Better Mondays Ep. 2 – My Experience Investing in a Short Term Rental Property

Have you ever been interested in more entrepreneurial investments like real estate?


Most of my coaching clients are interested in expanding their horizons around personal finance and investment alternatives, and real estate is a popular topic.

In this week’s episode of Better Mondays, I will share about my personal experience researching, purchasing, and operating a short term rental property. For me, short term rental properties in vacation areas always seemed like a fun type of investment. I could use it for enjoyment and to make some money.

Bluebird Chalet - Rental Property in Truckee, CA

Real estate investing can be one of the fastest ways to reach financial freedom.

After helping numerous financial coaching clients to invest in their first rental properties, I decided I would share my own experience with the hopes that it might motivate others to take a leap and explore investments or entrepreneurial endeavors that might help them to feel more personal freedom and enjoyment while also saving for the future.

My story:

Before I stepped away from my corporate career a few years ago, I knew I would need to develop enough revenue from various revenue streams to offset my work income. Real estate was at the top of my list and after saving and re-allocating investments, I made the decision to invest in a rental property to use for short term rentals in the Lake Tahoe area of California. The potential economics of the investment made me comfortable that I could replace at least a portion of my income, while I would also be able to enjoy one of the most beautiful places on earth with my family for part of the year.

So, in 2019, I took the leap. The home is 2,000 miles away from where I live in Illinois and I bought it without ever seeing it in person. Maybe not the best idea (to some), but it was easy to do with technology like Facetime and Zillow facilitating my process. Further, with technology like Airbnb, I was confident that I could also operate the rental from 2,000 miles away in about 4 hours per week.


Want to see the property discussed in this week’s episode? Visit the Airbnb page at this address: