Your STUPID questions are KEEPING you POOR!

Christian Osgood shows how asking better questions in broker calls and owner meetings unlocks multifamily deals. Novice questions like "Are you open to seller financing?" signal inexperience and kill opportunities. Instead, use scripted frameworks that move from open-ended talk to the bank's view of the deal, surfacing maintenance issues and creative financing options without revealing weak capital.
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In real estate and in life in general, the quality of your outcomes will be dictated by the quality of the questions that you ask. If you want a better answer, ask a better question. We're going to talk about conversations that we have with brokers and with owners, what everyone is doing wrong, what you're probably doing wrong if you have less than several hundred units for financial freedom in real estate, and how you can ask some better key questions to people to get the outcomes that you are looking for. Now, if you are new to the channel, first of all, welcome. My name is Christian Osgood. I bought hundreds of rental properties starting with $0 because $0 was the budget. So with a $0 budget, I had to learn learn how to acquire rentals, how to move forward with relationships and use capital that I did not yet have to buy deals that I did not yet own. I'm going to show you some of the best tips and tricks that I have learned through the course of this adventure. First of all, let's start with the broker side. Then we're going to dive into the questions that we ask owners. By the way, I'm going to give you one of the secrets right now. You treat every owner like an owner, not a seller. There's a lot of the questions here, some of the questions that I hear that are totally wrong to brokers and to owners. Hey, uh, what are we thinking about financing? Are you open to carrying a contract? Are you open to seller financing? Are you open to selling your property? These are all questions that are newbie questions. Pros don't ask these. If you want to look like a pro, ask better questions. I'm going to show you how. First of all, with brokers, you're going to start with a normal conversation. I actually have a broker script on Multifamily Strategy. You can go to multifamilystrategy.com, check out our mentorship group. We have a full build out for this, but I'll give you the cliff notes. Open-ended questions, not something stupid like the weather or sports team. You're gonna talk about the deal. You're gonna call it an active deal. Hey, what do you think about this specific neighborhood? I love this market. Tell me what you think about this specific area of this specific town. Let them start getting into their flow. Their job is to get comfortable and to start selling. So let them do their thing. Ask 'em some basic narrower questions as you get through the conversation, such as, I see it's been on the market for a little while. Has there been a consistent hangup? What's your least favorite thing about this property? I see a lot of great things here. What's your least favorite? Get them talking, get them selling. They're salespeople. You're gonna get them comfortable. But ultimately, there's one question that I really love, and this is a simple question that asks a lot of questions. If I'm a broker, which by the way, I was a broker for years, you reach out to me, hey, how was the maintenance on the building? It's pretty good. Okay, how are the financials? Can I see all the financials on this? How soon can you get me books? These are annoying questions, and if you start asking me all these questions, I already know that I'm not dealing with a sophisticated investor. Here's a better way to ask all your questions in one. Love the deal, love the area. I'm really liking this. This is exactly the type of stuff I want to buy. Okay, what's the question I'm going to ask? How is the bank going to look at this deal? Now, why is this question so great? One, if there's a lot of deferred maintenance, the bank is going to want more down or might have a problem with financing. I'm asking about deferred maintenance without asking about deferred maintenance. If there's a problem in the books or there are financials that I need to be aware of, I need to know that to know how the bank is going to look at it. If they tell me, oh, the bank's probably gonna want 50% down, hmm, red flag. Why do they want so much down? I need to know these things. And this question is a professional question that asks a lot of things about deferred maintenance, about financial viability, and gives you a perfect segue into creative finance without asking for it. That is the main thing. If you can get through all the questions efficiently, they know that they're working with a pro. Basic question. Now, if they give you some higher down payment or they give you something, it's like, awesome. Now, is bank the way to take this out? Are they interested in carrying a contract or other terms? Is that on the table? Are we just looking at bank? It is an easy transition after they've already talked to you about the financials. If you jump the gun and you ask a question like, hey, are they open to carrying a contract on this? Are they open to seller financing? Basically, you're announcing to the broker, hey, I don't have any money. I'm not qualified to buy this deal. They're going to lose interest. Keep them engaged. The psychology of the call is open-ended. Then a little bit narrower. Then we get into financials. You're closing. You're going through a closing cycle psychologically. They're like, okay, who is this person? Here's what they're calling about. Now we're comfortable. Now I'm selling them. Now they're responding. Now we're into financials. You're walking them through a flow that makes you a ready, able, and willing buyer. Ask about the bank without telling them, hey, I don't have money for this deal right now because that's not relevant yet. You are moving yourself in their mind to ready, able, and willing buyer. Once you get to the close, there's a lot of things you can do to close the deal and a lot of different ways you can close the deal. But you're laying out the goalpost here. Do not jump the gun and don't ask a stupid question. That's one of my favorite questions. It really asks a lot in one. It gives you a lot of different places to pivot out of. Ask better questions. Now, the big one for me has been the questions that you ask a seller. When you are in an owner meeting, because they're owners, not sellers. When you're in an owner meeting, you're talking to someone who owns a property that you may one day want to own or properties like it. You want to come in and learn from them, but if you ask a bunch of dumb questions, they're not going to be really engaged. Here are the main ones that have gotten me the most traction. First of all, I want to set the stage. You need to start with some relatable point. What is it that you're actually trying to do? You're going to set a verbal agenda on this meeting. So you'll say, hey, thank you for meeting with me. I appreciate it. I want to learn how you built this business. For me, the conversation was I've bought 2 duplexes already, so I'm a fellow owner in their market. I bought a couple duplexes already. I'm realizing one duplex at a time is not going to help me retire my wife in the time that I want to retire her. I've seen you buy bigger buildings. I have not yet figured out how to do this. This is why I wanted to meet with you. I wanted to learn how you got to that. Now, a lot of owners from that point, not all of them, but a lot of them would say something to the effect of, hey, you learned this earlier than I do. I started small and it took me years and years to scale up, but you're right. To hit your goal, you're going to need to buy bigger. You then let them just tell their story. The questions that you're going to be asking are going to be tactical questions. Why did you do this specific step? Is that a necessary step? You ask through them. Great example. I was in a truck with a guy named Gary. We're driving around and he's like, on this deal, it was my first duplex. I hadn't bought multifamily yet. I didn't have a lot of cash on me. I had a buddy named Dan who also didn't have a lot of cash on him, but together we could take out this property. We partnered and we bought the property together. Good question. Awesome. That sounded like a good way to move forward. Would you recommend looking for partners that early in the game, or have you learned a better way to play the game? For him, he really liked partnering. In fact, he had lots of partners. He talked about different partnership structures. But ask just basic intelligent questions. Do not in the middle go, hey, are you open to selling that duplex? Or how would I buy something like that? Not relevant yet. Ask questions about the things that they're talking about. Ultimately, as they get through their story and you learn how they built their business, ask for best practices. Not how to buy them, but best practices in running the portfolio. If you want tactical advice and you want a chance at buying a property, ask this question at the end. This is a golden question. Given our conversation, what would you recommend my next step would be, given what you did and where I'm trying to go? Here's why this is a great question. It makes them think back to that goal you communicated at the beginning of the conversation. Now, in movies, we call this the anchor. If you've ever seen, like, Wolf of Wall Street's a good example. They have Matthew McConaughey at the beginning do his little, uh, thing. They anchor that so when he does it later in the movie, you think back to the beginning of the movie, you have emotional tie to it, and it gives a cohesive story. You have to remember back to the beginning. When you set an anchor like this on a conversation point where you communicated a goal, you spent the whole time letting them talk and listening to them, and you ask them, well, given where I'm trying to go, what would the next practical step be? Now they have to remember back to the beginning of the conversation. At the end of your conversation, remember your goal, and that is going to lock it in their mind. Now you are always the person, like In my case, I am always the person who is trying to buy slightly larger deals than I am right now in order to retire my wife from teaching in a faster timeline. When a deal comes up in their network and owners know other owners, when someone goes in their market to sell something and it is the wrong deal for them, they're going to be reaching out to me because we have anchored that in their mind. We have learned from them. They know, like, and trust us, and we can move forward. When I'm talking about quality questions though, I'm talking about throwing out stuff like, Are you open to selling? Have you seller financed before? Hi, I'm new to real estate. Can I learn from you? Like, give some thought in this. This is a piece of advice that an early mentor gave me, and I use this all the time. I've practiced this script again and again and again, not because I like scripts. I was a salesperson for 8 years, hate scripts. But a great actor, like great Hollywood actors, memorize the script so well that they can comfortably go off script and they'll go right back into the flow. They understand the spirit of what they're doing. That is how I practice. Put together your talk track, understand the points of the conversation you're trying to hit so that you can spend your time listening because you already know where you're trying to go. You can comfortably get back to your talking points because you practice them so much. This is not a robotic thing. This is not a, hey, when I read this script, I'll make a bunch of money. It's a practice your talking points, understand the flow of the conversation so well that you can have it organically. Practice great questions. I actually take the time to write them out. Think through what you actually want out of your meetings and out of your conversations with brokers and owners. Script them out and then listen to the questions you're asking. If any of them sound like dumb questions, think of a better way to ask them. But I promise you, if you're feeling stuck in your broker calls, you're getting stuck in your owner meetings, you're not finding opportunities like you feel like other people around you are. I've done multifamily strategy for years now. I've taught hundreds and hundreds and hundreds of people. How to buy real estate through multifamily strategy. That is the number one thing almost every single time when someone calls and says, hey, I've been stuck. I've been going through the course. I've been talking on the mentorship and doing everything and I'm not getting traction. It always comes back to the way the questions are being asked or the questions that they're choosing to ask when they get in front of other people. If you can learn this one skill, if there's nothing else you do in real estate, you will move farther than 99.99% of people. I absolutely believe this. I promise you this is the skill Learn to confidently flow through a conversation, ask great questions, and be an amazing listener. You will learn more, buy more, ultimately make more in this business if you master the skill. One additional bonus to this: other people in your market will enjoy working with you. You will have more fun playing this game on top of having more success if you master this one skill. Told a lot of people this. I don't know that I've shared it enough on YouTube. So if you're watching this video, You're getting the good stuff. This is from years and years of teaching this. This is where almost everyone gets stuck, including myself. I started with stupid questions. You keep going and going, you get a little bit better. Watch channels like mine, watch other channels, subscribe now if you want more content like this, but get around people who are doing the thing that you want to do and you're going to move farther. This is the advice that I would give anyone starting or who's feeling stuck in real estate. Ask better freaking questions. Hope you enjoyed this. Like and subscribe for more. I'll see you guys all in the next episode.
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