We Need to Reinvent Ourselves

Matt Landau
5/23/2024

In 2006, I purchased a vacation rental business in the historic district of Casco Viejo, Panama, and for a good five years, we were the only place to stay in town.

Neither me nor my business partner Keenan had any formal training in hospitality, but we were in love with our adopted neighborhood, and that passion rubbed off on our guests. And having no competition created a nice environment to learn, because the moment you immerse yourself in vacation rental management, you (or Keenan) get punched in the face with how operationally complex it is.

Replacing keys, coordinating check-ins, managing pricing and revenue, scraping poop off toilets … the gazillion variables that go into a consistent guest experience were screaming for control, so we created systems, processes, and standardization. To our surprise, it worked! Over the course of a decade, as the neighborhood surged in popularity, consistency was our differentiator from the crowd.

I eventually sold my vacation rental business and started VRMB, an online community for operators like me who were facing similar challenges. As membership grew into the thousands, it felt like a real breakthrough connecting so many individualized questions with standard operating procedures and best practices.

Soon, I was getting invited to speak at conferences about standards as it relates to vacation rental scale. As the industry skyrocketed, I got to follow an entire generation of operators leveraging consistency to find their sweet spot and make beautiful livings for themselves and their families. In the process, I got to visit a lot of them, too.

Then, a few years ago, the tide started to turn. What was once a unique marketplace became overhyped and commoditized. Unfair regulations threw a major wrench in plans. And with every attempt at logic, structure, and control, our capacity to innovate declined a little bit more.

At my own retreats and workshops, it became clear that our fixation with standards had become so ingrained that it started obscuring something crucial: our creative individuality—the very reason guests came to vacation rentals in the first place.

And as unpredictability soars, we find ourselves needing this creative individuality more than ever—only there’s no room to dedicate when we’re in the grind. The stress is palpable. It’s a real catch-22.

We need an intervention—to stop spinning plates (even if for an afternoon or a day) and go somewhere new, outside our comfort zone, to rediscover creative individuality like a muscle that strengthens with time. Without it, we can’t imagine any other way.

With some nurturing, creative individuality becomes our gateway to a more effective operating system: curiosity in asking better questions; authenticity in relationships and communication; and deeper connection with our teams and our guests.

Creative individuality is ungrounded without the foundation of professionalism. And professionalism without heart and soul does not scale sustainably. It’s our unique combination of the two that the world is hungry for right now.

The untapped potential for growth here is impossible to outline in one article. But in just about every marketplace, the time to differentiate more authentically is now. Rediscovering what we are passionate about is the ultimate business play.

A great case study is Heather and Robin Craigen. They first met working on a yacht charter back in 1994, then moved to Colorado and built Moving Mountains, one of the top luxury vacation rental companies in the world.

After 25 years, the Craigens could have kept doing exactly what they were doing, maybe added another mountain destination or three. But after their own creative discovery process, Moving Mountains announced a new division called Oceans, which offers yacht charters so guests can return with Robin and Heather to the sea.

“At this stage, Oceans is a leap of faith, but one that is grounded in wanting to push the boundaries of the experiences our guests will remember us for. It makes sense to us … people who ski, many of them also like to sail. But will enough of them follow us to the Ocean? This will (hopefully) be the business case for an idea that made sense in our hearts. We are rejuvenated to begin something totally new after 25 years, and that energy is what drives big leaps that occasionally make a big splash.”

Striking the balance between professionalism (which got us here) and creative individuality (where we have plenty of room to grow) is about much more than one innovation or outcome; it’s a mindset of being brave enough to put more of ourselves into business. Feeling more balanced and authentic carries a special kind of emotion that can transform any crowded, noisy, standardized marketplace into one that’s rich with exciting possibilities again.

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