When you talk with Glena Stephenson of G Wiz Your Biz company, you immediately feel her warmth, wisdom, and genuine belief that business can and should build connection. A lifelong entrepreneur and community advocate, Glena has turned storytelling into structure and structure into empowerment. Through Chad Nicely’s Entourage Mastermind and the Letterman platform, she’s found the perfect vehicle to bring her vision to life: connecting people, ideas, and opportunities through systems that make communities stronger. Her newsletter, Elders Living a New Reality, reflects her core philosophy that creativity and contribution go hand in hand. For Glena, every story is an invitation to belong.
Listen in for a very insightful talk.
Carol: What first drew you into Chad Nicely’s Entourage and what led you to start using Letterman?
Glena: I’ve always gravitated toward projects where communication and community collide. Over the years I’ve owned businesses, worked with nonprofits, and worn nearly every hat in between. Newsletters became a common thread. I co-edited three nonprofit publications, where I didn’t just edit articles, I rolled up my sleeves on the backend, suggested creative ways to offset costs, and even built advertising programs that gave local businesses a spotlight. Eventually, I was leading the advertising team. That role lit me up, because I loved discovering the stories behind each business and finding ways, we could support each other.
When I crossed paths with Chad Nicely, I was already using his tools for marketing and social media. Then he floated the idea of Local Newsletters, and it felt like he had built a bridge to exactly what I’d been looking for. I’d tried other publishing tools before, but they were either clunky, incomplete, or missing the strategic “how-to” that makes the difference. Chad’s approach was different. He wasn’t just offering software; he was offering the whole ecosystem: training, systems, and, most importantly, his accessibility; putting people first.
What struck me most about Chad was his speed and integrity. He’s a builder at heart. When he sees a way to make something shine brighter, he doesn’t just talk about it, he executes. He makes sure you can execute alongside him. That’s rare in this space. That combination of ingenuity, accessibility, and generosity is what pulled me into his
Entourage and ultimately into Letterman. It’s not just a publishing platform, it’s a full system, guided by a mentor who practices what he preaches and a community that grows together.
Carol: Perfectly stated Glena and I so agree. Chad is a rare advantage. You mentioned Chad’s speed and integrity really stood out. Can you recall a moment where that “builder energy” inspired you to push forward faster than you might have on your own?
Glena: When Chad launched his new software, something clicked for me. I’d been helping a friend develop the idea of a living community for elders focused on health, contribution, and self-sufficiency. After seeing Chad’s speed and how he brought ideas to life so quickly, I realized we could start inspiring people now, not years from now. That’s when I launched Elders Living a New Reality. Anyone who shared that vision could participate, whether or not they lived on the property. His builder energy pushed me to act instead of waiting.
Carol: As you’ve started putting Letterman into action, what’s been the most powerful or even surprising part of the experience for you?
Glena: For me, the shock factor was speed. Having produced newsletters for years, I know the slog: endless drafts, tech glitches, advertising snags. What used to take weeks now takes days, sometimes hours. Letterman strips out the bottlenecks, leaving room for the fun parts: creativity, strategy, storytelling. The real power, though, is in how that
simplicity unlocks creativity. Instead of wrestling with logistics, I can focus on shaping the content, the strategy, and the connections.
Watching an idea transform quickly into something real that people respond to has been energizing.
Carol: Was there a specific newsletter or edition where you felt that shift most clearly? Where the speed and simplicity really gave you space to be more creative?
Glena: It happened around the third issue of Elders Living a New Reality. I remember feeling overwhelmed and unsure I could keep it going on my own; I had about twenty subscribers then. Because the publishing process had become so simple, I had room to think bigger. I reached out to a friend who develops recipes for her sister with
gluten intolerance, a nurse who hosts a diabetes and wellness podcast, and a nutritionist with her own cooking show and books. Suddenly, the newsletter wasn’t just mine, it became a shared creative space, and that collaboration sparked a whole new level of energy.
Carol: I can imagine it did Glena. Everyone brings their own strengths to the table in Letterman. What do you feel you’ve brought to Letterman that helped you get results or set you apart?
Glena: My strength has always been creating structure that empowers people. In every role, running a painting company and training subcontractors, leading leadership programs at Landmark, or working one-on-one as a caregiver, I’ve always focused on building systems that work consistently and can be handed off. With Letterman, I’ve applied that same discipline. I don’t just “make a newsletter.” I map out frameworks for growth, design processes that bring in sponsors, and connect local stories to business outcomes in ways that feel authentic. I invite small business owners to write articles to introduce them to people interested in their products or services. I see each publication as more than content; it’s infrastructure for community impact.
What sets me apart is the blend: systems thinking, creative storytelling, and a people first approach. That combination turns newsletters into more than just another publication, it makes them engines for engagement and growth.
Carol: That blend of structure and storytelling is powerful. Have you seen that inspire a small business owner or community partner to take a leap they might not have taken otherwise?
Glena: Yes. One of my contributors, nutritionist Ricki McKenna, used to write a weekly column for a small local newspaper years ago. After contributing articles to my newsletter, she rediscovered how much she loved writing and sharing her expertise. That spark inspired her to reach out to other publications, and now she’s contributing to several news outlets again. It reconnected her to a passion that had been waiting in the wings.
Carol: I love that. How wonderful Glena for you both and for all who are benefitting. Subscriber growth is a huge part of Letterman’s success. Outside of Facebook, what have you tried, or are you exploring, to bring in subscribers?
Glena: I think of subscriber growth like weaving a net: local, layered, and personal. Locally, I partner with restaurants, wellness centers, and community organizations so subscribing feels less like “signing up” and more like joining a circle. Each edition connects people to hidden gems, events, and stories that make them proud of their town.
Beyond that, I’m layering in tools that keep growth interactive quizzes to uncover what readers want most, referral programs that reward sharing, and offline connections through events. Where others lean hard on blasting ads, I take the slower but stronger route: building trust and curiosity. The result? Subscribers who don’t just sign up, stay,
engage, and even invite others in.
Carol: I love that “weaving a net” image. What’s been the most surprising way new subscribers have found you? Maybe something you didn’t expect to work but did?
Glena: Honestly, it’s been the personal connections. Some of my subscribers have come simply through word of mouth. With all the social media tools and digital noise out there, what still works best is the human touch—reaching out, having real conversations, and sharing what I’m passionate about. That kind of personal connection builds a community that isn’t just reading the newsletter, they’re learning from each other and becoming part of something together.
In addition, one of the most meaningful “partnerships” has been with a friend who builds websites for small businesses. After watching what I was doing with my newsletters, she saw how powerful it could be to connect business owners in her own area the same way. She’s now creating her own newsletter to feature local entrepreneurs and help them grow. Seeing that ripple effect, how one idea can inspire someone else to build their own version of community, reminded me that collaboration doesn’t always start with a contract. Sometimes it starts with inspiration.
Carol: Beautiful. Yes, it does. What drives your passion for entrepreneurship, and how does that show up in your work day to day?
Glena: Entrepreneurship has been part of my life from the very beginning. I grew up surrounded by it, my mother sold Stanley Home Products, our close friends ran a cabinet shop, and one Christmas my mother gave my brother and me two looms with cotton loops. That gift became our first little business: we manufactured potholders all
winter and sold them all summer.
Even then, what drove me was finding creative ways to connect with people and help them. That same drive shows up in my work today. Every day I’m learning something new, experimenting with tools and strategies, and sharing what I discover. Whether I’m in a mastermind, on a Zoom call, or testing new software, I’m not just learning for myself, I’m teaching others how to use these tools to build, grow, and express their own ideas. For me, entrepreneurship isn’t just business, it’s a way to spark creativity and connection every single day.
Carol: That’s such a great story. Do you feel that early “maker” mindset still influences how you approach business today — testing, creating, and sharing as you go?
Glena: Absolutely. It’s the foundation for everything I do. That early “maker” mindset shaped how I see business and creativity. It doesn’t matter what role I’m in or what kind of business I’m building; I’m always curious, always learning, and always sharing what I discover with the people around me. From making potholders as a child to creating newsletters today, the process is the same: try something new, see what works, refine it, and help others do the same. That spirit of creating, testing, and teaching is woven into everything I do.
Carol: If someone brand new came to you and asked how to succeed quickly with Letterman, what advice would you give them?
Glena: The first step is clarity. Decide what kind of newsletter you want to create. Is it focused on local events and businesses? Is it educational or training-based? Or is it meant to inspire? Once you’re clear on your purpose, get just as clear on who your audience is and what they want.
From there, be intentional and consistent. A newsletter isn’t just about filling space. It’s about delivering real value. The most rewarding goal is to transform someone’s life, or at the very least, make a difference for them. Readers always want to know “what’s in it for me,” and if you can answer that consistently, your newsletter will succeed. Clarity, consistency, and care, that’s the recipe for making Letterman work.
Carol: Great answer! Clarity, consistency, and care. Could you share one way you personally stay consistent week after week, even when things get busy?
Glena: Consistency for me comes from connection. I’m part of two mastermind groups, and the support from those communities keeps me on track. We share ideas, swap newsletters and give each other a nudge when the energy dips. On those busy or low-motivation days, I can always reach out for a quick boost. That kind of collaboration keeps the momentum going, and makes the process a lot more fun.
Carol: Finally Glena, what legacy you’d like to leave?
Glena: The legacy I’d like to leave is one of connection and contribution. I want people to see that business can be creative, compassionate, and community-driven, and that anyone can start something meaningful right where they are. Through newsletters, mentorship, and collaboration, my goal is to spark curiosity, share knowledge, and encourage others to find their voice and use it to make a difference.
If the systems and communities I’ve built continue to help people feel more connected, to their purpose, to their neighbors, and to each other, long after I’m gone, then I’ll know my work truly mattered.
“I want my legacy to be proof that when we combine creativity, integrity, and connection,
we don’t just build businesses—we build communities.”
To connect with Glena: Cell: 832-647-1553 | Office 281-305-9512
