Today we’d like to introduce you to Will Cunningham.
Hi Will, it’s an honor to have you on the platform. Thanks for taking the time to share your story with us – to start maybe you can share some of your backstory with our readers?
After more than 20 years serving as a Green Beret in the Special Operations community, I transitioned out of the military with a deep desire to continue serving—just in a different way. I grew up in Northern Virginia, and throughout my career I had the privilege of leading teams, solving complex problems, and operating in high-stakes environments. At its core, though, my work was always about people and purpose.
As I began my transition, I knew I wanted to stay connected to that sense of meaning while also building something of my own. That led me to entrepreneurship and ultimately to launching Square Cow Movers here in Raleigh. What drew me to this business was the opportunity to serve people during pivotal moments in their lives—whether it’s a family moving into a new home, a professional relocating for a new opportunity, or someone navigating a challenging life transition.
Today, I’m proud to lead a team committed to what we call Second Mile Service—a faith-based principle rooted in going above and beyond what’s expected to truly serve others. Our purpose is simple: serve the community, grow leaders, and invest locally. We’re building more than a moving company; we’re building a culture centered on intentional service, personal growth, and making a lasting impact in the community we’re grateful to call home.
I’m also a proud father to my daughter Kit and my son Cale. I’m driven by my core values of character, family, fitness, and impact, which are all underpinned by my faith. This next chapter is about carrying forward a life of service—just in a new arena—while building something meaningful for my family, my team, and the community we’re honored to serve.
I’m sure it wasn’t obstacle-free, but would you say the journey has been fairly smooth so far?
Starting something new always comes with challenges, and this journey has been no different. That said, I believe my background in Special Operations—and a commitment to continuous growth—prepared me well to navigate uncertainty and adapt quickly.
As I began this transition, I was intentional about learning from others and building a strong foundation. I participated in several programs including the Special Operations Transition Foundation, Vet to CEO, Owners in Honor, and I’m currently an MBA candidate at NC State. Each of these experiences helped shape how I approached entrepreneurship and gave me a strong network of mentors and peers.
One of the most impactful decisions I made early on was bringing a former service colleague on as my General Manager. We’ve lived the idea that it’s better to go farther together, and having someone I trust alongside me has made a significant difference in how we’ve built the business.
Along the way, we’ve faced our share of challenges—from navigating insurance requirements for a higher-risk industry, to temporarily losing our operating authority due to a simple administrative error, which required a same-day trip to the North Carolina Department of Transportation to resolve. On top of that, every move presents its own unique challenges, especially as we serve both residential and commercial clients with very different needs.
Through it all, one lesson from my time in Special Operations has remained constant: it’s about the people. The strength of the team and the culture you build will determine how you respond to challenges and ultimately how successful you become. That focus continues to guide everything we’re building at Square Cow Movers.
Thanks – so what else should our readers know about Square Cow Moovers?
Square Cow Movers is a full-service moving company based in Raleigh, serving both residential and commercial clients locally and across state lines. We specialize in handling moves during some of life’s most important transitions—whether that’s a family settling into a new home, a professional relocating for an opportunity, or a business navigating growth and change.
What sets us apart is our commitment to what we call Second Mile Service—a faith-based principle of going above and beyond what’s expected to truly serve others. In an industry where the experience can often feel transactional, we focus on delivering a level of professionalism, care, and respect that people remember. From how we communicate, to how we protect our customers’ homes and belongings, to how we show up on moving day—every detail matters.
We’re also a SOF veteran-owned and operated business, and that background shapes how we lead, operate, and build our team. We emphasize accountability, trust, and attention to detail, and we’re intentional about creating opportunities for our team members to grow as leaders, not just employees.
Brand-wise, what I’m most proud of is the culture we’re building. We’re not just trying to be the biggest moving company—we’re trying to be a company that people want to work for and customers feel confident referring to others. Our purpose is simple: serve the community, grow leaders, and invest locally. That mission shows up in how we hire, how we train, and how we engage with the community around us.
What I want readers to know is that we genuinely care about the people we serve. Moving can be stressful, and our goal is to bring a sense of calm, professionalism, and trust to that experience. If someone chooses Square Cow Movers, they’re not just hiring a moving company—they’re partnering with a team that takes pride in doing things the right way and going the extra mile every time.
How do you think about happiness?
What makes me happiest is building something that creates real impact—both for the people on our team and the community we serve.
I’ve spent most of my life in environments where purpose and teamwork mattered, and I’ve found that same fulfillment in building Square Cow Movers. There’s something incredibly rewarding about bringing together a group of people, developing them as leaders, and watching them grow in confidence and capability. It’s not just about completing moves—it’s about building a team that takes pride in how they show up and serve others.
Serving the community is a big part of that. Every move we complete is an opportunity to step into someone’s life during a meaningful transition and make that experience better. Beyond the work itself, we’re intentional about giving back and staying connected locally. We’re proud sponsors of Oak & Ember, a hyper-local charitable consortium focused on making a tangible impact in our community. Being part of that group aligns directly with why I chose business ownership—to invest locally and contribute to something bigger than ourselves.
We’re also committed to supporting those who have served. As a veteran-owned business, we actively hire veterans and National Guard and Reserve service members, and we’ve partnered with organizations like Military Missions in Action (MMIA) to support veterans in our community.
At the end of the day, what drives me is knowing that the business we’re building is doing more than generating revenue—it’s creating opportunity, strengthening our community, and allowing us to serve with purpose every day.
Contact Info:
- Website: https://squarecowmovers.com/locations/raleigh/
- Instagram: https://www.instagram.com/squarecowmovers_nc/?hl=en
- Facebook: https://www.facebook.com/squarecowmoversraleigh
