Sam Conniff knows a thing or two about rule-breaking. When his book, Be More Pirate: Or How to Take on The World and Win, launched, he wanted to post a billboard-sized neon pink announcement on the Penguin Random House UK building in London. Unfortunately, the powers that be at the publisher said no.

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Fortunately, Sam's credo is that, sometimes, "no" really means "go," and in his estimation this was one of those times. Sam recruited some co-conspirators to dress up as contractors so that the rogue installation looked official. He didn't even use his own money to pull off the stunt; instead, he earmarked the fee his publisher had agreed to pay him for a future event.

He got the poster up on the building, posed for a quick photo, then moved swiftly away from the scene and waited for the tweets (and the book sales) to start. After a slow morning, Richard Branson learned of the stunt and tweeted, leading to a cascade of social mentions, incoming messages, news coverage... and book sales! 

I invited Sam to Marketing Smarts to talk about the revolutionary approach of Golden Age pirates, and how the same approach applies in the 21st Century. In Be More Pirate, Sam compares the innovation of pirates with that of modern-day rebels like Elon Musk, and explains how professional rule-breaking is the only way to effect change in today's world.

Here are just a few highlights from my conversation with Sam.

Golden Age pirates had more in common with modern entrepreneurs than with popular characters like "Captain Jack Sparrow" (04:36): "The real history of pirates was written out of the history books by the king of England at the time, and backed up by the ruling powers. So what's been lost to history (which needs to be airbrushed back in) is their role as working-class heroes and social innovators....

"This generation was doing exactly that. Their ships, their business model, was truly entrepreneurial. And they, as many entrepreneurs do now, married that business model—the desire to create their own path, their own fortune—with a fight for freedom. I know that sounds like a long stretch from the pirate stories we know, but it certainly seems to be the truth."

If you think your idea's too radical to work, consider that pirates risked life and limb to implement radical changes like workers compensation and equal pay (07:33): "What would the new rules be if we could free ourselves from just complaining about the chaos we see unfolding in front of us?

"If you take some of the examples [of this pirates implemented like] workers' compensation, equality of pay, these weren't just big ideas, they were seditious ideas. And so often, in our industry, when our opportunity is so huge, our experience is so great, our resources enormous, we still don't find solutions that are equal to the size and scale of the challenges outside the window.

"By comparison, they're nowhere near meeting the scale. And [pirates] were rewriting organizations with rules that they would be hung for, and they were willing to risk everything for. And they still did so in the fight for a better, fairer, more equal set of structures. How can we not find that inspiring that right now?"

Pirates were amazing marketers who created powerful brands (11:06): "What they created was a brand. The skull and crossbones is, without doubt, other than possibly the cross of the Christian religion, the first deliberately designed brand that was intended to have a singular message, as all the good marketers out there know. And the single message was 'surrender or die.'

"And with this meme designed to go viral with this clear message, ships coming over the horizon would see the skull and crossbones unfurl and they had a choice: 'Do we capitulate now and hand everything over, or get into a fight that we can't win?' And so it drove [the pirates'] bottom line.

"They were out to take the loot that the empire builders that they stood against, they were out redistribute to the ordinary, and when the loot came onto their ships they distributed it freely and evenly. This terrifying brand meant that they were able to avoid a fight."

Pirates, like marketers, commandeered the most popular communication channel and used it to spread their brand message (12:39): "For the modern marketers, what pirates were doing was taking the number one communication system at the time, which was the royal naval flag system. The royal naval flag system was the only international, cross-border, cross-language communication system. And there were some very clearly defined rules about what you can and can't do.

"You certainly can't fly a black flag with a skull on it. That had a whole new meaning, so [the pirates] did. And individual captains would tweak this...but they were all playing on messages of death and 'we're coming for you,' so they had singular messaging. So when we reach the prime of the golden age, there's a sense of unity amongst the pirate community."

"Be more pirate" really means to engage in thoughtful rule-breaking to bring about change (15:45) "Pirates weren't just rejecting society as agents of chaos. They were rewriting the rules of society and that's why it's so important. The principle of being a pirate is: What rules do we need to class now as out of date, and what rules would we put in their place? And if we were to redistribute power from its very limited points of leverage and take some ownership over our destiny ourselves, what would be the rules that we put in place?"

When change is truly necessary, forget about asking permission and just seek forgiveness (17:07) "Who doesn't work in an organization that 'celebrates creativity,' but that actually really just reward conformity? The unspoken truth of it all, and it's in those difficult spaces, where we know the culture is the number one driver in that area, what's our opportunity to rewrite the rules? Not to ask permission, not to have to put a deck together, not to be sent away to work on a strategy paper for our good ideas that we all know will go nowhere or be sent to the eternal damning hell of a thread of emails, where all good ideas get sent to die.

"What would happen if you and the smart people you know who have thought through a really good idea don't go and seek permission, but prepare yourselves to ask forgiveness if need be and you begin your new protocol? Your new principle? Your new way of doing things today?

"We're so hard wired against this, yet history always tells us that's where change happens."

To learn more, visit You can also follow Sam on Twitter at @samconniff, and be sure to get your copy of Be More Pirate: Or How to Take on The World and Win.

Sam and I talked about much more, so be sure to listen to the entire show, which you can do above, or download the mp3 and listen at your convenience. Of course, you can also subscribe to the Marketing Smarts podcast in iTunes or via RSS and never miss an episode!

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