Sheldon started a company in 2008 as a side project. He was working full-time at a design firm in Vermont, not making much money and not having much to do thanks to the ongoing recession. Since college, he’d enjoyed entering T-shirt design contests hosted by companies like Threadless, Woot, and DesignByHumans and eventually started to win them. “You’d get, like, $500, and they send you five of the shirts.” In college, this felt like a fair trade, but as Sheldon started to win more often and enter the working world, he realized he was getting the short end of the stick. “They owned all the rights to my artwork,” he says, “and they’re printing five, 10, 15,000 of these shirts, and they’re making all the money. And I’m sitting here with a $500 check.”

Confident that people liked his designs, Sheldon decided to start selling the shirts himself. He borrowed $2,000 from his dad, set up a store on the Big Cartel platform, drew up some new designs in his trademark minimalistic style, printed them onto 200 American Apparel T-shirts, and started posting his stuff in forums and online. He named his shop Ugmonk — a meaningless word that Sheldon doesn’t want to explain because he’s worried people will be disappointed with how boring the story is — mostly because he didn’t want to call it something like “Jeff’s T-Shirt Designs.” He and his wife did most of the shipping, and much of the inventory lived in his parents’ basement.

In 2017, Sheldon decided to take a bigger swing and design a product from scratch. He wanted a place to put his phone, a home for his pens, just a simple organizer to stick behind his keyboard. So he designed a small, modular set, named it Gather, and launched a Kickstarter campaign. Sheldon hoped to get about $18,000 in preorders through the campaign and instead ended up with $430,960. It was a big enough deal that the Shark Tank producers called, he says, though Sheldon had to turn them down since he hadn’t actually made the product yet.

At the time, this seemed like a good problem to have. Sheldon even launched Gather as a separate brand on a separate website, thinking it might be bigger than Ugmonk and could ultimately replace it. He thought Gather might end up in Target. This was going to be huge.

Eager to fill all those orders and capitalize on the interest in Gather, Sheldon turned to a company in Texas that had a factory in China. And he quickly discovered exactly how it works to make products at scale. “We were injection-molding the parts,” he says, “which means the parts cost less than $1, but the molds cost between $20,000 and $30,000.” That meant no small batches, no experiments, only giant orders. The factory in China had never worked with wood before, it turned out, and the first models that came back were warped and wonky and generally nowhere near Sheldon’s standards. So he gave feedback to his contact in Texas, who took that feedback to China, and weeks later, more products showed up at his door. Rinse and repeat, over and over. For months.

Even after all the back and forth, Sheldon estimates now that 30 percent of the products he shipped to Kickstarter backers ultimately had to be replaced. Most users actually liked the product, and he eventually sold out his inventory, but too much of it just wasn’t up to Sheldon’s standards. He thought more than once about just scrapping the whole idea. “I was so disconnected from the process,” he says now. “I didn’t go to the factory, and I should have. I wasn’t the person communicating. I would just wait for photos or prototypes to show up at my house.” He decided, right then and there, that he didn’t want to be a big Target brand if this was what it took.

Even that was harder than it sounded, though. With his next product, a paper-based productivity system called Analog, another Kickstarter hit, Sheldon resolved to think smaller and more locally. He contracted with a printer in Indiana for the cards, hoping working domestically would help. It didn’t. There were just too many orders, and the quality suffered as a result. Sheldon had to throw away most of what was produced — though he kept a few of the failures as a reminder of how things really work. But then, through a friend, Sheldon got connected to a woodworker down the road in Pennsylvania who grew up working for his Amish father’s furniture business and eventually started his own. “They bailed us out of the Analog Kickstarter by replacing all the bad ones,” Sheldon says, “and got us connected to the Amish and Mennonite communities.”

Analog is now Ugmonk’s biggest product — Sheldon says it accounts for about 80 percent of Ugmonk’s sales. But he never stopped thinking about Gather. He still wanted to design desk accessories and had lots of ideas for new components. He found an industrial designer, Jack Marple, who agreed to help him figure out how to design and manufacture desk accessories in a more local, more predictable, higher-end way. They started sending 3D-printed prototypes back and forth and began reaching out to more local shops and fabricators.

They ultimately built a local supply chain, made up of largely Mennonite and Amish manufacturers, who they hoped could make Gather at a much higher quality. But getting up and running took a huge amount of work. A Mennonite-run company that mostly does metalwork for dairy farms agreed to be one of Ugmonk’s suppliers, for instance, but only after some convincing. “They’re making cattle chutes and plow pieces,” Sheldon says, “and I tell them it’s a stand for an iPhone… they still have flip phones.” But once Sheldon told them about the quality and craftsmanship he was looking for, they were in.

Over the last couple of years, Sheldon and his team — which was, for a long time, mostly Sheldon’s wife and family but now includes five part-time helpers and Tim Fortney, who became Ugmonk’s second full-time employee earlier this year — have spent countless hours driving between factories and warehouses, looking at prototypes and endlessly refining the Gather products.