Why We Opened a Flea Market in the First Place
The story behind The Old Pioneer, our move, and a dream worth fighting for.
People sometimes ask us why we decided to open a flea market.
The truth is, we didn't.
At least not at first.
There wasn't some lifelong business plan tucked away in a drawer. I didn't grow up dreaming about booth layouts and vendor contracts. Momma and I didn't sit down one day with a five-year plan titled How to Become Flea Market Owners.
It started with me saying something along the lines of:
“Wouldn't it be cool if…”
And apparently, those are dangerous words in our family.
That one little question eventually became The Old Pioneer Flea Market in Jackson, Missouri — and the beginning of a story none of us could have predicted.
If Not Now, Then When?
At the time, I was working for an HVAC company.
Before that, I'd worked for a window and siding company where I had completely revamped their filing system. A friend from high school came in, saw what I was doing and asked if I wanted a job doing essentially the same thing for the HVAC company.
Their filing system was…well…
A mess.
A BIG mess.
It took a couple of months, but eventually I got everything organized and running smoothly. Once the hard part was finished, I was usually working from about 7 a.m. until noon during the week.
The front portion of the HVAC company's building was sitting empty, and the owners had decided to offer it for rent.
One day I mentioned it to Momma — Bobbie Jo — almost in passing.
Something like:
“Wouldn't it be cool if we opened a flea market up there?”
Now, this is where timing matters.
Momma was working for a wealth management broker at the time, and she had very recently battled breast cancer.
She was beating it.
But cancer had already taught her something none of us particularly wanted to learn:
Life is short.
So instead of giving me all the perfectly reasonable reasons why opening a flea market was probably a ridiculous idea, she had a different reaction.
Why not?
If not now, then when?
And somehow, “Wouldn't it be cool if…” turned into us renting a building.
Okay…So Apparently We're Doing This
Once we decided to do it, we went all in.
I planned the booth spaces and researched everything we would need to operate the market and bring in vendors. Momma handled most of the legal startup side — taxes, licenses and all the other fun things nobody pictures when they're imagining opening a flea market.
She did all of that while still working her full-time job.
I continued working for the HVAC company in the back of the building and then went up front to work on the market. I'd work for them until around 10 a.m., continue answering their phones until 5 p.m., and somehow manage the flea market at the same time.
Meanwhile, I was also Momma to three wildly active kids and wife to a husband working swing shift.
Totally reasonable workload.
Everything was fine.
🔥 This is fine. 🔥
Except the response to the market was incredible.
We had a waitlist before we even opened.
People were literally knocking on the doors wanting to shop the handful of booths vendors had already started filling.
We hadn't officially opened yet and customers were basically saying, We don't care. Let us in.
That's when we realized this crazy idea might actually work.
It also became painfully obvious that I couldn't keep doing everything.
Something had to give.
So I went to my boss — who also happened to be our landlord — and talked to him.
He told me I'd already done the hard part for them. I'd fixed the filing system they needed me to fix, and at that point he'd rather have me as a tenant than a part-time employee.
So I left my job and started running the market full time.
Then we kicked the landlord out.
Okay, okay. Not exactly.
But the response was so good that we knew almost immediately we needed more room. Luckily, they had another building they could move their HVAC operation into, which allowed us to take over their space too.
The Old Pioneer officially opened November 1, 2021.
By January 2022, we expanded from roughly 2,000 square feet to about 4,500 square feet.
And that filled up incredibly fast too.
We couldn't believe it.
Then Momma Had to Choose
The week before our grand opening, something happened that was both terrifying and, in its own strange way, a blessing.
Momma had requested the week of our grand opening off from her job.
She'd been promised she could have it.
Then, the week before, she was essentially told she needed to choose:
Her job or her dream.
Momma set one of the greatest examples I've ever seen a woman, mother, grandmother and business owner set.
She chose her dream.
She walked away from a very well-paying job and came to work at The Old Pioneer with me full time.
For about three months, we were living it.
Mother and daughter, working together every day, running this thriving little flea market we'd built out of one random Wouldn't it be cool if…
Unfortunately, those same three months were a nightmare when it came to Momma's health.
She kept finding lumps.
Eventually, one of those lumps turned out to be a tumor with cancer on it.
The doctor explained that Momma “didn't have cancer,” but the tumor inside her did.
To which our family basically responded:
What the hell is the difference?!
Cancer is a bitch.
There's really no prettier way to put that.
Between treatments, surgeries — and there have been numerous surgeries over the years — medical expenses and the absolutely ridiculous cost of paying for health insurance out of pocket, Momma eventually had to return to a traditional job for employer-provided health insurance.
But she never really left The Old Pioneer.
Her role just moved a little farther behind the scenes.
She's still here most days from about 4–5 and most Saturdays. She's still part of the decisions. She's still part of what we've built.
We adjusted.
We made it work.
And the market kept thriving.
Until March 2023.
The Day Our Roof Blew Off
Apparently, the wind decided our parking lot needed a roof more than our building did.
And yes.
I mean that literally.
What makes that day even stranger is that I remember it being sunny and bright outside. I don't even remember seeing a cloud in the sky.
But standing inside at our workstation, I would've sworn we were in the middle of a tornado.
The building shook.
The windows rattled.
There were sounds of destruction all around us.
For a moment, we literally reached out, grabbed onto each other and braced ourselves.
And then…
It stopped.
We slowly peeked outside, fully expecting to see a tornado, a tornado path — something.
It actually took us a minute to realize what had happened.
Our roof was lying in the parking lot beside the building.
Debris was scattered everywhere, including on vehicles.
It was terrifying.
And one of my first thoughts was:
I'm watching my dream end right here.
The Month We Didn't Know What Came Next
Surprisingly, we were able to keep operating for about another month.
Our landlords put massive tarps over the building and did everything they could to keep us going.
But naturally, this happened during what felt like the rainiest possible part of the year.
The tarps weren't enough.
Drop-ceiling tiles started falling. Water was getting into the electrical system. Eventually it became obvious that staying open wasn't safe.
We announced that we were temporarily closing.
The city came in the next day and told us that if we hadn't closed ourselves, they would've closed us.
So…
Good call, I guess.
During those weeks, there wasn't much news to give our vendors because our landlords were doing their due diligence — getting multiple quotes and considering different options.
Eventually, they came to us with a plan.
They'd already been considering an expansion, and they wanted to build that expansion before repairing our roof so everything could be roofed at the same time.
From their perspective, it made sense.
From ours?
We knew how long construction projects can take.
We couldn't afford to sit closed indefinitely waiting for it.
So for the first time since we'd opened The Old Pioneer, we had to seriously consider something we absolutely did not want to consider:
Closing permanently.
Hanging up our hats.
Calling it over.
I lost a lot of sleep during that time.
I was devastated.
But before we gave up, we started looking.
We Just Needed One Place
I looked at listings in Cape Girardeau.
We looked at a large building in Jackson twice because apparently once wasn't enough to convince ourselves that it was as bad as we thought.
Newsflash:
It was worse.
That building needed to be torn down. There was no saving it with anything resembling a reasonable budget.
Things weren't looking good.
Then one of our vendors messaged us.
“I know a place that might work.”
We contacted the landlord.
His family happened to be into antiques and junking, so when we explained what we wanted to do, he was excited.
We were excited.
During our first conversation, only about 7,500 square feet — three units — was available.
By the time we pulled onto the property to look at it, he'd already arranged for us to potentially have four units totaling around 10,000 square feet on the main level.
We pulled into the lot and saw this huge, open, completely bare space.
The possibilities were endless.
We were practically ready to start mentally placing booths.
Except…
Nobody was there.
We messaged the landlord.
Turns out we were looking at the wrong building.
It was next door.
😂
So we moved over to the correct building.
And I cannot adequately explain the disappointment when we walked through that door.
It wasn't that the building wasn't nice.
It was.
But within spitting distance of the entrance there seemed to be about six doors.
And walls.
So. Many. Walls.
The units were chopped up and separated into so many different spaces that none of us could wrap our heads around how you could possibly turn it into a flea market.
Even I, the eternal optimist who desperately wanted this to work, said:
“I don't know how we can make this work.”
Josh shook his head.
Momma shook her head.
They couldn't see it either.
Then the landlord said something that changed everything.
Essentially:
No, you don't understand. I want you in here. None of these walls are load-bearing. We can bring a Bobcat in and take them all out.
WAIT.
Now you've got my attention.
My brain immediately started racing.
And then:
“Wait! We need a bathroom. Hold off on the Bobcat!”
Within an hour or so, we'd gone from I don't know how this could possibly work to negotiating which walls needed to disappear and which ones needed to stay so we could keep bathrooms, storage and the upstairs areas.
We desperately needed a home.
He was excited about having one large tenant instead of managing multiple smaller ones.
And just like that, it became pretty obvious:
This was going to be the new Old Pioneer.
Taking Apart the Old While Building the New
And this is the part I wish we'd taken more pictures of.
At the time, nobody was thinking about documenting some big inspirational before-and-after story.
We were thinking about getting the market moved.
There were booths and walls to dismantle at the old location while there were floors, walls and a seemingly endless list of projects waiting for us at the new one.
[PHOTO: Dad and Josh removing the walls at our first location]
Dad and Josh taking down booth walls at our first location in 2023. Moving a flea market involves a whole lot more than packing boxes.
At the same time, we were trying to turn the new building into something that actually resembled The Old Pioneer.
[PHOTO: Momma, Dad and Josh working on the flooring at the new location]
Momma, Dad and Josh working on the floors at our new location. Somewhere in all this mess was the next version of The Old Pioneer.
There was something strange about watching one version of our market come apart while, just a few miles away, another version was slowly coming together.
We didn't have much time to get sentimental about it.
We had a deadline.
And Then We Got to Work
Everything happened ridiculously fast after that.
We knew what our deadline was.
Memorial Day weekend.
The local 100-Mile Yard Sale happens that weekend, and there was absolutely no way we were going to miss the opportunity to reopen with that kind of crowd coming through the area.
There was just one tiny problem.
The building had to actually become a flea market first.
The landlord had hired a small construction crew, and we knew they were going to have trouble meeting our completely unreasonable timeline if they had to handle every little thing.
So we joined the crew.
For more than a month, we were there 17 hours or more some days.
We arrived hours before the construction crew.
We left hours after them.
We cleaned.
We hauled.
We tore things apart.
We put things back together.
We handled the little things.
We did anything and everything we could so that when the actual crew was there, they could focus entirely on the things only they could do.
And we did it.
By the third week of May, vendors were filling booths.
Memorial Day weekend arrived.
And somehow, once again, we had a fantastic grand opening.
But We Didn't Do It Alone
Here's the part of this story that matters more to me now than I think I understood at the time.
We only lost a couple of vendors during that entire move, and those departures weren't really because of what happened or because we changed locations.
Our vendors stayed.
They waited.
They worked.
They encouraged us.
They reminded us that they were in this with us.
People brought us home-cooked meals and desserts while we were spending those insanely long days working on the new building.
And Laverne, if you're reading this:
I still need some more of that banana bread, please.
My brother — a thirty-something-year-old man — was about ready to wife Laverne up despite a slight age difference because he fell so deeply in love with her cooking.
We were exhausted.
We were stressed.
We were probably filthy.
But we weren't doing it alone.
And somewhere in all of that chaos, I realized something.
It Wasn't Just Our Dream Anymore
When Momma and I first rented that little 2,000-square-foot space, The Old Pioneer was ours.
It was our crazy idea.
Our risk.
Our Wouldn't it be cool if…
But somewhere along the way, that changed.
It became a source of income for our vendors.
It became a place where collectors could find things they'd been searching years for.
It became somewhere local makers could sell what they created.
It became a place people stopped by just to visit.
It became part of our community.
And when that roof landed in the parking lot and I thought I was watching my dream disappear, I eventually realized something else:
There were a whole lot of people standing behind us who weren't ready to let it disappear either.
I'm reminded of that even now.
There are days when owning a flea market is exhausting.
There are days when something breaks, someone complains, the to-do list is three miles long and I wonder what in the world we got ourselves into.
There have been health scares, financial scares, building scares and more than a few moments when quitting would've been the easier option.
But then I look around.
At the vendors.
At the customers.
At Momma.
At everything we've built since November 1, 2021.
And I think about that first conversation.
“Wouldn't it be cool if…”
Momma had just learned one of life's hardest lessons.
Life is short.
If not now, then when?
Five years later, I think I finally know the answer.
Then was our time.
And every time life has tried to tell us that our time was over, somehow we've found a way to start again.
So why did we open a flea market in the first place?
Because we had an opportunity.
Because Momma was brave enough to say why not?
Because I was crazy enough to run with it.
But I don't think that's the whole answer anymore.
We opened The Old Pioneer because one random “Wouldn't it be cool if…” became something neither of us could have imagined when we first said it out loud.
And somewhere between that first empty 2,000-square-foot room, a roof lying in a parking lot, walls coming down, floors going in and everything The Old Pioneer has become today, this stopped being just our dream.
It became something worth fighting for.
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