Finding Purpose Across Cultures

By Kara McDuffee

At a recent All-School meeting, Sims and James shared how their Brewster experience planted the seeds for a life-changing nonprofit—and a deeper purpose.

When Josh Sims ’04 and Tyler “Deion” James ’04 returned to Brewster to speak at a recent All-School meeting, they weren’t just visiting familiar grounds. They were returning to the place where the first seeds of their life’s work–and purpose–were planted.

Today, Sims and James lead The Culture Connection Project (CCP), a nonprofit that builds appreciation across diverse cultures through immersive experiences in Uganda and beyond. Their tagline is simple but profound: “Get connected, not influenced.” Their work empowers people from all backgrounds to learn from one another authentically, without imposing or changing the communities they meet.

But the story began years ago, here at Brewster.

Brewster Beginnings

As a teenager, Sims didn’t expect to find meaning in the Brewster experience. “I came to Brewster a bit of a rebellious kid. I was just going to ‘do my time’ here," he said.

The arts-focused student practiced his creativity in and out of the classroom, but it was the lesson that he could make an impact that changed him the most. “One transformative moment for me was starting a club—The Hunter and Sims Club—and inviting the whole school to join. Everybody did, including faculty and staff. We raised $3,000 at one event, which we used to build a house in Haiti,” Josh recounted. “That was the first time in my life that I realized I could do things that could change the world."

After Brewster, Sims earned a Bachelor’s degree in Graphic Design at Maryland Institute College of Art (MICA), and then entered the digital advertising and tech world. He quickly found success, receiving the Boston Business Journal’s prestigious recognition for “40 under 40” in 2016. However, he told students, “To be honest, I still wasn’t happy. I felt I was lacking some type of purpose. I kept my head down and I kept grinding, but I was really thinking ‘Is this what I’m going to be doing forever?’”

Meanwhile, for James, his early focus was clear: basketball. “I came to Brewster as a junior with one focus—basketball—and getting a Division 1 scholarship,” he shared. He recounted to the student body how much work he put in at Brewster to make this vision a reality, with the intention of entering the NBA after college. Everything seemed to be going according to plan… until a bad knee injury ended his basketball career, sending him back to his hometown of Milwaukee–the one place he never intended to return.

“I left Brewster, I left Milwaukee, I left all of this, and now I’m right back there. How did this happen?” he recounted. He shared with students how depressed he felt, which was only amplified by his mother’s death. During this lost period, he decided to fly back to Wolfeboro for his ten-year reunion.

Who would guess that a Brewster reunion would be the turning point for both men?

A Life-Changing Journey

Sims and James reconnected in 2014 at their ten-year Brewster reunion, and then again at Reunion two years later. They realized they were both searching for deeper fulfillment. Sims, who had traveled to Uganda a few times after a family trip there, invited James to join him.

The trip to Uganda was a revelation. James, who had grown up in one of Milwaukee’s toughest neighborhoods, described being humbled by the resilience and joy of communities facing far greater challenges.

“Instantly, the light bulb went off,” he explained to the Brewster students. "How was I looking at everything I didn’t have and not appreciating what I did have? I got back December 14, 2016, and my life ain’t been the same since.”

For Sims, seeing James connect so powerfully with the people he met helped spark a bigger vision–one that had been front of mind every time he traveled to Uganda. They realized that the heart of their work wasn’t charity—it was connection. It was about mutual appreciation, not influence or aid.

In 2018, they officially launched The Culture Connection Project, bringing groups of participants of all ages, from 13 to 86 years old, to Uganda to learn, share, and build relationships.

Sims and James shared with students the journey of CCP and how it grew, transforming over the years from an exciting idea to a nonprofit organization, changing people’s perceptions and lives with every trip. The CCP has grown so much that Sims decided to leave the tech world and focus solely on their organization. Today, their model is expanding into India and other parts of the world.

Bridges Are Being Built at Brewster

Throughout their All-School presentation, Sims and James kept returning to Brewster’s role in shaping who they are.

"In both our minds," Sims said, "Brewster was the first Culture Connection Project."

James echoed the sentiment. He talked about how many fellow students he met at Brewster with different backgrounds, interests, and sports, but how everyone connected in the same role: being a Brewster student.

“Brewster set the foundation for the Culture Connection Project,” James said. He advised the current students: “Just being in these kinds of experiences with different people, it may make you open to new things in different environments. That's what culture connection is all about.”