Alex Wolking’s Funny Real Estate Stories: Naked, Haunted, and Awkward Showings!

Alex Wolking’s Funny Real Estate Stories: Naked, Haunted, and Awkward Showings!

Naked fiascos to ghostly chills: Alex Wolking reveals Real Estate Showings like never before!

Ready for an exclusive behind-the-scenes look at the wild side of real estate? In this bonus content, we’re back with Chicago real estate guru Alex Wolking, who peels back the curtain on some of his craziest showings—from stumbling upon unsuspecting tenants in their birthday suits to discovering spooky surprises in the attic. If you ever wondered what really goes on when a house hits the market, buckle up for these hilarious, haunted, and downright awkward tales!

In Alex’s main episode, we explored his journey from a driven Midwestern kid who knew he wanted to sell homes by age 12, to becoming a top-producing broker in one of the nation’s most competitive markets. We dug into how he built a brand by combining genuine warmth, data-driven insights, and out-of-the-box marketing strategies. Alex also revealed how he stays inspired—citing interior design, modern architecture, and that Midwestern charm as key facets of his success. Now, in this bonus session, it’s time for a lighter (and spicier) side of real estate!

What You’ll Hear In This Bonus Episode

  • Naked Showings: The unexpected (and often hilarious) moments Alex encounters when tenants don’t get the memo.
  • Ghostly Encounters: From eerie attics to strange temperature drops, Alex shares the one property that made him a total believer in haunted houses.
  • Scandalous Situations: That time Alex’s clients nearly caught a secret affair in progress!
  • Real Estate Shenanigans: Find out how listing agents, suburban showings, and “mysterious disclaimers” keep Alex on his toes.

Why Listen?

  • Hilarious Real Estate Confessions: A comedic glimpse into what doesn’t make the polished listings.
  • Behind-the-Scenes Insights: Learn how even top brokers face chaotic surprises—and handle them with grace.
  • Carryover from Main Episode: Build on the deeper story of Alex’s ascent into real estate stardom with these entertaining extras.

Share Your Thoughts:

  • Have you had a haunted or hilariously awkward house experience? Let us know in the comments or on socials.
  • Don’t forget to subscribe, leave a review, and share this bonus episode with anyone who could use a laugh (or a ghost story)!

🔥 Meet Alex Wolking:

A second-generation real estate broker with over two decades of experience, Alex has become a powerhouse in Chicago’s dynamic real estate market. Known for his exceptional expertise in historic properties, luxury condos, and co-ops, Alex doesn’t just sell homes—he sells stories. His boutique team consistently ranks among the top producers on Chicago’s north side, and today, he reveals the secrets behind his unique approach.

🔗 Connect with Us

Follow Alex Wolking:

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Website: alexwolking.com

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House of Style: houseofstyle.com

Transcript
Speaker A:

Hey, thanks for sticking around.

Speaker A:

This is our exclusive bonus section.

Speaker A:

We're here to continue our wonderful conversation with Alex Wolking.

Speaker A:

So I have a few more fun questions.

Speaker A:

We're loosey goosey now.

Speaker A:

We're opening it up.

Speaker A:

Give me.

Speaker A:

I want.

Speaker A:

I want some stories.

Speaker A:

We've been talking about stories this whole time.

Speaker A:

What's the wildest thing that's happened in a showing?

Speaker B:

Oh, Jesus.

Speaker B:

How much time we have?

Speaker A:

Let's rank the stories in order of amazing.

Speaker B:

Okay?

Speaker B:

So I can't tell you how many times I've walked in on people butt, ass naked, you know, coming out of the shower, having.

Speaker B:

Did they forget that?

Speaker A:

There was.

Speaker B:

A lot of times, Grant, they are.

Speaker A:

Did they want you to see it?

Speaker B:

No, a lot of times, Grant, they are tenant occupied properties rentals that no one communicated that there was a showing or frankly, they just didn't care if there was a showing.

Speaker B:

I've had some of that before.

Speaker B:

People that are coming out of the shower, wrapping themselves up in towels.

Speaker B:

People that are having an afternoon delight I've walked in on.

Speaker B:

I had a listing once about eight years ago, where it was a big old mansion.

Speaker B:

Oh, my God.

Speaker B:

It was a really cool house.

Speaker B:

Stunning architecture.

Speaker B:

But I walked up to the attic, and it was an Italian villa style of architecture.

Speaker B:

So you had this big central tower, like a cupola, basically.

Speaker B:

Me being the naive young broker I was at the time, I was like, I just wanted to go see.

Speaker B:

The house is, like, perched really high up on a hill, and I go up the windy.

Speaker B:

You know, the circular staircase to get to the tower, and there's a noose hanging from the rafters.

Speaker B:

I still have a picture of on my phone that still freaks me out to this day.

Speaker B:

That was freaky.

Speaker A:

Did we ever learn the story behind that?

Speaker B:

I had.

Speaker B:

I.

Speaker B:

I walked in on a.

Speaker B:

At least walked in on something.

Speaker B:

But I definitely.

Speaker B:

I was with clients showing a house and later found out that, you know, there was.

Speaker B:

Well, there was a couple there.

Speaker B:

They were like, you know, scurrying away to the car.

Speaker B:

So, sorry, we're on our way out, like, okay, fine.

Speaker B:

And then the showing didn't last too long, but my clients liked the house.

Speaker B:

We're standing out in the driveway, and another car pulls in the driveway, and this woman gets out and she's like, oh, I'm so sorry.

Speaker B:

Are you guys still looking like.

Speaker B:

No, no, no, we're good.

Speaker B:

We're good.

Speaker B:

We later found out that the older man and the younger woman, that was actually the husband and his mistress and the wife had come Home and just missed them.

Speaker B:

Yeah.

Speaker B:

Did not know because I explained to the listing agent what happened.

Speaker B:

She's like, I knew something was going on.

Speaker A:

I wonder if she shared.

Speaker A:

I, you know, wow.

Speaker B:

There's a lot of that happens at realtors.

Speaker A:

I mean, they were selling their homes.

Speaker B:

That could be a way out too.

Speaker B:

Who knows?

Speaker B:

But I just found that very funny.

Speaker B:

I showed a condo once that was haunted and I became a believer in haunted properties after as many historic homes I've sold, you would think I'd believe it goes.

Speaker B:

Yeah, I didn't really think much about it.

Speaker B:

I always thought the paranormal shows were until 1.

Speaker B:

Until 1.

Speaker B:

And it was a condo that was built in like the late 90s.

Speaker B:

And I walked in and I just make it a quick story.

Speaker B:

My client, who.

Speaker B:

She's like, why is this condo still on the market?

Speaker B:

It's priced really well.

Speaker B:

And I was like, I don't know, let me look.

Speaker B:

So I started looking through the disclosures and I saw a disclosure I had never seen before.

Speaker A:

Ghosts.

Speaker B:

It was a stigmatized property disclosure.

Speaker B:

It was the owner disclosing that even though it's not material to the home, it was still something that could adversely affect a buyer's decision to purchase the property.

Speaker A:

Is that really.

Speaker B:

It's not necessary.

Speaker B:

Not in the state of Illinois, in California, New York.

Speaker B:

It is.

Speaker B:

Texas, I think it is as well.

Speaker B:

There's a couple states where you have to disclose it, but not in Illinois.

Speaker B:

And at that time, this is in Iowa.

Speaker B:

Not in Iowa either.

Speaker B:

And my client, who was a member of the local paranormal service, she's like, I don't care.

Speaker B:

Because we found out that the husband had died by suicide in the basement or something.

Speaker B:

So like, okay, well, as long as you know that going into it, she's like, all right, well, as long as he moves out when his wife leaves, when his widow leaves, then I don't care.

Speaker B:

All right, fine.

Speaker B:

So go and look at it.

Speaker B:

There was stuff kept going off randomly.

Speaker B:

There was like some Disney toys that must have been their grandkids.

Speaker B:

That the only way, I forget there was like a Merlin or something in like a globe.

Speaker B:

The only way you could make this thing go off is if you put your hand on it and touched it.

Speaker B:

Then we go down to the basement and as we approach the basement steps, the steps started making noise like somebody was walking on them.

Speaker B:

You're like, well, this is freaky Merlin.

Speaker B:

We get down to the.

Speaker B:

Must have been.

Speaker B:

We go down to the basement.

Speaker B:

Oh, we also heard footsteps.

Speaker B:

This is a one story condo.

Speaker B:

We heard footsteps in the attic above.

Speaker B:

That was creepy, too.

Speaker B:

So we get down to the basement, and we go around, and there was just this presence that was so palpable.

Speaker B:

And I was like, why do I feel like we're not the only ones here?

Speaker B:

Like, I feel like someone else is here.

Speaker B:

There's a room in the back of the basement that was like a storage room.

Speaker B:

We get up to the door, and the door on it said, dad's room.

Speaker B:

I was like, dad's room?

Speaker B:

And the guy died.

Speaker B:

Oh, God.

Speaker B:

So we opened it up.

Speaker B:

It was Dad's.

Speaker B:

It was his workshop.

Speaker B:

He had all his tools in there.

Speaker B:

And there was, you know, the tools along all the wall, and there was, like, some, you know, stuff in the middle of the room.

Speaker B:

So that kind of.

Speaker B:

You walked around the room in, like, a circle.

Speaker B:

Second we open that workshop, the temperature changed by a good 10 degrees.

Speaker B:

And we.

Speaker B:

So then we walked around to the other side to see the rest of the room.

Speaker B:

Cause there was a closet and everything else.

Speaker B:

I'll never forget this for as long as I live.

Speaker B:

My client, she gets to that spot.

Speaker B:

She turns and looks at me with this, like, deer in the headlights look.

Speaker B:

And she's like, I think I'm standing right where he is.

Speaker B:

And I was like.

Speaker B:

Her teeth started chattering because the temperature dropped another 10 to 15 degrees.

Speaker B:

So.

Speaker B:

And by the way, the air was not on.

Speaker A:

Ghosts are real.

Speaker B:

Totally.

Speaker B:

So she's like, I've seen enough.

Speaker B:

So we start going up the stairs.

Speaker B:

Well, and we go back upstairs.

Speaker B:

And again, even back in, like, the rec room area in the basement, the temperature had changed about a good 20 degrees.

Speaker B:

So we go upstairs, and we're putting our shoes on and putting our shoes on to leave.

Speaker B:

Me, being the smart ass that I am, had my hand on the doorknob.

Speaker B:

I'm like, all right, well, have a good day.

Speaker B:

The Merlin thing went off again, and I went to go, like, pull the door.

Speaker B:

I was just slowly pulling it, and I felt the door get shoved, Shot, basically, get out is what it was.

Speaker B:

I was like, okay, well, I've seen enough.

Speaker B:

Oh, yeah, I have seen enough.

Speaker A:

That's solid.

Speaker B:

That was.

Speaker B:

That was.

Speaker B:

That was my haunted ghost story that makes.

Speaker B:

Oh, yeah, I found sex toys.

Speaker B:

I found.

Speaker B:

Oh, my.

Speaker B:

I'll never forget.

Speaker B:

I had a client's home that was being staged.

Speaker B:

And, you know, the photographer was coming, and I walk in on some fun from the night before that was left over and, like, make the bed.

Speaker B:

And it was all in a day's work.

Speaker A:

Apparently ghosts and sex toys.

Speaker A:

Lay out.

Speaker A:

Are There times where I always think about this because I think about my relationship with other stylists or designers.

Speaker A:

And from the designer standpoint, I think there are incredible designers out there and they have nothing to do with what.

Speaker A:

There are plenty of people that are, you know, getting.

Speaker A:

Getting things.

Speaker A:

But I often look at other stylists.

Speaker A:

I'm like, yeah, really are.

Speaker A:

Really.

Speaker A:

Do you feel that way about other brokers?

Speaker A:

Are there some that you see that come into it, whether it's your listing or you're going to theirs regularly, that you're just like.

Speaker B:

There's definitely some cringe moments and it's.

Speaker A:

You have a nemesis.

Speaker B:

You know, I used to.

Speaker B:

And then it kind of fizzled out.

Speaker B:

It was kind of fun though.

Speaker B:

I enjoyed having an arch nemesis.

Speaker A:

I mean, something extra.

Speaker A:

It does.

Speaker A:

I mean, when you're building house of style right now, like the broader business, I mean, there's so many revolutionary things to it that there are plenty of haters and the naysayers that this isn't gonna work.

Speaker A:

I am sure I'm doing this because I believe in it wholeheartedly.

Speaker A:

But I'm also doing it a little bit to stick it to you.

Speaker B:

Sure.

Speaker B:

Competition really happens at the bottom and collaboration happens at the top.

Speaker A:

Interesting.

Speaker B:

And that's the thing I've noticed is.

Speaker B:

And that was when I was like scrappy and just let me at em.

Speaker B:

There's one agent, he and I definitely sparred.

Speaker B:

It was kind of fun.

Speaker B:

Cause it made me sharper.

Speaker B:

It was great.

Speaker B:

Just get pissed at the time.

Speaker B:

Kept him on it.

Speaker B:

Oh yeah.

Speaker B:

But also kind of kept him on his toes, kept me on my toes.

Speaker B:

And then it just ended up not being fun anymore.

Speaker B:

So he just kind of gave up.

Speaker B:

Well, there went my fun.

Speaker A:

So you gotta instigate it with somebody new.

Speaker B:

Well, I thought about that.

Speaker B:

And then the more I thought about it, I'm just like most of the agents.

Speaker B:

Really.

Speaker B:

The thing that I've seen more than anything is so many agents just do so many cringe things where I just kind of, you know, have a face palm moment where I see, you know, I'm never gonna knock an agent who's trying.

Speaker B:

If an agent's trying, you know, they're trying with video, they're trying with marketing, whatever.

Speaker B:

I've been that agent.

Speaker B:

So I mean, by all means, I'm not gonna sit and judge somebody.

Speaker B:

Cause I've definitely been in their shoes.

Speaker B:

I see it a lot on the high end when you can tell when an agent doesn't necessarily work with a lot of clients in that Price point in that space, you can kind of tell.

Speaker B:

And it's not necessarily a bad thing.

Speaker B:

They're learning.

Speaker B:

But what's really bad is when agents start pretending like they know everything and they end up getting information wrong and.

Speaker A:

Don'T have the ability to pull.

Speaker B:

They don't have.

Speaker B:

Or ask the right questions or ask somebody who would know the right questions.

Speaker B:

I've been guilty of that.

Speaker B:

And it's a.

Speaker B:

I see it a lot, especially with newer agents getting their license.

Speaker B:

And, you know, there's some agents who just talk too damn much.

Speaker B:

They.

Speaker B:

They.

Speaker B:

They won't shut up because their clients like, trying to place, oh, I want.

Speaker B:

I could put my furniture here.

Speaker B:

I could change the wall color to this.

Speaker B:

And then agents just yammering, yammering, yammering, yammering.

Speaker B:

I mean, how many times did you and I go into showings from, like, this agent will not shut up.

Speaker B:

Oh, my.

Speaker A:

Just like, I just want to walk through the house really quickly.

Speaker B:

Well, especially.

Speaker A:

I'll make my own decision.

Speaker A:

I don't need you.

Speaker A:

Like, tell me how wonderful everything is.

Speaker B:

Especially suburban agents, because they are so nosy, like, well, how many kids do you have?

Speaker B:

And where do kids go to school?

Speaker B:

Like, God bless them.

Speaker B:

They're just trying to make conversation.

Speaker B:

But sometimes that information is just not necessary.

Speaker B:

And also, it's none of your business, too.

Speaker B:

So it's just a little invasive sometimes.

Speaker B:

So sometimes I just gotta.

Speaker B:

I did have a showing a couple weeks ago where I actually told an agent, I pulled them aside.

Speaker B:

I'm like, hey, just let them look.

Speaker B:

Just.

Speaker B:

You may want to pull back a little bit.

Speaker A:

And they were.

Speaker B:

They were kind of offended at first, but I said in a very friendly, disarming way.

Speaker B:

And they actually, they called me later, like, hey, just thanks so much.

Speaker B:

Like, and they opened up like, this is my first big client I ever had.

Speaker B:

And I was like, listen, I've been in your shoes.

Speaker B:

Try this next time.

Speaker B:

But I always.

Speaker B:

I didn't just offer up advice like, do you want my opinion on this?

Speaker B:

And they're just like, oh, yeah, sure, that'd be great.

Speaker B:

And they like, you know, very sweet.

Speaker B:

They followed my career and they saw some other listings I had, and they were, you know, I found, you know, I had so many great mentors growing up.

Speaker B:

When I was coming up in the business, even before, when I was going, I went to open house because.

Speaker B:

Not just to see the product, but to learn about the agent and watch them work.

Speaker B:

And I learned from just watching people.

Speaker B:

I think mentorship seems to be gone in a Lot of the new generation, across all industries, people just want to go and be a star.

Speaker B:

They don't want to actually grind and hustle to get to where they, you know, where we've all had to work really hard to get to.

Speaker A:

Absolutely.

Speaker B:

I mean, my joke last year when I made the top 100 in Chicagoland by Chicago Magazine, I was like, well, if that isn't my brand, I don't know what is top 100.

Speaker B:

But we came in right at number 100.

Speaker A:

That's all that matters.

Speaker B:

So on brand.

Speaker B:

But that was a.

Speaker B:

But that took a lot of hard work.

Speaker B:

And also.

Speaker B:

And people go find somebody to help you if you don't know what you're doing for sure.

Speaker B:

I cannot preach that.

Speaker B:

I think people are too.

Speaker B:

I think especially younger people are just too proud to ask.

Speaker B:

God, I sound like, what do you want to know, kid?

Speaker A:

That's okay.

Speaker A:

That's okay.

Speaker A:

It's partially your vibe.

Speaker B:

It really is.

Speaker B:

It really is.

Speaker B:

Well, I remember there was that one broker that I sent you.

Speaker B:

She was wearing some flats, like, had this fabulous scarf.

Speaker B:

And I was like, grant, make me look like her.

Speaker B:

I was like the description and shout out to Marlene St.

Speaker B:

George with Jameson Sotheby's.

Speaker B:

I want to be her when I grow up.

Speaker B:

Her style is incredible.

Speaker B:

She had this fabulous gray hair and she's very like Palm beach, but also Midwest.

Speaker B:

And like just her house was phenomenal.

Speaker A:

Like, oh my God, I love the direction.

Speaker B:

I think I sent you her headshot multiple times.

Speaker B:

Like, her jewelry was phenomenal.

Speaker A:

All right, he's serious about this.

Speaker B:

She just.

Speaker B:

She had it.

Speaker B:

Oh, yeah, right.

Speaker B:

It was like, this is a very sophisticated woman, probably in her 60s, 70s if I had to guess.

Speaker B:

I'm like, God, I want to be her.

Speaker B:

I want to be her now.

Speaker B:

I don't want to be her when I grow up, I want to be her now.

Speaker B:

But that was.

Speaker B:

And of course, like, what other 30 year old millennial saying that about and like it Me.

Speaker A:

Hell yeah.

Speaker B:

It is.

Speaker A:

Hell yeah.

Speaker B:

Go look her up.

Speaker B:

Marlene St.

Speaker B:

George with Jamison.

Speaker B:

That's the only other broker I'm gonna plug.

Speaker A:

There you go.

Speaker B:

She's got style, man.

Speaker A:

Oh, she does, yeah.

Speaker A:

Lastly, what is your biggest pet peeve of clients that they do that you're like, oh, man.

Speaker B:

Oh.

Speaker B:

When they don't listen, like, we have been over this multip.

Speaker B:

Or I think in any industry, whether it's.

Speaker B:

I'm sure all of your medical clients can tell you, well, Google said this or I googled this and I researched that and all of A sudden, now they're the expert.

Speaker B:

Like, no, that's not how this works.

Speaker B:

Is what you just researched an option?

Speaker B:

Yes.

Speaker B:

In this particular situation, it does not make sense.

Speaker B:

And here's why.

Speaker B:

And a lot of times they'll back off because they're just like.

Speaker B:

Well, they just had to ask.

Speaker B:

They're just like, you know, if you Google your symptoms, you're always going to have cancer.

Speaker A:

Right.

Speaker B:

So I'm like, that's.

Speaker B:

It's no different.

Speaker B:

And that is so frustrating.

Speaker A:

Yeah.

Speaker A:

So frustrating.

Speaker B:

Yeah.

Speaker B:

It's just like, really?

Speaker B:

Or, you know my other favorite, don't.

Speaker A:

You know who I am?

Speaker B:

That's right.

Speaker B:

Or you.

Speaker B:

When clients want to ask your advice, especially if they're selling their house.

Speaker B:

Well, what do we need to do to sell this?

Speaker B:

Well, you need to paint this, you need to clean this, you need to update that.

Speaker B:

Well, we don't want to do all that.

Speaker B:

Okay.

Speaker B:

Then you're not going to get top dollar and you're not going to sell right away.

Speaker B:

So just be prepared for that.

Speaker B:

It's like they want your advice, but they don't actually want to take it and implement it.

Speaker B:

People have to.

Speaker A:

They want to know, but make their own decision.

Speaker B:

Correct?

Speaker B:

Correct.

Speaker B:

So, you know, I think that's probably.

Speaker B:

And listen, I'm guilty of it, too.

Speaker B:

We're all guilty of it.

Speaker A:

That's natural.

Speaker B:

Totally.

Speaker B:

That's probably my biggest frustration.

Speaker A:

I like that one.

Speaker A:

That's a good one.

Speaker A:

I resonate with that.

Speaker B:

Of course.

Speaker A:

Definitely hits.

Speaker A:

Yeah.

Speaker A:

Well, thank you so much.

Speaker A:

You have been absolutely fabulous.

Speaker B:

Thank you, Dan.

Speaker A:

I appreciate it.

Speaker B:

It was a pleasure seeing you.

Speaker A:

For all the viewers and listeners, thank you for hanging out with us for this extra exclusive bonus content.

Speaker A:

If you like this, keep coming back for more exclusive content each week.

Speaker A:

And tell your peeps to check out the House of Style podcast.

Speaker A:

I can't wait to see you there.

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