How to Become a Ski Home Owner | Entrepreneur Aligned
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Entrepreneur’s Wealth Digest

How to Become a Ski Home Owner

Because I am located in Colorado and am a ski home owner, I want to walk through the three-step decision making process we here at Entrepreneur Aligned take clients through when they are purchasing their own ski homes. This process works well for any vacation or seasonal-use property, but there are certain steps, locations and seasonal elements that are specific to mountain town ski properties.

Defining your vision

Start with clarifying your vision for the property. What do you want to use it for? What times of the year will you be there? Who is coming with you? What will each day-to-day be while you are there? Is this a six bedroom house in the town of Crested Butte or a two bedroom slopeside condo in Vail, where you can walk to après ski at the end of the day?

Try and picture your favorite ski trips from the past and what made them epic adventures and/or amazing family time. Write those memories and features down, and create a list of the things that are most important to you. Here is an attribute checklist you can use:

  • Logistics - What proximity do you want to ski lifts, transportation and dining?
  • Parking - Ski town parking is typically at a premium. How many spaces do you need?
  • Storage - Ski gear is not small. Cluttered spaces are less fun to be in and can make things difficult when entertaining guests.
  • Creature Comforts - Finishes, hot tubs, fireplaces, seating, etc. What do you like?

Defining your business model

Now that you have a checklist, think about the model you want to run as you stay in these places. This process assumes that you do not have unlimited funds to purchase your ideal property without any tradeoffs. Some of the slopeside houses in Aspen or Telluride are empty 50 weeks per year and cost tens of millions of dollars. The owners of these homes value optionality and privacy, and they view their homes as investments in order to allocate excess capital. If you are reading this, I assume this is not you. We are in the realm of properties costing $1-$5M, and the financial model matters here. With that said, here are three primary models that have seen success.

1. Go small and do not rent at all.

  • This model offers optimal flexibility and works within your cash flow so you do not feel like you have to use the property all the time.
  • It typically does not allow for big guest events, which means you may need to rent a supplemental place nearby for those occasions.

2. Go big and rent long-term in the offseason.

  • With this model, there is less management and oversight than with short-term rentals.
  • Single tenant use is typical.
  • This model is great if you only use the property during ski season or summer
  • It works well for reverse snowbirds (those from hot weather areas who summer in the cooler mountains). You rent during the high-income winter season, and use it personally during the lower-income summer season.
  • It allows for bigger guest events.
  • This model can be helpful when there are short-term rental restrictions in your preferred area.

3. Go big and rent short-term throughout the year.

  • This model gives you consistent access to the dates and space you want, but it offers little optionality.
  • Depending on the property and how much you use it, this type can cash flow well.
  • This is the most management-heavy option, and it creates wear and tear on finishes and furnishings.
  • There are some great short-term rental income estimator tools online you can use to roughly calculate your income potential.

Taking a test drive

Now that you have your vision and the model that you want to run, hop online to see what matches your functional list. If you are planning ahead for the season, you can also check online for monthly or seasonal rentals.

First, pick a property or properties and take them for a test drive. Book trips or rental periods in something that closely matches what you are looking at for purchase. This is a great time to validate whether you are going to get what you want out of a similar property. For example, if you initially thought you wanted to be walkable to restaurants but ended up cooking most family dinners in the property’s kitchen, maybe you can buy further out of town after all. Or, maybe you thought you and your family would be fine taking the in-town shuttle bus, but they complain about it. In that case, you might want to look at something that is walkable to the lifts.

Once you have a few trips under your belt, you can make a much more informed decision about the property and rental model that makes the most sense. You may end up loving the rental side and keep doing that, or you may learn that what you thought all along is exactly what you wanted. Either way, you get to make an informed decision and set yourself up for years of fun ahead.


If you have a question or simply want to talk through your financial planning, we are here to help.

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Wealth Digest





DISCLOSURE: Jarrod Musick is an officer of Destiny Capital and Entrepreneur Aligned, a DBA of Destiny Capital. This article is for informational purposes only and should not be relied upon as a basis for your investment, business, or personal financial decisions. We recommend consulting with your wealth advisor, CPA/tax advisor and/or attorney, as applicable to your situation, prior to implementing any new tax, legal, or investment strategy. Advisory services provided by Destiny Capital Corporation, a Registered Investment Adviser.


Jarrod was born into financial planning and solving financial problems. With his financial advisor father Steve telling stories about finance around the dinner table from an early age, the idea that everyone has a different financial situation was always there. After an early professional career spent in nonprofit and government, Jarrod came back to his roots helping people plan and invest in 2011. Since then, he has worked with individual clients, led internal teams and ultimately became partner and the CEO of Destiny Capital in 2017. With a passion for helping entrepreneurs change the world, Jarrod ultimately oversaw the creation of Entrepreneur Aligned in 2020. With both Destiny Capital and Entrepreneur Aligned, Jarrod leads teams that help people live lives of abundance where money is simply a tool to let everyone be a positive force for the world around them. When he isn’t working with the talented teams for EA and DC you can find him chasing his twins, wily trout or a podium spot at an OCR race.

Jarrod Musick


Posted: 11/03/2023

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