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    5 Lessons That Helped Form a Successful Vacation Rental Management Company

    My 22-year career at IBM essentially started before I was born. My father started working for IBM in 1959 on NASA’s Project Mercury in Bermuda. IBM was his only job until he retired at age 49after 25 years of service. I started as a systems engineer, the person that came along with your mainframe computer free of charge. I ended my career as an executive where I managed teams as large as 140 people. I worked with a lot of smart people, had a lot of great mentors and was part of many great changes at IBM. Then I bought a second home and started renting it on VRBO, and I found a new outlet for my passions of family, the outdoors, traveling, leveraging technology and charting my own course. And that’s when I started a vacation rental management company.

    My 22 years of experience in a large corporation has equipped me to run my own business as a vacation rental manager. Here are five lessons I learned along the way.

    Be Willing to Fail

    “Recently, I was asked if I was going to fire an employee who made a mistake that cost the company $600,000. No, I replied, I just spent $600,000 training him.” – IBM Founder, Thomas J. Watson, Sr.

    One thing I like about the vacation rental business is that our guests and owners are very good at letting us know when we fail. The vacation rental business is a business of repetitive details. We essentially are called to do the same process repeatedly with perfection and enthusiasm. The fact that the hot tub is usually clean doesn’t matter to the guest for whom it is not clean.

    How well you handle details is important of course, but the focus should be on how to learn from a failure, so you don’t repeat it.

    At SkyRun, we consider it a type of failure when a guest needs to call us. Did they need to call for directions? A Wi-Fi password? Maintenance issues? Advice on what to do in the area?

    The guest is on vacation and for the most part, would rather not spend their time on the phone with us. When guests call, we try to think about why they had to call. Then we ask ourselves, what can we learn from that call and what can we change so that the next guest won’t need to make that call?

    Adapt and Change

    “Whenever an individual or a business decides that success has been attained, progress stops.” – TJ Sr.

    IBM started in 1911 as the CTR (Calculating Tabulating Recording) company. Thomas Watson was made General Manager in 1914. When I joined in 1985, IBM was still making copiers and typewriters as well as the mainframe computers it was known for. During my tenure, IBM expanded into personal computers, software and then into services to adapt to the changing marketplace of what our clients needed.

    It’s not hard to list occurring changes in our vacation rental industry. Just read the pages of Arrival each month. How did we as vacation rental providers adapt to the internet? The use of social media for communication? The movement from professional management to management by owner (and now perhaps back again)? Legislative hurdles? A trend toward OTA mega-sites that our guests prefer to use to find us?

    As every company in every industry, we will need to adapt to keep our edge.

    Constantly Question What You Think You know

    “I think there is a world market for maybe five computers.” – TJ Sr.

    Yes, Thomas Watson, founder of IBM said this. He very quickly saw that he was wrong, but that part isn’t quoted.

    It’s a healthy exercise to question what we ‘know’ to be true. Falling into heuristics is a recipe for failure. Just think about what our guests and owners need and want from their perspective. I’ve heard ‘owners and guests don’t want that’ about many things over the years. For instance, the use of OTAs, VRBO, Airbnb, Booking.com, instant booking online, lower commissions, add-on fees, multi-location management companies and the list goes on.

    When I started managing my own vacation rental in 2004, I started on VRBO. The game-changing listing-aggregation technology of VRBO allowed me to enter the market and compete with the large past client lists of managers. Their past guests and a whole new generation of guests were looking for vacation rentals online. Using my core skill-set from IBM, leveraging technology to create competitive advantage, I was able to get a start in vacation rental management without knowing much about it. Largely, by entering the market without preconceived notions, I was able to start a better company in some ways. We can learn from the new entrants in our market.

    Teamwork is Essential

    What the estimated 400,000-person team of Apollo 11 accomplished was arguably one of the greatest examples of teamwork in human history. It is critical to be able to work in a team. In addition to working together as a staff, I include being a part of VRMA, and working with our OTA, software and other partners in this need for teamwork. Working in partnership with our owners and guests are also included.

    No one person can do this business alone. Your ability to forge trusted, mutually beneficial and long-lasting partnerships will predict your success.

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