Arghh me hearties: A pirate's life for CEOs means more than pieces of eight

Sam Conniff Allende
Batten down the catches, ye skirvy dog (Source: Getty)

The upside to an age of uncertainty is that it is fertile ground for opportunity.

But fortune favours the brave, and the future will belong to leaders who show imagination, ambition, principles, and the right degree of risk-taking.

Where are those leaders? Sadly, we can’t look to our own front benches for them, and we can’t continue to hold up Silicon Valley as the default standard for good innovation either. So where do we look for inspiration in disruptive times such as these?

Well, I have an answer that might sound unlikely at first. We need to look back to the eighteenth century, and to the pirates that ruled the day. Pirates? Yes, pirates. Pirates who were more role-models than rogues, whose strategy, success, and radical innovations have been covered up by history, but who hold answers to many of the questions we currently face.

I’d like to introduce you to the lesser-known truth of the Golden Age of Pirates, as the role models you need to help you survive and thrive in the disruptive twenty-first century.

Read more: How to get Facebook and Google to talk like pirates

You see, 300 years ago, a small group of frustrated and underappreciated professionals had enough of being led badly by a self-interested establishment. Disruption had become their constant backdrop as they faced ongoing uncertainty and mass redundancy in a world plagued by ideological conflicts.

Sound familiar?

So these pirates set out not to break the rules, but to remake them, and as much as they flew a flag for finding their fortune, they also flew a flag for innovation, equality, and diversity – and it’s here that their lessons lie for the leaders of today.

You could draw a comparison between Black Sam Bellamy, the Prince of Pirates, and Mark Zuckerberg, who both at 28 were among the youngest, most successful (and richest) men of their hour. Only Black Sam knew the importance of transparency and accountability, and devolved his authority to his followers, who held the power to remove him if his ethics or bravery wavered.

You could point to a similarity between Anne Bonny, the Pirate Queen, and Sheryl Sandberg, who both in their own way encouraged women around the world to Lean In by demonstrating fearless leadership. Only, aboard Anne Bonny’s crew equality was a reality, and transparent pay and decision-making structures were in place at every level of the organisation.

You could argue that Henry Avery, the Pirate King, shares many attributes with Elon Musk, both famous for their headline-grabbing exploits. But whereas Musk’s vision for a new society on Mars costs $200,000 a ticket, the pirate republic that Avery helped architect became a beacon of democracy and opportunity for all.

The Golden Age pirates were true innovators, from pioneering workplace compensation (first seen on a pirate ship) to developing workplace culture (and I mean more than just free rum).

Pirates represent a responsive approach to professional rule-breaking, and this is where their most profound lesson for us lies. If the only certainty we face is uncertainty, now is not the time for binary thinking.

Read more: How low oil prices are changing pirates' tactics

We need leadership that can span paradoxes. We need leaders that recognise when it’s the right time not just to break the rules, but to create new ones.

The most unlikely of all the lessons that we might learn from pirates is perhaps the one we need most. What held the community of pirates together, and enabled them to outsmart the establishment in what we’d now call agile networked systems, was a very simple principle indeed. One of trust.

Unlikely as it sounds, deeply woven and enforced trust (not pieces of eight) was the real currency that enabled the pirates’ dynamic model to take on the world, and to win.

City A.M.'s opinion pages are a place for thought-provoking views and debate. These views are not necessarily shared by City A.M.

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