📋 A Clipboard, A Check & A Counter: How We Beat 4 Offers Before They Were Written
One group showing. Seven brokers. Zero second chances. Here’s how I helped a seasoned investor win the deal — before the others even knew we were in play.
👋 THE INVESTOR WHO DIDN’T NEED HAND-HOLDING — BUT WANTED STRATEGY
Some clients come to you with experience — real experience. I had known this client for years from my time in financial services. He wasn’t new to investing. In fact, at one point, he had over 100 units under management. Generational wealth, long-term ownership — this wasn’t a first-time homebuyer looking to test the waters.
But that didn’t mean he didn’t value smart representation. What mattered to him was efficiency, strategy, and creative thinking. He’d worked with plenty of real estate agents before — but when we reconnected, he made it clear: he wanted someone who thought outside the box, who wouldn’t waste time, and who could navigate a competitive market with confidence.
I was all in. And so was he.
🏙️ THE GOAL: ADD TO THE PORTFOLIO — FAST
He was looking for a 2- to 4-unit building, preferably in a strong rental area where value could be added. We were in a full-blown sellers’ market — inventory was moving fast, and good multifamily properties in A+ neighborhoods were rare and competitive.
So when a 3-flat hit the market in Andersonville, I knew it wouldn’t sit.
This wasn’t just a good location — it was one of the most desirable neighborhoods in Chicago, with walkability, amenities, and strong rental demand. It checked every box. The building had solid bones, but it also had room for improvement — exactly what he was after.
But there was a catch.
🕐 THE ONE-HOUR SHOWING WINDOW
I reached out to the listing agent for showing instructions. That’s when I got the news:
“There’s only one group showing. One day. One hour. That’s it.”
No second showings. No private tours. If you wanted to see the building, you had to show up during that one-hour block. And that was intentional. The listing agent was sharp — she was creating urgency, and it was working. I knew we’d be competing.
What I also knew? Most agents weren’t going to be ready.
They’d walk their clients through, say “I’ll follow up later,” and maybe submit something that night.
I had a different plan.
📦 FIRST IN, LAST OUT — AND PREPPED FOR THE MOMENT
We arrived first. I had my big red clipboard in hand, looking more like a building inspector than a buyer’s agent. But it wasn’t just holding a pen and scratch paper.
Inside that clipboard?
✅ A fully executed offer
✅ A certified earnest money check
✅ My plan to not leave without handing them both over
We walked the property slowly. Took it all in. I answered my client’s questions, pointed out value-add potential, and kept my eyes on the other brokers trickling in.
In total, seven agents came through with their buyers.
They all left the same way: with notes and intentions.
We left with an offer on the table.
✍️ THE MOVE: OFFER IN HAND — BEFORE THE LOCKBOX CLOSED
As the agent began locking up, I stayed behind.
I introduced myself again, thanked her for her time, and then pulled the contract and check out of the clipboard.
She looked surprised.
“Wait, you’re submitting right now?”
Yes. Right now.
It wasn’t even a full-price offer. But it was complete. It was serious. And it was in hand minutes after she locked the front door.
🧠 STRATEGY > SPEED > EMOTION
What most agents fail to realize in this market is that offers aren’t just about price.
They’re about efficiency. About certainty. About making the listing agent’s job easier.
I gave her everything she needed to take us seriously — fast. We didn’t need a drawn-out back-and-forth.
Later that day, they came back with a counter at full asking.
📩 THE OTHERS CAME — BUT TOO LATE
By the next morning, the listing agent had received four more offers.
Some might’ve been stronger in price.
Some might’ve been from agents with long resumes.
But the deal was already done.
We were signed, sealed, and executed. And those other agents? They never saw it coming.
🧲 THE RECRUITMENT ATTEMPT
Now here’s the twist: the listing agent wasn’t just an agent. She was the team lead of one of the highest-producing groups in the Chicagoland area — 12+ agents, massive volume, big brand presence.
She was so impressed by how I handled the deal that she tried to recruit me — hard.
I was flattered, sure. And I even agreed to talk.
But here’s the thing: energy matters.
I asked to meet the full team before making any decisions. She invited me to their weekly 6AM meeting. It was cold — not the temperature, the vibe. Competitive. Distant. Transactional.
That’s not how I work. I’m not chasing quotas. I’m building relationships.
I declined the offer. And I’ve never regretted it.
🔨 THE RENOVATION & THE ROI
My client knew exactly what to do with the building.
The first-floor 2-bed unit had access to an unfinished basement with high ceilings. He converted it into a 4-bed, 2-bath duplex-down.
The upper two units remained 3-bed, 1-bath rentals.
With smart renovations, he increased both cash flow and long-term value.
It’s still a strong-performing property in his portfolio today.
And yes — we’ve done more deals since.
💡 WHAT YOU CAN TAKE FROM THIS STORY
Speed matters. The first serious offer in hand often wins.
Presentation matters. A clean, complete, in-person offer cuts through the noise.
Tactics matter. Out-think the competition, don’t just out-spend them.
People matter. Your process is your brand — don’t sell it short.
📣 THINKING ABOUT BUYING — OR BUYING DIFFERENTLY?
Whether you’re an experienced investor or buying your first property, you need a strategy — not just an MLS search.
Let’s make a plan.
👉 Schedule a strategy call
📞 Or call/text me directly at 312.880.9409
