Be More Pirate: The Disruptor Series Live Podcast

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Why a Pirate’s Life is for You

The pirate community paved the way for some of today’s most influential leaders, or at least that’s how it’s seen by Sam Allende, serial entrepreneur and author of Be More Pirate: Or How to Take on the World and Win. Allende sat down with TBWA/Chiat/Day NY CEO Rob Schwartz to talk about the new book during The Disruptor Series Live Podcast.

The book aims to bring out the inner pirate in all of us by drawing parallels between some of today’s most influential leaders and some of history’s most famous pirates. Allende relates the likes of Steve Jobs, Jay Z and Sheryl Sandberg to those of Blackbeard, Black Caesar, and Anne Bonny by examining some of the strategies they used to make their mark.

Schwartz and Allende ran through the book’s “Five Rrrrr’s” that make up the blueprint pirates and today’s leaders used as the foundation of their success. To elaborate on the ideas, Allende looked at the story of Grammy award-winning artist and philanthropist Chance the Rapper.

Rebel. Allende believes that there are people who act on their inner pirate, people who try to, and people who wish they did. At the beginning of every pirate success story is a rebel, or someone who recognizes that the way people are doing things isn’t necessarily the strategically and/or morally right way to do them, according to Allende.

Chance the Rapper recognized that the music industry was set up in such a way that record companies were taking advantage of young artists, and he went on to become the first ever independent artist to win a Grammy. He didn’t just break the rules, he completely rewrote them.

Rewrite. Chance’s actions, and those of other successful pirates, have a lasting impact on their entire community. By showing young artists that success was possible without a major label behind them, he created hope for thousands of young artists that didn’t think they had a chance. Allende considers these leaders to be setting a new precedence by rewriting the rules- something he considers vital to progress as a country.

“There’s an urgency in the air and a need for change. Today, if we want to improve the picture of our future, we need a little less Instagram and a little more action,” an excerpt from Allende’s book reads.

Retell. Once the new precedence is established, pirates essentially have an empty book to tell their story in. What opportunities does this new way of doing things create? For traditional pirates, it created the opportunity for someone to live and earn their living without all of the rules and regulations of a normal job. As Steve Jobs put it, “it’s more fun to be a pirate than to join the Navy.”

In Chance the Rapper’s story, we see an emerging artist empowered to promote political issues that a major record label might force them to censor out of their music, according to Allende.

Reorganize. A pirate ship’s leadership structure is something Allende thinks we may be able to learn something from. He explained the dual leadership structure in which the captain handles more of the strategic duties while the quartermaster deals with issues concerning culture and implementation of strategy. While this is less applicable to the example of Chance the Rapper, it’s applicable to entrepreneurs in search of a different way to structure their business.

Redistribute. In the end, a true pirate, both historically and today, has the opportunity to redistribute wealth and power in his community, according to Allende, who says that the democracy seen on a pirate ship was one of the largest democratic systems seen up to that point in history. Even overtaken ships were given the opportunity to join a community with fair wages, according to Allende, and crew members were interviewed to determine if the leadership of the defeated captain would fit within the new community.

Looking once more at Chance the Rapper, we see someone who was able to use his new power to pour millions of dollars back into public school systems, redistributing the wealth traditionally reserved for record label executives.

A theme carried throughout the event related to the idea that establishing a strong network within a community is a better indicator of success in early stages than looking at scale. Allende believes that the best way to achieve that goal of a tightly knit network is through finding values so powerful that you can make decisions based off of them.

Allende’s advice for all of the aspiring pirates of the world right now?

“Break a rule today…then do it again tomorrow.”

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