In this conversational interview, host Christian Osgood and co‑host Cody sit down with Northwest MLS power‑broker Jesse Lee to trace his unconventional journey through real‑estate. Jesse earned his license at 19, dabbled in mortgage origination, and quickly moved into brokerage and early house flips. The 2008 crash led to foreclosures, a short‑sale, and a personal bankruptcy of roughly $100k, experiences he now frames as formative rather than fatal. After learning the rehab trade from a seasoned flipper through low‑fee listings, Jesse shifted from pure fix‑and‑flip to a hybrid model, deliberately retaining at least one property per year and eventually building a buy‑and‑hold portfolio. Today his holdings consist mainly of single‑family rentals, plus a duplex, a triplex, a small mobile‑home park, and expanding RV‑pad rentals, all focused on affordable entry‑level units to serve a broad tenant base. He emphasizes cash‑flowing, long‑term fixed‑rate debt as the safest way to protect real‑estate assets, and he now embraces debt when it funds immediate or value‑add cash‑flow. Throughout, Jesse positions himself as an ordinary, non‑degree‑holding individual who leveraged community resources, online education, and perseverance to achieve the American‑dream through real‑estate investing. The episode closes with a teaser for the next show on marketing.
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Yep, that's how we define it. Cash flow on long-term fixed-rate debt. If you can do that again and again, that is the easiest way to not lose your real estate. Hello, welcome back YouTube. I'm Christian, this is Cody, and we're joined today by the one and only Jesse Lee, the menace of the Northwest MLS. Fantastic real estate investor, fantastic value-add investor. Really excited to have you on the channel, Jesse. Now we heard you speak— we actually got to speak with you in Portland recently. I love some of your background story. What you've done is absolutely incredible. Where you came from is incredible. Can we just open with hearing a little bit about you and how you got started in real estate?
Well, I guess we could kind of just dive right into it, really. I, you know, I have a little bit of a, I guess you can say, colorful start, really. Definitely didn't start with real estate, but, you know, just kind of being a I guess menace was a good word, right? A little bit of a teenage menace, I guess. But I got my real estate license fairly early on in life. I was 19 when I got my license. And at the same time, I was doing, or I got introduced to doing mortgage origination. This is 2004, '05, somewhere around there. So it was shortly after I graduated high school. And, you know, I'm not very detail-oriented, so I kind of figured out relatively quickly that I hate doing mortgage, and I transitioned to real estate sales as a real estate broker. And, you know, that was, you know, probably '05, '06, and into '07 where I was selling a few houses here and there. I was still doing mortgage here and there, but at that time a mortgage loan officer made probably as much as a real estate agent does on one transaction. So it's, you know, 2-3% was not unheard of, even more, you know, making that on one deal as a loan officer. So being young and not really educated and making a fair amount of income, then, you know, I bought a couple houses and thought I was brilliant. And, you know, then we had the the actual real estate crash and the recession. And from there, you know, I foreclosed on one of them. I ended up short selling another one, and, you know, eventually that led into my bankruptcy. So it was kind of a, you know, I rode that wave pretty good going up, and I kind of rode it all the way back, right back down. So You know, from there I was more or less kind of out of business like a lot of people I think were at the time. And, you know, the resources we have now online and the education and the people who are out just happy to give free advice and guidance, it's just, it wasn't the same then as it is now. Even though I don't feel like it was that long ago, the community is a lot bigger and stronger and the technology is a lot further ahead. But at that time, you just, you go to a real estate office and you sit there and do floor time or you do open houses, and I was calling expired listings actually a lot. But it, you know, I think there was good people around me. It's just, it was, again, it was just different. So I eventually, clinging on to, you know, life in this business, I was— I managed to have a conversation with an investor that I had met a few times, and The conversation led to me doing a couple listings at a flat fee, a really cheap price, right? I don't know, it's like $2,000 or something to list the house, flat fee, which at the time for me was great, right? I'll take 3 or 4 of these listings at $2,000 each and at least it puts gas in the tank and it put food on the table and was more than what I was making, which is nothing anyway. I took that and this person started at that time ramping up doing their flip projects and it led to me doing a high volume of listing sales. So I got to list several houses and oftentimes I'd get paid more than the flat fee, but more importantly, I got to watch someone who was experienced rehab houses from start to finish. Everything from their acquisition to selling the house. I got to see this play out over and over and over again, and I got to see this remodel process happen several times to the point where I was learning how to find these deals as well. And I can bring these deals to this person, and they would let me partner with them on it and kind of show me, this is how we do this remodel, this is how you start, this is what you do in this, and so forth. So That eventually led to me doing several projects with this person and I still do even now sometimes. And that also led to me eventually buying my own and kind of doing the same thing. And also what he did for me I do for other people now, too, where they find deals and I partner with them on it as well. So it's kind of come full circle at this point.
So getting back into the real estate space, were you jumping into these rehabs as fix and flip, or were you doing it where you'd fix it up and hold it? What did that look like?
Everything was fix and flip. You know, I, I can look back right now, you know, hindsight is always 20/20, right? Where I can look at it and think I should have kept so many of these. But, you know, it was, it was good income. It was great experience because we can take something that's that really should have been torn down and take that and make it a house again, right? And whether times where I made money or I didn't, but at least it's going through this process and learning how this thing works and how we're supposed to do this and learning how things don't work as well, more importantly, where it did eventually end up just kind of becoming a job, right? It was a, it was a high-paying job like you do one project and you make, you know, $30,000, $40,000, $50,000, even $100,000, but that's it. You sell the house and you're done, right? And I made this realization probably right before COVID started, right before the moratoriums and the shutdowns. And I'm thinking, you know, a 30-year mortgage is— 30 years is about— from now is about my retirement age. And if I just keep selling these houses, I don't really have anything else. I'm not going to have any kind of retirement or anything. So I decided I need to keep one house at least every year out of all these things we're doing. And I ended up keeping like 8 of them, I think, the first year. So that's when I really— I think that's when I really actually started doing real estate investment as opposed to just buying and selling inventory, right? It's no different than buying and selling anything else, really. It's just what I'm buying and selling just costs more than, you know, cars or whatever, hardware, whatever it is, right? So the houses end up becoming inventory, and that's just no different than owning a store, right? At this point now, you know, I'm buying and keeping as many houses and as much real estate as possible where Now I actually think what we're doing is real estate investing, at least starting to do it properly. So even though I've had my license for years, I don't really feel like I've been doing this job right until the last couple years where now I own several houses that are rented. I own several properties and lots of, not as many units as you guys, but I've got several rental units now. And I don't have any intention of selling several of these properties. So that's kind of where we need to get to the point of just buying and keeping these things. I know a lot of people buy rental property and they have a W-2 job to finance all of it. My job to finance all of it is fix and flip or wholesale or brokering or whatever it is, but all of that is just to fund buying and holding property.
Awesome. What does the portfolio look like today for you?
It's mostly single-family homes. I started with those because those were the deals that I already knew how to analyze and that would already just come kind of on their own to me at this point simply because I'm in this industry and I've been flipping houses and I'm a broker. That's just kind of— I don't want to say it's the low-hanging fruit because in a way it's not, but Those are the ones that I'm already— I already have that business available, right? So I'd find several of those. We did buy a duplex and we bought it, then we bought a triplex. I do have a small mobile home park I got with somebody last year. And lots of RV pads are things that I'm adding on right now. I really like the mobile home park model. You know, somebody put it in a way where it's, uh, you have a low and wide stance. That's the best way to endure any kind of economic downturns is, you know, be as wide as possible, right? Can't fall over when you're the wider you are, right? And I think the, uh, my favorite price point, which is it always has been no matter what I've been doing, is whatever the median or entry-level price point is and whatever it is that I'm working with. That's the, the stuff I like working with because that has the biggest buyer pool. That is the biggest customer base. There's a lot more people who need to rent something entry-level than there are people who need to rent something luxury. And what I've decided is I want to be serving a base of people that don't make their decision based on what the stock market might be doing or what the economy might be doing. And if they do, it's a lot less of a degree than somebody who is buying a $3 million house, right? That person is definitely paying attention to a lot more economic factors than someone who is renting a $900 a month RV space. So I feel like serving that customer base is going to be a lot more predictable. Right, so that's what I'm working with now, a lot more affordable housing stuff.
Having gone through your bankruptcy, how did that shape your business and your respect for debt?
You know, it's funny thinking about it now because I filed for bankruptcy over like $100,000-some of debt, and it's various things, right? It was, I think, a HELOC or two, and, you know, car debt, some consumer debt, and I think now like $100,000, I spent more than that in the last month, probably. So, and that's on, you know, various rehab projects. But to think that I did a bankruptcy over something that now just seems so small, right? And it's not a small amount of money, but it's— it really isn't anything that is worth filing for bankruptcy or stressing over, I feel like, at this point. But I think what that did for me is both going through foreclosure and going through bankruptcy in my 20s is I've already experienced things that a lot of people are afraid of. And now that I can look back and think that it really, it wasn't really that bad, right? It's not the end of the world that I don't go and make reckless decisions now because of it. But I'm also not afraid to take on more debt as long as it's the right kind of debt, right? If that makes sense. So I, um, I'll always be fine borrowing money to buy real estate provided that I'm either going to cash flow right away or I'm going to cash flow after whatever value-add I'm doing. As long as I can do that, then the debt isn't really something I'm worried about.
That's awesome.
Yep, that's how we define it. Cash flow on long-term fixed-rate debt. You can do that again and again. That is the easiest way to not lose your real estate.
Right. Yep.
Well, before we wrap up, is there anything else about you that you would like to share with people that are listening?
You know, I, I like to be an example of just an ordinary person who can do this business and I don't even feel like I even do it all that well, really, a lot of times, but I do well enough that it's the only thing that I'm doing and then I make a living off of it. And I feel like I have a reasonably good living and can support a family, one-income household and all that. So really, I'm, I'm the most ordinary person that you can think of. I don't have any degree. I don't really— I'm not even particularly educated, really. And I didn't really— I didn't do terrible in school, but I don't— I'm not a straight-A student by any means. So the fact that some person like this can come into real estate and make a living off of it, it's— it is proof that it can be done really by anybody. And even coming back from, you know, absolute zero, right, where you make a good amount of income as a real estate agent and as a, basically a child, 19, 20. And I know it doesn't make you feel great that I said that, 'cause that's like your age. But, you know, being able to make great money, great income, and then go to completely flat zero, nothing at all, stealing groceries and diapers to just back to making a great living again. It is a testament to how powerful this industry is. And really, it's going to sound cliché, but this is something you can really have the American dream through, and it's through real estate.
That's awesome. Well, that's it for this episode. Next week we're going to be talking about marketing, because if you guys haven't seen Jesse on social media—
now you have.
Yeah, now you have. And his stuff is Hilarious. The creativity and authenticity of his marketing, I think, is really unique. We've learned a lot from it, um, so we're going to share that with you guys next week. If you haven't yet, like, follow, subscribe, and we'll see you next Monday.
