What makes an experience worth building a business around? For these founders, the answers range from a private trek in Alaska to an olive oil tasting in Indiana and a first turn onstage in Melbourne. Meet the people behind these businesses and see how they turn local knowledge, personal interests and a knack for hospitality into experiences you can try.
Featured Entrepreneurs
Revel Treks and Tours | Kierre Childers
Kierre Childers moved to Alaska in 2015 to volunteer on a trail crew. After working in community outreach and guiding in Denali, she founded Revel Treks and Tours in 2021 to help visitors get to know Alaska while creating more opportunities for residents to get outdoors.
Based in Palmer, Revel plans private day trips and custom itineraries across the state. A trip might pair a guided hike with a visit to a local farm or time spent learning Palmer’s history. Childers says one nine-day itinerary supported more than 40 small Alaska businesses. The travel side of Revel also helps fund the Revel Adventure Club, which brings residents together for outdoor outings, including some offered free of charge.
When Childers and her husband welcomed their first child, she pared back the schedule and dropped mixed-group outings in favor of private trips. She ran fewer trips and brought in more revenue. The change also gave her more room to think about how to support her guides and give guests personal attention as the company grows.
“One of my biggest lessons this year has been that pruning can lead to growth,” Childers says. Since the start of the year, Revel had hosted more than 60 events for residents at the time she shared her story. About a third were free, giving people more ways to get outside together.
Plan a custom Alaska trip: Reveltreksandtours.com
White Wolf Private Tours | Dylan Gallagher
Dylan Gallagher started operating tours after college, overseeing North American trips for a global tour company. The work gave him a firsthand look at what luxury travelers wanted from a guide. He built White Wolf Private Tours around the kind of flexibility that’s hard to get on a group itinerary.
Based in San Francisco, White Wolf designs private outings for small parties, typically one to three guests. First-time visitors can start with a Private San Francisco Tour or plan a longer trip around Yosemite, Napa Valley or the Big Sur coast. A coastal hike and a stop for fresh seafood can be part of the same itinerary.
Gallagher’s advice to founders is to keep learning when the way forward feels uncertain. In his line of work, that can mean refining how an itinerary flows or getting better at listening for the detail that will make a trip feel personal.
“The important thing I learned is to always keep moving forward and improving, no matter how confusing or uphill the battle may seem,” Gallagher says. Starting in San Francisco gives guests a choice between getting to know the city and building an itinerary that takes them farther afield. The routes can be as short or as long as their plans allow.
Visit White Wolf Private Tours: Whitewolftours.com | Explore the custom California tour
The Outward Olive | Kristina DeRolf
The Outward Olive started with a request from Kristina DeRolf’s six-year-old daughter, Clara, who wanted to work with her family. They began selling at farmers markets in 2020 and opened their Crown Point, Indiana, tasting room in 2022. Today, guests can taste extra virgin olive oils and balsamic vinegars side by side and take home bottles filled by hand. The shop sources from small producers in Greece, Tunisia and Italy, and hosts private tastings and pairing experiences.
DeRolf, a nurse anesthetist and homeschooling mother, had spent years keeping her work and family roles separate. When her husband Jim injured his shoulder, the family decided to put more of their time into building the business together. Their daughters help in the tasting room and contribute ideas about sales and social media. The family also mentors young employees with their own goals in mind.
For DeRolf, bringing her family into the decisions changed how the business felt to run. It also gave them a say in everything from the people they hire to the events they host. That shared ownership is helping the family think beyond its local tasting room as it grows its events and gifting business.
“The result is a business that runs on shared ownership instead of my willpower,” DeRolf says. That approach carries through to the tasting counter, where guests can compare oils and vinegars before choosing a bottle. The business also creates gifts for companies that want to give people something they’ll use after the event.
Visit the tasting room: Theoutwardolive.com | Browse gift sets
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Meet More Entrepreneurs
Blue Rides and Water Bear Photography | Kimber Greenwood
Marine biology and years of diving inform Kimber Greenwood’s underwater portraiture. When she lost her photography studio, she began planning a new space and stepped into a second role as co-founder of Blue Rides. The dive travel booking platform grew out of her co-founder Erol Buchholtz’s experience being stranded without support on a trip. It gives divers practical details, including which boats have dedicated camera rooms.
Water Bear Photography also offers boudoir and elopement photography in Gainesville, Florida. At Blue Rides, Greenwood brings the photographer’s perspective while Buchholtz leads operations and builds the booking site.
Magic Expeditions | Alison Essner
Alison Essner turned years of planning trips for friends and family into a boutique agency that arranges theme park vacations, cruises and resort stays. When she had a chance to add more agents, she focused on improving systems and supporting the team she already had. Her test for growth is whether the agency can maintain the care clients came for.
Essner started the company in 2017, and referrals and repeat clients helped it grow. She’s now focused on giving her agents the tools and support to build itineraries around each family.
Learn more: Magicexpeditions.com
Favorite Grampy Travels | Nikki Hendrix
Nikki Hendrix grew up visiting Disney parks with packed peanut butter sandwiches, a tradition that shaped the concierge travel agency she later launched with her husband. The agency plans theme park vacations, cruises and luxury trips. Hendrix uses AI for administrative work and still spends time answering travelers’ questions personally, including in online groups where many families have yet to book.
Hendrix became a theme park travel advisor in 2015 and launched the agency in 2019. Its name came from her father’s blog about his favorite ways to spoil his grandkids.
Learn more: Favoritegrampytravels.com
Tarnfell | Grant Boonzaier
Grant Boonzaier sells saunas and cold plunge baths for UK homes and gardens. He uses AI to build tools such as product guides, freeing up time to answer the questions buyers have about construction, winter use and warranties. His approach includes explaining the limits of a product before someone commits to it.
The range includes outdoor, indoor, infrared and barrel saunas as well as chilled plunge baths. Boonzaier sees the time saved on building the site as time he can spend explaining the details customers need to make a decision.
Learn more: Tarnfell.com
Hard Knock Knocks Comedy School | Morry Morgan
In Melbourne, Morry Morgan’s five-night stand-up course takes students from writing and rehearsal to a graduation performance. Morgan realized that some students want to pursue comedy, some want to become better speakers, and others simply want to try something intimidating in a supportive room. Recognizing those different goals helped him explain who the school could serve.
Students work with experienced comedians and leave with a recording of their graduation set and professional headshots. For some, getting through that first performance is the milestone they signed up for.
Learn more: Hardknockknocks.com
LuxuryStayWorld | John Sener
A Scottish castle or a family-run ryokan can lose much of its character on a page built around rates and availability. John Sener started LuxuryStayWorld to give distinctive properties room for a longer story, with readers booking directly. Dropping listing fees and commissions helped him build trust with properties, some of which began approaching him after seeing his coverage.
The collection spans Europe, Asia and the Americas. Each feature begins with a conversation and gives the property a chance to review its story before it appears.
Learn more: Luxurystayworld.com
RJVIPGP | Richard Jarocki
Richard Jarocki’s years in the automotive industry introduced him to Formula 1, while trips to São Paulo rekindled his interest in food and travel. He writes about restaurants, hotels and race weekends he’s experienced firsthand while working full time. His business lesson is patience, and the question he brings to his coverage is whether the experience was worth it.
He originally ran a website focused on São Paulo before launching RJVIPGP in 2026 to write about a wider range of destinations. He wants readers to know what he actually thought of a meal or a stay, including when the service fell short.
Learn more: Rjvipgp.net
ChatYourTrip | Herbert Kerkhoff
Herbert Kerkhoff spent six months building ChatYourTrip and discovered soon after launch that the site wasn’t indexed by Google. The experience made marketing and discovery part of how he thinks about building a travel tool. He also learned to pause and recognize what he’d accomplished, even with a long list of improvements still ahead.
Kerkhoff started the project in February and launched in August. Seeing how much work remained after launch made him more deliberate about celebrating what he had already built.
Learn more: Chatyourtrip.com
Spanish and Go | Jim Fricker II and May Larios García
Learning Spanish led Jim Fricker II to meet May Larios García, a language teacher from Colima, Mexico. Together, they built Spanish and Go around practical language learning through retreats, a podcast and an online community. They’ve added more live events and conversation clubs so students can continue learning with people they meet long after a trip ends.
One student first joined a retreat in Guanajuato, then kept studying online with teachers he’d met there. He later planned to return for a Día de Muertos retreat in Cholula.
Learn more: Spanishandgo.com
