This story is an excerpt from the book, Stone Soup for a Sustainable World: Life Changing Stories of Young Heroes.

Kassandra Castillo Cruz grew up in what some would call a paradise.  With its 100 beaches, Bioluminescent Bay, warm weather, and cool Caribbean breezes, Vieques is a popular tourist destination off the main island of Puerto Rico.

Isla Nena “Little Girl Island” was also home to 10,000 people, many of whom lived in abject poverty.  When in 1941 the U.S. Navy set up testing for the worst weapons to be used in Vietnam, Afghanistan, Iraq, they suppressed the economy, and encouraged people to leave, or to go on government assistance.  Many left, but others, loyal to their homeland and its people, stayed and managed to eke out a meager living. Kassandra’s mom was hard-working and determined to provide for her family. Every Saturday morning Kassandra and her two younger sisters would jump up on her truck and travel around the island with her, collecting trash. As the eldest child, Kassandra felt a responsibility to set a good example for her sisters. She would always warmly greet her mother’s customers with a big smile as she gracefully gathered up their trash.

Sometimes she found little treasures in the trash. One day she even found a Christian Dior saddlebag. It was almost new, probably left behind by a tourist. For 12-year-old Kassandra, it was a great first handbag.

Thanks to its rich diversity of cultures—from the indigenous Taino with their delicate features, to the descendants of North American, Spanish, and other European colonists, to Cuban and Dominican Republic islanders and the descendants of African slaves—Puerto Rican women are known for their exquisite beauty. They have proudly claimed five titles for Miss Universe, and seven for Miss World. Many of the islanders who watched Kassandra walk down the street on her way to school, with her regal bearing, hoped that one day she would be the one to bring such a title home to Vieques.

On May 1, 2003, when the U.S. Navy finally left the island after 68 years of protesting and civil disobedience, the Island’s people celebrated – there were music and dancing in the streets.  It was Kassandra’s 10th birthday, and she loved the celebratory fireworks that day. Kassandra had loved working with her father to make buttons and T-shirts with messages protesting the Navy occupation of the island. When he died the following year, Kassandra was devastated.  He had instilled in her a longing for a better life; so, she knew that he’d want her to push forward with her dreams.

When she was 14, a friend invited her to join a new youth leadership program, the Vieques Youth Leadership Initiative (VYLI). And when she was asked at the Stone Soup Leadership Institute’s Sustainability Summit, “What is your dream for your life, your island, and your community?” she declared that she wanted to become a top model. Later, in a VYLI video, she said, “I want people to recognize my island for all the positive things here, and for our talented youth, not for the negative statistics; we are too often excluded.”

While she was very shy, Kassandra was even more determined to pursue her dream. She set about finding out what it would take to realize it and signed up for her first beauty contest. To lend their support, VYLI’s loyal band of youth traveled with her to San Juan for the contest.  They marveled as she confidently walked down the runway. And they celebrated enthusiastically with her when she won third prize!

The next year for VYLI’s Job Shadow Day, Kassandra was matched with Ileana Cambó, a former Ms. Puerto Rico and the VP at L’Oréal. That led to her first photo shoot and the beginning of her professional portfolio. At fundraising events, like VYLI’s Taste of the Island, she was introduced to other leaders of the fashion industry. And from there, her modeling career skyrocketed! In just three years, she became a top model for UNICA, the #1 modeling agency in Puerto Rico, and was being featured on fashion magazine covers and receiving many awards. 

However, Kassandra was not naïve; she saw the dark side of the fashion industry, which glorified prepubescent girls and often took advantage of their vulnerability. Wise beyond her years, Kassandra kept her head on her shoulders, and stay focused on her goals. She knew that modeling wasn’t a life for her, just a stepping stone from which to pursue her bigger dreams.

Because she had achieved her first dream, to be a top fashion model, she was an inspiring role model for young girls on Vieques. She led workshops and provided guidance for aspiring models, organized professional photo shoots and fashion shows for them, and led college prep workshops to encourage local youth to strive toward higher education. With VYLI’s Entrepreneurship Initiative, she also led workshops where young people turned local natural resources—seeds, beads, shells, glass, and stone—into unique jewelry. On the weekends, they sold their wares to tourists and raised funds to invest in their initiative. They were thrilled when they were invited to be the youngest representatives at the 3rd Annual Caribbean Artisan Festival in the British Virgin Islands and were able to fly for the first time, to the neighboring island of Tortola, where they met artisans from ten different Caribbean countries, as well as entrepreneurs and re-foresters who were preserving their traditional cultures as well as their island environments.

Kassandra carefully saved the money she was earning from modeling so that one day she would be the first in her family to go to college, an even more important dream come true. At the Inter American University in Puerto Rico, she received her degree in Business Administration. And she spent a semester abroad at the Spain Business School in Barcelona, studying swimwear design at the Centro de Las Artes del Diseño y la Alta Costura. 

In 2012 Kassandra continued to expand her horizons by traveling to Martha’s Vineyard to share her experiences at the Stone Soup Leadership Institute’s Sustainability Summit. And she traveled to the tiny island of Lanai, Hawaii and then the Puerto Rican community of Holyoke in western Massachusetts and to show young people how they could use their entrepreneurial skills to realize their dreams. 

The next year Kassandra moved to Boston and became the first employee for a startup sustainable fashion company Rebag ( In 2014, when the company expanded and moved to the U.S. fashion capitol of New York City, Kassandra moved with them.  Rebag is now a $50 million luxury resale retailer that buys and sells luxury handbags. As its Head of Operations, Kassandra oversees teams of 20 people based in branches all over the world.

Rebag allows customers to refresh their closets as often as they like and choose from a selection of thousands of designer handbags. “You can purchase a bag, carry it for up to six months, exchange it for Rebag credit worth at least 70 percent of the original purchase price, and put the credit toward a new bag,” Kassandra explains. During the COVID pandemic, the company launched a resourceful new app, “Clair AI,” that allows customers to instantly determine the value of new and pre-owned luxury handbags and purchase remotely.  “And you haven’t had to directly interact with anyone to make it happen,” she says.  “We get to give these bags three to five ‘homes’ during their lifetime instead of having them end up in the trash after just one season,” Kassandra says, as she reflects back on the Christian Dior bag she found in the trash as a 12-year-old. “That bag is still very popular,” she says. “And it is worth $3,800!”

Kassandra is proud to be working in the sustainable fashion industry, along with companies like Poshmark and ThredUp. She’s pleased to see that some large companies, like Levi Strauss, are adopting more sustainable practices too, and she keeps a discerning and watchful eye on the way sustainability practices are defined and applied in the industry. 

When in 2017 Hurricane Maria devastated all of Puerto Rico, it brought Vieques to its knees. The island’s famous Bioluminescent Bay was destroyed, along with its rich mangrove ecosystem. Without ferry service, people were without food and gas; and the environmental toxins left behind by the U.S. Navy had left people vulnerable to scary autoimmune illnesses. Without a hospital on the island, many people died, especially the elderly—including Kassandra’s beloved abuela. Kassandra did what she could to help her family, raising funds and sending them to her mother, and offering her sisters and their children shelter in her tiny Manhattan apartment.

But people on Vieques are survivors, and they are resilient. They have rallied, and together they are slowly rebuilding their island.

During the pandemic, Kassandra has continued to work with Rebag remotely, which gave her the chance to return to her homeland so her new son, Thiago, could spend time with her family. She loves seeing that the spirit of Vieques is still strong. She’s especially inspired by how young people are leading the way with organizations like La Coleman Cimarrone, creating community gardens and big composting and recycling projects, as well as ecotourism companies that offer hiking and other island adventures. “It’s refreshing,” she says. She’s glad to see that people on Vieques are striving to become more self-sufficient by growing their own foods and creating renewable energy projects. And she’s especially glad to see that they are working together to improve life for everyone on the island. When she returns to her life in the Big Apple, she hopes that one day she can live part-time on Vieques so her children can appreciate its beauty and its community spirit.

Ever the entrepreneur, Kassandra may one day even create her own company, and the chance to make new dreams for her life—and her community—come true.

The only limit to the height of your achievements is the reach of your dreams
and your willingness to work for them.
Michelle Obama

Call to Action: Invest in young people to realize their dreams. Vieques Youth Leadership Initiative: Check out Kassandra’s company on IG: kavani_handmade.