Today we’d like to introduce you to Mike & Derryn Willis.
Hi Mike & Derryn, thanks for joining us today. We’d love for you to start by introducing yourself.
We are the Willis family, an adventurous family of three (five if you count our fur babies). Mike is a CFO of an aerospace company. Derryn taught inner city high school geography before having their daughter Charlize, who is now a spunky 8 year old. Our family is composed of three very driven hardworking people. We love projects and we are always dreaming and planning our next goal or adventure as a family. We also love to travel. We live for the excitement of waking up somewhere we’ve never been before, the joy of being encompassed by a different culture, the fulfillment we get from meeting and learning from people from all walks of life, and the lifelong memories we have made exploring the world together.
Our family, like so many others, struggled during the pandemic. Derryn has a very rare vascular autoimmune disease with lung involvement that forced us to social distance longer and more intensely then most. We struggled emotionally with not being able to do the things we loved, especially with not being able to travel. Our daughter would even pack her suitcase and sit on our staircase pretending she was on a flight. Some days it was a pretend flight to Paris and others a flight to South Africa to see family. Derryn would join her when the champagne was served and for the onboard entertainment, of course. We all missed the world so very much.
One evening, after several glasses of wine and a loaf of homemade sourdough (pandemic style happy hour), Mike and Derryn decided it was time for another adventure. We had owned a long-term rental in Seattle for over a decade. We bought it as newlywed kids while still finishing school. In that one conversation we decided it was time to finally sell that property and buy something that would better serve our family. A place that could not only be profitable but that we could enjoy as a family. The “where” was the fuzzy part. We both grew up in Oregon and so initially we discussed the Oregon coast, a place near to both of our hearts. But as natural researchers and planners, we did our homework and discovered that it might not be the most financially sound choice at that very moment. Months passed. We looked at property after property, market after market, from Arizona up to Washington. Then one day our close friend, Dustin Burke, suggested we look in Lake Arrowhead, a place that was very dear to him. We had visited Lake Arrowhead once before. We loved how it felt like so many of the little towns we grew up visiting as kids in Oregon. The rental market was great, and the real-estate market was even stronger. So, we decided to give it a shot and drove up to look for properties. We found a spectacular realtor, Michelle Calkins, who guided us to the perfect property. She was patient with us and beyond knowledgeable about the rental market and mountain community. Our friend, Dustin, heartbreakingly passed, in the mountains he loved, days before we went under contract on the Sundowner. We dedicated the cabin to his memory and every time we go up, we tap the dedication sign that hangs outside of our house and say a little silent “Hey Dustin.” The Sundowner started out with that much beautiful sentimental value and it’s just built and built for us.
We call the Sundowner, our “pandemic baby.” Instead of being frustrated we were all at home, we used the time to build something as a family. For almost two months Mike would work remotely from the cabin and help assemble furniture while on conference calls. Charlize would do school on zoom from the kitchen table and help shovel snow on her “recess”. All while Derryn tirelessly decorated, staged, and built our new family business. The Sundowner became the creative outlet Derryn needed and the home base we didn’t know we all needed. We used a difficult time in our lives to create something beautiful that has now become a huge part of who we are.
We named our cabin the Sundowner on Summit after the term “sundowner”. Derryn is a first-generation South African immigrant. And in South Africa a “sundowner” is a drinking tradition that marks the transition from day to evening. Or more simply put, a “sundowner” is an African happy hour. It felt appropriate to name it something that not only connects us to our global roots but also describes exactly the feeling we wanted our guests to enjoy during their stay- a relaxing moment enjoyed with loved ones, to mark the end of a spectacular day on the mountain.
We have owned the Sundowner now for nearly three years and hosted hundreds of guests. We’ve also hosted photoshoots for national and international brand campaigns such as Tilly’s and Fab Fit Fun and hosted several small events such as rehearsal dinners, retreats, and dinner parties. The Sundowner has become an outlet for Derryn to express her creativity, love for hosting, and for filling people’s cups with happiness and beautiful moments. She’s now even launching a second business, Vier Curated Celebrations. Vier has grown from the many beautiful celebrations she’s planned, styled, and hosted at the Sundowner.
We took a chance on building something beautiful out of a difficult time. The Sundowner on Summit is the retreat we all needed. As our guestbook says “Life is short friends, and the world is wide”. Never stop exploring your surroundings and allowing your travels to redefine who you are as a person.
Alright, so let’s dig a little deeper into the story – has it been an easy path overall, and if not, what were the challenges you’ve had to overcome?
Nothing worthwhile in life is obstacle-free. We have faced plenty of our own obstacles at the Sundowner. From launching a business during a pandemic and facing supply shortages while staging and furnishing, to juggling our other responsibilities in our lives while managing the Sundowner full time, to adjusting to mountain life and tackling everything from blizzards to very hungry bears, to learning how to best serve our guests needs. We’ve definitely experienced our share of growing pains. But the benefits of creating and managing the Sundowner always outweighs the challenges for us. We have loved sharing the Sundowner with every one of our guests over the last three years, and we get so much joy from hearing our guests had a wonderful trip. That makes all the hardships absolutely worth it for us.
We’ve been impressed with The Sundowner on Summit, but for folks who might not be as familiar, what can you share with them about what you do and what sets you apart from others?
The Sundowner on Summit is a stylish modern 3 bed 2 bath cabin in beautiful Lake Arrowhead, California. We are located minutes from the Lake Arrowhead Village. The Sundowner feels like a treehouse perched above a private wooded lot. We are a family-owned and operated business that prides itself on our guests’ experiences. We created the Sundowner with the idea of a retreat from the city, a travel adventure just an hour and a half from your front door. We wanted a place to laugh, breathe fresh air, and reconnect with loved ones. We also wanted to bring some of the experiences and joyful moments we had experienced traveling to our guests. We try to offer every one of our guests a personalized stay from the moment they first contact us, which is one of the reasons we decided to manage the Sundowner entirely ourselves. We make sure the cabin is fully stocked with all essentials and maintain a sense of luxury from high-end linens to designer furnishings. We work endlessly to ensure our guests have timely responses on all communication and that they never receive an automated response. And we love offering local recommendation so that they can experience all that our beautiful mountain community has to offer. The Sundowner is a special place, and we love that we can share that with people of all walks of life and help other families make memories, too.
What has been the most important lesson you’ve learned along your journey?
The most important lesson we have learned is the importance of taking a deep breath when things get tough and knowing that every challenge is a temporary moment in time that will pass. The vacation rental industry comes with so many ebbs and flows. We’ve had slow months, crazy busy months, and even times when Mother Nature has shut down our business entirely. Last spring our mountain was hit with the blizzard of a century. We had close to 12 feet of snow at the Sundowner! We had to shut our doors to our guests for nearly two months for our guests’ safety and also to help relieve some of the strain on our mountain community. It was a difficult time for our entire mountain. But it also really taught us exactly how resilient, hardworking, and compassionate our mountain community is. We got to know so many of our neighbors, and really all leaned into each other to get by. You have to be prepared for these slower, unexpected times when you own a business and know that it will pass.
Contact Info:
- Website: https://www.airbnb.com/h/sundowner
- Instagram: instagram.com/sundowneronsummit
- Other: instagram.com/viercuratedcelebrations
Image Credits
Tiffany J Photography
