strike it rich, or strike a blow to the system, Be More Pirate will help you be more courageous, more effective, and more creative as we sail into the uncharted waters of the mid-twenty-first century.
Whether you’re thinking about setting up your own business or trying to improve the one you’re already in, whether your side hustle needs another side hustle, or if all you know is that you’ve got what it takes to be the next big thing, Be More Pirate will help you be more decisive, more powerful, and more purposeful in getting there.
Why are these Golden Age pirates the perfect role models
for anyone trying to make their mark against the odds we face today? Well, they didn’t just break rules, they rewrote them. They didn’t just reject society, they reinvented it. They didn’t just tell tall tales, they told a story that shook the world. They didn’t just challenge the status quo, they challenged everything, and once the dust had settled, their alternative society and strategies changed the world for good.
Yes, these are big claims. And yes, I’m going to back them up, and then some. Over the years, pirates have acquired a mythical status. They have been popularized and presented as pop-culture pastiches that don’t resemble the true picture. Be More Pirate looks past these clichés and analyzes their innovations, organizational systems, and team structures that have become a global standard of good governance and their pioneering work on branding and reputation management, which predates the universal principles followed by best-in-class marketing and communications today. In the coming chapters, we’ll explore which of the pirates’ systems, beliefs, and attitudes will be valuable to anyone searching for treasure in these uncertain times.
We’ll learn how a sense of purpose spurred the pirates forward and that, beneath the black flag, many also fought not only for booty but also for social change, justice, and freedom. We’ll observe the economics, mechanics, and tactics that allowed pirates to take on the world, and explore how they designed a unique and dynamic system of principles to live by: the fluid but highly effective Pirate Code, which has had extraordinary influence on many twenty-first-century institutions and can now be harnessed individually by you. We’ll learn the techniques of ground-breaking pirates of old like the “Pirate
King” Henry Avery, “Black” Bartholomew Roberts, and the legendary Anne Bonny, and compare them to their modern-day equivalents such as Elon Musk, Chance the Rapper, and Malala Yousafzai. These figureheads, new and old, made their own way and amassed vast influence (and often vast fortunes) to make a huge and reverberating dent in the world around them.
Forget everything you thought you knew about pirates Before we go any further, we need to address some concerns you might be having and walk a few myths off the plank (including plank walking, because the truth of the matter is that there really were no planks or any hapless victims being walked off them).
I’m guessing the word pirate makes you think of Johnny Depp as Captain Jack Sparrow, or maybe the Disney version of Captain Hook, a slightly camp pantomime villain complete with eye patch, parrot, and pieces of eight. Or perhaps you don’t buy the “jolly pirate” concept at all, and you’re thinking to yourself, “Hang on, weren’t pirates actually complete and utter bastards who reveled in theft, torture, rape, and murder?” The short answer to that one is “no, not every one,” though admittedly there were a few psychos among them.
But before we deal with the dark side, let me make it clear that we will be drawing our inspiration from a very specific type of pirate from a very specific period of history. This is not a book about Somali pirates, Chinese pirates, or Roman, Greek, Norse, or Barbary pirates nor is it about looters, raiders, corsairs, or wreckers, interesting though they all are. No, this book draws its inspiration from those who ruled the waves from around 1690 to 1725, the so-called Golden Age of Piracy, when
a handful of what author Guy Anthony De Marco calls “rock star” pirates set the world alight with audacious rebelliousness and a clear commitment to ideals of justice and equality.1
The likes of Henry Morgan, “Black” Sam Bellamy, and the fearsome Edward Teach, aka Blackbeard, were infamous the world over for standing firm in front of, sticking a middle finger up at, and totally outsmarting the powers that be. Pirates went head to head with the world’s mightiest military forces, the enormous resources of the first state-backed multinational corporations, and the combined strength of the global superpowers of the day. And, for nearly forty years, they won.
For hundreds of years, the true and troublesome story of pirates has been rewritten by the establishment they threatened. They have been painted as “enemies of humanity,” psychopaths utterly beyond the bounds of civilized behavior, in order to distract wider society from their potentially incendiary exploration of ideas such as universal suffrage, fair pay, and workers’ rights. Gradually, over generations, as their reputation passed into myth, their stories were watered down and turned into caricatures for children’s birthday parties. Until now, when pirates are hardly regarded as progressive role models, but some of what they achieved could and should be inspiration for our times. That they have been unfairly sidelined becomes clear from a simple online experiment. Try searching Amazon books for other historical groups who emerged in response to unjust aspects of society. Search “civil rights” and you’ll find almost 100,000 robust academic results. “Suffragettes” returns a library of literature and support materials offering thorough analysis on the subject.
If we perform the same search for “pirates,” however, the first title that comes up is Pirates Love Underpants, a children’s book with an eye-patched, parrot-balancing, striped-breeches-wearing, treasure-holding, toothless grinning pirate captain on the cover. Pirate Pete and His Smelly Feet is next up, followed by more children’s books and then some romantic fiction featuring dashing captains and swooning maidens. It takes a long time to get to any actual history books, and I’m guessing I’m one of the few people who has read all of them. These frivolous incarnations of pirates do the Golden Age of Piracy a massive disservice; the charge that pirates were nothing but chaos merchants needs to be addressed, because “agents of change” would be a more accurate term. I’m going to help you open your mind in order to see past your doubts and discover the truth about the tricks, tactics, and techniques used by pirates to create change in the world.
What might your reservations be at this stage? That I’m glossing over the gory truth of pirate history or massively indulging in moral relativism? If so, then good; these would be valid concerns to have.
First of all, let’s cover off the baddest of the bad men because, yes, there were some downright bloodthirsty pirates like Captain Montbars the Exterminator, or Ned Lowe, whose most infamous moment of madness came when he captured a treasure-laden ship only to watch the jewels slung overboard
by a brave member of the captured crew; Lowe’s response was to cut his prisoner’s lips off, fry them, and force feed them back into his victim’s lipless mouth before single-handedly hacking the rest of his captives to death. It’s pretty clear that the psycho-pirates were very psycho indeed. However, they lived in violent times where torture was common practice by the military and public execution was popular entertainment for the populace. Consequently the daily remit for casual horror could be huge. But none of the psychopathic pirates made bloody by their bloody time will be featured in this book. None of them holds a place in history for much other than terrible deeds. None of them was a champion of change or a figurehead of pirate innovation.
In his smart and funny book The Psychopath Test, the smart and funny Jon Ronson explores what it means to be a maniac and discovers that at the turn of the twenty-first century the usual average-Joe-to-psycho ratio is about 1 in every 100 people.2
He reveals that among CEOs in business the normal ratio is five times higher. From the statistics and stories I’ve found of pirate crews, captains, and the overall community, it would seem that had Ronson applied his psychopath test to the Golden Age of Piracy he’d have found the same higher-than-average psycho ratio among pirate captains as he found in CEOs.
Whether it’s the business world today or the pirates’ world three hundred years ago, most people, most of the time, broadly operate within the codes of conduct and culture of the day with a handful of wackos at the top giving everyone else a bad name. Unfortunately, the wackos are always with us, but we don’t have to follow them and we’re certainly not here to
learn from them. So, having got the small selection of real nutters out of the way, let’s consider the question: How mad and bad were the rest? Well, they were pirates, which some might see as a bad start, but piracy, defined as “theft at sea,” is as old as civilization itself and has always involved at least the threat of violence. And that’s the point. The majority of Golden Age pirates tried to create the impression of violence while actively trying to avoid conflict wherever possible. I know that sounds counterintuitive but hear me out: pirates were heavily motivated to steer clear of actual violence because it made sense financially. For pirates, there was a clear case—fear equals profit and violence equals cost.
As Peter Leeson, economist and author of the award-winning The Invisible Hook: The Hidden Economics of Pirates, puts it:
Pirates used the Jolly Roger to enhance their profit through plunder. But it was the profit motive that led them to overtake victims in the least violent manner possible. By signaling pirates’ identity to potential targets, the Jolly Roger prevented bloody battle that would needlessly injure or kill not only pirates, but also innocent merchant seamen. Ironically, then, the effect of the death head’s symbolism was closer to a dove carrying an olive branch.3
To prove that this is business sense, not nonsense, let’s look at their balance sheets. Pirates had close to zero resources at their disposal to repair a damaged ship or replenish supplies. Even minor damage or loss was life-threatening to a crew who’d
be hanged on sight at the next port; they couldn’t afford to stick around too long for a tire change. A reduction in their famed speed and agility was equally dangerous: a boat with a hole in it is not convincingly threatening or a good getaway vehicle.
And then there’s the pirates’ pioneering social insurance practices. A pirate who was injured in battle received a payout from the ship’s common pot of money: 800 pieces of eight for a lost leg or 600 for a lost arm. Their compensation practice was not only a great recruitment tool and a prescient prediction of public policy and eventually human rights but also a very substantial financial reason for the company to avoid any damaging skirmish.
Another practice that proves that most pirates weren’t out to cause unnecessary violence is their treatment of the captains of the ships they commandeered. Before seeking volunteers to join their crew, of which there were many, the pirates would interview the captured sailors about the behavior of their captain. Had he been the brutal sort so many of the pirates had experienced in the navy, or had he been fair? If the answer was that he’d been a tyrant, he might find himself marooned on a fast-disappearing sandbank in hundred-degree heat with only a pistol to comfort himself. Had he treated the men well, more often than not he’d find himself richly rewarded. This example of pirates imposing their principles of good management practice could be viewed as their showing consideration for the suffering of their former colleagues. Or their tendency for revenge. Or both. Okay, maybe you’re gradually coming round to the idea that pirates weren’t always the crude, bloodthirsty thugs they’re portrayed as. Possibly you’re starting to see that they had a pretty enlightened approach to their enterprise.
But what about the inescapable fact that they traded on terror? That’s surely a bad thing, even back then on the high seas? Well, I would agree, but I think it’s essential to remember two things: first, I’m judging pirates by the morals of their own times, not ours, and, second, we need to look at the intentions behind their actions. At the time of the Golden Age of Piracy, chimney sweeping and mining were common forms of employment for preschool children and the transatlantic slave trade was a respectable middle-class investment opportunity. The point is not even so much that they were brutal times with different standards (though they were), it’s more that the self-declared good guys were abusing, stealing, and murdering. In fact, the pirates were only cast as the bad guys when they started standing up to the so-called good guys. Who were, indeed, pretty bad. For instance the infamous East India Company, the trading arm of the British government and one of the world’s first household business names, routinely used murderous violence to strike “trade deals” as part of their government- and monarchy-sanctioned proto-colonial business operations.
As Nirad Chaudhuri, an Indian-Bengali-English writer on colonialism, said, “the line that separates robbery from piracy organized by respectable and legitimate governments has always been a very fine one.”4
During the Golden Age of Piracy, depending on the state of international relations, some ships would be sailing under a royal letter of marque (a formal license to operate as an armed militia, where violence, murder, and thievery were lawful as long as a cut of the booty got kicked back to the palace). This pirate-like pastime was officially called privateering. However, if things were quiet on the international
conflict’s front and there were no letters of marque on the scene, the very same endeavor was renamed piracy. One person’s privateer is another person’s pirate.
Her European enemies nicknamed Queen Elizabeth I of England the Pirate Queen for her liberal use of letters of marque and privateers. They allowed her to amass vast wealth, discreetly sink the odd enemy ship, and lay the foundations for the British empire, all while kick-starting the Golden Age of piratical dominance on the seas. The Pirate Queen’s right-hand man in all this was Sir Francis Drake, still regarded as a national hero by the British but a hated figurehead of piracy by, erm, well, everyone else.
Throughout the seventeenth and eighteenth centuries, priorities and politics were in constant flux; the same activities conducted by the same men were encouraged and then outlawed over and over again. Legal, illegal, pirate, privateer, hero, hanged, rinse, repeat. However, there was one critical difference between these original privateers and pirates of the Golden Age and those who followed later—namely the duality of their intention. Golden Age pirates may have been thieves, but they were also incidental pioneers of social and political equality, fair pay, health insurance, workplace injury compensation schemes, and same-sex marriages, enshrined in the new rules of society that they wrote for themselves.
And it’s here we begin to see the potential power for some contemporary professional rule breaking. Pirates didn’t settle for the promise of change only to go undelivered; instead, they challenged, broke, and then rewrote the rules for others to follow in their footsteps. It’s a radical and risky path
to establish new principles, but as pirates prove, sometimes breaking the rules, and making the rules is just a matter of perspective.
The view from here might look like a moral mess, but the proof of the benefits of the pirates’ social movement was obvious to observers at the time.
This is Colonel Benjamin Bennet, in an unbiased and objective assessment of the pirate situation, reporting to the British government’s Council of Trade and Plantations in 1718, where he said:
“I fear they will soon multiply for so many are willing to joyn with them when taken. . . .” The prospect of plunder and ready money, the food and the drink, the camaraderie, the democracy, equality, and justice, and the promise of care for the injured—all of these must have been appealing.
Colonel Bennet’s voice is an official one with no agenda or empathy on behalf of the pirate cause. He was a military officer talking to an arm of government via formal channels, not an ancient “pyrate” justifying his crimes under a romantic banner. He had no reason to embellish the pirates’ appeal which was already far too clear to him. The appeal of the pirate’s new social contract had already begun to threaten the order of an outdated establishment.
The power of the unproven promise of the pirates’ new society “for the many, not the few” is a timely reminder of the fragile impermanence of our own democracy and the risks we run if it is taken for granted. I know that citing democratic
principles alongside Golden Age pirates might seem like a big leap, but I’m not alone in making the link, and it’s a link we might learn from.
The host of the brilliant and scene-setting Pirate History Podcast, Matt Albers, tells an epic tale of the Golden Age pirates in beautiful detail across weekly episodes like this:
It would be difficult to say that pirates began the first democracies since ancient times, but it wouldn’t be totally out of the question to say they influenced [them] . . . and this was a very grave threat to the old empires. A group of rough and uncouth men, in a very couth age, decided that they were going to disregard the old order and try and start something where everybody had a voice. This was a threat to everybody in Europe. . . . They knew what a threat they [Golden-Age pirates] represented and they had to do everything they could to make sure that nobody ever in the New World would think like that again. Only about fifty years later there was a group of very genteel men in North America who had very similar leanings.6
To Matt and me, it would appear self-evident that pirates played a real role in both the formation and the fight for US identity, democracy, and independence, and it’s this role of the rule breaker, in defense of democracy, which might just be another reason to reconsider their status from rogues to role models.
The Golden Age pirates’ intentions are what challenged and terrified the official powers, and it’s the disruptive effect of
their promise of a progressive alternative to the established and unfair order that makes them worth learning from now.
Having established that a part of pirate history could provide advantageous yet underexplored inspiration for the world we face, we’re nearly ready to set sail. In the next chapter, we’ll Ctrl.Alt.Delete pirate history for good as we explore the pirates’ innovative ideas and practices that can be valuable to those of you seeking treasure in these uncertain times.
In Part Two you’ll learn how to be more pirate yourself and carve your own success by following their five simple stages of change. In researching and exploring the pirates, I’ve identified five key methods that they practiced, and developed a framework for you to be able to use them, too. These fundamental stages that underpin a pirate mind-set for creating change are:
1. Rebel—Draw strength by standing up to the status quo.
2. Rewrite—Bend, break, but most important rewrite the rules.
3. Reorganize—Collaborate to achieve scale rather than growth.
4. Redistribute—Fight for fairness, share power, and make an enemy of exploitation.
5. Retell—Weaponize your story, then tell the hell out of it.
The pirates questioned and challenged the established order, rebelled against the status quo, and then rewrote the rules. They came up with better alternative ideas and formed powerful communities of people who wanted to reorganize themselves in a new society. In these pioneering groups, the pirates
made a point of fighting for fairness and inclusion. As they did this, they weaponized the art of storytelling and anticipated the idea of branding, crafting killer stories about themselves that helped magnify their reputation and establish their legacy. Of course they did all this alongside the rum, plunder, and looting you’re more familiar with, but it’s these five techniques that will be your basis for creating a Be More Pirate state of mind. In each of the five chapters that explore these behaviors we will keep checking in with the very best examples and achievements of groundbreaking pirates like Ben Hornigold, “Black” Bartholomew Roberts, and Mary Read, and inspirational modern-day pirates like Banksy, the Wu-Tang Clan, and Blockchain. Drawing on a mixture of pioneers old and new, you’ll understand what it means to be more pirate and be shown how to adopt a piratical approach of your own. Takeaway sections at the end of each of these chapters will help you to think about what being more pirate might look like to you and how you can start to be more pirate in different areas of your life.
In order to help you apply these learnings to your life, Part Three will focus on the Pirate Code, the famous but misunderstood rules that governed each pirate enterprise. We’ll look at how these codes helped the pirates establish their purpose, priorities, and principles and how you can harness their exact structure to build your own Pirate Code 2.0, a bespoke manifesto and mechanism to set you up for the success you deserve in the twenty-first century. Soon you will have an arsenal of surprising and invigorating pirate stories, you’ll be armed with cunning pirate tricks and tactics to turn your ideas into action, and you’ll know how to put more meaning into your mischief.
Be More Pirate will help you realize your inner ambitions and overcome your fears, make you more ruthless at bringing your ideas to life, and give you the confidence to fly your own flag and stand up for what you believe in. As we start to approach the end of the Information Age, the future is uncertain and nobody knows what’s over the horizon. But it is certain that what you stand for will count more than ever, and who you stand up to will come to define you.
As we sail into the uncharted waters of the twenty-first century, where the odds once again favor the few, we need to take change upon ourselves and follow in the footsteps of pirate pioneers who took on their broken systems and fought for fairness as well as fortune, and changed our world by breaking and remaking the rules.
I know that for some of you embarking on a course of rule breaking might sound a disconcerting way to get things done, but consider this: great rule breakers are often like great painters, rarely appreciated for their art in the moment. How many statues are out there of people who were just following orders? History tells us time and again that progress depends on the rule breakers. And here we are again, living in historic times when the hour is likely to be upon us all when we have to decide if it’s the right thing to do, to do the opposite of what we’re told.
It’s time to take courage. With those ideas of yours, that phone by your side, and this book in your hands, you have all that you need at your fingertips. So forget your preconceptions of pirates and have no fear about what’s to come. If you’re going to reinvent your future, it won’t be by doing what you’re told but by rewriting your own rules and being more pirate.