Latest / Host Planet: Airbnb, Holiday Let, and Vacation Rental Insights / Stop Sounding Like a Robot! Messaging Tips for STR Hosts

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Stop Sounding Like a Robot! Messaging Tips for STR Hosts · Host Planet: Airbnb, Holiday Let, and Vacation Rental Insights

• 0:00
  Hello and welcome to House Planet Bite Size, the podcast
• 0:03
  brought to you by Host Planet and House Philly.
• 0:06
  My name is James Farley, the founder of Host Planet, and our
• 0:09
  goal is to share everything you need to know about buying and
• 0:12
  managing short term rentals. Today's guest is Jay Ulrich from
• 0:16
  Host Buddy AI and he's got 5 tips to share about automating
• 0:20
  your guest messages. OK, real talk now for all you
• 0:24
  hosts out there, you know that moment when your guest messages
• 0:27
  you again with hey, what's the Wi-Fi code?
• 0:31
  Or you're staring at 5 different calendars wondering if you've
• 0:34
  accidentally double booked the cottage.
• 0:36
  Yes, we've all been there. That's why here at Hostplanner
• 0:40
  we recommend Housefully. It's basically your rentals
• 0:44
  control centre. It handles bookings across all
• 0:47
  the big platforms, syncs your calendars to ensure there are no
• 0:50
  double bookings, automates guest messages, and even creates these
• 0:54
  really slick digital guidebooks that stop all the repeat
• 0:57
  questions. Honestly, it just makes your
• 1:00
  life easier and keeps your guests happier, helping you
• 1:04
  achieve those all important five star reviews.
• 1:07
  And here is a little bonus. If you're a House Planet
• 1:10
  listener, you can get $500 off on boarding for House Fullies
• 1:14
  property management software and 30% off digital guidebooks for
• 1:18
  life. Just hit the link in the show
• 1:21
  notes and use the codes Planet 500 for the PMS and House Planet
• 1:26
  GB for the guidebooks. And if you'd like a proper
• 1:29
  walkthrough, there's also a link to book a demo with Frank Bosey
• 1:33
  from Housefully. He will show you how it's all
• 1:35
  works. Less stress, more bookings
• 1:39
  sorted with Housefully. Jay, thank you for joining us on
• 1:48
  House Planet Bite Size. You've got 5 automated messaging
• 1:53
  tips to share, so take it away with tip #1.
• 1:56
  Yes, thanks James. Appreciate you having me.
• 1:59
  First one that I'm going to start us off with is to create
• 2:01
  touch points with your guests. So this is going to be really
• 2:03
  important. I know this first hand as being
• 2:05
  a property manager managed around 45 units in San Diego and
• 2:09
  I started back in 2021. So a lot of this is coming from
• 2:12
  personal experience, but the touch points are really helpful
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  to just check in with your guests when they show up at your
• 2:18
  property midway through your stay, if it's more than a couple
• 2:22
  nights stay. And then even after a guest
• 2:25
  checks out, it's really nice, you know, prompting them to give
• 2:27
  you a positive review and things like that.
• 2:30
  And I've also noticed from the the guest perspective, when I
• 2:33
  stay at properties, if I feel like I get one message right
• 2:36
  when I book and then nothing else the entire way through the
• 2:39
  state could be great, but I feel like I wasn't really like
• 2:41
  involved, you know, that the the host wasn't necessarily there
• 2:44
  for me the entire time. So I found that to be really,
• 2:47
  really important for making sure that you secure those five star
• 2:50
  reviews. Yeah, I think that is integral
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  really, isn't it? So like optimum for you then is
• 2:56
  obviously they get the message when they book, then before,
• 3:00
  during and after. So it's like 4 main touch points
• 3:02
  really. Yeah.
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  And you can set these up to be just, you know, standard
• 3:06
  template of messages either through your OTA Airbnb, Verbo,
• 3:10
  or you can set them up through your PMS.
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  Now there's AI tools that also plug into your PMS that can do
• 3:14
  that for you as well. Very simple.
• 3:16
  Go ahead and do it people. OK, tip #2 Jake.
• 3:20
  Tip #2 is stop sending messages to the wrong guests at the wrong
• 3:24
  time. I think this is something that
• 3:27
  we end up doing because we set up these automated messages and
• 3:30
  then just forget that each conversation is kind of like a
• 3:34
  unique thing. So there is sometimes, you know,
• 3:37
  the guest sentiment is going to be negative and you're still
• 3:41
  going to send them a message saying, hey, I hope you settled
• 3:44
  in all right, Even though you've already had a conversation with
• 3:47
  them where they report all these issues beforehand and they're
• 3:50
  not having a good stay. So whether that's you making
• 3:53
  sure that you're going into your system that has the automated
• 3:56
  messages setting up and just skipping those messages, making
• 3:59
  sure they don't go out, or that's you automating that
• 4:02
  process using AI or some other system.
• 4:05
  I think it's really important just to make sure that it
• 4:07
  doesn't feel like you're you're just having this standard
• 4:10
  protocol with every single guest.
• 4:12
  Because when they receive that message, it's like really like
• 4:15
  you didn't think that I was going to realize this was just a
• 4:18
  normal standard message. Like the whole idea with those
• 4:21
  follow up automated messages is to create those person personal
• 4:25
  touch points with your guests. So if you're sending guest
• 4:29
  messages with with the wrong context, it just doesn't come
• 4:32
  off super professional. So there's AI tools that do that
• 4:37
  for you now too, which is really great.
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  And you can actually check the context with AI to make sure
• 4:41
  that those messages don't go out.
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  But I find that that's also really important, just to make
• 4:46
  sure you're maintaining that that personal touch.
• 4:49
  And will an AI tool pick up, pick up on that automatically,
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  say if you've had if a guest has been in touch and said, hey, I
• 4:55
  can't get in or they see that they've had a bad experience,
• 4:58
  they'll hold off sending the next messages.
• 5:01
  Can you train the AI to kind of do that?
• 5:03
  Yeah. So with host Buddy specifically,
• 5:06
  it's it's a context checking feature.
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  So if it's not relevant, it's just going to hold off sending
• 5:11
  it, which is really nice. It's it's going to read the
• 5:14
  entire conversation and make sure that you're not sending out
• 5:16
  messages that don't make sense. Excellent.
• 5:19
  Okay then tip #3. Tip #3 is drum roll automate gap
• 5:26
  night upsells. And this is a little bit of an
• 5:30
  automated messaging process, but it's also just a revenue
• 5:35
  maximization strategy. And this can be done through
• 5:38
  automated messaging, which is why I have it in this list.
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  And it's become really important for a lot of hosts nowadays and
• 5:44
  in competitive markets to make sure that they're maximizing the
• 5:46
  revenue. So to give this a little bit
• 5:49
  more clarity, when you have a minimum night stay, say of two
• 5:53
  nights, three nights, you're going to have two reservations
• 5:55
  sitting on either side of a gap night.
• 5:57
  You can't fill that night. People call them orphan nights,
• 5:59
  gap nights, whatever you want. But if you're not doing anything
• 6:03
  about it, that nights just going to go unbooked.
• 6:05
  And you'd be surprised how many guests would accept an extension
• 6:10
  request if you said, hey, we have a night that opened up
• 6:12
  right after your stay. You want to stay an extra night
• 6:14
  and maybe we'll give you a discount to fill it.
• 6:17
  And a lot of times, even if they're not able to actually
• 6:21
  accept that, let's say they have a, a flight already planned and
• 6:23
  they have to go and unfortunately they can't stay,
• 6:26
  at least they're very appreciative that you even like
• 6:29
  recommended that or offered it. And what I do with my property
• 6:31
  management company is we'll offer either, you know,
• 6:34
  extension of their stay or a late check out at a fee because
• 6:38
  we know that there's not going to be a booking that that night
• 6:42
  when they check out. And same thing for check in.
• 6:44
  We could say, hey, there's a night that opened up right
• 6:46
  before your reservation if you want to come early, or you can
• 6:48
  check in early at a discount. So I mean, we have, I see hosts
• 6:52
  that that make thousands of extra dollars per property per
• 6:55
  month on that just by, you know, filling those gap nights.
• 6:58
  And that can be done now automatically through a lot of
• 7:01
  AI systems and they're typically called gap, gap night upsells.
• 7:05
  Yeah, it's just about being proactive, isn't it?
• 7:07
  And then talking to the guests and telling them that it's
• 7:09
  available. And you, I think, you know,
• 7:11
  I've, I've done it myself. And you'll be surprised at the
• 7:13
  amount of times people say, do you know what?
• 7:15
  Yeah, we'll come for an extra night or we'll stay an extra
• 7:17
  night. If, if they can be flexible,
• 7:19
  they, they will do it. OK then 3 tips down #4 Jay. #4
• 7:24
  we got don't use AI. That doesn't sound like you, and
• 7:28
  I think this is probably the most important one in my
• 7:31
  favorite just because there's a lot of AI out there.
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  And when you consider all the options that you have as a host,
• 7:39
  sometimes you might think like, oh, as long as I'm using AI,
• 7:41
  it's going to benefit me. But not all AI is created equal.
• 7:44
  And I'm finding that more and more every day.
• 7:47
  There's a lot of AI embedded in some of the systems that you
• 7:49
  already use, but there's a lot of AI softwares out there now
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  that are created specifically for host in order to sound like
• 7:59
  a host and use all the right context, read the past
• 8:01
  conversations, mirror your tone. So if you're not using tools
• 8:05
  like that and you're just using, you know, even if you're just
• 8:07
  plugging in your conversations into ChatGPT, it's usually not
• 8:12
  going to understand enough context and it's not going to
• 8:14
  understand like your brand voice and your tone and all of that in
• 8:17
  order to make sure that you're providing a personal experience
• 8:20
  to your guests and a consistent experience to your guests.
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  So I think that's a fault that a lot of people see.
• 8:26
  And AI is a buzzword right now. So everyone's really talking
• 8:28
  about it. So I know it's difficult and
• 8:30
  there's a lot of options out there.
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  So I think it's really important to make sure that whatever AI
• 8:35
  tools you're using really reflects your own voice because
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  ultimately you don't want to use AI if it's not going to be an
• 8:41
  extension of you. So I think there are a lot of
• 8:44
  really great tools right now that are out there that are
• 8:46
  going to automate that guest communication process.
• 8:49
  But I will say I've seen a lot of property management systems
• 8:53
  implement AI and what they've done there is on the much more
• 8:57
  surface level side, like you can, you know, generate
• 9:00
  responses into your into the text field in the conversation,
• 9:03
  edit it however you feel needs to be done.
• 9:07
  But I will say when that when those features started to come
• 9:10
  out, I, I noticed because our virtual assistants started to to
• 9:14
  use them, but I didn't, I didn't really realize I was looking for
• 9:17
  the conversation. I was like, that doesn't sound
• 9:18
  like us. That's kind of strange.
• 9:20
  And they're like, Oh yeah, there's this cool new AI feature
• 9:22
  in the inbox. And I was like, hmm, let's take
• 9:24
  a look at that. So we started kind of playing
• 9:26
  around with it and we just determined it wasn't quite there
• 9:28
  yet. So if you're going to be
• 9:30
  automating AI or automating your guest communication with with
• 9:35
  AII would make sure that you're using a tool that's going to
• 9:37
  reflect your your voice properly.
• 9:40
  And how can you make sure that a tool is going to reflect your
• 9:42
  voice and brand? Is it simply a case of using it
• 9:45
  so the tool gets used to you? Yeah.
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  And I think it depends on on which tool it is a lot of tools.
• 9:52
  Now you can, you know, get a get a free trial and test it out and
• 9:57
  and really make sure that it's not making things up that it's
• 9:59
  going to sound like you. And it's kind of like that
• 10:03
  qualitative factor where like the measurement is, it's kind of
• 10:07
  difficult because it's not like, you know, you can measure it hit
• 10:11
  the mark every single time. It's just a feeling, you know,
• 10:13
  of like, does this sound like me?
• 10:15
  Is it something I would have said?
• 10:16
  Is it using the right context? Is it using the right background
• 10:19
  and information? So I think the right AIS right
• 10:23
  now in the space are gathering as much data as possible and
• 10:27
  using it to their advantage. And so those are the going to be
• 10:30
  the ones that are the best in my opinion.
• 10:34
  Like anything else in business really, but certainly in short
• 10:37
  term rentals, it has to fit your your tone of voice and and your
• 10:40
  brand. OK, then, J 5th and final tip.
• 10:44
  5th and final tip, I would say if you're going to automate
• 10:47
  guest messaging with AI specifically use SO PS and
• 10:52
  digital guidebooks. And you know, this kind of goes
• 10:55
  along with the idea of adding as much data as possible.
• 10:59
  There could be a misconception out there that if you use AI,
• 11:02
  like I said before, you know, if I plug in AI for my business,
• 11:05
  for guest communications, it's going to do a great job because
• 11:08
  everyone's saying that it can do all these amazing things, but
• 11:11
  it's only as good as the information that you provided.
• 11:13
  So if you have a property management business or if you're
• 11:17
  a host, let's say with just one or two properties, it's always
• 11:20
  good to have SOP, standard operating procedures for your
• 11:24
  business. So this is like exactly the same
• 11:27
  way that you trade an employee employee.
• 11:28
  You should be thinking about it the same way if you're trading
• 11:31
  an AI because it needs to know, what do I do in these certain
• 11:34
  situations? What happens when a guest shows
• 11:36
  up and the unit's dirty? How do I deal with an early
• 11:40
  check in request or a bag drop off request or, you know, a
• 11:44
  cleanliness issue. So there's all these different
• 11:47
  things where like if you had just hired a new employee today
• 11:50
  and you tried and you said, OK, here we go.
• 11:52
  Like go ahead and manage my business.
• 11:53
  They're going to make a lot of mistakes.
• 11:54
  And so you should look at AI the same way because you know, if
• 11:58
  you give it the right instructions, it's absolutely
• 12:00
  amazing. It's going to follow it to AT,
• 12:02
  it's going to fill in the blanks when it needs to, It's going to
• 12:04
  troubleshoot. And there's a lot of really good
• 12:07
  things out there that it can do when it has the resources to do
• 12:10
  so. So I recommend Sopsi recommend
• 12:13
  digital guidebooks. There's a lot of good ones out
• 12:15
  there that you can get my business we started back in 2021
• 12:19
  and we just created a guide book on our website.
• 12:22
  So each site, each property has its own sub root URL that just
• 12:26
  links straight to our website and they pull it up.
• 12:29
  If that's how you want to do it, that's great.
• 12:31
  If you want to use something like touch day or you know, a
• 12:34
  different digital guide book, that's also great too.
• 12:38
  But being able to use to pull that information in and, and,
• 12:41
  and, and input it into the AI is also really important so that
• 12:45
  you know, your team is going to use the information from the
• 12:47
  digital guidebook as much as your guests do.
• 12:48
  And to be able to recommend that consistent level of information
• 12:51
  is, is really important. So those two things, SO PS and
• 12:54
  digital digital guide, digital guidebooks are like huge
• 12:56
  necessities when you're going to be using AI.
• 12:59
  Yeah. And you know, these, these
• 13:00
  models, they rely on data and I guess that's one of the
• 13:03
  challenges with property managers.
• 13:05
  You need to find out everything you possibly can about a
• 13:08
  property in order to reply to guests effectively.
• 13:11
  But it's getting that information, isn't it?
• 13:13
  Sometimes you need to go direct to the source, which might be
• 13:15
  the property manager. All the info might not be on a
• 13:18
  website, for example about you know how to use the dishwasher
• 13:20
  or anything like that. Yeah, exactly.
• 13:23
  Yeah, I mean, there's so many different sources that you could
• 13:25
  use to like I've, I've seen people just write up documents
• 13:28
  like SO. PS don't have to be perfect.
• 13:29
  Like you don't have to have the Super League organized
• 13:32
  everything. You know, it's AI is going to
• 13:34
  use natural language processing. It's going to understand if you
• 13:36
  just write something out, just write like a whole page of just
• 13:39
  like situational things that you can deal with and and it can
• 13:44
  follow. It doesn't have to be perfect.
• 13:45
  So start. You got to start somewhere and
• 13:47
  just make sure you're including information.
• 13:50
  And if you need a digital guidebook, you might have heard
• 13:52
  our advert at the start of the show, 30% off Digital Guidebooks
• 13:56
  for Life with Host Fully. So that offer is in the show
• 13:59
  notes and there's a link there. You can go and grab 1.
• 14:02
  So take a look at that. OK, Jay, 5 fantastic tips there.
• 14:07
  Just tell us a bit more about Host Buddy and where people can
• 14:09
  find more information. Yeah, would love to.
• 14:12
  So host buddy plugs into the property management system.
• 14:15
  So you made them wondering over these tips, You know, how does
• 14:18
  that fit into the equation? If you use a property management
• 14:20
  system, it's a really great tool because it's going to plug
• 14:23
  straight in. It's going to pull all of your
• 14:24
  property details, all of your guest conversations, your
• 14:27
  availability, your pricing, everything like that.
• 14:29
  And then it's going to be able to respond to your guest
• 14:31
  automatically using AI for any conversation, whether it's
• 14:35
  coming from Airbnb or Verbo or direct booking.
• 14:38
  If it's going through the PMS, it can be responded to.
• 14:40
  And all those things that I mentioned about pulling in all
• 14:43
  the data and being able to, you know, plug in different data
• 14:45
  sources is all available within Host Buddy.
• 14:47
  So you can connect your digital guidebooks and cool, quick
• 14:51
  mention too, with Hostfully digital guidebooks.
• 14:53
  We just finished up an integration with them.
• 14:55
  So you can connect your digital guidebook directly from
• 14:58
  hostfully. It's going to pull in all that
• 14:59
  data dynamically and then obviously upload any other
• 15:03
  documents you like. It's going to sound like you
• 15:05
  mirror your tone, do all that great stuff and do the, you
• 15:08
  know, that gap night upsells and a lot of things that I mentioned
• 15:10
  today. So it really sits on top of the
• 15:12
  PMS and we're finding, you know, hosts are automating their guest
• 15:15
  communications by over 90% of the of messages.
• 15:18
  So yeah, I, I started that business back in 2023 to
• 15:23
  automate my own property management business and now
• 15:26
  selling it to to the rest of the hosting community.
• 15:28
  So excited to be here. You can find me on all the
• 15:32
  socials, but my name is Jay. And if you want to shoot me an
• 15:35
  e-mail, it's just Jay at host Buddy dot AI.
• 15:38
  Host buddy dot AI is our website and feel free to go to our
• 15:41
  website too. We have a nice tool on there
• 15:42
  where you can play around with the AI act as a guest and and
• 15:46
  talk to it with a bunch of random guest questions, which is
• 15:49
  a is a good thing to point out. You asked, you know, how can you
• 15:52
  how can you know that these AI tools are sounding like you are
• 15:54
  sounding like a host? And that's a good way where we
• 15:56
  put our public facing AI just out on our our front pages for
• 16:01
  people to use. So if you are curious, head over
• 16:03
  to host buddy dot AI. It's always fun to just see how
• 16:05
  it's going to respond. And we always give a two week
• 16:07
  free trial to anyone who starts a subscription as well.
• 16:10
  So. Fantastic, check it out and how
• 16:12
  much does it cost if people want to sign up?
• 16:15
  Yeah, it's between 6 and $10 per property per month, depending on
• 16:18
  your property count. Fantastic.
• 16:21
  OK, check it out, host buddy dot AI.
• 16:23
  Go have a play with that tool and check it out, Jay.
• 16:26
  It's been a real pleasure. Thanks for joining us on Host
• 16:29
  Planet Bite Size. Thank you so much, James.
• 16:31
  Appreciate it. Great to chat to Jay Ulrich
• 16:33
  there about automated messaging. I hope you found those tips
• 16:38
  useful. All right, that's it for today's
• 16:40
  episode. Remember this podcast is brought
• 16:42
  to you in collaboration with House Philly, which is trusted
• 16:45
  by short term rental professionals across the globe.
• 16:48
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  That's it for today's episode. Until next time, happy hosting.