I've been in the vacation rental industry for nearly 30 years. I started as a hot tub tech for my parents’ rental business in college, worked my way through almost every job a property management company has to offer, built a company to more than 500 homes and sold it, then eventually started another business.
After that long in an industry, it would be easy to assume you've learned most of what you need to know. Experience gives you confidence, as well as instincts that only come from having dealt with difficult owners, demanding guests, operational problems and changing markets over many years.
It can also make you comfortable, and that's where I think experienced operators need to be careful.
The vacation rental business has changed enormously, even in the past five years. Regulations are evolving, technology is moving quickly, guest and owner expectations are higher than ever, and we have access to data that can tell us far more about our businesses. If you assume that experience means your education is finished, eventually the industry will move beyond you.
Regulations keep moving
You can't fight modern policy with 1990s logic. The regulatory environment has changed enormously, and relying on how we've always done things is a good way to get blindsided. I've watched operators lose ground because they assumed the rules they built their businesses around would stay largely the same.
I've experienced that challenge firsthand. Years ago, I faced a dispute over fire safety requirements in Maryland that weren’t built for the vacation rental market. It would have been extremely complicated and expensive for managers to comply. With the support of VRMA, we were able to prove that impact in numbers for local policymakers, which eventually led to a much more proportionate regulation coming in.
That experience reinforced something I believe every operator needs to understand: you have to pay attention to the policy environment before a problem lands on your doorstep. You don't need to become a policy expert, but you should know what's happening locally, build relationships with officials and know where to turn for credible information and support.
That way, by the time a proposed regulation threatens your business, you’re already prepared to combat it.
Your experience needs updating
The level of professionalism expected in vacation rentals has risen considerably during my career. Service and communication that once differentiated an operator are increasingly expected as standard, while owners want a much clearer understanding of how their properties are performing.
Experienced operators have valuable instincts, but instincts need constant verification with data to make sure that the trends still ring true. I’ve heard stories of operators missing out on high-season pricing for important dates because they weren’t following the numbers, or the news. You should understand your profit centers, be able to justify your decisions, and know which KPIs matter to your business.
That doesn't mean chasing every trend. I've seen plenty of shiny new ideas come and go over 30 years. It means being curious and open to question whether the systems that served you five or ten years ago still make sense, or if something better has arrived.
Technology has to solve a problem
At the end of the day, we're still cleaning houses. We still have laundry to process, hot tubs to maintain and doors to unlock, and anyone who has spent time in operations knows that those fundamentals don't disappear because somebody invented a new piece of software.
Technology can, however, make that work easier. AI can reduce repetitive administrative tasks. Smart thermostats and sensors let you monitor a property when you can't be there in person. Software can help operators understand revenue and costs much faster.
I don't believe every property manager needs to become obsessed with technology. I do believe every property manager should understand what technology could do for their business and be willing to change when there's a better way of working.
Keep learning from the room
Some of the most useful things I've learned over the years have come from other operators. I've hired people with greater technical fluency than me and learned from them, and I've visited vacation rental companies while traveling because I wanted to see how they ran their operations. I still call peers when I want to understand how they're handling an issue, including issues I've dealt with before.
That's one reason I've remained involved with VRMA for so long. Education shouldn't be something you graduate from once you've reached a certain number of properties or years in business. Somebody in your professional community will have solved a problem differently, found a better system or developed expertise in an area where you have a blind spot.
Every operator should periodically look for the places where experience has replaced thinking. Ask a newer employee which processes they would change. Compare notes with another operator. Take a course on something you think you already understand.
The people who built this industry learned by doing, sharing and adapting as the business changed around them. If we want to keep building it, we have to keep doing the same.
There will always be another problem to solve and another person in the room who knows something I don't. I plan to keep listening.
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