The New Face Of Vacation Rentals?


This past weekend in a closed-door meeting at the Drake Hotel in Toronto, Canada, I concluded one final piece of information about the vacation rental industry, then placed a confident bet that independent vacation rental owners and managers will triumph over the larger listing sites adversaries.

The ongoing theme of David versus Goliath in the vacation rental industry is an intense one:

It's hard to find any property host who doesn't have a passionate viewpoint on how big listing sites like HomeAway and Airbnb have changed the industry. And very rarely will you meet an industry professional without his or her own unique prediction of shifts, changes, or acquisitions still to come.

So what did I observe in a time of such uncertainty that pushed me over the edge to fully commit all my time, my money, and my faith to one side?

The Backstory​

The private event in Toronto was a "hot seat" style workshop, designed to help twenty select independent owners and managers solve one big challenge in their vacation rental business using the collective wisdom of the greater group: after all, how often do we as sole proprietors get stuck solely because we're trying to grow alone?

If you are an Inner Circle member, the full transcript from our meet-up is provided here.

Immediately following the Drake Hotel event on Friday, we all headed over to a larger event called the Vacation Rental Success Summit. It was hosted by the vacation rental industry's godmother, Heather Bayer, as the first step in uniting our fragmented industry. This event drew over 100 independents from around the world and managed to fantastically avoid any corporate sponsorship or spindoctory.

I made an effort to personally talk to every attendee for at least a few minutes: hearing their challenges, goals, life experiences...etc.

At both the Drake and the Summit, a concept I had been mulling over more and more lately -- a perspective that you don't always get to see when reading blog posts or interacting with people on email -- began to concretize:

And that is, what distinguishes independent vacation rental owners from the larger conglomerates (not to knock their success at all) is our purpose as it relates to vacation rentals.

Passion vs. Paycheck

Independent vacation rental owners really love hosting guests and becoming entrepreneurs!

While we still have plenty to learn in terms of running more efficient businesses, our passion is what comes first in our career choice. Not the money.

It's proven that people whose motivation is "self-authored" (doing what they love) always show more interest, passion, confidence, persistence, creativity, and performance than those who are motivated by rewards (doing what would make them money)[1. University of Rochester's Human Motivation Research Group:].

Think about how this advantage might apply to economic hard times.

Think about how ​this advantage might apply to ethical dilemmas and exit strategies.

Our Zone of Genius

The Vacation Rental Industry Future

None of this is to say that executives and employees at Airbnb and FlipKey and VRBO are not passionate. But for most of them, the passion in vacation rentals didn't come first, it came second (behind the need or desire to work and make money).

The bigger listing site folks would fall into what Gary Hendricks (in his book The Big Leap[2.The Big Leap by Gary Hendricks:]) calls the Zone of Excellence: areas that we excel in...things we do really well and are generously rewarded for.

But one step higher than the Zone of Excellence is Hendricks' Zone of Genius, in which individuals are thriving on every level. Individuals are not just successful in the Zone of Genius:  they are also fulfilled by doing what comes most naturally.

To me, the triumph of vacation rental independents over the big listing sites lies in our devotion to doing something we love, rather than just listening to conventional business logic or riding a profitable wave.

In Toronto, I met one new owner -- a retired beekeeper -- who is in the process of creating the world's first ecofriendly bee-friendly vacation rental, complete with a HoneyFlow[3. HoneyFlow: The World's First Beehive Technology:] beehive device (right) on tap.

I met another who is so passionate about hosting guests and so aware of all the stuff she doesn't know about running her luxury vacation rental, that she was offering two free nights to anyone who wanted to come and stay for the weekend to mentor her growth: relationships and learning, not dollars and cents.

My Big Take

What I learned from Toronto's group of independents and the reason I am confidently putting my money on the these folks moving forward, is that they keep doing what makes them happy without regard for how old they are, how skilled they may be, or what their competitors think. This is, in a lot of ways, the new face of the vacation rental industry moving forward.

It's surprisingly simple and admirable logic if you think about it.

And the best part, it doesn't depend on anyone's judgment but our own.

If I had the opportunity to meet you in Toronto, please use the comments area below to share your feelings on this notion and where you stand on the future vacation rentals...​


  1. Great post Matt! Independent VR owners have become the new “boutique vacation rental” dealing direct with owners will become more rare and will now be considered the new luxury! We have become our own niche in the business!

    1. So lovely to see you as always my friend! I’ve got your magnets being put up in our rentals as we speak!

  2. Thanks for this, Matt. I’m sorry I didn’t get into Toronto on time to get to the Drake and appreciate your link! The VRSS was awesome – one of the best conferences I’ve been to in 40 years and loved the passion of everyone there. Even people who were just starting out had something useful to contribute!

    1. It was so great to meet you too, Bonnie! Totally agree with you on the conference: learning is a two-way street and it’s pretty remarkable when even the most advanced folks are looking to learn from the so-called beginners. Been thinking a lot about your comment in the lobby after the presentation as well. Very appreciative that you noticed that subtle shift 🙂

  3. I agree Matt that passion has to come first. Without that your work is, well, just work. And, if it’s just work, your guests will feel it. That’s not the basis of a sustainable business! Note: something we’re also focusing on with our own business 🙂

    1. Amen to that! I think that’s something we’re ALL focusing on, both in business and in life. Lovely to see you and Jess as always. Talk this weekend.

    1. Thanks Tracy! Spoke with a few Florida owners who spoke highly of your management services. Congrats on running a word-of-mouth worthy business!

  4. “keep doing what makes them happy without regard for how old they are, how skilled they may be, or what their competitors think”
    I love this especially! The vacation rental owners I met at The Vacation Rental Summit this past weekend fall all over this spectrum, but they all had one thing in common – passion!
    This is the new face of the vacation rental industry and as we become more organized thanks to people like Matt we can help each other to fulfill our dreams.

    1. So agree with you here, Michele T! Loved your energy and enthusiasm. Looking forward to visiting you in Toronto again soon.

  5. Wow what a great event and so much fun. I met all the Movers and Shakers of the Vacation Rental World. Kudos to you all. Keep up the good work. I had tons of hugs and kisses from you all. I’ll support you any way I can – Go for it Guys!! Hugs and Kisses from Maria Rekrut from Niagara on the Lake, Ontario, Canada

    1. Oh Maria, meeting you was one of the highlights. For those who didn’t make it, Maria featured prominently in my presentation as someone who was using VRBO back when it first started (image attached). Her enthusiasm was totally infections. And I even got a signed copy of her book!

  6. I love the bee-themed rental! I know someone else who is doing something similar in Mexico and also farm-stay B and Bs and vrs are popping up all over the place. Guests can choose to interact as much or as little as they want with the farm managers and staff. Well, then there is the brand new cannabis-friendly vacation rentals in states where that is legal, now. They even have their own listing site called “Bud & Breakfast.”

    So, yes, VR owners are innovating all over the place. With regards to all that is going on in the industry with the listing sites, etc., I just keep thinking of the old Bruce Lee quote,

    “Be like water making its way through cracks. Do not be assertive, but
    adjust to the object, and you shall find a way around or through it. If
    nothing within you stays rigid, outward things will disclose themselves.
    Empty your mind, be formless. Shapeless, like water. If you put water
    into a cup, it becomes the cup. You put water into a bottle and it
    becomes the bottle. You put it in a teapot, it becomes the teapot. Now,
    water can flow or it can crash. Be water, my friend.”

    1. Love this quote, Dawn. It was awesome to see how many passions led to businesses at this event. Even if inquiries are down or the calendar doesn’t fill 100% we’re still doing what we love!

  7. Enjoyed meeting everyone and the continued encouragement to find your purpose. Sometimes bigger isn’t better. I constantly evaluate my opportunities to “do it better” in marketing and running our rental. I’m in favor of continuous improvement, but also making sure that each new thing I take on (website, social media advertising, video, etc) is consistent with my purpose. If I spend all my waking hours developing my marketing, I might miss that important time from the video: siesta, time with family friends, or I might beat myself up for not getting far enough fast enough. So, I am ambitiously, but gently taking my success one step at a time, to always check against my purpose not just for the rental, but overall as a human, wife, friend, climber, dog mom, etc. Love the concept by @bobtheteacher of NOT starfishing its the same idea.

    1. Well said, Holly! You speak my language: small steps without loosing sight of the big picture.

    2. Right on, Holly! Hanging with you was wonderful as always. And it’s so cool to see how you’ve taken to mentoring other folks so quickly: your analytical style definitely helps people divide black and white, then focus on moving forward. It was great to meet Jeff too: let’s fix that national park system!

    3. Holly, thank you for all of your assistance. As Matt pointed out, your mentoring is so valuable and certainly helped me move forward through an issue!

  8. Heather, Mike & Matt: Thank you, thank you, thank you! It was pure joy meeting so many folks from the Inner Circle. It felt like connecting with old friends. And I am totally pumped up to move along the LSI path. One of my big take-aways already set into motion: Finding an ‘accountability partner’ for weekly meetings to go over set goals and accomplishments. Or as Matt Ward said: “Attitude + Action = Results”.

    1. So great to meet you too, Sibylle. I very much enjoyed our conversation Saturday night. Looking forward to hearing how your trip goes 🙂

  9. We had a amazing time meeting everyone. VRSS felt so much different from any other VR event I have been to: this is a group of highly entrepreneurial, smart, innovative, independent thinkers. I feel privileged to have been able to join this first edition and one day we’ll all reminisce that we were there, at the first Summit- thank you very much Mike, Heather and Matt!

  10. It was a really great weekend to meet like minded VR Owners and managers. It truly is a passion and the first attendees and presenters were an awesome example. Thank you Matt, for without your blog I wouldn’t have found it. Thank you Heather and Mike for being believing in your passion enough to take on the daunting task of the Vacation Rental Success Summit. I am very excited to be on this journey with all of you.

  11. “The only way to do great work is to love what you do” Steve Jobs
    So very glad to have had the opportunity to meet so many great and passionate people at the Inner Circle Meet Up and later the Vacation Rental Success Summit in Toronto. I took away so much great information and actionable plans, that weekend was worth its weight in gold. Thanks to everyone for sharing their experiences!

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