The swashbuckling author teaching entrepreneurs how to be buccaneers

Before Disney’s Pirates of the Caribbean franchise, maritime swashbucklers were about more than eyeliner and Orlando Bloom. In fact, it’s possible Robert Louis Stevenson was closer to the mark in presenting pirates as heroic outlaws, whose thievery and sword-fighting merit glorification over farcical misrepresentation.

This is the view of entrepreneurturned-writer, Sam Conniff Allende. The Livity founder has a theory he promotes with vigour: could pirates be placed on the same spectrum as the great social revolutionaries, from Suffragettes to Civil Rights activists?

It sounds far-fetched, but when the Be More Pirate author jumped on his desk to deliver his opening remarks at a recent Leap 100 event, one couldn’t help but sit up and take note.

“Three centuries ago, the world was surprisingly similar. The establishment was broken, there was a backdrop of international interconnected conflict, and millennials of the day worried the rise of technology would crush employment as they knew it.” So they left town and created new societies aboard ships – societies that pilfered and raped, yes, but that also included the systems we operate and abide by today.

Conniff Allende upends traditional notions around the origins of company structure, employee rights, and social justice. Pension schemes, workplace compensation, even same-sex marriage took root on the pirate ship, he says.

“Pirates realised that power corrupts, so everyone had a vote and equal say.” Forget Coca-Cola: the Jolly Roger was the first “brand” to go viral, and pirates were “the unicorns of their time”.

Like the bandits he intently studied, Conniff Allende himself has never feared breaking the rules in the name of change. As a teenager, he began running club nights in the hope it “could make the world a better place”. Aspirations were dashed when, at 22, he found himself £200,000 in debt. Butrather than join the traditional workplace, he founded Livity, an independent youth marketing agency.

Conniff Allende is decidedly positive about Livity’s accomplishments and the “incredible young change makers” it works with. Yet he is also candid. “Success is always a mess. Creating change is hard, stressful and difficult.”

Two decades later and having stepped down as chief executive (though he remains on the board), he collated the advice he’d  passed on to young founders and, in his “scariest” career move to date, wrote a book.

The past year has been a whirlwind of testing ideas across multiple continents and industries, searching for people who fit the pirate mould. His objective is clear: to convince entrepreneurs to reimagine pirates as champions of change. In doing so, founders can perhaps be galvanised into following the footsteps of Blackbeard and Elon Musk in applying a “dynamic framework for surviving certain uncertainty”.

Be More Pirate has already become an overnight hit and made it to the top of Amazon’s business, leadership and creativity book lists. Rights went to bids in the US, and are in negotiation in various territories including Russia. But the personal stories inspire Conniff Allende as much as any commercial success.

“I’ve been contacted by people who want to bring about change and defy the conventions that hold them back. A woman I mentored years ago just emailed to say she had resigned.”

Perhaps the entrepreneur and author will one day be viewed as a professional revolutionary, like the buccaneers he so admires. After all, Steve Jobs famously claimed: “it’s better to be a pirate than join the navy”.