Everyone Talks About the Private Island. The Real Story Is the People Behind It

Most visitors assume Bumble Expeditions' competitive advantage is its private island. It isn't. The cove, the wildlife, the kind of stillness that's nearly impossible to find anywhere else in Alaska. None of that is wrong to notice. It's just not the whole answer. Beneath the island's beauty sits something harder to photograph and far more important to the business: the people who built it, and the ones now running it. The real reason this company keeps growing faster than its competitors isn't sitting on four acres of forest and shoreline. It's standing at a dock in Sitka, Alaska, coordinating a schedule most executives twice her age would struggle to manage.

The People Getting the Work Done

Avi Rioux is nineteen. The title is Operations Director, which sounds like something reserved for someone twice her age, and the job matches the title. She manages international cruise line contracts, builds scheduling calendars, coordinates vendors, oversees tour guides, and serves as the company's boots-on-the-ground contact when something needs handling in person. Most companies in the Alaska tourism industry wouldn't hand that stack of responsibilities to someone fresh out of high school. Sara Hadad-Dembs and Cole Dembs, the company's founders, believed responsibility creates confidence faster than observation ever could, and it worked.

Brigit Wentworth has been with the company since Bumble Expeditions expanded to include the Misfit Island Café in 2024. She's twenty now, and she runs the entire food service operation: menus, vendor orders, scheduling, staffing, catering, and day-to-day restaurant management. Then there's Rob, the lead tour guide guests request by name, now in his second season and known equally for his depth of local knowledge and his relentless dad jokes. Across the company, other young employees are learning to lead tours, coordinate guest logistics, train new staff, and solve operational problems that would usually be passed up the chain.

None of them arrived with polished résumés or years of industry experience behind them. What they arrived with was curiosity, and a willingness to be trusted with something real.

How Responsibility Actually Gets Built

Handing someone a title isn't the same as preparing them to earn it, and Sara Hadad-Dembs treats that difference as central to how the business runs. Her own path winds through a classroom before it ever touched tourism. She spent years as an educator, and that instinct for teaching never left her when she moved into building the company. Somewhere along the way she also picked up a background in financial advisory work, which is why the numbers side of the business gets treated with the same seriousness as the guest experience side.

Co-founder Cole Dembs plays a different role in that mix. Around the office, he brings a steady patience that balances Sara's more direct, systems-oriented approach. Together, they spend real time walking staff through how the business actually functions financially, not just how to do their individual jobs. Revenue, margins, seasonal cash flow. Young employees are expected to actively look for inefficiencies and bring improvements forward themselves, rather than simply executing instructions from above.

That expectation only works if the training behind it goes deep enough to support it. Chelsea Huffman, a professional baker and owner of Confections by Chelsea, who studied under Sara years earlier in Colorado, flew to Alaska to work directly with the café staff, refining their baking techniques and tightening kitchen efficiency. Suzy Chiappetta, who brings more than thirty years of restaurant management experience through her company At My Table, returns to Sitka annually to educate and certify staff as food service managers. Anyone willing to put in the work can take the training. Those who pass move into shift supervisor and management roles.

The philosophy behind it all comes down to building the kind of workplace and support system the founders needed themselves when they were young. It isn't a slogan. It's closer to a working philosophy that shapes every hire the company makes.

What "Misfit" Actually Means

Around Bumble Expeditions, "misfit" isn't an insult or simply a whimsical piece of branding. It has become something closer to a hiring philosophy. The company has learned that some of its strongest employees are those who might not have looked like the obvious choice on paper: the teenager without management experience, the local guide whose knowledge can't be captured on a résumé, or the employee who hasn't yet recognized the extent of her own ability.

The founders aren't looking for people who fail to fit in. They're looking for people whose potential simply hasn't been recognized yet. Around Bumble Expeditions, that's what "misfit" has come to mean—not someone who doesn't belong, but someone who hasn't yet been given the opportunity to prove they do. Skills can be taught. Confidence can be built. Curiosity, resilience, and the instinct to take responsibility are much harder to manufacture.

Betting On Homegrown Knowledge Over A Résumé

The training doesn't stop at the kitchen door or the tour van. Every employee gets access to free training in any role they're curious about, whether or not it touches their current job. The company runs monthly appreciation outings built around adventure rather than a catered lunch in a conference room. By partnering with other local vendors, the team blows off steam by enjoying: treetop courses, kayaking trips, a float plane ride with a glacial lake landing, and days spent fishing together as a team.

The most unusual piece comes at the end of the season. Employees who complete the full year qualify for travel training, and in the 2025 and 2026 seasons, several staff members spent up to three months traveling through Europe and the United Kingdom. They navigated trains, planes, automobiles, and cruise itineraries the same way their own guests do, sitting through delays and long transfers and feeling firsthand what it's like to be a tired, disoriented traveler far from home.

The travel isn't simply a reward. It is a form of product development and hospitality training. Employees meet with adventure travel vendors abroad, sit in on other companies' tours, and build relationships with restaurant owners overseas to study how other hospitality businesses actually operate. They return to Alaska with a better understanding of the frustrations, uncertainties, and small moments of kindness that shape a guest's experience long before a tour begins.

The hiring philosophy behind it all leans toward spotting potential in people before they see it in themselves. Résumés rarely capture that. A season spent navigating a foreign train system where you don’t speak the language, or a month spent refining pastry techniques under a visiting mentor, tends to reveal it far more reliably.

Bumble Expeditions has already proven what it built: cruise partnerships, a private island, and a business that is difficult for competitors to copy. The quieter story sits underneath that one. It's the story of how it was built, one nineteen-year-old operations director and one traveling hospitality apprentice at a time.

Maybe that's why the word "Misfit" appears throughout the company. Not because the founders celebrate people who don't belong, but because they have built a business around recognizing potential before anyone else does. Boats can be purchased. Buildings can be leased. Even private islands can change hands. A culture that teaches overlooked people to become capable leaders is much harder to reproduce. The island will always draw the headline. The people are why this Alaska tourism company has a story worth telling at all.