Vacation rentals

Middle-aged entrepreneurism finds a new home

Vacation rentals

My wife, Laura, and I own two vacation rental properties in Prescott, Arizona, and attended the conference known as Vrbo, short for Vacation Rental by Owner, held in Phoenix.

It was impressive on several levels.

Everyone there was an entrepreneur, most by accident. That’s how we came to own our properties too.

Many of the folks we met started in this industry because they owned an “extra” property – a family cottage or a large first home they weren’t using fully but they didn’t want to divest. So, they started renting the property through one of the sharing services such as Vrbo or Airbnb or both.

Many were surprised to learn that they reduced their annual expenses on their properties and actually made money. And they enjoyed the industry. They liked the model so well, they began to look for and buy more properties in places they enjoyed visiting, putting those properties in the vacation rental system as well.

Two revenue streams

Some people found they were so adept at managing their rentals that they began to be sought out by real estate agents to manage rentals owned by others. That gave them two revenue streams: one risk and capital-intensive revenue stream via direct property ownership and one non-risk annuity stream via third-party property management.

For some people, the non-risk annuity stream was fast becoming the engine that drove their property acquisitions.

The majority of attendees were middle-aged or a bit past middle age. That makes sense, since it takes time to become a homeowner with equity, then longer to become empty nesters. But it was really refreshing to meet normal people who had enjoyed normal, primarily corporate careers, and who then became entrepreneurs as their “encore” careers. And like us, most of the attendees were married couples working their business together.

The Vrbo conference was a truly beautiful slice of Americana.

Vrbo’s headquarters is in Austin, Texas. It’s now owned by Expedia Group, the multi-billion-dollar company that has a large portfolio of companies such as Trivago,, Orbitz and Hotwire.

So, of course, given my bias toward small business, I expected to meet herds of corporate automatons, likely millennial age, reciting a party line without much depth. Laura even said she was going to do an “awesome” (a word she intensely dislikes) use count, but only counted three utterances of that word during the whole two-day conference. So much for our biases!

Clear guiding principles

The Vrbo people were exceptional. We were also pleasantly surprised to find the Vrbo reps actually eat their own dog food. All the reps I spoke with not only had a clearly defined corporate role which they could cogently articulate, but each also owned one or more of their own vacation rental properties, some listing them not only on Vrbo, but also on competing websites.

Wouldn’t it be great if every one of our employees was also a customer and also directly experienced the competition? These reps had firsthand experience of what works, what doesn’t, and most important, the true customer experience.

Can you imagine if every HQ employee at Uber drove three nights a week? I suspect Uber would have happier drivers. (And by the way, I meet very few drivers who are happy with Uber, but that’s a story for another day.)

Expedia’s “guiding principles” are clearly and simply stated on its corporate pages, and include principles such as “wearing” the shoes of customers and partners, having a bias to action, thinking both big and small, being data-driven and business judgement-led, simplifying, and being open, honest, humble, positive, and assuming positive intent. Expedia is clearly a corporate behemoth, but for us and the other conference attendees, it spoke the language of an entrepreneur.

Our politicians all like to talk about small business, entrepreneurs, and their impact on our country and our economy. But they typically like to focus on “flavor-of-the-day” businesses like tech or medicine.

I wish a few of those politicians would drop into one of the so-called flyover states and stay at a Vrbo or an Airbnb. They just might get a reality check of this new wave of entrepreneurs and this growing vacation rental industry (and maybe a relaxing vacation too to help them lighten up just a little). 

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As a serial entrepreneur, business and community leader since 1983, John Howman has led a variety of businesses, from technology to consumer products companies. He leads two groups for Vistage, a professional development group of CEOs, presidents and business owners. He can be reached at

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