My wife and I started Outpost in September of 2014 when we were 24 and 26, respectively. We managed our own home as our first property, and almost five years and 185 properties later, we are now the largest vacation rental company in Jackson Hole. Through significant growth and change, one thing has remained constant.

We treat each guest of Outpost as if they were staying at our own home. Guests care more for your home if they know someone personally owns and loves the property rather than it “just” being managed by a rental company.

– Mekki Jaidi, Broker & Owner  •  307.690.4790 ext 3


We have a department dedicated to revenue, which allows for our pricing and strategy to shift daily. Our methodology depends heavily on analyzing data, but we also focus on the psychological nature of the booking cycle. Herd behavior influences booking patterns; we recognize trends and therefore have a strong grasp on finding the perfect balance between occupancy and price.

According to KeyData Dashboard, Outpost boasts the highest occupancy in the region at 66% available occupancy with our competition falling nearly 30% behind. That’s nearly 110 less nights booked based on a 365 calendar year. We are able to achieve impressive gross rental numbers for each home in our portfolio and continue to improve on these figures year after year.

Available occupancy is defined as the ratio between nights booked versus the total nights available for booking. It is a true measure of how well we as a company are able to book homes. The calculation strips out owner stays and only factors nights available for guests to book.

We understand that our homeowners want to enjoy their homes throughout the year while still earning rental income. Although you are free to visit whenever you’d like, knowing when you can expect to maximize income can help you plan your trips accordingly. The following chart depicts the fraction of yearly income earned per month, and is separated into homes in the Aspens, Teton Village, and the town of Jackson.

If you would like to see a more detailed breakdown that depicts weekly income as a fraction of the entire year, we would be more than happy to pass this along. Outpost’s size and growth allows us a large sample of data to analyze the booking cycle of an array of homes in order to provide the most accurate information to our current owners and prospective homeowners.

We are always happy to deliver projections for your current home. Please feel free to reach out by either emailing or calling calling 307.690.4790, extension 3. Whether you are looking for information that may be useful in renting your home or deciding which rental home to purchase, we are here to help.


In addition to seamlessly reserving your home through our online platform, guests can utilize our sophisticated booking engine to also add on discounted lift tickets or trip insurance as lodging packages.

Our system will continue to see improvements which will not only enhance the guest experience, but also to allow us to maximize your income. The following screenshot shows the ease of adding discounted lift tickets to a guest reservation:

We are constantly improving our systems, experiences, and strategy to ensure that we maximize your rental income. Innovation is a large part of our culture at Outpost as we strive to deliver an exceptional owner and guest experience.

Please feel free to reach out with any questions whatsoever. We would love to chat with you about the potential of your home or future home!  •  307.690.4790 ext 3  •  307.690.4790 ext 3

Before placing you in a set structure, we like to really understand our homeowners’ financial goals. The Owner of Outpost studied Operations Research: Financial Engineering at Columbia University’s School of Engineering and Applied Sciences and can therefore create and tailor structures to better suit your overall goals.

While we do offer more straight-line commission structures, we can also think outside the box and discuss targets, incentives, etc. Our program is extremely owner friendly.  •  307.690.4790 ext 3

We'd Love to Chat!

Connect with us and we’ll share our thoughts on how much your property can make on an annual basis. We can also let you know the ins and outs about our program, including what it would look like to first join. There are absolutely no initiation fees and no charges when joining!

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