Hey, Pineapple here. 🍍
We need to talk about the $20 T-shirt.
Actually...
Can we make it $19.99?
I know. It's one penny. 😂
But whether we like it or not, pricing is a mental game. Your customer sees the 19 before they see the 20. There's a reason stores have been using prices like $19.99, $24.99 and $29.99 forever.
So, is $19.99 a good price for a shirt?
It can be.
Is $24.99 too much?
Not necessarily.
Could $14.99 make more sense?
Absolutely.
It depends on your product, your customer, your following, your costs and—this is the part I think small businesses sometimes overlook—the value of the brand you've built around that shirt.
Before we figure out what you should charge, though, there's an even more important question:
Do you actually know what you're making on it?
Because selling a lot of shirts and making money selling shirts are two very different things.
A Shirt Is Just a Shirt… Until It Isn't
Back in my Fresh Squeezed Threads days—yes, Pineapple had a clothing company. 🍍😎—we learned something pretty quickly:
We didn't want to just sell shirts.
We wanted to build a brand.
There's a difference.
We spent time sourcing quality blanks. We added our own branded labels inside the shirts. We had custom packaging with our logo. We paid attention to how the product looked and felt when someone opened their order.
Those little details helped take something ordinary and make it feel like it belonged to Fresh Squeezed Threads.
And that's important.
Think about the brands you buy from.
When you walk into a store you like and see a shirt for $24.99, are you standing there calculating what the company paid for the blank?
Probably not.
You're thinking:
That's a cool shirt.
You recognize the brand. You trust the quality. You like the design. You like the style. Maybe you even like what wearing that brand says about you.
That's the part I love about branding.
People like feeling like they're part of something.
A brand.
A culture.
A style.
And you don't have to be some giant company to create that feeling.
Small businesses can do it too.
Now, before Pineapple convinces you to order 5,000 custom bags and start sewing labels into everything you own, slow down. 😂
You don't need all of that on day one.
Start with what matters most:
A quality product and fun, relatable designs that connect with your specific target market.
Then build the experience around it as your business grows.
Let's Talk About the Money
Okay, let's say you're selling a single-sided shirt for $19.99.
Maybe your blank costs:
$4.00
And your DTF transfer costs:
$2.50
So you do some quick math:
$19.99 - $6.50 = $13.49
Looks pretty good, right?
Not so fast.
There's somebody missing from that equation.
You.
One of the biggest costs I see small-business owners forget is their own time.
Someone had to communicate with the customer.
Someone dealt with the artwork.
Someone built the gang sheet.
Someone ordered the blank.
Someone pressed the shirt.
Someone packaged it.
Someone got the order to the customer.
And if you're running a small business, there's a pretty good chance that someone was you.
Your time isn't suddenly free because you own the company.
Then there are all the other little expenses that like to sneak into a business: payment-processing fees, website costs, packaging, inventory, equipment, depreciation on your press, damaged products, mistakes and general overhead.
I'm not telling you to make this so complicated that you need a calculator every time somebody asks for a medium.
But I am telling you this:
🍍 PINEAPPLE RULE #1
Know your numbers before you quote the job.
You decide what margin makes sense.
It's your business.
There isn't one magical percentage that's right for every company.
But you need to know what your margin is.
There's a huge difference between knowingly accepting a smaller margin because there's a strategic reason to do it and accidentally working for almost nothing because you never did the math.
Don't Win the Order and Lose the Business
This is where things get tricky when you're starting out.
You want customers.
Someone asks for a quote and you really want that order, so you knock a couple dollars off.
Then maybe a couple more.
Eventually you win the job.
Feels good!
Until they come back.
Because now that first price has become their benchmark.
If you charged $10 last time and suddenly realize you really need to be at $14.99 or $19.99, the customer may not know you underpriced the first order.
All they know is:
“Wow. Your prices went up.”
That's why I believe in trying to build your pricing correctly from the beginning.
That doesn't mean being expensive just because you can.
Don't be excessive.
It means understanding your costs, valuing your time and leaving enough room for the business to operate.
“But I Found Someone Selling Shirts for $9.99!”
Ahhh...
The $9.99 shirt.
They're out there.
And you know what?
That's okay.
There is a market of customers for everyone.
Someone shopping for the absolute lowest price may not be looking for the same things as someone who cares about great service, quality, presentation and buying from a brand they enjoy.
That's an important distinction.
If your entire business strategy is being cheaper than everybody else, you're going to spend a lot of time chasing your tail.
They're at $12.
You go $9.99.
Someone else goes $8.99.
Then what?
$7.99?
At some point, everybody is working harder while making less.
Instead of constantly asking:
“How can I be cheaper?”
I want you asking:
“How am I amazing my customers?”
That's a question you can build a business around.
Being the Cheapest Also Takes Away One of Your Best Tools
Let's go back to our $19.99 shirt.
You've done the math.
Your costs work.
Your margin works.
Your customer is getting a great product.
Now let's say you want to create some excitement next week.
You can run:
🔥 THIS WEEK ONLY
$19.99 $14.99
Now you've created urgency.
There's a reason for the customer to buy today.
They're getting something they normally would have paid $19.99 for at $14.99.
That's a real promotion.
But if $9.99 is already the absolute lowest amount you can charge every single day...
Where do you go when you want to have a sale?
🍍 PINEAPPLE TIP
If you're already cheap every day, why does your customer need to buy today?
Having healthy margin gives you control.
You decide when you want to discount.
You're not forced to be permanently discounted.
Discounts Aren't Bad
Now don't get Pineapple wrong.
I love a good deal. 😂
I've discounted plenty of things.
There have even been times when I've done something for free because I knew there was a potentially massive customer relationship on the other side.
That's okay.
Because it was intentional.
If I choose to do that, I want the customer to know:
“We're taking care of this one for you.”
Or:
“This is a new-customer discount.”
There's a reason for it.
The customer understands they're receiving something of value instead of assuming that free or deeply discounted price is your normal price.
Volume matters too.
Someone buying one shirt and someone buying 100 shirts aren't necessarily going to have the same pricing.
The more they buy, the more flexibility you may have.
But there's that word again:
Margin.
You can't confidently decide how much to discount if you don't know how much you're making in the first place.
“Pineapple… I Think I've Been Charging Way Too Little.”
Okay.
First...
Don't panic.
And please don't finish this article, run to your website and randomly double every price. 😂
Start with your numbers.
Let's say you're selling a shirt for $10–$12 and you're busy, but you're wondering why there's never much money left.
Don't only look at your selling price.
Look at your costs too.
Maybe you're currently paying around $6 for your blank.
Could you eventually get that closer to $4 by finding vendors that work with resellers and negotiating better pricing?
Maybe you're effectively spending $5 per transfer.
Could smarter ordering or using a gang-sheet builder bring that closer to $2.50?
Maybe you haven't been accounting for $2 of your own labor.
Now we're starting to see what the shirt actually costs.
Then look at the selling price.
Maybe $10 becomes $14.99.
Maybe as the brand and value grow, it eventually becomes $19.99.
Or maybe your particular market tells you something completely different.
That's okay.
Don't copy Pineapple's number. Understand your number.
Once you've built healthy room between your real costs and your selling price, you suddenly have options.
You can have a sale.
You can give a volume discount.
You can reward a great customer.
You can fix a mistake without the entire order becoming a loss.
And yes...
You can actually get paid for the work you're doing.
Don't Let Growth Bully You Into Growing
While we're talking about costs, there's another trap I want to mention.
Overbuying inventory.
This doesn't only happen in the shirt business. It happens in almost every small business.
Things start going well.
Sales are growing.
And suddenly you think:
We're growing! We need more everything!
More blanks.
More colors.
More sizes.
More equipment.
More products.
Maybe more space.
Slow down, Pineapple Jr.
Don't let the market push you into something your business isn't ready for.
Having $10,000 worth of inventory doesn't automatically mean you've grown your business by $10,000.
Sometimes it means you have $10,000 sitting on a shelf.
Minimizing unnecessary overhead while you're growing can be incredibly important.
Let the business become ready for the next step before you force it into the next step.
And when you're considering meaningful financial changes, talk with your CPA or financial professional and make sure your business can actually handle them.
Growth is exciting.
Sustainable growth is better.
Pineapple Is Getting Serious for a Minute
We've talked about pricing.
We've talked about margins.
We've talked about branding, discounts, inventory and costs.
But none of those are number one on my list.
This is:
Customer service.
They chose you.
Remember that.
Out of all the businesses they could have purchased from, they decided to spend their money with you.
Maybe they liked your design.
Maybe they liked your brand.
Maybe somebody recommended you.
Maybe they just liked you.
Whatever the reason, they chose you.
Treat that decision like it matters.
If they have an issue, take care of them.
If something goes wrong, move heaven and earth to resolve it.
Treat your customers like family.
A competitor can find the same blank you use.
They can buy a similar transfer.
They can lower their price.
They can copy a promotion.
What they can't automatically copy is how you make your customers feel when they do business with you.
That's one of the greatest advantages a small business has.
Use it.
🍍 So… Are You Actually Making Money on That $20 Shirt?
I don't know.
And that's kind of the point.
Maybe $14.99 is right for your business.
Maybe it's $19.99.
Maybe you've created a brand and following where $24.99 makes perfect sense.
There isn't one number that works for everybody.
What matters is understanding why you're charging what you're charging.
Know your costs.
Know your margin.
Value your time.
Create designs your target customer actually wants.
Build a brand people enjoy being part of.
Don't let the cheapest competitor decide what your business becomes.
Give yourself room to run promotions.
Use discounts strategically.
Don't grow your overhead faster than your business.
And most importantly:
Take ridiculously good care of your customers.
Because I don't want your customer's first reaction to be:
“Wow, that was cheap.”
I'd much rather have them say:
“Wow. That was worth it.”
Build that kind of business.
The money has a much better chance of following.
— Pineapple 🍍
🍍 NOW IT'S YOUR TURN — ASK PINEAPPLE
Got a question about DTF, UV, pricing, sourcing, customers, marketing, margins or growing your small business?
Send it our way.
We're not here to pretend Pineapple knows everything. We're here to share real experience, talk about what has worked, talk about what hasn't, and hopefully help you avoid a few mistakes along the way.