Ep.3: No Plan B - Sailing Off the Map and Into the Unknown

The great explorers of the past didn’t set sail with a backup plan—they left behind familiarity, navigated uncharted waters, and risked everything without assurance of return. Their success wasn’t guaranteed, but their boldness created new worlds. Leadership and entrepreneurship are no different. When you commit to something fully, without a safety net, you force yourself to adapt, lead, and grow.

“We were about to do something that had never been done before. There was no playbook. We had to write it as we went.”– David Marquet,?Turn the Ship Around!

This chapter is about making that leap, about saying yes when every instinct tells you to hesitate, and about building something from nothing with no option to turn back.

Moving to a new country while simultaneously building a company was the ultimate test of this principle. The rhythms of business and family life had to sync, even as both evolved in real-time. For me, establishing a team in Canada was about fostering an environment where trust and responsibility flourished.

The Defining Moment: A Risky Offer

Imagine this: you receive an offer five times larger than the investment you anticipated at the pre-seed stage. It sounds like an entrepreneur’s ultimate dream—ample fuel for scaling, the ability to hire top talent, and the capital needed to make a lasting impact.

But there’s a catch. The investors have two non-negotiable conditions: relocate to the go-to-market (G2M) location immediately and deliver a fully developed product—not just a proof of concept—within 18 months. No gradual transition, no dipping a toe in first—just pack your bags, uproot your life, and dive in headfirst. Would you take the deal?

This was the exact crossroads I found myself at. The potential upside was enormous, but the risk was equally daunting. The decision wasn’t just about business; it was about my family, the few individuals who had already joined my journey, and the foundation of everything I was trying to build.

Saying "yes" meant immediate execution—establishing a team, a company, in an unfamiliar market while ensuring we are on solid ground.

Actionable Insight:?Every major decision is a trade-off between security and possibility. The question isn’t just what you stand to gain, but what you are willing to lose. Clarity comes not from avoiding uncertainty, but from recognizing which uncertainties you’re willing to embrace.

The Early Days: Setting the Foundation

I arrived in Canada with a mission and zero familiarity with the local banking system. My first stop was the financial district, where I walked into a bank, ready to open accounts for both myself and my new company.

It might sound straightforward, but at 27, my only knowledge of businesses and banking came from academic theory, not real-world experience.

Approaching the first banker I saw, I confidently explained what I needed. When he realized I was an immigrant with no local credit history and a brand-new business, his polite but subtly dismissive tone set in: "It will take at least a month."

With an approach I learned when I was nine years old, joining my father to buy vegetables at the city market—being sent loose to get attention from savvy market sellers shouting at their audience from a meter above my head—I walked into the bank, ready to make my case. I wasn’t about to take no for an answer. Maintaining a calm but assertive demeanor, I leaned in slightly and said, "That’s unfortunate—because I’m sure the bank across the street would be happy to work with a fast-growing company like mine." The banker’s expression flickered—hesitation, realization, then urgency. He excused himself, and minutes later returned with the branch manager. By the end of the week, I had both accounts fully set up, proving once again that persistence, confidence, and a strategic push can turn an initial 'no' into a resounding 'yes.'

This experience reinforced a valuable lesson—bureaucracy thrives on resistance to change, but confidence, persistence, and the ability to challenge the first "no" can often unlock doors that seemed closed.

Actionable Insight:?The foundation of any venture is built on the ability to adapt without losing structure. Processes should serve as guiding instruments, not rigid constraints. Whether setting up a business or navigating unfamiliar territory, clarity and persistence in execution determine success.

Similarly, hiring the first team members required balancing skill, cultural fit, and trust. Canada’s diverse population allowed me to build a team with a wide range of backgrounds from day one, creating a culture where each individual’s unique expertise and experience strengthened the whole. But diversity alone wasn’t enough—it had to be transformed into a cohesive unit where different perspectives fused into shared innovation.

In today’s overly sensitive culture, where asking about age, background, or anything too personal is off-limits, I had to find a different way to ensure I was hiring the right people. I moved beyond conventional interviews. Instead, I placed candidates in unfamiliar scenarios, nudging them slightly outside their comfort zones to observe their adaptability and problem-solving skills. Whether tackling an unexpected challenge or solving something with no pre-existing formula, these moments revealed how they would perform when reaching uncharted territory. If tech companies are about building what has never existed before, we pushed that idea even further—assessing how people thrived in an environment where certainty was a luxury.

Turning the Ship Around

David Marquet’s experience transforming the USS Santa Fe from one of the worst-performing submarines into one of the best is a perfect example of what leadership under pressure really means. He didn’t micromanage or issue more orders; instead, he gave control and ownership to his team, forcing them to rise to the occasion.?

That same principle applied when SkyX faced its first major setbacks. When we crashed our airplane for the first time, the team was crushed. They weren’t just worried about letting me down—they felt they had failed themselves. The weight of the setback was palpable, and with it came the realization that we were now significantly behind schedule.

Instead of tearing apart the failure in the heat of the moment, I told them to document only the facts—no interpretations, no conclusions. I wanted us to capture the raw memory before it faded, free from overanalysis. Then, I sent them home early with one simple instruction: relax, clear your minds, and come back tomorrow ready to build it better. We would debrief in the morning, not to dwell on the crash, but to focus on making the next iteration stronger.

This approach mirrored David Marquet’s philosophy in?Turn the Ship Around!, where he recognized that empowering his crew to solve problems—rather than dictating every move—created a more resilient, accountable team. Just like his sailors, my engineers needed space to process failure and return with the clarity to innovate. By shifting the mindset from failure to iteration, we ensured that our next aircraft wasn’t just a rebuild—it was a breakthrough.

Moving from a flight squadron—where the commander is expected to be the most skilled pilot—to a tech organization, where my tech lead had to surpass me in engineering expertise and my finance lead had to be sharper with budgets, was a profound shift. In a squadron, leadership is built on mastery; in a company, it’s built on enabling others to master their own domains. This transition required me to embrace a different kind of leadership—one where my role was to create the conditions for others to thrive rather than being the most capable individual in the room.

At times, I even joked that the best thing I could do at the test site was to make coffee for the team—and I meant it. My job was no longer to be the best at everything but to remove obstacles, provide direction, and ensure they had everything they needed to succeed. True leadership is not about being indispensable; it’s about making yourself unnecessary in the best way possible.?

Actionable Insight:?True leadership isn’t about knowing all the answers—it’s about creating an environment where your team is empowered to find them. Like Marquet’s crew on the USS Santa Fe, when people take ownership, they move beyond compliance to commitment, ensuring long-term success in both business and life.

Thrown into the Deep End—And Learning to Swim

David Marquet’s?emphasized decentralizing command and empowering people to lead. At SkyX, I knew that a top-down approach wouldn’t cut it. My team needed to operate with autonomy, make decisions with conviction, and take ownership of their work. But fostering a culture of trust wasn’t just a professional mission—it became deeply personal as my family navigated a whole new world.

While I was focused on ensuring my team could handle the relentless pace of a fast-moving startup, I was also leading a very different mission at home—helping my children navigate the realities of being newcomers in a foreign land. The move to Canada wasn’t just about my career; it was a complete shift in their world. New customs, a language they hadn’t yet mastered, and a climate that made stepping outside feel like an arctic expedition—it was overwhelming in ways that couldn’t be prepared for in advance.

They faced an entirely different school system, trying to decode unfamiliar social cues while making sense of subjects in a language they were still adjusting to. But just like in business, where challenges aren’t roadblocks but stepping stones, I wanted them to see this transition as an opportunity to grow stronger rather than something to fear.

"This isn’t hard because you’re bad at it," I used to tell them. "It’s hard because it’s hard, and every time you push through something unfamiliar, you’re becoming stronger, smarter, and more capable."

Discomfort is temporary, and with time, they found their rhythm. They made friends, tackled schoolwork in English, and even laughed at how absurd it felt to pile on layers of clothing just to walk outside. What seemed impossible at first was just the early stage of something they would later own with confidence.

One of my daughters came home defeated after her first day of school—overwhelmed by a sea of unfamiliar faces, feeling like an outsider, unsure how to break through. I could see the frustration bubbling beneath the surface, the quiet doubt taking hold. That night, instead of rushing in with advice, I sat her down and shared my own moment of feeling utterly lost.

I told her about my first trip to a Tim Hortons drive-thru, where I confidently pulled up and, eager to blend in, ordered a 'coffee with cream and sugar.' The cashier paused and asked, 'Do you mean a double-double?' Not knowing the term yet, I hesitated and said no, only to find out later that was exactly what I wanted.

I had overcomplicated the most straightforward order, holding up the line while the cashier patiently waited for me to figure it out. At that moment, I felt like an outsider, painfully aware of how something so small could highlight how new I was to this place. But then, I laughed at myself, took my coffee, and moved on. The next time? I rolled up and ordered a double-double with confidence, and no one would have guessed I was still figuring things out.

"Struggling doesn’t mean you’re failing," I told her. "It means you’re learning. And soon, what feels impossible today will be second nature." Seeing her shoulders relax, I knew she got it. She wasn’t just facing a challenge—she was stepping into something new, something she would eventually own with confidence.

Actionable Insight:?Resilience isn’t just about enduring challenges—it’s about embracing them with curiosity. Whether in business or family, stepping into discomfort with a willingness to learn transforms obstacles into stepping stones. The goal isn’t to avoid mistakes but to see them as part of the journey to mastery.

Breaking new ground—both in business and family—isn’t just about survival. It’s about creating something meaningful that lasts. Looking back, the challenges of those early days weren’t obstacles; they were the foundation of everything that followed.

Remember, It's Your Path - Pilot It.