Mastering Tough Calls in Real Estate Wholesaling

In this training video, Nathan Payne conducts a live role‑play call with real‑estate agent Greg Cullison and later with a simulated seller, illustrating how to handle difficult wholesaling conversations. Nathan, an out‑of‑state wholesaler, seeks market insight for a Baltimore townhome he wants to purchase off‑market for $120,000 while comparable listings are $160,000–$250,000. He navigates the agent’s skepticism, explains the wholesaler’s value proposition (speed, convenience, reduced commissions), and probes price volatility. The call shifts to a mock seller where Nathan tests pricing assumptions, presents commission calculations, and incrementally raises his offer from $47,550 to a maximum of $82,000 based on ARV and rehab costs. Throughout, he demonstrates objection handling, relationship‑building tactics, and decision‑making frameworks for when a seller might list versus sell to a wholesaler. The session ends with a debrief where Nathan and his team evaluate his performance, emphasizing professionalism, transparency, and strategic negotiation.
Chapters
I just wanted some, like, the opinion of an expert in the market. I market, like, off-market. I, like, send out mailers and texts to people in the area. I'm from Utah, but I do market and try to get deals in Maryland. But this area is interesting where you have a listing, and I have one that's, like, a couple streets over, and I'm just seeing, like, a really big price range on these townhomes. So I'm kind of nervous to, you know, pay about $120,000 for a house that's off-market when I see some houses are selling for, like, $160,000.
Well, you're from Utah.
Yeah, I am.
Yeah. So you don't know the area that well.
Exactly. That's why I'm calling you, because you're a wholesaler. Exactly. Yeah, I actually do both. I buy and fix and I wholesale.
Yeah, sure.
Hello?
Hello, this is Greg Cullison. I was on the other line. You were calling me?
Yeah, Greg, I'm sorry about that. Do you have a couple of minutes to talk? I was just calling about your Green Hill Avenue property. In Baltimore.
Yeah, I can talk to you about it. Corey is the main person on that, but I'm happy to talk to you about it.
Okay. Well, you know, the reason I'm calling is I just wanted some, like, the opinion of an expert in the market. I, um, I market like off-market. I like send out mailers and texts to people in the area. And I'm from Utah, but I do market and try to get deals in Maryland. But this area is interesting where you have a listing, and I have one that's like a couple streets over, and I'm just seeing like a really big price range on these townhomes. So I'm kind of nervous to, you know, pay like one, about $120,000 for a house that's off market when I see some houses are selling for like $160,000.
Well, you're from Utah.
Yeah, I am.
Yeah. So you don't know the area that well.
Exactly. That's why I'm calling you because you're a wholesaler. Yeah, exactly. Yeah, I actually do both. I buy and fix and I wholesale.
Yeah, sure. Okay, well, there's a vast difference of condition, like there is, right? Of course, real estate. But, um, yeah, if you were in them each and every day, you would see that.
Yeah. And I'm sorry, I mean, I don't mean to like waste your time, offend you. It sounds like maybe you've talked to wholesalers before that wasted your time.
I have. Yeah. And I really don't have a high opinion of them.
Yeah, I get that. You know, I totally understand. Like, I mean, there are some shady ones. And I'm sure you guys don't think highly of us because, you know, sellers make more money if they list it, right?
14% more national average.
Exactly. Yeah. And I totally get that. And I tell— actually, when I talk to sellers, I tell them, I'm like, hey, you should list this. I only— the only benefit that I provide to you is like convenience, ease, and speed. But if you don't want, you know, to sell it in 7 days, you need to list this. So that's how I kind of approach it. And making relationships with agents like you, I think we can, you know, work together instead of just be like, you know, wasting each other's time, you know.
I sell a lot of houses. I really don't need to make any alliances with wholesalers.
Okay. No, I totally get that. But I guess, can I ask you one thing? Is it true that in this specific area where you have the townhomes, are the prices like, do they fluctuate a lot or is it pretty standard for like a 3-1 to be around $250,000 when it's sold, when it's fixed up?
It better be looking awesome for that.
Well, that's—
Better be the nicest, nicest one around.
Well, I appreciate that advice. And again, I'm sorry for, you know, wasting your time. I didn't I didn't mean to, you know.
Have a good day.
You too.
All right.
My man in Baltimore out there, they don't— that guy was not a fan. And, uh, but hey, how do you think I handled that, AJ? Do you think I was all right?
I think you were very professional, actually.
Look, there's agents that don't like wholesalers. That's okay. I never have forced anyone to do a deal with me, ever, period. I always tell them what they— what their options are. I go to sleep every night feeling great because I say, hey, look, you know, if you sell this to me, I got to make money, right? You're going to be selling this to me less than if you listed it. And they say, I get that. I get that. Let's— I don't care. I just want this done. I don't care. Do you guys see how I handled that call? I ain't nervous. I ain't worried. Like, dude, you don't like me.
That's fine.
You don't know who I am. You don't know what I do. And you don't want to make an alliance with one of the top wholesalers in the world? You just lost out, buddy. Right, AJ?
Right, right.
Yeah.
Bump that guy. I'm just kidding. He's cool. Hey, I get it. There's probably some wholesalers that have just called him and wasted his time. Don't worry, guys. That's what happens. And I'm actually glad that we had a call like that. What did he tell me in his grimacing tone and just like his— that he didn't like? He said, if you wanted to sell it for $250,000, this thing better be the best thing in the neighborhood. Right? So $250,000 is not, according to one guy, and I can call more. So $250,000 is not going to work. It's probably going to be like $166,000. And that reason I'm saying $166,000 is I'm looking at one of his that he has. He says you're a wholesaler from Utah. So yeah, man, I am. What you gonna do about it? All right, so this is one of his. It's a 3.5. This is an actual comp, okay? This is what's currently for sale, and he's upset because no one wants to buy his at $165,000. Okay, so it looks like, AJ, I think we might have to put this thing at $160,000. And now we're talking on the phone and you want $120,000. It ain't going to happen. I'm losing money. So where is it going to make sense for me to buy this now that we know that the ARV is $160,000? I think originally my boy Tony was saying $75,000. That— it's getting kind of tight at $75,000. Tony, I'd say if you can offer them $47,550, it's a for sure deal. You know, you should, you should go lower than $75,000. And if you're, if you're feeling crazy, if you're feeling like, you know, you want to give— if you want to make an alliance with this jabroni, then you could call him and he might be able to list it for you. You might be able to list it with— what's this guy's name? Greg. Freaking Greg. Thank you, Tracy. Tracy said I did a very good impression of Greg. Everybody, let's call Greg right now and just be like, hey, yeah, I'm a wholesaler. Let's light him up. Hey, Greg, I heard you love working with wholesalers. All right, AJ, so Tony, we ran your numbers on your deal. I would call you back. This is our conversation. We'd call back.
All right.
Hello, ma'am. I'm calling you back. Just got done talking to my underwriter. Do you have some time to talk?
Mm-hmm.
You know, I'm— I feel terrible. I was looking at the wrong comp the whole time when I thought these houses were $250,000. I just got off the phone with an agent that has a listing that is not selling. His name is Greg. If you ever want to talk to him, you should call him. I can give you his number, but he has a house right now listed for $160,000 that's really nice, updated, and it's not selling right now. That makes me worried that if I buy yours for $120,000, I'm going to be underwater. I can send you this link too, so you can look at it. So unfortunately, after talking to my underwriter and getting this knowledge, I'm going to have to be at $47,550, but I can close in 7 days. Would that work for you?
I'd have to say no to that now.
Well, Originally you were at $300,000, then you were considering $120,000. But now with the information that I've given you, what is realistic for you knowing that new houses in this area are only selling for $160,000? They're not even selling, they're listed and they're just sitting there. What are you looking for now that you know that?
I'd probably really go for at least $100,000.
Yeah. So let me tell you this. If you list this house with a real estate agent, they pay— you got to pay 3% to the listing agent, 3% commission to the buyer. You know that, right? You got to pay to list the house.
Yeah, they do.
So looking at the math, if you can't sell this thing for $160,000 because it needs to be updated, so let's say as is you can sell this thing, what would you say? As is, maybe $120,000? Would you say that's fair, ma'am?
Yeah, I'd have to say $120,000 is okay.
Okay, so if you take away the commissions, the fees, the closing costs, you're— and that's about 8%— you'd get $110,000. So yes, you would, you would make way more money if you listed it, but you told me you weren't interested in that, right?
I might actually consider it now.
I think you should consider it because, you know, looking at my numbers, if this house is worth $160,000, I mean, from what you're telling me, if it only needs a basic light rehab, let me just fudge with the numbers really quick. So this is, uh, and what, what were you saying, $100,000?
Yeah, I'll probably go for the $100,000.
Okay, so, um, that's what you're wanting. So if I had to do about a basic rehab And let's see, I might have to change this, the wholesaling fee. Yeah, it's still not going to make sense for me. I'm, you know, I feel, I feel terrible, but I know I said one, I said $47,000, but the highest, the very highest I could do. And by the way, guys, this, this is a role play. It would usually incremental raises. I wouldn't jump up this high, but I'd say, look, I'm looking at the numbers. This is the best I could do. I could do probably could do $82,000 if it only needs a basic rehab. But I guess I'll find that out during my due diligence period.
Yeah, $82,000. $82,000.
That's right.
We can get it in 30 days.
I can do it sooner than 30 days. I probably can do it maybe in maybe 2 weeks.
I'll probably, if you could give me time to think about it.
So you're not sold. Yeah, you're just not 100% sure. I know when people say that, it's usually a no. It's a no. Let's just be honest. You're not, you're not going to do it. So let's talk about what other options you're considering because you're saying no to $82,000. So if you can't get $100,000, for example, maybe you talk to 10 other people like me, what are you going to do?
Not quite sure yet.
Well, I mean, we already talked about flipping is not an option, right?
Yeah.
Keeping it's not an option. So listing it, you said, hey, listing it might be an option now. Okay. So list— is that kind of teetering right now between getting more money and listing and waiting or cash?
Yeah, you're right. Actually listing it would probably be the best.
Okay. Well, I got a great guy named Greg. I can send you his info. We partner all the time. We formed a strong alliance and we're going to work together. So I will send you his info after I talk to him and we'll see. He says he sells a lot of homes, but we'll see if he denies one that I can give him. Okay. All right. So anyway, that's, that's how it ends. She is not that motivated to move quickly, right? If she's like, I can wait, I can't force her to take the price that needs to be done. Guys, this is what I'm trying to tell you. You have to take people through the sales process. So you can determine if there's enough motivation to help someone that's in a sticky situation. If there's no motivation, they're just going to list it and they should. Everyone should list it if they have time. There's no reason to sell for cash unless you need the money fast. That's why it's there for. You need fast, quick convenience, ease, speed. That's why you do it. That's why we exist. We help everybody that I've ever done a wholesale deal with. I provided value by being quick. And that's what I'm trying to show you guys is follow the sales process. If you want to negotiate a good deal, there has to be some underlying motivation that's causing them. Use agents to help you determine the value. I use them all the time, and I get on calls with people like that, and you can see, you know, it goes good or bad. But who cares? Don't you ever think that you're not doing something right. Maybe some of you are doing something like shady, like maybe you are. I'm not. I tell people all their options and I say, this is what you can do, you decide. Okay, there's nothing shady about giving people all the truth, everything they need to know, and then being a consultant. Okay, so when that guy came at me, Didn't even shake me. Shouldn't shake you because as a wholesaler, you're doing a service. We help so many people find properties to flip. We help people, so many people get properties that need to be sold quickly. We help them. Okay, that's how you got to look at it.
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