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Cash Flow Isn't Dead in 2025: You're Just Structuring Deals Wrong

Why day one cash flow is still findable in 2025: stop shotgunning offers, map both sides, and use the least creative structure that says yes to everything.

Cash flow in real estate used to be a really easy thing to obtain. More and more, I'm hearing online that people aren't finding deals that cash flow, and that it's been getting harder and harder. If you look at deal velocity over the last few years (the number of multifamily properties actually trading) it has slowed down a lot.

Here's what I've found: there aren't that many people doing truly good deals right now. So why is that? How are the people who are having success doing it? And is day one cash flow really that hard to find?

It's not a myth. Just this week, four people in my mentorship group bought their first deal: four people, four different markets, and we saw over 44 units purchased across the group. On top of that, I purchased a few deals that cash flow day one this week, while I was on vacation.

So something is different about how we're buying. Here's what it is.

Cash Flow Is a Function of Being an Insider

When you're negotiating your deals and trying to figure out where the cash flow is, it comes down to two things: becoming an insider in your market, and understanding what the seller wants alongside what you need.

Most people skip the second half of that. So start with your own half and be specific about it.

For me, a deal is made of long-term, cash-flowing, fixed-rate debt. I'm going to buy a property and it's going to cash flow day one, out of the gates. It has to. That's a rule and I don't deviate from it. My income goes up permanently when I buy that deal.

That definition carries some obligations, and they're the parts people cut when a deal is tight:

  • I'm raising enough money to actually have a reserve. Even going in low to no money down, the reserve is set up.
  • I've allocated for the renovations this project needs, up front, before closing.
  • It's structured in a way that pays me every month.

That's my goal, written down. Then I need to find out what the seller's goal is and write that down too: with the broker, or direct with the owner, which is usually how my deals go.

Stop Shotgunning Offers

Nobody in our group shotguns offers. We're not writing offers every day. I hate that model.

Most people in the group write one or two offers a month. That's it.

What we're doing instead is finding deals we actually think have a good chance of being accepted. We've talked to the broker or the owner. We've really mapped it out. And then we say: I think I have a solution where I get everything I want and they get everything they want.

That's the difference between volume and precision. A hundred offers built on nothing but a spreadsheet get you a hundred rejections and a reputation. Two offers built on a real conversation with the person who owns the building get you a closing.

One of my favorite books on negotiating of all time is Never Split the Difference by Chris Voss. Without trying to summarize the whole book, the title carries the idea: everyone gets 100%. It's always a win-win-win. I get long-term cash-flowing fixed-rate debt. All of my mentees get long-term cash-flowing fixed-rate debt: with margin, with a reserve, with the renovation budget set up on the front end.

The Deal Where the Seller Wanted to Retire on $10,000 a Month

So what does the seller actually need? Is it a specific price? A specific interest rate? Something else entirely?

I did a deal where all they wanted was to retire on $10,000 a month.

The problem: the property was only making $5,000 a month when they wanted to sell it. So how do you pay somebody $10,000 a month out of a building that produces five?

The answer was that we had a path to get it to $30,000 a month. It just wasn't there yet.

So we structured it so there were no payments for the first six months while we fixed all of their collection problems. And we didn't show up empty-handed to do it. We came in with a mission, with a budget, and with the capital already raised.

The rest of the structure looked like this:

  • We bought it very low down: 15% down.
  • The remaining money was structured with equity partners, because this seller couldn't finance 100% of it. They had a little bit of debt on the property.
  • Those partners wiped out the original debt and helped fund the initial renovation.

And here's what's important: the only creative piece of the entire deal was the payment start date. That's it. Payments need to start six months from now so we can run this property without losing money, get paid from day one, get collections up, get leasing up, and finish a few renovations: so that we can then pay you $10,000 a month, which is exactly what you want to retire on.

We wiped out their debt. We gave them their $10,000 a month. They got the exact price they asked for. We got income for the rest of our lives.

One deal. Then we did another deal two weeks later, and another two weeks after that. Different structures, very similar thinking.

The Real Takeaway: Use the Least Creative Structure That Works

Here's the piece that I think everyone in Multifamily Strategy is doing differently from the rest of the country.

We're not shotgunning offers. We're writing offers we believe can get accepted, by mapping out what they want and what I need, and then finding a way to say yes: even if the yes looks a little different than what they pictured.

It's yes to everything you want. Here's what it's going to look like. $10,000 a month? You've got it. It starts six months from now, after we clear your debt right now, take over the property, and execute this game plan to get you there.

Notice I'm not handing them the $10,000 immediately. We did a magical little thing instead: we asked what was the simplest answer that lets us say yes to everything?

I see two mistakes constantly in creative finance structures.

The first is that people hone in on one strategy and pitch the exact same structure every single time. You might watch this and conclude that the move is to always pitch no payments for six months. That is not what I'm saying at all.

The second is overengineering. When you get too creative, two things happen: your deal doesn't get accepted, and you make all sorts of mistakes so the deal doesn't end up looking how you wanted it to. I have gotten too creative before. It is very costly.

What you actually do is map out both sides and ask: what is the least amount of change I can make to ensure I get what I want and they get what they want?

On that deal, we were off by $5,000 a month of cash flow. So all we did was say no payments. One change.

And it's worth noting what the rest of the terms did for us. That $10,000 a month only carried 4% interest, which meant it was almost all principal. Every time we wrote that check, our equity went up and our debt went down significantly. The property paid for the property, and it cash flowed to us on top of that.

That deal helped me retire my wife. It also gave the seller exactly what they had always dreamed of: they got to truly retire from a property that was eating them alive. Everyone won, and it was the simplest possible answer.

Key takeaways

  • Deal velocity has slowed and cash flow is harder to find, but it isn't a myth. Four people in the group bought their first deals in a single week, and over 44 units traded.
  • Define what a deal is for you before you negotiate. Mine is long-term, cash-flowing, fixed-rate debt with a reserve and a renovation budget funded up front.
  • One or two well-mapped offers a month beats shotgunning. Talk to the broker or the owner first and write offers you believe will be accepted.
  • Find out what the seller actually needs (price, rate, or something like retiring on $10,000 a month) and write it down next to your own list.
  • Use the least creative structure that gets both sides to 100%. On a deal that was $5,000 a month short, the entire fix was delaying payment start by six months.
  • Over-engineering costs you. Too much creativity gets deals rejected and creates mistakes you pay for later.

If you can find the simplest answer that says yes to everything they need, in a way that lets you cash flow on long-term fixed-rate debt, you can buy infinite deals. Every time you close, your income goes up again, and again, and again.

That's the secret sauce. There's a lot more to it: the analytics, the math, the strategy, the conversation pieces, how you actually structure these deals, how you write the offers, and how you negotiate to get them accepted. But distilled to its simplest form, it's this: what is the least creative creative-finance method that lets me say yes over here and yes over there?

That's why cash flow isn't dead, and why every deal we purchase cash flows day one.

Watch the full video above for the complete breakdown. You can learn about my mentorship at mentorship overview, download our free course on getting started in multifamily investing, or join the Facebook group to compare notes with other investors working these structures.

Read the episode transcript

Original automatic captions. Names, numbers, and punctuation may contain transcription errors.

0:00 is cash flow myth. Cash flow in real estate, this used to be a really easy thing to obtain. And more and more and more I'm hearing online that people are
0:08 not finding deals that cash flow. It's been harder and harder. And over the last few years, if you look at deal velocity, like you look at the number of multif family properties traded, it has
0:16 slowed down a lot. What I found is there's not actually that many people doing truly good deals right now. Why is
0:23 that? How are people having success? And is cash flow in real estate, like day one cash flow, really that hard to find?
0:30 Well, I'm going to share this in this video. Uh, by the way, new to the channel, my name is Christian Osgood. I have bought hundreds of rental properties. I run a mentorship group
0:38 called Multif Family Strategy where just this week, four people around the country bought their first deal. Four people, different markets. Super awesome. We saw over 44 units purchased
0:47 this week. On top of that, I purchased a few deals that cash flow day one this week while on vacation. How do we do it?
0:54 And why are these deals cash flowing?
0:56 It's not a myth. What is different about how we're buying deals and how can you do the same thing? Well, let's dive in.
1:03 Uh, but first, I've been sharing a journey with you guys. I want to continue to share that journey. Magic mind, this stuff keeps me absolutely awake, alert. It tastes delicious. Right
1:12 now, I'm filming this thing at like 1:00 in the morning. I am wired and ready to go. I am hyped. I'm excited. I'm feeling
1:19 great. I'm able to do this because I put good ingredients in my body. These things are awesome. There's a subscription link below if you guys want
1:26 to try this stuff. Huge discount. Click the link below. Excited to share the adventure with you guys. But absolutely
1:34 love this. When you're negotiating your deals, when you're figuring out how do I find cash flow, it is a function of
1:43 becoming an insider in your market and understanding what the seller wants and understand what you need. If you go into every single deal going, okay, what do I need? What is an actual deal made of?
1:51 Well, for me, it's made of long-term cash flowing fixed rate debt. I'm going to buy a deal. It's going to cash flow day one out of the gates. It has to.
1:58 That's a rule. I'm not going to deviate on that. My income will go up permanently when I buy this deal. That means I'm raising enough money to
2:07 actually have a reserve. If I'm going in low to no money down, I have a reserve set up. I've allocated for the renovations that we need to do through this project
2:15 upfront. And it is structured in a way where it is going to pay me every month.
2:19 That is a goal for me. And I need to figure out what the seller wants and just write it down. So I need to figure out with the broker or direct with the owner, which is usually how my deals go.
2:29 Everyone in our group, we don't shotgun offers out, by the way. We're not just writing offers every day. I hate that model. One or two offers a month for
2:37 most people. We're finding deals that we actually think we have a good chance of getting accepted. We've talked to the broker or the owner. We've really mapped this out and we said, "Hey, I think I
2:45 have a solution where I get everything I want." They get everything they want.
2:47 One of my favorite books on negotiating of all time. Never Split the Difference by Chris Foss without explaining the entire book. The title Never Split the
2:56 Difference. Everyone gets 100%. It is always a win-win win-winwin win-win. I get long-term cash flowing fixed rate debt. All of my mentees get
3:04 long-term cash flowing fixed rate debt with margin, with a reserve, with your renovation budget all set up on the front end. We have to figure out what
3:12 the seller actually needs. Is it a specific price? Is it a specific interest rate? I did a deal where all they wanted to do is retire on $10,000 a
3:19 month. The property was only making $5,000 a month when they wanted to sell it. How would we pay them $10,000 a
3:27 month on a building that only makes five? The answer is we had a path to get it to make $30,000 a month. It was not there yet. We just set it so there were
3:36 no payments for the first 6 months while we fixed all of their collection problems. We came in with a mission. We came in with a budget. We came in with
3:43 the raised capital. We bought it very low down, 15% down. The rest of the money was structured with equity partners. This was one where the seller
3:51 wasn't able to finance 100% of it. They had a little bit of debt on it. We had partners come in. They wiped out that original debt. They helped fund the
3:58 initial renovation. And the only thing we had to map, the only creative piece, there's there's one takeaway here that's going to rock your world, by the way.
4:07 But the only creative piece of this thing was we said, "Hey, payments need to start 6 months from now so that we can run this property without losing
4:15 money, get paid day one to get the collections up, to get the leasing up, to finish a few renovations so that we
4:22 can pay you $10,000 a month, which is exactly what you want to retire on." We wiped out their debt. We gave them their $10,000 a month. They got the exact
4:31 price that they asked for for the property. We got income for the rest of our lives. One deal. And then, by the
4:38 way, we did another deal two weeks later, another deal two weeks later. Different structures, very similar.
4:42 Here's the one takeaway, and this is what everyone in multif family strategy is doing differently than really the rest of the country. One, we're not shotgunning offers out everywhere. We're
4:50 actually writing offers that we think can get accepted by really mapping out what do they want and what do I need and make sure that we find a way to say yes, even if it looks a little bit different.
4:59 It's yes to everything that you want. Here's what it's going to look like.
5:03 $10,000 a month, you got it. That's going to start in 6 months from now after we clear your debt right now. We're going to take over the property.
5:10 This is our game plan. This is how we're going to get you there. Notice I'm not giving to them immediately. We did a magical little
5:18 thing. We said, "What was the simplest answer to say yes to everything?" I've seen a lot of creative finance structures where people do one of two
5:25 mistakes. They either try to just absolutely hone in on one strategy and they always pitch the same strategy every single time. You might hear this
5:33 video and be like, "Oh, every time I need to pitch no payments for 6 months." That is not what I'm saying. You need to map out both sides and say, "What is the
5:40 least amount of change I can do to make sure that I get what I want they what they want?" We were off by $5,000 a
5:48 month of cash flow. So, all we did was say no payments. By the way, that $10,000 a month, we only had 4% interest on that deal. It was almost all
5:56 principal. That means when we write that check, our equity goes up and our debt goes down significantly every month. The property paid for the property, plus it
6:04 cash flowed additionally to us. This helped me retire my wife. But in addition, it gave the seller exactly what they had always dreamed of. They
6:12 got to truly retire from a property that was eating them alive. Everyone won. It was the simplest
6:19 answer. When you get too creative, one, your deal doesn't get accepted. Two, you make all sorts of mistakes. The deal doesn't look like how you wanted to.
6:27 I've gotten too creative before. Very costly to do. If you can find the simplest answer to say yes to everything
6:35 they need in a way that allows you to cash flow on long-term cash flowing fixed rate debt, you can buy infinite deals and every time you close, your
6:43 income goes up again and again and again and again and again. That's the magic. I mean, that's the secret sauce. Multi family strategy, I teach a whole lot
6:51 more than that. Well, you know, we'll teach you the analytics, the math, the strategy, the conversation pieces, how you actually structure these deals, how you write those offers, and how you
7:00 negotiate them to get them accepted. But if you distill it down to its simplest form, it is what is the least creative
7:08 creative finance method to say yes over here and yes over here. That is why cash flow is not dead. That's why every deal we purchase, cash flow is day one. And
7:16 that's why you need to copy the strategy to do the same. I hope this helped. This is multif family strategy. I'll see you on the next episode.

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