Today’s Observation – July 2, 2026
Back from New York City, I can’t help but laugh at the contrast.
On one hand, you have two people climbing to the very top of the Empire State Building antenna. Then there was the usual collection of things that only seem normal in New York after you’ve lived there long enough.
But the biggest lesson I took home wasn’t from anything I saw on the streets. It came from a simple question I asked:
“What’s a financial lesson you learned the hard way?”
The responses were honest and hard-earned.
- Don’t do business with family.
- Don’t count the sale until the money is in your account.
- Don’t invest with bad syndicators.
That last one hit home.
One person shared that they lost $50,000 because they invested with a syndicator.
For those unfamiliar with the term, a real estate syndicator is someone who raises money from multiple investors to purchase and manage a real estate investment, such as an apartment complex, self-storage facility, or commercial property. Investors provide the capital, while the syndicator is responsible for finding the deal, operating the asset, and executing the business plan.
When the syndicator is experienced, disciplined, and transparent, it can work well.
When they’re not, the results can be expensive.
I’ve seen deals go sideways more than once. Sometimes it’s poor underwriting. Sometimes it’s bad management. Sometimes it’s simply someone getting in over their head.
The lesson isn’t to avoid investing. The lesson is to do your homework.
Research the sponsor. Verify their track record. Ask hard questions. Read every document. Understand exactly how the capital stack is structured and where your investment sits.
Even then, understand that investing always carries risk. You can perform extensive due diligence—even background checks—and things can still go wrong.
That’s why structure matters.
Make sure a reputable title company is involved. Make sure your interest is documented correctly, whether that’s ownership on the deed, a properly recorded lien position, membership interests, or another legally enforceable structure. Ensure everything is backed by solid contractual documentation reviewed by qualified professionals.
Never assume.
Never rely solely on a handshake or someone’s reputation.
Trust is important in business.
Verification is even more important.
-Michael Sweitzer
Author, Real Estate Investor, Husband and Father
In The Trenches Monthly
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