In this YouTube presentation Christian Osgood walks viewers through the four distinct phases he used to grow his rental‑property portfolio from virtually nothing to a projected $100 million in assets. He begins by defining Phase 1 – the “first‑deal” stage where the sole priority is acquiring a single property, often using creative financing such as seller‑financing or low‑down‑payment loans. Phase 2 covers scaling to a handful of small multifamily units (duplexes, triplexes, four‑plexes), establishing basic systems (self‑management, simple tax filing) and achieving financial‑freedom milestones. Phase 3 focuses on building a professional team – contractors, a property‑management company, a CPA, and capital‑raising partners – while emphasizing the need to avoid over‑expansion and to leverage properties for liquidity. Phase 4 describes the transition to an enterprise‑level operation: multiple property‑management firms, strategic equity partners, mergers, and a layered leadership structure that allows the founder to act as a CEO rather than a hands‑on operator. Throughout, Osgood shares personal milestones (growing from a $1 M portfolio to $56 M and on track for $100 M), concrete advice on deal‑finding, risk management, and the importance of aligning the business size with personal goals (side‑hustle, high‑paid self‑employment, or a full‑scale real‑estate company). The talk is instructional, motivational, and peppered with cautions about scaling too quickly.
Chapters
All right guys, going horizontal here for today's live, switching it up a little bit. The, uh, the main studio is currently getting a little bit of work done, so while that happens, uh, joining you guys from my phone. So welcome to the, uh, the lower office here, guys. Still building it, but, uh, uh, there we go. Welcome to the, uh, the bonus room. So on today's video, I'm going to talk about the 4 stages of actually building your rental business. And so if you are right now in the process of starting, you're trying to figure out, okay, where do I go to build my business starting from scratch, I think there's 4 main phases. Phase number 1, you have no money or little money, you're in a 9-to-5 or leaving a 9-to-5, you're trying to break into real estate. So like, there's ground zero, I don't own any real estate. Uh, phase 2, it's gonna be I've got this buying thing down, I've closed a few transactions, I'm ready to go bigger and I want to scale. Stage 3 is I'm doing multiple transactions every single year and I'm starting to add systems and processes. You're getting your PM company, you're legal, you're counting down, you really start, you're a solopreneur, and then you can get into the enterprise level. This is where you get to thousands of units. Now today I have about a $56 million portfolio. By the end of the year, I'm closing on an $8.5 million transaction here in just a little bit, closing on a $6 million transaction and looking at another 10. By the end of this year, I'll be right around $100 million in total portfolio value. Uh, as a note, I had a net worth of less than $1 million and a portfolio of properties that were worth combined right around $1 million 5 years ago. So scale from $1 to $100 million in real estate. These are the 4 phases that I've found. I'm sure people who are farther than me know phases, you know, 5, 6, 7 to play in this game, but This is where I'm at, where I can actually speak from actual experience of building a nearly set— well, how many figures is that now? 7, 8, 9-figure portfolio. So, uh, stage number 1, when you are starting, the first thing that you need to do is you need to find a deal. If you're brand new, you're starting, it's not finding the money, it's not building the teams, it's not getting the account. It is none of these steps. All you need to do, the only thing that anyone needs to do to move to the next level is simply go out and buy yourself a property. If your goal is to become an investor, you're a 9-to-5er right now, you need to actually go out and buy the darn property. There's only one way to be an investor— invest in a property. Pretty obvious, right? Now, for me, this was, uh, when was this? This was 2016. I bought one property. It's a live and flip. I fixed it up. I had a roommate. My wife and I got married. She moved in. I kept the roommate for another year, eventually turned into a rental and bought a house. That's how I got into my first rental property. Loved the income, didn't love being a landlord to my one tenant. Skip to the next phase. I buy one duplex, I buy a second duplex. So we start buying all these properties. You can copy this exactly, by the way. So you start buying all these properties, you get the rentals and go, okay, I did one FHA, so 3.5% down, closed on it, house hack. Awesome. Now we're at 3 total properties. My house, my rental duplex, my rental condo, sell the condo, buy another duplex. Now we sell 3 properties with 4 units. That is entering phase 2. I started doing some renovations. I got a contractor team. End of the year, I filed taxes for multiple companies. I had 2 properties were in an LLC. Now you're starting to get into, okay, we're getting systems and processes. You're not even a solopreneur yet. You're just a hobby investor here. You can be done at stage 2 if you want to buy a duplex, triplex, or fourplex every year. For the next 10 years, you can absolutely retire on this. Phase 2 is the minimum that you need to reach financial freedom. So Phase 1, just I'm brand new and I'm buying a deal. You still get ahead of a lot of people. Phase 2, very easy to do. I need to find in the billions of properties out there, I need to find one deal every single year and move forward. Now, if you don't know how to do this, regardless of the amount of money you have, you need to learn how to get creative. You can follow this channel for all the creative finance, the seller financing, the bank Creative Finance, you can go zero down if you don't have money. Don't let that be the block. I started this adventure with very close to $0. My first multifamily entering stage 3, like a real multifamily property, seller finance, 38-unit. You guys hear about it all the time on this channel. Then I bought a 6, 12, a 10, a 25, a 26, 44. I closed on 76 here today. We bought all over the place. You can do the same thing, but that's stage 3. What do you need for stage 3? 1, you need to know how to get creative beyond the money you have. 2, you need to realize if I have a deal, I can find more capital. So I'm buying beyond the money that I have in my bank account right now. That's stage 3. What systems do you need to succeed here? You need to have multiple good contractor teams to keep your properties maintained and potentially to do some renovation projects. That's where a lot of the money is for a newer investor. You need to take something that is not worth as much as it can be and get it worth absolutely as much as it can be. You can borrow against that. You could get liquidity out of that. But that's how you move forward and feed your business. You need a great property manager. I had to start my own property management company because I couldn't find one in my market. But that is something that you're going to need on the team. You're going to need a CPA, a really good one, because you don't want to get killed by taxes while you're making a lot of money in real estate. Trust me. I had one year where I thought I was going to pay zero in taxes. Turns out paid $200,000 in taxes. You don't want to do it. What I want to point out is that if you're sitting here at phase 1, we're going to get to phase 4 next. If you're sitting here at the beginning of phase 1, you're like, I don't have any real estate, or I just bought my first rental property. If you are sitting right there, you do not need the perfect contractor, the best property manager. You don't need the biggest banking relationships. You don't need all the capital. You need to find a deal. That is all you need to do. In phase 2, you don't need the best of all of these things. You can mostly self-manage. You really don't need a very complicated CPA at all. You can still file your taxes like any other average person. It's right around the time that you're like, hey, I'm going to get over 30 units. I'm going to start building my portfolio, buying bigger multifamily. That is where we start getting— by the way, in the chat below, you guys are all welcome to ask questions. Coltix, yo, Zed, hello. Guys, this is, this is how you play the game, though. You can move into number 3. Now is where you start building the teams. You get some strategic partnerships. You might have found someone who's helping you fund some deals you become closer with, and you might have some strategic partners along the way. You might have some general capital partners. In this phase, it's about getting excellent. You do not want to move from stage 3 to stage 4 too quickly. Now, the first thing that you're going to look at in stage 3 You don't want to expand so fast you're going to implode. I see a lot of people do it. You all of a sudden get the skills to buy beyond your money. That means you can buy literally anything you can negotiate. When you unlock this power, the tendency is to buy a lot of everything. I've had plenty of friends buy hotels, multifamily, office, retail. The market changes this much and all of a sudden their cash flow goes from super positive to super negative. The whole ship tanks. They don't have the construction crews, the management crews, the accounting to handle it all. Do not scale yourself to death. There's no reason to drive that fast. This is the time where you really get good and nail the systems. You make sure that you've built a team of mostly third-party contractors. You can now run the business just fine. Let's talk stage 4. That is where I— so I sat in stage 3 till I got to about 325 rental units. That was the sweet spot. To get to the next stage, here's what I've had to do. I've started two property management companies, seller-financed one to a great operator, and then I own my one and I'm scaling it down here in Texas. I have my renovation teams that I still use as a third party. They work very, very closely with me and I'm large enough to be one of their main clients. So I get preferential terms, pricing, treatment. You build the business so it gets a little bit better. I have the lending connections, I have all these great things, but I get to a point where I can't be the CEO of Multifamily Strategy. I can't run the YouTube channel, the Instagram channel, buy the real estate, manage the real estate, hire the— I can't do everything all the time. So to scale beyond— and again, the bottleneck for me hit right around 300 rental properties. I can't be the CEO of every single division. Now you need to start relying on other people if you want to scale, if you want to retire. There— I want to point out there is no lack of capital. You can make a ton of money getting to 300 rental properties. That is enough to retire on if everything cash flows. You're doing so, so well. So what do we actually do? Stage 4, my property management company. I'm looking to bring on a strategic partner. We're looking at a merger with a more established firm. While I have the business practices, the accounting, the strategy, the leasing, the advertising, I'm not as skilled as another property manager in my market who is there boots on ground all the time, who understands the market, the signage, which tenants go to which coffee shop. That level of detail is impossible for me to get into while running the rest of the business and the acquisition and the whole thing. So I'm bringing on an operator and yes, I'm giving some equity in my property management company to do that, but I'm putting the correct leadership into place to bring experts in to the company. Acquisition. I'm bringing on a few larger partners, people who have done similar businesses to me who are facing the same bottleneck. They're like, hey, I bring X and Y to the team. I am a good marketer compared to other real estate investors. I tend to do a little bit more on the marketing, the outreach that I can do this beyond what a lot of other investors do. I know I bring that to the team. I'm a pretty darn good negotiator and I'm a great capital raiser. These are all very helpful people who are stronger than I am or faster than I am in legal, in detail, in contract coordination, in different asset types. If I bring in people who specialize in affordable— I do a lot of affordable, but people who truly specialize— here's what happens. Caleb Hommel is an amazing deal finder. Him and I have partnered on a lot of stuff. We're looking at bringing in a third partner to the core holding company who brings a ton of legal experience. In fact, they happen to be a very well-established lawyer who has an— it's a larger portfolio than mine, but lower equity. They have a lot of syndication experience, so they have a lot of different deal structure experience. But bringing the lawyer onto the team, while it dilutes the equity, it allows us to go from 300 to several thousand units. I would rather personally have a third of 3,000 units than half of 300 units. I think that math's for me. There are many of you who have no interest in doing that business. The beauty of this is you really only have to get to phase 2. Now there's many phases beyond this, and I, while I know them conceptually, I never talk about anything that I haven't actually done on this channel. I want to always make sure that we are not just talking in theory. So for what you want to do, know where you actually want to head. Don't build a business that's larger than you want to build. Your goal is just, hey, I want to get $10,000 a month in financial freedom. Awesome. You're going to do the beginning of stage 3. You'll get big enough to do that and you'll be just fine. It's very easy to do 4 transactions a year. Average deal size is 25 units. You can add 100 units to your portfolio every year for a sustained period of time. There's going to be a point where like, hey, I'm— I have way more money than I need. Awesome. Buy those on cash flow, increase your income. You're good to go. If your goal is, hey, I love building business, I want to scale as far as I can, you just keep playing the game as far as you want to. I am finding that it is more fun to work with other like-minded people and to grow the business, to add employees. Today we employ about 40 people. I enjoy being able to do that. That is something that is meaningful and important to me. I like coming in on the property management side, and I like saying, hey, we actually provide better housing at a better price for more people in every market that we touch. That come in and have notable positive impact. On renovations, I like knowing that I can take harder projects than other people want to do and we can knock them all the way out of the park. These things are meaningful to me. It's the stuff that I want to do. Build your business to where you want it to go. That's the main point here. Make sure you're always hitting that. Say it one more time. Know what phase you're trying to build to, map it out, get it there. That is the main way that you're going to build this business. And don't try to skip steps. Don't try to go from 1 to 4. Don't try to skip step 2. I think you should just buy that first rental property, nice and simple. Then learn how to scale to multiple transactions a year. They don't even have to be big deals. They can be duplexes to 15-plex. It's fine. Just start buying bigger than you think you can and do a few transactions. Once you get the rhythm for it, now you're making a business out of it. Essentially, you're moving from out of the game to into the game, you're going into a, you know, super startup mode for phase 2. You're in a brand new business startup. Phase 3, you're self-employed. Now, granted, you're a very rich self-employed. If you do this correctly, you're a very high-paid self-employed. But don't confuse that with having a business. Stage 4 is you're actually turning it into a business. I have strategic partners. I have extra layers of leadership. I have people who own different silos of the company. That is where you start getting to the point where it's like, oh, instead of having just like one assistant, I employ 40 people. That's pretty cool. I believe probably next year we're going to be looking at, okay, we need to buy an actual office somewhere because we have 4 companies that are all growing, all in real estate that need to be housed somewhere. We can use more underwriters. I can use that. You actually get to build a company out of it, but only if you want to. Just identify, are you trying to do a hobby for financial freedom? Is this a side hustle? Is this self-employment, highly paid self-employment, or are you actually trying to build a business? Once you get past that level of thousands of units, there's many, many, many more levels above that. But again, we're always going to teach to what we've actually done here on this channel. So if you want to know the stages to go from zero to $100 million portfolio, that is what has worked for me. I believe this will work for you as well. If you guys have any other questions, always feel free to let me know in the comments, but I will see you guys all on the next episode.
