"When the Side Project Becomes the Main Thing" with Connie Collingsworth
Connie Collingsworth returns to Adventures In Design with a major update on Happy Jack Hat Co. and the business looks very different from the one she originally imagined.
Happy Jack started because Connie couldn't find the hats she wanted while developing merchandise for Colter Wall. The original idea was simple: manufacture better blank hats and make them available to other creators. Instead, managers, bands, brands, and small businesses started coming directly to Connie asking her to create fully custom hats for them. Today she has upwards of 15 projects moving at once, ranging from 50-piece orders for small businesses to thousands of hats for touring musicians.
At the same time, Colter Wall stepping away from touring eliminated a piece of work Connie had relied on for nearly a decade. Rather than replacing that security with another job, Connie and Stacy decided to bet on themselves. That change gave Happy Jack room to grow and forced Connie to get even clearer about what she wants the company to be.
That includes ending a business partnership that was pulling Happy Jack away from its original vision. Connie doesn't want to become another company willing to manufacture any hat somebody asks for. She wants Happy Jack to have a recognizable point of view: specific silhouettes, materials, colors and details rooted in the working-class hats she remembers from her childhood.
We get deep into the business of customization, why making fewer styles can actually strengthen a brand, designing merchandise with profit margins in mind, and the difference between putting your logo on somebody else's blank and creating a product that actually belongs to your brand.
Connie also gives us a preview of Happy Jack's long-awaited new website and explains how the brand is being built around her father, his "Happy Jack" handle, coal-mining culture, and the hats worn by the men she grew up around. Even the new logos and promotional pieces are being designed to feel like artifacts that could have existed 50 years ago.
And then there's perhaps the biggest sign that this thing is getting serious: Connie and Stacy have moved the operation out of their house and into their first dedicated warehouse and office, bringing fulfillment, inventory, Happy Jack, and several other pieces of their business under one roof.
Along the way, we celebrate Jim Madison, mourn Dolly Parton and Andy Williams, talk old country music, Tubi, forgotten movies, great television, Hollywood prop houses, and why sometimes losing the thing you thought was keeping you secure creates the space to finally build the thing that's yours.
A conversation about pivoting, trusting your taste, building a brand with a point of view, and watching a side project become a real company.