We Lost $43,000 on This Deal — And It Still Felt Like a Win
Last week we finally closed a deal that had begun to feel like it would never end.
For a long time it felt like an endless money pit—draining cash, time, and mental energy. When we closed, we walked away with a check for just under $14,000. On paper, though, we lost about $43,000 on the deal.
Oddly enough, it still felt like a win.
Not because the numbers were good. They weren’t. But because closing the deal meant the weight of it was finally off our plate. No more monthly mortgage payments on an empty house. No more utilities and lawn care. No more 4–5 hour round-trip drives to do work on it. No more wondering how we were going to exit the deal without sinking even more money into it.
Sometimes the biggest win is simply ending the problem.
How the Deal Started
We bought the property subject-to the existing mortgage. The comps looked good at 180-200k and we thought there was a solid path to reselling it. Our cost was 142k. Our plan was to sell it on owner financing to a handyman buyer. All we would need to do is some clean up of the house and yard.
But almost immediately we ran into our first obstacle: the tenants.
They were not paying rent, so the first step was eviction. That process took about two months. During that time we were paying the mortgage while the legal process worked its way through the system. Fortunately, the eviction itself only cost a couple hundred dollars.
Once the tenants were out, we did some cleanup and light repairs. There was a house full of trash and even a broken down above-ground pool that had to be hauled away. We hired a couple of people locally to help clear things out and handle some minor work. All told, the cleanup and repairs were roughly $1,000–$1,500.
Not terrible. The real problem came afterward.
The Long Middle
After the property was cleaned up, the plan was to sell it. That’s where things started to stall.
The house was in a very rural area. That made the buyer pool small. It also landed in a strange middle ground: it needed just enough work that it wasn’t attractive to most retail buyers, but there also wasn’t enough margin left for most flippers. Our ideal buyer was someone who wanted owner financing and didn’t mind doing some repairs. But that buyer never materialized.
And while we waited, the clock kept ticking.
The mortgage payment was roughly $852 per month, and we ended up holding the property for 22 months. That alone added up to $18,744 in mortgage payments. Electricity ran about $60 per month, totaling about $1,320 over the life of the deal. We had to keep the lawn mowed, which cost $150 per mowing for five visits.
And then there was the travel. The house was about two to two-and-a-half hours away, so every time we needed to work on it, it turned into a full trip. My brother and I went down multiple times to do repairs and upgrades ourselves. Over those 22 months, I probably made that trip around ten times. Sometimes I stayed in motels. Sometimes it was a long day trip. Either way, it meant time away from working on the business itself.
There’s also a cost to that—opportunity cost. When you’re fixing drywall or installing trim, you’re not marketing for deals, talking to sellers, or structuring new opportunities.
The Final Numbers
By the time everything was added together, the totals looked like this:
- Purchase and acquisition costs: ~$142,000
- Ongoing holding costs over 22 months: ~$25,000
- Closing costs at sale: ~$4,200
- Total investment: ~$171,500
- Sale price: $128,000
- Net loss: ~$43,000
Not a small number. But interestingly, we still walked away from closing with about $14,000 in cash because of the equity position we had in the property. So while the overall project lost money, we did at least recover some capital and redeploy it into the business.
Why It Still Felt Like a Win
There were four big reasons closing this deal felt like a relief.
The holding costs stopped. That property had been draining about $1,000 per month between the mortgage and utilities. Once it sold, that leak in the bucket was immediately plugged.
We got liquidity back into the business. The $14,000 check wasn’t profit, but it was capital we could immediately put toward better opportunities.
No more travel. Driving four or five hours round trip to work on a house gets old quickly, especially when the project isn’t moving forward.
Mental energy. Probably the biggest one. That deal had been sitting in the back of my mind for nearly two years—every month as an unresolved problem. Once it closed, that mental bandwidth was suddenly free again.
Lessons From the Loss
This was the first deal I’ve lost money on since starting the business in 2020. At this point we’ve done roughly 160–170 deals, so statistically that’s not a bad track record. But every loss still teaches something.
The biggest lesson was that location matters more than you think. Rural properties can be much harder to exit because the buyer pool is so limited.
Another lesson was about the “in-between” property. This house needed just enough work to scare off most retail buyers but didn’t leave enough margin for flippers. Deals that sit in that middle zone can stall out.
And finally, I realized something about myself. I actually enjoy carpentry and remodeling. Working on houses is satisfying. I had forgotten that. But I definitely don’t enjoy doing it two hours away. If I do more renovation projects in the future, they’ll be much closer to home.
Moving On
Even though this deal ended with a $43,000 loss, closing it was still the right decision.
Sometimes the smartest move in business is not squeezing every last dollar out of a situation. Sometimes the smartest move is ending a problem and moving forward. That’s what this deal was. It’s done. The capital is back in circulation. And the mental energy is back where it belongs—focused on better deals ahead.