The Super Bowl of Vacation Rentals: 2023 Edition

Before I dive in, let me start by saying that there is no way this will possibly be an exhaustive assessment of what has become the standard bearer event for the vacation rental industry. These write ups were difficult in past years, and the task before me has only grown alongside the Vacation Rental Management Association (VRMA) ’s membership and attendance.

If you have any insights you believe are not adequately captured herein, PLEASE share them. This is meant to be a resource to the industry. Edits, comments, disagreements are welcome. I do not take them personally. Instead, and like all of you, I am just trying to learn and grow. We will all do it better together.

So, with that preface, let’s jump in…

How long have you been coming to this?

This is the question I constantly got on the first day of the show. A decade for those wondering. But that wasn’t why people were asking. Their next comment was the truly telling one.

“This year is crazy right?! They even closed registration! Think how big it could have been.”

This year was indeed different. Yes, the annual VRMA event is a staple for many in the industry, but it has never before reached the kind of scale we witnessed this year. 2,500 attendees, and that was when they stopped accepting new registrants. How big can it get? Let’s hope for even bigger venues in the future because as the same time as VRMA was holding its International Conference, Las Vegas was hosting the 25,000 person Money20/20 conference. The sky really is the limit.

This is exhausting!

Which perhaps brings up another point: how big do longtime attendees really want it to get? The vendor hall was overwhelming, and I say that as a vendor with TrackRevenue . It was like a city in and of itself, and even on the last day I was seeing old friends for the first time because everything was so large and spread out. As I write this, I realize there are many more I never even got the chance to see or speak to. It was a LOT.

This year’s VRMA was also far from the only event many attendees traveled to. For some of us, this time of year is “Conference Season” (in fact I am speaking at yet another one in November, Puerto Rico’s Rebook Conference if anyone is looking for another conference before the year ends!). The common refrain is “it’s a marathon, not a sprint,” but for those on the conference circuit it can sometimes feel like a sprint that just lasts as long as a marathon. Heading home this week are many tired bodies and minds who now need that break to process all they heard and learned, and who only then can begin to formulate the plan they will execute going forward to take their business to that next level.

Content is king, and the thirst for learning remains as strong as ever

While one attendee (granted, not a manager) commented that “it’s the sessions that really let conferences like this down,” I tend to think that was not the case for this year’s VRMA. With up to ten sessions going at any given moment, there really was something, and if we are being honest, more than one thing, for everyone. Whatever you came for, you had the opportunity to learn more about.

Don’t get me wrong, networking remains a huge part of why people come to VRMA, and on this front it certainly delivered. While its size made it virtually impossible to get the kind of time I might have wanted with old friends, it at the same time created opportunities to meet and learn from entirely new friends.

I know I was not the only one who appreciated this. Of all the sessions, the ones that seemed to receive the most positive reviews from what I heard were the Property Manager roundtables. Yes, hearing from “experts” on stage and in front of the room has its place, but it seems like the most value came from those times when people got to meet, hear from, and learn from their peers.

As one first time attendee manager commented on the last day: “I thought I was alone. I learned I’m not.” That value cannot be understated.

In those sessions I was able to personally attend, I can also say the audience was highly engaged. Several had standing room only. Few exhausted the questions people wanted to ask during the time allotted for Q&A, and in all, the conversation continued well after the official session ended. Presenters shared what they learned, and they also walked away learning more themselves, both from the questions asked as well as from the stories and perspectives shared.

Whether you have been in this industry for a few months or a few decades, there was a lot to still learn. It is like Heraclitus said so long ago: “No man ever steps in the same river twice, for it's not the same river and he's not the same man.” The same is true for what we “know” about this industry and our respective businesses. Both are constantly changing. We must personally and professionally continue to learn, adapt, and change with them. It is conferences like this that help us in that journey.

This industry parties like no other

Yes, this was Vegas, and yes there were some pretty epic parties. Not just the closing pool party at Caesar’s Palace, but also events at places like Ghost Bar and even the suite from The Hangover. Also, yes, people were hear to learn, and as Jason Sprenkle of Key Data bravely took the stage as the last session standing between people and the closing party to talk about data of all things, the conference organizers had a great sense of humor in playing P!nk’s “Get the Party Started” as his walk up song.

This brings up an important point, though. As an industry we know when to have fun, and we know when to be serious. For me this was never more evident than at the premier of Matt Landau ’s Homerunners. With a bar in the back of the room, and many people seeing each other for the first time in a while, even my painfully loud whistle could not quiet everyone as Matt kicked off the event.

However, when Matt uttered the words “Ft. Myers,” and started talking about the devastation he witnessed first-hand there, you could hear a pin drop. Our industry cares about our communities, and we care about each other. We all know how vulnerable we are to mother nature (we did just come through a global pandemic after all!), and we are there for each other when it happens. There is a time for fun, and a time to get to work. This year’s event did a great job joining the two together.

Advocacy’s pride of place

Speaking of which, it was incredible to see the prominence of advocacy at this year’s conference. I was personally in Steve Milo ’s session with Matt Curtis ten years ago when I could count the number of other attendees in the room on my hands alone. The amount the topic was not only discussed, but also acted upon (>$600,000 raised) at this year’s conference could not provide a starker contrast to how far we have come. The work Scott Leggat and others are doing with the “Right to Rent” campaign mean that we have the opportunity to get that much further.

Also, a big thank you to sponsors like TravelNet Solutions and Blue Star Innovation Partners who are hosting local events (the next one is in Frisco at the Dallas Cowboys ’ training facility for those in Texas). People like Steve, Scott, Sharon Walker , Tiffany Edwards, Merilee Karr and others have done a great job bringing an industry wide spotlight to this issue that impacts all of us. Now it is imperative on each of us to carry that spotlight forward into our local communities.

Another area that is hugely important to our industry and each of us is safety. Much like the people above have worked for years to bring attention and money to the issue of advocacy, I would be amiss if I did not call out here the incredible work that Justin Ford has done and is doing on the safety front. Ten years ago, when I was one of just a few people in that session with Steve and Matt, there were no sessions on safety even offered. This year, the topic came up more than once in the “top conference takeaways” podcast recording with Sarah and T. We have come a long way.

We have also gone Hollywood 

Which brings me to my next observation: the conference and the industry is about more than just what happens on the ground. We have fully evolved into multimedia.

From the red carpet interviews to start the show with Alex O. Husner🌎 and Annie Holcombe , to Matt Landau’s Homerunners premier, to running into Paul Stevens and Bart Sobies 🦾🌍 , both of whom have international podcasts, as well as Wil Slickers who has an entire podcasting network, Mateo Bradford-Vazquez and John Stokinger who are creating a murder mystery meets vacation rental podcast, to Sarah Bradford and Tim Cafferty closing the conference with a live recording for their own podcast, to Lauren Madewell schooling us all on how to engage with Gen Z via TikTok , it is clear we are innovating when it comes to how we tell our story, and to whom we tell it.

It really isn’t only about delivering a delightful experience on the ground. As a vendor I know as well as anyone that it is just as important to make sure our guests, owners, and clients understand the work we are doing, the impact it is having for them, and that they value it (and that we value ourselves) accordingly. We have to both do a great job AND be great story tellers to make sure people understand and appreciate that job. It is far from easy, but the tools and methods I have seen being developed and implemented leave me impressed and hopeful.

More deserving of the “international” title

For years this conference was just called “The VRMA Annual Conference” (as opposed to the East or West or seasonal forum). More out of aspiration than accurate description, a few years ago the VRMA rebranded the conference as the “International Conference.” And while there was a sprinkling of international attendees over the years, this year the global reach and feel was on full display.

For me this was most apparent in my session “Scaling for the Rest of Us: How, Where, and Why to Grow If You Haven’t Raised $100s of Millions, and Have No Plans to Do So.” Yes, we had Cristiana Carpini from Happy.Rentals all the way from Switzerland, but it wasn’t just her. Two-thirds of the other panelists ( Steve Schwab of Casago and Daniel Perry of BookStayHop ) manage homes outside the US, and the remaining panelist, Amy Gaster who managers hundreds of homes on Tybee Island, is now part of a VTrips family that you know it is only a matter of time before they expand outside the borders of the US.

That panel is but one example. I met people from all across North America, Europe, South America, Asia, and Australia. It is entirely possible that there were attendees from Africa as well, but with 2,500 people, please don’t judge me for not meeting everyone (I sincerely doubt Antarctica was represented however, perhaps an aspiration for future years).

This has always been a global industry. While there are many differences between countries, and even between cities within the same country, there are a lot of commonalities as well. At our core we are all trying to provide owners with excellent property management while at the same time delivering delightful experiences to our guests. Learning from operators all over the world allows us to share best practices as well as help rise the tide for the industry as a whole.

Opportunities and threats

For all that was great about this year’s event, there are opportunities for improvement as well as threats that we still face.

On the opportunities front, I have already commented on how advocacy and safety have grown in prominence. This is great, but there was at least one topic that was sorely lacking this year, and I am sure one that Bob Garner ⓥ🌳 has some thoughts on: sustainability. As one international attendee, Pete Smith asked me, completely baffled by its absence: “Is this just not something Americans think about?”

With the devastation brought be more frequent and intense hurricanes, wildfires, flooding, freezing, and more, I had to answer that we don’t just think about it, but we also must deal with it and plan for it like everyone else. Why something so important and impactful to all of us didn’t warrant space on the conference agenda is a question I cannot personally answer. I sincerely hope that this threat to all of us is an opportunity for expansion in terms of what we cover and discuss as we plan future events.

Another threat is the cloud that was mentioned incessantly during the conference: the looming recession and what it will mean for all of us. Seeing the over-the-top vendor booths in the vendor hall, the flood of new companies, the parties, the TikTok influencers not on the conference floor but rather online advising people how to become “ Airbnb millionaires,” I personally got an uneasy feeling. I kept thinking back to the story of Joe Kennedy (JFK’s father) knowing it was time to start shorting the stock market when even his shoeshine boy was giving him stock tips.

Have we reached the same point in our own industry? Only time will tell, but when the other shoe does drop, as it inevitably will, it will serve us all to be prepared. Winter is coming. It can still be fruitful, but you will just need to know how to adapt your business. The sort of learning and peer connections available at conferences like VRMA can be exactly the sorts of secret sauce you need to not only survive, but to even thrive through such times.

Welcome to the Hotel California…

With many people new to this industry, and people not necessarily new to the industry but just new to the VRMA conference, I also have another threat/warning. As the Eagles song famously says: “You can check-out any time you like/But you can never leave!”

The same seems is true in vacation rentals. Running into VacationRentPayment Founder and former VRMA Board member, Matt Golis , was certainly a pleasant surprise, though I was far less surprised to learn that the serial entrepreneur is back in the industry with a new and innovative product. Watch this space.

Catching up with Sarah Bradford was also a pleasant surprise given, as she pointed out several times, she sold her company and is no longer technically in the industry. However, she loves it (and us I am sure) so much, she simply can’t stay away, funding the conference on her own dime this time around.

Take this as a warning newbies. You may have just signed up for more than you bargained for…See you next year!