The Question That Unlocks the Deal
Why I Never Accept the “Problem” Without Testing It
By Jai Thompson
Introduction
I manage a private equity platform deploying 13–18 million per quarter across multiple real estate asset classes.
Our model is asset-based, escrow-directed, and execution-driven, allowing us to close in 23 days or less with certainty and clean title flow.
We acquire and operate across:
• Luxury estates
• Single-family residential portfolios
• Multifamily communities
• Hospitality and hotels
• Mixed-use properties
• RV parks and mobile home communities
• Golf resorts and destination assets
• Specialized housing and income portfolios
Capital is structured, operators are paid, reserves are built in, and all disbursements are controlled through escrow.
We deploy with discipline, transparency, and speed—while tithing back to the communities we serve.
Structure over sacrifice. Stewardship over struggle. Every deal builds legacy.
The Moment Most Investors Kill the Deal
In real estate negotiations there is a silent killer.
It happens the moment someone says:
“The bank won’t allow it.”
Most people hear that and stop thinking.
They repeat the obstacle.
They worship the obstacle.
They preserve the obstacle like it is sacred truth.
And the deal dies.
What my mentor Marco Kozlowski teaches is simple but powerful:
Never accept the problem until you test the problem.
The Psychological Trap
Here is the pattern that kills deals.
Someone states a problem
Everyone assumes it is absolute truth
No one asks the next question
Example:
Seller owes
$6,000,000
Property value
$5,500,000
Seller believes they must bring
$500,000 to closing.
The agent repeats it.
The broker repeats it.
Everyone repeats it.
And suddenly the problem becomes law.
But it might not be.
The Three Magic Questions
These questions unlock deals because they introduce curiosity instead of conflict.
Question One – The Curiosity Door
“Let me ask you something simple. If there were a clean, legal way for the seller to avoid writing that check, would that be worth exploring?”
This does three things:
• reframes the problem
• introduces possibility
• tests openness
No pitch.
No numbers.
Just curiosity.
Question Two – The Outcome Test
“What outcome would the seller prefer if the bank was satisfied?”
This shifts the conversation from
bank rules
to
seller outcomes.
Question Three – The Reality Check
“Is that actually a rule, or is that just how the bank normally handles it?”
This question often exposes assumptions.
Many “rules” are simply habits.
Why This Works
Agents often focus on the obstacle:
“The bank says no.”
But the reality is:
The bank doesn’t own the property.
The seller does.
And the seller has a problem.
Your job is to explore solutions to that problem.
How I Apply This In My Deals
Because our acquisitions are structured with an asset-based capital stack, we are always exploring alternative outcomes.
Instead of arguing with the obstacle, I ask the question that unlocks the door.
Examples include:
• structured seller payoff
• subject-to structures
• escrow-controlled disbursements
• recorded price strategies
• deferred consideration
• operational buyouts
But none of those matter until the seller says:
“Yes, I’m open to another option.”
And that happens with one question.
Roleplay Training: 10 Back-and-Forth Seller Conversation
Exchange 1
Investor
“I understand the seller believes they need to bring $500K to closing. Let me ask something simple—if there were a clean way to avoid that, would that be worth exploring?”
Agent
“Well the bank says that’s what has to happen.”
Exchange 2
Investor
“Totally fair. My question isn’t about the bank yet. I’m asking about the seller—would they prefer an option where they don’t bring that check?”
Agent
“I mean… of course they would.”
Exchange 3
Investor
“Great. Then the real question is whether we can structure something that satisfies the bank and solves the seller’s problem.”
Agent
“Possibly, but banks don’t usually do that.”
Exchange 4
Investor
“Understood. Out of curiosity—has anyone asked the bank about alternative structures yet?”
Agent
“No, not really.”
Exchange 5
Investor
“Then we might be solving a problem that hasn’t been tested yet.”
Agent
“That’s actually a good point.”
Exchange 6
Investor
“If we could structure a solution where the seller exits without bringing that $500K, would they want to see it?”
Agent
“Yes, absolutely.”
Exchange 7
Investor
“Perfect. Then the next step is simple—let’s explore what outcome the seller would prefer.”
Agent
“Okay.”
Exchange 8
Investor
“Would the seller prioritize speed, tax efficiency, or maximum recovery?”
Agent
“Probably speed.”
Exchange 9
Investor
“Good. Because our platform closes in about 23 days through escrow-directed structures.”
Agent
“That could definitely interest them.”
Exchange 10
Investor
“Great. Let’s schedule a quick conversation with the seller so we can explore solutions together.”
Email Script Using The Magic Questions
Subject: Quick question about the seller’s outcome
Hi [Agent Name],
I understand the seller believes they may need to bring funds to closing.
Quick question.
If there were a clean, legal structure that allowed the seller to exit without writing that check, would that be worth exploring?
Our acquisitions are asset-based and escrow-directed, which allows us to close quickly while solving complex seller situations.
If the seller is open to options, I’d be happy to walk through a few possibilities.
Best regards,
Jai Thompson
Text Message Version
Hi [Name], quick question.
If there were a clean way for the seller to avoid bringing that $500K to closing, would they be open to exploring it?
Just trying to understand the outcome they would prefer.
The Real Lesson
The biggest mistake investors make is believing the obstacle without testing it.
Most deals don’t die because of numbers.
They die because curiosity disappears.
Solutions appear when someone asks the next question.
And often that question is simple.
“If there were a clean way to solve this… would you want to see it?”
That one question has opened more doors in my career than any pitch.
Because curiosity unlocks possibility.
And possibility creates deals.
Structure over sacrifice.
Stewardship over struggle.
Every deal builds legacy.