How to Build Your Rental Portfolio Like A Real Business with Ryan Barone

Welcome to the Smart Real Estate Coach Podcast, your source for actionable, real-life, practical investing advice. Each week we help you make a quantum leap somewhere in your business, your finances, and/or your life. Subscribe, leave a rating and review, and learn more at smartrealestatecoachpodcast.com. Okay, smart listeners, it's Chris Prefontaine, your host again with another Super Smart Masterclass. I'm going to hang out and chat today with Mr. Ryan Barone, and I wanted to throw something different at you guys here. He's the Chief Executive Officer of RentReady. They provide independent landlords with software that helps minimize turnover, reduce the time needed to manage apartments, and increase profitability. So a really cool tool for landlords. Now, you guys all know that we're not landlords in our space, in our niche, We are putting buyers in the homes, but in a sense, we still have that responsibility, right? And you still have the management of your properties and your doors. They do this while making sort of an entire rental process seamless for the tenants and for investors. That's the whole idea here. And Ryan developed RentReady software for his web app, also for the iPhone app, the Android app, and server-side code. Guy's brilliant. You're going to hear as we dive into this. And by doing all their programming in-house, they actually ensure that RentReady is flexible enough to sort of listen and respond to landlords' feedback and updates. So it's forever changing. It reminds me, what I liked about it is it reminds me of our 3 Paydays system, our course, our online system, because we're always adapting. In fact, that's a brand new rebrand of it itself. Used to be called the QLS Home Study Program. So very much like us, they're on the fly, adapting, changing, and serving us investors. So with that as a backdrop, okay, Ryan, with that as a background, welcome to the show, my friend.

Thank you. Appreciate you having me, Chris. Excited to be here.

This is totally, totally, totally different, meaning, A, you've been around for, I was asking Brady, for like 9 years or so with this software, and B, I don't like, it's not often we bring software peeps on. We maybe had our CRM guy on a couple times, but this is pretty cool. So I want to dive into it. I'm genuinely interested. So just informal chat here. So help these guys, other than what I said in the brief intro, I just gave a line or two, help these guys understand what RentReady is.

Yeah, happy to. Happy to. So RentReady is an all-in-one app that allows anybody to self-manage their rentals. in a simpler, more affordable way and ultimately make them successful in doing so. I was listening to your podcast the other day with Jessica, and I very much resonated when you said like it is your life's goal, like your life's joy to bring success to people. And I love that you do that in the coaching way. And my way of doing that is in terms of the actual system, the tool that they can use, making it easier for them to handle everything in that rental lifecycle, whether it's collecting rent or finding that next tenant and listing it out and communicating them and handling all of the maintenance, making sure they're ready for tax season that we're coming up with. So it really spans the entire lifecycle of what you'd need to handle managing your rentals yourself in a way that's cost-effective from one unit to as many as you grow to. That's really the goal is to basically start anywhere. And if I can talk to you in a couple years when you've been on the platform for a while and hear how much you've grown over the time period, Honestly, that is my biggest joy. That's the most fun for me to get to have that conversation eventually.

Yeah. In a sense, you're like a mentor like us, right? I hesitate to use the overused word now, coaching, even though it's in our name, because there's so many people coaching that did a deal or went to a set, like it's crazy. But you guys are in the trenches. That's what I like, as I said in the intro, and same with us.

Yeah, yeah, absolutely. I feel like in my mind, it's, we were providing kind of the system that helps you Literally manage the unit yourself in a way that cuts out all that manual work for yourself and actually apply hopefully all the learnings you're getting from a coach like yourself or the books they're reading or other things like that. So just putting that learning into action and making themselves successful with their portfolio.

How did you, like, personally, I'm curious, how do you, how'd you stumble on this? Or like, what was your transition from what to this and how? Like, how did— Yeah. Yeah.

It's definitely an unconventional path of how I got here. I was going to school in New York City at the time, going to college here, and I went to Pace University here, double majored in economics and math, minored in computer science. I had gotten my first internship at Goldman Sachs, which was walking distance from Pace. And at the time, I'm just excited. I got my first internship. I get to move outta dorms, get my first apartment. I'm all excited to rent You know, my first place. And once I found this place, it would've been walking distance to both. They needed all of these documents for me, letter of employment, W-2, student transcript, tax returns, that for my guarantor. I had 2 roommates, all 3 of us had guarantors, and we ended up not getting that apartment. I ended up living about 100 blocks away from both school and work, and I came out of that experience Initially just thinking that the only thing that anybody needed help with was the renting experience on the tenant side and in terms of applying to places. And so initially I was just building an app for myself and friends to apply to apartments, not thinking this was a business by any means, not yet knowing about the whole side of it that we primarily support today, which is that like self-managing independent landlord and their tenant. And it really wasn't until I started bringing it to landlords and saying, hey, can I use this to apply? They say, yeah, but why did you leave our side the same? And I was like, I assumed your side was great. Like you're getting everything over email and you, I'm providing the documents the way you wanted.

And they're like, no, no, no, no.

We want a system where we can come in and see who's pending and be able to respond to them and how long they've been waiting, where they're trying to rent and things like that. And so I said, okay, I'll make the side for you too. And then, you know, some people said, I don't care about that at all. I, all I care about is When somebody calls me in the middle of the night and says, there's water leaking in my kitchen, I want to be able to see a video and know if I need to jump out of bed and go over there, if they can throw a bowl under it and they can wait. I was like, okay, we can give you video maintenance. Other people are like, I don't care about that at all. Okay, what do you care about? And they said, well, you know, I tend to tell me the check is in the mail, or I'm manually tracking all of this, or I'm having to remind them to pay rent all the time, and I don't want to have to do all of that manual work. Great. Tell us. How do you want to be able to set that up? And so honestly, it was thousands and thousands of conversations over the years. The first 3 years, myself and my co-founder did every single chat, every single phone call, every single demo. And so I lit— when I say literally thousands of landlords, literally thousands of landlords and their tenants that I talked to along the way, and it just fell in love with building this platform that makes it easier for both sides, for landlords and for tenants. And I think too often, you know, people get a bad rap of like bad tenants or bad landlords. And I think there's like good people on both sides. And unfortunately, more often than not, they don't have a good system in the middle. And if I can bridge that gap for them and make it where it's like you rest easy sleeping at night knowing everything's running well and your tenant's not bothering you and your tenant's like, I'm happy to live here and happy to renew, you know, I'm— It's a win. It's a win, right? Everybody wins in the end. It really naturally evolved out of people just sharing their own opinions about what their personal problems were and how they could see that being solved in a way that didn't just help them, but really helped everybody. And so I feel like it's really been a community-built platform over the past 10 years.

That's really cool. You know, I'm thinking aside from this whole journey with RentReady, your journey relative to the podcast is kind of cool because you, you know, it sounds like it was you and one person. Yeah. Um, and that's not an easy thing to start any business. So I just, I mean, it is not.

Thank you. I appreciate it.

Um, it's been, what did we say? Like 9-ish years?

Yeah. 9 years going on 10. This, this, this, this, this year will be 9 into 10. December will be 10 years. So just, just crossed over the 9-year mark.

So no looking back for you. So when— no, I gotta ask, I've got a few things I was writing as you were talking, as you probably saw. Is there like a free demo or something? Like, tell these guys how to go experiment so I don't forget to ask you that. Yeah, yeah, happy to. What do you feel like you want to share?

Yeah, they can go to rentready.com. It's R-E-D-I, rentready.com. We do have a free demo. We have a money-back guarantee. I loved your, by the way, the, I heard you did the, Free coaching sessions. You're like, you know, zero risk, right? Like it's, there's no downside, all upside. Our version of that is come in, try it. If you don't like it, money back guarantee. And so that's easy to get started. If you love it, $12 a month, as little as $5. But we don't charge you when you grow more. It's one of the things that I take a lot of pride in is—

Oh wow.

One of the things that's based on conversations Early on where people said like, hey, I stayed on spreadsheets because I don't want to be taxed for my growth. We figured out a way to basically build it where you don't have to be taxed for your growth. So it's been really exciting to build platform over the years. But yeah, you come on over to RenReady, we'll chat with them. We love talking to people. We've kept that part of our core to this day. Every single tenant, every single landlord can message us anytime they want, 24/7 about anything they need and we'll talk and help 'em.

That's awesome. So I'm curious now, because we have a big community, whether they have 5 properties like Jessica, who you heard, or whether they have 500. How would you compare? You must know, you've been at this a long time. How would you compare to like an AppFolio then?

Yeah, I would say the opposite end of the market. AppFolio is built for very, very large property managers. If you go to AppFolio site today and you say, I have less than 50 units, they won't even call you back. If you come to our site and say, I have 1 unit, we will happily set you up. And so the difference is we really built it for the individual, the one that, like Jessica, that's got 5 units or even 1 unit or 2 units or 10 units or 50 units. We're really not building it for the person with 1,000, 2,000, 10,000 units that the app folios of the space are targeting. I think honestly they've built a great product that helps that subset of very large property managers. And unfortunately, I think the individual rental owner, the individual landlord has been largely cast aside. And that's what we saw was that so many felt like basically if I'm not over this unit threshold, basically I have to do everything manually from my cell phone and spreadsheets. And when you get to a point where, like Jessica, I know I was talking about, yeah, I'm going to get to a point where I'm going to have to start hiring a team because I'm at 5 units now and She was at, you know, maybe a quarter of that a few years back, and she's going to get to a point where she wants to start bringing people on. We've built the system in a way where you don't have to change your systems as you grow. And you talked about like building up a company myself. I view it the same way. The way that we operate today, chat is very similar to the way that I personally did chat 10 years ago. And the beauty of it is like, if you do it yourself first, you understand it. And I think this is true of anything in life. If you do it yourself first, you really understand it. And so when you start to hire someone to bring them into your team and teach them how to do it, you'll have an understanding of what they need to know, what mistakes they might run into, what they need to look out for, and they'll learn some new things that they'll teach you over the years too. But it creates that great relationship, I think. So really the way that we focused on it is saying, you know, start with 1, 10, 50 units, completely fine by us. It's in fact who we built it for. But you can continue growing your portfolio without having to worry.

Good. I'm glad I asked that then, because that's going to affect most listeners, right?

Yeah, absolutely.

You know, it doesn't matter if you're brand new to real estate or if you've been doing this for several years or a whole bunch of years. I learned the hard way back during the crash that doing creative deals is much better. It's a much better path in real estate in general than, let's call it, the old way— getting paid once, using banks, signing personally. 3 paydays, getting paid 3 times on a deal. It's better 3 ways, not one. Money now, money over time, and money long term. And I don't care if you're in an up-down sideways market, it doesn't matter. You can and should operate with the utmost confidence. There's literally nothing I love more than helping people create systems and simple systems and processes to become massively successful with our 3 Payday System, in doing so in literally any market and doing it geographically literally anywhere. So if you've been learning and learning and listening and studying and not taking action, I'm telling you, after going through it myself, It's costing you tens of thousands, if not hundreds of thousands of dollars, by not taking action on the 3 paydays the way you should be getting paid. Many of the people that were brand new, just like you, that joined our community have fast-tracked their startup. Now, I mean, wouldn't that be ideal if you said, okay, should I go fast or slow? Should I take action now or later? It's costing you too much money to wait. Each one of you are at a point in your life, I'm sure, where you want things to be easier, you want things to be better for you and your family. You probably realize that you not only want more, but you deserve more in this life. So, to be able to give your family everything they want, build a legacy for you personally too, and to have time freedom to start enjoying life, frankly, whatever else you're seeking. And for some of you, now's the time, for example, to just focus on security. Maybe it's building a big solid bank account for retirement. We take these things super, super seriously. And it's my life's biggest reward to help you achieve them. I want to give you a free discovery session with our team. It's free. It's 15 or 20 minutes. You have zero to lose and everything to gain. And to understand how you might fit into the 3 Payday System that we've done now in over 80 markets as of this filming, go to smartrealestatecoachpodcast.com/discovery for a free call with our team.

smartrealestatecoachpodcast.com/discovery.

Because it's not whether or not you can do it or whether or not you fit. You can do it. It's whether or not you'll take action and do what it takes. And we can guide you through that process. smartrealestatecoachpodcast.com/discovery. We'll see you soon. Okay, so here's an interesting question, I think, in my brain. So I had on, I don't know how long ago, Ron Ferrucci. I'll put a little plug for him. And he gave like the audience— I didn't expect that he was an ex Used to run a REIA in Connecticut and then he moved and retired, but he had like, he's writing a book on it. I said, why don't you write a book? He said, I am. And it was all these hacks on how to run a property, right? It was pretty cool. Like I've been at the business 35, 34 and a half years and I, there was some cool things in there. So on your end, you've seen a ton of landlords, like you look over and you go, ah, I got this span of landlords now. Let's, are there any hacks? So I'll call 'em hacks that you can share that would help With reducing, I guess, tenant turnover is just that one lane. Any thoughts?

Yeah, there is. So one of the things we did over this past year was we said, you know, we've been around for like 10 years now. There's $30 billion in assets under management across all the landlords, all 50 states. There has to be some learnings in that that we can take away and say, what can we learn from those people? So we looked at Landlords on our platform that had multiple tenants, multiple tenants that had leases renewing for like 4 or 5+ years and tried to look at, okay, what is this individual doing differently than others, even in their same area, that they're able to retain tenants for significantly longer than others that seemingly have similar assets, similar area? Like otherwise everything would be the same. Like they have to be acting differently. And one of the interesting ones that we found in it was we talked to this one landlord. She manages 45 units today and had like over 10 tenants that were this style where she was keeping them for like 4 or 5 years and interviewed her, asked her like, what do you feel like you're doing differently? And we'll look and see based on our own data, does that match up? And it did. And what she said was, Response time on maintenance issues was her number one reason why she felt like her tenants stayed. And it was really interesting to hear her say it because it sounds logical at the time, but it's one of those things that I look back for our own chat as the way that we looked at our own support. And I love like the analogies of different, seemingly different things and how similar they actually are. And this was something we thought about really early on too, right? If You wrote in and we could help you respond really, really, really quickly, like a minute or less that we would reply in. You actually left that experience feeling better than if nothing went wrong at all, was the hypothesis. And it really did make people really happy. And she had applied the same thing to her own business as a landlord with her tenants. If you wrote in, of course you don't want the sink to break or something to go wrong in the unit, but if you feel like I'm there the moment you need me, Um, to resolve. And it doesn't mean it gets fixed in, in, you know, 10 minutes.

No.

But I at least reply to let you know I'm here, I hear you, I'm gonna find somebody for this, or I'm gonna send somebody over or something like that. Just that first response made a world of difference in terms of people feeling like, you know what, I am like, I'm almost happy something went wrong. Like, I'm, I'm happy to know that she's there for me if I need something. And I won't, I will actually try not to need something more often. And that was one of the things we saw. Like, it didn't actually like increase the amount of requests. It almost, makes you want to reach out almost like less, like because you know she cares, you empathize with her and things like that. So I think that's one of those like no-cost hacks that no matter what your system is today that you can do that makes a meaningful difference is that just initial first response time to somebody reaching out about an issue can make a world of difference when it comes to the renewal time.

It's a great reminder. I love it. Absolutely. Thank you for the nugget. How about along that line of like the hacks and the lessons learned, how about are there— what comes to mind? Let me say it this way. When I say to you, after all the landlords you see, are there like stupid, silly things you're seeing people do manually that you always want to like shake them and go, no, no, no, like you don't could do that.

Yeah.

That anyone would be affected by. What comes to mind?

Yeah. One of them is We ran surveys with our landlords over this past, we run them every year, but one of the biggest trends that we're seeing is on-time rent payments is becoming one of the biggest trends among landlords, basically because if you have stable cash flow, it avoids issues like missing mortgage payments that directly impact your ROI and other things like that. And so we were looking into like, what are some of the manual things? Exactly what you're talking about, right? Like what are some of the manual things you're doing that if you miss them, if you don't do them right, that end up impacting that on-time rent payment and ultimately your ROI. One of the painfully manual things that we see people do, at least, you know, pre-joining the platform, is like manual rent reminders, manual late fees, manually applying the rent. It makes a better experience for your tenant where it's automatic, then you're not doing it yourself. And you just come in, you set up your rules just like You would follow, you know what your own lease terms are. You upload your lease and we extract everything automatically for you in an instant. We've been able to basically apply AI to pull all the details out of your lease and set up your account for you. And at that point, it runs itself in terms of it never misses a rent reminder, it never misses a late fee application, it never misses running the tenant's autopay automatically. And we found that If you miss notifying your tenant on paying rent, they're 27% less likely to actually pay rent on time.

Wow.

You would think, right? Like if you have the money, you'll pay me on time. The reality is people are busy and there's a lot going on in their, their life and they, they, they intend to pay on time and then the first comes and goes and they, they just forget. Right? And if, if we can be that little nudge that says, hey, rent's due, or hey, we have autopay set up for you, so it just ran and you didn't even have to do anything. It means you get your rent on time more. It means ultimately you don't miss mortgage payments. You have better cash flow, better stability in your business, and a little more predictability when you're going to invest in that next unit.

I love it. This is cool because we have, I asked you about AppFolio because internally, Ryan, we have had AppFolio for a lot of years. And then we have a system where all the community members, because we rev-share, actually are in the back end of that. And then that's how they pay us on their profit, on their revenues. Worthless looking into. I appreciate it. That's why you see me scribbling notes.

I love it. I love it.

Give us kind of the vision. I mean, I honestly think everybody should go to RentReady, guys. RentReady, R-E-D-I.com. I for sure like every level listening. But in addition to that, or and what, what's next? Like, are there some cool things down the pike? Are you just scaling? Just share with them on that note.

Yeah, yeah. We're always evolving, always adding to the platform. I view it as like this continual, like, community build, right? There's new problems that have evolved over the years. I remember when COVID hit, digitally signing was not a question at all. No one had asked for it. We didn't have it. No one cared. And COVID hit and they said all of a sudden, hey, I don't want someone's hands on a piece of paper. I need to digitally sign. We built that. The same thing was credit boosting came out of that. We actually report your tenants' on-time payments to all 3 credit bureaus.

Oh wow.

So as long as they pay you on time, they're building their credit, right? And so it turns what is their biggest expense into actually one of their biggest benefits. They're actually like building their credit for the future, whether it's a car loan or one day a home loan or something else. And so we've seen meaningful impacts on their business. A lot of the way that we approach how we're building next is, will it have a meaningful impact on your business? We were able to see that we were able to boost on-time payments by 13% if we just reported rent to the bureaus. All of a sudden, your tenant was a little more motivated to pay on time instead of later. And so now I think the big one that's the, you know, just coming out in the last month and continually releasing updates that's beginning a ton of traction, it's only been out a month and we have thousands on it already, is tax season's coming up. We have built-in seamless accounting into the platform where you basically can just drop in all of your receipts over the course of the year that you've had. We'll automatically categorize them by Schedule E, give you profit and loss by property so you're not Like making sub jobs like you have to do in like QuickBooks or some other accounting-based platform. It just P&L out of the gate for you, all of the revenue tracked because your tenants are already paying your rent through the platform and all of like, you can manually track the mileage and even now going as far as connecting to your bank account. So we just suck in the transactions directly from there, categorize 'em for you. And ultimately, if you're working with an accountant, making them happy at the end of the year that you just give 'em access to the accounting portion of the app and they just go in and do their thing. Or you got your exports, you can drop them. But either way you go from, oh no, I have to spend my weekend gathering all of the things to give to an accountant or do my taxes myself to I click a button and I'm basically done.

That's awesome. Talk about competition. I, in a healthy way, I think you guys are going to crush a lot of the less efficient programs out there. So congrats Congrats to you guys. Ryan, anything at all that I didn't ask that a nugget, a piece of the, you know, that I didn't ask you about the software, anything at all that you want to share?

You know, I think the only thing is, you know, I love talking to people like yourself and people in your community that like have more ideas, things they want to see. We've even gone as far as we like automatically categorize, I mean, literally every chat that comes through that anybody mentions asking for anything we don't have, and it's how we prioritize what we're building next. So if there's something that, you know, you don't see on the platform today or a new problem you have even next week, next month, next year that wasn't even a thought in 2025 or 2024, swing by, let us know. And like I said, it's my biggest joy to get to create and build something that didn't even exist a year ago or 10 years ago at this point, that helps people ultimately be successful in their dreams and make an amazing experience for their tenants at the same time.

Well, I love it. And congrats again on your journey, the company's journey, and obviously how many landlords, investors you're touching, which was your earlier point when we started the show. So thanks again for being on, buddy. I really appreciate it. I'm going to work hard on getting you into some of the smart sit-downs and the things that we run, and we'll talk about that off air. I appreciate you being on.

I love it. Thanks again for having me, Chris. It's been a pleasure.

Okay, guys, that wraps up our time together today with Mr. Ryan Barone. What I want to do is make sure I— as of you listening to this podcast, March 4th, we are knee-deep in our In the Trenches boot camp right in our office here. And if you have no idea what that is and what we're doing, I want to give you 2 free things today. I want to give you, first of all, a couple of our bestselling books, Real Estate on Your Terms and Real Estate Deal Structure Overtime. Now just go to the number 3, 3paydaysbooks.com/podcast. That's going to get you the books. And guys, it's not a free offer where you got to put in shipping because I can't stand those free offers. Get my free book and you got to put in $8 or $10 for shipping. You won't put a credit card in for this. You won't put in 10 cents. We will ship it. Our expense. And if you're lucky, we'll put some goodies in there. It comes out of our office in Newport, Rhode Island. In addition to that, check out the master's class. Nobody's breathing down your neck. Nobody's pitching you anything. I just want you to see the workshop I'm doing. And at the end, I'll point you to some free resources. And for those of you that are more serious, I'll point you to the 3 Paydays system. Go to smartrealestatecoach.com/masterspodcast. You know, guys, for years I've been at the business now, 34, but for years we had some rent collection things in place, we had bookkeepers in place, we had marketing to go on all these different websites. Now we simply go to prosperity.io. It was built with us and you in mind. You can market your first property if you're brand new, you can scale if you're already in the business, but you can market your properties across 50+ platforms in one click for way less than hiring a pro. You can easily collect rent online, so it's like an escrow service for you. You can track payments, you can get monthly reports so you know how your investments are doing, or if it's your first investment. And no tech headaches, no guesswork, just smart tools to help you grow with confidence. Get started now at prosperity.io because every portfolio starts with a powerful first step. All right, thanks for tuning in to the Smart Real Estate Coach Podcast. If you got value from today's episode, guys, be sure to subscribe so you never miss a future episode. It literally takes one nugget to access some of the things we're doing. And when you're talking the amount of the size rather than the paydays, it's an opportunity cost that you can't let go. So don't miss an episode. And for goodness sake, share it with someone who needs to hear it. If you're ready to find your best path for getting started on your real estate investing journey in general, head over to smartrealestatecoach.com. We're going to help you take the guesswork out of your next steps. See you in the next episode.