VRS173 – The Airbnb Perspective With Andrea Diamond

I’m embarrassed that it was only two years ago I was questioning the relevance of Airbnb, and being remarkably short-sighted on the movement of a platform that has since come to dominate the vacation rental space.

I’ve just read ‘The Airbnb Story’ by Leigh Gallagher and enjoyed it immensely, learning about how Brian Chesky et al, got the company off the ground, more by luck than design. It was never expected to be the behemoth it’s become, and the story of investors who shied away from dropping their money into the ‘crazy idea’ has similarities to those publishers who rejected the original JK Rowling manuscript.

Airbnb are the platinum sponsors of the Vacation Rental Success Summit this year

In today’s episode, I talk to Andrea Diamond, who leads Airbnb regional operations in Central & Eastern Canada.

We also announce the final keynote speaker for VRSS17…so listen to the end!

We discussed:

  • Andrea’s journey from being a host in Tel Aviv to regional manager for Airbnb Canada
  • Why rural rentals are not a great change in the Airbnb model
  • The importance of the host/guest relationship and how the platform encourages it
  • Why reviews are so important to the success of a host
  • Instant booking and why she wishes it was called something else
  • The Trips concept and how they enhance the guest experience

The Airbnb Story

Andrea’s LinkedIn Profile

VRS172 – 10 Reasons I Will Not Be Inquiring About Your Vacation Rental Property

Do you ever wonder if your listing is attracting people to inquire about your property? Perhaps you see the stats that show how many have looked at it…but you didn’t get the inquiries or bookings that would make that number seem realistic.

Could it be something in your listing that is moving them onto the next place?

I started thinking about this recently when looking for places to stay on some upcoming trips, and got curious about my own thought patterns as I browsed the hundreds (and in some cases, thousands) of potential homes.

This episode explores the mistakes owners make with their listings, and how a little adjustment could bring more visitors to your own site, or at least connecting with you. And often, that’s all you need to get the conversion process rolling.

I uncovered ten reasons I won’t be inquiring about a property. They include unattractive feature photos that don’t grab attention; boring headlines; grainy and badly lit photos; uncomfortable looking beds and dull kitchens, and defensive responses to negative reviews.

Every one of these can be fixed.

In this episode I talk about:

• Why the Orlando villas with an exterior photo of the garage are a turn-off
• What you should remove from your headline
• The importance of professional photos
• How your guests perceive comfort
• Blah blah text and the way to resolve it
• Why I want to know about you and why you love the property
• The one complaint guaranteed to cause a click to the next listing
• Speed of response and calendar updates make a difference
• Why being defensive has repercussions
• Updating calendars and speed of response

YourWelcome – A Digital Vacation Rental Welcome Book

We have talked at length, both in blog posts and on the podcast, about the importance of welcoming your guests to your property and how that first impression is invaluable to the outcome of a happy guest.

One of our most popular blog posts (The Vacation Rental Welcome Book) covers the in’s and out of preparing the best possible physical ‘book’ or binder to give your guests all the information they could need about the property or the area. The biggest draw back of this method is the possibility of damage and also the inability to do immediate updates without having to disturb the guests or traveling to your property.

In this amazing age of cloud computing some very smart people over at ‘YourWelcome‘ have developed the first tablet designed specifically for providing the perfect welcome book in a digital format with remote updating capability.

Check out the video above from Gary Miller (Vacation Rental Formula Community Manager) and see what you think.

You can also find some great articles here:

– YourWelcome – The Bespoke Tablet that Lets Airbnb & Short Term Let Hosts Offer Guests A More Personalised Service

Learnairbnb.com – Airbnb Tablets Help Improve Your Guest Experience

As a reader of CottageBlogger we have also been able to secure you a 10% discount off your subscription to the YourWelcome service.



Please comment below and let us know your thoughts about using a digital welcome book.

VRS171 – Taking Great Vacation Rental Photos with Amy Greener

Getting great photos of your property is undeniably the best start to a successful vacation rental listing. You can have all the bells and whistles in terms of amenities, but if the photos don’t inspire your guests to book, you’ve lost their interest before they even get to the bit about all the flat screen TVs and stainless steel appliances.

My guest on Episode 171 knows more than most how important that is. Amy Greener is an owner of five properties, and manages another six on behalf of other owners, in the Smoky Mountains area around Gatlinburg and Pigeon Forge. She is also a professional vacation rental photographer.

It’s a highly competitive market so I wanted to find out how Amy differentiates her small company and attracts guests to book her properties, while managing her successful photographic business as well.

I had an ulterior motive in my questions to Amy as I’m nearing the end of the refurbishment of Kingfisher Cottage and, as soon as the furniture is in place, will be doing a photo shoot of my own. Although I’m getting better at taking pictures….here’s a couple I really like from a recent shoot….I know I can do so much better at staging, setting up the shot, and editing.

Amy talked me through a range of tips and ideas to improve my skills and explained a few ways of making this whole process more systemized and effective.

We talked about:

  • Her journey from a single property to being a property manager
  • How learning from mistakes along the way has generated a more streamlined company
  • The approach she takes to competition and being different & running lean
  • The best time of day to take photographs
  • How it’s OK to use your iPhone
  • Why you should overshoot and get at least 3 angles of each room
  • The importance of removing distractions before taking the photo
  • How best to take a bathroom picture
  • When to do close-ups
  • Why less is more in most photo staging
  • Taking time for attention to detail and the little things that can get missed
  • Shooting from the belt and not looking down
  • Amy’s tips for anyone wanting to start up a vacation rental business


Blue Mist Cabins

Amy Greener Photography

VRS170 – Practical Vacation Rental Investment with Michael Hamilton

My guest today took his interest and knowledge of real estate investment and has turned it into a vacation rental business. With three properties currently listed on Airbnb & VRBO Michael Hamilton was about to fly off to North Carolina to close on the fourth, when I was able to talk to him from his San Diego home.

Michael emailed me at the end of last year asking for some feedback on his listing text after he’d studied my ebook, Hypnotic Language for Vacation Rental Listings and Emails. I was interested in his choice of properties and by the way he was achieving such great results as evidenced by the Airbnb reviews.

He shares his strategies for purchasing new properties which includes his passion for surfing and the outdoors, balancing that against the economic factors of selecting a location.

This is a fascinating glimpse into the world of a practical vacation rental investor – one who has minimal emotional participation in the rental potential of a property, but rather sees it as a working entity.

In this interview Michael talks about:

  • How his love of surfing drew him to the North Carolina coastal area
  • The importance of growth indicators to location choice
  • The Airbnb impact on bookings
  • Creating transparency in listings
  • What the About Us page does to increase interest
  • Why he prefers a systems dependent business for managing multiple properties
  • His 3 tips for anyone starting a similar business

Links mentioned in this episode:

Vacation Rental Success Summit

Fortune Builders

Bigger Pockets

Chill Beach and Surf Bungalow

Magical Bungalow OBX

Chill Beach and Surf Pad – San Diego

The E-Myth Real Estate Investor

VRS169 – Don’t Wear Flip Flops in the Jungle & Other Things Your Vacation Rental Guests Need to Know

What could be better than exchanging a cold and snowy Ontario for 10 days in sunny Belize? Or Eleuthera, or Exuma, or Costa Rica, or Maui?

For the past 7 years, we’ve taken a break in winter to enjoy the sunny south, and stayed in a different vacation rental every time. It’s been great, not just for the obvious warmth and tropical benefits, but to get that learning experience that comes from being a guest.

I know I’ve harped on about this before, and will do so again and again. So, no apologies for revisiting this topic, because the only way you’ll create the perfect guest experience is to be a guest yourself.

And not in your own place.

So, here I am back home reflecting on my vacation and thinking about how the reality matched up with what we were promised. What comes to mind is the information provided before we went, what was there at each place when we arrived, and how the owners shared their knowledge during our stay.

I would say I’m pretty independent as far as travel planning is concerned. I can Google along with everyone else, but I still welcome information that comes from owners who have so much more knowledge of the local area.

Owners or managers are the information sources that guests need to ensure a great stay. Withholding that information can make the difference between frustration and irritation and a well-executed and enjoyable vacation.

As a rental agency here in Canada we produce a comprehensive guide for International visitors. This covers things like LCBO/Beer stores (cannot buy booze in a supermarket); rules of the road – four-way junctions, turning right on a red light, stopping for school buses. We also help out our guests from the city who are planning on visiting our country areas, because they will find big differences in the way of living.

So what do you do to prepare your guests for their stay? How much do you share? How far do you go to help them plan?

In this episode I’m exploring what guests want in the way of information before they leave on vacation, while they are there, and what you might think of providing.

I talk about:

• Why you should not expect your guests to be independent planners
• The 7 essential pieces of information to help your guests plan their vacation
• The importance of customs and immigration information
• Why I don’t want to read your guest book
• How you can prevent guests getting into trouble
• How your local knowledge can deliver 5 star reviews
• 3 simple ways to deliver information to your guests ( and get them on your web site)

VRS168 – The French Connection with Vacation Rentals in Nice and Paris

Many vacation rental owners manage their properties from a distance but most have just one, or a few in one location. Ralph Morehouse owns an apartment in Paris, one in Nice, and manages three others. All from his home base in Houston, Texas, which goes to show you can do this business from anywhere as long as you have the systems in place.

I first met Ralph and his wife Karen, in New Orleans a few years ago. Although Ralph has been in the US for quite a few years, his UK accent is unmistakable and we explored the journey that has taken him from roots in the north of England to Texas, via Paris.

With recent terrorist attacks in both locations, we discussed how these had impacted bookings and what Ralph does to reassure rental guests. He also talks about the challenges of acquiring and retaining good staff in both locations.

Finally, Ralph shared the resources he uses to successfully manage the properties.

Ralph talked about:

  • The most challenging aspects of long-distance property management
  • How the terrorist attacks in Nice and Paris impacted the business
  • Managing payments in multiple currencies and the platform that makes this easy
  • Co-ordinating enquiries and reservations via multiple systems
  • The #1 thing he would do differently if he bought another property

Links in this episode:

Dawn Shears of Red Spiral Hand


Booking Sync

VRS167 – A Year In The Making with Sherene McLellan

It was a long-time goal for Utah resident, Sherene and her husband John. One day they would buy a vacation rental property and from the get-go they wanted it to be a professional business. No short cuts for these guys.

They looked at different places in their beautiful state, and finally settled on Kanab – a small town in the heart of Canyon country. Although tourism had come big time to Moab, it was only when Microsoft chose a local landmark as their backdrop to Windows, that little Kanab was propelled onto the international stage, and Sherene and John found their location.

And so Western Star Bungalow was born. From base beginnings, they refurbished the property with their target guests in mind and created a gorgeous old-movie themed home, to the extent that even their Welcome Book has been prepared in the guise of a screenplay!

Sherene has been on a quest for learning that has resulted in enticing listings with great text and appealing photos that have already yielded 24 bookings in a few short months. And, at the time we spoke she was just days away from her first guests arriving.

In this episode Sherene shares how they decided upon a property that needed renovation instead of going for a turnkey condo, which she says would have been so much easier. But not as much fun.

She also talks about:

  • The history of Kanab and its surroundings & why it makes a great destination
  • Why she chose to be pet-friendly
  • Their choice of creating two en-suite master bedrooms
  • Bathroom beauty and how an old log became a bathroom vanity
  • The most challenging aspects of starting up a vacation rental business
  • Why finding a caretaker was more important than finding the property
  • The tools she is using to manage the house from a distance
  • The best piece of advice she was given by another VR professional
  • Which platform has brought nearly 70% of the early bookings & why that was a surprise

And much more…..

Airbnb listing

VRBO listing

The Wave

Best Friends

Tyann’s book Creating Killer Vacation Rental Photos

The Hosting Journey


VRS166 – Vacation Rental Travels with Beth Caro Carson

Editor of the VR industry’s only online magazine for travellers, Beth Carson is a seasoned traveler (45 countries stamped in her passport!) and knows travel from both sides of the check in desk. Beth dishes about the ins and outs of running a magazine, her gift to vacation rental owners, and delves into surviving one of the world’s most powerful hurricane’s with 4 guests in her house in Fiji, collaborating with her neighbor on a Go Fund Me Campaign, and why HomeAway’s changes can be viewed in a positive light. She also shared some of the secrets of taking a client’s 2 condos from a 6% occupancy to 78% occupancy in just 2 months. Listen up for a fast paced romp with an industry expert.

Beth is one very busy person so I was happy to track her down in Mexico for a great conversation about her busy year in 2016, and what she has planned for this year.

I first interviewed Beth in July of 2014 on VRS033 and we talked about her Fiji property and how she decided to get into the business of vacation rentals in the first place, so we recap on that as well as her move into condo management.

The online publication Vacation Rental Travels is a must-subscribe for everyone in the industry as it’s the only magazine devoted solely to vacation rentals worldwide, sharing the best of the best with the travelling public. As Beth points out however, a property doesn’t have to be $20K per week to be featured – it just has to have that special ‘something’ that makes it unique and desired. In fact, if you come to VRSS, you’ll have the opportunity to talk to Beth about your place and talk about how to get it featured.

From discussing Vacation Rental Travels to the crowd-funding campaign she launched to help neighbours in the badly damaged areas of Fiji, to explaining why you should attend events like VR Mastered in Mexico, and VRSS in Toronto, this is a content packed episode not to be missed.

Beth shares:

  • The reason she ‘felt like Oprah in the aftermath of a cyclone that devasted Fiji.’
  • How she moved a condo owners occupancy from 6% – 70% in five months.
  • Her secret to customer service.
  • The importance of sharing Western traveller expectations with local staff.
  • Why she is an advocate for Book It Now.
  • How she wanted to ‘legitimise the industry’ by attracting travel writers to experience it.
  • The help she got from Matt Landau & how that made a difference.
  • The value of one-to-one training and expert help.
  • Thoughts on buying property and how to get it right.

Links mentioned in this episode

Pathfinder International

International Living

Starfish Blue

VR Mastered

Vacation Rental Success Summit

Vacation Rental Travels

VRS165 – Hard Lessons Learned with Matt Landau

When Matt Landau closed on a deal he couldn’t ignore and became the proud owner of what is now Los Cuatros Tulipanes in Casco Viejo, Panama, he didn’t appreciate that over the next few years he would earn the equivalent of an MBA in vacation rentals.

He learned a lot about the neighbourhood, the people it would attract – and those that wouldn’t like it, the staff he needed to employ, and the right way to market.

But every lesson was learned by trial and error and as he puts it…the hard way.

When I emigrated from the UK to Canada and embarked on a new career as a property manager, with no prior knowledge of what that entailed, it too was a time of hit or miss experimentation.

Some things worked and others didn’t. And if I knew then what I know now, I’d have saved time, money and a lot of stress.

So, Matt and I have a lot in common with our mistakes and successes, and now we both share what we learned the hard way in our respective blogs and training.

In this episode we touch on some of the primary things we learned at the beginning of our journeys, and how just about everyone can benefit from the mistakes we made.

We share:

  • The critical research that is necessary when selecting a realtor, and what questions you need to ask them.
  • The importance of documenting every system and every process, and the long-term impact that can result from only one person having ‘the knowledge’.
  • Why marketing should fit the traveller demographic – there’s no valet service in Casco Viejo!
  • Why unique destinations should never be open to non-educated (instant) bookings.
  • The difference between what guests think they will experience and what they might get.
  • The importance of guest education to bridge the expectation gap
  • How much a negative review costs over the course of time and why that should impact your choices on complaint handling.
  • The perils of renting space on someone else’s land and not owning your reviews.
  • Why you should only partner carefully and thoughtfully with companies that share your mission and align with your values.
  • The ‘Help don’t Sell’ philosophy that should be the cornerstone of your business.


Sites we mentioned in this episode:

7 Reasons you will not love Casco Viejo

Tools of Titans – Tim Ferris

10 Mistakes that VR owners make

A Complaint is a Gift

Upwork for outsourcing

Ross Robertson Insurance

Vacation Rental Success Summit

Los Cuatros Tulipanes