Be More Pirate

What if the key to innovation, justice, and meaningful work lies not in following rules but in rewriting them? In Be More Pirate, Sam Conniff Allende argues that to survive and thrive in an age of uncertainty, bureaucracy, and inequity, you must think like a pirate—specifically, the Golden Age pirates of the late seventeenth and early eighteenth centuries. They weren’t the lawless outlaws we imagine. They were bold innovators who rebelled against oppressive systems, created democratic communities, and turned mutinies into movements. Conniff contends that their mentality—rebellious yet constructive, self-determined yet collective—provides the perfect blueprint for modern leadership, innovation, and activism.

Like a rallying cry, the book asks: what if you stopped waiting for permission? What if you led change instead of waiting for someone else to? By learning from history’s most misunderstood rebels, you can shake up broken systems and design new ones grounded in fairness, creativity, and collaboration. Conniff shows that pirates ‘didn’t just break rules, they rewrote them’—and that you can do the same in your professional, social, and personal life.

From Villains to Visionaries

Conniff reclaims the pirates’ true legacy, peeling away centuries of propaganda. The Golden Age pirates—like Henry Morgan, Anne Bonny, Mary Read, and Blackbeard—emerged during the chaos of empire, austerity, and mass unemployment. Many were veterans of naval service, abused and unpaid, who staged a collective rebellion against injustice. In Nassau, they built the Republic of Pirates, a radically equal society that predated Western democracies by decades. They invented a code of conduct before the term ‘human rights’ existed: fair pay (“no prey, no pay”), equal voice (“one pirate, one vote”), injury compensation, and even tolerance toward different races, genders, and sexualities.

By freeing themselves from top-down hierarchies, they revealed the power of small groups—what Conniff calls “the paradox of scale”: staying small, nimble, and connected gives you more power than bloated, rigid organizations. This pirate ethos, he argues, is a remedy for modern institutions weighed down by bureaucracy, inequality, and blind obedience.

Five Pirate Tactics for Modern Rebels

Conniff distills the pirates’ wisdom into five practical tactics for today’s changemakers:

• Rebel: Resist systems that don’t serve fairness or progress. Like Captain Sam Bellamy, challenge unjust leaders and institutions with courage and vision.
• Rewrite: Don’t just break old rules—replace them with better ones. Anne Bonny and Mary Read didn’t just defy gender norms; they redefined them.
• Reorganize: Build agile, collaborative networks that scale through connection rather than growth, similar to pirate fleets that joined and dispersed as needed.
• Redistribute: Share power fairly. Pirates practiced transparent pay and elected leaders—a radical model for modern organizations.
• Retell: Craft your own legend. Pirates weaponized storytelling to spread their reputation and rally followers; modern movements do the same through social media and branding.

Together, these practices become what Conniff calls a “Pirate Code”—a set of values and commitments you can use to lead rebellions for good in business, activism, or personal growth. It’s democracy without bureaucracy and leadership without ego.

Why It Matters Now

Conniff wrote Be More Pirate because our modern world mirrors the pirates’ era. Then as now, people face systemic inequalities, technological upheavals, and leaders out for themselves. From Silicon Valley’s greed to political cynicism and the crushing conformity of corporate life, too many of us feel disempowered. The author argues that small, rebellious acts of “good trouble”—a phrase borrowed from civil rights activist John Lewis—are how we reclaim power and purpose.

To be “more pirate” is to combine rebellion with responsibility: breaking rules not for chaos, but for creative renewal. Whether you’re a disillusioned employee, a burned-out activist, or a dreamer with a side hustle, you can become a modern mutineer by rewriting the broken rules shaping your world. At its heart, Conniff’s manifesto is a call to arms: become your own captain, build your crew, and start a new code. The world isn’t changed by obedient followers—it’s changed by imaginative rebels with a cause.

Conniff begins the pirates’ five-part framework with rebellion—the spark that sets every mutiny in motion. To be a rebel doesn’t mean being destructive or contrary for its own sake. It means finding the courage to stand up against the unfair, illogical, or harmful rules that define your world and daring to say, “No more.”

The Power of Good Trouble

The author borrows civil rights leader John Lewis’s idea of “good trouble”: purposeful disobedience that challenges injustice. For the Golden Age pirates, rebellion meant rejecting brutal naval hierarchies and inhumane treatment. For us, it might mean calling out toxic leadership, demanding fairer pay, or disrupting outdated industries. The goal isn’t chaos—it’s constructive resistance.

Captain “Black” Sam Bellamy, the real-life Robin Hood of the sea, embodied the rebel spirit. In an incendiary speech recorded in 1724, he condemned the hypocrisy of governments that labeled pirates “villains” while stealing and killing under the banner of empire. His words—mocking the “sneaking puppies” who obey “laws which rich men have made for their own security”—still echo as a timeless call for equality and courage.

From Radio Waves to the Cloud

Conniff connects this spirit to modern examples of rebellion. When governments or corporations abuse their power, creative rebels find loopholes. In the 1960s, pirate radio ships like Radio Caroline broadcast rock music from international waters, bypassing the BBC’s control and reshaping global pop culture. A few decades later, digital pirates—from Napster’s music sharers to The Pirate Bay’s streamers—forced industries to rethink access, pricing, and ownership, paving the way for Spotify and Netflix.

In both eras, small acts of mutiny by small groups created industry-wide revolutions. Rebellion, Conniff shows, is the necessary prelude to renewal. The establishment resists change until outsiders force its hand.

Modern-Day Rebels

Conniff profiles twenty-first-century rebels whose acts of “good trouble” changed the world. Malala Yousafzai began by writing a simple blog about girls’ education in Pakistan and ended up challenging the Taliban’s oppression, surviving an assassination attempt, and winning the Nobel Peace Prize. Like the pirates, her first step was small but intentional—writing publicly about what others feared to say.

Rebellion doesn’t have to start with fire or fury. It begins with discomfort, a sense that silence equals complicity, and the courage to act. Conniff reminds you that being a rebel today might mean questioning your own workplace hierarchies, calling out unethical habits, or innovating in broken systems. Every act of rebellion, no matter how small, is a rehearsal for changing the world.

Once you’ve rebelled, then what? Conniff says the second pirate step is to rewrite the rules. Revolution without reconstruction just leaves a vacuum. Pirates didn’t just burn down the old order—they built a better one on deck. Their mutinies became movements because they codified their new principles into shared agreements: the Pirate Code.

From Destruction to Creation

Golden Age captains like Anne Bonny and Mary Read broke nearly every rule written for women. Hiding their gender, fighting alongside men, and commanding ships, they became living arguments for equality. Their rebellion didn’t end with defiance—it redefined what women could be. Conniff calls this the essence of rewriting: replace stupidity with sense, replace hierarchy with humanity.

In the modern world, the same spirit exists in innovators who don’t just complain about broken systems—they build better ones. Elon Musk’s companies—Tesla, SpaceX, and SolarCity—represent industrial rule rewriting on a planetary scale. Like a modern-day pirate king, Musk questions every assumption, from car design to space travel, using “first principles” reasoning: ask what’s truly necessary, then rebuild from scratch. (Note: Conniff explicitly compares Musk’s methods to the pirates’ refusal to obey top-down logic.)

Rewriting as Reinvention

Creative industries illustrate the pirate pattern beautifully. Hip-hop, born from marginalized voices, reinvented music through sampling—rewriting old sounds to create new meaning. RZA and the Wu-Tang Clan flipped the traditional record label system by signing a group deal that allowed each member to pursue solo contracts, redistributing power and wealth. Later, Chance the Rapper upended music economics again by releasing his albums for free and funding his career through performances and merchandise.

Closer to home, anyone can engage in small-scale rewriting: rethinking how we measure success, run meetings, or share credit. As Conniff notes, systems don’t change by accident—they change because someone dared to redesign them.

Everyday Mutinies

The book highlights simple but powerful examples of modern mutinies. In 2017, millions joined the Women’s March after one woman—Teresa Shook—posted a frustrated Facebook comment. In 2011, Britons responded to urban riots not with fear but with collective action, using the hashtag #riotcleanup to mobilize broom-wielding volunteers. Rewriting starts with individuals who refuse to accept decay as normal.

Conniff’s message is clear: rebellion without re-creation is just noise. The moment you install new values in place of old ones, you’re no longer just a rebel. You’re a rule-maker. You’re becoming more pirate.

Pirates didn’t grow large—they grew smart. In their third principle, Conniff shows how they achieved scale through collaboration rather than size. Their lesson is crucial in an era when companies equate growth with success but often lose agility and soul in the process.

The Paradox of Scale

At their peak, perhaps 1,500 pirates took on the Royal Navy’s 45,000. Yet they thrived because they operated as agile networks: small, autonomous crews who could merge into massive fleets like Henry Morgan’s 2,000-man assault on Panama, then disband into lean strike teams. Their secret was scale without growth—speed, flexibility, and equality.

Compare that to modern corporations obsessed with exponential expansion. Conniff cites author Frederic Laloux (Reinventing Organizations), who warns that unchecked growth “for growth’s sake” is economic cancer. The pirates’ model—fierce independence combined with accountable collaboration—foreshadowed structures like today’s holacracy, agile teams, and flat organizations.

Fairness and Diversity Afloat

Contrary to myth, pirate ships were some of the most democratic and diverse workplaces in history. Crews voted on leadership and pay, combining structure with freedom. They practiced rotating authority: captains commanded during battle but ceded power afterward. Nonwhite sailors—up to one-third of many crews—held leadership roles, while women like Anne Bonny and Mary Read earned respect as equals. Pirates even recognized same-sex partnerships (“matelotage”), offering shared inheritance rights centuries before modern laws.

This inclusivity wasn’t moral idealism; it was strategic. Diverse teams perform best. (Modern research by McKinsey confirms companies with diverse leadership outperform their peers by up to 35 percent.) Three centuries ago, pirates proved the point firsthand.

Networks of Modern Mutineers

Conniff highlights twenty-first-century “networked pirates.” Taiwan’s Sunflower Revolution used “forked” mock-government websites to outpace bureaucracy and redefine digital democracy; civic hacker Audrey Tang later became Taiwan’s first transgender minister. Meanwhile, the “platform cooperativism” movement builds fairer digital platforms—like FairBnB or driver-owned taxi apps—to rival exploitative giants like Uber and Airbnb.

Even activism mirrors pirate networks. Avaaz, one of the world’s largest online campaigning communities, coordinates millions with a microscopic staff—proving that in the digital era, power comes from connection, not control. Pirates would’ve understood perfectly.

The fourth pirate rule might be the most radical: real rebels share power. Conniff insists that once you’ve built a new system, you must protect it from corruption by distributing authority, reward, and risk fairly. Otherwise, rebellion turns into tyranny under a new flag.

Equality by Design

The pirates practiced what leaders today only preach. Crews elected captains, voted on decisions, and enforced “no prey, no pay”—a transparent profit-sharing scheme. Both the captain and quartermaster held equal power, creating an early “two-house” governance model centuries before modern boards of directors or democratic parliaments. They even introduced injury compensation and social insurance aboard ship—a moral and economic innovation unmatched until the nineteenth century.

Their shipboard democracy ensured no one man’s authority could destroy morale or mission. As Peter Leeson notes in The Invisible Hook, these egalitarian systems were not altruism—they were survival strategy.

Modern Pirates of Purpose

Conniff connects pirate fairness to today’s social enterprises—companies designed to do good while making money. His own enterprise, Livity, redistributes power by letting young people lead projects for major brands, merging business success with youth empowerment. This is “business as unusual”: purpose-driven, transparent, and collaborative.

He also profiles ethical entrepreneurs like Kresse Wesling of Elvis & Kresse, who built a luxury brand from recycled fire hoses and pledged half its profits to firefighters’ charities. Like pirates, Wesling measures success not just in profit but in impact—waste diverted, artisans trained, and fair practices maintained.

From Booty to Balance

Redistribution, Conniff argues, is the true test of leadership. How you share credit, profit, and decision-making determines whether your revolution sustains itself. Just as pirate crews marooned selfish members, modern teams must guard against inequality and exploitation. The goal isn’t charity—it’s shared ownership, where everyone invests in the mission’s success. Like pirate democracy, fair systems are stronger systems.

The final pirate principle is storytelling—because every meaningful rebellion needs a legend. Pirates were master propagandists, turning fear into fame through symbols, theatrics, and mythmaking. Conniff invites you to ‘weaponize your story and tell the hell out of it.’

Branding Like a Buccaneer

Pirates invented branding. The Jolly Roger flag—skull and crossbones on black—was the eighteenth-century equivalent of a global logo. When Blackbeard set fuses in his beard to appear demonic, he wasn’t courting chaos; he was cultivating an image of terror so strong that his victims surrendered without a fight. His violence was psychological branding—fear as efficiency.

Modern entrepreneurs do the same, with values swapped for visuals. Authenticity and audacity still win attention. Conniff reminds you that your story is your power: audiences resist facts but remember emotions and myths. Your flag—the image or message that represents your cause—should provoke recognition and rally community.

Stories that Change Systems

Throughout history, stories have dethroned kings and inspired revolutions. Douglas Burgess demonstrates that pirate narratives influenced the American founding fathers, who admired the pirates’ defiance of monarchy and built similar ideals into the Declaration of Independence. Centuries later, activist and blues musician Daryl Davis dismantled racism one conversation at a time by befriending Ku Klux Klan members—literally converting them through dialogue. His quiet bravery exemplifies storytelling as activism.

Conniff also celebrates street artist Banksy, whose art turns walls into dissenting voices. His anonymous identity, biting humor, and social commentary embody pirate principles: subversion, imagination, and message over ego. As Banksy says, “The greatest crimes are not committed by people breaking the rules, but by people following them.”

Entering the Lion’s Den

Conniff closes with a challenge called the “Lion’s Den”: share your story where it’s least likely to be welcomed. Like pirates sailing straight into enemy harbors, telling your truth in hostile environments amplifies its power. The more resistance you face, the more visibility your cause gains. That’s how pirates became legends—and how ideas, once feared, become movements embraced.

Conniff ends with the anchor of the pirate philosophy: codify your rebellion. The Pirate Code wasn’t just lore—it was law. Contracts like Captain Henry Morgan’s or Black Bart Roberts’s spelled out equality, fairness, and discipline. These codes gave pirates structure amid chaos and clarity amid danger.

You can do the same by creating your own “Pirate Code 2.0,” a set of principles to govern your team, business, or personal mission. Write down the rules you live by: how you make decisions, share power, resolve conflict, and measure success. Keep them short, memorable, and sacred.

For Conniff, a code works because it turns good intentions into habits. It enforces accountability—the pirates literally signed theirs in blood. Modern accountability doesn’t require cannons, but it does require consequence: if someone breaks the code, what happens? Whether that means a lost privilege or a coffee-buying penalty, enforce it. Rules without repercussions are myths without teeth.

Conniff draws a poetic line from pirate articles to cooperative charters, social enterprises, and even startup manifestos. The cooperative movement’s seven principles—voluntary membership, democracy, shared profit, and concern for community—mirror pirate values almost exactly. Our modern world, he argues, could reclaim stability and fairness if it honored such codes again.

So design your own. Keep it alive by revisiting and revising it as you grow. The code is your compass. It helps you steer through uncertainty—and stay true to your cause when the seas get rough.

Conniff closes with a challenge worthy of a captain’s log: answer the call. You’ve learned from the legends, now you must write your own. The point isn’t to imitate pirates but to embody their courage, creativity, and irreverence in your context. You don’t need a ship; you need intent.

He warns against becoming like Stede Bonnet, the ‘Gentleman Pirate’ who tried to buy rebellion without belief. True piracy—true change—starts with knowing yourself. Identify the one rule that holds you back, the system worth defying, and the ideal worth defending. Then act. Start small, sail steady, and expect resistance. History won’t remember those who followed orders—it remembers those who broke them for good reason.

Like the pirates before you, find your crew, write your code, and cause some good trouble. In a world still ruled by the few, the hour has come again for the many to mutiny. Your piece of the revolution starts wherever you drop anchor.