CHAPTER 4

PARADOX OF PIRACY

If you’ve ever thought your past—whether personal or professional—is the barrier to your individual future, read on.

Our next Bold One was never accepted into a highbrow university, and most think she couldn’t even read or write. In fact, her first profession was probably the oldest one (yes, that profession), and for almost her entire life, she was an outlaw.

If you’ve ever doubted one person’s ability to rule her own empire, let me introduce you to Ching Shih, the most successful pirate in history. If you thought Blackbeard or Redbeard (or even the mythological Captain Jack Sparrow) was a force of infamous and swashbuckling heroism, just wait until you hear about Ching Shih.

Like many legendary human beings, less is written about her than historians would like. What has been written has been contradicted. What has been passed down is often exaggerated, or, conversely, underreported. The truth lies somewhere in the midst of all the rumors. I’ll share the research, and let you decide what’s true. But there is one fact many pirate enthusiasts and historians agree on: No pirate in history was as successful, culturally or economically, as Ching Shih.

In the early 1800s, under the waning power of the Chinese Qing dynasty, piracy was alive and well. Likely to attract visitors to their ports, the minorities within the Canton region (modern Guangzhou) had a unique offering called “flower boats.” On these ornately decorated boats, young ladies would meander from ship to ship, offering services to the young sailors, such as dancing, companionship, and sometimes intimacy.

Here, as a flower-boat girl, Ching Shih found her first career success. She was smart, interesting, and, of course, beautiful. By some records, her reputation had put her in high demand among the other young ladies, and she ultimately claimed many high-profile pirates, politicians, and businessmen as her regular clients. Because of her clientele, she’d hear rumors, gossip, and inside dealings. She had as much blackmail fodder as she did beauty.

One of her clients, a pirate captain named Zheng Yi, was the leader of the well-known and feared Red Flag Fleet. Infatuated with Ching Shih, one evening he ordered his men to kidnap her. They tied her up and brought her to him. When she arrived, he asked if she’d like to marry him. The henchmen untied her so she could give her answer—bad call.

As the story goes, “When she was untied in order to give her answer, she sprang at him like a banshee and attempted to claw his eyes out.”¹ (I guess none of the pirates had read Getting to Yes at this point in their careers.)

Nonetheless, Ching Shih and Zheng Yi negotiated. She agreed to marry him under the condition that she would own half of all his fleet. Amazingly, he agreed, and the two quickly became the Bonnie and Clyde of the high seas. Zheng Yi came from a long line of ruthless pirates. Ching Shih had blackmail and other critical information on many of the most powerful people in the known world. Under their combined leadership, they organized the entire pirating community into a strict, hierarchical structure. Ching Shih believed that by working together instead of constantly having “turf wars,” the pirates could all enjoy more wealth. They rallied the entire pirating underworld—some 50,000 pirates and hundreds of vessels—under a confederation of about a half-dozen pirate leaders, organizing them into territories, assigning rank, and having each report upward, ultimately to Ching Shih and Zheng Yi.

If you’ve seen Pirates of the Caribbean 3, then you may remember a character, Mistress Ching, sitting at the table of the nine Pirate Lords. Many speculate that the writers of the film modeled her after Ching Shih. But even that’s not giving her enough credit. The truth is, the entire concept—of a roundtable of rule-abiding pirate leaders—is owed, at least in part, to Ching Shih.² One of her lasting pirate legacies is the enforcement of a code. Perhaps influenced by her upbringing, she enforced a strict set of rules in her private kingdom: no stealing, desertion, or rape. Women were to be treated with respect at all times.

After her husband passed, Ching Shih not only seized the helm of the pirate confederation but expanded it. The desperate Chinese government tried everything; yet Ching Shih’s military prowess and organizational skills allowed her to not only evade capture, but continually defeat armada after armada from the Chinese government. Ultimately the government asked for help from the Dutch, the British, and the Portuguese. Everyone tried—everyone failed.

At her height, Ching Shih commanded 1,800 large ships and smaller vessels—more than the modern navies of the United States, China, Russia, and Japan . . . combined. She also ran an empire of up to 80,000 men.³ By comparison, Meta (formerly Facebook) had about 77,000 employees in 2022.

Perhaps the greatest part of Ching Shih’s legacy is that she recognized that the pirates—known for disorderly conduct and inbred fighting—needed organization and unity. For tyrants who steal and kill for a living, formal organization is a disruptive paradigm. By sensing the need and executing on it, Ching Shih capitalized on her moment, seizing an opportunity that others had been unable to capture. There was a harvest of opportunity available, and it took an inexperienced pirate to take the real treasure.

Being bold enough to create a hierarchy and a code (the very things pirates hated) required an individual like Ching Shih, who was a bloodthirsty, fearless tyrant.

Now fast-forward about 200 years, and leave the waters of the high seas for the garments of fashion. In the 2010s, the beauty and intimate apparel industries had problems as obvious as those of the nineteenth-century Chinese pirates, and again it needed a Bold One to disrupt them both. So in 2017, in walked another heroine from across the seas, this time from Barbados:

Rihanna.

Rihanna, having already taken the music industry by storm, set her sights on the beauty industry. For years, it had been plagued by an ineptitude to create colors, tones, and makeup for anyone but light-skinned women. Particularly among minorities, the problem was obvious.

True, a few notable, niche companies served their respective communities, but “Rihanna” wasn’t a small name. And she wasn’t about to settle for anything less than the whole fleet.

Her first major collaboration was with LVMH—the most prolific luxury brand in the world. Rihanna didn’t just make a small handful of diversity-friendly tones; instead, she filled a kaleidoscope with 40 different shades. She released her Beauty Fenty line with LVMH, and within 40 days, the line had sold $100 million in product.

But Rihanna wasn’t done.

She set her sights on the intimate apparel industry, where exactly one tall, white giant had ruled for decades, Victoria’s Secret.

Rihanna aimed her cannons right at their mast—the lingerie runway show.

Rihanna unashamedly took their own models, poaching six Victoria’s Secret “angels” and renaming them “savages.” Then she collaborated with Amazon—the dirty dog of retail—to host her own catwalk show, one that celebrated women of all colors and all sizes. Unlike its competition, Rihanna’s show highlighted mostly female acts, and all the marketing—from the choreography of the dancers to the diversity of the models—was aimed at the desires of women, not the eyes of men.

Within a year of Rihanna’s Savage Fenty show, Victoria’s Secret—a 44-year-old company—had lost sales, its stock was sinking, and its runway shows were canceled; then, in 2021, its parent company announced they’d be spinning the brand off into its own company. That’s the power of being bold.

In 1800, everyone knew that the underworld needed order.

In 2000, everyone knew the world of underwear needed disruption.

In both cases, it took a Bold One to rewrite history.

CREATE A CULT

Let’s begin this section by defining the word cult. A cult is a small, rugged offshoot of a larger system. A cult breaks off the mainstream, going rogue before it ever becomes popular and attracts the masses.

In one of his most famous quotes, renowned science fiction writer L. Ron Hubbard, the author of Battlefield Earth, once supposedly said, “You don’t get rich writing science fiction. If you want to get rich, you start a religion.”^{4, 5}

Hubbard, who also founded the religion Scientology, was casting light on something even more profound than the relationship between finances and religion. He was showing that if you really want to influence people, you’ve got to create a following so intense, so dedicated, that in the end you don’t just have an audience who’s following a brand. To influence the world, you need a cult.

This might sound extreme, but hang with me. Think of the most influential brand names and properties in the world—the ones that constantly attract outsized attention from the media, top talent, and partners. Immediately, you’ll notice two things.

One, it’s not usually the company, but one person, such as the founder or an individual creator, who’s attracted all the attention. When you think about Apple, you think of Steve Jobs. When you think about Harry Potter, you think of J. K. Rowling. When you think about Microsoft, Tesla, or Disney, you think, respectively, about Bill Gates, Elon Musk, or Walt Disney. In many cases, we don’t even think about the company at all; more people are familiar with Warren Buffet than with his company, Berkshire Hathaway. People are more likely to recognize Oprah than her production company, Harpo Productions.

In a sense, these individuals have become mini-religions.

The second thing you’ll notice about the most iconic brand names in the world is the level of intimacy that these founders sometimes inspire among their followers. For instance, when Steve Jobs passed away, Apple created a permanent scrolling feed for Steve Jobs’s idolizers to post their feelings:

“His legacy will be eternal.”—Gabriel

“Today we lost a visionary genius.”—Mary

“A true human hero.”—Hugh

Eternal. Visionary. Hero. Those aren’t words you’d typically leave on a feedback form after visiting an electronics store to pick up a laptop. Those are the kinds of things people say when an icon has passed.

For something truly disruptive—such as a new product, a revolutionized platform, or a creative method of accomplishing an outcome—we’re eventually going to need a dedicated following—a devout group of individuals who turn into employees, evangelists, and partners.

How do we do that? How do we build a following that dedicated? How do we become the pirate captain of our own fleet and create a cultlike following that will come behind us as we break down the walls of the institutions? There are five steps we can learn from our two pirate heroes and other leaders:

STEP 1: INSPIRE THE UNDERDOGS. Notice how Ching Shih and Rihanna didn’t go after the main cohorts and demographics of their marketplaces? Instead, they inspired loyalty among those who’d been marginalized by others.

STEP 2: CREATE A HALO EFFECT. It’s possible to do something so revolutionary and awe-inspiring that whatever you do next will have the touch of the gods. Rihanna can start any business she wants—she goes from music to lingerie to skin care—because to her followers, she walks on water.

STEP 3: CAPITALIZE ON FRACTURED MEDIA. You actually have an advantage over Ching Shih. It’s easier now, more than ever, to reach a niche following. The world has splintered, and as a result has created an endless number of channels for leaders and followers to connect over unique interests, passions, and ideas. You can utilize these channels to reach a small but dedicated fan base.

STEP 4: UNDERSTAND THE PARADOX OF PIRACY. You must keep in mind what I call the “paradox of piracy,” a seeming contradiction that suggests if you want to go broad in the long run, you’ve got to start by thinking niche in the short run.

STEP 5: AVOID THE DARK SIDE OF THE CULT. What happens when you build walls so high on your status that they create an echo chamber, one where no one dares challenge you? The better job you do at creating a cultlike following, the harder it will be to disrupt yourself. Be on guard against the dark side of the cult.

Let’s dive deeper into each of these key concepts.

STEP 1. INSPIRE THE UNDERDOGS

Typically, a cult attracts the underdogs, those that everyone else has overlooked. While 90 percent of the world looks at the same cohorts, demographics, and geographies, Bold Ones think differently.

Victoria’s Secret maintained its domination for a long time by doubling down on exactly one body type. The company even knowingly ostracized others; as their CMO Ed Razek infamously remarked to Vogue, “I don’t think we can be all things to all customers.” However insensitive, Razek’s comment made sense in old-school thinking: optimization for the greatest ROI. Wielding its monopolistic stranglehold on the industry, the company had little reason to negotiate with fringe needs. Before 2018, if you wanted luxury lingerie, you shopped at Victoria’s Secret. That was the option. But Bold Ones think differently. They look internally and consider their own authentic voice, culture, and experiences. They recognize they don’t have to compete for that singular, sought-after demographic. Instead, they can remain true to a central group of people to defeat institutionalized incumbents. They can create their own cultlike following from a dedicated, small group of believers who are willing to sail with them into uncharted waters. While institutions always look down on these fringes, Bold Ones embrace them.

When others are looking to hire from Ivy League institutions, Bold Ones ask where the untapped potential is in the warehouses. While incumbents chase the same celebrities, geographies, and talent, Bold Ones are looking to get out of the mainstream and into the less-crowded, overlooked areas of society.

One of the greatest heroes in Jewish culture is King David—you know, the one we all talk about in the David versus Goliath story. But there’s a lot more to his story than a towering giant and a slingshot-wielding underdog.

Before David became king, he was actually an outlaw to his own people. The king at the time, Saul, wanted to kill David out of jealousy. So David ran off to hide in the middle of the mountains. That actually became his setup.

While up there in the crags, he started making friends. Not friends from the nice nobility of the palace, but criminals, outcasts, and lonely people. Even foreigners—a big no-no in Jewish culture of that day—became his closest friends. David started to create an unexpected and loyal following.

David eventually overcame his outlaw status and became king of Israel, and what people did he bring with him? That band of brothers. They become his elite fighting force.

Here’s the thing about niche crowds: When you befriend them, they’re fiercely loyal. Once, during a war, King David complained that he didn’t have any fresh water. Do you know what the elite men in his army did? Attacked another kingdom, just to get clean, fresh water for David.

That’s loyalty. That’s the kind of emotional connection you breed when you root for the underdogs.

You can do the same by looking for a niche cohort in forgotten areas: in a talent pool, in an underserved market, or in a disaffected geography. Ching Shih embraced the outlaws; Rihanna embraced multiple skin tones. Whom or what can you embrace? While everyone else is distracted by the majority, those on the fringe, forgotten and lonely, are ready to be awakened. Plus, there are fewer gatekeepers, less rules, and usually no competition.

So how do you embrace the underdogs?

I have four suggestions, starting with your audience.

BE CLEAR ON YOUR AUDIENCE

Create your offerings or content with target personas in mind. Building a community of supporters that grows with you is one of the hardest things to do, so you want to get this right.

If you’re trying to inspire the underdogs, be clear about who those underdogs are, specifically. When you’re building out content, creating products, or taking a stand on an issue, make sure everything is aligned to attract those you’re trying to inspire.

In his book Content-Based Networking, author James Carbary says it like this: “Work backward from the exact goals you have in mind, from the place you want to end up, [and] the connections that you need.”

One of the best connections that you can make? A connection with the “number two” person in an organization.

LOOK FOR THE NUMBER TWO

Malcolm Gladwell, the famous author and thinker (another Canadian!) talks about learning from the number two person, not the head leader. Everyone wants to speak with the CEO of a company or the president of a nation. But while the top dogs have inundated inboxes, the number two person within each organization is just waiting for the chance to share their story.

Not only are you more likely to get a response from someone in this position, but Gladwell points out that you’re actually more likely to get the real truth from these individuals as well, because they aren’t constantly filtering everything through a list of PR-whitewashed filters; the number twos—like the executive assistant, campaign manager, or vice president—are more likely to be bold, unafraid, and willing to share their real thoughts. So, as you’re building out your cultlike following, don’t get distracted by the celebrities or the demographics stealing 99 percent of the world’s attention.

CONNECT AND COLLABORATE

Collaborations are essential for growth. Essentially, look for an opportunity to work with others in a real way, even for free. This could be a small project, a piece of content, a new podcast, or a mini-project. Is there a side project you can take on at work? Can you build a piece of content with others that allows you to build out your network? Remember, you don’t always need to be captaining the ship.

TRUST ISN’T BUILT OVERNIGHT

When you’re first building your fleet of influence, you’ll need patience. Focus on delivering ridiculously high-quality, meaningful offerings to your audience or team members. If you’re in a position to hire team members, give them ample opportunity to pursue their favorite projects. If you decide to build out a YouTube channel for your audience, forget making money, and instead ask yourself, “What does my audience need that I can provide?” If the people in your audience need to hear from an expert, find experts for your show. If they need real-world examples, offer them. If they need a template, hop on Google Docs and build one.

If you’re consistent with delivering value, your audience, teammates, and partners will reward you. I’ve been posting a video every week on LinkedIn for almost four years. It took some time to get any real traction; now I have thousands of followers across my platforms. Build the habit, and focus on value.

STEP 2. CREATE A HALO EFFECT

Creating a cultlike audience that will follow you into the depths can be difficult, but there is a trick—a hack, if you will—that you can use to do something disruptive. Similar to the 3% Rule, this one is a time-tested tactic that’s simple to copy.

It’s called the “halo effect.” Originally coined by one of the most prolific and cited psychologists of the 1900s, Edward Thorndike,⁶ a halo effect occurs when you do something so spectacular that, by association, anything else you do has a ring of angelic grace to it. With the halo effect, once you’ve executed in one area with awe-inspiring diligence, your community now views everything you do with anticipation and, likely, appreciation. There are lots of example of how this works, but my favorite is Kanye West and Adidas.

The controversial rapper, self-proclaimed fashionista, and one-time US presidential candidate got fed up with the shoe company he was repping, Nike. So he dropped them, and in 2013, he walked a couple of blocks over to a competitor, Adidas.

In the early 2010s, the Adidas brand was stagnating, while others, particularly Nike, were gaining market share. Always a rebel, Kanye didn’t want to be a simple brand ambassador for Adidas. He wanted to take the company into a whole new niche: lifestyle sneakers. It wasn’t something Adidas was known for, but they gave Kanye the go-ahead, and a new collaboration was born: “Yeezy.”

It was a hit.

Kanye’s Midas touch gave the entire company a brand lift, ushering in a new breed of consumers, and the entire Adidas brand enjoyed a resurgence in popularity. At the time of writing this book, Kanye’s relationship with Adidas has been strained—that’s a whole another story!

Kanye took his own halo, built on his fan base from music, and applied it to an entirely new product. Fans liked Kanye, so they liked Yeezy: halo effect. Adidas was thrilled:

Not only [have the Yeezy’s] sold out instantly, but [they’ve] also played a major role in propelling Adidas to the most popular sneaker brand on Instagram in 2015.⁷

How can you apply a halo effect to your own career and personal brand? What’s something you can create that’s stand-alone enough, unique enough, and authentic enough to you, that it casts an angelic light over everything you do, one that will follow you as you keep pushing for disruption? Say you’re a real estate mogul who’s into racing electric vehicles as a hobby; why not start a blog about it? It’s low-investment, you enjoy it, and if you can become an expert in one area, it gives you the appearance of expertise in all areas.

Perhaps my favorite example of a halo effect comes from two French brothers, Édouard and André.

In the early 1900s, the brothers owned a tire company. In an attempt to generate more sales, they created a world-class restaurant rating book, called the Michelin Guide. Originally, they thought they could push more people to drive farther distances, thereby increasing the demand for new tires. However, the guide quickly became so well respected in the restaurant industry, that its real power is that the name “Michelin” now stands for world-class quality in two areas: top-rated restaurants and excellent car tires.

BUILD A PERSONAL MOAT

Medieval rulers defended their positions by placing moats around their castles. Today, a personal moat around your own brand allows you to possess something that’s so uniquely your own, it’s essentially a personal monopoly.

There are myriad ways to build a personal moat. You can combine various skills (like law and cryptocurrency), layer in locality on top of your expertise (like “the best real estate agent in Sedona, Arizona”), or just be the only expert in your field who’s also a black belt in karate. 

Take Kiersten and Julien Saunders, personal finance experts who also have a passion for cooking. They created an entire WebTV series called Money on the Table, where they bring financial conversation to their own kitchen table as they cook a meal. With that, they’ve created a unique personal brand; and in 2021, a major studio contacted them to start recording their first “real” TV episode. Then, in 2022, they dropped their own book, Cashing Out. Who can compete with fantastic cooks who also know everything there is to know about finances?

I’ve tried to add this personal moat into my own life. At my keynotes, I speak about disruption. By itself, that’s not much of a differentiator. However, I’ve raised a flag around my brand by combining pop culture with disruption. While others focus on technological disruptors, I use references that are part of the cultural zeitgeist. Using a strategy commonly referred to as “newsjacking,” I’ll grab a current event and connect it with a broader idea.

Look hard enough, and it’s not difficult to understand your own style, and that’s your differentiator. You may be a nurse practitioner, and, sure, there are lots of nurse practitioners. But few of them are likely to care about the same sports teams as you do. Perhaps you’re a software developer, and you have a lot of competition. But do your colleagues know that you also double as a comedian? (Scott Adams, a developer, found a new core when he became the author of the renowned comic strip Dilbert.) Perhaps you’re one of a thousand auditors in your Big Four auditing firm where most want to work the biggest-name clients; does everyone know that you love working with the smaller clients?

Ultimately you want to find something that is portable and tactical and that only you are known for. You want to associate yourself with a specific artifact—whether a niche type of content, a specific community, or a particular skill set—that others can point to and say, “Ah, that’s their thing.”

Start building out your authentic personal moat, and make your castle unique.

IF ALL ELSE FAILS . . .

There’s a story someone on my media team told me about his friend, Brandon, who’s now a voice actor working on video games.

He got into the highly competitive industry by starting at Disney World. With no prior knowledge of the industry, no real hard skills, and no experience, he took a high school acting class and told his teacher he wanted to audition for Disney. The teacher gave him one single piece of advice:

Make sure they remember you.

He used the example of someone who was trying out for the male lead in Romeo and Juliet. Likely, dozens (if not hundreds) of men wanted the part, and they had all memorized the audition scene to perfection. But then, one man did something the casting director couldn’t forget—he climbed up the curtains to reach for an invisible Juliet as he read his lines.

Guess who got the part?

If you can’t quite think of how to differentiate yourself, lean on your quirks, interests, and those things about you no one else does quite like you, even if they aren’t directly related to your expertise. If all else fails, make sure they remember you.

STEP 3. CAPITALIZE ON FRACTURED MEDIA

Reaching a lonely, ostracized community has become easier as technology has shifted. While working on the flower boats, Ching Shih had to spend time with each individual to extract knowledge she’d need to leverage later: one hour of time for one hour of information. But now? You can scale her efforts in a way never possible before. You can double down on Ching Shih’s genius, even without her singular personality or rare opportunities.

With social media, people from the other side of the globe can get in your head. They can hear your thoughts on politics, business, and socioeconomics by following you on social media. You can feature your art on Patreon, allowing fans to support you financial. With the revolution of direct-to-consumer sales, you can be a pirate in your world, a one-person show. Whatever niche community of people you are attempting to reach, you can find them at the click of a button.

Plus, we don’t all have to buy into one common narrative anymore. We have multiple options of what to consume, believe, and understand.

Previously, certain gatekeepers told society what to think, how to act, and when to buy. For much of history, advertising, media, education, and other distributors of information created a familiar few narratives from which followers were allowed to choose. For centuries, the Catholic Church dictated when you could work, how you could perform medicine, and whom you could marry. Before the church, there was the Roman Empire. Before the empire, there were the Egyptian pharaohs. While a few notable individuals broke through these institutionalized boundaries, the gates were high.

Today the smartphone has become the new church. It dictates every aspect of our lives. The difference between the old churches and this new church is that the new church is hyper customized to the individual. Attention has been fractured into a billion pieces, and the smartphone has become a portal for us to engage with anyone all over the world.

I worship Bill Simmons. I wait every Sunday evening for the new Bill Simmons piece to hear his takes on the NBA and pop culture. I’ve never talked to or met Bill Simmons in my life, but I’ve listened to more than a thousand of his hour-long podcasts. I hate to admit this (and I’m sure Bill Simmons would hate to admit this too), but because of the phone, I am part of the Bill Simmons cult.

Look at Joe Rogan, the Kardashians, Alexandria Ocasio-Cortez, Steve Jobs, Jordan Peterson, or Donald Trump. All of them have inspired cultlike followings purely through a screen. Their political leanings are conflicting, and their fields are varied; yet all of them have reached those who are willing to argue, fight, and lose friends over their causes. Extreme? Yes. Effective? Absolutely.

In our case, we can leave the controversy and still capitalize on the fragmentation. This new wave of diversified media provides a global audience, making mass connection possible through just one device. You can exercise your influence over a niche, but expand that influence across the globe. A Bold One could not only learn, but master, infiltrate, and completely derail the course of an industry from the confines of home. While we used to hear “Every company is its own media company,” now we can also say “Every person is their own media company.”

You and I must capitalize on this opportunity and begin to inspire our teams or followers.

To capitalize on this fragmentation, you need to build a unique advantage around your personality. Next you also need to find the right medium for that personality, the right channel that can carry information.

FIND THE PERFECT MEDIUM

Once you’ve started creating your own personal brand, you must display it on a medium that can garner attention, one that fits well with your information and your community.

Whether it’s video, audio, writing, events, text messages, or group chats, place your ideas on a platform that has the ability to reach one more person. Find the medium that best suits your personality and skills. One more supporter tomorrow is two more supporters next month, and four the month after that.

“SHIP” IT

Since we’re on pirates, let’s talk about the word “ship” for a moment. This is where a lot of people get it wrong. They don’t ship their content. They don’t click the “send,” “upload,” or “post” button. They do all the work but never publish that content, or send the email to the connection they want to make, or show up at the coffee shop to meet with the new potential partner. When you’re building an audience, a fan base, connections, coworkers, or content, you need to go for it. Get a little uncomfortable, and start making moves.

Step 4. Understand the Paradox of Piracy

When bold pirates are willing to inspire the underdogs, capitalize on fractured media, and create their own halo, they discover what I call the “paradox of piracy.”

It’s a seeming contradiction, but it’s a simple premise: When you aim for a fringe, you ultimately attract the masses.

You can start a radical journey on a flower boat, but end up as the captain of the world’s largest naval confederation. When you create a following so deep, so devout via your own authenticity, ignoring whatever is considered “the masses” to devote yourself to the few, you’re able to create something so worthwhile, everyone wants to jump on board.

Rihanna’s success with fringe skin tones parlayed into a broader culture. In 2019, when the luxury lingerie brand announced it was canceling its renowned fashion show, Rihanna did her first. While Victoria’s Secret announced it was closing nearly 250 locations in 2020, Savage X took its first dive into physical stores. “Savage X doesn’t hold any punches, and it’s all gas, no brakes,” Rihanna said in an interview with Refinery 29.⁸

For a while, major institutions—such as banks, Fortune 100 businesses, and universities—had all the power. Much like their concrete structures, their influences were cemented into our hearts and minds—their power towered over our ambitions, casting shadows everywhere.

But people would rather follow Anderson Cooper over CNN. In sports, people often cheer for their favorite players, regardless of what jersey they wear.

People more devoutly follow individuals, not brands. Humans want to be part of what’s bigger than themselves: a movement, an ideology, something that has meaning and purpose.

You can start small, with your niche audience; but in the end, the reward is, you capture the attention of the masses. If you want to change the game, start with one piece. If you want to disrupt an incumbent, look for a fringe group that was missed. If you want to upset an industry, go find one fan, and deliver insane value to them.

That’s the paradox of piracy.

STEP 5. AVOID THE DARK SIDE OF THE CULT

To achieve disruption, you’ll need devotion and resilience from a fearless group. The only way to achieve massive disruption is to think fringe, first.

The beauty of such a following is evident, but there’s a dark side of creating such a fan base. Eventually, you could gain so much attention and success, that you’ll wrestle with what every incumbent institution faces—having to break out of the high walls you’ve built around yourself. Boldness is easier when you have nothing to lose.

If your dedicated audience expects you to act one way, what if you behave in another? If you built your reputation on the back of a hard stance on remote work, what will “they” say when your opinion shifts?

Social media makes this even more challenging. The more you lean to a particular side, the more attention you receive. The algorithms push the most outlandish ideas because that’s what generates the most engagement. I’ve seen the algorithms turn thought leaders into caricatures of themselves.

Breaking out of a mold you’ve created can be challenging, but it can be done.

Consider Howard Stern. I’ve listened to the self-proclaimed “King of All Media” since 2007, and I can tell you that he’s changed in both tone and substance. Originally he was brash, unapologetic, and provocative. He gained an audience with his unique style. Over time, he’s toned that all down significantly. Plus, his political views have drastically changed. In today’s world, those aren’t easy swings to make. But with a willingness to evolve, you can constantly disrupt yourself, and avoid being disrupted by an external force.

I have one piece of advice that will help ensure you never succumb to the seductive pull of success or algorithms:

Create your own advisory team.

The greater your status, the less likely fans will guide you when you’re off track. They won’t feel the need—or ability—to speak up. That’s why you need to intentionally surround yourself with people who will call you out.

Create a fearless advisory team who don’t get mesmerized with status. Empower them to challenge you. This doesn’t have to be complicated. You just need a group of tight individuals whom you trust to give you honest feedback. Personally, I have a WhatsApp group—ironically called “Kardashians”—with some of my absolute closest friends. I use it for my brain dumps, ideas, and vulnerabilities. If any one in the group makes a comment about my tone or substance, I immediately listen. I don’t want to build an echo chamber. I want outside influence, and a broad view of the world. Go get your own advisory team together.

EVEN PIRATES RETIRE

Ching Shih faced the dark side of the cult at one point in her career—she’d outmaneuvered much of the globe’s Eastern empires. She’d outcommanded their navies and outpirated the greatest buccaneers of her day. But pirating can only last so long. When she decided to disrupt her current career, to retire, she couldn’t exactly settle down to a normal life with a 401(k) and a beach house in the Florida Keys. In perhaps a stunning pivot, Ching Shih decided to negotiate her surrender in 1810.

This move was one of her boldest yet—no guns, no men, just an appeal to the Qing government. She marched up to the governor’s house, armed with nothing more than other women and children, to boldly negotiate, face-to-face, with the enemy. She offered to stop all piracy, under the condition that none of her fleet’s stolen goods would be returned. She also demanded that the Chinese government not only pay her, but pay the men under her as well.

The government accepted the terms.

One woman united the entire underworld and routed China for years, escaping every known navy on earth. And then she died peacefully in her own home.

Even while creating a cult, she kept the longest view in the ocean. While she was enjoying success on the open seas, she knew it wouldn’t last. She allowed herself to evolve, even past her own successes. Many may have thought that she’d drifted so far out into the ocean of treachery, she could never return to normality. But she proved them all wrong.

She was willing to disrupt herself, even to the end. That’s the final lesson we can learn from Ching Shih: Never stop disrupting yourself, because even pirates can retire.

SECRETS OF THE BOLD ONES