You’re in your mid-twenties. You have a job at a big important company. The pay is alright, but your boss is a tyrant. He treats you like a dog. He squeezes every hour of labour from his employees… and then some. You’re exhausted. You’re fed up. So you start to pay more attention to your colleagues. You hear them whispering about a friend of a friend who just got a new job, down south. It’s a new industry, they say. There are “plenty of risks” involved, you’re warned — but the weather is nicer, the pay is better, and best of all, there are no tyrannical bosses. “The working environment is much more relaxed,” they explain. “You can work whatever hours you want… you can wear whatever you want… but that’s not even the best part.”
Your ears perk up.
“There’s free liquor for all employees, and you’re allowed to drink on the job.”
It might seem like a stretch to compare the social organization of a modern technology startup to that of an eighteenth-century pirate ship. Startups leverage technology to make their fortunes; pirates leverage terror. (There’s also a dire lack of eye patches, parrots, and peg legs.) But if you dig deep enough into the social structure of both organizations, you’ll see some uncanny resemblances. Both startups and pirate ships are largely composed of workers fleeing “traditional” companies with rigid hierarchical structures. They are typically more generous with employee stock options. They are markedly more tolerant (gladly inviting anarchists, women, and minorities to join their ranks.) And, yes, both have free beer on tap.
The resemblances are far from coincidental: the social conditions that allowed pirates to take up a life of high seas banditry are eerily similar to the social conditions that inspire today’s Wall Street quants, Cambridge coders, and Midwest middle-managers to quit their jobs for life in tech oases like Silicon Valley, Seattle, and Austin. What are those conditions? And why is it that an organization of lawless criminals could equal — and even surpass — the economic performance of ships backed by governments and rich investors?
The answers, it turns out, not only explain the phenomenon of pirate collaboration. They explain why “anti-establishment” organizations are structured so similarly. They explain why organizational structure is often more important than the amount of money (or weapons) at your disposal. And they explain why “disruptor” organizations aren’t just reviled — they’re feared.
For the sake of simplicity, we’re going to stick to seventeenth- and eighteenth-century pirates in this piece. That’s not to say that these pirates were the first to take the seas (records of piracy go all the way back to ancient Egypt), or the last ones either (looking at you, Somali Blackbeard.) The first reason it’s simpler to focus on seventeenth- and eighteenth-century piracy is because it’s the era with the largest historical record. We’re lucky a written record even exists, since pirates were mostly illiterate. The second reason it’s simpler to focus on this era of piracy is because it had the most sophisticated pirate organizations. The years 1650-1730 are referred to as the “Golden Age of Piracy”, with large boats, epic battles, and record hauls of treasure. The Golden Age of Piracy is the period that has had the largest impact on our cultural memory, too — it was during these years that the legends of Blackbeard, Captain Kidd, Bartholomew Roberts, Madame Ching, and Captain Morgan were forged; when stories of “buried treasure”, “walking the plank”, and the “Jolly Roger” first appeared; where inspiration was sought for books and movies like Treasure Island, Peter Pan, and Pirates of the Caribbean.
Why sailors became pirates
Pirates didn’t enjoy a great reputation among law-abiding society. They were violent, sacrilegious, and heedless of authority. They were known for torturing captured captains, sinking ships for the fun of it, and using language so foul it could spoil your appetite. They were, when caught, almost always hung from the gallows. Why, then, would a rational person ever choose to join the ranks of these floating, godless barbarians?
In the Golden Age of Piracy, more than 4,000 sailors decided to become pirates. This was a huge proportion of sailors, relatively speaking: the British Royal Navy had an average of 13,000 sailors between the years 1716 and 1726, with the pirate population sometimes exceeding 15% of its manpower. Surely, then, not all pirates were crazy, anarcho-sadists. There must be a social explanation for why so many men and women “jumped ship”.
As respected pirate historian Marcus Rediker explains, sailors “faced discipline from their officers that was brutal at best and often murderous. And they got small return for their death-defying labors, for peacetime wages were low and fraud in payment was frequent.”
Consider the “Cat o’ nine tails”, a multi-tail whip that was used to punish insubordinate sailors. Admiralty law meant officers could use corporal punishment; whips, tackle, bottles, canes, and other blunt instruments were put to creative use to maintain order on board. While sailors did enjoy some legal protection from abuse on naval and merchant marines, the law usually privileged officers. No wonder some sailors concluded “they had better be dead than live in Misery”.
Corporal punishment, combined with wage theft, bad food, cramped quarters, and long hours created an environment ripe for insurrection. While not all officers were bad, long trips at sea could turn otherwise reasonable people into crotchety despots. Labour relations on ships were thus unusually strained, with the first recorded “worker’s strike” occurring in London in 1768 when a “sailor and his mates went from ship to ship, striking — lowering — the sails in an effort to make merchants grant their demands.”
Strikes were just one of the strategies that sailors developed to prevent officer abuse. Others included “desertion, work stoppages, [and] mutinies.” But the most dramatic — and profitable — strategy for rebel sailors was to turn the vessel into a pirate ship.
Ships could spontaneously “go pirate” after a sailor insurrection, but more often than not, ships went pirate after being captured by other pirates. Once a vessel surrendered (sometimes without a fight), the attacking pirates would board it and take what they wanted — which sometimes included the ship itself. It is estimated that during the Golden Age of Piracy about 2,400 vessels were captured and plundered. Not a bad haul for the 4,000 people who “went pirating” during those years.
This was a crucial aspect of pirates’ social organization: start-up costs were incredibly low. Like today’s software companies, which don’t require large capital investments to get started, pirate ships could be “founded” on little more than a hope and a dream (and a couple shakes of a cutlass.) The relative ease with which vessels were captured meant pirates could split and form new “companies” whenever they wanted to — unlike a naval or merchant marine, which required big upfront capital investments. Dissent was thus much more acceptable if you were a pirate: you didn’t need to use violence to silence dissenters, you could just capture another ship and send the dissenting factions on their way.
But why were new ships so “easy” for pirates to capture?
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Why pirates thrived without government
Thomas Hobbes famously declared that life without government would be “solitary, poor, nasty, brutish and short.” Pirates provide an interesting counter-example. Their lives were admittedly short: 10% of all pirates were hung from the gallows, and those that weren’t were often killed in battle, prison, accidents, or by disease and suicide. A pirate’s career usually only lasted a couple of years (at best) but this short life-expectancy wasn’t radically lower than, say, a navy sailor’s during wartime.
A merry life and a short one was thus the common refrain among pirates, who enjoyed lives that were neither solitary, poor, nasty, or brutish. Comparing life as a working sailor versus life as a sea bandit, Welsh pirate Bartholomew Roberts pointed out:
In an honest service there is thin commons, low wages, and hard labour. In this, plenty and satiety, pleasure and ease, liberty and power; and who would not balance creditor on this side, when all the hazard that is run for it, at worst is only a sour look or two at choking?
As a sailor in the merchant navy, Roberts’ wage was £4 a month. In three years as a pirate captain, Roberts captured more than 400 ships. He plundered sugar, tobacco, gold, jewels, and (during one memorable heist) 15,000 pounds of silver. He loved getting that booty.
But the booty didn’t just go to Roberts. One of the other fundamental aspects of pirates’ social organization was its egalitarianism. Merchant ships were financially structured like big corporations: most of the profits went to the investors, a small sliver of equity was given to the captains, while the rest of the workers were paid meagre wages. Workers thus had very little incentive to defend against pirate attack — getting conscripted by pirates meant better meals, better wages, fairer treatment, and all the day-drinking your liver could handle.
Pirate egalitarianism was no day-drunk gag, though: pirates took it so seriously, it was enshrined in constitutions. Pirates struck up articles that outlined the distribution of plunder and meals, compensation for injured sailors, punishments for being violent to other pirates, voting procedures for electing a captain (who could be deposed at the crew’s will), and other checks and balances to guard against captain predation.
As pirate economist Peter Leeson argues, “pirates’ system of constitutional democracy predated constitutional democracy in France, Spain, the United States, and arguably even England.” Not even Greek democracy had the liberal sophistication of pirate democracy: captured slaves were often (though not always) given equal voting rights, freedom, and pirate prizes, which slaves in Athens never enjoyed. Constitutional checks and balances were used to prevent captains from becoming tyrants: while the elected captain decided where to sail and who to attack, pirates elected a “quartermaster” to check the captain’s power. The quartermaster resolved disputes between sailors (and captains) and took care of distributing food, drink, and plunder.
The quartermaster jealously guarded the “egalitarian ethos” baked into pirate constitutions. In one case, a quartermaster dismissed a captain for wearing a fancy (looted) suit to dinner— without asking permission first.
The Pirate Captains having taken these Cloaths without leave from the Quartermaster, it gave great Offence to all the Crew; who alledg’d, ‘If they suffered such things, the Captains would for the future assume a Power, to take whatever they liked for themselves.’
In another case, a crew cycled through thirteen pirate captains during a single voyage. Sometimes, these captains were merely demoted. Other times, they were punished, killed, or “put on shore on some uninhabited Cape or Island, with a Gun, some Shot, a Bottle of Powder, and a Bottle of Water, to subsist or starve.” Having helplessly endured the abuse of captains in their prior lives as naval and merchant seamen, pirates were extremely sensitive to the sense of entitlement that accrues to people in positions of power. By limiting the special privileges of captains (no private bedrooms, no private dining quarters, and a mere “double share” of the booty afforded to common pirates) and by enforcing this sense of fairness with the hawk-eyed vigilance of a petty child, pirates created a culture where captains were prevented from overstepping their mandate.
For sailors on merchant ships, the lure of pirate life (and its strictly-enforced egalitarianism) reduced the incentive to fight back. When confronted by pirates, sailors were known to cheer and to actually fight for the opportunity to join their maritime marauders. In at least one recorded instance, “more [fed-up sailors] would have enter’d than [the pirates] would accept of.” Of course, there were plenty of righteous sailors who fought pirates to the death (despite pirates’ reputation for torturing resistors) while there were other skilled sailors (like surgeons and carpenters) who were conscripted by pirates against their will. But for the most part, attitudes toward pirates on the high seas were remarkably positive.
Pirates’ egalitarian structure not only gave them a philosophical edge against other ships — it gave them a strategic edge, too. By aligning the crew’s incentives (offering bigger shares of equity, more freedom, and insurance if injured) pirates fought with extra vigour and usually defeated their merchant rivals. Still, plenty of pirates were caught during the Golden Age of Piracy — but only a few pirate ships were taken. Even fewer were caught with treasure on board. (Dead to rights, some pirates preferred suicide. In one account, pirates began shooting a giant pile of gunpowder on board, “swearing very profanely lets all go to Hell together.”)
Despite the rampant drinking, radical democracy, and rotating captains, pirate organizations performed as well as other seaborne organizations. They may even have performed better: during the War of Spanish Succession from 1701–1714, Spain and France hired privateers to (legally) plunder British vessels. In the ten years after the war — after French and Spanish privateers were put out of business — the pirates who replaced them plundered even more British boats than the privateers had. The pirates were so effective, they brought the world to the brink of a trade crisis.
“Could a few thousand ragged outlaws be more powerful than the combined naval and privateering forces of two of the world’s greatest nations?” asks our pirate historian Rediker. The incomplete military and financial records will never give us a definitive answer to his question. From the anecdotes we have, though, pirates not only plundered ships more effectively than government-backed vessels — they were so successful they posed an existential threat to early global capitalism.
Predictably, pirates’ free-wheeling ways didn’t last forever. While pirate ships were able to outcompete individual rivals, they were no match for entire navies, and especially not the consolidated front of a multinational anti-piracy campaign. Piracy flourished during an era where nation states were too busy fighting one another to worry about pirates; after the 1713 Treaty of Utrecht (which established peace between Spain, Great Britain, France, Portugal, and the Dutch Republic) navies slowly began committing more ships to protecting trade routes, and working together to rout the scourge of pirates. Navies also grew stronger (from 1718 to 1815, the British Royal Navy nearly doubled its fleet from 124 to 214 ships), while lawless pirate hideouts like the Bahamas were brought under tighter colonial control. By the end of the 1720s, most pirates had been caught, hung, or scared into hiding. The Golden Age of Piracy had come to an end.
So what of it? Pirate culture was more or less extinguished. The dress, speech, and lifestyle of Golden Era pirates disappeared. Sailors no longer feared (or looked forward to) pirate encounters, and investors could sleep soundly — knowing their precious cargo had little chance of being nicked by rum-breathed brigands. This is probably for the best: pirates were ruthless murderers, treacherous thieves, and parasites on society.
Yet despite their naughty nautical ways, it’s worth giving credit where credit is due. In an era that was excessively nationalistic, pirates embraced diversity: most pirate crews had members from all over the world, and (according to some estimates) more than 30% of crew members were non-white. Tolerance for unorthodox lifestyles was the norm, egalitarianism bolstered the esprit de corps, and workers were given agency over their day-to-day lives. Some pirate innovations (like constitutional democracy) predate their appearance in nation states by more than a hundred years. The French Republic’s best-known political painting (Delacroix’s Liberty Leading the People) is itself based on an illustration of female pirates. There’s no wonder, then, that pirate culture continues to inspire some of today’s most successful organizations.
However, the organizations that are most influenced by pirate culture are not nation states… but technology companies. The word “pirate” has long been invoked (in both good-natured and not-so-good-natured contexts) to describe their behaviour. The egalitarian structure of these companies — which typically includes employee stock grants, health insurance, and greater workplace liberty — is, if not deliberately modelled off of pirate organizations, the result of similar workplace incentives. Both pirate ships and startups have low start-up costs, they both compete against traditional merchants, they both offer high-risk/high-reward tradeoffs to employees, they both compensate for these risks by offering employees greater freedom in the workplace, and they both are relatively small (the average pirate crew size was ~80.)
Just like pirates took advantage of limited government oversight on the seas, startups can take advantage of limited government oversight in other areas (like, say, cryptocurrency.) By operating within these sort of high-risk areas — and despite going up against organizations with access to more resources — startups can eke out an advantage by pulling from the pirate’s arsenal of tricks: A fun, empowering workplace to out-recruit your rivals. Equitable compensation to make employees work harder. Tolerant hiring practices, so the strongest candidates aren’t passed over. The swapping out of impersonal bureaucracy for worker-led decision-making.
Oh yeah... and all the free beer you can handle.
Because when you let your pirate flag fly, there’s no stopping where your team can go.
I mean, just ask Steve.
— Steve Jobs
