Question: What’s the best way to buy shipping labels? Answer: With y’er AYE-Phone!

At least that’s what Pirate Ship, Wyoming’s only pirate-infested shipping company, would have you believe. And it seems to have the numbers to back it up. Since its inception only five years ago, the company has already attracted “hundreds of thousands” of shippers – seemingly to the tune of a sea shanty promising a friction-free postage-buying experience with no hidden charges.

What plunder?

Cap’n Bjorn Borstelmann, a Wyoming native with a name that seems to fit squarely within the realm of pirate lore, started Pirate Ship with the goal of making shipping more enjoyable.

“Ultimately, who better than pirates to help you save your booty and have a fun time doing so, as well?” he said, indicating he aimed to make a more intuitive shipping product, too. “Everything was so boring – all cookie cutter – there was no pleasure in shipping at all. From a designer’s point of view, if you can make something enjoyable, you’ve got a better business.”

But Borstelmann wasn’t sure how people would react to their proudly waving Jolly Roger. Still, his startup walked the plank to go all in on its cheeky name and rascally style. They make no apologies about it to this day.

While the commitment to piracy could have sunk them right out of the shipyard, it’s instead helped them float further, faster. Since opening shop in 2014, the company has been pirating business from big names like and that process a landlubber’s share of shipping via the U.S. Postal Service.

The lure of these mammoth companies has always been passing on aggregate low-shipping rates only available to companies shipping large volumes. However, most companies offering access to the lowest rates also charge a subscription fee for the privilege. Both and, for instance, charge $17.99 per month on top of shipping fees.

“For all small micro businesses out there, that $20 a month is really meaningful – it can even change the ability to buy inventory that can make a business more successful,” Borstelmann said.

And it does add up. Over the course of a year, Borstelmann’s entrenched competitors rake in more than $200 from each subscriber. Pirate Ship is paradoxically uninterested in that extra golden plunder.

Which begs the question: Why pirates?

Livin’ la vida pirata

“We definitely live the pirate lifestyle,” said Borstelmann. “Everything here is pirate.”

Think tiki bars, internal pirate joke competitions, and even two weeks of training so customer support specialists can talk like a pirate.

Pirate Ship unapologetically embraces a full-time pirate schtick as it passes on the best commercial shipping rates available to its customers – along with plenty of corny pirate jokes and salty banter. The young company may be the only business expecting to be taken seriously that can get away with calling its customers “scurvy dogs” alongside more respectful greetings like, “Ahoy Cap’n!”

And instead of sign-offs like “respectfully,” “sincerely,” or “regards,” those getting emails from the captain of Pirate Ship get a simple “ARRrrrr” as goodbye.

It’s this committed behavior and pirate psyche that Bortselmann said has contributed to his company’s success.

“Some of the best brands in the world go as integrated as possible,” he said. “Disney doesn’t slap a logo on something and call it done; they build an experience.”

Even the company’s login screen integrates some pirate spice with a button proclaiming, “Yarrrr, log me in.” Borstelmann said he has a spreadsheet of pirate jokes that his software spits out randomly while it’s processing a batch of labels. And the company’s conference call system uses pirate speak to introduce its hold music featuring Caribbean steel drums.

Buried treasure

It’s not immediately apparent to an outsider how Pirate Ship makes money. The company doesn’t upcharge on the rates it gets from the Postal Service. And it has no subscription fee.

Buried in an FAQ without an “X” marking the spot, the company reveals to skeptics how it loots its hoard.

“The reality is we make our money just like any other shipping software company: through our official partnership with USPS,” the support article reads. “The big difference between us and our competitors is that we’ve used modern ideas to build a lean business that’s able to operate with our partnership income alone, so that we don’t have to charge our customers nickels and dimes on top like everyone else.”

Borstelmann added that the USPS gets a bad rap, but he doesn’t feel it’s deserved.

“I think it’s government done right,” he said, especially given the insane amount of infrastructure it takes to keep packages and mail showing up to 156 million delivery points six days a week.

However, the government does face limitations that are merely a passing swell to a pirate.

“Government isn’t great at innovating, so private-public partnerships fill a gap and help them stay cutting-edge,” Borstelmann said. “That’s really unique – it’s not replicated anywhere else in the world.”

Where mail has been privatized in other places, Borstelmann said shippers jack up prices for profit. But the U.S. has kept it public, allowing even startups to get affordable shipping options. This, he added, shows how the U.S. has embraced entrepreneurs much more than other countries.

And that’s exactly the demographic Pirate Ship serves.

Building the Ship

In July 2017, Cody Hamilton opened Pine Coffee Supply, a specialty coffee shop and roastery in Pinedale with the highest-quality coffees he could “source responsibly.”

Hamilton, like many other startups and small businesses, doesn’t ship a ton of boxes through the U.S. Postal Service. But even with about 20 shipments a month, he sends out enough that it could get annoying, make costs soar and even turn off his customers.

He found Pirate Ship organically through a web search for different software-based shipping solutions. He said he liked what he found. The lack of subscription fees made sense while he’s growing his business. And signing up with Pirate Ship qualified him, with his small business, to get shipping rates reserved only for businesses sending out 50,000 packages per month.

Borstelmann called this a “secret” shipping service that startups couldn’t otherwise access called Priority Mail Cubic. Instead of being based on the weight of a box, the service bases fees on the size of a box, meaning you can use your own packaging and get flat-rate pricing.

“Every Fortune 500 company had that contract,” he said, “But small business was getting cut out of the loop.”

And that means lost sales, in many instances. For Hamilton in Pinedale, he had been using flat rate shipping boxes that didn’t allow him to showcase his brand on the box. And it was expensive to the point that many people simply walked away from buying anything just because of high shipping costs.

With Pirate Ship, he said he saves nearly 50% on shipping, which he can pass along to his customers. Customers who no longer abandon their cart when they see the shipping costs.

“Pirate Ship eliminated that since we made the switch,” Hamilton said. “There’s no more shipping negativity.”

That negativity expands to the attitude Hamilton has while shipping. He said Pirate Ship’s interface is “super intuitive,” and that the branding and image are fun.

“It’s kinda nice when you’re doing work with the quirks of how they word things,” Hamilton said. “It takes off some of the stresses of everyday work. It feels like you’re using more of a Mac product than a PC product.”

While Hamilton wants to grow his online subscriptions and offerings in coming years, going from 20 boxes a month to 50,000 is daunting. But before he could ever offer the service to others, Borstelmann first had to build up to that quantity himself.

It helped that he was in a subscription box startup at the time called Conscious Box. The subscription sent organic products and natural product samples to subscribers every month who wanted to be more conscientious about buying choices. It was a way to introduce people to new brands and healthier alternatives, Borstelmann said.

The e-commerce business scaled quickly to 30,000 subscribers, giving them enough volume to be knocking at the Priority Mail Cubic door without embarrassing themselves.

“Shipping that many packages was really a nightmare,” he said. And making matters worse, there weren’t a lot of options on the market in terms of shipping software. And the ones there he called “complicated, expensive, hair-pulling-out tasks” that used opaque pricing models with markup and monthly fees.

“You had to install desktop apps and work your way through error messages,” he said. “There wasn’t a lot in terms of modern design thinking or user interface design consideration.”

But while those kinds of companies chased the big contracts with established shippers, Pirate Ship decided to turn its attention to companies like its own: those struggling to make things work where shipping costs can make a world of difference.

“We’re unique because we focus solely on the little guys,” Borstelmann said. “They need that helping hand. Shipping can make or break their business. It’s so cool to influence the success of somebody’s business and watch it take off – that’s really gratifying.”

Borstelmann created what he deemed a superior tool and started shopping it out to other startups through referrals and relationship marketing. Within about six months of exploration, they hit critical mass, threw up a landing page and started attracting customers and making profit “right away.”

Smooth sailing after a rocky history

Conscious Box fizzled due to a variety of factors, along with other startups Borstelmann founded, including Formalitees, which “plotted the destruction of the business suit (and the evils of business as usual)” with a patented tie T-shirt.

But Pirate Ship has been a different whale of a tale. In its five short years on the market, it’s experienced mostly smooth sailing. The company even became the lead sponsor for Pitch Day in Jackson Hole this past summer. The event is a Shark Tank-style offering that gives startups a chance to pitch their business to investors and a live audience with a chance to win cash prizes and mentoring.

For someone focused on the little guy, the partnership makes sense. Borstelmann himself was a ninth-grade dropout.

“The public education system isn’t for everybody,” he said. “Ultimately everybody’s got to find their own path.”

For him, that path was getting his Wyoming GED and going to the world’s leading advertising school in Germany at age 19, Miami Ad School.

“That was a really eye-opening and important experience in my life,” he said.

Since then, it’s been a string of startups and non sequiturs defining his life.

“I’ve shipped millions of packages, made the president of the United States say cupcakes are good for your health, made business suits obsolete, been hacked by the Sudan Electronic Army, started a million-dollar business from a bunk bed and ate Harrison Ford’s sandwich,” he said on his LinkedIn profile.

And all that translates into an independent company that’s now scaling up in Jackson. With a team of 26 pirates, he’s just purchased the Pirate Ship headquarters’ building in downtown Jackson, a block from Town Square.

“We’re bringing all the pirates home to roost in Jackson Hole,” Borstelmann said. “We’re testing the hypothesis that we can get the world’s best to relocate and enjoy life in the Tetons.”

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