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EP173: Short Stay Rental Pioneer Shares Insights from Two Decades of Hosting Experience

Branding is an aspect of the short-term rental game that many hosts overlook. And when you’re first getting started, you may not know what sets your listing apart from others in the area. But once you’ve had a few guests, it is possible to use their feedback to identify the most attractive aspects of your property and strategically incorporate that information into your listing. Today’s guest reveals how he got clear on his brand — and a host of other lessons he learned in his 20-year career in the vacation rental space!

Jack Pope got into hosting to supplement his income as a teacher. He converted an extra space in his home on the Sunshine Coast of western Canada into a suite, but zoning didn’t allow for long-term rentals. So Jack got connected with a group of vacation rental entrepreneurs, eventually becoming president of the largest B&B association in western Canada.

An early adopter of technology in the short-term rental space, Jack made use of online platforms as they became available. Airbnb has become a valuable tool in his business, and 70% of his bookings now come from the site. He has been a Superhost for seven consecutive quarters, and today he shares his extensive hospitality expertise with the Get Paid for Your Pad audience, explaining how he marketed Coracle Cove in the days before online booking, how he achieves a crazy-high return rate on guest reviews, and how he has automated guest communication. Listen in for his advice around providing a seamless check-in and branding your listing to attract the right guests!

Topics Covered

How hosting was different 20 years ago

  • Most bookings done by phone
  • Only 20% of bookings made online
  • Local portal generated most referrals
  • Brochures, self-promotion as marketing tools

How Jack marketed Coracle Cove early on

  • Connected with travel writer, spread in Vancouver Sun
  • Hosted writer from Lonely Planet

The platforms Jack utilizes to promote his vacation rental

How Jack achieves a 91% return rate on guest reviews

  • Promise to write positive review for guest at checkout
  • Send thank you message through Airbnb soon after checkout
  • Review guest immediately after email received

How Jack used guest reviews to brand his listing

  • Categorized guest comments in TripAdvisor reviews
  • Modified listing title based on unique aspects
  • Pulled quotes to use as photo captions

The four automated messages Jack schedules through Aviva IQ

  • Confirmation and welcome with short video (10 min after booking)
  • Detailed directions and link to blog (week prior to arrival)
  • Link to video and blog (morning of arrival)
  • Thank you and review request (soon after checkout)

The importance of specific, accurate directions

  • Positive reviews are essential
  • Seamless check-in vital part guest experience

Jack and Jasper’s advice around delivering a seamless check-in

  • Follow directions yourself to confirm clarity
  • Film yourself en route to Airbnb
  • Provide pictures of entry door, etc.
  • Set up meeting place if property is difficult to find
  • Stay in contact with guests through messaging platform

Connect with Jack

Coracle Cove Website

Jack’s Airbnb Listing





Aviva IQ

Hostfully Partnership

Hostfully Host Program

Connect with Jasper

Email: jasper@getpaidforyourpad.com

Twitter: @GetPaidForUrPad

Instagram: @GetPaidForYourPad 

Facebook: www.facebook.com/getpaidforyourpad

This episode is sponsored by Hostfully.com where you can create a custom digital guidebook for your guests!

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Complete Transcript for Get Paid for Your Pad Episode 173

Jasper: Welcome to Get Paid for Your Pad, a definitive show on Airbnb hosting, featuring the best advice on how to maximize profits from your Airbnb listing as well as real life experiences from Airbnb hosts all over the world. Welcome.

AD: This episode is brought to you by Hostfully. A company that helps you make beautiful guide books for your listing. Especially for Get Paid for Your Pad listeners, get two free months of their premium version. For more details, visit Hostfully.com/Pad

Jasper: Hello Everybody, welcome to another episode of Get Paid for Your Pad. Today we’re very excited to be welcoming on the show Jack Pope, who has been a host for over 20 years and he’s the former president of Canada’s largest Bnb Association at the time. He’s always been an early adopter of new technology of the home sharing space and has stayed at over 25 Airbnbs himself during his travels. Jack, welcome to the show.

Jack Pope: Thank you Jasper, it’s good to be with you this morning. I’ve been trying to keep up with your travels, I understand you’re in New York.

Jasper: That’s correct. I just arrived a few days ago. It’s been a fun time so far. It’s always fun to be in the big apple.

Jack: Absolutely.

Jasper: So, Jack. We talked about your story, I’m excited to get into the details. You have a host of experience when it comes to hospitality. You’re a super host on Airbnb for seven quarters, that’s quite the achievement. So, let’s get started. Can you please share how you got involved in the Bnb business?

Jack: Well, my former career was as a teacher, so in the summer I was looking for ways to supplement income. I got into building houses, building our own houses. The last house we built which is a beautiful location right on the ocean, when we started building it, we were going to have an extra space on the bottom floor. I converted that into a suite and we though, okay, what are we going to do with it, the zoning didn’t allow us to rent out on a long-term basis, but it did allow us to operate a bed and breakfast.  So, we sort of stumbled into it, but in the process, I connected with a group of like-minded individuals on the sunshine coast who were active in the bed and breakfast industry and it kind of grew from there and I got very involved. Eventually, I became its president and we were able to do some amazing, cutting edge things in 2002, 2003 we won an award for technology and tourism when we developed an availability matrix. That’s something we all take for granted today when we go and look at a listing. You can see what dates are available and which are not. You can imagine what it would be like without such a tool. You’re playing telephone tag back and forth trying to nail down a booking with somebody, so we eventually went on to build the technology where someone could book directly online. Which is the Airbnb instant book model. It’s been a great ride. I’ve always been interested in learning things. I found there was definitely a pay-off to learning how to run the Airbnb business. I’ve been active in new things. I retired from teaching in 2005 because I could see the potential for my own business. Since then, I’ve increased my bookings by 80 percent, but actually managed to increase my revenue by over 150 percent. I guess I’m ab it of a pioneer in the industry. I’ve ridden this roller coaster of technology and coming to a platform like Airbnb which I think has everything that I’ve always wanted to use but on one platform, it’s just been a great tool for my own business.

Jasper: Can you talk a bit more about what it was like to host 20 years ago? Did people even really use the internet back then?

Jack: Not really. Maybe 20 percent of my bookings would come via some website and it was always interesting. You would take a booking over the phone, at the end you’d say, “how did you hear about us?” and at the end they’d say “well, I found you on the internet.” So, that didn’t really mean much because I was trying out various listing platforms. There was a local portal here called Big Pacific advertised on the internet, you could get the minimal listing on it. I found I was getting a lot of referral from that portal. Usually Google Analytics you can tell where your traffic is coming from. Mostly it was telephone content and brochures and just, getting out and trying to promote yourself as much as possible. I was very lucky early in the game where I met a travel writer at a conference and she very generously wrote up a beautiful, a whole page spread, in the Vancouver Sun, about our place. That seemed to set things in motion. I hosted a writer from Lonely Planet and got into the Lonely Planet Guide. There were a whole variety of things you would do to try and get yourself out there. Once the listing platforms came a long, it made things a lot easier. I’d say right now, about 70 percent of my bookings are coming from Airbnb. So much so, that I have my own website and I have a merchant account so I can take credit cards. So much so, that I was getting too many bookings from Airbnb and not enough from my own website that I had to change merchant account providers. It’s been a very interesting story. It’s just an incredible platform. My bookings in the last two years on Airbnb have gone from maybe 5-10 percent to now 70 percent.

Jasper: Are you using any other platforms aside from Airbnb?

Jack: Well, I’ve got my own website, which I’ve had for about 15 years. I’m on Flip Key, of course, it’s owned by Trip Advisor. Trip Advisor really was another great tool that I use probably five, six years ago, I did a lot of things to ensure that my guests would write reviews. Trip Advisor probably about ten percent will write reviews. I got that figure up to about 30 percent by using a variety of strategies. I’m on HomeAway. I’m on the Local tourism sites, Sunshine Coast tourism. I don’t want to confine myself to just one portal. It’s the old adage of putting eggs into one basket.

Jasper: What are some of these strategies you mentioned to get people to leave a review?

Jack: Well, I’ll give you an example. Yesterday I had a young couple checking out. I always try to engage with my guests. Make sure I’m providing them with lots of information. As they were leaving, they knocked on the door to say goodbye and I said, “have you used Airbnb before?” They said no. I said, well, I’ll be sure to write you a good review. I always relay a story of when I travel through New England, some of our hosts were single women, so I tell them hosts like to know about who is coming. I say, okay, I’ll write you a review. I hope you’ll write one about us. Then, I guess, about ten, fifteen minutes after they’d driven out the driveway, I know when they go to the ferry they’ll be waiting in line, so I sent them a message using Airbnb message service saying thanks for saying with me, as soon as I got the email from Airbnb saying “how was so and so as a guest,” I immediately leave them a review. All of these things are reminding the guest that just checked out “hey I’ve written a nice review, I hope you do the same.” I’m probably getting, oh, I think when I last looked at it, the metrics was 91 percent return rate on guests writing reviews.

Jasper: That’s a very high percentage for sure. You’ve also mentioned you use reviews to give you inspiration on how to grant your listing. Can you talk about that?

Jack: I’m actually using my reviews in a couple ways now. A couple years ago I went through a branding exercise where we look at Trip Advisor reviews to create a brand. I was taking it online from Cornell University. I thought, why don’t I do that for myself. I went through all my trip advisor reviews form the last year or year and a half, and I tried to categorize things that my guests were commenting on. At the end of the exercise, I had a very clear picture of what my guests were seeing when they stayed with me. That’s obviously my brand. Up until that point, I was just branding myself as this water-front bed and breakfast, but there were about a dozen of us. I knew them all. We were all the same. But it wasn’t until I saw my brand through the eyes of my customers that it crystalized what it was that I could focus on. The beauty of that, I changed my website up ab it, I had this beautiful quote from Lonely Planet about my suite being located just steps away from the glistening brine, this beautiful, lyrical passage. So, I moved that quote right up to the top of my website. So that would be the first thing my guests would see. The beauty of that is that once you’re very clear on what your brand is, you’re going to attract people who are interested in that brand. It’s a self-fulfilling prophecy. If you’re providing a brand people are looking for, they’re going to talk about it. The brand gets reinforced through reviews. The other thing I’ve done is taken quotes from my reviews and used those as captions in my photos so instead of saying “king sized bed” in the bedroom, I have a quote saying, “it was wonderful to lie in this large bed listening to the waves lapping against the shore.”

Jasper: I’m looking at some of the quotes, I think it’s a great idea. For sure. There’s no better way to describe the guest experience than to let the guest speak for themselves. I think it’s a great idea. It’s very inspirational for other Airbnb hosts. I like that he talks about the branding. I think it’s something hosts overlook. Because what’s your brand? You don’t really know. You create a listing and see how it goes and you might not be aware of the most attractive aspects of your listing. You can use that in so many places. Once you know what people appreciate most about your place, you can put a picture of that first. You can highlight it. There’s a lot of places you can use that information. I think every Airbnb should use this at some point, once you have 5-10 reviews, see what people say.

Jack: That’s why I chose the title for my listing as Oceanside Hot Tub + Sunsets =Bliss. Because my guests talk about this ocean side hot tub and we’ve got lots of great sunset pictures. In essence, that’s my brand. I did a quirky thing where I did it in all lowercase lettering to make it unusual and make it stand out.

AD: You’ve heard me talk about Hostfully a lot over the past few months. I love sending my beautiful Hostfully guidebook to my guests as it makes me look very professional. I also love using screenshots of my guidebook on my actual Airbnb listing. This helps me stand out from the crowd. Now, I’m thrilled to announce I’m a sponsor of the Hostfully Host program. Twice a month, Hostfully selects a host and features them on their top ranked blog. This is great promotion for your listing and a cool way to share your favorite, local spots to a large audience. What’s even cooler is each Hostfully Host gets a free set of sheets from the clean bedroom. Now that I’m a sponsor, you’ll also be featured in my newsletter, my social media feed and you’ll get access to my video course on how to be a great host. For more details and how to apply, visit Hostfully.com/Hostfully.

Jasper: So, are you using any tools to manage your Airbnb listing. You mentioned you’ve always been an early adapter of new technology?

Jack: Yeah, actually, I’m really looking at dynamic pricing right now. I haven’t found a tool other than a lot of tedious keeping track of bookings and when they were made and seeing how far ahead of the booking year I am each year so I can use that to more aggressively drive my prices. That’s tedious. Like I say, I haven’t found a tool that per say works for that because I’m in a small community. There’s only three Airbnb on the sunshine coast. They don’t have the tools to handle a market that small. What I have been using is a product that you turned e on to Aviva IQ, to schedule specific messages to my guests. To do that automatically, so that I don’t have to worry whether or not I’ve remembered to send out my email about the keyless door lock code to my guest. I just started using that and I think it’s going to be a great tool. Basically, when I get a booking, it involves four separate messages. The first message is a friendly welcome, confirming their reservation. I have a little video I created several years ago of some pictures of what they’ll see and things they can do when they’re visiting. It’s just a teaser. It’s a minute and a half long, and most people don’t mind watching something for a minute and half, they’ll watch 30 seconds and it’s enough to make that connection. About 4-5 days before they arrive, that’s when I send them directions, detailed directions, on how to find my location and I also send them a link to a blog that I prepared called 72 hours on the Sunshine Coast. It’s a take-off on the New York Times 48-hours in Cuba or 48-hours in New York City. I do 72 hours. From the time, they get on the ferry until they leave, there’s 15 things for them to do. Including, my recommendation for where they stop for lunch, for dinner, where they have breakfast the next morning. Dinner that night. All in all, 15 things I’m personally recommending. I’ve had incredible response from guests on how much they appreciate that information. Then, on the morning they’re due to arrive, I send them another little email saying “hey, I know you’ve been busy trying to get away, here’s the link to the video and blog again.” Usually they’re waiting on the ferry to come over, so I’m catching them when they’re starting to relax. The fourth email is thanks for staying with us and requesting them to write a review. So, Aviva IQ manages all that automatically. It personalizes the email. IT allows me to put in my own specific content and then you can specify precisely when you want those emails to go out. For instance, my confirmation of the booking, it goes out ten minutes after they’ve made their booking on Airbnb.

Jasper: Awesome, for the listeners who haven’t heard about Aviva IQ, you can sign up for free at www.AvivaIQ.com. Before I let you go, I want to ask you one more thing. You’ve talked about providing good directions. I know it’s something you’ve noticed staying at other Airbnbs when you travel, sometimes the hosts don’t provide accurate information which can be challenging.

Jack: Yeah, we were in Eastern Europe in May. We were in Venice and we traveled through Croatia, and European cities are not made out in traditional North American grid systems. Directions are challenging. Often, it’s difficult to find the name of a street and even the number on the building. Just to give you my worst-case story, we flew into Schlage, we landed in the airport, hopped into two cabs and I had mapped everything out, and of course Airbnb provides a google place marker for the location. I was using that for the driver. He brought us to the location. We get out and the place marker was incorrect. We were actually about 400 meters from where we were supposed to be. Which may not sound like a big deal, but when you have a series of streets going off in different directions, it was confusing. There’s five of us and we’ve all got luggage and we’re trying to find out where this place is. I phoned the host, who it turns out, was in Italy. Two phone calls still unable to find the location, I said to her, is there someone that can come out to such and such street and meet us? That’s what she did. Eventually, we got settled in. It’s not a good first impression. It certainly, when ratings and reviews are important, first impressions are really important. In fact, one of the check boxes that Airbnb uses in their review is their check-in. I downgraded a bunch of places because the check-in wasn’t seamless. Now, I should say other parts of our trip, the host did come out and arrange to meet us. They used the messaging service to say, “can I meet you” and where that happened in 2-3 situations it was great. Quite frankly, these places are often very difficult to find. I think a combination of providing very clear directions but also using the Airbnb messaging platform to stay in contact with your guest and I think your guest on the podcast the other day said you should be responding to your Airbnb messages within minutes rather than hours. Certainly, when you’re expecting guests to be arriving. We all have 3 o’clock check-in, you have to stay in close contact with your guest to walk them through if they’re encountering any problems. The first advice is to hosts, check your directions. Walk through or drive through the directions to see if they’re clear. If you are in a location that is difficult to find, set up a meeting place. Use the messaging service to stay in close contact with your guest. In the end, it’s going to end up in positive reviews instead of negative reviews. Negative will hurt your business.

Jasper: Sometimes it’s hard to imagine that guests would have trouble finding your place because it’s easy for yourself. Sometimes it’s hard to put yourself in the shoes of the guest and imagine it’s tricky to find. I had my own experiences spending time trying to find my Airbnb recently, in Moscow. Both times I was unable to find the place and it took up to almost 30 minutes before I contacted the host. You can’t be specific and accurate and detailed enough when it comes to directions. It’s the first impression. If people can’t find it, it hurts the experience. Another out of the box thinking to provide direction is to record video of yourself arriving at your space. Let say you go to the nearest airport and you film yourself as you get a ticket or taxi or whatever the best way is and sending that video to people. Fast forwarding to make it not too long, that could be a good way. Make sure there’s a picture of the door of the space. One of my Airbnb is Russia had multiple entrances, so I didn’t know where I was supposed to ring the doorbell or what entrance I was supposed to use. Those are things you can do to be more accurate and provide more guidance.

Jack:  Those are all great ideas. In a number of those difficult situations for us, it was frustrating, because you’ve got your luggage with you, you’re tired, it can be late at night and it’s definitely not an experience you want to put your guests through for a variety of reasons. The direct is, don’t get a negative review because someone had a poor experience.

Jasper: Absolutely. Thank you very much Jack for sharing your insight. I think you provided a lot of interesting information for all the listeners out there, you’ve certainly been inspiring for myself. So, thank you very much. Good luck with your business on the west coast in Canada.

Jack: All right, Jasper. It’s nice to talk with you. I certainly enjoy listening to your podcast. I’ve learned a great deal from them.

Jasper: Will do, for sure. This Friday there will be another episode, which is the news. I hope to see everybody on Friday.

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