The founders behind Bumble Expeditions turned an outsider mindset into a vertically integrated tourism company built around community, creativity, and people who never quite fit the mold.
Every year, Cole Dembs and Sara Hadad-Dembs celebrate what they jokingly call their Spam-I-versary, a reminder of the two months they survived on canned meat after arriving in Alaska with just $250. Today, they own a private island and have built one of Alaska’s most distinctive tourism companies. They’ve built it around a simple belief: some of the best businesses are built by people who refuse to follow the expected path.
From a tent on a ferry deck to a four-acre Alaskan island, a café, guided land-and-sea excursions, and cruise-industry partnerships, their story is less about luck than what becomes possible when people stop waiting for permission.
The $250 Leap
Cole and Sara sold nearly everything they owned in 2015 and drove north. The journey to Sitka, Alaska, was not a safe, calculated relocation. They cooked over a fire the whole way. On the ferry, they slept without a cabin because a cabin cost more than they had to spare.
Sara had a job offer as an educator waiting. Cole took whatever work he could find: delivering newspapers, substituting in classrooms, driving a tour bus, and eventually landing a job at a silver mine. The first paycheck was still two months away. Spam became the unofficial mascot of those early weeks, but so did the generosity of the Haines community. Neighbors invited them to dinner more times than they could count, and those meals helped carry them through until that first paycheck finally arrived.
“We are truly living the Alaskan dream of ingenuity, hard work, and perseverance,” Sara has said, words that take on a different meaning once the full picture comes into view.
The story becomes even more compelling when you understand where each of them started. Sara grew up inside an entrepreneurial family whose business roots in southern Colorado stretched back over 110 years, with retail stores built by her parents and grandparents across generations. As a woman in that family, however, the path offered a bookkeeping job rather than leadership. She watched her father run things from the sidelines. She absorbed every detail. Then she left and built something entirely her own. Cole’s story runs a different but parallel track. By his own account, he was the misunderstood, energetic child, the kind of person who had endless possibilities but few opportunities. Neither of them arrived in Alaska with credentials, safety nets, or industry contacts. What they carried was the particular clarity that comes from starting with almost nothing.
A Business Model the Market Hadn’t Seen
Bumble Expeditions is not a tour company that also happens to have a café. The structure is more deliberate: a single ownership umbrella spanning a four-acre private island, land-and-sea guided tours, the Misfit Island Cafe, travel planning services, a short-term rental property, and established relationships with cruise lines. Rather than building unrelated businesses, each new venture was designed to strengthen the others—giving Bumble Expeditions greater control over the guest experience while creating multiple revenue streams in one of the country’s most seasonal tourism markets.
Sara brought a background in finance to this build, an unusual entry point for an adventure travel company. After retiring from teaching in 2019, she was recruited into finance. That background is visible in how the business was structured. Rather than building unrelated businesses, each new venture was designed to strengthen the others—giving Bumble Expeditions greater control over the guest experience while creating multiple revenue streams in one of the country’s most seasonal tourism markets. Each division reinforces the others. Cruise guests flow naturally into guided land-and-sea excursions. Those tours connect to the company’s signature island experience. The café extends the brand into the heart of downtown Sitka, while the travel agency helps guests plan more comprehensive Alaska itineraries. A short-term rental and event venue broadens the company’s reach even further, creating an ecosystem that is both resilient and difficult to replicate. What has emerged is a luxury Alaska travel operation, one that didn’t start by targeting affluent travelers but arrived there through the quality of what it built. The integrated model helps mitigate the seasonality challenges that many tourism businesses face.
National media noticed before any formal publicity campaign existed. Editorial coverage in USA Today, Luxury Travel Magazine, and a feature on HGTV’s “Anchoring Down in Stika,” reflected the company’s unusual business model. In Sitka, a cruise destination that welcomes hundreds of thousands of visitors each year despite having a year-round population of roughly 9,000, Bumble Expeditions has built a vertically integrated operation that combines experiences, hospitality, and destination management in a way few regional operators have matched.
Bumble Expeditions is currently positioned for acquisition, with buyers and investors evaluating a business that carries prior media credibility, multiple revenue lines, and an asset, Mertz Island, that cannot be copied or relocated. For the growing segment of travelers seeking an exclusive Alaska travel experience beyond the standard itinerary, Bumble Expeditions occupies a category of its own.
Long Before There Was a Private Island, There Was the Feeling of Not Belonging
Cole and Sara each arrived at entrepreneurship from different backgrounds, but with the same realization: the conventional path wasn’t built for them. That idea became the foundation of Bumble Expeditions. Today, the word “Misfit” appears throughout the company—not because it’s clever branding, but because it reflects the people they intentionally build the business around.
“The Misfit reference comes from feeling like you don’t belong at the table,” Sara explained. None of that is decoration. “When we bought the island property, we were as surprised as anyone else that we’d made it happen.”
For cruise passengers seeking more than a traditional shore excursion, Bumble’s luxury private island experience at Mertz Island of Misfit Toys has become one of Southeast Alaska’s most distinctive offerings. It provides a level of access simply unavailable anywhere else in the region.
Bumble Expeditions has become a place where people with unconventional strengths often thrive. Some team members are remarkably young for the leadership responsibilities they successfully hold. Others are beginning their first careers. Some flourish in the fast-moving, ever-changing rhythm of tourism, where every day presents a new puzzle to solve. The company focuses less on whether someone fits a traditional résumé and more on whether they bring curiosity, resilience, initiative, and genuine care for guests.
“We try to be the workplace and support system we needed when we were young,” Sara said. “The kind of leaders who see potential before people see it in themselves.”
Sara’s earliest chapter began in foster care before she was adopted into a family with deep entrepreneurial roots. Cole describes himself as the kid people often underestimated, someone with plenty of potential but few opportunities to show it. Neither arrived by the route most people associate with entrepreneurship. Today, they own a private island and have built one of Alaska’s most unconventional tourism companies. Looking back, both believe their early experiences taught them to trust their own instincts long before anyone else did. The Spam-I-versary is still celebrated every year. It is not a joke or a piece of branding. It is a marker, a deliberate reminder that the starting point is rarely the whole story, and that the people least expected to succeed are sometimes the ones who end up changing what an industry looks like.
