Military Entrepreneurship

Entrepreneurship Lessons from a Military Family Business

Every entrepreneur brings something to the table before they ever sell their first product. For Wendy Hively, that meant a creative hobby, education, and professional experience as a scientist. Add in a depth of passion for the military community, and you have the foundation for Charliemadison Originals, the military-pride jewelry brand Wendy now runs with her daughter and business partner, Madison.

That’s not to say the path was easy. Like any entrepreneur, Wendy and Madison have learned plenty through trial and error over more than a decade in a competitive industry. But ask them about it, and they’re just as quick to point to the wins: the moments that proved their instincts right and pushed the business forward.

We sat down with Wendy and Madison to talk about what it really takes to build something lasting. They shared their journey that led to their newest venture, Charliemadison Labs, which helps other entrepreneurs build and grow their own businesses. Whatever stage you’re at right now: still brainstorming, chasing funding, just getting started, or ready to scale, their story offers lessons worth borrowing.

Military entrepreneurs, please keep reading, then click here to enter this month’s contest and get connected with prizes to support you on your entrepreneur journey!

Know Your “Why” Before You Build a Brand

For Wendy, the military connection was never a marketing decision; it’s simply who her family is. With three generations and four branches of service represented across her family, she wanted to build something that gave back to a community that means so much to her. “The military had given us so much and had created this sort of special family,” she said.

That sense of purpose shaped everything that followed. Wendy focused first on defining what Charliemadison stood for. “Real branding isn’t about how something looks,” she explained. “It’s about how clearly a business can communicate why it matters to the people it serves.”

Still working out your own “why”? Start here:

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Let Your Story Do the Selling

Once the mission was clear, Wendy and Madison built their online presence around it, treating social media as a way to introduce people to who they really are rather than just what they sell. Madison pointed to collaboration as a key factor in this. Partnering with other people and communities builds trust that outlasts any single post.

That same instinct shaped how they think about their reputation online more broadly. “Nobody can tell your story like you can,” Wendy said, a philosophy that’s kept Charliemadison recognizable through more than a decade of growth.

Ready to build or adjust your brand’s online presence? These resources can help:

Trust Your Instincts, Even When Others Say Otherwise

Early on, Wendy learned to trust her own instincts. She had to learn about the jewelry industry on her own. That decision was reinforced by a mentor who told her not to chase the competition, but to own what made her different. Her advice stuck: rather than blending in, Wendy leaned into what set Charliemadison apart — their tasteful designs, their mission to give back, and staying true to themselves. Becoming the “bracelet queens” continues to be a badge they wear with honor.

That same confidence carried directly into her partnership with Madison. This mother and daughter team built Charliemadison around a shared mission and sense of purpose, trusting each other’s instincts as much as their own. For any founder comparing themselves to the competition or second-guessing their own approach, it’s a reminder that the things that make your business different are often exactly what make it work.

Build on a Foundation You Control

Even the less glamorous parts of business need attention and care. Regarding money questions like taxes and funding, Wendy’s advice to fellow military spouses and veteran entrepreneurs is: understand your business structure, stay organized, and don’t be afraid to bring in help. Fittingly, the bookkeeper who keeps Charliemadison’s finances in order is a military spouse herself!

That same instinct shaped how the business grew. Rather than pursuing venture capital, Wendy and Madison chose to reinvest their own earnings and grow at their own pace, protecting their creative control instead of answering to outside investors.

If funding or taxes are on your mind right now, start with:

Know When You’re Ready to Grow

The Hively’s newest venture, Charliemadison Labs, grew out of a simple realization: other entrepreneurs needed the same kind of guidance that Wendy and Madison once had to find for themselves. Rather than handing people a checklist, Charliemadison Labs is built to help entrepreneurs ask better questions, including how to handle setbacks. “Failure is part of the process,” Madison said. “You’re going to feel it, and it’s a good thing, because you learn something out of it.”

Wondering if your own business is ready for its next stage? Check out:

Charliemadison and GoVA Foundation

At its core, Charliemadison Originals is a story about connection: to family, to community, and to the military families it was built to serve. None of what Wendy and Madison learned along the way came easily. They built their business one lesson at a time and one win at a time, all while focusing on authenticity. It’s a mission that mirrors our own: GoVA Foundation exists to strengthen the financial confidence and wellbeing of the military community. Partnerships like this one are a reminder that we’re not alone in that work. The Edge’s entrepreneur resources exist to put the guidance that founders like Wendy usually have to learn the hard way directly in front of military spouses and veterans, for free.

Are You on an Entrepreneur Journey?

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