How 1,000 Failures Helped this Deep Sea Team Succeed

Rob McCallum holding what was a normal-size cup prior to the pressure from going to the bottom of the ocean. Photo by Reeve Jolliffe.

When smoke filled the manned submersible cabin of Limiting Factor at 5,000 meters beneath the surface, few would call it a “win.” But when every member of the Five Deeps Expedition team engaged as planned in just 10 seconds, expedition leader Rob McCallum knew that their ambitious goals were within reach.

The Five Deeps Expedition was the brainchild of extreme explorer Victor Vescovo. In 2017, Vescovo became the 12th American to complete the ‘Explorers Grand Slam’ which requires climbing the highest peak on all seven of the world’s continents including Mt. Everest, and skiing at least 100 kilometers to both the North and South Poles. Of course, he didn’t stop there. What if he could become the first person in history to have been to the top of all the world’s continents as well as the bottom of each of its oceans? What would it take?

For a project that involved prototyping a brand-new submarine, refitting a ship for deep-sea exploration, and uniting six teams who had never worked together before, the Five Deeps team knew risk wasn’t something to avoid. It was something to engineer for. With so much to overcome from the very start, by the time the team reached early sea trials, they already felt pushed to the edge.

In such extreme conditions, it’s especially easy for frustration to ruin an operation. But instead of collapse, Rob, as the expedition leader, sparked a cultural reset.

"There may be 1,000 failures between us and success,” he told the team. “Today, we knocked off 12."

This wasn’t just spin. It was leadership psychology at its best. By reframing the experience, Rob normalized failure, rebranded it as progress, and celebrated transparency. The team went from demoralized to energized. Engineers, deckhands, scientists, and cooks alike leaned in.

“If you can transform a failure into a lesson, it then becomes a building block in the foundation of your eventual success,” Rob told me.

He smiled wide remembering team members in meetings from then on. "We had six failures today!" they’d say. Any frustration or shame they once felt had been replaced by sheer perseverance.

And by the end of the mission, they had accomplished the unthinkable: diving to the deepest points in every ocean and racking a slew of world records.

The Audacity of Purposeful Risk

The Five Deeps Expedition was daring, but equally calculated, engineered, and relentlessly tested. The journey included 47,000 nautical miles, dives in both polar regions, and visits to the bottom of trenches that had never been reached before. It even included a series of dives on the Titanic.

Risk-taking in this context wasn't an adrenaline play. It was strategy. It was discipline. And it’s a mindset that every leader should understand: bold vision only becomes innovation when it’s coupled with methodical execution.

Bold Moves vs. Reckless Risks

What sets Rob and leaders like him apart isn’t bravado or blind ambition. It’s what he calls the discipline of boldness. He knows that bold missions aren’t defined by headline-grabbing risks, but by their underlying structure.

"You can’t drive to the shop without taking a risk," he says. "But you make sure the driver has a license, the car has brakes, and everyone’s wearing seatbelts."

The sea trials were a masterclass in this mindset. The team wasn’t chasing heroism; they were building a system to fail safely. Each failure was isolated, analyzed, and corrected. Experts on every single aspect of the operation were brought in to mitigate bias. New SOPs were written. Equipment was redesigned. Team members were trained, and trained again.

A Culture Where It's Safe to Speak Up

Key to the team’s approach: there was no finger-pointing. No shaming. Instead, Rob made it okay to walk into a meeting and say, "I messed up."

When someone admitted a mistake, the group would gather around. "What do you think happened?" they'd ask. "How can we fix it?" It created a remarkable esprit de corps built not from success, but from shared struggle. That camaraderie and deep trust, born of open dialogue and problem-solving, became a competitive advantage.

This kind of cultural transparency helped the team thrive not only technically, but emotionally. It’s easy to underestimate just how hard it is to build resilient human systems for extreme environments. Rob’s commitment to psychological safety, honest feedback, and continuous learning made it the standard.

So, how does one begin to create this kind of culture?

“Ditch the ego,” Rob says.

Everyone is Mission-Critical

Five Deeps crew. Photo by Mike Moore.

Whether you were piloting the submersible or prepping laundry for the next dive, you were mission-critical. Rob set this tone by making a point to acknowledge someone’s contribution in daily meetings.

“Thanks to the galley team for having a meal ready, even after a late and exhausting dive.”
“Thanks to the laundry crew for prepping the flight suits—they looked great in the documentary shots.”
“Chief Engineer, thanks for making sure the hydraulic systems are running smoothly.”

It wasn’t forced or over-the-top—it was just part of their conversations. No high-fives or back-slapping, just honest recognition of effort. That way, it never felt like favoritism, just a natural acknowledgment of teamwork.

"The laundry guy never said a word in the meetings," Rob said. "But he was as essential as the chief sub pilot. All of us had a role to play; we could only survive as a team."

The result? A high-trust, low-ego, high-performance culture where people showed up with pride, spoke honestly, and took ownership. It wasn't about performative team-building. It was about consistent acknowledgment, day after day, of each person’s role in the mission's success.

Make It Real:

• Set the expectation that things will break early and often in your startup—especially if you're building something new.

• Celebrate learnings, not just wins. Dedicate part of your all-hands meetings to "failures of the week" and what was learned.

• Make it safe to speak up. Create rituals that normalize transparency and reward self-reporting.

• Frame failure as a data point. If you're trying something ambitious, anticipate failure as a stage of progress, not a deviation from it.

• Practice failure drills. In the same way an expedition prepares for emergencies, run through what happens if your website crashes, your top hire quits, or your funding stalls.

• Develop layered contingencies. Like the Limiting Factor’s ballast systems, create business redundancies that allow recovery even in worst-case scenarios.

• Commit fully once the risk is taken. Decisiveness and clarity fuel follow-through. Once your course is set, bring your team into full alignment.

For Your Journey

If your team is afraid to fail, they’ll hide mistakes, minimize risk-taking, and stall innovation. But if they know failure is expected, accepted, and even celebrated when handled well, they’ll experiment with more confidence, and learn faster.

Rob’s greatest leadership move wasn’t leading a dive to 10,000 meters. It was turning fear and frustration into fuel for progress.

"It’s only a failure if you don’t learn from it," he says. In high-stakes expeditions and your own business endeavors, the principle is the same: you either fail forward, or you fail for good.

Special thanks to Rob McCallum and EYOS Expeditions for these insights and so many more.