How to Pick Your Tech Stack for Your Short-Term Rental

From the Podcast: John joins me to share his process for building a tech stack for your STR business and walk us through the set of software packages he uses to run Ohana Stay. He explains why there is no perfect PMS and how to pick one that meets most of your needs—based on the features that are important to you. Listen in for John’s insight on creating the right cocktail of technologies and learn how you can make several existing software programs work together to get the functionality you need!

Original source: watch on YouTube

Transcript

0:01
welcome to another episode of get paid for your pad today I’m very excited to
0:07
welcome to the show mr. John and he is one of our legends he is a very active
0:13
member in our short term rental profit Academy inner circle and he has a lot of
0:18
expertise on technology so today the topic of the podcast is how to find the
0:24
perfect cocktail of different technologies for your short term rental so with that said mr. John and a welcome
0:33
to this show thanks Jasper it’s great to
Meet John
0:38
be with you great to talk to you we saw each other in January and now we’re just
0:44
doing everything uh virtually but yeah I’m really excited to be on your show yeah man it’s crazy to think that just a
0:52
couple months ago we were in Cartagena we were on the rooftop of that amazing mentioned that we’ve rented you know
0:59
having some beers and and just having an incredible time and and then like
1:04
literally a month later the whole world changed it was completely nuts but well
1:11
yeah man I’m excited to dive into into this because I know that this is some some of your you know some of your
1:19
expertise here on technology so I’m really interested to understand you know
1:25
how do you find the best technology for your for your short term rental right but before we dive into that let’s uh
1:30
I’m gonna give you the chance to to give us a bit of a background of you know your business where you’re located etc
1:38
okay my business is called Ohana stay I run a short-term rental company in
1:46
Honolulu Hawaii and I’ve been doing this for about five years now gradually I
1:52
started just by you know buying my own company and I was looking for managers and I decided that me managing my own
2:00
companies would be much much more effective than hiring someone else and
2:06
so over that time I’ve been building out my technologies and my systems so that I can manage my
2:14
we sufficiently and with a you know with the streamlined staff and so that’s kind
2:20
of how I built my approach to you know building up the technologies you know
2:26
just quickly you know related to what’s been going on you know with code vid
2:32
Hawaii’s been really careful in terms of letting you know people travel and so
2:37
the whole you know business has pretty much stopped for now I’m hosting you know doctors and nurses
2:44
I’m hosting some locals for longer turns days and I’ve spent this time actually
2:51
going through my technologies and trying to strengthen some of my system so that when we open back up we can get moving
2:59
sweet how did you end up in Hawaii cuz she you live in New Jersey right yeah I
3:05
live in New Jersey so it’s remote management and so that’s why I needed all the systems to work smoothly I’ve
3:12
just I’ve been going to Hawaii my first time in Hawaii was when I was nine years
3:18
old and throughout my lifetime I’ve been you know going there and you know once a
3:24
year once every two years on vacation and so as the vacation that though you
3:32
know expectation that those were getting more more popular that’s the market that I decided to jump into so you think can
3:42
you can you talk a little bit about how how do you find these properties when it’s not your local markets well first
3:52
first its properties that I want to buy it on right that’s how I started and so you know it’s just like pot you know
3:58
looking for properties that I’m interested in holding long term that’s how I got started now I’m finding
4:05
properties essentially through a word-of-mouth you know I speak with people who owned properties out in mine
4:13
market and we just discussed on kind of what I’m achieving what I’m doing and
4:19
people get excited about some of the the quality of the management as well as
4:24
some of the returns that I’m getting which oftentimes are 20 to 50% higher than what you know what
4:30
the market is performing and so through that you know conversation I’m able to find people who are interested in
4:37
working with me so you know I’m not throwing at a exponential pace but I am
4:43
looking you know very strategically on what properties I want to manage your own and when the right right things
4:50
aligned and I you know I try to get those properties under my management
4:55
yeah and I think one of the reasons that you have such a high performance on your
5:01
units is is exactly because you figured out how to use the right technology and
5:06
how to optimize all your systems so that’s one of the reasons I am really excited to talk to you about this now
5:13
this is it this is a challenge that a lot of people have right then when we’re talking technology you know we’re
5:19
talking mostly about the the management side right the the property management
5:24
software I think for there’s a lot of technology these days that you can use to run your short-term rentals to manage
5:31
them but I think the property management software is is the one where there’s
5:37
there’s so many choices we were in Cartagena and I asked all the legends
5:42
you know how many what property management software do you use and out of twenty people I think I got like 10
5:49
or 12 different answers so it kind of just shows that there there is no perfect property management system and
5:56
there’s so many of them and so it’s really hard to choose which one is right
6:01
for you and and the finger also kind of complicates it in my opinion is that once you choose a property management
6:08
system it takes a little bit of time before you really get used to it and you really understand how it works and you
6:14
can leverage the software so not only are there a ton of options and is it not
6:20
clear which one is the best but also it kind of takes a while to to get into it and to find out if a certain system
6:27
works for you so I guess we’ll mostly be talking about the the property
The cocktail of technology
6:32
management software but what I really like about your approach is you you always emphasize that
6:39
that there is no perfect technology for for every single host that it really
6:44
depends on the your business depends on your preferences etc and the way that you talk about it is is you talk about a
6:52
cocktail of technologies right you want to have a few different systems or
6:57
softwares put them together and in a way that it works really well so I’d love to
7:03
dive in and and get your thoughts on you know how do you how do you put that cocktail of technology together yeah
7:11
you’re you’re absolutely right there is no perfect software and it’s not a
7:18
software’s fault either it’s everyone’s business everyone’s needs everyone you
7:23
know what’s important to different people or different and so each business
7:28
has you know one software might be perfect for my business and it might be like the absolute worse for your
7:35
business and so there’s no way as far as I’m concerned that one company can anticipate all the different ways that
7:41
you know someone wants to use their software and so I’ve kind of designed myself to understanding that you know it
7:51
doesn’t exist this unicorn doesn’t exist and the way I got there was i literally
7:57
act on boarded my properties I have my
8:03
list here excuse me i onto the reason
8:09
Toki one rooftop or B rental which is now hosts fully up listing hosts away
8:14
your Porter guest E and other other software and when I did that I actually
8:22
really got my properties onto each of the platforms and tried them out and I was in search of that perfect software
8:28
that would you know work perfectly for me and then when one thing didn’t go right I was like ah I give up I’m gonna
8:34
go to the next software and Sue and I realize I can’t be doing this all the time and so I this is kind of how I
8:41
started you know my journey into looking at the different software so I guess the
8:49
things out of PMS does for you you know it can obviously there’s channel distribution calendar syncing
8:56
you know website building messaging price management there are lots of different factors and so you kind of
9:05
need to start off understanding what you need for your own business what’s most
9:10
critical to you so I’ll kind of break it
9:16
down into how I approach it my first and foremost question is what are the
9:21
channels that you absolutely must be on is it just their B&B is it Airbnb and
9:27
VRBO or you know do you need to be on booking.com so I think first looking at
9:34
what channels you know the available technology provider has tight
9:39
integration with not iCal sync but really you know API connections messaging all of that I think that’s
9:47
really kind of the first way to whittle down in terms of the available you know
9:52
software that’s out there for me it was Airbnb VRBO booking.com
9:59
and the direct booking website and you know this was a decision that I made about a year and a half ago that a
10:06
direct booking website was very important to start to develop and so I wanted to get a pms that had that
10:13
included so I think the first thing is what channel’s do you want to be on if
10:19
you want to be on everything then I think actually looking for PMS and a channel manager if you’re looking for a
10:25
subset then I think there are a lot of just PMS is that you want the different channels and then the second thing is
What are the core features
10:34
what are the core features that are really important to you right so don’t just go through the checklist of
10:41
features that you know that all the software providers advertise but really
10:47
explain to you know try to convince yourself what is the thing what are the things that you really really need so
10:55
for me it was really like seamless calendar syncing between the channels
11:00
that was priority number one you know in the five years that I’ve been running my business I’ve never
11:06
double-booking and so like I just wanted to make sure that the calendar syncing was you know 100 percent solid for me
11:15
another important thing was that it had a mobile app that was fully mobile meaning I could manage everything about
11:23
my business on my mobile app not just a dashboard but actually change settings
11:28
so you know that was an important feature for me that’s the PMS had a
11:35
direct booking component and by direct booking I wanted it to be my own domain
11:40
not like a subdomain of someone else’s so that over time I could know SEO so
11:46
that was an important feature for me as well the ability to push out dynamic
11:52
part to the multiple channels dynamic pricing as well as minimum length of stay so that was another feature that I
11:59
said was important and then automated messaging so out of all the different
12:06
things those are the things that I was really looking for when I was looking for my PMS and so the other point that
12:17
I’ll say is if while you’re shopping around you hear oh that’s enough that
12:22
features is in our pipeline and it’s coming in about three to six months that’s their way of saying no we don’t
12:28
have that feature and so do not fall for that I fell for that you know several
12:34
times where you know something was supposed to come out in two to three months and two years later that feature
12:39
still was not live and so just take that with a grain of salt that’s the sales
12:46
pitch of saying no we don’t have that feature so don’t fall for that I fell
12:51
for that many times so that’s how you start with the PMS right and so some of
13:00
the ways that so right now I’m using a PMS called your Porter which it’s most
13:06
of these needs for me again that’s not to say your Porter is the perfect PMS for everyone but it meets most of these
13:13
needs but on top of that your Porter’s
13:19
mess is not as robust as smart B&Bs messaging and so because of that I actually layer
13:28
on smart B&B or the you know a lot of the automated messaging features on top
13:33
of your porters and you know this is because smart B&B can kind of use
13:40
artificial intelligence to answer questions as opposed to your quarters just scheduling times when something
13:47
goes out and so you know I kind of make sure that they’re working together so
13:54
each system is doing you know what it needs to do I also find cleaning
14:03
management’s to be very important to make that seamless and smooth and while
14:08
almost every PMS has cleaning and cleaning and maintenance management a
14:15
lot of them the features there but it’s very difficult for for example my
14:20
cleaners to use that feature so that I can automate it with them and so that’s
14:26
something that was kind of not as robust with my PMS and so I use a service call
14:32
turnover B&B and that just focuses on cleaning and it has a separate app or
14:38
cleaners so that I can communicate with my few nurse they’re able to use the app and so like
14:46
yeah that’s kind of like my cocktail of technologies I’ve also tried all the pricing engines out there wheelhouse
14:53
beyond pricing price labs and kind of use that with all
14:58
the different PMS as I tried and I I
15:04
stacked that on top of my other tech know the PMS and the smart B&B and so
15:10
with all that said I’m looking for different pieces of software different
15:15
technologies that are available that other people have developed I’m not trying to make my own you know software
15:22
and then I spend a lot of time to figure out how can I make them talk together or
15:28
how can I make it so that they’re not duplicating their function
15:33
so that’s where I spent more my time and focus as opposed to searching for the
15:40
perfect chemist that meets everything that you know that I look for for my business
15:46
awesome well you just went through a lot of a lot of different things which is
15:51
awesome I have a couple questions number one is the the pricing so you you
15:57
mentioned that being able your PMS being able to push out dynamic pricing to your
16:02
listings was something that was important to you so do you use one of those pricing apps that you mentioned in
16:09
combination with your Porter do those two integrate or do you have to set that
16:14
up separately I do use a dynamic pricing
Dynamic pricing engine
16:19
engine I again like I said I tried you know all three of the main pricing and
16:24
dynamic pricing engines I’ve settled on Tice labs there are multiple things that
16:30
I think price labs does you know in a very unique way especially in terms of length of stay that you know I I feel
16:38
like I have a lot more control over my properties and this is one of the cases
16:44
where your Porter does not directly integrate with price labs they don’t
16:50
have a you know a direct connection well with that said you’re able to your
16:56
Porter is able to take the Airbnb information and then bring that into
17:02
into the PMS and then push it out to the different channels and to the direct
17:07
booking website and so you know I’ve I’ve contacted the CEO of your Porter
17:16
multiple times asking if you could please integrate with you know some of
17:21
the pricing engines but regardless you know i I’ve worked to get a workaround
17:27
so that I can get the pricing that I need the feature that I need through a
17:32
third party or a backdoor method to get that information back into your Porter
17:38
and then outs to booking.com the rbo and then onto the website and so yes that’s
17:45
you know that’s kind of the kind of links that I’m looking for again I’m not coding I’m not creating new you know
17:52
software or scripts I’m trying to use the functionality within you know within
17:58
the software existing software to achieve my end result and so one example
18:04
that I would also have is smart B&B also
18:10
has an ability to connect to Airbnb and VRBO for for pricing and so that’s
18:20
another back door method that I can use to get the pricing out you know even
18:25
though your order doesn’t have that direct direct link and so it’s those
18:31
like kind of how do you integrate the pieces to get the functionality that you
18:37
need that’s where I spend a lot more of my time and effort and communication with support to see if there’s some you
18:44
know hidden feature that that allows it to work yeah and so well you mentioned
18:52
me which I agree if you smart PBS by far the best messaging a lot of a lot of PMS
18:57
is offer automated messages but as you said those are there’s a scheduled right
19:03
so you can essentially you could say hey if a booking comes in send out this welcome message but smart bebe has a lot
19:09
of other functionality and they started as a messaging app right I mean they their rpms right now but they started
19:16
out as a as a messaging system so I’m just curious because I’m actually in the
19:22
process of setting up your porter myself because I’ve kind of done a similar research what you have been doing and
19:29
one of the reasons that I’m starting to use your porter is because I’m going to
19:34
put some of my properties in booking comm and I want to have my own direct
19:40
booking website so I’m diving I’m diving into your Porter as we speak by the way
19:46
and by the way if you’re listening to this you can if you want to check out your Porter you can use a decode PA
19:53
d-pad to get the 20 bucks off but going back to that messaging
20:00
I’m not completely sure how does it work when you combine those those two platforms so because in your Porter you
20:07
can send messages to so if you connect a smart beam be to your every meet listings and it starts sending out
20:14
messages I guess those messages then automatically appear in your report or inbox because your reporter takes a
20:22
messages from Airbnb right is that is that how it works yes so all the like the truth still in terms
Messaging
20:32
of the communication still resides on Airbnb and the way I do it
20:37
the thing I wish your reporter connected to booking.com but it doesn’t right so
20:43
that’s one of the reasons why I’m still using your Porter’s wait smart B&B I
20:50
wish smart B&B connected to booking calm but it doesn’t so that’s why I’m still
20:56
using the message is some of the messaging features on your porter and some on smart B&B so what I do is all of
21:05
the standard scheduled messaging you know when someone books the response and
21:11
all that I have that all set up in your Porter so that whether it’s booking.com VRBO
21:17
Airbnb directly booking website you know all that messaging is going straight out
21:23
from your Porter so it’s consistent and then I have smart B&B set up with the AI
21:28
with the questions you know hey you know if you have parking or you know just the
21:34
things that commonly come out can I have early check-in I set up smart B&B need
21:40
to respond to that so then that would only be on VRBO on Airbnb but I’m willing to live with that compromise to
21:46
be able to have that workload offloaded to smart B&B and pay you know a nominal
21:54
monthly fee rather than me or you know one of my staff having to jump every
22:00
time a question comes in so I think even
22:06
if smart be n be connected to booking comm I would probably still use your
22:11
porter as my PMS but I would probably switch all my messaging all the messaging over to
22:18
smart B&B around that and you know kind of splitting it up between the two and
22:24
you know it is kind of a pain in the butt having some messages going out from one plot you know one software and
22:29
others going on from another but again that’s kind of I want that ability to
22:35
respond to specific questions that you know that arise and so for me that complication is less less of a hurdle
22:44
because I get the value out of having the automated messaging does that make
22:49
sense yeah that makes a little sense and I’m just curious because I really like that functionality as well that smart
22:55
bebe has and just to explain a little bit to the listeners how that works basically smart beamy allows you to
23:02
identify certain key words so if you get a message and the message contains the word parking then you can instruct you
23:09
can set up smart beam me to automatically respond with a custom message surround parking right so you
23:15
can respond and say like hey we we have a parking spot for you outside or you
23:21
need to park to street down or you know whatever it may be you can send out a message and I think he can define as
23:28
many keywords as as you runs is that is that right yeah I’ll go a little further
Context
23:35
than that it’s more than keywords it kind of understands the context right so
23:40
it’s not just looking for the word parking so for example if someone asks about parking before they book they you
23:48
know you can have a certain response if someone asks about parking while they’re staying there then you can have another
23:54
response but it’s kind of looking at the context of the question and not just
24:00
keywords and over time you need to train it to understand you know a bunch of
24:06
questions and you know how to interpret that but it’s it’s actually you know quite
24:13
powerful you know basically for parking you have to put in like ten twenty
24:18
different ways of asking about the question and then the system will understand all right these series of
24:26
combination of words and you know questions come up then that’s you know respond this way
24:31
right so that’s that’s pretty powerful yeah yeah it’s pretty smart which makes
24:38
sense because it’s called smart beam B but ya know it’s it’s been really great
24:44
to see that that platform develop because I jumped on that pretty early on I think in 2016 or 2017 I jumped on the
24:51
smart beam be trained and I’ve seen it develop so I guess it takes a little bit
24:56
of time right to set it all up with with all those different ways that people can
25:02
ask about the parking and Wi-Fi and all of that but how many how many kind of
25:07
keywords have you defined within the smart beam beam I have about just like
Keywords
25:16
about six or seven questions and you know it’s it’s about parking it’s not
25:21
early checking and like they check out I have one about kind of you know what are
25:28
some of the you know nice restaurants or whatnot and you know I don’t just put
25:34
that as an automated message but I mean I don’t just send it out as information when people ask I have a specific
25:41
message that goes out where that yeah so
25:48
like I have about six or seven questions you know and the way I I determine what
25:54
to put in is if I get asked the same question two or three times then I’m
25:59
like okay it’s time to you know create a smart B & B you know rule around this so
26:06
that you know I can save myself some time but the other nice thing is it comes pre-programmed with things like
26:12
early check-in late check-out you know parking so basic things that most of us
26:18
normally run into smart bein becomes kind of pre-programmed to understand those things and then if it’s the unique
26:25
things that you want to train it you know it usually takes about two weeks I
26:32
think for it to start understanding you know seeing what other people’s questions are but it’s well worth the
26:40
time to kind of together and then almost never have to you know use that ever again
26:46
awesome and let’s uh let’s recap kind of the major points here because I know we
26:52
went through a loss but I think that I think the main challenges that I see in our in our groups in the short-term
26:58
rental profit Academy is you know people are tend to look for the perfect system
27:03
that’s that’s my first takeaway also from this conversation is really the perfect system the perfect PMS system
27:10
doesn’t exist alright so that’s number one thing this is one thing that everybody should understand is it really depends on your
27:18
situation but also your personal preferences because you know I asked my students and and one person says like oh
27:25
yeah I love you reporter and the other one says I hate it you know so it’s like you know there’s a personal aspect to it
27:31
as well the the interface the design those are all things that play a role as
27:37
well but so that’s the first takeaway there’s no perfect PMS second takeaway is that if if if it works really well
27:46
for one person it doesn’t mean that it works really well for the other person that’s kind of like it’s kind of the
27:51
same takeaway actually but I guess the next one is you if you choose to go over
27:57
certain PMS like you don’t want to give up the moment that you find one challenge right because you can switch
28:05
but you’re guaranteed to find a challenge in every single PMS right so your approach which I really like which
28:12
is the next takeaway is you know really figure out what is the functionality that you need right which are the
28:19
platforms that you need to be on especially booking.com is the one that not you know not every PMS integrates
28:26
with so I think if you want to be in booking calm or not that’s gonna be a
28:31
you know can be a game changer in at all for a lot of PMS and then the other
28:37
question is do you want to have a direct booking website right because not all the p.m. s-s offer a direct booking
28:43
website and then the next thing is you know do you want to be on like Airbnb VRBO and book
28:50
sort of the main channels or do you want to be like on the hunter channels right
28:55
because there’s this all these other channels as well right if that’s what you want then you really need a channel
29:01
manager I think guests he can do that I think you know rentals United and do that I did exactly right so but
29:10
obviously like that’s that’s gonna add up the cost as well I think your Porter is is a pretty it’s a pretty affordable
29:18
system to use you know some of the ones that that offer more integrations and
29:24
they they offer more Frank better functionality and stuff are also tend to be more expensive for they have a setup
29:29
fee right I think guest E or a very very robust system is a streamline for
29:36
example right some of our legends are using that but it comes with a set of fee and it is you know it’s a really
29:43
long learning curve involved so if you have like if you have a few units and you want to just be on air beam beam VR
29:49
Brio I think a system like a GMS could be a good option it’s it’s actually free
29:54
to use up to four listings you know smart beam B and your Porter those are
29:59
launched fi as well and those are there’s a pretty affordable houseful II
30:05
as well they they have direct booking functionality and pretty sure they’re on booking.com as well so those are kind of
30:12
those are kind of some of the options but but yeah I love your approach where
30:17
he’s saying figure out first what you need then choose own based on that
30:23
choose a system and just kind of stick with it for a while really learn and
30:28
understand that system and you know don’t just give up the moment you find a
30:33
challenge hit up the the CEO like you did Eric Eric the CEO of your Porter he’s
30:40
actually he’s a buddy of mine lives in Amsterdam so I met him a bunch of times he’s a really cool guy so shout out to
30:46
him but but yeah I think those are kind of the the main takeaways anything that you want to add to that yeah I think I
30:55
know it’s challenging to switch systems but the mindset that I have is because I
31:01
have these different pieces I’m constantly like testing out new things that are coming out and my
31:08
mindset is I’m willing to maybe not the fundamental PMS but all the other
31:14
ingredients I’m willing to change it out if I find something that works better for me and so it’s kind of this evolving
31:21
[Music] evolving journey of trying to piece together you know the best cocktail
31:27
right rather than just saying I have my ingredients and this is it and you know everything is done and I think with that
31:35
mindset that’s how like you keep on making that’s how you get to the perfect PMS is by bringing all your own pieces
31:43
that work for you as opposed to waiting for somebody else to make that perfect
31:48
software so I think that’s really kind of the mindset that I use and you know
31:53
for my business it’s it’s worked well again this is my personal opinion so
31:59
yeah don’t take anything over like all the pieces that I’m using oh this is what we you know we should be using
32:05
that’s not that’s not the point of you know what I’m trying to say yeah for sure yeah everyone has to figure out
32:11
what do you need what are the best systems for you you know look at the cost look at the function entities all
32:17
of that all right man cool thanks for Frank she’s jumping on here and and giving us your your thoughts on
32:23
technology I think that’s really useful to definitely challenge that a lot of people run into getting a lot of
32:28
questions around they’re always I hope Hawaii’s gonna open up and you’re you’re
32:34
gonna be back to lots of lots of bookings I definitely am excited to go back to a why I’ve been there a couple
32:40
times it’s an incredible island I shouldn’t say islands it’s a group islands right
32:46
I’ve been to Ohio I’ve been to the Big Island but I still need to go to Maui
32:51
and what’s the cold kowai kowai kowai kowai uh-huh that’s that really this
32:57
remote one right where that’s not so developed yeah it’s definitely much more
33:03
rural out there yeah after heading out you know and you know I could definitely hook you up three one one final thing is
33:12
I also work with some existing property managers
33:17
and it continued to manage the day-to-day in terms of cleaning and everything but I actually provide like
33:26
the technology back back system for them and you know that’s actually worked for
33:31
increasing their you know rates and everything so you know that’s also some some one of the ways that I work with uh
33:38
you know property owners or property managers and it’s not based on the technology stack that that I’ve built up
33:45
so yeah that’s awesome so somebody’s listening and once we get in touch with you and that what’s the best way to
33:51
contact you my website is
34:06
www.antakungfu.com all the systems that
34:25
we mentioned the software’s the technologies you can find those links at get paid for your pet comm there’s a
34:33
show note page for every single episode so there’s a you’ll be able to find all
34:38
the links also the link to john’s website and so you can check out as listings or if you’re interested in working with john that’s where you can
34:44
find his information as well so john thanks so much for joining and told listeners thanks for listening and
34:51
see you next time thanks Jasper