The mast began to pitch towards the water at a harsh 45-degree angle. The wind blew rain horizontally against the sailors, and for the first time, they had to balance pulling the boat’s cables with wiping their faces off. The sailboat had never moved this fast, and everybody suddenly was familiar with the physics behind how wind turns into speed.

Dillon Hale, the instructor, laughed a bit to himself and reminded students that “as much as it feels like it, the boat won’t tip over. You’ll only fall into the water if you try to.”

However, these were not sailing athletes or physics students; they were four business students far outside their comfort zones. They got on the Wired about an hour earlier, and only one had sailing experience.

As quickly as the storm started, it ended. The wind slowed in the opposite direction, and the rain turned into a light mist, but they weren’t allowed to cheer quite yet. The sail at the front of the boat began to flap wildly, and the boat slowed.

Malek DeBrabander, W’25, yelled, “I’m ready to switch directions!”

Rachel Doman, W’26, and Abu Mcunu, W’25, with the confidence of experienced sailors, yelled in response, “Ready to tack!”

Abu, on the left side, let go of the taut cable. Rachel, on the right side, began pulling furiously until the cable tightened and locked it into place. The boat satisfyingly tilted and picked up speed, and for a second, it felt like the boat was flying.

The waves grew larger, and everybody on the boat groaned. They weren’t ready for another storm, but Dillon said the opposite was occurring.

“Waves are just a history of the wind.”

The Road to Adventure

On a Friday at 6 am, seeing a coach bus waiting outside Huntsman Hall on Penn’s campus is not surprising.  The usual guess is that students are going to New York or DC with their clubs for career treks.

Wharton Leadership Ventures (WLV) often uses them to take students to unusual locations, such as rural Pennsylvania or upstate New York for daylong “intensives” like high-ropes courses or mountain biking. WLV also flies students to locales like Cotopaxi in Ecuador or Patagonia for week-long hiking and backpacking Expeditions over winter and spring breaks.

“We’re doing things in a completely new environment,” said Erica Montemayor, Senior Associate Director of WLV. “What students take most from this experience is just getting out of their comfort zone.”

Venture experiences are coordinated and overseen by Wharton undergrads known as Venture Fellows. A fellow was on every boat during this intensive, helping facilitate acclimation and reflection during and after the sailing experience.

Kai Mai, a fellow on his fourth sailing venture, explains: “You learn how to lead a wide range of students and see their leadership styles, and by the end, you walk away with an expanded skill set.”

Learning to lead as a venture fellow features standards like speaker events and communication training but also has unorthodox aspects.

“We do hands-on outdoor learning during fall and spring training, and then we divvy ourselves up and lead these intensives and expeditions,” Kai said. “We actually have mountain guides do some of our trainings.”

The Practice Run

The role of the venture fellow becomes clearer when watching Malek lead different groups during the intensive. At the start of the day, he takes attendance and ensures everybody gets their food. Once the bus arrives in Annapolis and everybody wakes up from their morning naps, he leads the group through an icebreaker.

Once the ice was broken, the groups were ready to sail. The first part of the day would consist of learning how to sail, and the second part would culminate in an obstacle course similar to regular sailing competitions, where each group would have to organize themselves into a pre-set formation and go around the course five times in a time trial.

The rain picked up as everybody boarded their boats for the practice run. On the Wired, instructor Dillon taught the group the vocabulary of a sailboat. To turn, the front sail had to match the direction of the wind, or in sailing terms, people on port and starboard needed to “tack” or “trim the jib” to match the movement of the wind.

The practice run featured leadership struggles, uncoordinated tacks, and Dillon’s intervention to keep the boat moving. As the rain picked up and slowed down, everybody settled into their roles after being forced to adapt to hard conditions.

After lunch, the instructors explained the next step of the intensive. They flipped over the whiteboard to showcase a colorful illustration of boats moving between cones. At the start of each time trial, the finish line order would be listed, and they would time the speed it took the boats to cross the finish line. They gave each boat a walkie-talkie, and the instructors took a step back – it was time for the students to lead each other.

As the rain picked up and each boat moved to the start of the course, each team began practicing using the walkie-talkies.

“Can somebody tell a joke right now?”

Another team chimed in: “We’re not going to do well at this.”

The time trial’s structure meant that each team was working to compete against their previous performance. As each round continued, the boats got more efficient at moving into the proper formation at the finish line and presented faster times. By the final round, the last boat crossed the finish line in ten minutes. Everybody cheered as the time was announced through the walkie-talkies.

Reflecting on the Race

The way WLV teaches leadership is separate and entirely connected to the in-class business education.

Malek, the fellow on the Wired, explains that venture fellows “go to expert talks of organizational psychologists and learn what the best techniques are for leadership,” which is reminiscent of the leadership techniques taught in courses like Management 3010.

WLV heavily emphasizes the value of reflection and transference, ensuring that the experience’s lessons are brought into real-world business and leadership contexts. While organizational psychologists can help guide the theories behind leadership, a key theme of the ventures is that leadership is also built in unorthodox environments and contexts and that organizational success is not only present in the workspace.

“We’ve adopted after-action reviews from the military where we go back and reflect and recap these moments,” Kai, another fellow said.  “Whenever I do something new, and I make a mistake here or there, I’m able to adapt these AAR techniques into my life.”

Kai then quickly runs through an example of his reflection process.

“Am I communicating this thing well? Or should I try to think about this in a different way? Or what is that other guy thinking?” Kai asked. “There are so many factors at play that AAR has allowed me to pinpoint and focus on that present moment.”

y utilizing different reflection and learning processes, venture fellows have been able to think about leadership in nontraditional, nuanced ways. The best part is that they can bring these processes to the participants, as seen by the Wired boat’s after-action review (AAR).

Rachel, the third-year student on the Wired, reflected: “There was a lot of new terminology and figuring out what worked, but once we got in sync with the jib, it was very rewarding to work well as a team and watch everybody else come into their roles.”

The corollary here is readily apparent – college students are often put in unfamiliar, jargon-heavy internships or courses where they have no option but to adapt to the language and culture of their new environment. While different, sailing is another example of how teamwork can make it easier to gain these necessary skills.

The goal of the sailing intensive was to gather a group of strangers, put them into an unfamiliar context, and derive success from the entire team’s ability to adapt to new circumstances. It was even satisfying to come in last place.

“There’s something kind of metaphorical about the fact that we had to be last in order to make sure that everyone else was able to succeed,” Abu, W’25, said. “Accomplishing that goal was a great moment because we all figured it out together.”

Erica agrees. “It’s complete chaos, but it’s interesting to see what you’ve learned, apply it, and move quickly,” she said. “Because life is always going to move, and it’s either going to move you or you’re going to respond to it.”

After the AARs, everybody thanked their instructors, and the sun peeked out of the clouds and began shining brightly. The Chesapeake Bay began to shimmer, rays reflecting off the water and twinkling against the boats. The whole group groaned, and everybody started to complain about how they had to sail in the unforgiving rain just a few hours earlier.

When walking towards the bus, laughter and chatter filled the air as everyone talked freely, arms slung around the shoulders of their old crewmates and new friends. As the wind blew through the narrow streets, the conversations got louder, and the group turned into one big wave of sound.

—Alex Zhou, C’25, W’25

Posted: December 13, 2024