Chapter 8: Overcoming Common Objections
“Life shrinks or expands in proportion to one’s courage.” - Anais Nin
“I would never sell my property subject to.”
If I had a dime for every time I heard that line, I’d have enough cash to stop chasing deals altogether. And yet—here I am. Because for every person who shuts the door on creative financing, there’s someone else willing to have the conversation. And that’s all you need.
So, if you’re worried there aren’t enough opportunities out there, trust me—there are. The key isn’t luck. It’s persistence, skill, and mindset.
Early on, objections used to frustrate me. Now? I welcome them.
Objections aren’t roadblocks. They’re invitations to negotiate. When someone pushes back, it’s like flipping on a neon sign that says, Game on!
If you’re not already comfortable with negotiation, don’t stress—we’ll go deeper into that in the next chapter. But here’s the truth: the best way to get good at this is through experience. You’ll make mistakes. I sure did. I’ve spoken too soon, given away too much, even negotiated against myself before the other person had a chance.
But here’s the secret: it gets easier.
If you want to accelerate the learning curve, read Never Split the Difference by Chris Voss. It’s one of the best books on negotiation. But more important than any book is this: keep showing up, keep practicing, and don’t let objections intimidate you. They’re not a no—they’re just the beginning of the conversation.
Case Study
“Your Goal is to Help the Seller” by Henry Washington
Overcoming objections is key to landing great real estate deals. The most important thing to remember is this: your goal is to figure out how to help the seller.
Most investors focus only on their own best interests. The best investors understand that when you work in the seller’s best interest, you can create a deal that is both profitable and sustainable.
One deal that really tested my ability to overcome objections involved a seller we’ll call “Bill.”
I found Bill through a direct mail campaign in a specific neighborhood I was targeting. He responded to my letter and asked me to make an offer. Bill told me he was retiring from being a landlord and wanted to sell his property to help support his adult children.
The house was in decent shape—just a little dated, but completely livable. He had long-term tenants who had been there for years. The after-repair value (ARV) was around $250,000, but given the minimal work needed, I knew I couldn’t pay more than $150,000 for it to be a profitable deal. I started negotiations at $120,000.
When I presented my offer, I could see hesitation on Bill’s face. When I asked what he thought, he said, “It’s in the ballpark.”
Then came the five words that kill most deals: “Let me think about it.”
When a seller says that, it usually means your offer doesn’t fully meet their needs. Most investors assume the problem is price. Often, it isn’t.
So instead of pushing back, I slowed down.
“That’s totally understandable,” I said. “It’s a big decision. Do you mind sharing your biggest concern?”
“I’m just looking for a little more money,” Bill replied.
I followed up, “I completely understand that. What number would make sense for you?”
Without hesitation, he said, “$200,000.”
Now, we had already established that I couldn’t go above $150,000. But instead of countering immediately, I wanted to uncover what else might be holding him back.
“I don’t think I can get to that number,” I said, “but if I could get close, could we do a deal today?”
That’s when he shared something important.
“Well,” he said, “I really want my tenants to stay for at least a year. They’re older, they’ve lived there for years, and they treat the house like their own.”
Now we were getting somewhere.
That was something I could work with. I told Bill I’d be happy to let them stay for at least a year—as long as their rent covered my mortgage and expenses. He explained they were already expecting a rent increase and could pay $1,500 per month.
With that in mind, I bumped my offer up to $130,000.
Still not enough.
Bill came down a bit but was still asking for more than I was comfortable with—$170,000.
At that point, I knew we had to get creative.
“It seems like we’re still too far apart on price,” I said, “but I think I might have a way to get closer to your number. Do you have a mortgage on the property?”
“No,” Bill said.
“Great,” I said. “What if I could find a way to pay you more money, let you keep your monthly cash flow, and allow your tenants to stay?”
That got his attention.
I proposed buying the house on terms. (I never say “owner financing” to a seller—it can sound intimidating.) Bill asked what that would look like.
“Since you own the house outright,” I explained, “I could buy the property for $150,000. Instead of making my payments to the bank, I’d make them directly to you. That way, you’d keep your monthly income, and I could pay more while keeping the tenants in place.”
Bill liked the idea—but he had one final objection.
“I’m selling because I need some cash to help my daughter pay off medical debt.”
I asked how much he needed, and he told me, “$15,000,” he said.
That gave me my answer.
“What if I give you $15,000 as a down payment at closing,” I said, “and then I pay you $750 per month for the rest?”
Bill called his accountant to confirm the tax implications. Then he agreed!
Did you notice I never asked about interest rates?
That’s because Bill’s biggest concerns weren’t interest. They were taking care of his tenants, getting cash for his daughter, and maintaining some monthly income. If interest had mattered to him, he would have brought it up.
So I structured the deal around what actually mattered to both of us.
Here’s how it broke down:
Purchase Price: $150,000
Down Payment: $15,000
Seller Financing Balance: $135,000
Terms:15-year amortization at 0 percent interest
Monthly Payment: $750.57
This was a true win-win deal.
Bill got the cash flow he wanted, his tenants stayed in place, and he had money to help his daughter. Meanwhile, I acquired a great asset under market value with zero interest—and my rental income more than covered the mortgage while still allowing me to cash flow.
The key takeaway?
Objections aren’t deal-killers—they’re signals that a seller’s needs haven’t been fully met yet.
The best investors don’t just push for a lower price. They ask better questions. They listen for what really matters to the seller. And they structure deals that create wins for everyone involved. If you do that consistently, you’ll close more deals—and build a stronger real estate business.
Find out more about Henry, author of “Real Estate Deal Maker,” on Instagram @thehenrywashington.
