The Art of Retrading & 60 Days to 2026

release edition [043]

read time [5 minutes]

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Today at a Glance:

Retrading: The Art & Science
2026: 60 Days to Go
Weekly Listen: Jon Gray

Retrading

I spoke to a friend recently and he shared a deal story with me about a property that he's had under contract.

Since contracting the property, the T-3 NOI has dropped significantly and the risk profile of the investment opportunity has shifted as a result.

Knowing this, and despite his earnest money deposit being non-refundable, he elected to ask the Seller for a significant price reduction of 7-figures and ~5 of the purchase price.

Amazingly, the Seller agreed.

My biggest takeaway from the conversation was this:

Retrading a deal is both an art and a science.

The Art

As a Buyer, the better you know the Seller, the better you can solve for what's most important to them.

In my buddy's case, certainty of close and moving on from the property was most important to the Seller, so he believed that a price adjustment in the 11th hour would be uncomfortable but likely achievable.

Knowing how to appeal to the correct emotions of the Seller are critically important. Some Sellers (or their attorneys) don't like confrontation, so an aggressive approach can work to bully your way to the finish line.

But, in most cases, the fear of loss is going to be the strongest emotion that you as the Buyer can deploy against the Seller.

Does the Seller have a 1031 upleg under contract?
Does the Seller need the cash to solve other problems?
Has the property been in and out of contract with other Buyer(s) previously?

Understanding what the Seller may or may not have to lose is a critical piece of negotiating towards a win-win outcome.

The Science

Equally important, or even more so in the institutional word, is the science behind a retrade.

As a Buyer, my buddy emphasized how he quantified the drop in NOI as a justification for his price adjustment.

He added that he conveyed why the drop in NOI mattered.

In his case, it was going to negatively impact his loan proceeds, and the resulting returns of the investment opportunity for his investors.

Ultimately, he backed into a retrade dollar amount that solved for a similar return profile as when he originally put the property under contract.

Conveying and defending a quantifiable negative movement in property performance during the escrow period is a Buyer's best chance at successfully retrading the price after earnest money deposits are non-refundable.

It's difficult to retrade at the 11th hour with good data, and it's nearly impossible to do without. Know the numbers and be prepared to defend them.

In closing, I will caveat the above points by stating the following: Retrading when a price adjustment is not objectively merited is not negotiating in good faith.

You only get one reputation. Use it wisely.

2026

There are just 60 days remaining until 2026 arrives.

The visionary in me always enjoys this time of year when things slow down and I have more time to reflect on the past year & the year ahead.

I also spend time thinking about systems and goals that will make my year ahead a successful one.

This time last year I was on a 100 day mission to post daily on LinkedIn, which I carried into 2025 for a total of 200+ days of posting content.

Then, in late Spring, I burned out, and I took nearly 4 months off from publishing content outside of this newsletter.

I am beginning to reflect on 2025 as the year is winding down.

I'll share more thought as the year-end approaches, but I'm sharing these now in case they're helpful.

"Reminded More Than Taught"

Alex Hormozi said this years ago and it stuck with me, because it's true: "We need to be reminded more than we need to be taught". Doing something repetitiously over time creates the opportunity to benefit from the power of compounding.

Reminder to myself: Consistency matters more than intensity.

Expertise = Curiosity + Learning + Repetition

The smartest people are rarely the "most successful" ones. Why? Because they often over-analyze their way out of making the best asymmetric decisions (i.e. maximum upside with limited downside).

Meaning, they take an approach which is skewed towards risk mitigation rather than regret minimization.

Reminder to myself: Stay curious, keep learning, and remain consistent.

Passion Projects --> Momentum --> Breakthrough

I thrive with momentum. At work, at home, in the gym, in my side projects.

If you're feeling stuck, consider taking up a hobby or passion. This will build momentum, and that momentum will carryover into other areas of your life.

Reminder to myself: The way out of a rut or plateau is often through a new passion project. (More on this in the future).

Build or Find a Community

This is cliche, but it's cliche for a reason, because it's true.

Going "monk mode" or taking a solopreneur approach is cool, but all the best creators and entrepreneurs that I know have access to both (1) a supportive network and (2) an intimate inner circle.

I plan to lean into both in 2026 (More in this in the future, too).

Reminder to myself: If you want to go fast, go alone. If you want to go far, go together. (Cliche, I know, but again -- it's true).

Weekly Listen

This week's listen is a recent 13-minute Bloomberg interview of Jon Gray from Blackstone.

In this short interview, Jon addresses the state of the economy today, tariff concerns, inflation, labor markets, private credit, the Fed, and his near-term outlook.

You can listen to the full episode here.