by Jorie Jacobi
Published June 25, 2014

Jorie Jacobi is a twentysomething writer, artist, blogger and St. Louis native. Endlessly fascinated by people, she writes and tells stories as a knee-jerk reaction to being alive. She constantly finds herself in awe of St. Louis and the people here who make it such a beautiful, inspiring place.

How Do Friends Maintain A Business Worth Millions?

The Arch appears dizzyingly close on the 20th floor of the Gateway Tower, almost as close as you can get at this altitude, unless you’re BASE jumping. ShipWorks, a multimillion-dollar software company, shares the building with KMOV at One Memorial Drive. The office is a modern art masterpiece: large windows filter in natural light, looking out on the glassy, smooth surface of the river. Brian Nottingham and Wes Clayton, co-CEO’s of the company, have been friends since their freshman year at St. Louis University in 1997, when they were placed just a few doors down from each other in Clemens Hall. ShipWorks automates shipping information for online retailers, enabling them to easily send out large quantities of merchandise to customers. Brian and Wes developed the idea in their early twenties, and without it, retailers would have to manually input shipping information for every individual customer.

“I can’t imagine having done this any other way outside of a great friendship that turned into a business partnership,” says Brian, sitting at a table in an elegantly styled conference room. Wes listens. He wears a sharp button-down shirt, jeans, and a wedding ring, sipping coffee from a Starbucks-emblazoned paper cup. His office is clean and orderly, a sanctuary where he retreats post-interview. Brian’s has the nostalgic feel of a teenager’s room–a curated array of neon-colored nerf guns inhabits almost a full quadrant of the floor. “He steals all the darts and will randomly start shooting people, and we can’t retaliate,” jokes an employee, clad in a telephone headset. Pointing to a large photograph of what appears to be himself dressed in an elegant suit, Brian says, “That’s actually my face photoshopped onto Justin Timberlake’s body–it was a gift from the office. Everyone should have a pseudo-obsession with Justin Timberlake.”
“You can make that the pull quote,” Wes responds.

ShipWorks_Brainstorming Area

The men bonded over a mutual love of technology and video games years ago when they were teenagers. “Brian’s dorm room had all the fun stuff in it–we played a lot of James Bond and Jet Moto,” says Wes, remembering when Brian would show him games he’d coded on his graphing calculator. “I don’t even know what we had–Tetris, Blackjack … ” Brian continues. He would reinvent the games and play them in class, while pretending to be working on a problem. “You could be in class and nobody would know the difference … at that time, there were no iPhones, iPads, iPods, or any of that stuff. So if you wanted to not pay attention in class, there weren’t a lot of options.” Today, their office contains a Wizard of Oz digital pinball machine and the latest video gaming consoles amidst the modern trappings of what one might expect from a formidable company. It’s a drastic change from what they grew up with in college. “For campus email, if you didn’t have a computer, you had to walk down to the lobby and use these green screen BT100 terminals to check your email. Times have certainly changed,” says Wes.

They worked on their first project together while still in undergrad–a website feature for The Pasta House Co., Wes’s first web development client. The restaurant chain needed to simplify a mechanism on their website that managed restaurant locations, and Wes had built a prototype, but hit a wall soon after. “Ultimately, it was well beyond my capability at the time,” he says. He enlisted Brian’s help, and showed him his initial work. “Two weeks later, we had this full-blown C++ application that was just wickedly amazing, and solved all my customer’s needs,” says Wes. It was clear they worked well as a team, and began working on subsequent projects together. “That’s one thing we’ve always had from the beginning: trust, and the importance of personal well-being, and having that be important to you–someone else’s personal well-being,” says Brian. “There’s no keeping score.”

Brian took on a variety of other technology-related positions, which gave him experience that would later prove indispensable. “And then Wes just ate a lot of Ramen noodles,” Brian jokes. “I did,” Wes corroborates. Originally from St. Louis, Wes moved back in with his parents after college and started an office out of their basement, gathering funds from client work to invest in computer purchases for the business with Brian.


Brian moved out to Phoenix after college, “really for no purpose other than to see something different,” he says, calling it a “throw-a-dart-at-a-map situation.” He became business partners with Wes soon after. “That was fall of 2001,” he says. Eventually, family brought him back to the Midwest. “It had run its course. It was just time–you get the gut feeling. Nothing really negative or positive. It was just time.” While they were in different parts of the country, they still worked remotely on their business plan, primarily over instant messaging. “It’s funny, we always talk about that remote relationship and for whatever reason, maybe it’s having a great friendship as a baseline, it almost felt like we were in the same room. We developed such a tight relationship it almost felt like we were in the same place,” says Wes. “If one of us ever thought they needed to do something–move to Phoenix, or whatever it was–we thought, ‘We’ll figure it out. We’ll figure it out,’” says Wes.

“When we started, we knew we wanted to go into business, but didn’t know what we were going to do. We wanted to grow big, but do it slowly, methodically,” says Brian. “We haven’t made big decisions that would give us some kind of jump or instant leap that may be a negative in the long run.” The business partnership crystallized before the idea of what ShipWorks would eventually become–and while building an ambitious idea with a friend can be perilous, more than a decade later, they still work well together. “It’s always been a natural relationship. We’re very lucky in that way. We don’t always agree, but we disagree very respectfully … my background is more in technology and Wes’s is more in business, but we both have overlapping skillsets,” says Brian. When they do disagree, “we just do it my way,” Wes deadpans, before offering a serious answer. “I think we try to do what’s right–the right decision, whether it’s right for the business, right for our team, right for our customers. Ultimately, we just try to determine what the right thing to do is,” says Wes.


Their work with The Pasta House Co. led to eCommerce development for a local menswear supply company, Boxers, on Washington Avenue. As Boxers expanded to the eCommerce space, the company confronted many difficulties selling products online and shipping out orders efficiently. While developing a software solution, it dawned on Wes and Brian that Boxers couldn’t be the only retailer struggling with shipping. “We said, ‘Really, what we have here is a shipping application for the eCommerce space.’ That’s when we renamed the company ShipWorks,” says Brian. They realized they had a potential service that could be invaluable to online retailers, shipping companies and large online marketplaces–so the next step was to build partnerships linking up online businesses with shipping companies. This necessitated the unglamorous task of persistently asking shipping companies and online retailers if they’d allow ShipWorks to integrate with their services, which ultimately paid off, and resulted in several high-profile partnerships.

In the very early stages, when ShipWorks was still a two-person virtual operation, they got their first affirmation from none other than UPS. “I’ll never forget that day,” says Wes. He was on vacation at the time, traveling to Gulf Shores, Alabama, when he got a call from Brian. “He said, ‘Wes, you’ll never believe it–UPS finally said that we can integrate their technology into our application.’ That was just such a big deal at the time,” Wes recounts. There are still barriers to entry today for applications looking to integrate with large companies, but in the early 2000’s, it seemed borderline impossible. “Back then it felt like, ‘Maybe we’ll never get access to UPS.’ But that was one of those pivotal moments, I think, in the history of our business,” says Wes. “It validated what we we’d been doing. Those encouragements keep you going,” Brian agrees. “Yeah, absolutely,” Wes replies.

For online retailers, this capability can be the windfall that allows them to stay competitive with larger businesses. “ShipWorks gives you one central place to look at your orders, print all your shipping labels, and automate everything,” Brian explains. The software downloads orders from online retailers who use services like Amazon, eBay, and Etsy, and allows them to automate shipping orders to quickly send items to consumers, reducing necessary time and manpower. Matt Kubancik of Street Moda, an online retailer selling designer merchandise at reduced prices, explains it in practical terms–without ShipWorks, Kubancik’s team would have to manually print and enter shipping orders for each individual customer. For small merchants, the time, energy, and labor this costs can be detrimental, especially when shipping out 600 to 1,000 packages per day. “We’re able to automate much of that–so somebody on the shipping line can simply press a print button,” says Kubancik.


When Brian and Wes started ShipWorks in the early 2000’s, resources for young St. Louis entrepreneurs weren’t as robust as they are today. Wes and Brian were entirely self-funded and relied upon slow, methodical growth, accepting no venture capital or seed funding.
“We took no funding, no venture capital– just a lot of hard work,” says Wes.
“We did not know what we were doing–”
“–a lot of hard work, effort, and a long time before we started taking any paychecks from the business,” Wes continues. “There certainly have been a lot of naysayers along the way. I think that in some way, that was actually, at least for me, partially a driving force … not listening to those people, and figuring out what we were going to do to get over those many hurdles.” ShipWorks has now built relationships with eBay, Etsy, Amazon, Yahoo!Stores, FedEx, USPS, UPS, and DHL Global Mail. Businesses can quickly and easily automate shipping information for customers anywhere in the world.

Typically they grapple with business plans, API’s, and computer languages–but today they’re more reflective. “I think there’s probably a variety of answers–once you boil it all down, it comes back to trust,” says Brian. “Being able to trust that you can talk about stupid ambitions without being judged, being able to trust that you can own up to mistakes and move forward from them.” A pause. “I think that was a very fair assessment of friendship,” Wes agrees.

For more information about ShipWorks, visit www.shipworks.com.

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That’s one thing we’ve always had from the beginning: trust. ”

– Brian Nottingham

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