Sarahs Cake Stop

09/01/2026

**Chapter 4 — Rachel: The Face of Sarah’s Cake Stop**

When we started Sarah’s Cake Stop, I always assumed the face of the truck would be my sister Jill.

After all, it was her bakery.

Sarah’s Cake Shop was her business. She was the one creating the cupcakes, building the bakery and developing the products people would eventually chase around St. Louis.

But something happened not long after we launched the truck.

Jill started having serious back problems and ended up being out for a period of time while she dealt with complications and recovered.

That changed everything.

Suddenly, I found myself much more involved in the day-to-day operation of the truck than I ever planned to be.

Remember my original agreement?

I was not going to run the truck.

I was not going to drive the truck.

I was definitely not going to operate this business every day.

Yeah.

That plan was going really well.

At the same time, I was still working full-time at my software company.

And on top of figuring out the daily operation of the truck, I was also trying to figure out where we were actually allowed to operate.

Food trucks were still new in St. Louis.

Different municipalities had different rules.

Some cities didn’t allow us at all.

Others didn’t really know what to do with us yet.

I couldn’t exactly hand the keys to our new employee and say:

“Good luck. Go find somewhere legal to park.”

So for the first couple of weeks, I would drive the van to wherever we were going, help get things set up, and then let our new hire handle most of the selling.

Her name was Rachel Kitchen(Skaggs).

And very quickly, I realized something had to change.

# # # Handing Over the Keys

About two weeks after we hired Rachel, I decided it was time.

I handed her the keys.

I told her she was driving.

I would ride along, but if this business was ever going to work, I could not be the person driving the truck around St. Louis every day.

Rachel looked at me, took the keys, climbed into the driver’s seat and off we went.

I remember thinking:

Well, that was easy.

No argument.

No hesitation.

No pushback.

What I found out much later was that Rachel was completely freaked out.

She just didn’t show it.

That would turn out to be a pretty good description of Rachel in general. She would freak out....and then figure it out.

She handled things.

# # # Who Was Rachel?

Rachel grew up in Cuba, Missouri, on a farm with cattle.

She did not grow up with a lot of extras or comfort.

There were chores.

There was work.

And apparently, she learned very early that if something needed to get done, you did it.

She was also extremely smart.

Rachel was the valedictorian of her high school class.

After graduating, she moved to St. Louis to attend culinary and pastry school.

That was one of the reasons she had applied to Sarah’s Cake Shop in the first place.

At first, I thought we had hired someone to drive a truck and sell cupcakes.

We quickly learned we had hired something very different.

Rachel was a worker.

And she didn’t seem particularly interested in staying inside whatever job description we had given her.

She started taking on more responsibility.

Then more.

She began handling the daily social media.

She posted our locations on Facebook.

She talked with customers.

She listened to what they wanted.

She helped us figure out where the truck should go.

Little by little, she wasn’t just operating the Cake Stop.

She was helping build it.

And without any of us really planning it, customers began building a relationship with her.

# # # “Don’t Even Think About It”

I was still going out with Rachel on certain stops and events.

One day we were sitting at an event talking.

I’ve always enjoyed running, and at that point I had helped some people train for their first marathons.

Somehow running came up in the conversation.

Rachel suddenly looked at me and said:

**“Don’t even think about trying to convince me to run a marathon.”**

Whoa.

That came out of nowhere.

I wasn’t even trying.

But now?

That sounded like a challenge.

Over the next couple of months, we would occasionally talk about running.

I also talked about my connection to St. Jude Children’s Research Hospital.

St. Jude was one of the first organizations I donated money to after getting my first job out of college, and it had always been a cause that meant something to me.

I knew Rachel had a charitable side, so I started talking about people who combined running with fundraising.

Slowly, she started asking questions.

How do you start running?

How do people raise money?

How far is a 5K?

The next thing I knew, Rachel had signed up for one.

And at that point, there was no turning back.

# # # The Envelope

But the reason this story matters has very little to do with running.

It has to do with what Rachel quietly started doing with her tips.

She saved them.

Not for herself.

For St. Jude Children’s Research Hospital.

She didn’t make a big announcement about it.

She didn’t tell us at first.

She didn’t tell the customers.

She just had an envelope and started putting her tips into it.

When I found out, I thought:

We need to tell people what she is doing.

So we put out a tip jar with the St. Jude logo on it (shown here, and I still have in my office) and told Rachel she needed to let customers know she was raising money for St. Jude while training to run the St. Jude Marathon.

And our customers responded.

Rachel kept training.

She kept raising money.

And that following December, the person who had once told me—

**“Don’t even think about trying to convince me to run a marathon.”**

—crossed the finish line of her first marathon.

But something even more important came out of it.

From that point forward, **every tip collected on Sarah’s Cake Stop went to St. Jude Children’s Research Hospital.**

We continued doing that until the truck closed in 2020.

Ten years of giving started because our new employee quietly decided to put her tips into an envelope.

That became part of who Sarah’s Cake Stop was.

# # # The Face of the Truck

As the months and years went by, Rachel continued building a loyal following.

Our page eventually grew to nearly 15,000 followers.

And these were not passive followers.

They participated.

They suggested locations.

They commented on flavors.

They followed the truck around St. Louis. Sometimes literally!

They told Rachel about their families, jobs, kids, and whatever else was happening in their lives.

And Rachel built a true relationship with them.

For many customers, she wasn’t simply the person selling cupcakes through a window.

She was their weekly friend who happened to arrive in a pink truck carrying dessert. She was invited to weddings and birthday parties outside the Cake Stop.

Most of those customers didn’t know who Jeff was.

A lot of them didn’t know Jill.

They knew Rachel.

And looking back, I think that was one of the most important things that happened to the Cake Stop.

Jill and I may have created the structure of the business.

Jill and her team created the products.

I spent a lot of time working on the business side and trying to navigate the rules and politics surrounding food trucks.

But Rachel created something we couldn’t make in the kitchen:

**A relationship with the customers.**

I don’t think Jill or I ever imagined that was how the truck would grow.

But I know we were both incredibly happy that we had someone we trusted with the business.

Rachel became the first — and one of the most important — faces of Sarah’s Cake Stop.

With Rachel behind the wheel, Jill and the Cake Shop team producing some of the best cupcakes in St. Louis, and me doing my best to stay out of the way...

We finally had the beginnings of a pretty good team.

And we were going to need it.

Because while Rachel was figuring out how to build a following, I was discovering that selling cupcakes out of a truck in St. Louis was about to get a lot more complicated.

**Next Chapter: Cupcakes, Permits and City Hall**

08/20/2026

Chapter 3 — Learning How to Run a Food Truck
Getting the food truck home and setting up the business turned out to be the easy part.

We still had absolutely no idea how to run a food truck.
And here’s a little hint: it is not the same as running a smaller version of the Cake Shop.

The first thing I did was probably annoy my neighbors by parking this big white van in my driveway and starting the process of cleaning it and figuring out exactly what we had bought.

The van had run really well coming back from Philadelphia, and during that 900-plus-mile drive I had already learned a few things.

For starters, I didn’t need to run the giant generator the entire time I was driving. I think I made it about 20 miles outside Philadelphia before realizing that.

I also learned that the generator and the van engine both pulled diesel from the same fuel tank. Once the tank got down to about a quarter full, the generator would automatically shut off.
That was actually a pretty smart feature. It meant you couldn’t accidentally run the truck out of diesel while sitting at an event with the generator running.

One less thing for us to screw up.

I spent the rest of the weekend cleaning the van.

My brother came over, and the two of us started trying to figure out the electrical system, the generator and what exactly this truck had originally been built to do.

The built-in Kohler diesel generator was 20,000 watts.
That seemed like an unbelievable amount of power for what we needed. I started wondering if maybe I should have taken the cash from the guy in Philadelphia who offered to buy the generator from me.

But it also raised another question.

Why did whoever originally owned this van need that much power?

There wasn’t any equipment left inside that explained it.
My Russian friend in Philadelphia certainly hadn’t known anything about the history.

Then we noticed a small stainless-steel plaque mounted on the back of one of the counters.

It said:
VENTI VAN
Ahhh.
Now we had a clue.
This must have been some kind of coffee truck.

So we tracked down the manufacturer and called them, thinking we were finally going to learn everything about our mysterious van.

Nope.

About the only thing they would tell us was that the truck had originally belonged to Starbucks. Apparently, Starbucks had used these vans as temporary locations outside new stores while those stores were being built.

But at least we now knew two things:
1. The truck had been professionally built.
2. And we had probably gotten a really good deal.

How Hard Can It Be to Move Cupcakes?

I may have bought more truck than we actually needed, but at least we had one. Now we had to figure out how to transport cupcakes.

Our brilliant solution was a commercial speed rack.
We installed it in the far back of the van near a refrigeration unit we weren’t planning to use. I bolted the rack to the floor and then secured it to the side wall.

We would simply slide sheet pans full of cupcakes into the rack.
Problem solved.

EASY PEASY.

We had this food-truck thing figured out. Now we just needed somewhere to go.

Making It Look Like Sarah’s Cake Stop

Before we hit the streets, we needed to do something about the big white van. Neither Jill nor I knew anything about vehicle wraps, so we found a guy in the city who said he could handle the design and wrap.

Deal.

We gave him pictures of cupcakes that we wanted blown up on the sides of the van. The goal was pretty simple: make the truck noticeable and make every driver sitting next to us at a stoplight want a cupcake.

We paid him, dropped off the van and waited.

When we got it back, it looked completely different.

Jill and I both said we loved it. I also think both of us were quietly thinking: HMMMM...something about this isn’t quite right.

But whatever. LET’S GO!

We officially had the first version of the Sarah’s Cake Stop truck.
Looking back at the pictures today, I can admit it: It was one ugly wrap. But it was our ugly wrap. And we were proud of it.

Now We Needed Someone to Work on it

Remember my original agreement?
I was not going to work on the truck.
I was definitely not going to drive the truck.
So naturally, our next task was to find someone who would.
I interviewed a couple of people and neither one seemed like the right fit.

Around that same time, Jill had interviewed someone for the Cake Shop. She told me that if I couldn’t find anyone, I should talk to her new hire and see if she might be interested in working on the truck part-time.So I sat down with the new girl.

Her name was Rachel Kitchen!

Pretty good last name for someone we were considering putting on a cupcake truck.

Rachel was a little shy, but she passed my interview process — which, if I’m being fair, was not exactly extensive.

I had no idea whether she would be the long-term person for the job. At that point, I was just happy we had our first employee.
Anyone who followed the Cake Stop for very long probably already knows where the Rachel part of this story eventually goes.

But we’ll get to that.

First, Jill and I had scheduled our maiden voyage.
July 14, 2010.-The Missouri Botanical Garden Concert Series.

Jill and I loaded the van with about 200 cupcakes, along with water, sodas, milk and a bunch of other stuff we thought we might need.

And off we went down Highway 40 toward the city.
That day would become the first of many lessons the Cake Stop taught us.

As we got near the Botanical Garden, we started looking for somewhere to park.
And kept looking.
And kept looking.
We drove around for what felt like forever — probably close to an hour. Eventually, we found a spot about two blocks away, along the side of the Garden.

It wasn’t anywhere close to the main entrance.
But we finally had a parking spot.
We were excited.
This was it.
We were actually going to open the serving window for the first time. Then we opened the back doors.

About 90 of our 200 cupcakes were upside down.
Remember that speed rack I had bolted securely to the back of the truck? Turns out the rack wasn't the problem.
The trays could still slide right out of it. And the very back of a Sprinter van is apparently not the smoothest place to transport cupcakes.

Anyone who has ever ridden in the back of a school bus probably understands exactly what happened.
Lesson learned.

Welcome to Food Truck School.

After dealing with the cupcake disaster, we opened the serving window.

I think both Jill and I expected people to immediately understand what we were doing.

They didn’t.

There were plenty of people around.
But nobody knew what the heck we were.
People stopped and asked:

“Are you delivering?” “Are you selling these?”

You have to remember what St. Louis was like at that moment.
There really weren’t modern food trucks around yet. In fact we were one of the first trucks to hit the street along with PI Pizza who went out the week prior to us.

People weren't accustomed to seeing a brightly wrapped vehicle pull up, open a window and start selling food.

We ended up selling something like 20 cupcakes.
We gave away quite a few more.

Financially, it was not exactly a huge success.

But something else happened that day that I didn’t expect.
I was hooked.
I liked talking with the customers.
I liked watching people's faces when they saw all the beautifully decorated cupcakes. People smiled.

And strangely enough, I really enjoyed spending the day doing this with my sister. Who knew we would actually get along?

By the end of that first trip, I think both of us were charged up.
We hadn't made any money.

We had destroyed almost half our inventory.

We couldn't find a parking spot.

And most people didn't even understand what we were.

But we knew there was something there. We just had a lot to figure out.

Where were we going to park?

How were customers going to know where we were?

How were we going to keep cupcakes from flying around the truck?

And most importantly, how were we going to turn this strange experiment into an actual business?

Our first trip was officially behind us.
We didn't exactly have much money to deposit in the bank.
But hey — we knew it was going to take some time.
Now it was time to go back to our new hire and see when she wanted to take the truck out.

As it turned out, hiring Rachel would become one of the most important decisions we made.

Next Chapter: Rachel — The Face of Sarah’s Cake Stop

08/17/2026

Chapter 2: The Food Truck
Where was I going to find a food truck in the summer of 2010?

The food-truck era had not made its way to St. Louis yet. There were no clear regulations, no obvious people to call for advice, and I was not even completely sure what we needed.

At the most basic level, I thought we needed a vehicle that could transport fresh cupcakes from West County to downtown St. Louis. I figured a serving window would help, and probably air conditioning to keep the cupcakes cool.

I started searching eBay for 'food truck.' After about a week, I changed the search to 'Sprinter, Van' because I had decided a Sprinter-style van might be the right platform. Worst case, my brother and I could customize the van ourselves.

Then I found a 2004 Freightliner Sprinter that was not listed as a food truck at all, but it sure looked like one. It had two side serving windows, a stainless-steel rear area, three sinks plus a separate hand-washing sink, and a large generator.

I did not know enough yet to know exactly why all of those things mattered, but they looked good to me. It had a generator, which at the time I did not realize how big it was...HUGE!

The eBay auction ended without a bid, so I contacted the seller and made an offer below his reserve. He took it.

That is when the story started getting strange.

The man in Philadelphia was basically a dealer, I thought. He had already sold the truck to someone in California, but once that buyer found out what it would cost to ship the vehicle from Philadelphia to California, he decided to have the Philadelphia guy resell it.

So I was buying a truck from a man who technically did not own it, on behalf of a person in California I never met. The title, as I would learn, was sitting in escrow in Alabama.

This should probably have been the point where I walked away.

Instead, I went to the bank.

The Bank
I had a very good business relationship with my bank, and I usually dealt with the same person. I went in expecting to get a cashier's check from my own funds because I wanted to fly out later that day.

She asked why I was not financing the truck instead.

That sounded fine until she started asking normal bank questions.

What year, make, and model?

A 2004 Freightliner Sprinter.

What was the sale price?

That was a little harder to explain because a Blue Book value would make this look like an ordinary used delivery van, and this was anything but ordinary.

Then she asked for the VIN and the seller's name.

My answer was basically, 'Well, that's a funny story.'

Banks apparently do not love lending money on older vehicles that are physically in Philadelphia, being sold for someone in California, with a title sitting in Alabama, to a borrower who has never seen or driven the vehicle.

Somehow, in less than two hours, I walked out with a cashier's check for the full amount.

I bought a plane ticket to Philadelphia and flew out that night. Oh and I might have forgotten to inform my sister/partner I was heading to buy a van!

The Cab Driver
The next morning, a friend dropped me off downtown in Philadelphia and I hailed a cab to take me to the address where the truck was being stored.

As we got closer, the area became more industrial. There were fences with barbed wire, buses, truck garages and not much that looked welcoming.

The driver stopped outside an open gate, still a long walk from the building, and said, 'OK, you are here.'

I asked if he could drive me up to the building.

He looked at me like I had asked him to drive me to the moon.

Then he asked, 'Do you know them?'

I said, 'No, I am buying a van from them.'

He took his money and said something along the lines of, 'Be careful and good luck.'

I am not easily intimidated, but that made me pause.

Five Russian Guys Watching the World Cup:
I walked toward what looked like a greasy repair shop for buses and big trucks. There were tires, batteries and used-oil containers everywhere. There was no real office to walk into, so I entered through the garage.

I called out. Nobody answered.

From the back I could hear a television and what sounded like a game in playing.

I followed the sound and eventually found a small break room with five Russian men watching a World Cup match.

They all stopped and looked at me like I had walked into a sacred place.

So I did the one thing I knew might help: I started talking soccer and mentioned the team they were rooting for was not great on defense. I think they were watching Slovakia? Russia was not in the World Cup that year.

I had played soccer, followed the game closely and had been at the previous World Cup in Germany. I made a joke about their team and what they needed to do better.

They laughed.

Ice broken.

One of the men stood up and introduced himself. I wish I could remember his name. What I do remember is shaking his hand. His hands were dirty, and they were huge. Come to find out, he was a former professional handball player in Russia.

A Cupcake Truck?
He pulled the van out from between two big buses so I could look it over.

It was rough and needed a lot of cleaning, but for the most part it was what the pictures had shown. He explained it was a former coffee truck but did not know much more about it. He said he bought two big buses and the auction threw in the food truck van as a bundle. He really did not want it but he thought he could sell it.

The van started up and it ran beautifully.

A man from the neighboring garage walked over and asked what I planned to do with the van.

I said, 'A cupcake truck.'

Several of these big, brawny, greasy guys looked at me and laughed.

Then the neighboring mechanic pointed to the generator and told me, in broken English, that I did not need it. He offered to take it out immediately and pay me cash. BTW lots of cash!

I politely declined.

But his offer told me something important: if he wanted that generator that badly, and I knew what I had paid for the truck, I had probably gotten a very good deal.

California, Alabama and Kinko's, DMV:

The payment process was just as odd as everything else.

We had to go to a local Kinko's, put my cashier's check into a FedEx envelope and send it to the buyer in California. Once he received it, he would release the title being held in escrow in Alabama.

The arrangement existed because nobody completely trusted anybody else.

I cannot say I blamed them.

Once that was done, I realized I had another problem. I needed temporary tags if I was going to drive this thing more than 900 miles back to St. Louis.

I asked about temp tags, and my new Russian friend, not happy at this point, agreed to take me to the local DMV. It gave me a chance to drive the van and he road along with me.

The DMV
It was around noon on a Saturday and the DMV was packed. It was an odd DMV. We were in city residential area with small city homes but on the corner was a commercial building and the DMV.

We walked in this crowded building, and I immediately took a number. They were serving number 20. My number was around 72. I thought, this is going to take all afternoon.

I turned to show him the ticket and realized he was already walking through the crowd toward the counter.

He then lifted the counter flap, walked behind the desk, went down a hallway and into an office.

Not knowing what to do decided to follow him because at that point I had no idea what was going on.

He sat down at a computer, filled out a temporary tag form, hit print, picked up the paper, and handed it to me.

"Here is your tag."

As we walked back through the crowd, people started greeting him and shaking his hand. Some almost seemed to bow their heads. I felt like I was walking behind a local celebrity.

When we got back to the van, I looked at him and asked, 'What was that? Do you have family who work there?' I was thinking WTH!. He looked at me with a smirk and said,

"They like me there."

I did not ask another question.

I drove him back to the garage, said goodbye and started the 900-plus-mile drive to St. Louis.

I finally got out of Philadelphia around 1 p.m. and drove straight back, stopping only for gas and food.

The entire experience was so strange that I wrote it all down the very next day because I knew I would forget details - and I also knew nobody would believe the story later if I had not documented it. The picture below I took while checking the van out!

08/15/2026

Chapter 1 — How It All Started

Before Sarah’s Cake Stop was a pink truck full of cupcakes, it was a phone call.

January 2010. I’m at my office when my sister Jill calls. Normally, when Jill calls me during the day, it’s to fix her computer or remind me about some family thing I forgot about. Fair enough — I probably needed the reminders.

But this time was different.
She made small talk first, which was very unlike her, and then finally just said it:
“Jeff, I have an idea.”
She’d just gotten back from a trip out East and had seen a food truck selling cupcakes. At the time, Jill was running a small café and growing the bakery side of the business. Cupcakes, pastries, and wedding cakes were becoming a real business of their own.
Her idea: What if she did the same thing here in St. Louis, using the bakery — Sarah’s Cake Shop — as the home base?

I told her I thought it was a good idea.

What I meant was:
Good idea. Just not with me involved.

Here’s the thing about our family: my mom and dad owned a small, successful restaurant here in Fenton, MO , and the entrepreneurial streak runs pretty deep in all three kids. I owned a software company, Jill owned a café/bakery and our younger brother owns a successful home improvement company.

So when my sister and brother would call pitching me business ideas — which they did and still do regularly — I usually poke holes in them and tell them to focus on the businesses they already have.

We’re all business owners.
We don’t need more distractions.
But something about this idea was different.

Two days later, Jill called again. This time she had more than an idea.
She had a semi-pitch.
She asked if I’d be involved.
I said it again:
Great idea. Not with me involved.
Truthfully, I couldn’t picture being in business with my sister.
Still, I couldn’t let the idea go as much as I did not want to get involved.

I started researching food trucks on my own.
I found a cupcake truck in Washington, D.C. that was selling more than 500 cupcakes a day at about $4 each. I picked up the phone and called the guy. He was an attorney that decided cupcakes was his next logical career step...crazy who would do that?? But he seemed happy and was making money.
I did the math.
That was real money.
And yet, I already had a business partner in my software company. I didn’t need another one.

A week or so later came another call.
But this time, something had changed with me.
I was the one doing a lot of the talking — discussing how the business could be structured, how it would make money, and how we might operate it day to day.

All while still telling Jill I did not need to be involved. (Notice the slight change)

Then she told me she didn’t have the money to get the idea off the ground. She had just expanded her business and money at that time was tight (2010)

That’s where I came in.
I finally agreed — with conditions of course.
I made a list.
Things I would do:
• Research and buy the truck — and fund it
• Handle licensing and get the business set up
• Run the accounting and financial side
• Help with marketing — figure out social media, build a website, the works
Things I would not do:
• Work day-to-day operations
• Ever drive or work on the truck
• Make cupcakes
Spoiler:
I broke every single one of those rules. Over and over and over again.

But that was the plan.
We had an idea. We had a partnership. We would run it as a separate company but keep the name Sarah’s
And, at least on paper, we knew exactly what my role was going to be.

Now we just needed one small thing.
A food truck or van.

The problem was, this was 2010 in St. Louis.
We had absolutely no idea where to find one. We had no idea what to look for.

What happened next — an eBay listing, a flight to Philadelphia, a truck nobody seemed to actually own, five Russian (mob?!?) guys watching the World Cup, and one of the strangest trips to a DMV I’ve ever experienced — became one of the most memorable stories of the entire ten-year run.

That’s Chapter 2.

08/12/2026

Who wants "SARAH’S CAKE STOP — THE STORY BEHIND THE TRUCK"?

08/12/2026

Believe it or not, this is where Sarah’s Cake Stop started…back in 2010

01/20/2026