Tech entrepreneur Tristan Schukraft, known for his string of successful ventures, has made a bold move into the world of hospitality by acquiring a significant portion of Fire Island’s Pines district. The $17 million deal, announced in May 2024, includes the purchase of key venues such as a hotel, nightclub, restaurant, and the iconic Blue Whale bar, a central hub of the island’s gay community.
Schukraft, who has lived in Los Angeles and Puerto Rico, was initially hesitant to visit Fire Island 12 years ago, despite the island’s reputation as a sought-after gay vacation destination. He was invited by friends to stay in the Pines, a secluded area of the island known for its lack of cars and welcoming environment for LGBTQ+ individuals.
In an article with The Wall Street Journal, Schukraft said “My friend hit me up and said, ‘You should come to Fire Island—you can sleep on the sofa,’” Schukraft recalled. “I was like, ‘That’s not really my thing.’” But after borrowing money for the ferry ride and experiencing the island for himself, Schukraft was hooked. “I ended up loving it,” he said, describing the rustic charm and unique atmosphere of the destination.
Despite his early fondness for Fire Island, Schukraft visited only once more in the following decade. It wasn’t until 2024 that he decided to invest in the island’s storied history, purchasing the majority of the Pines’ commercial district. His acquisition is part of a broader effort to preserve gay cultural landmarks, which includes the $45 million purchase of the Abbey Food & Bar in West Hollywood, an iconic gay bar that had recently been plagued by allegations of drug-related incidents.
Schukraft’s push to revitalize historic LGBTQ+ spaces extends beyond West Hollywood. He is also reopening the legendary nightclub Circo in Puerto Rico and purchasing the D.S. Tequila Co. nightclub in Chicago’s Boystown neighborhood.
While Schukraft has earned praise for his vision, his plans for Fire Island’s Pines district have sparked skepticism from some community members. Fire Island, particularly the Pines and nearby Cherry Grove, holds deep cultural significance for the LGBTQ+ community, having long provided a refuge for gay individuals. It is home to the famous “tea dance” party, which was founded in the 1960s, and other cherished traditions like the annual Fourth of July drag queen “Invasion.”
A tea dance at the Blue Whale, 1981. Credit: Fire Island Pines Historical Society
“We have a very opinionated, critical community who all have something to say,” said Bobby Bonanno, founder of the Fire Island Pines Historical Society. Bonanno emphasized that Fire Island’s significance has only grown in the current political climate, where LGBTQ+ rights are under constant threat.
Despite the pushback, Schukraft remains confident in his ability to breathe new life into the Pines. “I think we’re going to bring a breath of fresh air into Fire Island—I think people are really going to like it,” he said. Schukraft’s confidence stems from his track record of overcoming challenges in business, a skill he attributes to his sales background.
However, Schukraft’s lack of experience in the hospitality industry has raised questions about his ability to successfully manage such a high-profile project. As the founder of tech companies like the HIV telemedicine platform Mistr and the e-ticketing company ID90.com, Schukraft is taking a bold step into hotel and nightlife ownership with plans for an outpost of Tryst Hotels in the Pines. The hotel is set to be the first luxury gay hotel brand, with other locations opening in Puerto Vallarta, Mexico, and San Juan, Puerto Rico.
In Puerto Vallarta, Schukraft has already made waves with the opening of the Tryst hotel, which has quickly become a hotspot for the local LGBTQ+ community. “On Sunday, I’m even more exhausted from partying all weekend,” Schukraft admitted, reflecting on his work-hard, play-hard lifestyle.
While his luxurious lifestyle may seem at odds with the laid-back vibe that Fire Island is known for, Schukraft is determined to leave his mark on the island and the larger LGBTQ+ community. “There are gays that want the five-star experience where they can be true and authentic to themselves,” he said. “Why do we have to settle for a four-star?”
Schukraft’s dedication to the project extends beyond business interests. He acknowledges the challenges of Fire Island’s remote location, noting that building on the island can be difficult and expensive. “It’s a very punishing environment,” said Andrew Kirtzman, a former owner of the Pines commercial district.
Even with his financial commitment, Schukraft is realistic about the potential for profitability. He openly admits that his investments in LGBTQ+ spaces, including the Pines, are more about preserving a legacy than maximizing profit. “Serving the gay community is a passion project,” he said. “At the end of the day, my name is on it.”
As Fire Island’s Pines district undergoes renovations, Schukraft is working to preserve its history while modernizing the area. One of his first changes is rebranding the district, which he says currently sounds too “boring” and impersonal. “We’re going to rename it ‘the Waterfront,’” he revealed.
For Schukraft, the journey to preserve Fire Island’s cultural legacy is just beginning. Whether or not his investment pays off financially, he is focused on securing the future of iconic gay institutions, ensuring they remain vibrant and relevant for generations to come.
