Flipping Houses Isn’t For The Faint Of Heart

Make no mistake, though, you need to have a heart to make it in this business.

Get an inside look at how we turned this extreme hoarder house into a dream home!

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Especially when you’re dealing with distressed properties and people losing their houses to bankruptcy and foreclosure. In times of exhaustion and extreme frustration, it may feel like the opposite of what you want to do. But leading with kindness can, and will, always produce a better result in the long run. Plus, it just feels better to know you weren’t an a$$ along the way.

Imagine, walking into a prospective house and you can barely move, let alone breathe. A small path requires you to turn sideways to access each room. You’re traveling blindly through mountains of paper, shattered holiday decorations, dust, fragmented furniture, strange odors, debris, and miscellaneous unknowns as you try to get a glimpse of the condition of the house. “How am I supposed to know how much to offer when I can’t even see anything?” You think, followed by the rationalization, “Well, maybe all this ‘stuff’ actually protected the walls and floors all these years.” Right? I mean, this iswhat we signed up for, after all. And then you remember ‘Someone actually LIVES here.’

It was a chilly day in Chicago, late January 2020. 

Two months before the lockdown. We stepped into the hoarder house, inhabited by a mid-50-something-year-old couple and their two American Huskies. The run down, 1920’s single family brick bungalow was situated on a rare, oversized city lot with ancient trees and lilac bushes, aptly covered by yard signs, more holiday decorations, dirty storage bins, and broken lawn chairs. It was a saving grace that Gregory, my partner & fiancé, had been a general contractor for more than twenty years. Without him I wouldn’t have had the courage to even walk inside. Even though this house was worse than anything either of us had seen on the popular A&E show, somehow Greg knew it had good bones. That, or we were so desperate for a deal, that we convinced ourselves it did. Our plan was to gut rehab it anyway, so we made an offer.

We competed with 4 other offers, 2 of which were higher than ours. 

Despite being lower than the highest offer by 20k we were granted the deal. How? We made an all-cash offer and allowed the seller to choose the closing date. We waived appraisal, inspection, and agreed to take the house in as-is condition. Now, I would never recommend any investor waive inspections unless you feel confident (as we did, thanks to Greg’s experience) that you know what you’re getting into. And even then, I guarantee, there will be surprises along the way that not even the smartest, most talented and psychic contractor could have ever foreseen. As-is meant we would be responsible for everything, including the clean-out. And this is where the story really takes a turn because we had no idea the sellers would be present the entire time! 

That was not supposed to happen. 

We were slated to close on a certain date in March. Two weeks prior I received an out-of-the-blue call from our attorney who said the bankruptcy court needed us to close the following day. Yes, the very next day. And if we didn’t close we would lose the deal. So, kinda-sorta-reluctantly-but-at-the-mercy-of-the-court we agreed. At closing I was also told the sellers needed more time to gather their ‘stuff’. Thinking back to that first and only time we’d attempted to walkthrough the property, I figured (and feared) this would be the case. Post-closing possession is rarely, if ever, desirable. But we had no other choice.

Emergency Closing.

We agreed to close on the property and include a stipulation that would permit the sellers to remain in the house for four extra days. If they didn’t leave by the designated date, we had permission to: 1. Start the junk removal process and 2. Collect a defined amount of money held back in escrow as compensation. Didn’t sound like the worst deal in the world. If everything had gone as planned. Like I said above, though, the sellers refused to leave. And there was nothing we could do about it.

It is never fun to watch people suffer. It was unfortunate that this couple—Katy & Peter—lost their home. And if there was something we could have done to help them prevent that, you bet your bottom dollar we would have. The next best thing, in this case, was to roll with the punches. Practically speaking, that meant help the sellers uncover as many buried valuables as possible during this week-long treasure hunt. And, despite the fact that we now legally owned everything in the house, let them take with them whatever they wanted. Katy and Peter rummaged through 3 stories of ‘stuff’, shaking their heads in disbelief and resentment almost the entire time, salvaging what belongings they could and taking multiple trips outside to make it all fit inside their one moving truck and PT Cruiser. They were angry with us, the bank, the court, the lawyers, the Realtors, the movers, the neighbor. Anyone they could blame, they blamed.

Be a light in someone’s darkness.

Their ‘light’ grew dimmer by the day. I could see it in Katy’s eyes from various conversations we’d had that week. I felt how disappointed she was, and even though they undoubtedly played a role in the eventual outcome that led to their house being foreclosed on, her sadness was palpable. She was helpless and hopeless.  I learned that, like many houses in this neighborhood, it was a multi-generational house, passed down to her by her aunt who had inherited it from her grandfather. She’d hoped to pass away here, and now it was very clear that that would never happen. 

This was something Greg and I had to come to terms with in order to help us through all of the exhaustion and frustration. We needed to dig deep, to find patience, compassion, and tolerance. Somewhere, somehow. We revisited our vision–which was a bright, glowing light—to turn this neglected house into a beautiful home for a new family one day. And came back to our why. Why are we in this business? To help people.

Things don’t always go as planned. 

Particularly when you’re rehabbing hundred+ year old houses and working with homeowners who aren’t selling voluntarily, for a profit. So, let kindness lead the way. We are all here to make money. But if we don’t do it with love in our hearts, and treat people with human dignity in the process, then nothing else really matters. 

8 days, $12,000, 11 junk trucks, a few hundred pounds of uncovered treasures, and an empty house (save for the mice) later—Katy & Peter finally decided to leave. 

And that escrow money we were owed? We waited six months, and only got half of what was promised, because the seller’s attorney said we forced them out. As with everything in life we have learned that you can’t please everyone. We really tried our best to help. Sometimes, your best just isn’t good enough.But that doesn’t mean we stop trying. 

*Names of the homeowners have been changed to protect their privacy.*

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