Today we're welcoming Dawn from The Olive Jar, an experiential marketing studio specializing in vacation rental design and guest experiences. Dawn's path to this work is unconventional—she started in film advertising writing movie trailers, moved into documentary filmmaking with brands, and then spent years producing immersive culinary experiences before COVID shut down her entire industry. When short-term rentals exploded during the pandemic, she discovered that creating intimate experiences for cabin guests combined everything she'd learned about storytelling, production design, and emotional connection.

What makes Dawn's approach different is her insistence that branding isn't just a logo or color palette—it's about creating a cohesive feeling from the moment someone discovers your property until long after they've checked out. She talks about branding as "vibe creation" and argues that if you have to tell people your stay is luxurious or experiential, you've already failed. The experience should speak for itself through carefully curated details.

We explore why small touches like bubble wands or a doggy guest book can be more powerful than expensive amenities, how to translate your brand into marketing without overwhelming yourself, and why vulnerability and humanity in your communication matters more than perfect polish. Dawn shares her process for creating brand story guides that help hosts identify their ideal traveler and design experiences that create what she calls "core memories"—those multi-sensory moments that stick with people long after they leave.

Whether you're struggling to define your brand, wondering how to market without being salesy, or trying to create genuine connection with guests through thoughtful details, this conversation offers a framework for thinking about hospitality as storytelling and generosity as your most powerful marketing tool.

Instagram: @theolivejar.co

Booking Site: https://theolivejarhostingquiz.scoreapp.com/

Instagram: @cozyrockcabin

Cozy Rock Cabin: https://staycozycabin.holidayfuture.com/listings/311027
Cozy Camp Sebec: https://staycozycabin.holidayfuture.com/listings/311051
Cozy Rock Website: http://www.staycozycabin.com

YouTube Channel: https://www.youtube.com/channel/UC_FgMwAgvORd1IwlH1nlC9g

Today we're welcoming Sarah and Matt from Hyggeland Cabin in upstate New York, who built their own cabin from the ground up—a decision born from a COVID-era road trip and a serendipitous introduction to Den Outdoors cabin plans. What makes their story particularly compelling is they started dating in May 2020, bought land together on their one-year anniversary, and spent the next two years building a cabin while navigating a brand new relationship.

Sarah grew up in a handy New Hampshire household where building additions and self-sufficiency were the norm, while Matt came from Hong Kong and Los Angeles with zero carpentry experience. Their journey together became as much about Matt discovering a new identity as a blue-collar builder as it was about creating a physical space. They touched every piece of wood in their cabin—Matt sanding and Sarah staining—while managing the project themselves and learning to navigate decision fatigue, budget overruns, and relationship dynamics.

Their unique living situation adds another layer: they actually live in the cabin except when it's rented, which means they're constantly commuting two and a half hours from their Westchester apartment for turnovers. This hands-on approach has given them deep insights into what makes a space functional, from hidden storage with childproof locks to phone chargers at every bedside.

We explore their philosophy of building with love, why they chose hourly contractor rates despite the uncertainty, how they've embedded themselves in their local community through volunteer firefighting, and their honest reflections on burnout, relationship strain, and why they're already planning to build another cabin despite saying they'd never do it again.

Whether you're considering a DIY build, navigating a major project with a partner, or wondering how to balance living in your rental property, this conversation offers candid insights from a couple who learned everything the hard way.

Instagram: @hyggelandcabin

Booking Site: https://www.airbnb.com/rooms/1150094111589366186?fbclid=PAZXh0bgNhZW0CMTEAAaedjMdYkKtkd_J6LLAt7glhegEPG8HNDSbdKcsDtPzogFSuvyAS2WsHIqm5mg_aem_bAsfyE2-cGhia2He_BtZ8Q

Instagram: @cozyrockcabin

Cozy Rock Cabin: https://staycozycabin.holidayfuture.com/listings/311027
Cozy Camp Sebec: https://staycozycabin.holidayfuture.com/listings/311051
Cozy Rock Website: http://www.staycozycabin.com

YouTube Channel: https://www.youtube.com/channel/UC_FgMwAgvORd1IwlH1nlC9g

Today we're welcoming Rick and Lindsay from the south coast of the UK, who created Looking Glass Lodge—a stunning example of how cabin culture translates across different countries and landscapes. What makes their story particularly compelling is that they didn't set out to become cabin hosts at all. When Rick's father retired from managing a nature reserve, Rick and Lindsay inherited a piece of woodland that had been lovingly cultivated over thirty years, and they faced a choice: how do you maintain and preserve this special place while also sharing it with others?

Their solution was to create a cabin so thoughtfully designed that it feels like a natural extension of the forest itself. Working with architect Michael Kendrick, they spent two and a half years designing a structure that sits at just the right angle in a natural clearing, maximizing the connection between indoor and outdoor spaces without disrupting the ecosystem his parents had spent decades nurturing.

What struck me most about their approach is how they've flipped the typical cabin business model. Rather than extracting profit from the land, all income from Looking Glass Lodge goes directly back into maintaining the woodland and nature preserve. They're essentially using hospitality as a conservation tool, giving people the opportunity to experience this special place while ensuring it remains protected for future generations.

We'll explore their philosophy of "selling nothing"—how they've intentionally avoided adding hot tubs, barbecues, and other typical cabin amenities because they discovered their guests just want to disconnect completely. We'll dive into their design philosophy, from sourcing unique Scandinavian furniture to the biophilic design principles that help guests feel truly immersed in nature, and why they believe maintaining a seamless connection between cabin and woodland is what makes a cabin truly special.

Whether you're interested in sustainable cabin business models, designing with minimal environmental impact, or just want to hear about a place where doing absolutely nothing is the main attraction, this conversation offers a different perspective on what cabin culture can be.

Instagram: @lookingglasslodge

Booking Site: https://www.lookingglasslodge.co.uk

Instagram: @cozyrockcabin

Cozy Rock Cabin: https://staycozycabin.holidayfuture.com/listings/311027
Cozy Camp Sebec: https://staycozycabin.holidayfuture.com/listings/311051
Cozy Rock Website: http://www.staycozycabin.com

YouTube Channel: https://www.youtube.com/channel/UC_FgMwAgvORd1IwlH1nlC9g