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RentRedi's Ryan Barone: From Renter to $35 Billion in Assets

How Ryan Barone built RentRedi from an app he made to rent his own apartment into a platform landlords manage over $35 billion in assets on.

Most property management software was built by property managers, for property managers. That's the whole reason it doesn't fit the person who owns four duplexes and manages them at night after work. When I sat down with Ryan Barone, founder of RentRedi, for our conversation on The Owner Meeting, I found out his platform started from the opposite end entirely: he built it as a tenant who couldn't rent an apartment in New York City.

Today landlords on RentRedi actively manage over $35 billion in assets across all 50 states. Hundreds of thousands of landlords and tenants use it every day. Ryan wrote all the original software himself, answered every chat message and phone call for the first three years, and still hops into live chat when the team is short-staffed: where, as he put it, he now has to convince people he isn't AI.

Here's what he shared about building it.

The Gap Between One Rental and Fifty

I asked Ryan for the 30,000-foot view first. RentRedi is an all-in-one platform that lets anybody manage their rentals more simply, affordably, and successfully than they could otherwise. The design goal is that you can start with a single-family home and scale to hundreds of units without ripping up your systems along the way.

Rent collection, finding tenants, screening them, accounting, communication, maintenance: everything you actually have to do once you own the thing and you hit that moment of "okay, now what do I do."

That gap is real, and it's a massive problem for landlords. There's software designed for a handful of single-family rentals, and then there's software where you effectively need 50-plus units to qualify and it gets really expensive. A solution that runs from A all the way past Z is not common.

When I asked Ryan what success looks like for a landlord on his platform, he didn't lead with features. People have invested their life savings into these properties, and what they want out of it differs: more time with their kids, equity so they can retire early, cash flow so they can take extra vacations.

What the platform does is make that more likely: rent on time more often, shorter vacancy periods, fewer evictions, fewer maintenance headaches, fewer calls in the middle of the night. And with April approaching at the time of our conversation, he made a point about tax season, not scrambling for receipts and wondering how to categorize things for a Schedule E. Instead you open a platform that has P&L by property out of the box, in real time, with no work done on your end. Rent collection on autopilot. Maintenance handled by you, a teammate, or outsourced through the platform.

All the oversight and control, with the manual spreadsheet work automated away.

Why Building for the Tenant Changed Everything

There are a lot of platforms in this space. I asked what makes RentRedi different, and the answer came back to where it began.

Ryan started solving this problem for himself as a tenant. He doesn't even like the term "property management software," because it was intended for property managers, and that's not who RentRedi is for. It's for DIY landlords: the individuals who own and operate their own properties and say, "I want the better return of managing it myself, but I don't want the headache of managing it myself."

Because he was building for himself as a renter, he wanted an experience in a unit where he was happy to live and happy to renew. That turned out to be a durable advantage. When you have one, two, five, ten, even 25 units, an individual tenant saying "I love this platform, it helps me build my credit, it's easy to pay rent, I set up autopay, I know when my roommates have paid" matters enormously. The flip side is just as true: if your tenant hates the tool and wants to use some other method, at that scale you often end up switching.

I told him this is the part I find genuinely clever. Ninety-nine point nine percent of software designed for landlords only addresses the landlord-specific issue: rent collection first, then user interface, then accounting. But multifamily is a very simple business. We provide housing for humans. That's the supply and demand curve. Half of that equation is the tenant. That's your client and your end user. Designing from the bottom up instead of the top down means that if your tenants like the software, they like renting from you, and that cascades into everything else in property management.

Three Years of Answering Every Single Chat

Ryan and his co-founder (who is his father) personally answered every chat message, every phone call, and every demo for the first three years, while Ryan wrote all the software himself.

His framing of why that mattered: it meant the platform didn't come from "I want to manage my rentals this way and everyone has to conform." It came from "I have no opinion, I want to solve the pain for other people: tell me what problems you have and why these long-standing solutions don't work for you."

And when he talked to landlords, 80 to 90% of them were on pen and paper and spreadsheets. There was a reason they weren't adopting the existing platforms.

He even went to major property managers in New York City to ask what they used and why. One told him, "Hey, it's a great idea. We just invested $5 million to build our own platform to manage our rentals." Ryan's takeaway: the average landlord can't spend $5 million building their own tools, but the fact that a firm at that scale felt the need to says everything about the gap in the market.

Every feature on the platform today came from that bottom-up process. He gave me one example I loved. A real landlord in Texas called him on a Friday night: "I'm going through an eviction. If they pay me even a dollar on rent, it resets my eviction clock. I need to be able to block partial payments on a tenant-by-tenant basis, or outright." Overnight, they built it and released it. That landlord was set on their eviction.

You cannot recreate those stories starting top-down from a feature set page and a pricing page.

This is the core of entrepreneurship: identify the problem, solve the problem. My own view, which Ryan agreed with, is that every CEO and every owner should spend at least 90 days working the customer service part of their business. If you don't understand it, that's where companies miss the mark: they build an awesome product that solves a problem, just not the core problem.

Ryan argued it never really goes away. A couple of weekends before we spoke, his team was short on a call-in shift, so he hopped into chat for a few hours without telling anyone who he was. He still calls landlords on the platform, from brand new users to five-year customers. He recently did a podcast where the host had been on the platform for three years and grown from five units to 50.

His point about feedback stuck with me. Every question someone asks, you can answer for that one person, or you can ask how to change the business so no one ever has to ask it again. The next person who walks in says, "oh, that's so intuitive." Well, it wasn't intuitive. Somebody asked before you got here.

The Actual Starting Point

I wanted the real origin, because these stories are what convinced me it was possible when I had no money.

Ryan grew up in a small town outside Albany, New York, and came to New York City for college. He majored in economics and math with a computer science minor. He got his first internship at Goldman Sachs: a firm he'd never heard of until about two weeks earlier, when he walked past a talk they were giving at Pace, saw pizza outside, and went in. The room was at capacity so he sat on the floor and listened. They said you can apply, and he had a resume ready because his economics professors had insisted on it.

When Goldman called to schedule the interview, he actually told them he had a midterm the next day and tried to hang up. A friend a couple of years older asked who that was, then told him to call his professor, who would absolutely tell him to skip the midterm. He did, and he got to interview.

That internship was his chance to move out of the dorms and get his first apartment. And he found it was pretty easy to find a place to rent, but not easy to actually rent a place. All the industry effort had gone into the search side, not the application, the living there, and the wanting to renew.

So he built an app for himself and his friends to apply to apartments more easily. Not as a business. And he deliberately didn't change the landlord side at all, assuming landlords were happy and didn't want their process messed with.

Then he started submitting applications through it, and landlords asked him why he'd only fixed his own side. "Our side's way worse than your side. You're just seeing the trickle-down effects of this as a tenant."

That's where he fell in love with building for both sides. Landlords started telling him what they actually wanted:

  • "Application is great, but I'd like pre-qualification so I can spend my time with the best five tenants instead of the first five who reach out."
  • "I don't care about screening. I don't want a 2 a.m. call about a dripping faucet: send me videos of maintenance issues so I can decide whether to get out of bed."
  • "I just want to get rid of the check-is-in-the-mail excuse and know the instant somebody pays me rent."

From Side Project to Company

Ryan described roughly three phases. First, building it for himself and friends. Then the moonlighting phase: he graduated, went to work at PwC, and came home to work on this until three or four in the morning, every single day.

He drew a parallel I thought was sharp: his moonlighting was RentRedi, and for the landlords on his platform, their moonlighting is their rentals. Same thing.

The tipping point came when a college friend who'd landed an internship at a venture capital firm invited him to pitch at a competition. Ryan's reaction was, "It doesn't even work yet." He hadn't finished the first version.

That, for the record, is the best time to start selling. The time to pitch is concept, not finished product: the easiest way to pitch is when you already have clients.

He didn't get investment that day. There were too many holes. But he got follow-up conversations and enough confidence that there were legs to the idea, and that there was a massively underserved segment of independent DIY landlords and their tenants.

He left PwC in 2016 to work on RentRedi full time, moved into a friend's basement in Hollis, Queens, and eventually moved back home. For about two years he built with almost no customers. He's a saver at heart, and this was the first time in his life he looked at his savings and thought: if I spend all of it making this work, it's worth it. He burned through nearly everything.

Then traction hit. Landlords were excited enough about it to tell other people, and excited enough that they became his first investors. The first money RentRedi ever raised didn't come from a venture firm. It came from landlords on the platform asking him whether he was raising.

Zero to One, Then One to a Hundred

On marketing, Ryan splits it into getting from zero to one, and then one to 100.

Zero to one was brute force. Dozens and dozens of meetups (in the city, out in New Jersey, Pennsylvania, upstate around Albany) just talking to landlords about their problems. For the first 100 to 150 landlords on RentRedi, he and his co-founder were the only people at the company those users ever talked to. He doesn't even think of it as marketing. It was talking to people about what they needed solved, figuring out whether he already had it, and changing the product based on the answer until the answer was yes.

The shift came with their first venture round. Up to that point he was largely self-taught on the engineering side, and he and his father had figured everything out themselves. Raising money meant they now had other stakeholders and had to make it work: so they brought on people who actually understood marketing at scale, including their first main marketing hire, who's been with the company about seven years.

One detail from that round stuck with me. The fund leading it interviewed about 20 randomly selected landlords from the platform as diligence, and asked hypothetically how they'd feel if RentRedi were taken away. People were swearing at them. The investors had to explain they weren't taking it away: they just needed to know whether it genuinely helped. They called it some of the best diligence they'd ever done.

Which turned the question into the real one: can you make people just as happy at 1,000, 10,000, 100,000, or a million users as you can at 150, when they're getting to talk to the founders directly?

Keeping Quality at McDonald's Scale

Ryan's analogy for this is food. Nothing beats home cooking from your grandmother, made for you and only you. Then you get to restaurant level, doing it for 20 or 50 people in a room. Then McDonald's scale, doing it for millions across the world. Can you keep the quality you had at the start?

That's extremely hard to do. One of my favorite business movies is The Founder, about Ray Kroc and McDonald's, and the biggest issue in franchising was exactly this: quality control took them forever to figure out.

Ryan's answer had two parts.

First, you have to do it yourself at the beginning. If you never did the work, you can't hire people to do it, and you can't iterate with them on improving it. Ideally things get better, not just held at status quo: you hire really smart people who start asking why you do it a certain way, and you realize the honest answer is "because it was just me in a basement and no one was around to question it."

Second, hire people who genuinely care about the problem. He wasn't speaking hypothetically: a lot of people on the RentRedi team own rentals themselves, manage them on RentRedi, bought their first properties on RentRedi, and use the company's own blog to look up things like move-in checklists. Some had parents who sold a portfolio to put them through college. Some have been tenants on the platform. Those people proactively ask how things could be better, which adds another layer of the same feedback loop the landlords and tenants provide.

The Stupid Tax He Paid

I ask every guest the same closing question: what's the highest stupid tax you paid: the thing you didn't know when you started that you had to pay to learn?

Ryan's answer: even after that pitch competition showed there were legs, he didn't go sell the concept. He spent about two years building the whole thing and trying to perfect it without getting it into people's hands.

In retrospect, he'd have built less and released earlier, and used that to iterate faster.

That lesson now drives how RentRedi operates. If you ask for something the platform doesn't do, they legitimately record every single feature request (not the "we'll pass it to the product team" version) put it in a list, and it gets voted on. They review your exact words about how you wanted the thing to work, so when a hundred people ask for something, the way they build it reflects how those hundred people described it.

I told him that's the one thing I think I got right across six or seven businesses: I never had money to develop a product, so we always sold units in concept first and then made the product match what we'd sold. Starting with revenue is easier. Doing it for two years without customers is genuinely hard: the whole time you're carrying "what if this doesn't work and I spent two years for nothing."

Which is exactly why his bigger lesson lands: just start. You'll learn more from putting a little of it into the world than from planning behind closed doors for the perfect plan. And whatever you learn, you'll do faster the second time.

I gave him a real example of that. An investor in one of my recent deals built a medical practice over seven years, got it multi-state with 30 or 40 employees, and sold it with a big exit. Several years later he built the same company again: four states, 150 people, sold for roughly seven times as much. More than twice the business in less than half the time, because you learn along the way. Even when you pay the stupid tax, you've bought the education.

Ryan's feature-voting approach also lines up with something from Ray Dalio's Principles, one of my favorite business books: running the company as an idea meritocracy, where everyone from the lowest-level client to the top has a voice. As Ryan put it, referencing The Wisdom of Crowds: instead of a property manager building software around how they personally manage, what if hundreds of thousands of landlords voted on the right way and you built around that? You get a better output, not because you're smarter, but because you put all those brains together.

Key Takeaways

  • Build from the end user up. RentRedi started as a tenant's app, and happy tenants are what keep landlords from switching platforms.
  • Do customer service yourself first. Ryan and his co-founder handled every chat, call, and demo for three years: that's where every feature came from.
  • Talk to the people not using existing solutions. Eighty to ninety percent were on pen and paper for a reason.
  • Pitch at concept, not completion. Ryan's biggest stupid tax was two years of building in private instead of releasing early and iterating.
  • Your happiest customers can be your first investors. RentRedi's first raise came from landlords on the platform.
  • Quality at scale comes from doing the work yourself first, then hiring people who genuinely care: many of RentRedi's team own and manage rentals on the platform.
  • Record every feature request in the customer's own words and let them vote. Crowds make better product decisions than founders do.

Watch the full conversation for Ryan's story in his own words, including the Goldman Sachs midterm and the Friday-night eviction feature. RentRedi is at rentredi.com: live chat and demos are available on the site, and it's open to tenants too. Details on our mentorship are in the description, our free multifamily course is at multifamilystrategy.com/get-free-training, and the free Multifamily Strategy community on Skool comes with a deal calculator. On this podcast we interview owners of businesses and real estate who are already doing the thing you want to do: I'll see you on the next episode.

Read the episode transcript

Original automatic captions. Names, numbers, and punctuation may contain transcription errors.

0:00 Welcome back to the owner meeting podcast hosted by multif family strategy. I'm Christian your channel host. Today we have Ryan Baron with rent
0:06 ready. This is a company I am very familiar with and it's talking about my favorite topic of all time. This is
0:13 about optimizing your rental. This is an all-in-one platform. Ryan's story is absolutely awesome. So super excited to
0:19 have him. Ryan, welcome to the pod. Thanks for having me, Christian. I'm excited to be here. I'm super excited to have you. I when I
0:26 when I saw your name come up and I saw Rent ready, I'm like, "Yes, yes, this is a this is a solid business that I am uh
0:33 I'm really excited because I actually going into this, I know a little bit from research, but I actually don't know a lot of the backstory." So, I will be
0:40 learning right along with the audience for so much of this and I am really excited for that. Absolutely. Ryan, really quick, for those unfamiliar
0:48 with Rent Ready, give us the 30,000 foot view. What is Rent Ready? Who are you?
0:54 What are you doing? And then I want to get right into your backtory. Yeah. Yeah. Yeah. Happy to. Um, so RER Ready is essentially an all-in-one
1:01 platform that allows anybody to manage their rentals uh more simple,
1:07 affordable, and and more successfully than they would otherwise be able to do. And largely we've designed it in a way
1:14 where you can start with as little as one single family home and scale to hundreds and you're not like ripping up
1:20 systems and uh trying to figure out a new way while you're trying to scale. instead from really day one through uh
1:27 scaling all of that, you can handle rent collection and finding tenants, screening them, handling your accounting
1:32 and communicating with them, maintenance, and basically everything that you would actually need to do to run your rental successfully once you
1:39 own that thing and you have that moment of okay, now what do I do? Um that's where we come in in terms of giving you
1:44 the tools um to basically let you do that yourself. um as well. Well, that's a huge problem that that
1:50 just right there. That's a massive problem for landlords of there is software that is designed for, hey, I
1:56 have some single family rentals or a really small portfolio. You get into other software that's like, hey, you have to have 50 plus units to get here
2:02 and it's really really expensive. Uh having a scenario from a to way past a
2:08 to as large as you want to get, that's actually not very common. What what does what uh help define successful rental as
2:16 a landlord? like what what the core problem that you're solving with Rent Ready, what does that look like? Success
2:22 for a landlord. Yeah, for a lot of people, you know, they've invested their life savings into buying these rental properties. And uh
2:28 it differs for different people on the platform. Um but a lot of it is um either spending more time with their
2:34 kids or being able to build equity in those rentals so that they can retire early someday or build cash flow so they
2:40 can go on some extra vacations. Um, and ultimately we're helping ensure that they get their rent on time more often.
2:47 They minimize their vacancies periods. They have less evictions. Um, they ultimately have fewer maintenance
2:53 headaches. They're getting less calls in the middle of the night. Um, they're I know we're we're doing this close to
2:58 April time. They're not scrambling at tax season going, "Oh no, where are all my receipts and how do I categorize this
3:03 for my schedule E?" That that's just handled for them. And Exactly. Exactly. So, you know, uh it's
3:10 letting them instead come into a platform that has something like P&L by property out of the box in real time
3:16 when they've done no work to to figure any of that out. Um and their rent collections being done on autopilot.
3:22 Their maintenance is handled by themsel or a teammate or just outsourced um through the platform. And um ultimately
3:29 they get to rest a little easier at night knowing their rentals are are being run well. They have all the
3:35 oversight. They have all the control, but they have a system to automate all the manual tasks that they would have otherwise done on spreadsheets.
3:41 Oh, that is that is perfect. And there there is right now in the marketplace, there is a ton of software that does
3:48 this. I think a lot of people are hearing this if you're brand new to this. Okay, so it's so it's property management software. It does it does go
3:54 beyond that. What makes you different than the you know the 50 other solutions out
4:00 there for automating property, right? What is what makes Rent Ready unique? Yeah, there there's a lot of them. Um I
4:06 I do think one of uh you know a few of them are um I actually started trying to
4:12 solve this problem for myself as a tenant first. Uh I think that's one of the biggest mistakes that uh software in
4:17 our industry misses is that traditional property management software. And part of the reason I don't even like the term
4:23 of it is it it was intended for property managers. And that's really not um what Ren Ready is built for. It's built for
4:29 the DIY landlords, the individuals that own and operate their own properties and say, you know, I want I want the better
4:35 return of managing it myself, but I don't want the headache of managing it myself. Yeah. Um, and so when I started
4:40 building Rent Ready, I was trying to solve my own problem as a tenant who couldn't get an apartment uh in New York
4:46 City here and because I didn't have all my documents together. And I initially built an app for myself and friends to
4:51 apply to apartments more easily. And um it wasn't until I started bringing it to those individual landlords that said,
4:57 "Hey, our site's way worse." Basically, we have to be, you know, 50 units plus
5:02 to use the traditional property management softwares out there. Um and largely they're not really designed in a
5:10 way that fits for us. It it I'm taxed for my growth. Um so it it basically
5:15 eats into my margins as I grow. And one of the the things that I still keep coming back to this day about which was
5:21 a bit by chance was because I was building it for myself as a tenant like I wanted a great experience in a unit
5:27 where I was happy to live there. I was happy to renew. I didn't want to live anywhere else that it's been really
5:33 interesting to see where when you have 1, two, 5, 10, even 25 units.
5:38 An individual tenant telling you, "Hey, I love this platform. It helps me build my credit. It's easy to pay rent. I set
5:44 up my auto pay. I know when my roommates have paid and when I have it, so you're not chasing me. Like, it just runs super
5:50 smooth. It's better for you. And vice versa, if your tenants's like, I hate using this and I just want to use some
5:55 other method. A lot of the time you'll have to switch um when you're at that scale. And so, it's been a huge
6:01 advantage for us growing as a platform. We're over $35 billion in assets,
6:06 landlords actively managing in all 50 states across the country from not just like New York City where I started, but
6:12 like rural areas, small towns like I grew up in originally. And um it's been really exciting to see. And I think a
6:18 big part of that is that to me it's a it's a two-sided marketplace where you have when you have really happy tenants,
6:25 you have less headache as a landlord. Um, and you get to ultimately be a little happier uh about running your
6:31 rentals and enjoy uh the fruits of your investment and everything too because what you're what you're solving I would
6:38 say 99.9% of any other software designed for landlords only addresses the
6:44 landlord specific issue. So at least in its original design. So it's designed for let's go rent collection first, let's go
6:51 uh user interface, let's go accounting and all stuff that your software does. But starting from the perspective of
6:57 it's a very simple business multif family housing it we're providing housing for humans like that's your supply and demand curve like how how
7:04 many houses how many humans need housing that it's a very basic business half of that equation is the tenant like that is
7:10 your client that is your end user so it's really cool designing this from the bottom up instead of the top down I
7:17 that's where all the revenue is so building a platform like hey this is tenants wants to use this that
7:23 automatically gets you a I I'd have to imagine that that gains you a lot of market share of like, hey, tenants are
7:28 familiar with this platform. It's designed for the tenants. If my clients like using that software, they're going to like renting from me. That starts a
7:35 whole cascading events of like good stuff in property management. Uh, so I I I love that. That's that's cool that you
7:42 are a you started it as a basically as a as an enduser of the product as opposed
7:47 to as the landlord. I think that's a really unique take on this. Yeah. and really every iteration along
7:52 the way. I think one of the big differences as well in terms of how we built the platform. The first three years of the business, I personally did
7:58 every single chat me and my co-founder like two of us answered every single chat message, every single phone call,
8:05 every single demo. I wrote all of our original software personally myself for the first three years of the business.
8:11 So it wasn't coming from a place of saying you know I want to manage only my rentals this way and everybody has to
8:17 conform to my way of managing rentals but instead saying I have no opinion I want to solve the pain for other people
8:24 and so you tell me what is what are the problems you have and why do you have them and why do these other solutions
8:29 that have been around for a long time not work because you're not using them largely when I talk to people you know
8:34 uh 80 90% of them are on pen and paper and spreadsheets and so there was a reason that they were not adopting these
8:40 platforms And largely, you know, there was that tenant aspect of it, but there was also like there were a lot of people
8:45 that said like, I wish I could build it for myself. And um this isn't just on the small end. I remember going to um
8:52 some of the major property managers even in New York City and trying to ask them like, "What are you using? Why are you using it?" And I remember meeting with
8:58 one of them in New York City and said, "Hey, it's a great idea. We just invested $5 million to build our own
9:04 platform to manage our rentals." And I'm sitting there going, "Okay, the average landlord can't invest $5 million to
9:11 build their own platform." But this is telling that even at like their scale, they're seeing a gap in the marketplace
9:17 for needing to do it themselves. And so largely everything on the platform, any
9:22 feature that exists on the platform today was not because we went like top down. Like you said, it's it started bottom up in terms of talking to
9:28 individual people, landlords and tenants both, and saying, "What's the individual problem you have? Why do you need that
9:34 solved?" and then we'll implement something that solves that. And so it goes as minute as something like
9:39 blocking tenant payments where a landlord called me up, a real landlord called me in Texas at one point and said
9:44 on a Friday night said, "I'm going through an eviction. Uh if they pay me even a dollar on rent, it resets my
9:50 eviction clock. And I need to be able to block partial payments on a tenant by tenant basis or outright." And like
9:56 overnight, we had this built in the platform, released this landlord, they're all set on their eviction. But it like it's those individual stories
10:02 that I think you just can't recreate when you start top down and say like how do I build like a a feature set page or
10:09 a pricing page for a property management software versus when you say I'm not trying to build property management software. I'm trying to solve problems
10:16 for landlords and tenants that are self-managing their units. You tell me what your problems are. you tell me how you want them solved and I'll makes it
10:23 make it flexible enough that whether you're in, you know, Charlotte, North Carolina or Texas or California or North
10:30 Pole, Alaska, which I found out from a real landlord on our platform is a real place that they are managing properties
10:36 that you can do it. It's flexible enough to to manage it your way, but managing your way doesn't mean you actually have
10:42 to like handle everything in spreadsheets and text everybody to remind it and set all these reminders and calendars and get all these calls in
10:48 the middle of the night for yourself. I think that just goes back to the core of entrepreneurship like that that at the end of the day that's what it is like
10:54 right we're identifying the problems and we're solving the problems and I've seen this in a lot of the one they're my
11:01 favorite people to interview so this is I'm already excited but when you when you actually build a business really from the ground up where you're like hey
11:06 I yeah as the owner of the company I started as I was the customer service department
11:11 like me and a business partner those are and then as your company gets bigger and bigger like those are the
11:16 days that you look back on like it was really hard And but you look back on those things and you're just like, man,
11:21 I remember how fun and exciting and difficult that season was. As an
11:27 entrepreneur, you can't replace that part of the business where you're like, hey, I was in every single role. I I
11:35 think every CEO of a company and every owner of a company should have I mean it minimum 90 days, but like you should
11:41 have a season where you work the customer service part of your business. And if you don't understand it, that is
11:47 where a lot of businesses miss the mark. They have an awesome product that doesn't quite solve the problem because
11:52 they weren't working on the core problem. They were working on a problem. So super Yeah. I I I love I love hearing
11:59 argue it doesn't go away. Like still to this day, um like a couple weekends ago,
12:04 we were like short on on on a a call in. I was like, you know what? I've got a few hours. I'm going to hop in on chat.
12:10 Like answer some chats. And literally like I didn't tell anybody who I was. just answer some chats and handle.
12:16 I still call landlords to this day. Um I have to convince them that I'm not AI at this point now. U but I call people on
12:23 our platform whether they range from like brand new or they've been with us for five years. Um was just doing one
12:29 podcast recently where the actual host was had been on the platform for three years. He grew from five units to 50
12:35 units on the platform. Um you know I I I think that uh that learning experience
12:40 doesn't end. I feel like like you said like you'll you'll get to a point where you can't do it uh a 100% of the time
12:46 anymore. It might be like you know once in a a week or once in a month or something like that. But um being able
12:52 to stay close enough to say I just want to hear some of the direct feedback of in any business uh it is just be able to
13:00 hear that direct feedback of how people are thinking about problems even when they don't necessarily think they're
13:05 like giving you feedback. They're just asking questions and like every question someone asks, you can come away from it
13:10 going, "Okay, I could answer that for that one person." But also, how do I how do I change the way I'm approaching my
13:16 business so that no one ever has to ask that question again? And so the next person that comes in is like, "Oh,
13:21 that's so intuitive." And it's like, "Well, it wasn't intuitive. Christian just asked the question before you were here, and then we changed it to make it
13:28 intuitive for him, and that's intuitive for, you know, the next person that came in the door." Yeah. Well, I'm I'm I'm curious about uh
13:35 even even before I want to go back like one step further. You mentioned that you're originally from a smaller town,
13:40 right? Yeah. Yeah. Okay. I'm I'm I'm curious about this. My uh all of my posts recently, so but my
13:46 home state was Washington state and they just passed this 10% millionaires tax.
13:51 So basically it's a it's basically just a tax on like if you own a business and it happens to be successful uh we we
13:57 want uh 10% of everything that you make over I think it makes the effective tax rate for a lot of millionaires like 51%
14:03 or greater now uh it's like really controversial. So a lot of my channel
14:09 has been people being upset at me for creating a successful business. A lot of us do start from small towns or in your
14:16 case you started as a tenant. I I want to hear the actual starting point because when I hear these success
14:22 stories in businesses, this inspires me. Like as Yeah. Yeah. As someone who spent most their life
14:27 without any money, it's really it this is the type of stuff where I'd listen to this like,
14:32 oh, it is possible. I would love to do that. Uh solve a problem and solve it
14:38 well enough that you actually have monetary benefit. That's amazing. Uh where where was your actual starting
14:44 point? What did the very beginning look like for Ryan? Yeah. So, uh, I I grew up in a small town outside of Albany, LA,
14:50 New York. Um, I came to New York City really for college initially. I I majored in economics and math and
14:56 minored in computer science. And I had gotten my first internship uh at Goldman Sachs, which I didn't even
15:02 know what Goldman Sachs was until like two weeks before was just they were doing a a talk at one of the floors at
15:09 Pace and I walked by, they had like pizza outside, so I was like, I might as well go in. I literally like sat on the floor cuz they were already at capacity
15:15 and just like listened to them talk about this. They said you can apply. So I I had a resume like my economics professors at the time had we said like
15:22 you should have one of these ready which you know I give them credit for. And that's funny you were studying economics. You're like what's a Goldman
15:28 Sachs? I didn't know at the time. I was I was only uh I I was pretty young. I was only
15:34 going into I was in sophomore year going into junior year. So I wasn't really even thinking about internships for
15:39 probably like another year after that. But I thought why not just like throw my hat in the ring and see how it goes. And
15:45 that was awesome. Um was lucky enough to get the the call uh to uh to interview
15:50 there. Um also again really not prepared to interview places. When I first got
15:55 that call I actually said I'm sorry I have a midterm tomorrow. I was like in the library with a group that I was uh
16:02 studying with and I said oh I can't come in for an interview. I I have a I have a midterm tomorrow. trying to hang up and
16:08 my friend who is luckily a couple years older said who was that it was Coleman Sachs they asked me if I could come in for an interview but I've you know
16:14 Professor Coleman's uh midterm tomorrow he said skip his mid call him he will
16:19 tell you to skip his midterm you can go in for the interview so I did reach out to him and say can I can I miss this uh
16:26 midterm and like take it you know a couple days later or something and he said yeah so I did get to go in and
16:31 interview for that but that was my chance to move out of dorms and get my first apartment and I thought it would
16:36 be super easy to just like find a place. I felt like it was pretty easy to find a place to rent, but it wasn't very easy
16:42 to actually rent a place. And I feel like that was the disconnect where so much time had been spent on kind of the
16:47 search side, but not the actually application and then living there and
16:52 wanting to renew there. And so I initially built an app for myself and friends just to apply to apartments, not
16:58 as a business, but just as hey, this would make things easier for us. and intentionally did not change the
17:04 landlord side at all, thinking that landlords were happy, everything was great for them and very easy for them
17:10 and they really didn't want their process messed with. And it wasn't until I started using that to submit to some
17:16 landlords that they were saying like why are why did you only change your side? Our side's way worse than your side.
17:21 You're just seeing the trickle down effects of this as a tenant. That was really where I started to, you know, get to fall in love with uh building it for
17:27 both sides where I said, "Hey, you know, application is great, but I'd really like a pre-qualification so I can spend my time with the best five tenants
17:33 instead of the first five tenants that reach out to me. So, can I pre-screen these people?" Or, "I don't care about the screening at all. I have tenants in
17:40 my unit, but I don't want to get a call in the middle of the night for something that's a a dripping faucet and can
17:45 handle it tomorrow. So, can you send me videos of maintenance issues on the platform so that I can determine if I
17:50 need to get out of bed at 2 a.m. or if it can wait till the next day? Or someone else is like, I don't even care
17:55 about the maintenance side. I just want to get rid of this check is in the mail excuse. And no, the instant somebody
18:02 pays me rent. And there's no question about it. And same thing for their roommates and and and a lot of stories along the way that that you know
18:08 impacted different portions of the platform. But but that's really where it all began. When did it become a business? I'm It's
18:15 so hard for a espec degree had a job. It's like that's like the hardest place to become an entrepreneur. It's very
18:21 easy to be you know you buy in like I got a job I'm working I don't need to be an entrepreneur right you don't have to
18:27 do it. When when did this go from like hey this is a project I'm interested in to this is a business or did you start as like I
18:35 am going to start this and I'm going to solve this problem. What which uh what was your entry to I'm an entrepreneur
18:40 now. How did how did that change happen? Yeah. So I I think there was probably maybe three or so phases of this. There
18:46 was like the initial phase where I was just building it for myself and friends. Um there was a tipping point. I I
18:52 graduated college and then I was working on this this I was eventually working at PWC, get off work, work on this till
18:59 like 3:00 4 in the morning. Um and then do the same thing the next day every single day. And that's where I feel like I really resonate with the landlords on
19:05 our platform. Like my moonlighting was rent ready. Like their moonlighting is their rentals, right? I really feel like
19:11 it is the same thing. And I got to a point where um it was actually a friend of mine that I had met in college had
19:18 gotten this uh internship at this venture capital firm and said, "Hey, we're doing a pitch competition. You
19:23 want to come pitch your idea?" I was like, "It doesn't even work yet, right?" Like I was still at the phase where I was I hadn't finished the first version
19:29 of the app. I was That's the best time to start selling. By the way, entrepreneurs, take take notes. The the time to pitch is concept,
19:36 not uh Yeah. Not Not like, "Oh, I have a finished product. Let's see how the market thinks. Like the easiest way to pitch a
19:42 product is when you already have clients. You are so right. And so I I went and I pitched there and ended up getting
19:48 follow-up conversations with people. Did not get investment at that point in time. There were too many holes and problems I needed to solve. But it gave
19:54 me enough confidence that like there was legs to this idea. There were there was actually this massively underserved
20:00 segment of both independent DIY landlords and their tenants. And if I
20:05 could create something that would actually help both sides of that, um it it really would help a lot of people.
20:11 And I thought that was really fun to focus on that that uh segment of people. And so um I ended up leaving um in 2016
20:19 uh PWC and started working on Rent Ready full-time. I moved to a friend's basement in Hollis, Queens and
20:25 eventually ended up moving back home for a year and for like two years was building Rent Ready um almost with like
20:31 no customers. Um, and it really took like a couple years before we started getting our first customers on the
20:36 platform. But I really felt like for the first time in my life that it was something that I could see, you know,
20:42 I'm I'm inherently like a saver at heart, I think. And so I like, you know, I've been saving my money for something. I didn't really know what, but that was
20:48 like the first time where I was like, if I spend all of my money making this work, it's worth it. And so, um, I
20:55 burned through dear nearly everything. got to a point where we started gaining traction with landlords on the platform.
21:01 It was really like we hit that threshold where it's really solving their pain points and they were excited to be on
21:06 the platform and excited to tell other people and in fact so excited they got to a point where they became our first investors on the platform where the
21:13 first money we ever raised wasn't like from a venture capital firm or anything else. It was actually from landlords that were using the platform that said
21:19 to me like, "Hey, are you raising money?" I was like, "Sure, yes, that'd be great to raise money." And it it let us expand more and
21:27 uh go on later to to end up raising more money and growing the team more and you know getting the scale we are today
21:33 where you know hundreds of thousands of landlords and tenants are able to use the platform every day and make things
21:38 easier for themselves. That's so that's so cool. Back go back to the early stages of marketing. This
21:44 is something Yeah. And by the way if if you happen to be a listener and you're like hey this
21:49 is a cool episode. It is. I love this episode. But the entire podcast, this this is all about meeting owners who've
21:55 done the thing that you want to do. And so it you don't have time to do that owner meeting because you're doing the
22:00 same thing. You're starting your moonlight. You're buying your portfolio. You're building a business. Like this is the this is the core stuff here. I'm
22:07 super curious about the marketing. When you first started marketing this, so you went from concept uh you're you're an
22:13 employee, a student. where at what point did you like start actually marketing
22:18 and how did you get your brand out there? Marketing is a bear of a project to learn uh especially if you started as
22:24 an employee and a student. Uh I went to college for business as well. Uh the
22:30 only class that I got a C in and barely I barely got a C was marketing which is
22:36 crazy because marketing is like the thing that I've been most successful at in my career and I've used nothing from
22:41 school. So my experience has been marketing is ever evolving. You have to figure it out. How did you start
22:47 figuring out? Okay, I now have a product. I have people who are interested in the product, right? You have some clients. They're like, hey, I'd invest in this idea. How do you get
22:54 this idea to hundreds of thousands of landlords? I think there's there's a in my mind
23:01 getting from like zero to one and then one to 100, right? So from like zero to
23:06 one was kind of brute force. It was just I mean going to dozens and dozens of
23:12 meetups um whether they were like directly in the city or out in New Jersey or Pennsylvania and talking to
23:20 different landlords upstate around Albany um trying to just understand like what your problems are how do we solve
23:25 those work with those individual people like support them directly for the about the first 100 to 150 landlords on rent
23:32 ready I myself and my co-founder were the only people they talk we were the only people at the company right that they would talk to so it was just like
23:39 brute force in the beginning in terms of understanding uh what their problems
23:44 were talking to them. I don't view it as like even marketing to a sense. It was
23:49 just like talk to people about what they needed solved and figure out do I already have that or is there something
23:54 that needs to change in that and then changing it based on that feedback and eventually the answer was yes, right? And so um that was the approach for
24:01 about 150. We got to the point where we were raising like our first uh venture round and I think that was kind of the
24:06 tipping point where we're bringing in money. We we do in fact have to make it work and now now it's not just you right
24:12 now. Now it's like okay I have other I have other stakeholders has to happen right and so going into that round and I
24:18 give I give him a lot of credit like going into that round right I was just uh on the engineering side viewed as
24:23 like mostly self-taught uh programming just spend all of the hours you need to
24:29 to figure it out the same the old school we're building a platform
24:35 and it is really hard right right and so you know up until that point like myself and my
24:41 co-founders like my father I I I when starting Rent ready he was like hey do you want to do this with me? Um, and so
24:48 he started doing it with me and we had kind of just figured it out ourselves up until that point. And when we raised
24:54 that money, we planned to bring on some great people that really understood marketing to be able to do it at scale.
25:00 And um, like Kellu's on our team has been with us for like seven years now. Um, and was really like the first main
25:07 marketing hire that we did um, at the company to start promoting it out to uh,
25:12 landlords. wasn't like word of mouth, show up an event and talk to them, but um you know being able to talk to people
25:20 uh online and market to them, advertise to them there. And so um that was really the tipping point. It was I think
25:27 grounded in that initial foundation. I still remember when TI Adventures, who was that that first fund uh that that
25:33 led that first round, they interviewed landlords on our platform. We gave them about 20 landlords to talk to, just
25:38 randomly selected, and they interviewed them and asked them questions like things like hypothetically if they took
25:44 rentway, how would you feel about that? People were swearing at us like don't take this away from me. They're like,
25:49 we're not taking it away. Just like it helps us understand hypothetically like does this actually help you or not? And
25:56 they were like, it's some of the best like diligence we had ever done. Like people were like swearing at us like
26:01 they love you guys. So really the question at that point in their mind was like, can you make people just as happy
26:06 at a,000 or 10,000 or 100,000 or a million uh landlords and tenants on the platform as you can at 100 or 150? Right
26:13 now it's they're they love you guys, but they're getting to talk to you. And so um that was really the tipping point from a marketing standpoint where we
26:20 started really doing more uh like outbound marketing and advertising and and I think one of the biggest
26:25 challenges was uh just ensuring that as you scale you keep that same quality
26:31 that you had at um you know one I think it's like just like a restaurant you know like if you get like great home
26:37 cooking from your mom or your grandma or somebody um like nothing beats that like
26:42 grandmother home cooking where she just like made the meal for you and only you. But you get to like, you know, a
26:48 restaurant level and you're like, "Okay, I got to do this for like 20 or 50 people in this room." And then you get to like the McDonald's scale. I'm doing
26:54 this for like millions of people across the world. It's like, can you keep the quality um that you once had when you
27:00 were um you know that and I think that's the that's the big focus in my mind is like keep that quality so so it feels
27:07 like you're just talking to one of the the original founders of the company. It's it's extremely hard to do too. One of my
27:12 favorite business movies of all time is Founders. It's Ray Croc, McDonald's. And like the big issue they had with
27:19 franchising was quality control. They they couldn't do it. It took them forever to figure it out. Yeah.
27:24 Extremely hard to do. Going from a mom and pop, which is I mean, it's kind of where it started, right? You're like,
27:30 "Yeah, yeah, it's I have word of mouth clients and we're when you expand that to we're now a big company, but we still
27:37 have that same consistent feel from where we started. It feels it still feels like you are in customer service
27:44 with the founder of the company which apparently occasionally that's actually still true which is crazy
27:49 every now and then. Yeah. Ryan is in fact not AI is actually here. Uh but like when you're putting that
27:56 together how how did you solve the problem of quality control at scale
28:02 because typically 150 clients and you know like 150,000 clients usually the company looks nothing uh like it did at
28:09 150. How do you keep that feel at scale? Yeah. Um, I do think part of it starts
28:14 with what you were actually referencing earlier about like you just have to do it yourself. Think if you if you don't
28:20 do it yourself at first, there's no way you're going to be able to hire other people that are going to do it or
28:27 iterate with them about improving it as you go. Like think ideally things actually get better. not just like uh
28:33 keeping status quo on the quality, but like you actually figure out a better way to do it because you've hired really
28:38 smart people and they start questioning why are you doing things that way? And you're like because it was just me in a basement and no one had was around to
28:45 question why I did things that way. But now that you say that, that makes sense that we should do it this way. This would be even better. And so, um I think
28:52 it starts with doing it yourself. I think the next step is when you do bring people on, bringing on people that
28:57 actually care. I think there's no substitute for people that care about the problem they're solving. And I don't
29:03 mean this just even hypothetically, but there are people on our team, a lot of people on our team that actually own
29:10 rentals themselves, manage their own rentals on Rent Ready, have bought their first properties on Rent Ready, and used
29:16 our own blog to look up things like how do I what's my move in checklist or how
29:21 do I find a tenant or things like legitimately using the platform itself to make themselves successful. There are
29:27 people on our platform that have had parents that like sold their portfolio to put them through college. Like all of
29:32 these things that I talk about aren't just um like, oh, this could be somebody theoretically, but they're actually the
29:38 people within our company that are living that themselves. And I think uh and tenants on the platform. There are
29:44 people on our platform that have been actual tenants of Rent Ready as well. And so it's it's cool in terms of the
29:50 influence that that has when you go from saying, "Okay, I'm doing it myself to now I have a team, but a team that
29:55 really really cares about what they're doing here." And then they proactively ask questions about how things are being
30:01 done and how those things can be better. And they're almost another layer to that that landlord or that tenant that's
30:07 saying the same thing of like, "Here's this problem I have or here's this question I have and how could this be better?" But they're doing it almost
30:13 proactively themselves. And I think that's how you keep and actually even improve that quality at scale because now you have more brains trying to
30:20 figure out uh these different problems and the pros and cons of these different approaches and how you ultimately get
30:26 the best result. If this episode was a test on like how
30:32 to create a business, right? You would be getting an A++ like everything everything is super positive, right?
30:37 It's it's like hey we start organically start with the end in mind with the product. Uh I mean this is all the right
30:43 things to do along the path of creating a large successful company. Uh we all make mistakes and so the question that I
30:50 ask in every episode that everyone's waiting for uh the highest stupid tax that you paid when you start you don't know what you don't know. Um what did
30:57 you not know when you started that you uh that you had to pay to learn? Yeah, we uh I think one of the the biggest
31:04 ones that stuck with me and it's it's it's an important one to continue to remember because it's not sometimes I
31:10 actually forget that I think of it as like only when I'm beginning, but I think this is true at any point in a business is you talked earlier about how
31:18 you don't need like a finished product before you can start doing something. Um even though I did that pitch competition
31:23 and it had some legs, I didn't turn around and go, okay, how do I like plan and then show the concept of this? I
31:30 actually spent the time building the whole thing for like two years and trying to perfect this thing and not
31:35 really getting it in the hands of people. And so in retrospect uh I would
31:40 have built less and released earlier and given it to people and used that as um a way to
31:47 iterate faster. And that is a a big way that we approach the platform even today
31:52 where um if you ask for something that Rent Ready doesn't do today. We legitimately record not like how some
31:59 companies like oh pass it on to the product team. We legitimately record every single feature request that somebody has whether they know it or not
32:06 and we put it in our list of things and it gets voted on and it impacts what we build and why we build it and how we
32:12 build it. we actually review exactly your words of how you wanted this thing to work so that when you look at like a
32:17 hundred people that asked for that thing it it it changes how you approach that and so um that that basically drives how
32:25 we build everything to this day. That is such a great lesson. That was the the only thing and I I I think legitimately
32:31 the only thing when I started any of the businesses that I've done only thing that I think we did right is I I from
32:38 the beginning I had no money to develop any of my products. And so we always sell multiple units in concept and I'm
32:43 like okay I'm going to take the money that we just brought in for the product and then I'm going to make sure that the product matches what we just sold. I've
32:50 done like six or seven things. I'm like start with clients. It's always easier when you start with revenue. The fact
32:56 that you did it for two years without doing that is actually incredible. I mean, it's so
33:02 hard to be like, I'm gonna focus on this problem for two years and it's probably going to work, but what if it doesn't?
33:08 I I think for most people, the the what if this doesn't work and I'm spending two years for nothing?
33:14 I know. That's why I think the biggest lesson is actually amazing. Just start. Just start. you know, like
33:19 whatever it is that you're like planning this, you know, I I'm trying to put together this perfect plan for, just
33:25 like just start the thing. And you'll learn so much by doing even a little bit
33:30 of it and putting it out into the world than you will by like planning behind closed doors, trying to get the perfect
33:36 plan for whatever you're trying to do. And whatever you learn in that time, you'll do it faster the second time you
33:41 do it. Even if it doesn't work, you you already know a ton of stuff that doesn't work. Now, I just had uh I
33:47 actually just had an investor in one of my last deals. Fantastic guy. He built a medical practice over seven years. He
33:53 got it to like he got it pretty big. It was multi-state. It was quite a few employees. I want to say it was 30 40
34:00 employees. Sold it successfully. Had a big exit. He then several years later built the same company but in less than
34:07 half the time. Uh went to four states, 150 people, sold it for like seven times
34:14 as much. he did more than twice as much business in less than half the time because you just you learn along the
34:19 way. You do it better the second time. Even when you pay the the stupid tax for being new, you're gonna learn. You've
34:25 now paid it. So So you got the education. So it's it's an amazing thing. It's I I love that. I love that
34:32 mindset, too. It's it's just get out there and do it. It it doesn't matter if you do it right. I've always just worded
34:37 this done is better or done is better than perfect. Like right produce something. Get it out there.
34:43 True. and you're doing the best iteration of it. You collect actively collect and organize feedback. So you
34:49 can go through uh there's a concept in Ray Dalio's uh book principles which is one of my
34:54 favorite books on business of all time. Uh it is a long book. It's roughly the size of the Bible if you guys are looking for a business book. It's a
35:00 thick one. Uh but he runs his companies as what or his company as what's called an idea meritocracy. And it sounds very
35:07 much like that of like, hey, we collect all of these ideas and everyone has a voice down to the lowest client to the
35:14 highest person and then you have a democratic way to decide and vote on
35:20 what features do we work on and what do we think is the direction of the it seems very in line with that which
35:26 yes it is. It is it is a and the beauty of it is you end up making better decisions. you really end
35:32 up making better. There's a there's a great book called The Wisdom of the Crowd and it talks all about this of how like crowds make better decisions than
35:38 individuals. And it's it's funny that like you get into business and so often like you'll have a company where it's
35:44 like a property management software founded by a property manager that built it for themselves and then says that's
35:49 how everybody should manage. And like there's a different approach where you could say instead what if like hundreds
35:55 of thousands of landlords all voted on what the right way to do it was and then built a platform around what they all
36:02 say is the right way. And according to the wisdom of the crowd, you're going to get a better output. Not because you
36:08 were like a smarter individual, but because you put all of these brains together and said like together we have
36:13 to be able to figure out a better way than we would ever do individually on our own. And I think it's a it's really
36:19 fun to then see that like organism come to life. Well, typically I would wrap with like,
36:25 hey, where does someone find you? But I mean, rent ready, you've done a fantastic job building. It's not that hard to find. Uh, you did re n t re d i.
36:32 Um, so it's not that hard to find. Uh, that being said, if someone was a landlord and they're looking for the
36:38 solution for self-management and small, medium, large landlord, uh, what is the
36:43 best way to get connected with Rent Ready? Yeah, we're we're a friendly bunch. Um we have we have live chat and um uh
36:50 demos and everything available on the on the site anytime. So like you said rei
36:55 um we spell it wrong because we're a startup but um you can you can Yeah, exactly. You can you can do it
37:02 yourself and and not talk to us at all. And that's intentionally designed where if you're like sometimes I'm that way
37:07 I'm like you know what I just want to set this thing up at night and not be bothered. That's fine. But also like the live chat's there. It's been part of our
37:14 core DNA since day one. not just for you, but for your tenants. Like they can message us, too. Every single tenant on the platform. Um and so, you know, you
37:22 can reach out anytime if you have questions or just want somebody to chat to, we're always there. It's uh it's always nice to talk to people and um
37:28 whether you realize it or not, you're you're influencing the future of real estate at that point. That is absolutely amazing. Well, guys,
37:35 uh link is also below in the show notes. You guys can always check out Rent Ready there. Ryan, awesome, awesome, awesome
37:41 having you on. Huge privilege. Everyone, uh, if you enjoyed this episode, we interview owners of businesses and real
37:49 estate, uh, doing the thing that you want to do. So, if you want to get all the takeaways of the people who have
37:55 already succeeded in the projects you want to do and already failed in things that you don't need to fail at, we'll see you on the next episode.

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