Uncharted Waters: How Radical Vulnerability Shifts Culture
Pirate Crews, Greedy Investors, and Other Lessons
I’ve always appreciated the idea of radical candor: telling it like it is, respectfully but directly. Yet over time, I realized that candor on its own can ring hollow—especially when what’s behind the message isn’t fully disclosed. That’s where radical vulnerability comes in. If candor is the “what,” vulnerability is the “why,” complete with all the messy motivations, constraints, and even doubts.
When a Captain Loses the Crew
History offers a surprising model for this: pirate ships. Contrary to the Hollywood trope of a lone captain barking orders, many 17th- and 18th-century pirate crews operated under a form of democracy. The crew voted for their captain, elected a quartermaster who managed day-to-day discipline and loot distribution, and spelled out “Articles of Agreement”—clear rules about conduct and shares of treasure.
Why? Because pirates knew a high-stakes secret: if you don’t trust your captain, you mutiny. The captain had to be transparent about their decisions—where they were sailing, what risks they’d take, and how they’d split the spoils. A quartermaster existed to keep the captain honest, ensuring that when the captain said “We’re venturing into hostile waters,” it wasn’t just a self-serving move to boost the captain’s cut of the loot.
“Better to lose half a share of gold and keep the crew than end up sailing alone.”
(A maxim many successful pirate leaders lived by—though rarely so neatly stated.)
This forced radical vulnerability from the top. If the captain withheld real motivations—like personal greed—the crew sensed it, rumors spread, and eventually, they’d vote the captain out (or worse). That’s democracy on the high seas.
Modern Workplaces: When Spin Replaces Truth
Though most of us aren’t fighting the Royal Navy or raiding merchant ships, the parallels are strong in high-pressure work environments—especially in tech, agencies, and professional services. Leadership often demands extraordinary hustle (the “stormy seas”) while holding tightly to information about profit margins or future plans (the “treasure”). Employees become disengaged or even hostile when they sense there’s more to the story.
I’ve lived this firsthand. Over and over, I’ve been asked to deliver bad news—budget cuts, hiring freezes, or withheld raises—while knowing full well the decision was driven by shareholder greed or executive comfort. Publicly, it was framed as “protecting the company.” But anyone paying attention could see the real reasons, and that’s where trust frays.
Tech history is dotted with cautionary tales where top leadership failed to be vulnerable:
WeWork’s Adam Neumann famously promoted a vision of community and revolutionizing work culture while allegedly making self-serving decisions behind closed doors. When the real motivations surfaced (personal payouts, chaotic financials), employees and stakeholders lost faith overnight.
In contrast, Buffer, a social media management platform, took the opposite tack. They practiced radical transparency with public salary formulas and open financials. Critics said it was risky, but by sharing the real “why” behind decisions—like how salaries were determined—they built a loyal “crew” who felt the system was fair and honest, even if not perfect.
The Moxy Ox Example: When Investors Deny Vulnerability
A stark lesson in how a refusal to be vulnerable can doom a company played out when I was head of Moxy Ox. We had investors who were inexperienced, prioritizing quick profits in ways that bordered on greed. One of them candidly said, “It’s time for us to go to the ATM,” referring to pulling out their investment just one year into our startup journey—effectively trying to raid the ship’s coffers before our brand fully set sail.
Despite my delivering stellar year-over-year revenue growth (100%, then 190%, then nearly 400%), the investors wanted an even bigger leap the next year—2.5 times that massive 390% jump. It was unrealistic to the point of absurdity. I told them, “I won’t work for a wage that doesn’t reflect the job, nor will I expect the team to.” Committing to that wild new target would have broken our operations and our credibility with customers. Instead, I proposed 1.7 times revenue growth—which was still lofty.
They promptly “voted me off the ship.” Once I left, it only took half a year for 95% of the team to turn over. My cofounder left soon after. Morale plummeted, clients wavered, and the business never regained its footing. All because the investors wouldn’t be honest about their short-term objectives—or the risks those demands imposed. They refused to align with the person (me) who had led them to success in the first place.
Had they owned up to their motivations—“We want a faster return, and here’s why we’re pushing for such high numbers”—we might have found a balanced path. Their inability to show vulnerability, to acknowledge the greed factor, cost them the very team that made them profitable in the first place.
Candor Needs the Missing Puzzle Piece: Vulnerability
Candor alone—“We need 2.5x revenue next year”—can be blunt. But vulnerability asks: Why? “We’re trying to cash out soon,” or, “We promised other stakeholders a big return by year’s end, and we’re feeling the pressure,” or even, “We’re afraid this is our only shot at massive growth.” While that explanation might not be popular, at least they would be forced to admit their motives and people would be armed with the truth.
Yes, some will stay and others may leave, but at least they’ll do so with a clear understanding of the full stakes. Every day team members decide whether to stay at their jobs—whether they realize it or not. By giving them the truth, we enable them to make the best decisions for their own lives. As leaders, we owe our teams that much.
Pirates understood something crucial: A leader who hides behind power eventually finds their crew in quiet revolt. And that applies just as much to investors as it does to CEOs. Without vulnerability, your “team” becomes merely followers who do what they’re told—or they bail. In my Moxy Ox case, the latter happened. As soon as the crew lost trust, they were gone.
A Tale of My Own ‘Mutiny’ Moment
This wasn’t the only time I had to break difficult news or disagree with higher-ups. But the Moxy Ox example stands out because it crystalized a truth: A massive growth push might look great on paper, but if it’s built on hiding the real “why,” it shatters morale when people figure it out. The moment leadership declines to share authentic motivations, we’re on a short path to mutiny—where employees leave, morale tanks, and reputations fall apart.
Lessons from Captains, Past and Present
Spell Out the Loot
Pirates used Articles of Agreement; companies can use open salary tiers or transparent bonus formulas. Show people how decisions get made—and who really benefits.
Elect (or Empower) a Quartermaster
No one should operate without checks. Whether it’s a project manager, a culture champion, or a people ops lead, ensure someone has real power to challenge decisions and keep leadership in honest dialogue.
Context, Not Spin
Reed Hastings at Netflix champions “Context, not control,” meaning leaders share the full picture—budgets, competition, strategy—and trust employees to act responsibly. That’s vulnerability in a high-stakes environment.
Expect Some People to Jump Ship
Radical vulnerability may prompt those who disagree with the company’s direction to leave. Better that than a simmering resentment that poisons the culture.
Start at the Top
If the founder or CEO (or key investors) won’t share their real objectives or concerns, every layer below gets filtered. Employees become cogs rather than a crew that trusts its captain.
From Pirate Ships to the Boardroom: Why It All Matters
At first glance, professional services or cutting-edge tech startups have little in common with ragtag buccaneers. Yet both exist in high-stress environments where fortunes can change quickly and where trust in leadership is paramount. If you want a cohesive, innovative team—rather than a reluctant set of hands who merely follow orders—show them you’re human. Take the risk of revealing how decisions come about, what personal struggles you face, and yes, even your miscalculations or failures.
In a world that too often rewards secrecy and spin, radical vulnerability is the unspoken advantage. It can unify a team around deeper values—much like pirate crews who risked mutiny if the captain strayed from their collective code. You might feel exposed, but as I’ve learned, the alternative is a hollow brand of candor that never quite lands as genuine. True leadership requires showing your belly—sometimes letting the crew see you sweat—and hoping they’ll stand by you because they trust the raw, human honesty behind your words.
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Have your own stories—be they pirate-like, investor-driven, or from modern workplaces—about vulnerability in action? I’d love to hear them. Reach out to discuss how we can steer our respective ships with more authenticity and less fear. After all, we’re all in these choppy waters together, and the best chance for smoother sailing is a crew that trusts its captain completely.
