The buccaneers of the 17th and 18th centuries had surprisingly modern sensibilities.

“I’d rather be a pirate than join the Navy,” said Mr Steve Jobs. If you echo that sentiment with a hearty “yarrr”, then you might enjoy reading Be More Pirate: Or How To Take On The World And Win by Mr Sam Conniff Allende, a social entrepreneur and co-founder of youth-led creative network Livity. In the book, Mr Allende, who has delivered piratical workshops to executives at Google and Facebook, draws parallels between the modus operandi of 18th-century buccaneers and 21st-century rule breakers, such as Mr Elon Musk, Chance The Rapper and Banksy.

Business lessons aside, one of the most thought-provoking takeaways from the book is that our negative, cartoonish image of pirates – by which we mean “golden age” pirates who prowled the Caribbean, the eastern seaboard of North America, the west African coast and Indian Ocean between 1690 and 1725 – was largely drawn by a crooked establishment (European powers were looting, pillaging and murdering under the banner of empire expansion) with a vested interest in destroying and discrediting them. They weren’t exactly saints, but pirates could be seen as early disruptors, with forward-thinking ideas that threatened the status quo. Their revolutionary notion of sharing power and money was a challenge to the authorities. They believed in democracy. Every crew member on board a pirate ship had a vote, while the Republic Of Pirates in Nassau in the Bahamas was one of the most egalitarian societies anywhere, until it was crushed by the British in 1718.

Pirates were self-interested, not progressive. Nevertheless, running a tight ship – and evading the authorities – led to a number of innovations, as these five examples taken from the book demonstrate.

Spending months at sea in confined quarters where women were, with a couple of notable exceptions, not permitted, some crew members inevitably grew close. In the Navy, such fraternisation was severely punished. (Sir Winston Churchill allegedly decried Britain’s naval tradition as “nothing but rum, sodomy and the lash”.) Pirates, however, acknowledged such relationships under the term “matelotage”, in some instances celebrating them with ceremonies and creating legal frameworks for the couple to share rights of ownership and inheritance.

From 1664 to the early 19th century, the Navy press-ganged recruits into joining against their will, abused them horribly and paid them a pittance, if they were paid at all. So, it’s no wonder so many went “on the account”, that is, turned pirate. All crew received an equal share of looted goods and money, with the exception of high-value or high-risk roles, such as doctors and gunners, who took twice as much, and the captain and quartermaster, who took three or four times as much.

Some pirates treated women terribly, but others prided themselves on gentlemanly conduct. Article Vi of Mr Bartholomew “Black Barty” Roberts’ code from 1722 (pirate ships had codes of conduct) expressly forbade crew members from seducing women and carrying them to sea disguised. Then there were pioneering female pirates such as Ms Anne Bonny who, abandoned by her husband, defied the laws of the time that said she was his property to sail away with the dashing Captain Jack Rackham. Or Ms Mary Read, who’d previously disguised herself as man to join the Army and the Navy, both off limits to women. When her pirate lover was challenged to a duel over gambling debts, rather than leave things to chance she pulled out a sword and killed his opponent herself.

We often imagine pirates with eye patches, hooks for hands and peg legs – buccaneering was dangerous business. Injured crew members were recompensed, ranging from 800 pieces of eight for a lost leg and 600 for an arm down to 100 for a finger or an eye, which doesn’t seem commensurate, but hey. This compensation scheme predates employer liability laws passed in America in the 1850s and the UK in 1880, never mind the UN’s Declaration of Human Rights in 1948, which enshrined the universal right to social security.

Pirates did participate in slavery; they were sometimes paid in slaves instead of money. But their attitude to the repellent practice evolved more quickly than the rest of the “civilised” world. Historian Mr Kenneth Kinkor declares, “The deck of a pirate ship was the most empowering place for blacks within the 18th-century white man’s world.” Freed slaves were paid to join pirate crews, which were on average a third non-white. In 1718, the year he was killed, Blackbeard’s crew was 60 per cent black. Aye, aye, chief diversity officer.

Be More Pirate: Or How To Take On The World And Win by Mr Sam Conniff Allende (Portfolio Penguin) is out today