People of St. Pete: Hunter R. Thompson

St. Pete is celebrated for its fabulous weather, beautiful vistas, world-class food scene, and thriving cultural atmosphere, but the people of St. Pete truly make this city something special. In appreciation, each month Green Bench shines a light on one of the many people that make St. Pete unique.

This month we are putting the spotlight on Hunter R. Thompson, co-founder and chief operations officer of SailFuture. With its home base in St. Pete, SailFuture changes the lives of young people and their families with its innovative programs, including an entrepreneurial career-prep, tuition-free high school, residential homes for kids in the foster-care system, experience-based mental health counseling services, international sailing expeditions, and hands-on, behind-the-scenes job training. Thompson is passionate about providing teens positive opportunities to disrupt potentially destructive social and economic cycles.   

Planting the Seeds

As the son of a college administrator and an artist, his current path may seem to have been a natural one, but nothing in Thompson’s youth pointed to a future as an educational innovator. A bright kid and indifferent student and troublemaker, he barely made it through high school. Hoping to shift his perspective and disconnect him from bad influences, his parents urged him to take on a volunteer opportunity with the Meno A Kwena: Water for Life project. They got their wish. After spending four months in Botswana volunteering and helping locals “develop skills for income and economic empowerment,” Thompson’s perspective shifted. He liked being part of something that made an impact and “added value” to the world. He still wasn’t sure where that understanding would lead him, but, with hindsight, he knows that this experience “planted the seeds” for where he is today. Still unsure how those seeds would sprout, Thompson began college at the Ringling School of Art & Design in Sarasota in 2010. His years at Ringling changed his life, but not in ways that were entirely expected.  

Designing A Future 

After earning his Bachelor of Fine Arts degree in 2014, he went to work as a creative director, developer, and designer. Successful, but unfulfilled by the world of retail advertising, Thompson jumped in with both feet when Mike Long, a college friend, reached out. The two had bonded as captains of their respective flag-football teams. They also shared a sense of adventure and the desire to make some sort of difference in the world. After his own experience in the juvenile-justice system, Long dreamed of creating a program where sailing expeditions could be offered to some young offenders as a viable alternative to incarceration. Wanting to be part of this ambitious idea, Thompson quit his job. The two embarked on renovating a donated 65-foot yacht and raising money. In 2015, 10 young-adult offenders joined the two on “Defy the Odds” for a three-month sail. Not satisfied with the lasting impact of this short expedition, they opened the first of two ongoing group homes for teenage boys in the foster-care system. Homeschooling their foster kids soon blossomed into a plan for an accredited high school. In 2020, SailFuture Academy opened as an innovative, project-based high school in the former Norwood Elementary School on 27th Avenue N. Sailing is still central to their mission to “transform life outcomes,” but Thompson and the rest of the SailFuture team have created a space where previously disengaged students can thrive in a variety of real-world scenarios. As he explained, the course of SailFuture is still being charted. To learn more, visit www.sailfuture.org    

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Tina Stewart Brakebill
Tina and her husband Brian visited St Pete for the first time in January of 2017. Four months later, they waved goodbye to Illinois and moved to their new forever home in the Sunshine City! They both believe it’s the best snap decision they ever made. Leaving her job as a university history professor was the toughest part of the relocation, but she is thoroughly enjoying having more time to write. Currently, in addition to her work with Green Bench Monthly, she is working on her third book (and first novel) and loving life in DTSP.