Contracts, Deadlines, and Accountability: Lessons from a Flip

Contracts, Deadlines, and Accountability: Lessons from a Flip

It's early September. We’d just finished renovating a property in North Carolina, and it looked amazing—every detail carefully planned, every corner spotless. We listed it on the market, confident it wouldn’t take long to sell. And we were right. Two weeks in, we received an offer: full asking price, $2,000 in due diligence money (Non refundable), a conventional loan (the good kind), and a closing date set for the end of October. Perfect, right?

I was happy. I called my investors to congratulate the accepted offer. I reminded them (and myself) to save the real celebration for when the funds hit our bank account.

and boy I was right.


The First Red Flag

The offer required the $2,000 due diligence payment within two days of signing the contract. Easy enough. I waited, and nothing came. I asked my agent to follow up, and the buyer's agent reassured us that it was on the way. Days passed, then weeks. Every day, I asked the same question: “Has the due diligence payment arrived?”

Still nothing.

Eventually, we learned that the buyer was struggling financially. She had applied for a 0% down payment loan—a new program offered by the state. A great opportunity for her, but not without its challenges.

The deposit did arrive—late and in two partial payments. I should have terminated the contract then and there. But I didn’t.


By mid-October, we were trying to get the appraisal scheduled. If you’ve ever dealt with lenders and appraisers, you know how tricky that timeline can be. It became clear that the buyer’s finances weren’t just tight—they were precarious. Deadlines came and went. Still, I held on.

Fast forward to November: no appraisal, no clear answers, and Thanksgiving approaching. At this point I felt like anyone who’s worked in U.S. real estate knows what happens after Thanksgiving—nothing. The holiday season is like a black hole for deals. If it doesn’t happen before then, it’s as good as delayed until the New Year.

Yet I kept hoping.


December arrived, and I was assured the closing would happen during the first week of the month. Monday came and went—nothing. By Friday, we finally got an update: "We’ve received all the papers. Closing will be next Wednesday."

Relieved, I told my investors, "After all the delays, we now have official confirmation—closing is set for next Wednesday."

The new week began, and with it, a new email. It was Monday, December 9th. (Yes, we made it this far).

The lender wrote:

Good morning,

Once all required documents are received and reviewed, we can submit to underwriting. Closing can occur 9 business days after the date the application is submitted to underwriting. Therefore, a closing date this week is not a possibility.

Which is, essentially in American English. means closing wouldn’t happen until January 2025.

That was it. I couldn’t wait any longer. My partner, on the other hand, hesitated. He had second thoughts, suggesting we talk to the buyer first—maybe give them another chance, you know, try to work something out before pulling the plug. But I knew we had reached the end of the road, and I made the call to terminate the deal.


The Lessons

  1. Contracts Are There For a Reason
    A contract is the backbone of the deal. When the buyer failed to meet the due diligence deadline, I should have acted immediately. By allowing the timeline to stretch, without any agreed addendum, I compromised the very structure that’s meant to protect both parties. It's not a "deal" if one side don't do his part.
  2. Deals Are Built on Small Steps
    There are many small commitments—deadlines, deposits, documents, in every transaction. How can a buyer who struggles to meet the small requirements early on deliver when the process demands more?
  3. Time Is a Currency
    The longer you spend waiting for someone to get their act together, the less time you have to pursue better opportunities. As much as we want to see every deal succeed, we must prioritize our own momentum and energy. Sometimes, walking away from a slow-moving deal is the fastest way to move forward.
  4. The Buyer’s Agent Matters More Than You Think
    As a seller, choosing the right listing agent is critical—but I Shouldn't underestimate the role of the buyer’s agent in the deal. Many buyers aren’t savvy when it comes to navigating documents, loan applications, or deadlines. The buyer’s agent is often their only guide through the process. A committed, experienced buyer’s agent can be the difference between a smooth closing and a chaotic failure.

To every investor out there: if someone can’t honor the small steps, don’t wait for them to deliver on the big ones.