DGS 142: Growing Your Rental Business & Lowering The Cost Of Vacations With Rick Bennett

Do you wish that you could travel more often, but it’s just too expensive to find a place to stay? Investors and property managers are eager to get into the short-term and long-term rental market in popular vacation destinations. How can they grow their rental businesses and lower the cost of vacations?

Property management growth expert and founder/CEO of DoorGrow, Jason Hull, talks to Rick Bennett about BookingWithEase and TripAngle, which puts control back into the hands of property owners.

You’ll Learn…

[02:14] Business Plan: Why Rick wanted to make vacations more affordable for all.

[02:56] Thought Process: Lower the cost of vacations by eliminating overhead costs.

[03:08] TripAngle: Tools for owners to efficiently, easily rent properties, lower overhead.

[03:44] Systems and Services: Grow organically, save money, gain exposure for rentals.

[05:04] Differentiator: Only site that guarantees no double bookings; easy to use.

[07:10] Property Management: Fully automated, 100% customizable with parameters.

[09:42] Plug-n-Play Integrations: Change anything, anywhere with the TripAngle system.

[14:13] Why Rick prefers property management companies more than property owners.

[17:08] Software Learning Curve/Support: People know how to list their properties.

[19:22] DoorGrowShow Listeners: Try TripAngle by using representative ID code – 2167.


“How do we lower the cost of vacations? What we came up with is eliminating the overhead to the owners completely and lowering the cost of their travelers significantly.”

“We built tools for the owners to be able to rent their properties easier, more efficiently.”

“We’re the only site that can guarantee no double bookings because of the way we built our system. It’s just much easier to use.”

“We’re just growing everybody’s company. That’s all we care about is growing the owners’ rentals.”


DoorGrow and Scale Mastermind

DoorGrow on Instagram

DoorGrow on YouTube





Breckenridge Lodging

Mountain Ski Trips



Home Away





Jason: Welcome, DoorGrow hackers, to the DoorGrowShow. If you are a property management entrepreneur that wants to add doors, make a difference, increase revenue, help others impact lives, and you are interested in growing your business and life, and you are open to doing things a bit differently, then you are a DoorGrow hacker.

DoorGrow hackers love the opportunities, daily variety, unique challenges, and freedom that property management brings. Many in real estate think you’re crazy for doing it. You think they’re crazy for not because you realize that property management is the ultimate high-trust gateway to real estate deals, relationships, and residual income.

At DoorGrow, we are on a mission to transform property management businesses and their owners. We want to transform the industry, eliminate the BS, build awareness, change perception, expand the market, and help the best property management entrepreneurs win. I’m your host, property management growth expert, Jason Hull, the founder and CEO of DoorGrow. Now, let’s get into the show.

My guest today, I am hanging out with Rick Bennett. Rick, welcome.

Rick: How are you today?

Jason: I’m doing fantastic so I’m really excited to have you here. We haven’t had a lot of guests talking about the short-term rental space and the vacation rental space. A lot of property managers are getting into this. It’s becoming really hot. We’ve got shows on Netflix about it now. Everybody is abuzz with this market. Lots of investors want to get into this space. Property managers, even in the long-term space—if they are in coastal areas or have really popular destinations—have vacation rentals they are also managing and dealing with.

You’ve been an expert in that industry for a while. Why don’t you give us a little bit of background on you, how you got started with this, and then we can hear more about Booking With Ease, TripAngle, and all these cool things that you’ve got going on.

Rick: The reason we started this whole business plan is because my mom passed away when I was younger. One of the last things she told me was that she wishes she could have traveled more often, but it was so expensive. The reason she mentioned that is she had a really good job, and they flew her everywhere. But to include me, her son, who she wanted to bring me to several places—she took me to Philadelphia, Boston, you name it—it would cost her the full price to bring me. Her company paid for her.

I remember pretty much every time she would tell me man, I would love to take you to Charleston. I just can’t. She was very apologetic. That’s one of the last things she tells me. She wishes she could have travelled more often.

Our thought process was how do we lower the cost of vacations? What we came up with is eliminating the overhead to the owners completely and lowering the cost of their travelers significantly. We came up with TripAngle. TripAngle actually merged with a company called Keys to the House that’s been around for over 25 years. We’ve been in the industry forever.

We built it from the ground up. We have our own MailChimp, and we built tools for the owners to be able to rent their properties easier, more efficiently, and once again, lower their overhead big time.

When you rent through some of the big boys online with the vacation rental listing sites, it can be quite costly. The reason being is they keep outbidding each other to buy the top spots. What we do is we grow organically. We spread by word of mouth because everybody loves to tell everybody the money that they’re saving. We work in conjunction with everybody else. It’s a way to just gain more exposure for their short-term rentals.

Some of our customers use our features, some don’t. We offer free accounting and scheduling for cleanings. We even have where instead of putting our business on all the receipts, you can upload your logo, and all emails sent to your customers have your logo on them. It looks more professional. It’s to grow your rental business. We just grow by word of mouth, and we love saving all of our owners’ and customers’ money

Jason: People can white-label this. People can use your tools and services. They’re going to save a lot of money versus using these systems that have been a monopoly (it seems like) to some degree. You’ve got Vrbo. You’ve got the HomeAway things. You’ve got Airbnb, of course. How do you stand out in this market of all these big guns? Why would property managers be inclined to leverage and use your system instead of these big networks?

Rick: They can use them in conjunction with it. It works well. It keeps the calendars in tune. We’re the only site that can guarantee no double bookings because of the way we built our system. It’s just much easier to use.

What happens is people will sign up with us. They’ll use other people mainly. They’ll use us a small percentage, but they’ll use us. Once they start seeing how much money their customers have saved and how easy it does everything for them, they start transferring everything over to us.

We just had a lady sign up with us. Vrbo upped her booking fee to $470. Using our system, on average, her booking fees are about $100. What’s neat about that is she makes $20 extra, meaning it’s 100% customizable per property. She added the dollar amount. Some people add a percentage amount.

Jason: So you can add your own markup.

Rick: To the processing fee, right. Her customers went from Vrbo paying $470, and now, they’re paying $100–$120 and she makes $20 every booking on top of that in addition to saving the customers $300 a pop. Not to mention that Vrbo also charges her to rent it out. They charge a percentage and things of that nature.

Most of our owners collect their own income, their own credit cards. If they collect, our services are 100% free.

Jason: Okay. For those listening that are property managers, they can do this and act as the owner for and on behalf of their owner-clients and do the same thing.

Rick: Absolutely. Property managers, condo complexes. We’ve helped a lot of people basically get out of the restraints of property management.

I spoke to a town in Texas just recently. They just signed up with us, but the woman told me that they only have the same three property management companies. They’ve gone through that list about five times because they’ll pop somebody, get tired of it, fire them, and go to the next guy, but that’s all they have access to.

Now, with our system, it does everything for them. It’s fully automated. Once you set up your parameters, it’s 100% customizable, meaning some of our owners collect $1 amount at the time of reservation. You can set it up per listing. Others collect a percentage of the rental. Some of them charge the remaining balance—which it does automatically through our system once you set that parameter—two days prior to a guest’s arrival. Others have it 60 days prior to the guests’ arrival. Just whatever it is, it’ll run automatically.

Somebody lists with us. They say, put $20 down, they’ll make $20 extra every reservation, and their customers are saving quite a bit of money. Another thing that they save money on is through Vrbo and Airbnb, they charge $60–$65 for $1500 worth of damage protection on their property. We sell $39 for $3000 worth of coverage. We make sure that all of our owners are covered. We built this to grow the owners’ companies.

They can add as many fields as they wish. The way it works is let’s say they put it in there and say, run the remaining amount 10 days prior to the arrival. Let’s say they put 50% down at the time of reservation. When somebody books that, that amount will charge for 50% down. It will shoot them a receipt with their logo on the top and check-in instructions with their logo on the top. Nothing to do with us.

Ten days prior to the arrival—if that’s the parameter they set—it’ll run it in full, it’ll schedule it to be cleaned, and it’ll alert the cleaners. The cleaners even have it color-coded, knowing if there’s an out and in that day. They can make notes. All those notes are sent back to the owners once they’re cleaned.

Whenever it runs it in full, it’ll send them all that info. Two days prior to their arrival, it will send them again that receipt showing paid and check-in instructions because some people make a booking a year ahead of time. Then, a couple of days before, they’ll get reminded, this is how you check-in. Our customers can do anything they need. Sometimes, somebody will say, hey, can you send me that receipt again? All they have to do is log in to our website and send it back to them.

Another great feature is if they collect their own credit cards, more than likely, they use a company called Authorize.Net. All Authorized.Net is just an online credit card machine. That’s it. Whenever people go to log in Authorize.Net, they make you change your login all the time. It can be somewhat frustrating. Through our system, they never have to log in to Authorize.Net. They can refund, they can charge extra, they can do everything through our system.

We’re integrated with RemoteLock. We’re integrated with Authorized.Net. We just helped integrate BookingPal, Vacasa. We’ve got some big tentacles out there, and we’re just growing everybody’s company. That’s all we care about is growing the owners’ rentals.

Jason: Awesome. For those listening, a lot of property managers who hear this will go, wow, that sounds really great. Maybe it’ll replace me. Maybe you could touch on that. Is this something that the property managers listening to this could use for and on behalf of their owners to be really effective, have better tools, better pricing, and maybe be a better profit center for them?

Rick: We have a ton of property managers that use us. What it’s done is it helped them eliminate more than half of their staff. It really helps do that. We do hate that a lot of people are getting let go, but it helps make the owners more money. That’s what it’s all about.

Jason: Business owners, I don’t think, would be sad to hear that they can’t. They don’t need as much staff. Staffing is always the most expensive resource in a business generally, so every business owner would be happy to hear that they can operate with less staff.

That doesn’t mean they’re just going to fire everybody, but maybe it means they now can afford to spend more on acquiring more properties to manage, doing more marketing, and shifting their team members’ efforts towards building the business up instead of just trying to deal with what’s coming in.

Rick: We just talked to an owner in Texas that signed up with us not that long ago. This was about a year ago. I remember her specifically saying—and it blew me away—how her property management company at the time used software, meaning that if anybody made a change to a reservation or anything, she would have to go to the office to make everything. From our system, you can change it from your cell phone, tablet, or computer—you can change it from anywhere.

We’ve taken as much out of the owner’s hands as possible. Let’s say they have it where it charges 10 days prior to their arrival. It’ll schedule it to be cleaned. It’ll do all that stuff. Let’s say somebody calls and says, hey, I want to change my dates or change my condo or home. You can change it in our system with just one click of a mouse. It’ll change the cleaning for them. It’ll change the calendars on both their properties. It does absolutely everything for them. It’s really a simple tool to use.

Another great feature is we have search by availability for owners’ websites where it will only go through their rentals. We offer rate tables, calendars, custom-built widgets for owners’ websites to more efficiently run their rentals, and tape charts.

Jason: Rick, let me clarify some of this for those listening. Most of my property management clients and property management business owners refer to their clients as owners. I just want to make sure for those listening, it sounds like what you’re saying is when you’re saying owners, you’re talking about the business owners really. It could be the property manager or the direct owner of the property, but you’re talking about the business owner.

These business owners have these tools available for them to integrate your system with their website for bookings, to manage their business, to send out white-label emails with their own branding on it—all this stuff.

Rick: Yeah. Mailchimp can send specials to everybody they’ve been with, but as far as the clients go, property management companies love using us. They’ve been able to grow their businesses and like I said, cut their costs. It’s a very simple tool to just plug and play. We’ve helped a lot of property management companies really get over the hill, so to speak.

Jason: You showed me around a bit and had me take a look at stuff. My feedback was initially, it’s not the sexiest, prettiest thing, but it sounds like it does everything. It has lots of bells and whistles. You guys have put a lot more attention on the backend, on integrations, on features, and really, it’s very client-centric. It sounds like your business is really taking care of your customers and making sure you’re building the best product that can do a lot of cool stuff.

My feedback to those who are listening to this is give it a check out, take a look at it, and don’t judge the book by its cover. Really get into the features and the benefits that could be really beneficial for your business.

Rick, what are some of the biggest questions that a property manager who has never used your system? You’re selling to them, what are some of the biggest questions that they’re concerned about or they want to know?

Rick: We prefer property management companies as opposed to individual owners. We serve everybody. We have tons of different clients. But if an individual owner comes to us, they have one property, two properties, we answer those questions. Once they’ve asked those questions, they know how to use the system so we don’t ever have to hear from them again. We prefer a property management company with 500 properties asking those 1 or 2 questions and then learning the whole system. They’re off and running 500 properties as opposed to 1 or 2.

It’s fully accountable. It’s 100% customizable per property. If you put 10 properties on our website and you wanted all 10 properties’ money to go to a different account for each rental, we have that option available to you. You can set it up per rental.

We have it to where some you charge tax, some you don’t. We even have features in Florida, if they stay 180 days or longer, it’s considered a homestead. If you book a rental for four months, you have to pay taxes on those four months. Those taxes are usually about 17%, 18%, 19%.

In Texas, it’s 30 days. If they stay 30 days or longer, it’s a homestead, so there are no taxes. Whenever they set it up with us, they could say, I want to set up city tax at 7%, hotel tax at 6%, convention center at 2%, and only charge if they stay 29 days or less. If they stay 30 days or more, don’t charge taxes.

It automatically does the calculation for them. It does it all right there. They book it, they get sent their receipts, and it really helps our owners out because they see where the taxes need to go. It’s all itemized right there. They can edit their spreadsheets on our system. Some pay for extra cable, and some like to add in their homeowners’ dues. It’s just got every feature you could think about.

Another great tool for our property management companies—I’d say 70% use the tool this way, whereas 30% use it this way. Some of them, the 30%, make it to where their owners can change things. I have an owner in Virginia that has a property in Florida. They may want to change some pictures on their listing or they may want to change the cost of the property. They can log in themselves through TripAngle, edit that one property, and it will change it on the property management company. That’s about 30% of our property managers.

The 70% don’t like them being able to touch anything, and that’s understandable. They could show everything through there. But once again, we made our entire system 100% customizable for whatever their requests are.

Jason: Usually, with software that has so many options, features, levers, and buttons, it gets a little bit confusing. How steep is the learning curve? What’s the support process like in terms of getting onboarded?

Rick: The support is we will hold your hand and walk you through everything. People know how to list their properties. They’ve done it on Vrbo and on Airbnb so they know how to do all these things. We get very few questions. We should probably get more questions, but people seem to figure it out pretty easily. But people will cancel their reservation. They will change.

Our system would be 100% automated if it wasn’t for this, but since people do change and they’ll call, we’ll show them how to click a button or two on our website, and they’ve got it. You’ve got a section for all active listings.

We even have a feature if you want to set it up to approve the booking. Some people have their property listed on so many different websites. They don’t even really know how much they have it listed on so they don’t like to take the instant booking, which I understand because it could have already been booked and you just didn’t think to put it on there.

Our calendars will stay booked. If you have it synced with Airbnb or Vrbo, it will stay in tune. But a lot of people don’t like to use calendars on any of them, and they like to approve a booking. A booking will come in, and they have 24 hours to approve it. I’d say 90% of the bookings that come in are approved by our owners.

Once again, they can just make it as customizable as they want, but it’s really easy to use. It’s really simple. It’s all about keeping it simple, stupid. We learned that a long time ago and man did we not make it easy getting to that point through professionalism and luck. We have some partners that can do anything. Our team has really been on top of the ball in just putting everything together. If there are ever any questions or any problems, we fix it within hours. We don’t have any.

Jason: This sounds really great. How can people get started with this? How can they find out more? What would be the next step for those that are curious of taking this for a test drive or maybe taking a look at it?

Rick: What they can do is they can go to either one of our websites, bookingwithease.com. You can look at our features. It just answers some of your questions, the general information of every company. It gives you links to be able to click on where it’ll divert you over to TripAngle and you could sign up. It’s free to sign up.

Once you sign up, we recommend putting a RepID number. You had a RepID number for us because I wanted to have a RepID number in there to make sure that the people from DoorGrow get taken care of. What was that RepID number again?

Jason: Rick, had me set up an affiliate code or a RepID number. My representative number is 2167. I guess if they go in once they’re going through the registration on tripangle.com, towards the bottom, there’ll be a representative number. If you put in 2167, Rick’s going to do some special for you, some discount or something like that.

Rick: Absolutely, yeah. We take care of all of our customers. We’d be happy to reach out to them once they put in that representative ID number. That’s how we’ve grown our business is word of mouth. Most people like to tell others of the great deal that they found. Once they realize what they make on it, they love it. We pay 10% of what we earn. We’re doing strength by numbers.

The reason our numbers are so low compared to everybody else is because they’re trying to compete with each other. We’re doing it organically through each other’s websites and spreading by word of mouth.

As people sign up with us—let’s say somebody enters in the 2167 under you, what that will do is on your dashboard, you’ll be able to see who’s signing up, what bookings are coming through, and all that good stuff. When you have a customer sign up through DoorGrow, they go in there, they sign up, they can agree to our affiliate program—just like you did—they’ll be assigned a number, they can tell their neighbor to go sign up, and they’ll get 10% of every bit of our earnings per property.

Jason: Very cool. They can go to bookingwithease.com which also links to tripangle.com where they would register. They can also just go to tripangle.com to check that out. Cool.

Rick, before we wrap this up, is there anything else you feel like a property manager should know regarding TripAngle?

Rick: They’re in the process of uploading all of them, but we just signed about 3000 properties in Colorado where I know for a fact that they’re offering it through an affiliate either breckenridgelodging.com or mountainskitrips.com. If you go to those websites, it’ll have our link to be able to book their rentals. You can pick out their rentals, but they’re offering 15% off right now for the first month. They just signed up with us.

Any properties you find in Colorado on our website should be through those companies—Breckenridge Lodging or Mountain Ski Trips. They’re offering 15% off right now on top of their already lower rate.

Just to give a quick example, I spoke with a lady the other day from Airbnb. She was a traveling nurse. She asked if she could book one of our rentals. She said she could only afford $1400. If she would have booked directly through TripAngle, it was $1275. She would have booked for less. But through Airbnb, you can’t really discuss information until after the reservation’s made.

I went in there and I adjusted it to where she should have been at the $1400 range. I told her. I said we did the $1400. I don’t know what they charge. She looked at it and she said, I’ll never use them again. She wanted to book it for four months.

They were charging her $2350 a month, meaning they were making $950 a month to use our system when I’m the owner and I’m only making $1400. That doesn’t seem like it’s the right thing there. If they would have charged (say) $950 upfront, maybe a one-time fee, even that is too high if you ask me. But that’s the point. The cost of vacations has definitely skyrocketed since Airbnb has been introduced. We’re here to get owners more exposure. They use us in conjunction with Airbnb.

The one woman I just told you about from Vrbo for $470, she stopped using them quite some time ago. Airbnb can be fun. Let me tell you that. That can be exhausting at times. I feel that Airbnb has taken a lot of control out of the owners’ hands—a lot of it. Our system gives owners 100% control over their listings. If they want to go in and do anything through our system, they can do it.

I had a woman who, through Airbnb, booked for September 20th because I had somebody checking out on September 20th. She let me know just now that she actually has to be here on October 18th. She thought she booked it on the 18th, so I went to the Airbnb to switch it out.

It wouldn’t let me change anything. It was the most difficult process to get her. What I finally did was she agreed to pay me cash when she shows up. There shouldn’t be anything like that on Airbnb. With our system, you can adjust the rate. You can adjust everything. You can offer percentages for discounts.

One thing that a customer of ours just brought to our attention that they absolutely loved is they have over 2000 rentals. They use another website, but they have to go through on all 2000 rentals to add a discount for that rental. We offer—where you can do that—a master discount so it goes immediately on all 2000 of their rentals. That’s so much easier.

Jason: Yeah. Rick, I’m sure you could probably tell us features. You just spout these off the top of your head, but you could probably go on for an hour just telling us all the features and benefits of this. It sounds really awesome. Again, I recommend everybody to check it out. Go to tripangle.com or bookingwithease.com, and take a look at that.

Rick, I appreciate you coming on and sharing this with us. I think it’s cool. I’m excited to expose my audience to this. They’re always looking for some cool hack or something that might keep more money in their pocket. I hope your continued success against these companies.

Rick: One quick thing I do want to say—and this is all thanks to you—is I do love how you’re a straight shooter. Love it. You told us that our logo on TripAngle was awful. I don’t know if you know this, but I worked with your team, and they developed it.

My business partners and I were cramming, collaborating, and all over the place. What logo that we came up with doesn’t even hold a candle to what you all came up with. I even gave your team specific instructions envisioning in a certain way. What they did was 100 times better. I’m so glad they really didn’t listen to me because I was wrong. If you go to TripAngle right now, you can see that new logo. There’s one at the top and at the bottom.

Jason: I like it.

Rick: That came from you guys.

Jason: Yeah. My team does good work. That’s really cool.

Rick: They do great work.

Jason: I appreciate you being open to feedback. I’m a little rough but hey, if I see a business owner that has something cool but there’s something on the surface that would be super easy to fix that would make business easier, I’m going to call it out. That’s what I do. Kudos for taking some advice from me. Sometimes it’s not comfortable to be told your kid’s ugly, so to speak. They need plastic surgery.

Rick: Right. That’s why they have braces.

Jason: Awesome. Cool. I appreciate the little plug for my brand-new team. Rick, I’ll let you go. I appreciate you coming on the show. I’m excited to see what you do.

Rick: Absolutely. Thank you so much. I look forward to growing with you guys.

Jason: Awesome. If you have a crappy logo, you’re not really proud of your brand or how things look, you are being perceived falsely as mainly a real estate company, but you do property management, or there’s something off with your branding, let us teach you how to clean that up. Let us help you clean that up.

We’ve rebranded hundreds of companies. We are the world’s leading property management, branding, and web design agency in existence. Nobody else has probably rebranded more companies in the property management space than us. Nobody else has designed more property management logos than we have. We’ve done hundreds and hundreds.

Reach out to us. We’d love to help you out. We’re always excited to help clean up businesses. The level of growth they see before and after we rebrand, clean up their website, and get their pricing and everything in alignment are always far more profitable and the business comes far more easily. You don’t realize what leaks you have until they’re no longer there sometimes.

Reach out. Check us out at doorgrow.com. As always, if you want to join our community, it’s free online. Go to doorgrowclub.com and join our Facebook community. We’d love to have you there.

If you’re interested in growing your business, reach out. We have an awesome mastermind program. We’ve got over 70 businesses in it, and they are having phenomenal results. We’re really enjoying coaching and mentoring these clients, and helping them move their business forward.

We have three paths we focus on: we focus on growth and adding doors, we focus on scaling it and figuring out operations, processes, hiring, systems, all that, and then we also have our seed program which is all about the ultimate foundation, branding, website—everything on the frontend sales pipeline of the business.

Once you have all three of these things dialed in, you’ll have a very profitable company. You’ll be outpacing your competition, you will look like the best in your market, and you’ll probably be the best. Anyway, that’s it. Until next time, to our mutual growth. Bye, everyone.

About Jason Hull

Jason's mission is "to inspire others to love true principles." This means he enjoys digging up gold nuggets of wisdom & sharing them with property managers to help them improve their business. He founded OpenPotion, DoorGrow, & GatherKudos.