We were lucky to catch up with Kylan Pimley recently and have shared our conversation below.
Kylan, looking forward to hearing all of your stories today. One of the most important things we can do as business owners is ensure that our customers feel appreciated. What’s something you’ve done or seen a business owner do to help a customer feel valued?
One of the most impactful ways we’ve found to ensure vacation rental guests feel genuinely appreciated is by anticipating their needs and preferences with meticulous attention to detail. Our primary goal is to anticipate guests’ needs and make them feel acknowledged and valued.
For example, when we host families with children in our rental properties, we take proactive steps to understand their unique situation. One of my favorite personal touches for these families is to provide delicious snacks upon their arrival. This thoughtful gesture is aimed at alleviating the stress that often accompanies travel, especially for parents managing multiple tasks like unpacking, entering door codes, and tending to children with low blood sugar after a long travel day.
Upon arrival, our guests are welcomed with a personalized basket filled with snacks and house-specific stickers, designed to delight both parents and children alike. What sets this gesture apart is its purposeful intention: to reassure parents that we’re here to support them every step of the way. Our welcome baskets not only feature local treats and snacks for the kids but also include local coffee and wine for the adults, ensuring that everyone feels catered to and appreciated from the moment they walk through the door.

Great, appreciate you sharing that with us. Before we ask you to share more of your insights, can you take a moment to introduce yourself and how you got to where you are today to our readers.
Kylan is the founder of Go Gorge Getaways. She launched this journey in the short-term rental sector in 2018, leveraging her 20 years of experience in long-term property management and experience with athlete hospitality at Nike Headquarters. Gradually, she expanded her portfolio, curating a thriving hosting business. Today, she maintains an unwavering dedication to guest satisfaction, with a keen focus on streamlined processes and effective communication. Kylan’s commitment to ensuring the safety of short-term rentals, as well as fostering a sustainable and enjoyable neighborhood experience, is evident in every aspect of her work.
Kylan thrives on navigating the dynamic landscape of the short-term rental industry. She continually updates her expertise in revenue management, travel consumer behavior, market analysis, and emerging hospitality trends. Her ultimate goal is to enhance her guests’ experience in the Columbia River Gorge while giving back to her community. She also LOVES putting together guest welcome baskets!
When she’s not immersed in hosting, Kylan relishes quality moments with her husband Jake and their two teenagers. She frequently escapes to the slopes for skiing or trails for hiking, often conceptualizing her next innovative project.

Have you ever had to pivot?
The COVID-19 pandemic challenged business owners worldwide to demonstrate resilience and adaptability, and the vacation rental industry was no exception. By April 2020, the entire travel sector had come to a standstill. Stay-at-home orders were widespread and seemed indefinite. Each morning, I faced the reality of double-digit reservation cancellations across all our properties. The outlook for my vacation rental hosting company appeared grim. Although consumer behavior in the travel industry was shifting irreversibly, I hadn’t fully grasped the extent of those changes at that point.
However, as the uncertainty of the ongoing pandemic continued to build, another facet of our business thrived unexpectedly. Our small mortgage company saw a surge in activity as interest rates plummeted and people confined to their homes sought to renovate the very spaces they found themselves stuck in. This unforeseen boom allowed us to pivot strategically: we moved into one of our vacation homes, quarantining with elderly parents and exchanging assistance. While I managed all grocery shopping, the grandparents provided invaluable help with online schooling.
Simultaneously, we seized the opportunity to invest in improvement projects for our vacation rentals, anticipating that guests would appreciate these enhancements once travel resumed.

Any stories or insights that might help us understand how you’ve built such a strong reputation?
In response to the Airbnb boom following the pandemic, my approach to distinguishing myself in the vacation rental industry revolves around adopting a comprehensive perspective on community issues. I actively engage in our local tourism alliance and facilitate meaningful discussions on topics such as affordable housing challenges. My reputation as a vacation rental host is built on focusing on the small, important details for our guests and ensuring the viability and safety of our guests and community.
I immerse myself in understanding how to sustainably coexist as a business owner involved in vacation rentals, long-term rentals, land development projects, and a small mortgage company. Recognizing the interconnectedness of these endeavors, I prioritize listening and learning from various community members to inform my decisions and actions.
Contact Info:
- Website: https://www.gogorgegetaways.com
- Instagram: @gogorgegetaways
- Linkedin: https://www.linkedin.com/in/kylan-pimley-80208520/







