By Leslie Kilgore EBS STAFF
For Tim Drain, what started as “just one winter” at Moonlight Basin turned into 15 years in Big Sky. Now, regional manager of business development for Natural Retreats and chair of the Big Sky Chamber of Commerce board, Drain has helped shape both the vacation rental industry and the community he calls home. Explore Big Sky sat down with Drain to talk about his journey from seasonal work at Moonlight to leading Natural Retreats and serving the community he loves.
This series is part of a paid partnership with the Big Sky Chamber of Commerce. The following answers have been edited for brevity.
Explore Big Sky: When did you first move to Big Sky or the region, and what initially brought you here?
Tim Drain: I moved here in the fall of 2010 and had a job offer with Moonlight Basin. I had never set foot in Montana before. My wife Kristen and I thought we were going to be out here for just one season. I was the ski rental and retail manager at Moonlight and Kristen had a job in the cash control office there. The plan was that we were going to come out and spend the winter here, then go back out to Washington, but we’ve been here ever since, 15 years, and it was supposed to be one.
EBS: How did you hear about Moonlight Basin and how did you get your job there?
TD: It was completely random. I was at work and actually getting ready to lead a sunset kayak tour in mid-April in the San Juan Islands. It was freezing, so I was trying to warm up by drinking tea and eating soup at the only food and beverage outlet open at the resort marina, and a guy was sitting next to me at the bar having cocktails and appetizers with his wife. I heard him mention Moonlight Basin, and I had heard good things about it, so I chimed in on his conversation. We started chatting for a little while, and I asked him, “What do you do at Moonlight?” He said, “Oh well, I own it.” That was Lee Poole.
EBS: When did you start with Natural Retreats?
TD: I went from Moonlight to Big Sky Luxury Rentals in 2015. It was December of that year when Natural Retreats acquired Big Sky Luxury Rentals, so I then became a Natural Retreats employee. Within a few months, I was promoted to general manager. I did that for about six years. We built the business up to a large enough scale that it didn’t make sense for the general manager to be running the day-to-day operations and managing the entire team while also recruiting homeowners and building our portfolio, so we created a new position in Big Sky, which is the regional manager of business development, and I’ve been in that position now for about four-and-a-half years.
EBS: You’ve worked for Natural Retreats for quite a while. What has kept you there, and what’s great about the company?
TD: It’s a great company culture, and the company very much values all of the employees. We have really great, industry-leading benefits for anyone in the vacation rental space, or in the hospitality space, for that matter. But in addition to just the actual benefits, it’s a great company culture to work for. Everyone, from the top down, really values the input that everybody in the company brings. We feel appreciated and valued.
EBS: Can you give us a brief overview of some of the services you offer? What sets you apart from competitors nationally and regionally?
TD: The primary services that we offer are property management and vacation rental management. Many smaller companies do just the vacation rental side of things, and then they subcontract everything on the maintenance side. Others do the property management side while the homeowner manages their own bookings. There are different models that work for different businesses and for different customers. Natural Retreats is a full-service company, so we provide all of the property management services and manage bookings and guest stays.
EBS: Do you have a big team?
TD: Yes. We provide services for everything that a homeowner needs with ease and the peace of mind knowing that when they’re back at their permanent home, they can essentially sit back from afar and their Big Sky home is taken care of. And then on the flip side, when they come out here on vacation, they don’t have to feel like they’re coming out to work on projects. They’re coming into a home that’s well taken care of and that’s prepped and ready for their arrival, as if they were a guest checking into the home.
EBS: Does that make a big difference for many of the homeowners you service here in Big Sky?
TD: Yes. All of our concierge services are also available to our homeowners, just like they are to our guests. So really, when they’re here, owners can feel like they’re a guest in a luxury property too, and their property is being cared for.
EBS: What else makes Natural Retreats stand out here in Big Sky?
TD: We have a very well-staffed team of property managers, a general manager, an assistant general manager, an operations coordinator, a solid maintenance team, and what that allows us to do is keep a much lower ratio of individual homes to property managers, allowing us to spend more time and care on each home. We have a solid support system for every homeowner.
EBS: How do you see Natural Retreats growing here in the property management realm as Big Sky overall continues to grow?
TD: We’re not worried about having the biggest home count. We just want to have the best properties and provide the best services for our guests and for our homeowners. That’s what really creates a stronger business for us.
EBS: Can you tell us more about your engagement with the local community?
TD: I’m involved in the local community, personally and also while representing the Natural Retreats brand. The company sponsors many local events and different local nonprofits. We sponsor several of the Chamber of Commerce events and the Moonlight Community Foundation golf tournament this year.
EBS: And personally?
TD: For 10 years now, I’ve been on either the Visit Big Sky board of directors or the Chamber of Commerce board of directors. I’m currently the Chamber of Commerce board chair. My biggest highlight from being on the chamber board, and as board chair, is being able to elevate the services that the chamber provides to the business community and the community as a whole. And to help steer the organization to take on new initiatives that meet new needs.
EBS: What’s the best business advice you’ve received during your successful career?
TD: If you fail to plan, you plan to fail. You always need a plan as to what you’re doing, and be able to adapt that plan as well. Have a roadmap, have a northstar to follow, and just keep yourself moving in the right direction.
