I Lost $32,000 on One Deal

[Jeremy Beland]

After almost a decade in this business, I just took my biggest loss.

$32,000 gone.

Not a small margin. Not a break-even. A straight loss.

And yeah—it stings.

Here’s what made it worse:

• We bought the property at a good price

• Only needed light updates

• Priced it below market

• HOA fees were reasonable

• It came with lake rights in a desirable New Hampshire area

But it sat.

Turns out, no short-term or long-term rentals were allowed.
We didn’t think that would matter. It did.
Homeowners weren’t buying. Investors couldn’t rent.
One buyer backed out.
Months passed.
Eventually, it sold—but not without the hit.

This isn’t a post about blame.
It’s just a reminder that this happens—even when the numbers look right.

Sometimes you get burned.

Even with experience.
Even with systems.
Even with almost 500 deals behind you.

Losing money isn’t the lesson.
The lesson is: this is part of the work.
Mistakes come with it.
So do tough calls and unexpected outcomes.

Some losses don’t come with a deep takeaway.
You just take them and move forward.

What matters is staying in it.
Doing the next deal.
Not letting one loss turn into hesitation.

If you’ve ever taken a hit, you’re not alone.
We all have.
That’s the truth most people don’t talk about.

Got a lesson from a deal that went sideways?
Share it below—I want to hear it.