4 Int-ARR-esting Reasons Entrepreneurs Relate to Pirates

by . September 17th, 2014

Talk Like a Pirate Day isn’t nearly as popular as it used to be, perhaps because it’s been a few years since Hollywood’s come out with another Pirates of the Caribbean sequel.

But while pirates are no longer at the forefront of pop culture, this fun observance is a great time to reflect on what made pirates and their close cousins, privateers very similar to you, the entrepreneur.

Capture-of-Blackbeard Jean Leon Gerome Ferris (1863–1930)
Capture of Blackbeard, by Jean Leon Gerome Ferris (1863–1930)

Now I’m not expert on pirates, just a mere pirate enthusiast who happens to run an entrepreneurial resource blog. Puns aside, pirates are the quintessential amoral entrepreneur.  Here’s why so many entreps relate to them.

4.) Pirates are risk takers

Although they’ve been active nearly everywhere all over the world, pirates typically pop up in places where being a “legit” entrepreneur could be difficult. Present-day Somalia and the 17th century Caribbean are not even remotely examples of fertile breeding grounds for legal forms of entrepreneurship.

For one thing, the rule of law would have to exist before anything legal happens. Secondly, these areas were close to major shipping lines,  providing abundant opportunities in the form of ships weighed down with healthy amounts of booty.

There are of course, inherent risks with trying to take these ships, and chances are generally slim you’d die from natural causes. Blackbeard for example, was active for only 3 years – which was actually a pretty long time for in pirate terms. Being a pirate is dangerous, and few people. have the aptitude or stomach for it.  Interestingly enough, piracy is rarely ever  a “necessary” career path.

So why do it? Like any other entrepreneur, pirates are willing to put some very important things on the line for a perceived reward. Unlike most entreps though, pirates stake their very lives.

3.) They’re adaptable

The Secret of Monkey Island – LucasArts

Pirates have nearly without exception, proven themselves to be extremely flexible. They have to be, otherwise the authorities wise up and they get caught. Or worse. Their ingenious exploits are one of the very things that have allowed pirates to capture our imaginations.

They’ve even been known to anticipate changes in their “market” so to speak, and adapt accordingly. A few years ago, Somali Pirates even opened a betting pool for landlubbers to help finance their operations.

Modern pirates use a great deal of technology. Recent crimes of piracy have involved the use of mobile phones, satellite phones, GPS, Sonar systems, modern speedboats, assault rifles, shotguns, pistols, mounted machine guns, and even RPGs and grenade launchers. Pirates have also been known to use social media. Of course, why wouldn’t they?

2.) Pirates tend to value individual merit over tradition


Merit isn’t the first thing you think about when we think of pirates. Or democracies, for that matter.  In any case, pirates were also among the first widespread practitioners of democracy – and for a very good reason.

The pirate crews of the so-called “Golden Age of Piracy” in the 17th century almost overwhelmingly functioned as limited democracies, where as a general rule, every crew member had a vote in important matters.

Pirates of this era usually elected their ship’s captain (who decided where they went and how they fought) and their quartermaster (who could override the captain and divvied the loot), who in turn appointed other pirates for different positions. Contrast this with the tyrannical leadership typical of most naval and merchant vessels of the era.

As a pirate ship was an extremely dangerous place to be, and since everyone was on the same ship, great care was usually taken to ensure they chose the leaders who could get most of them back to post safely – and profitably. Even today, most pirate crews are at least partly democratic, with command structures likely to mirror a business cooperative.

Apart from their democratic practices, pirates also practiced egalitarianism in other ways, with crews coming from literally all races, social classes, and genders. Of course, there were plenty of pirates who participated in the slave and prostitution trades.

Regardless, pirates have been among the first noted groups to have racially-integrated crews, where pirates of all colors were treated as co-equals and everyone had a somewhat fair chance at advancement. Women have also managed to become leaders among pirates in eras where women wouldn’t normally be business owners. Pirates  from the Golden Era of Piracy also practiced a form of civil union that is functionally indistinguishable from most modern same-sex marriages.

1.) Their way of life was often its own reward

Howard Pyle - Pyle, Howard; Johnson, Merle De Vore (ed) (1921) Buccaneers and Marooners of the Spanish Main
Pyle, Howard; Johnson, Merle De Vore (ed) (1921) Buccaneers and Marooners of the Spanish Main

Ask any serial entrepreneur if they ever want to do or be anything else. We’ll give you 9-to-1 odds they’ll say “no”.  Like most entreps, many if not most pirates past and present chose their lives. Even when presented with opportunities to come back from the cold, most would consider their way of life better than the alternatives. For many, the freedom that comes from being an entrepreneur is well worth the uncertainty of their futures.

Perhaps that’s why we find them so fascinating.

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Arthur Piccio manages YouTheEntrepreneur and has managed content for major players in the online printing industry. He was previously BizSugar's contributor of the week. His work has appeared multiple times on The New York Times' You're the Boss Small Business Blog. He enjoys guitar maintenance and reading up on history and psychology in his spare time.