75 Minutes of Vacation Rental Wisdom in New York City

When I travel to new destinations, I like to take the opportunity to host private gatherings of vacation rental pioneers. Because our industry is so new and most of us are innovators in our respective markets, these meet-ups end up being one part networking, and two parts focused learning in which we can solve actual problems and build better businesses. Last month in Austin, this month in New York City!

My visit to New York City began at The Metropolitan Club for the John P. McNulty Prize Ceremony on behalf of our foundation Esperanza Social Venture Club. Unfortunately, we did not win the grand prize (it went to this phenomenal woman) but the experience gave me a window into the world of today's great thinkers...

Apart from being with my most incredible Esperanza family (right) I got to meet and have dinner with Linda E. Johnson (President of Brooklyn Public Library), Dele Olojede (first African-born winner of the Pulitzer Prize), Andrew Zaloumis (winner of the 2015 WWF Living Planet Award), and Aprile Age (Director of the McNulty Foundation). To say that I was taking comprehensive mental notes the entire evening -- no, that I was just in sheer awe of the positive vibes and thought leadership -- would be an understatement!

But not to be outdone by the McNulty prize was our VRMB Inner Circle Meet-up the following evening. We gathered at Voyager, a private club for travel start-ups with big windows, giant board rooms, and a live kegerator (my favorite part). The Voyager club is backed by Sam S. Jain (the founder of Cheapoair) and is essentially a hub for startups, corporate partners, and VCs in the world of travel.

After two dynamic hours of meeting and then two more hours of cocktails and french fries, here are the five big things I learned:

1. Independents Are Beginning To Look The Part

Independent vacation rental properties reflect maybe the first ever of its kind to the supply side of the hospitality industry: inventory that is not owned by a privileged few, but by us "common folk" who are beginning to compete, on a guest-by-guest basis, with some of the greatest hospitality brands in the world.

As the big venture capitalists and corporations try to figure out what's going through the independent's heads, I am always ultra proud to see us getting the respect we deserve: a perfect example was the location of our meet-up: this cutting edge space in downtown Manhattan made for travel start-ups. Speaking afterwards with Voyager's mastermind Managing Director, Andrew Stein, we both agreed that despite the unorthodox backgrounds, this movement of secret hoteliers is quietly taking the travel world by storm and it's kind of cool to see them doing so in style.

2. Lack Of Time is Lack Of Focus

"Give me six hours to chop down a tree, and I will spend the first four sharpening the axe." I am always reminded of this quote by Abraham Lincoln when we host IC meet-ups because we ask everyone to bring one very specific challenge, question, or problem they are facing in their business and to articulate that question to the group -- hot seat style -- in 30 seconds or less. This forces us to get really thoughtful about our needs...in fact, one member in NYC told me she had been iterating her question for days ahead of time, so to take full advantage of the wisdom of the group.

In the same way that better questions lead to better answers, we discovered in NYC that sharper goals translate to a greater likelihood of reaching them. There's no quicker way to drift than to overlook the process of defining your goals. Spend two parts sharpening your axe and one part actually chopping the tree.

3. The Power of Proximity

Too often we try to solve our vacation rental industry problems either in private or from a distance. The owner hitting her head against the wall as she tries to update new photos across five different listing site platforms. The property manager dreaming up ways to attract more property owners who live out of state. The start-up co-founders in the boardroom running in circles trying to define the true pain points of their clients...

But from our IC meet-up in NYC, I was reminded the power of proximity: getting close to your problems, your clients, your adversaries, your competition in order to understand them better. This can be an uncomfortable thing to do as we have found with the gangs in Panama -- getting up close and personal with different stakeholders standing in the way of your collective success. But in terms of truly holistic solutions, there's simply no other way forward.

4. The Industry's Most Precious Emotion

Like in any developing market, making quick money is easy in the vacation rental industry today (well, at least comparatively easier than it will be moving forward). But what's more difficult is creating a business in our niche that can stand the test of time. To do this, we need to focus less on the short term and more on the long play. And to do this, we need to invest in creating prototypes: guests into whom we pour disproportionate amounts of time and money with the end goal of replication.

My hot seat question for the NYC IC group was, what words describe the most influential businesses that you trust in vacation rentals today? The answers ranged: ethical, courteous, professional, authentic, high-touch. But the most powerful descriptor was empathy. We are attracted to vacation rental businesses who are empathetic: or as one Inner Circle member put it, "companies that get us." If you look at the future through this lens, being empathetic and truly caring about a small handful of individual clients' long-term happiness emerges as something of a Holy Grail.

5. Passion as the Great Equalizer

Running a successful vacation rental business is hard work. There will be seasons in which you break even or lose money. There will be adversity that urges you to quit and close up shop. There will be day-to-day stresses and cockamamie guests that can really get under your skin...

But I learned in NYC -- a place where big money and large corporations rule -- that perhaps the greatest equalizer in our emerging industry is not head but heart. If our heart is first in the vacation rental game, and we have chosen this as a lifestyle business, we have the ability to outlast competitors who are solely driven by profit or fame. This is the independent's secret weapon against the large listing sites: relinquish it and you're fighting fire with fire (and you'll probably lose).

​Conclusion

If you have attended one of our private events, you know how fun and informative they are. I always come away feeling reassured, re-validated, and reinvigorated to continue down the path we have chosen. 

Meeting our members from New York City also taught me how Inner Circle members deal with different geographical challenges. So don't be afraid to get together with your local colleagues and tackle your regional challenges together.

I look forward to hearing feedback below from attendees and those who have thoughts on these ideas...

About the Author Matt Landau

Matt Landau is the Founder of the Vacation Rental Marketing Blog and the Inner Circle, two online resources dedicated to helping vacation rental owners and managers generate more bookings. Google+ | More Posts (230)

  • Matt. What a great evening! Thank you so much for inviting us. I’m impressed with the unbelievable care and thought your members put into their businesses.

    Cheers,
    Evan Hammer
    CEO, Smart Host

    • Matt Landau

      Amen to that amigo. Always so cool to hear how you guys are growing. So appreciative that it was you who came and not Nick 😉

  • Amy Grant

    Inspiring as always:)

    • Matt Landau

      Missed you here!!!

  • Thank UU Matt for all UU do!

    • Matt Landau

      Thank YOU Tracy for being YOU!

  • Melissa

    What an inspiring evening! It was so wonderful to have met IC members in person. Thank you for this amazing meet up opportunity!

    • Matt Landau

      Melissa, it was SOOO lovely to finally meet you and Rob. I think you have earned the new title of IC watchdog. Can you come to all events to make sure our participants have the approved usernames on their nametags?

  • Evelyn

    Matt- It’s such a pleasure to be part of not only your inner circle but to be part of last night’s meet-up was just fantastic. Everyone had great ideas and solutions for all the questions.

    Until next time,

    Evelyn- The Hosting Journey

    • Matt Landau

      Evelyn it was SO COOL to meet you too!!! Maybe next time we need to choose an after-party place that’s not as loud as the thunderdome!

  • Jamaicavilla

    It was such a pleasure to finally meet Matt in person. I would also like to say thank you to everyone for sharing their ideas and thoughts. I’ve learnt a lot.

    • Matt Landau

      Oh Cavel, so incredible to meet you too. You and I have been on this journey together from the very beginning. It’s just such an honor and a pleasure to watch your business grow. Thank you for being such a VR ambassador!

  • John Klein

    Matt, Thanks very much for hosting another inspiring get together. This was my 2nd IC meet up and it is amazing how powerful it is when you put like-minded and like-enthusiastic people together! It was a pleasure to meet everyone there. Til next time!

    John K

    • Matt Landau

      JK, as always, a total pleasure to see you. At the rate that our meet-ups are improving, we’re gonna need a bigger boat! Wouldn’t ya say!?

      • John K

        Aye, Aye Captain!

  • Awesome to have you in NYC Matt…thanks for a great evening 🙂 Nothing better than being in a room full of business savvy rock stars at the forefront of the vacation rental industry. Amazing insights & candid advice. I was honored to be there & look forward to many more IC events!

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