Veteran Joseph Riley On Raising $400 Million To Offer Short-Term Rentals In Underserved Areas

Joseph Riley has become a master of turning challenges into profitable opportunities. Including building a big real estate startup that has raised hundreds of millions of dollars. The venture, Patriot Family Homes, acquired funding from top-tier investors like TRT Holdings and Miramar Holdings.

In this episode, you will learn:

• Branding and developing multiple brands
• Customer experience
• Debt versus equity funding
• Unique investor introductions
• Joseph Riley’s top advice when starting a business

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About Joseph Riley:

Joe Riley founded Patriot Family Homes in 2018 to meet the need for affordable, reliable housing in the South, particularly near military bases.

Until 2021, Joe was an Infantry officer in the Army. He deployed to Afghanistan and Ukraine and served as a Director on the National Security Council at the White House.

After leaving the Army in late 2021, Joe rapidly grew Patriot Family Homes from 100 houses to 400 as of January 2023. An East TN native, Joe and his wife Rachel moved home to Chattanooga with their two boys, Jacob and Jonah.

They live on a working farm just outside of Chattanooga, which doubles as the Patriot HQ. Joe earned a BA from the University of Virginia and a master’s and doctorate in International Relations from Oxford University as a Rhodes Scholar.

Connect with Joseph Riley:

• LinkedIn
• TheOrg
• RocketReach

Read the Full Transcription of the Interview:

Alejandro Cremades: All righty hello everyone and welcome to the deal maker show. So today. We’re gonna be interviewing quite an inspiring entrepreneur an entrepreneur entrepreneur that they not only has been serving our country the United States but then also you know he’s being building this incredible company that. I think you’re all going to love you know building scaling financing going through the ups and downs. You know how they went through covid and what they did you know to to really not only survive but to thrive. But again you know you’re all going to love this so without farther ado let’s welcome our guest Today. Joseph Riley welcome to the show.

Joseph Riley: Thank you very much. It’s an honor to be here I Really appreciate you having me on.

Alejandro Cremades: So originally from Tennessee your Soro file I walked through memory lame how was life growing up.

Joseph Riley: Yeah I grew up on a farm in a little small town in East Tennessee didn’t want to go to college I only wound up going to college because ah I was the first business class I ever took was keyboarding you know because I grew up in a town that you know we didn’t have any wi-fi sounds almost foreign. Ah, but so my business class was typing and I was failing my typing class and so my keyboarding so teacher said you know you’re no good at typing. But if you enter this public speaking competition you like to talk a lot I’ll give you an a on this test you failed so I did that and one and she said if you go to regionals I give you an a. Um, the next test and that sounded pretty easy. So I did that said you go to state I give you an a on the next one for the semester. So I did that said you go to nationals I give you an a for any class you ever take from me so I did that and when I was there I said you know I want to be national president of future business leaders of America and she said you know we’ve never even had a. Ah, regional or district officer said it’s thought it’s all right? So I you know started running for office wound up getting elected national president or future business leaders of America and some other groups and from that got a scholarship to the University Of Virginia did army ah rtc wanted to serve our country. Ah. Then right out undergrad went over to Oxford did a master’s in doctorate international relations focused on us China competition came back to the army was in the infantry had done some different rotations and and so forth in different places and ultimately was on a deployment to Afghanistan.

Joseph Riley: Ah, my wife is a partner at Mckinsey and so travels for work. So we.

Alejandro Cremades: And and 1 second one second there Joe because say I’m sure the people are listening. We love to hear how did the um, the calling for for joining the army come about. You know, is there anyone in your family or growing up. You know some type of experience that really inspired you to want to um to serve the country or how that they come about.

Joseph Riley: Her so in like in most small towns. Everything revolves around sports and you know every little small town sports has their like you know patron saints so to speak. Ah and ours was a gentleman named Watty Smith ah who had served in the green brace and in Vietnam and I was always inspired by his commitment to service ah of continuing to support our local school but then also kind of what I saw in him from his time from when he’d been in the military and so. Ah, that’s that’s a large reason why I wanted to go in the military.

Alejandro Cremades: And I mean you’ve you’ve been there you you were in the military for for serving the country for about 7 years You reach the captain rank. So I’m sure that there’s a lot of experiences there you know Afghanistan as you were saying you were deployed to ukraine as well. Ah, you’ve dealt and and obviously we’re not going to get into it because of some of this you know maybe classified and and and also you know perhaps you know experiences there that that that that you’re not so inclined to touch on but I guess what kind of. What kind of lessons did you really get from that experience because to a certain degree I find that building a company from the ground up is also going into battle. It’s also being in battlefield. It’s putting fires away. It’s putting threats away. Is leadership is say so what? What did you get from from the from the army experience that you know perhaps you could apply to business.

Joseph Riley: Yeah, so I’ll also frame this in the advice I give veterans who are leaving the service. So First of all, most people who want to leave the military they say oh I can’t wait to go work for a startup because you know I’ve spent my time in the military you know, building systems and doing all this and I say that’s nonsense right. You didn’t build any systems in the military. The military is the most bureaucratized organization that there is that it’s got 200 years of people building systems and process for you. So you know most the challenge for most military folks who want to go into entrepreneurship is that they’re used to operating within a very structured. And kind of rules-based environment right? where you know there’s a rank structure. There’s an order There’s you know down to the way orders process are produced. It’s all the same and then the second thing is they’ve never had internalized labor costs right? So when military folks you know, see a problem. Their inclination is to think I need people instead of I need a better process. But on the flip side to your point. What is so important as an entrepreneur is being willing to face down a really difficult circumstance and just say you know failure is not an option I can’t quit and that is what in my experience military folks do a really good job of because when you’re. Ah, you know when you’re on the Afghanistan border with another country and you’re taking ah, you’re taking a lot of fire. There’s a lot of cloud cover and there’s more folks on the other side than you anticipated when you showed up and you can’t get metava out and you can’t get the you know gunships in that you were anticipating.

Joseph Riley: You know you you got to figure out something to make it work because no one’s coming to help you and that’s kind of what it’s like being an entrepreneur.

Alejandro Cremades: And and you know this reminds me a little bit to the book extreme ownership from ah Jocko willingk you know is a fantastic book where you know he put some stories there too and how you you could apply them also to on entrepreneurship I guess. You know leadership is also a key one and you guys have been growing the team and we’ll talk about what you guys are up doing just a little bit but leadership is a really big one. So can you give us you know perhaps a crazy adrenaline Phil story that you know you are comfortable sharing where leadership was present and where. You got super inspired by.

Joseph Riley: Um, from the from the military days right? Um, oh my goodness. It’s almost like there’s a paralysis of so many different options to choose from. Um, you know I’ve just seen.

Alejandro Cremades: That’s right.

Joseph Riley: You know some phenomenal acts of heroism and bravery. Um, but I think that I think that probably the one that I would look to the most is um.

Joseph Riley: Um, let me I’m I’m gonna tell different 1 okay because I don’t I don’t want to get I don’t want get emotional on the show. So um, my when when I came out of ah well, we’ll do a noncombat one when when I came out of ah the army the army actually tried to kick me out. Because I was on this completely different track I’d gone to Oxford I hadn’t done the normal things that folks were would would have expected and so they told me the only person that can save your career is the chief of staff of the army and I was going to be on a panel with the chief of staff of the army in a few weeks to do this thing and so got on there long story short. I was kind of back on track and then my command and then he sent me to go with his aide-de-camp so his kind of guy who’d been his right hand person for a while and normally again I was completely so completely off track I should not have you know my career should have been in the dumps and this officer. You know is probably the most inspiring leader that I’ve ever worked for. He took me in he said you know what I’m going to do not only am I going to bring you in the battalion and I’m going to like let you you go through a couple of these I’m going to give you the most problematic platoon. Because I’m going to give you the opportunity to show folks that even though you haven’t had all of these experiences that the army says you were supposed to have that you can still perform as a leader and so I got to take that platoon that had more people that were on drugs and getting chaptered out of the army and lowest physical fitness score lowest you know ah you know marksmanship scores

Joseph Riley: And bring them up to the top platoon in the battalion and then based off that he was willing to send me to ranger school I went to ranger school ah you know and then was able to get through ranger school deploy with the rangers to Afghanistan and really kind of set my career back on track. So I could have ah kind of. Probably given some other examples but for for a range of making sure we’re we’re saying optimistic and upbeat and not disclosing anything. We shouldn’t we’ll we’ll stay focused on ah you know the ah you know someone taking a chance on me. Ah, when it would have been very easy to just kind of cast me aside gave me that opportunity and that’s made all the difference for me in my career.

Alejandro Cremades: And it’s a also it reminds me of a you know luck luck at the end of the day is I find that people oh you got lucky and and and yes you know we all get lucky right? and especially the ones that end up breaching the finish line. You know they do get lucky but luck at the end of the day is.

Joseph Riley: Yes.

Alejandro Cremades: Preparation meets opportunity which is what you know you are alluding to you got to generate that so I guess in your case, you know you went to study at Oxford you know, obviously you went through these deployments but 1 thing that happened that that was very interesting is when you came back to the us you started to experience.

Joseph Riley: Um, but.

Alejandro Cremades: Ah, what real estate you know was you know, perhaps you know like you started dipping. You know your feed and in in real estate you know, perhaps you know, buying renting. So how did that all you know come about and how and how does it develop into patriot. Family homes the business that you’re running today.

Joseph Riley: Yeah, so when I was in Afghanistan my wife travels for work so we needed to figure out something to do with our house and so we just you know it was kind of a last minute deployment as ah, folks who are you know ah have been in the military can appreciate and so. We just literally had time we’t have time to bring in a tenant. We just finished renovating the house. We said let’s see the furniture in it. We’ll just list it on Airbnb and homeway maybe some people will need it and realized no surprise. There is a huge need for furnished short-term accommodations around military bases. People moving from one base to another you know like my wife and I moved 8 times in 8 years in the military um people coming in to watch their soldiers graduate from airborne school or ranger school or basic training I wanted to be there together as a family. So. Took off so then we came back I moved my wife and I I didn’t want to give up on the revenue as many entrepreneurs this story will resonate so I moved my wife and I in the 1 bedroom of our 3 bedroomroom house started renting the other two bedrooms I also bred our dog without telling her because I thought the dog was in the negative you know, read on the balance sheet. Ah and but then we started. Buying warhouses flipping them turning those into short term rentals and you know then moved from Fort Benning which is there in Columbus georgia to other military bases covid hit first time I thought I was going to go bankrupt because how am I you know how do we manage? you know this, we lost 90% of our reservations in the first week

Joseph Riley: Ah, because the secretary defense put in a stop movement order but wound up.

Alejandro Cremades: And and and and let me let me stop you right there because obviously you know Covid is ah is a big time on certain event. Ah now you had an advantage you know because you were you know serving the country for for so long you know in this this different deployments where.

Joseph Riley: Um, event.

Alejandro Cremades: You had a different exposure to uncertainty and to uncertain events and I’m sure that served you well when dealing with you know, events like this you know which is obviously not life threatening and there is more you know towards business. But how do you think that being able to be with uncertainty. During your years in the Army gave you an advantage to be able to tackle a situation like covid.

Joseph Riley: So you know we huddled our entire team at the time which was a very small ah very small group of ah veterans and military spouses who are all working with us and just what you said you know this is one of those times failure was not an option. You know this was not. Ah, Vc company at the time where we were kind of playing with other people’s money. This was all my money at the time and I was personally guaranteeing millions of dollars worth of loans and I didn’t know how I was going to make the payments right? because our you know revenue stream had just dried up so we all pulled together we we we. Heavily focused around in Columbus Georgia was just outside of Atlanta we started a walking dead. You know, get out of Atlanta while you still can ad campaign. We started calling insurance companies who needed to displace. You know? Ah, ah, put people in houses health care companies. So we started getting created with what. Whatever were the all the different possible contractors. You know who were in you know, kind of critical industries you know and putting them up because they needed a place to stay when they were on the road doing jobs and that then wound up being a huge opportunity for growth right? because before we just focused on the military traffic. But when we were. Forcibly deprived of that revenue stream then we picked up all of these other revenue streams that actually allowed us to grow the company far more you know expand the company into other markets that we’re not military markets start serving other guests and ultimately you know dramatically increase the pace of growth.

Joseph Riley: And that would never have happened if not for covid um, and it’s like it’s the second time in my career where you know something ah completely unexpected that looked like it was going to ruin us wound up being. You know the kind of you know, forcing function. Ah that you know pushed us to create a new process or open up a new customer base. And again that kind of goes back to the military of you know? Ah when when rounds are inbound. Ah no, one’s you know there’s no sitting and you know you know wallowing in self pity in the corner you got to do something.

Alejandro Cremades: Now in this case, you know it sounds like you guys. You know, really turned you know around the corner there and you came up you you came out of that you know even more powerful than you know the way that you entered it now for you I mean you were alluding to it. You were really bootstrapping this entire thing. Ah, and you know it was quite a sizeable operation at that point now you even touched on it. You know on the fact that you have spouses um of of people that are serving Now. How did that idea come about of a hey you know like maybe you know like we could really. Ramp up the the talent by also you know for a bigger purpose here and and allowing you know this this this spouses to to come in and and make it happen with us. So.

Joseph Riley: So when I ah got my ah first took out my first decent size loan to go buy a portfolio of homes literally the day after I closed the army said surprise we need somebody to go fill a unit in Ukraine. Ah, to go train some of their forces over in Ukraine and so I thought again well this is how I go bankrupt because you know how do I manage this operationally intensive short term rental portfolio from shipping ah from a shipping container in rural Ukraine. And 1 of the guys I was deploying with his ah wife had been a west point grad army officer and then had gotten out and was doing real estate and he was like look let’s see let’s ah, have Kate you know, take over the portfolio and so then Kate came in and opened up this whole. Amazing talent pool of military spouses who’ve completely kind of transformed and it’s this you know highly overqualified underemployed you know talent base because they have to move all the time and so we have military spouses you know working for us in Dubai. Ah, where their husbands deployed and all and you know literally across the country. It’s a kind of a nightmare from the ah hr standpoint because we have to file in all of these different states. Ah but it was. It’s ah just a tremendous blessing and military spouses are exactly the sort of savvy you know scrappy.

Joseph Riley: Ah, you know folks that you want in ah in in a startup and so that was a great opportunity and now Kate who is that you know, kind of first employee has grown and done basically every role in the company is now our chief growth ah chief chief growth officer. So.

Alejandro Cremades: That’s amazing. That’s amazing now for ah for also for the people that are listening. You know that are interested in the whole fundraising and and transactional piece here I mean you were you were talking order that you bootstrapped the operation for the for the early years um for the early phases right now. How much capital have you guys raised today between equity and debt.

Joseph Riley: Ah, all blended probably around 400,000,000

Alejandro Cremades: And what is the how would you say you know why? deb you know, comes in the equation here. How do you guys? you know work debt into the business and how does that balance you know with the equity side.

Joseph Riley: Yeah, so we have 2 different we have ah the operating company right? Which is what employs everybody and does all of the activity for those of you in you know, familiar with the real estate space. Often you’ll have this opco propco structure and then the propco owns the actual real estate because it is on on one side very capital intensive to buy the real estate but because it’s seen as a more secure asset. It’s very bankable particularly in the single family rental context where we operate. So. You know we raise mainly equity into the operating company and then in the propco we raise a blend of equity and debt and in fact, more obviously more debt than than equity usually about twice or so you know 2 to 3 times as much debt as equity depending on the deal and and so forth. And so you know we’ve done everything on the debt side from small and when we first started out I literally was driving around in my truck ah to local community banks trying to find somebody to bankroll this. You know, kind of crazy idea from a military guy who is like. You know I can manage these you know short terminal properties all over the country and you know I need you to give me loans. Ah and then you know we would kind of flip them pull equity out of them. You know, repeat and then all the way up now I can’t disclose who the partners are but we’re the first player in our space to get kind of 9 figure. Um.

Joseph Riley: You know style debt facilities. Ah from you know national? You know, household name lenders and then in between that we worked with some specialty lenders and regional banks. So that’s that’s on the kind of debt side on the equity side. You know we really for the first you know. Two or three years tried to be so very focused on kind of raising you know, just just you know, growing off a cash flow and debt. But then in 2021 we raised you know around kind of 10000000 or so blended across opco and propco and then in 2022 we raised another kind of. You know, $60000000 you know, blended across opco and propco. So that’s a little bit of kind of what the equity looks like and typically when we partner with an equity partner on the opco what we’ll do is. We’ll get a commitment that’s about 5 to one of a propco versus opco you know because you need ah equity in the in the propco as well, right? So we’ll say. You know you give us $50000000 in prop cofunding and we’ll let you invest $10000000 in the operating company.

Alejandro Cremades: And ultimately as a whole for the people that are listening to get it How how are you guys making money.

Joseph Riley: In terms of what what’s the source of our revenue or yeah, so um, we are fully vertically integrated So our core business is obviously the rental income off of the property. So when someone comes and stays at our homes.

Alejandro Cremades: That’s great to what’s the source of the revenue for the company.

Joseph Riley: You know they pay us. You know whether it’s an insurance company somebody traveling for vacation. Whatever it might be a large different use case there but that rental in comes the core. But unlike most companies in our space who have never made money and have always just had to you know, raise more and more and more capital because they were burning so fast. And the reason is because their business models were predicated on essentially buying mom and pops or doing very expensive direct-to consumer marketing whereas what we said is we want to build an operational machine that is one vertically integrated. So we have an acquisitions department a renovation oversight department. We procure our own ff and e we then sell the ff and e to the propcos. We do the full service property management guest services engagement league. You know the whole nine yards so we are kind of soup to nuts. You know? ah. You know capital allocator for you know, institutional style investors and then the second thing is we want to focus on delivering you know great returns for those propcos because by delivering great returns for those proppcos we’re able to track more and more capital. And then we get paid an acquisition fee which is ah you know we have a marginal net business. We get paid a renovation oversight fee so we make money there we you know candidly Mark up the ff and e that we sell and we charge a shipping and delivery and install fees. So unlike all of our other competitors.

Joseph Riley: That are paying sometimes Eight nine 10 15 times ebita to be able to acquire more contracts. We actually make money at every stage of growth and are very profitable in growth because we’ve looked at the growth machine is not a cost center but a profit center and we’ve tried to organize it in the kind of fee for service. Ah, structure in order to achieve that so we make money in the growth phase and we make money on the kind of stable state.

Alejandro Cremades: And talking about the capital you know again to expand on that I just wanted to really quickly. You know, get the listeners to understand how you guys are making money but expanding and and double clicking on the capital side of things you know as they say while ghost around comes around tell us about that car wreck. That happened and how you know that led to you being introduced to one of your capital partners.

Joseph Riley: Yeah, so we I may have one of the most kind of crazy wild stories for getting linked up with a capital partner. But when I was in Oxford I used to my wife and I would like to you know. Another way to make money or you know they were not even necessari make money but just to have fun is we would go rent these castles and then we would have other people you know, go on these trips that we would plan and so we’d rented. Ah, ah, ah, a castle in France and and taken a bunch of friends over there from Oxford and as we were coming back. To the castle one evening there’s a kind of caravan of cars in the car in front of us pulled out and got t-boed by a ah by bus have rolled it multiple times and one of ah the girls in the car wasn’t wearing a seatbelt everybody in the car was injured. You know somewhat she was injured pretty badly. Um you know. A lot of people froze. But I you know I guess from growing up on a farm and the military background everything else. So I jumped in started pulling people out of the car got her out of the car right before ah it got really bad. Um and was able to get her. You know to a hospital and. Um, and so I think she overexaggerates it she you know the way she would tell the story is Joe pulled me out of a burning car and saved my life but she then went on was extremely successful. Did a bunch of different things. We worked at the white house together and after she left the white house. She took a job.

Joseph Riley: Ah, in in in Dallas with one of the family offices that ultimately provided our capital and so you know she one of their deal. Ah you know, kind of generators was asking about different opportunities and she was like oh you should talk to my friend Joe and told that story and so um. You know she’s a very special special friend and very grateful to her for for helping us get the opportunity. It’s an interesting story that at the at the closing dinner that we love to kind of tell about how we got linked up.

Alejandro Cremades: I Mean no kidding I mean they people always talk about the importance of having warm introductions to investors. But my God getting an introduction like that when someone is telling you hey I got introduced you to this guy that saved my life pull me you know in out of a car in flames and. I mean I will give you money too. You know come on I mean that’s unbelievable now Now, let’s let’s let’s let’s switch gears here. Let’s let’s go back to you know now I want to talk about the company the division because obviously division is something that you that you had to share with investors too. So imagine you were to go to sleep tonight. And you wake up in a world where the vision is fully realized for the company. What does that world look like.

Joseph Riley: So the first thing I want to say is you know you know entrepreneurs are talking to each other when they start a sentence is like imagine you go to sleep tonight like imagine you actually get your work done and can go to sleep tonight. That’s that’s perhaps the the interesting vote. But if I do which I hope I do.

Alejandro Cremades: Ah, ah.

Joseph Riley: Tonight Um, you know what? we would love to see ah I’ll frame it in in in a couple senses one from a customer facing view. Our view is that the short terminal industry offers a phenomenal product to guests who won’t. Larger homes to be able to gather as a family longer term stay have a kitchen all of these things but it’s very fragmented and in our view kind of unprofessionalized across the space. So What we would like to do is help bring the sort of discipline And. Ah, you know, kind of quality expectations that you would experience from Hotel Brands ah to the short term rental space so people are getting the benefits of the being in a single- Familymi home with some of the confidence of quality that they would have in a hotel similar to that you there are a lot of different use cases for why people need to stay in short-term Rentals. So Our new President Coo We hired one of you know he ran all of it. She’s kind of brand and loyalty programs and ran um a lot of their times sharere and stuff and so what he’s thinking helping us think about is how do we create a multibra short term rental. You know you know Enterprise. So that you know you can have a brand that targets luxury stays and you can have a brand that targets economy stays or longterm stays or you know unique stays and likelamping and you know and treehouses and um so how do you create? you know one? you know.

Joseph Riley: Harness The efficiencies of kind of scale on the backend operations from accounting and cleaning and operations and all of that stuff but then present a multi-branded product to customers so they know what they get what they’re getting when they book right? Do they they know are they you know. Am I traveling for for work with my colleagues in which case I maybe just want more of an economy style product or am I like taking this big vacation with my family that I’ve planned on for a long time where I want to make sure I’ve got a higher quality product and so that’s that’s that’s one piece of it on the kind of customer facing sign. And then on the inside View. What is really important for us is to continue to build a strong and scrappy culture that allows us to kind of you know, bring in folks who we say you know are grateful for for the opportunity to be a part of our team and we’re grateful to have them and so we hire a lot of military spouses as we talked about. Hire A lot of Veterans Increasingly we hire a lot of folks who are leaving prison or you know coming out of incarceration because we find they’re great folks to work in our warehouses or do maintenance tax and so you know putting together that team of kind of you know ah of kind of almost scrappy misfits but putting them in in a great organizational culture. Is something that we’re really you know, excited about and then of course ultimately you know we’d love to be the largest you know, vertically integrated short-term ah short-term rental operator. You know in the country and then ultimately in the world.

Alejandro Cremades: I love that now. Imagine we go back to the past. So we’ve been talking about the future now we go now we go to the past but we do it with a length of reflection. Let’s say I put you to a time machine and I bring you back in time to that moment where. You know you you were thinking about doing something of your own and let’s say you had the opportunity of giving that younger Joe one piece of advice for launching a business. What would that be and why given what you know now.

Joseph Riley: Invest in counting resources sooner that may sound super practical and maybe not entirely inspiring but you know 1 thing that delayed our fundraising as long as it did was because in the course of bootstrapping. And it was you know in my view kind of you know my company my you know I wasn’t as worried about investing in accounting resources and if it was you know in this bucket or that account or were it not that big a deal. But then when we started going out and trying to recruit institutional style capital. You know. It was difficult for us to get them comfortable with you know with our accounting and we had to invest and we had to then spend a lot more on the backside to get ourselves cleaned up so that’s not super inspiring but I would have said you know my cheap skate tendencies were probably right in most respects but I maybe should have been a little less cheap on accounting.

Alejandro Cremades: I love that so Joe for the people that are listening that will love to reach out and say hi. What is the best way for them to do so.

Joseph Riley: They can just go to PatriotFamilymilyhomesDotCom so’s patriotfamilyhomes.com you’re also welcome to shoot me an email at my personal email which is just Joe Joey at patriotfamilyhomemes.com

Alejandro Cremades: Amazing, easy enough. Well Joe thank you so much for being on the deal maker show. It has been an honor to have you with us today.

Joseph Riley: Thank you so much.

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