In this video Christian Osgood presents Rule #27 of his 35‑rule real‑estate series, adding a third essential criterion to his existing two: a deal must be enjoyable. He explains why investing that feels like a second 9‑to‑5 defeats the purpose of financial freedom, and he outlines a decision‑making framework that asks (1) Is the location right? (2) How will I buy it? (3) How will I never lose it? and finally (4) Will the process be fun and enhance my quality of life? Osgood illustrates the concept with personal case studies – small, boring triplexes that added little value, a challenging 38‑unit value‑add that was hard but rewarding, and the Robin Hood Village Resort, a seller‑financed, character‑rich property that combined creative finance with passion. He shares metrics (units owned, financing structures, timelines) and practical advice for beginners: start with a duplex in a desired market, master the first two questions, then ensure each subsequent acquisition excites you or pushes you into a new, enjoyable challenge. The overarching message is to avoid turning real‑estate investing into a drudgery‑filled job and instead build a portfolio that fuels both wealth and personal fulfillment.
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Hey YouTube, it's Christian and I am here today to share with you guys our next rule of real estate. Now we're on rule number 27 of our 35 rules. We are almost done with the series. Cody and I are discussing introducing maybe 5 more, but either way, we are very, very close to the end of this series. Today's rule is actually an extra piece of criteria. We look, we talk all the time on this channel. How do you buy it? How do you never lose it? The 2 criteria for how to buy absolutely any piece of real estate. However, as you progress, there is one more rule that you actually add to that. And that is what we're going to be talking about today. The rule for rule number 27 is it needs to be fun. Now, before you just skip this video and go to the next one, this is actually very important. I'm going to break this down for you very specifically. There's a reason why it needs to be fun. Now, if you are pursuing real estate, you want this passive income, you're trying to do buy and hold real estate or following Cody and I and looking at the whole creative finance thing, how do I acquire and hold real estate? And how do I answer those questions? How do I own it? How do I never lose it? You're going to hit a point very quickly where it's going to feel like it's another job. If you're buying a whole bunch of real estate that's boring or you're not passionate about, and you're adding more and more to your plate, you're going to hit a point where it's just not interesting to you anymore. It's going to be stressful, it's going to be a drag. And what you've done is if you've left your 9 to 5, you've just created a brand new job for for yourself. And if it's a lame job, then congratulations, you've successfully reached financial freedom. You left the 9-to-5 to a job that you hate even more. We don't want you to do this. And we have gotten down that road where we bought so many projects on Class B properties where we're buying smaller properties. There's a couple triplexes for practical application, uh, two triplexes We didn't need to buy them. They were just a great deal. They were in our market. We're like, we should do this because this is what we do. Moses Lake, let's buy a couple triplexes in our core market that make absolute sense. They make money day one, excellent terms, long-term debt, totally fits the bill. I wish that we never bought those properties. They've been a little bit of a maintenance headache, not bad. They're very boring to me. They don't really move the needle one way or another. It's not enough units to change anything. Once we're at 100 units, 6 more small units don't really change our universe much. It's just a little bit more work for us and a little bit more headache, which is where we instituted this rule. You need to be doing something you want to do. You have limited time to live. That's why we do this whole breakout of the 9 to 5 thing. This is why we push for creative finance and passive income. You need to own your time. The time that you are spending building your portfolio should be enjoyable. You should get to a point where you absolutely love what you're doing. So you're going to do a few different metrics. When I'm looking at a deal now, is it in a location I want to buy? Answer that. So one, is the location right? That comes before we ask any other question. If yes, how do I buy it? Well, if I can answer that, now we're getting somewhere. Now we have the deal. How do we never lose it? Okay, we can figure out how to get it into long-term fixed-rate debt or pay it off before it balloons due. Then I've answered that. That's how I never lose it. Now the last question: am I going to enjoy the process? Is this something that I actually want to do that will enhance my quality of life, move me towards my goals, and be an enjoyable ride along the way? Another piece of practical application: our 38-plex, a very hard project. We bought that as a huge value add, lost money pretty substantially day one, which is not one of our principles, but we had enough cash flow to cover that negative. We got that to a performing property and it has been stellar. However, that was actually fun. That was a challenge that pushed us out of our comfort zone, put Cody and I on the map. At the time, I only had 4 units when I bought that 38-plex with Cody. He had 30. It was a little bit easier for him to wrap his head around. That grew us and it challenged us. Was it hard? Absolutely. Was it way harder than my previous 9 to 5s? Yes. Did I enjoy that ride? Absolutely. And I'm so grateful we did that project. It doesn't feel like those triplexes I never needed to buy. That moved the needle, that pushed me to a different level. And I had fun along the way. Not every second of the way, but overall had a lot of fun. Now look at what we're doing today, putting this into practice. We bought a lot of multifamily together. Between Cody and I, uh, we own, I think, 110 units between the two of us. If you count the triplex on the front of our resort, I'm over 100 units. If you don't count it, I'm at 98 units. Um, but we picked up about 100 multifamily units. That was my original goal with Cody. We said this 2-year goal, we hit it in less than 1 year, which is still insane to me. Picking up a bunch of multifamily in Central Washington, I'll still keep doing it. And I'm going to do projects that I'm passionate about now, not just I'm going to pick up any opportunity that makes money and makes sense. It's going to be how do I own it? How do I never lose it? And is this a project that's going to be interesting or fun or something that we really want to work on? And we have a few of those over there right now. Robin Hood Village Resort was a deviation from what we've always done. And I am a fan of staying in your lane. So why did we do a project like the Robin Hood? A million $1 million down, huge down payment, not in our core market. We are multifamily investors and operators. We even own a multifamily property management company called Multifamily Property Management LLC. I mean, we're as multifamily as you get. So why did we do a resort? The Robin Hood Village Resort is a magical property. If you have a chance to go out there, which, by the way, if you're watching this video, you're invited. You can message me on Instagram @ChristianOsgood. Ask me about it. We'll meet you out there. But magical property on the water, in the forest, historic cabins, tons of character, and the types of projects that we really want to do. We saw something where our skill sets and our team could really bring this to life. In addition, our director of property management is a short-term rental expert. Our designated broker Brandon actually runs some Airbnbs, um, in and out of state, as is his assistants. So we had the team members on our team to build this business and to do a new adventure. The main reason we did this is because we answered our first two questions. How do we buy it? Well, seller financed, $4.5 million purchase. That's $1 million down. Okay. And then we knew where that million dollars was coming from. So I structured our debt and our equity. We actually shared the numbers on the Robinhood in another video if you want to go into depth there. But we answered those questions. Now, is this going to be fun? It is the single funnest adventure that Cody and I have ever gone on. And I think funnest is a word. And if it's not, then it is now. We have had more fun doing this than we have any other project. It has so much character. It's so much fun. It means something different to bring people down to our own private bar that Bill Gates used to frequent all the time. He actually owns the adjacent property, but the Robin Hood had— it used to be an active pub and it had his Macallan 18, which is apparently his favorite beverage. But you have all this character and all this history and it's in one place, and it's really cool to be able to bring friends and family, guests down there and show them a piece of history that is completely unique. We have kayaks, great hiking, great fishing, great hunting. So you look at all these things and you go, this is going to be fun. It does make money. It actually makes a lot of money. We figured, how do we buy it? How do we never lose it? Well, we're going to let the Robinhood pay itself all the way off. Within 8 years, we're going to pay off the entire property. Instead of refinancing, we're just going to write a check for the whole thing. We did it because the adventure is worth it. And the story we're going to get to tell 10 years from now on how we acquired this, how we improved and expanded the campus, That's going to be a story worth telling. It's going to be fun, and the story is always worth more than the real estate. So how do you apply this to your investing? If you're getting started, focus on the first two questions: how do I buy it, how do I never lose it? Get into your market. If you haven't bought anything ever before, even if it's just the duplex, buying that multifamily will be interesting to you. It will push you. Now, I encourage people to buy bigger than a duplex. However, I got started with duplexes and I've done okay. Um, I, I would say in the grand scheme of things, I've done better than okay in the real estate game, which is why I'm here, uh, trying to help everyone watching the channel move forward faster. We moved very fast, very successfully. But if you start with a duplex in the market you want to start in, you're probably fine. And your next few properties, you're probably fine. If I started with the triplexes that I didn't need now, would have been a great deal, would have pushed me, would have grown me. But make sure it's doing that, and it's it's stimulating for you to go out and buy. If you're excited about it, do it. As you get a little farther, you hit your first few sets of goals, and you're finding, man, I can pick up this property, I know how to do this, but I'm kind of getting bored, or I don't know if I need the property, but I know how I'm going to buy it, how I'm never going to lose it. I would challenge you to stop and say, what would make this fun? And if it's not going to be enjoyable, go, okay, what challenge do I need to grow myself, to push myself to get to the next level. If you can find whatever that is, I would pursue that next step. That is when you diversify, that's when you do something new, creative, but that is how you expand and stay engaged so you're not just giving yourself a stupid job you don't want. You're actually building the life that you want to build. So if you want to do that, just remember, keep it fun. If you haven't yet, please like and subscribe this video. If you have someone who needs to be reminded to have fun playing this game, because there's a lot of people Give this video a share and we will see you guys next week as we start to get to the back end of wrapping up all of our Rules of Real Estate. And tune in tomorrow for our Multifamily 101.
