Pirate Ship Review: Pros & Cons of This Cheap Shipping Service

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Shipping packages can be expensive and stressful with huge price tags, long lines and little guidance.

Enter Pirate Ship. The online shipping service secures some of the cheapest rates for its customers, bridging the gap between the price that Corporate America and Average Joe pay for shipping.

In this Pirate Ship review, I’ll tell you what Pirate Ship is, how it works and Team Clark’s experience with using the company.

Table of Contents

Pirate Ship Review: Quick Look

Company NamePirate Ship
Company TypeShipping for small businesses
Key FeaturesDiscounted rates via UPS and USPS
DownsidesNot the best rates for giant corporations or bulk shipping
Best ForIndividuals and small businesses

What Is Pirate Ship?

Founded in 2014 in Jackson, Wyoming, Pirate Ship markets itself as the cheapest shipping option for small businesses.

Pirate Ship aggregates its customers’ shipping volume, using it to secure cheap USPS and UPS shipping rates typically reserved for giant corporations.

With a Jolly Roger for a logo and a founder and CEO who goes by “Cap’n” Bjorn Borstelmann on LinkedIn, the company leans into its pirate branding. It goes so far as to train its customer service agents on how to talk like a pirate for two weeks. Borstelmann is on record saying he wanted to make shipping less boring.

“Who better than pirates to help you save your booty and have a fun time doing so as well?” Borstelmann said.

How Does Pirate Ship Work?

Screenshot via pirateship.com

Pirate Ship offers free membership (compared to the monthly fee of competitors such as Stamps.com). You can sign up by providing your email.

After comparing the UPS and USPS rates that Pirate Ship offers, you can create and print shipping labels from any computer. From there, you either avoid the lines and drop off your packages at a UPS or USPS facility or schedule a pickup.


The company claims it doesn’t add any markups or hidden fees and instead makes all its money through its partnerships with UPS and USPS.

Conveniently, Pirate Ship lets you create labels from a spreadsheet or import e-commerce orders from all the major platforms.

You can use your own packaging or buy your packaging from UPS or USPS. Once you’re signed in, Pirate Ship even provides you with a detailed pricing guide on what’s probably the best choice for you.

Who Should Use Pirate Ship?

Pirate Ship markets itself as an advocate for small business owners. According to company lore, Borstelmann originally started the shipping company because he couldn’t find a good solution for his own e-commerce business.

I can see how Pirate Ship may be fantastic for small business owners with little time and tight margins. But it’s fantastic for individuals as well.

“I don’t know how often you have to ship a package. It’s gotten really expensive. I feel so bad for postal workers. They are so stretched thin and they are frightfully overworked. They work in terrible conditions,” money expert Clark Howard says.

“If instead of standing in line at the postal service, you go to UPS or FedEx, it’s huge money to send something. I mean, it’s crazy. We want to send something across the country to our daughter. There are times that what we’re sending her costs less than what it costs to send the package.”

The company’s marketing materials also seem heavily slanted toward small businesses because presumably, if you’re a Fortune 500-sized company, you’re able to negotiate even better shipping rates from the biggest carriers than what Pirate Ship offers.

Most individuals and businesses don’t move that sort of daily volume.

Clark Howard’s Experience With Pirate Ship

Clark now uses Pirate Ship frequently to ship packages to one of his daughters in Los Angeles. Before, he was using FedEx through a discount program with his insurance company (USAA). He says he’s getting much better deals through Pirate Ship.


“In the case of Pirate Ship, generally depending on which UPS service you’re using, you’re going to save 50%-60% typically versus retail that UPS charges somebody who just walks in the door. This is really great stuff, how much money you can save.”

My Personal Experience Reviewing Pirate Ship

Screenshot via pirateship.com

I recently used Pirate Ship to send out 27 packages all over the country. At an average cost of $3.65, including less than $4 to Hawaii, my entire shipping bill came out to less than $100.

I typically find shipping to be incredibly frustrating — perhaps one notch below visiting the dentist on the dread meter.

What size box do I buy? And which is the cheapest, most appropriate option for postage? Is there time in my schedule to wait in line at the post office? And do I stand off to the side scribbling the name and address of my package recipient, or do I hurriedly write it out while in line or at the register?

Often I grab a bigger box than I need and ride with it, even if I accidentally select one of the more expensive postage options. There’s no one there to ask questions, and if I’ve guessed wrong, I don’t want to wait in line. Plus, if I’ve already sealed the package, I don’t want to pay for it, rip it open, throw it away and start over.

Using Pirate Ship alleviated almost all of those concerns. I still elected to take the packages to a USPS location. But after buying 100 poly mailers for $11.98 on the suggestion of my brother, who operates a small business selling sneakers, I was able to quickly create, print and tape on labels from home.

The Pirate Ship website and customer service offer plenty of resources to answer questions and secure the cheapest option. And I did most of the work well outside of business hours.

I was surprised that, even during a period of historically high inflation, I was able to ship one package to Hawaii for less than $4. Since all my packages were identical, I was also able to save and replicate all the information for all 27 mailing labels.

Where Pirate Ship Shines

Here are some of the biggest benefits to using Pirate Ship:

  • Huge shipping discounts for individuals and small businesses. If you’re walking into a USPS, UPS or FedEx store and paying market rates for shipping, you’re almost certainly going to get huge discounts by going through Pirate Ship instead.
  • Intuitive, simple website. Like a well-organized interstate with lots of exit signs, Pirate Ship guides you toward the right pages on the site seamlessly. I normally feel disoriented and confused when it comes to shipping. But I clicked on the first obvious navigation point and the site sort of ushered me along to the end.
  • No waiting in line. You know the feeling. You’re on your lunch break and you need to mail a Christmas present to your out-of-state sister and her kids. But when you get to a post office, you’re stuck in a slow-moving line behind a swarm of other people, waiting on two overworked, slow-moving workers at the registers. That’s all out the window when you use Pirate Ship.
  • Fun help if you need it. The pirate-themed branding, including the customer service agents’ lingo, is quirky and fun. But it’s also nice to have an organized, helpful team of people available via live chat or email to answer any questions you have.

Where Pirate Ship Falls Short

Here are some of the biggest downsides to using Pirate Ship:

  • Doesn’t work well for every niche. I read through dozens of reviews across at least five different platforms. Other than carrier (price) adjustments, which are made by UPS or USPS based on incorrect information such as size or weight, this is the most common complaint I found. Shipping is such a large category given all the variables for contents, package size and shape. Pirate Ship may not be the best for some specific needs, especially for extreme outliers.
  • Shipping in bulk can be annoying or inefficient. Some apparent customers have complained that converting huge spreadsheets of data, or importing data from an e-commerce website, hasn’t always worked smoothly. This seems to be an occasional issue for those shipping hundreds of packages or more every week.
  • Not the cheapest option for giant corporations. If you work for a billion-dollar company, you almost certainly will get better shipping rates by negotiating your own prices. It’s unclear at what level of volume Pirate Ship becomes less advantageous. But there’s a clear spectrum from tiny to enormous in terms of company size.
  • May not be the best option for international shipping. You can use Pirate Ship to send packages only from the United States. It also loses some of its competitive pricing edge if you’re sending something to another country, depending on which alternative you choose.

Final Thoughts

Sending packages via PirateShip is the cheapest and easiest process I’ve experienced. After discovering it recently, I’ll be a repeat customer. Clark loves the service as well.

It’s not the be-all, end-all for every package ever shipped in the United States. But if you’re an individual or small business, it very well may be the best option.

I didn’t set out to review Pirate Ship when I used it last month. But now that I’ve stumbled upon it, I’ll be recommending it privately to family and friends as well.

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