Building an Outdoor Hospitality Brand: Inside the Growth of Weekender Hotels

Outdoor hospitality is having a moment.

As the world becomes more digital, travelers are craving the opposite—fresh air, adventure, and places that feel connected to the landscape instead of disconnected from it.

But building a hotel brand around that idea isn’t simple.

It takes the right markets, the right properties, and a clear vision for how technology, experience, and place come together.

In this episode of The Unchecked-In Podcast, Bobby Marhamat sits down with Keir Weimer, founder of Weekender Hotels and CEO of Northbound Capital, and Jonny Jost, investor and Director of Growth at Northbound Capital.

What started with a single 30-room resort in the Adirondacks has grown into a rapidly expanding portfolio of outdoor-focused hospitality properties designed around adventure, place, and experience.

Keir and Jonny share how their upbringing in outdoor leisure markets shaped their view of travel, why Weekender focuses on drive-to outdoor destinations, and how they’re scaling a brand that blends modern technology with authentic nature-driven experiences.

They also open up about the operational mistakes, capital strategy lessons, and growth decisions that shaped the business along the way.

Key Takeaways

• Outdoor travel is the future of leisure hospitality as more travelers seek connection to nature and digital detox experiences.
• Weekender targets drive-to outdoor markets within two hours of major metro areas with strong seasonal demand.
• Technology should support the stay—not dominate it, enabling seamless check-in and smart rooms while keeping the focus on outdoor experiences.
• Scaling hospitality brands requires balance, maintaining property uniqueness while implementing consistent brand standards.
• Early mistakes taught critical lessons, including hiring too quickly at the corporate level and initially focusing on properties that were too small to scale.
• The company’s five-year vision includes 30–40 properties across multiple states, plus new sister brands under the Northbound Capital umbrella.
• Entrepreneurship works best when personal values align with professional goals, creating work that feels meaningful rather than transactional.