That time you closed the impossible deal: 6 real estate stories to make you laugh, cry or cringe

If there’s one thing for sure, it’s that there’s never a dull day in the world of real estate. To succeed in this game you need grit, determination…and a solid sense of humor.

We reached out to our network of real estate agents, team leaders and coaches to round up a list of true real estate stories that will make you grateful for each day, even the tough ones.

If you’re in need of a quick break, sit back and let us tell you about that time...

Your listing caught fire

Today, Ron Howard leads one Baltimore’s premier real estate teams boasting upwards of 400 transactions per year with a community-first sales approach.

But for Ron, the journey to success was far from smooth. 

In fact, in his very first year as an agent, Ron found himself literally fighting fire to get the deal done. Here’s what happened:

“During my first year of business, I got a call from a bar owner that wanted to buy the house that was listed right next door to his bar. The terms were worked out and the buyer just needed help because he hated the seller of the house who was also the real estate agent. I helped him get the house under contract and a week later when we got to the house to do the home inspection. It felt like we were in a scene from the movie Backdraft, when we opened the front door we were greeted with a big cloud of smoke, the house was on fire!

Evidently the gas fireplace wasn’t installed properly, and we had to call 911. 5 fire trucks later they put the fire out and took 3 months to repair the damage, so we thought.  Nobody realized when the fire fighters were putting out the fire, they poked a bunch of holes in the roof and it rained for 5 days before our new final walkthrough.

When we got to the house water was pouring out of all the light fixtures in the main level as well as streaming down the wall. We heard the seller on the phone telling someone he had to plug all the leaks before the buyer got there for the walk-thru, uh-oh busted.

The water damage only took 2 months to repair and we came back for the walk thru. The first stop we made was the roof to make sure all the holes were properly patched. We all got off the roof and worked our way down to flights of newly carpeted steps until someone realized we were all tracking roof tar and destroying the new carpet. Thankfully, my carpet guy got there fast and removed the tar before it had set.

We closed a few days later and should have predicted the full out brawl we almost had at the settlement table. Thank God for the easy deals.”

Apparently, battling the elements is just another day on the job. 🔥

‍Botox saved the deal

When we asked our friend Dale Archdekin for a never-before-heard real estate story, the expert coach and objection handling extraordinaire put out a call to his sphere—and what he came back with was nothing less than jaw dropping.

Check out this anonymous story about an impossible auction deal.

“I was hired to market in conjunction with the listing agent to auction a great property. The challenge was that the couple had divorced, the sale was court ordered and she was trying to sabotage her ex (which I never understood as she was sabotaging herself as any reduction in proceeds would be a reduction to her too).

Between letting the pets potty inside, her being drunk or coming home in the middle of showings...it was a nightmare and I truly never knew what to expect.

I’m still even a little surprised that I had such a good turnout on auction day and successfully sold the property.

What sealed the deal? Well an accelerated marketing approach where buyers feel a sense of urgency and recognize that it’s an opportunity, I’d say.”

Thank goodness for high-octane marketing. But according to this agent, what really saved the deal was her ability to stay poker-faced throughout a truly unnerving situation. 

“Botox is to thank for not having been shot by this client. If I could express my thoughts, my face would have been in a perpetual state of WTF which would have probably made her all the more unhinged.”

‍The Zillow window shopper was a million-dollar cash deal

We’re big fans of the team over at Wemert Group Realty so when their agent Jennifer Rigsby hit us with the rainbow-colored unicorn of all lead conversion stories, we knew it was nothing less than kismet.

Here’s how it happened. 🦄

“I answered our leadline phone midday on a random Wednesday when a Zillow concierge call came through. The buyer was inquiring on a home that happened to be a custom new build in Winter Park, FL. I didn't notice the price at first, but while chatting and answering questions, I looked up the property to see that it was a $2.5M home. Being in the business for a while, and in our area, I know that these leads come and go but are not always ‘serious.’

The buyer asked to set up a showing to which I quickly obliged, and I figured best case I’d be meeting a great new client and worse case I would get to see a gorgeous home! Two days later, the showing went perfectly, and while we were wrapping up the buyer casually mentions this is a cash transaction and she’s all in if we can negotiate a few items. We were fully negotiated and executed the next day. 

This has been the unicorn of all deals: an internet lead, million+ cash buyer, and a one and done showing to offer!”

Lesson learned: Take EVERY call that comes through.

You never know when that “not-so-serious” lead is actually a highly motivated buyer with a briefcase full of cash.

‍The bakery worker was actually a millionaire

Barry Jenkins is the Team Owner and CEO of the Your Friends In Real Estate team in Virginia Beach.

He’s also a former Minister. 

But that doesn’t mean he’s immune to passing judgment just like the rest of us.

Here’s Barry’s honest (yet cringeworthy) story:

“One time a prospect called me to see a luxury home. She really liked the area and was motivated to move due to schools. I was slower that day and so I didn’t ask all the usual questions like if she was approved for a mortgage. 

Because she seemed motivated I decided to bring an agent with me for training. He was going to be my very first team member and I thought I could make an easy sale and impress him. 

We pulled up to the house and the only car in the driveway was a 20 year old two-door Ford with a purple racing stripe and rust on the hood/roof—it was pretty beat up. I instantly got both annoyed and embarrassed. I decided to give the person the benefit of the doubt and showed the home respectfully. At the end of the showing, it was obvious the person really liked the home and wanted it. I went into the prequalification process a bit and asked her about her credit and occupation. 

She quickly said she had bad credit and she worked at the bakery at Walmart. I wanted to just to run and hide. I was SO embarrassed. I quickly started to wrap the appointment up because it was a waste of time in my eyes. She then interjected that she wasn’t using a mortgage because she wasn’t borrowing the money. She had inherited millions of dollars and her first purchase was paying cash for a home. 

The saying, ‘never judge a book by its cover’ rang true in my ears and I acted super smart to my agent. I don’t think he fell for it because he knew how irritated I was about 10 min earlier.” 

A weekly meeting led to a long-term deal with Sotheby’s

Today, Liz Bentley is a thriving performance management coach who has graced stages across the US as a keynote speaker for events like the SHRM’s Leadership Conference, IBM’s Power Up Event, Microsoft’s Women’s Conference and more.

But when she first started, her prospects were few and far between.

So, when Liz got asked to speak at a friend’s local real estate office she felt like she couldn’t say no. The rest is history.

Here’s Liz.

“When I was starting the business I had some interesting clients and work but was still really at the beginning of building and growing it. And at that phase you’re not sure if you are going to make it. As we know most small businesses fail and coaching businesses fail at even higher rates, so it was pretty touch and go. I was asked by a friend I played paddle tennis with at my country club to come down to her real estate office and give a short speech on the work I did at her office meeting. A lot of moms I knew from the community worked in that office as well as my mother in-law and I was really dreading it and thought about canceling it many times. Not only did I think it was a huge waste of time but I also mistakenly thought I was better than a local real estate office weekly meeting (which I definitely was NOT). 

I went to the meeting and shifted my attitude, knowing that beggars can’t be choosers, and it went really well. The people were very welcoming and ended up liking my talk so much that they asked me to speak with the CEO of the company a couple days later.  When I met with the CEO she asked me if I gave speeches. I did not give speeches at the time, but I couldn’t afford to say no to anything so replied “yes”. She asked me what I would speak on and I rambled a couple of topics and she said speak on this…Then she asked the price and I said my hourly rate is $250 but a speech is $700 and she said why? To which I really had no answer because I was making this all up on the fly.  Somehow I navigated through the conversation and did the speech.Thankfully they liked the speech so much they asked me to do many more and then to give their annual company keynote. 

At that keynote, the CEO of Soethbys was there and when she heard my speech she asked me to come work with them. Since that time, Sotheby’s is our biggest client, I have worked continually with them for the last 9 years, coached the CEO of the real estate company for 8 years and it was a huge launching pad for my business and career.  Had I not gone to that office meeting none of this would have happened.”

A random Easter Day text turned into an awesome repeat client (and friend!)

No one likes working on a holiday.

So when Ryan Fitzgerald of uphomes and Raleigh Realty got a random text on Easter Day, he almost took a hard pass.

Here’s what happened:

“Every strong agent knows that one of the first things you're looking for when taking on buyer clients is motivation and timeframe. If they don't have the motivation or a timeframe it's likely to be a total waste of time.

One fall afternoon a buyer client asked me to see a fixer-upper home with a lot of acreage. This particular couple had a solid budget, however, they were going to have a tough time finding the home because of the amount of land they wanted. There wasn't necessarily strong motivation to move either since they currently owned a townhome and they wouldn't be ready to buy until they found 'the right one.' Without much going on that afternoon, I showed them the home and enjoyed their company when we met in person. They didn't love the house and would not be making an offer.

After a few months of going silent and admittedly not trying too hard to follow up with them since they were lacking motivation, I received a text out of nowhere...on Easter day.

I thought to myself no way in hell am I showing them a home on Easter when we could just as easily see the home on another day. This is the type of client you usually just say no please go find another agent, however, there was something she said that made me stick it out and show the home.

In her text, there was something about her own 'self-awareness' when she said 'I know it's Easter and I know I am asking a lot' that made me feel it could work out in my favor. Reluctantly, I showed her and her husband the home later that morning.

They didn't like the house. Ugh, what a waste of time I thought.

A few weeks later they asked to see a home that had been on the market for 100+ days 30-45 minutes from my house and outside of their price range. For whatever reason, I again showed them the home. I think I felt committed to making a deal happen at this point.

They wanted to make an offer on this one....for 20% less than the asking price!

I figured what the heck, let me write up the offer and see what happens...and the sellers accepted! I couldn't believe it!

To this day I have sold 2 of their other rental properties and we have dinner together once or twice a year, they have become great friends!”

In the game of real estate there are good days, bad days, and days where the impossible turns out to be just another day on the job.

But as the Roman philosopher of Seneca once said, “Luck is what happens when preparation meets opportunity.” So stay hopeful and stay ready, because you never know when that next million dollar deal will come calling.