This side gig became a $5 million online lifestyle brand by focusing on community

When Jeff Sheldon printed his first run of 200 screen-printed shirts, he had no idea that this small entrepreneurial experiment would be the first step in building a multi-million dollar cult lifestyle brand. Fresh out of college and working a full-time design job, the idea for Ugmonk stemmed from Sheldon’s search for high-quality, aesthetically modern items that meshed with love for typography and minimalist design.

Starting with a limited run of four different designs, Sheldon’s t-shirts ended up featured on a handful of blogs about clothing and design and sold out faster than he expected. With the successful experiment under his belt, Sheldon decided to make Ugmonk his side gig. For the first two years it stayed that way. Sheldon worked nights and weekends offering new limited t-shirt runs and started thinking about how he could take the business full time.

During that time, Sheldon worked to define Ugmonk as a brand with a focus on high-quality, well-designed items. By making connections within the design and clothing community, partnering with manufacturers that shared his ideals, and creating a feeling of exclusivity for customers through limited production runs, Sheldon was able to make Ugmonk his full-time job in 2010.

By leaning on the community and business connections he made during those first two years, Sheldon took Ugmonk from a screen-printing side gig to an eCommerce lifestyle brand doing $5 million in annual revenue.

Build a cult following through personal relationships

You only become a cult brand if you build relationships with your customers. Connecting with like-minded individuals, whether it’s through blogging, social media, or email, is one of the best ways to build an engaged community. Ugmonk used social media and email marketing to amplify their brand, meet people with a similar aesthetic, and connect with customers directly.

These relationships are at the center of how Ugmonk grew from a side gig to a full-fledged lifestyle brand. During those first few side project years, Sheldon reached out to people he knew from college and online t-shirt forums. He used these forums as a place to promote his t-shirt designs as well as the Ugmonk brand.

Sheldon was essentially following the popular startup mantra “do things that don’t scale” before it was even coined. In 2013, Y Combinator founder Paul Graham famously wrote that startup founders should pursue growth tactics that wouldn’t easily scale in order to find initial traction. “A lot of would-be founders believe that startups either take off or don’t,” he wrote. “Actually startups take off because the founders make them take off.”

Graham counsels startup founders to go out and manually recruit customers at the outset, which is what Sheldon was doing by reconnecting with college buddies and actively participating in t-shirt forums. But more than that, he was laying the groundwork for a community that would sustain Ugmonk’s future growth and lay the seeds for the brand’s eventual image. By joining in the conversations that his customers were having and offering up his own insight, Sheldon, and by proxy Ugmonk, were positioning themselves as a brand with a mission.

As Ugmonk grew, this focus on fostering a community grew as well. Through his personal social media channels (which use the Ugmonk moniker), Sheldon not only promotes the Ugmonk brand, he uses it as a way to find out more about his customers’ preferences.

Ugmonk sketchbook poll via Twitter.

This is a great way to gauge customer interest in a new product or get feedback on a current one. The above post pulls triple duty for Ugmonk:

  • Sheldon and the brand foster a deeper connection with fans;
  • He gains valuable insight on his customers’ preferred brand sketchbook, a piece of data that could be useful for everything from marketing targeting to product development;
  • And he’s able to tease an upcoming product, which creates some initial buzz for a future release (so he won’t be starting at zero on launch day).

The comments on the Twitter thread go on to surface additional insights into the type of paper, design, and cost the customer is looking for—all useful data points for Ugmonk.

Strong community relationships are at the center of how Ugmonk grew from a side gig to a full-fledged lifestyle brand.

When you’ve built a community around a product that extends past promotion and sales, it’s easier to get buy-in for new projects as well. Ugmonk took to Kickstarter to fund Gather, a minimalist desk organization module that customers can build to their own specifications. Their customers pledged $430,960 against a goal of $18,000, giving Ugmonk the ability to produce an even better product than they anticipated. Lots of companies have turned to crowdsourcing in the recent past, and while this model does work well for most, it’s important to keep in mind what underpins that success: crowdsourcing is only as powerful as the community that exists to support it.

Ugmonk’s growth from limited runs of screen-printed t-shirts to a full-service lifestyle brand is the result of building a strong community from the outset. Not only does the community support the business as customers, they act as promoters of the brand. By connecting with these like-minded individuals, Ugmonk can create a wide range of products with the assurance that their customers will buy into the aesthetic Ugmonk is known for.

Ensure quality at scale with strategic partnerships

One of the core promises Ugmonk makes to customers is undeniably high quality products. Consumers know the look and feel immediately and associate it with quality construction and a recognizable design aesthetic. When someone buys from Ugmonk, they’re doing so with the knowledge that the product is the best it possibly can be.

Instead of producing everything in-house, potentially taking years to learn new trades and manufacturing methods, Ugmonk partners with brands that share their focus on quality. By outsourcing manufacturing for some of their products, Ugmonk is able to create more different types of products as well. This allows Ugmonk to focus on what they do best—the design.

These partnerships allow Ugmonk to provide the same level of quality as the business grows. The products they create, their website, content, and photography are all designed with an eye towards quality and the minimalist aesthetic. The time they save by letting experts tool their leather or fire their ceramic mugs is more time that Ugmonk can spend designing new products.

Design process example via Ugmonk.

Their partnerships strategy also helps Ugmonk from the promotional side of things. Each company they choose to work with has an audience that likely shares their design aesthetic. Ugmonk can amplify their message and potentially gain new customers through the right kind of partnerships. Furthermore, it gives their new products instant credibility. For example, by partnering with Ebbets Field Flannels for their hats, Ugmonk customers can instantly trust that they’re getting a quality product. The partnership gives Ugmonk access to another brand’s equity.

Taking a product from idea to implementation isn’t easy. From design and prototyping to manufacturing, quality control, and shipping, companies need to have their hands in a number of different logistical operations. By offloading some of the manufacturing to like-minded companies that are experts in the field, Ugmonk can stay true to their mission of quality and minimal design.

Use exclusivity to boost customer engagement

The first item Ugmonk produced was a limited run of screen-printed t-shirts. It was, by definition, an exclusive offer. That idea of exclusivity informed how Sheldon built Ugmonk into the lifestyle brand it is today. The definition of exclusive has changed over time, but they are still offering limited 200 item runs to celebrate their recent anniversary. This taps into the customer’s need to be a part of a special group and keeps them coming back for more.

Ugmonk Tenth Anniversary Set via Instagram.

Offering an exclusive product also aligns with Ugmonk’s positioning as a high-quality design brand. Often associated with luxury brands, the idea that quality and exclusivity both increase the perceived value of a product is working in Ugmonk’s favor as well. They’re taking an engaged community and building it into a highly engaged cult followingKevin Kelly calls these customers True Fans and says you only need a thousand to be a successful creator:

“Instead of trying to reach the narrow and unlikely peaks of platinum bestseller hits, blockbusters, and celebrity status, you can aim for direct connection with a thousand true fans. On your way, no matter how many fans you actually succeed in gaining, you’ll be surrounded not by faddish infatuation, but by genuine and true appreciation.”

It’s this genuine appreciation from customers that really helps elevate brands to a different level. Customers purchasing from a lifestyle brand like Ugmonk aren’t just looking for utility; they want an item that shows off their personality and status. When a company can tap into these feelings, as Ugmonk has done, customers will move closer to True Fan territory. Customers will act as social proof by sharing purchases on social media as well as with their friends and family. This helps increase awareness of the Ugmonk brand.

Key takeaways

► Foster real relationships

Ugmonk started out as a one-person business and a decade later is just a few employees larger. But Ugmonk punches above its weight because of its dedicated community of engaged customers. Without a community of like-minded individuals to amplify your message, it’s difficult to build a brand that taps into a larger audience. Use one-to-one relationships with your customer to make stronger connections and boost engagement.

► Seek out beneficial partnerships

If Ugmonk had to manufacture every item in-house, Jeff Sheldon and his employees would need to learn a lot of specific skills very quickly. By partnering with companies that shared their design aesthetic and relentless focus on quality, Ugmonk was able to scale their product offering faster and offer more value to their customers.

► Focus on your True Fans

A large, apathetic audience isn’t as valuable as a smaller, engaged audience. When you’re growing your following, it’s important to focus on quality over quantity. When a customer is invested in your brand, they’re more likely to purchase again and talk about you to their network.

► Create a unified brand

Ugmonk products are always 100 percent on brand. From coffee cup to t-shirt or desk swag, everything fits into a clearly defined brand identity. Customers will be more willing to purchase different kinds of products when they fit into the existing aesthetic they expect from your brand.

► Participate in the community

Ugmonk shares a passion with their community. They join in conversations and are seen as a subject matter expert as a result. This doesn’t just help the perception of their brand, it helps amplify their message. Customers like buying from a brand they know is just as interested in something as they are.

Sam Hollis
Sam Hollis is a writer at Jilt. When he's not writing about high growth eCommerce startups, he likes to play the piano and cook. See more his writing at his Contently page.

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