The Ultimate Guide to Midterm Rentals: Expert Insights and Strategies

Dylan Silver (00:00.837)
Hey folks, welcome back to the show. I’m your host Dylan Silver and today on the show we have Justin Cambra out of Seattle, Washington. Justin went from W2 to Freedom in six years, real estate investor, agent that helps people build wealth through real estate and loves to travel. Justin, welcome to the show.

Justin Cambra (00:21.696)
thanks for having me. I’m super excited to talk to you and share any of my experience for your audience here.

Dylan Silver (00:28.227)
What’s the temperature like up there in Seattle? I love Seattle, and Seattle sometimes has a reputation as a rainy city, but I went up there and I loved the rain. I remember, I think it’s they are throwing fish in Seattle, if I’m remembering the city correctly.

Justin Cambra (00:40.046)
Exactly. Yeah, actually the weather is perfect today because we’re probably about 60s and sunny which is You know pretty rare in this time of year. So we’re just getting into spring right before summer. So it’s perfect But I actually heard they don’t throw the fish anymore. I think they switched to a stuffed animal for I don’t know if you want to say peter reasons, but protecting the the wildlife if you will

Dylan Silver (00:55.92)
What?

Dylan Silver (01:08.715)
no. no. well, believe it. Correct me if I’m wrong, Seattle is one of the original places of Starbucks, is that right?

Justin Cambra (01:09.996)
Yeah.

Justin Cambra (01:19.244)
Yeah, 100%.

Dylan Silver (01:21.659)
How did you end up in the Seattle area? Are you Seattle native?

Justin Cambra (01:24.91)
Yeah, Seattle native. grew up about an hour south of here and then went to college and everything locally. And then, you know, first couple of jobs out of college was out of state and then ultimately gravitated back to Seattle area. 2013 is when I came back into Seattle and then got into investing in 2016.

Dylan Silver (01:47.631)
Okay, getting into investing and lots of folks have different paths. For me, it was I was selling cars, looking on the outside, looking in, knew I wasn’t loving the 12 hour days, saw people who were, you know, 10, 15 years my senior and I didn’t love the future ahead of me. So I said, how do I get into real estate? Started networking, it took me a while. I kind of was one of these people, analysis paralysis, if you will. But I went to a conference and that kind of changed things for me.

first couple deals shortly after that. What was your experience like getting into the real estate investment space?

Justin Cambra (02:24.558)
For me, it was very similar. You’re working long hours and you’re like, what am I doing with my life? And so for me, was, you know, I was, when I moved back, I got my MBA at Berkeley and then I moved back. was like, I want to work for a large corporate company out of Seattle, get back to home. Obviously at the time, you know, we were talking about Starbucks and there’s Boeing and there’s Microsoft and Amazon. So I got my job with Amazon and I came back and, you know, I quickly realized.

it’s the golden handcuffs where I was making the most money ever made and I was working a lot of hours and not just you know Monday through Friday you know so nights and the weekends and always on top of your mind and so I was like I’ve got to figure out a way to take this you know large base of the compensation is RSU’s restricted stock units that invest in the future so was like I got to find a way to take this money that’s coming and get a way out.

Dylan Silver (02:55.665)
Mmm.

Justin Cambra (03:22.506)
And so I just kind of was like, you know, searching on the internet and I stumbled upon bigger pockets. And then I was like, man, this is like the average Joe person can become wealthy in real estate. And I’m like, let’s, let’s do this.

Dylan Silver (03:36.697)
Okay, wow. So BiggerPockets, amazing how many people they’ve gotten started. So you’re working for Amazon, you have this idea, I’m working super hard, there’s gotta be more than this, but you’re also entrenched into a career, so much schooling, Interestingly enough, I had a conversation with an attorney out of Arizona who went through everything, law school, was working as an attorney, and just said, I can’t do this, I don’t wanna do this.

was good at his job, right? And so when you’re that far in, I’m almost grateful that I don’t have lots of, you know, degrees and letters in front of my name because I feel like I wouldn’t have the courage and the bravery to be like, hey, I actually, from a wellbeing standpoint, this isn’t for me, I’m gonna go do something else. Was there a lot of like trepidation? I don’t wanna say fear, but a lot of concern about I’m leaving this to go do something else. And how did you manage that?

Justin Cambra (04:34.242)
There definitely is. mean, when you get that monthly paycheck, it’s almost like an addiction, right? You’re so used to that. So, you know, walk away from that. It’s very difficult. And then the other thing is for these people that your audience is equity based or stock based, there’s always money in the future. So no matter when you leave, there’s money left on the table because you’re you’re leaving that. And so for me, I was like, I’ve got to, you know, instead of making that big jump.

the next level and actually it’s probably like this from income to theoretically no income. I was like, how do I shorten that step? And so, that’s when I started getting in real estate and built that all the way up to where okay the step from consistent income to variable income was more of a baby step. And then I was like, it just makes sense. So, I say risk tolerance was increasing over time. My nervousness was decreasing over time and then just made sense.

It’s time to go.

Dylan Silver (05:34.545)
That’s the very well thought out analysis. I’m literally picturing this in my head. Some people just jump. I was speaking to a woman yesterday who did short term rentals and just sound like she just jumped and bought a cabin in the woods. And I said, you know, God bless you. This is phenomenal. I don’t have the guts for that. But I will say these transitions are scary. My own transition, was not. I’m actually grateful. And in a crazy way, I’m grateful that my transition wasn’t.

Justin Cambra (05:47.944)
Yeah.

Dylan Silver (06:04.131)
as stark as I’ve heard with some people because I went from selling cars to then wholesaling real estate. And it wasn’t as drastic as some of these stories, certainly going from being an attorney to full-time real estate investor. That’s it. That seemed like one of the most drastic jumps, especially for being such a young guy. But when you’re going through that process, you’re looking at deals, you’re educating yourself, bigger pockets, and you’re thinking, well, what’s my exit strategy here?

How are you going about getting that first deal? What did that first deal look like? Find it on the MLS. Was it off market? How did you acquire that deal?

Justin Cambra (06:41.944)
Yeah, that first deal is probably still my best deal yet. You know, some of it’s just beginner’s luck. What I ended up doing, like most people, you know, that was the rise of Zillow at the time and obviously in Redfin. I don’t know if Redfin was big back then, but you know, there’s a lot of sites you can go look at properties. And then ended up working with, you know, I had bought and sold primary residence before, but then, you know, I was

in Seattle, living downtown, paying all this rent, and I was like, well, if I can just get a property, and my, know, at the time there wasn’t a house hack. I just called it, you know, I’m a, I like sports and I, you know, I thinking about basketball, the and one, and I was like, okay, make the bucket and then you got the free throw. So I’m like, I want to live somewhere, and the and one would be, you know, some rent coming in, or some, in this scenario, some future development. And so.

through working with the previous agent who helped me buy and sell primary residence, I started looking specifically for something that had an and one. was just duplexes, single family with mother-in-law, just any, or triplexes, anything up to a fourplex. And at that time, I mean, it always seems like it’s super hot, but it was 2016.

And the first couple I was getting out in bed and then I finally found the one I just went all in like 25 % above list and I didn’t go all the way up there but I put the escalation and ended up getting that. I don’t even know if it was like number three or four or something like that but it’s a duplex in Seattle with land to develop in the future.

Dylan Silver (08:21.209)
Okay.

Let’s talk about that strategy there. so escalation. I’m in Texas, I’m a licensed agent in Texas, newly licensed. Escalation, when you say that your offer was at market value, but you instructed your realtor to, if the offer gets outbid, to escalate it to 25%, was this something that was an addendum in writing as part of the contract, or was it a verbal between you and your realtor?

Justin Cambra (08:49.678)
It was through, I’m an agent myself and so here there’s an escalation 35E escalation addendum and so that’s what we used. It was listed at $450, which sounds cheap for Seattle but this was 2016. It was listed at $450, I put an escalation, I said I paid $10,000 more than the next person up to $600,000.

And so that we submitted the offer. was one other offer in there, but ultimately ended up landing on 535.

Dylan Silver (09:21.125)
Wow. So I’m curious selfishly because I only got my license. This is kind of a funny roundabout story because I’m on the phone talking with real estate agents. I’m a wholesaler. I have deals under my belt. I’ve got like 15 to 20 deals that I did in my two years in now. So it was like a year, year and a half in and I’m still getting realtors who are heavy resistance to wanting to work with wholesalers. And I, I get it. I get it.

So I become a realtor because I’m thinking, let me remove that resistance. Let me know the lingo. Let me understand the documents a little bit better. Did you become a realtor for similar reasons or totally different reasons? Were you a realtor already?

Justin Cambra (10:01.058)
No, I didn’t get my license until probably six years in. So we were talking earlier about how did you get comfortable with the transition. you know, the other thing about was income, but it was stratification of income. So by the time I left Amazon, I had the rentals, short, medium and long term. And I had…

I got my real estate license as well. I was doing some fix and flip and I was wholesaling. And so, I kind of had everything to where when I left, it wasn’t like just one thing I was making money on. I had multiple things that were bringing in cash to me.

Dylan Silver (10:42.267)
Let’s talk about some strategies, rental strategies here. We’re going to dive into this. Short term, I heard, did I hear midterm and long term are one of those two?

Justin Cambra (10:51.667)
Yeah, I’m doing all three

Dylan Silver (10:53.635)
Okay, so very interesting strategy and to use all of them, I think, and I’ve spoken with I don’t know how many 40 guests here in the last month, quite a few, and I don’t know any of them that are doing all three strategies. I would say that makes you very unique nationally as far as someone who is dealing with those three different asset classes. Where did you, I guess, determine, hey, I’m gonna do all three?

Was it a natural progression or was it more of divine intervention? Hey, I just had these opportunities. Let me do all three.

Justin Cambra (11:29.708)
literally natural progression. It wasn’t like, hey, I’m gonna get into short-term rentals or medium-term rentals. I think everybody, or most people start with the long-term. So for me, I was in Seattle, and I bought that first place in Seattle, and then I was in finance at Amazon, so I could very quickly analyze deals. Nothing cash flowed.

So then I went to Eastern Washington, bought an 11plex, my next one. But then ultimately I built the portfolio in the Midwest was all long-term rentals specifically for cashflow. And then fast forward a couple of years, and then I was like, man, Seattle prices have like shot way up, man, I’m losing on equity. So when you start getting into these more equity plays versus cashflow play, the only way that you can ideally break even or better with a

equity play is something that generates more income than long-term. So that’s kind of what got me into the medium-term rental and short-term rental.

Dylan Silver (12:29.157)
I want to dive into the medium term rental because we see a lot. Of course, you know, everyone knows about long term rental. Everyone. You’ve been a renter. Right. People have understand that people are becoming more and more and more aware of Airbnb. Airbnb is actually international. Now people if you’ve traveled as you’ve traveled, Justin, you probably see just how international Airbnb is is incredible. But then also there is a midterm or corporate housing.

And people may be unaware of exactly what this is. I had it explained to me this way. If you knew that there was going to be a business person affiliated with a company that was going to need to be staying in this place for X period of time or a nurse for X period of time, that’s pretty much a lock. And you don’t really have to worry about evicting them because they’re there because of the company or the organization. So if there’s an issue, that company is going to have an issue with it too, not just you.

Justin Cambra (13:25.132)
Right. And that’s, you know, I ended up getting into like my first, well, maybe it was my fifth one, but the, short-term rental, so during COVID, I, had, I actually had a short-term rental in my house hack that very first property I was telling you about. My long-term renter who was at Amazon moved to go work at Metta in the Bay area in California. So then I switched to short-term rental, literally like.

right before COVID. And then as soon as COVID happened, was like, all the bookings are gone. So now I went from the below unit was paying my entire mortgage to paying no mortgage. And then I was like, man, there’s got to be an alternative.

That’s how I stumbled on medium to rentals. Obviously, traveling nurses was paramount for the entire, basically, world at that point. So I did pretty much two years of only traveling nurses. Now, since then, I’ve had some…

People are moving into the area, they have a short-term job here, contract work, insurance claim, all those kind of other things. But the lion’s share for the first probably two, three years was all traveling nurses.

Dylan Silver (14:40.049)
Let’s talk about finding those renters. Are you going to the hospitals? I know some people will have a relationship with the health care facilities organizations. Other people will just have a target avatar for a renter. And so which category are you following to, or maybe a mix of both, to fill these midterm rentals?

Justin Cambra (15:00.024)
So I used to manage it, self-manage it. Now I have a person that manages it for me. But when I was managing it, I was on the Seattle Facebook group for traveling nurses. But really, and then I had a…

I would post on, gosh, what was it at the time? It got bought by apartments.com. I think it was called Cozy. And then I was posting on where I get probably 90 % is all on Furnish Finder. But today what we do is we can dual list it on Airbnb, extended stay, 30 day plus, or at the same time we’re on Furnish Finder. But Furnish Finder’s been gangbusters ever since I got on it. Great value, very low cost.

next.

Dylan Silver (15:46.373)
I’m unfamiliar with them, break that down for me and our audience.

Justin Cambra (15:50.19)
Yeah, the just like Airbnb is tailored to people who are traveling and are looking for an alternative from a hotel. People who are traveling in an area and looking for longer terminal. There’s like extended stay hotels, but most people are using Furnish Finder as their vehicle to find all these properties. You can use Airbnb as well for like 30 days stay or more, but it’s a little bit more.

stuff to sift through versus if you’re just going and looking at furnish finders. They’re typically set up for one to six months stays for people and you know it’s very the user interface is not as great as Airbnb. There’s not as much money behind it but it’s very very functional one from the host side and then two from the the tenant side.

Dylan Silver (16:36.453)
Airbnb is incredible, man. I don’t have any deeds in my name or an LLC that I own, but I just, have, so many Airbnb investors. It is so incredible how much they’ve disrupted the world’s real estate market. Like to the point where everyone takes notice, you know, big players are trying to pass regulations to get them ousted from it. You know, it’s, it’s incredible. They’re like in a way, not just providing a service to people who want to stay in a home versus a hotel.

and to investors who want to do short term rental to increase their monthly cashflow. But they’re also like democratizing the real estate space. They’re being the Robin Hood because they’re bringing this ability to, you know, be a maximum cashflow real estate investor to almost anybody. Now, granted, you can lose your shirt. And I’ve heard stories about this, of course. And then…

Justin Cambra (17:33.186)
Yes.

Dylan Silver (17:33.891)
I know someone in particular who ended up going all in, all in on Airbnb and then ended up getting kicked off Airbnb for a host related complaint of some kind. And then what do you do at that point? Right? And you know, this person had spent $70,000 in furniture and they were just brand new and they financed it. So they were like, what do I do now? But they ended up getting out of that hole. But I say a lot to say just

Justin Cambra (17:45.303)
Right, yeah.

Justin Cambra (17:51.736)
Cheers.

Justin Cambra (17:57.157)
man.

Dylan Silver (18:01.883)
The avenues that are out there, you’re talking about listing it on a midterm rental and a short term rental concurrently. Genius idea. I don’t know how many people are doing that. Probably not many. Just as an agent yourself, I don’t know if you’ve heard of this strategy, but it was brought to me by one of my podcast guests. For homes that are currently sitting on market, and the seller’s open to it, and it’s sitting on market for a while, they don’t want to take a price reduction, they can list it out on Airbnb.

and then let prospective buyers know, hey, it is currently listed on Airbnb, so we’ll have to go schedule around the bookings. You know, it’s been listed for X amount of days. We’re not taking a price reduction, but it works out for us as a seller because we’re getting our money. And so we’re gonna get the money when it sells. We’ll take the appreciation when it sells. And for right now, yes, showings are maybe limited because there’s people there, but we’re getting the money.

Justin Cambra (18:58.06)
We, on the listings I have, we haven’t come across that yet. Typically it’s somebody that’s moving versus an investor selling, but it is a great idea, especially if the seller doesn’t need to sell, right? Like if they’re trying to get top of the market pricing, that…

That way they’re still getting some income while they’re listing the property. Typically my clients are, hey, I gotta sell 30 to 90 days is their ideal target. that short term income, although good, can then help, it could delay or you might not get your ideal buyer. So we haven’t dabbled into that yet.

Dylan Silver (19:23.269)
now.

Dylan Silver (19:37.657)
It sounds like you’re very active as an agent. That’s kind of, that’s also rare, I would say. Most agents have to, you would think there would be more of it, but people who are active in the single family space tend to be less active as an investor. How do you manage to do both?

Justin Cambra (19:54.286)
So right now I’m actually going all in on the agent side because when I left Amazon, I got into development and I very quickly learned it takes a lot of cash because you cannot guarantee when you’re going to get your permits. And so like I have a lot of holding costs on my development stuff. So I’m like, OK, let me generate more active income. And so the agent business is actually I make more part time than I did at Amazon, which is awesome.

Dylan Silver (20:09.297)
Mmm.

Dylan Silver (20:21.029)
Congratulations! Let’s go!

Justin Cambra (20:23.992)
So, but then I’m like, well, I’m trying to travel as well. And so like, I literally I’m in town, I make money. I go to travel, my pipeline goes down, make no money. In town, I make money. It’s like this sawtooth, right? So was like, okay, I need to get a team. So now I have four people on the team and you know, this is April, 2025, we’re doing five transactions now for this month. And we’re having like the best month ever and the team is training. And so I’m really, really pushing that, but

Really the genesis of me going in, leaning in more, is because I have $10,000 a month of holding costs. So, you know, that’s…

Dylan Silver (21:02.669)
Ugh, yeah. Your back’s up against the wall. There’s no, there’s no, it’s not like you can just take your foot off the gas.

Justin Cambra (21:08.686)
Exactly. And the other thing is like, just love Roll Estate, whether I’m buying it or help other people buy it. So, you know, as an agent, it gets me that adrenaline rush helping them. But the agent income also helps me buy more deals and get more deals for myself in my pipeline.

Dylan Silver (21:28.145)
Let’s talk about pivoting a bit here. Let’s talk about travel. Let’s talk about going abroad. I saw that in your bio. I love to travel. I had a passport as a kid. I’m 31 now. I got a passport again as an adult. I want to say almost two years ago in December of 2023 just totally opened my eyes. I say people if you’re thinking about investing in your education, if you’re thinking about going to a conference, also take a look at traveling.

because I feel like the most learning that I’ve ever done in my life was going to developing country. Like there was unbelievable amount of learning that I saw in that experience. So tell me your travel experiences.

Justin Cambra (22:07.648)
Yeah, I’ve, you know.

Back when I was in the corporate world, actually worked almost, I think it was 21 years. And I never took a sick day. And I was just always focused on everything and I didn’t do a whole lot of vacations and I always scheduled everything around work. And so when I left, when I immediately left, just got right into it. I went to Mexico a couple of times, I did a cruise to Alaska, I went to Iceland. And then it just kind of like, once you start traveling,

It’s just like, it’s like my new thing that drives me. we’re actually going to a cruise. We’re flying to Miami Saturday and then doing our cruise. But we were just in Costa Rica a month ago. So if I don’t take a trip every month, I’m just starting to get like all into it.

Dylan Silver (22:57.389)
I know what you’re talking about. Yes!

Justin Cambra (23:00.59)
So now I’m like, one more reason to do more agent income stuff to where I was like, okay, if I do more of that, then I can take bigger trips to more fancier places. I started tracking how much I was traveling and I think I was like, 2024 was 116 days. So almost one out of three days. And then for 25,

I think I have about 100 on the book. So in terms of what I’ve already traveled plus what’s already in the pipeline, it’s about 108. So I would love to keep that ratio. One out of, you know, effectively one out of three days I’m somewhere in the world. you know, back to your original point, you’re talking about passport. And…

I always think about it because I love that. to me, in my mind, like that’s the new currency, like passport stamps. that’s to me, I’m like, I look at that book and I’m like, I remember that was Costa Rica or that was Belize or Dominican Republic or Italy, you all the, you know, it just takes me back to when I was there, those stamps.

Dylan Silver (23:56.495)
Yes.

Dylan Silver (24:08.859)
How many languages? Is it English and just English or can you can you dabble in a couple? Okay, I’ve been to Santo Domingo, right? And there is for my money to our listeners, some people will disagree with me for my money. English is not happening in Santo Domingo, Justin. There is there is no English happening. You’ll go and you’ll be there’ll be like some heavy broken English. You can’t have it’s not Punta Cana. You know, it’s not if you’re going to Mexico, it’s not, you know, Cancun or Tulum.

Justin Cambra (24:12.95)
Just English, yeah.

Justin Cambra (24:25.904)
Ha ha ha ha.

Dylan Silver (24:38.289)
Santo Domingo is the capital of the country, military, like that’s the Dominican Republic. You’re speaking Spanish or nothing’s happening. So that was my experience. Now, have you thought about doing any international real estate investing or is it really more just for the experience for you?

Justin Cambra (24:46.946)
Right.

Justin Cambra (24:56.218)
It’s all about experience. Like I, my thought is, like, Hey, let me invest where I know. And I’m actually, you know, you know, at the peak, would say I was at 45 properties of which like probably 80 plus percent were out of state. So I’m actually trying to shift more one hour from me in Seattle because I can have more control. And so like, I would rather have an investment here that generates money.

that lets me travel versus putting something in, because I don’t want to learn a whole new country and insurance and mortgages and all that for another country. Like that’s just to me wasted brain space. I’d rather make the money here, have that money, then I go travel.

Dylan Silver (25:32.079)
Yep.

Dylan Silver (25:41.627)
You know, I was thinking about investing internationally, but you just broke it down so great for me. I’m like, I am gonna do an hour from Dallas, Fort Worth, Metroplex, not anywhere else. Let’s base around here and then maybe I can go travel, you know, 100 days of the year. Justin, tremendous conversation here. I loved having you on, but we are coming up on time here. Where can folks go to get ahold of you?

Justin Cambra (25:49.431)
Yeah.

Justin Cambra (26:02.04)
So right now where you can find me as on Instagram is the main area that I’m at. It’s at 4jccambra, which is just at 4jccambra.

Yeah, exactly.

Dylan Silver (26:17.039)
was a rooster that we’ve got outside of the podcast studio. Justin, thank you so much for coming on the show. I got great value from this. Thank you for providing value to our listeners. Thanks for coming on, Justin.

Justin Cambra (26:28.163)
Thanks for having me.