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Exploring Life & Business with Caylon Umphrey of Heartland Special Needs Foundation

Today we’d like to introduce you to Caylon Umphrey.

Hi Caylon, so excited to have you with us today. What can you tell us about your story?
My journey with Heartland Special Needs Foundation began in January of 2025, just after the organization completed a meaningful rebrand from its original name, Special Needs Assured. Stepping into the role of Executive Director at that moment felt significant—not only because of the timing, but because the mission was already firmly rooted in compassion, education, and a deep understanding of the gaps that continue to impact individuals with disabilities and their families.

Heartland Special Needs Foundation was founded in 2020 by Samantha Shepherd in response to those very gaps. As an attorney working closely with families in the special needs community, Samantha consistently saw that even well-crafted special needs trusts and government benefits often fell short. Families needed more—more education, more resources, and more opportunities for connection and collaboration. Special Needs Assured was created to help fill that space by providing education, financial support, and community engagement throughout the Kansas City area.

As the organization grew, so did its vision. In 2024, the rebrand to Heartland Special Needs Foundation reflected a broader and more community-centered mission—one focused on strengthening the heart of the special needs community across Kansas City and beyond. When I joined the organization in 2025, it was clear that Heartland was entering a new chapter, one defined by intentional growth, stronger partnerships, and expanded educational outreach.

That same year, Samantha Shepherd launched the KC Special Needs Conference, recognizing a critical need to better educate professionals who serve individuals with disabilities and their families. The conference was designed to bring together legal, financial, healthcare, and community professionals to share knowledge, best practices, and practical tools to better serve the Kansas City special needs community. All proceeds from the conference directly benefit Heartland Special Needs Foundation, allowing the education shared at the event to translate into tangible support for families through our programs and grants.

As Executive Director, I am actively involved in all aspects of the organization’s work. I attend all committee meetings, collaborate closely with our Executive Board, and help plan the KC Special Needs Conference alongside Samantha Shepherd, who chairs the conference committee. The conference is further strengthened by the dedication of Samantha’s esteemed friends and colleagues—professionals who generously lend their expertise, time, and passion to ensure the event remains impactful and mission-driven.

Today, Heartland Special Needs Foundation is guided by a committed Executive Board and supported by three standing committees—Community Partnerships, Education, and Development—along with focused sub-committees, including Grant Writing and KC Special Needs Conference Planning. Together, our board members, committee volunteers, and community partners bring professional expertise and lived experience to everything we do.

At its core, Heartland Special Needs Foundation exists to educate families on protecting vital benefits such as Medicaid and SSI, to provide grants to underfunded special needs trusts, and to bring the special needs community together. What began as one founder’s response to unmet needs has grown into a trusted community resource. I am honored to help lead this work forward—supporting collaboration, expanding education, and ensuring that individuals with disabilities and their families are informed, empowered, and supported every step of the way.

Would you say it’s been a smooth road, and if not what are some of the biggest challenges you’ve faced along the way?
Like many grassroots nonprofits, our journey has not been without challenges. Building Heartland Special Needs Foundation from the ground up required navigating limited resources, establishing credibility, and educating the community about a mission that is both complex and deeply personal. Early on, one of our greatest challenges was helping families understand the importance of proactive planning—particularly around protecting critical benefits like Medicaid and SSI—while also addressing immediate, real-life needs.

As we grew, we also faced the realities common to small but expanding organizations: developing sustainable funding streams, recruiting dedicated volunteers, and putting the right governance and committee structures in place to support long-term impact. The decision to rebrand in 2024 was another pivotal moment. While necessary to better reflect who we are and the heart of our work, it required thoughtful communication, patience, and trust-building with supporters who had known us under our original name, Special Needs Assured.

Despite these challenges, each obstacle strengthened the organization. They pushed us to become more strategic, more collaborative, and more deeply connected to the Kansas City special needs community. The road may not have been smooth, but it has been purposeful—and every challenge has helped shape Heartland Special Needs Foundation into a stronger, more resilient organization, better equipped to serve individuals with disabilities and their families.

Alright, so let’s switch gears a bit and talk business. What should we know?
At Heartland Special Needs Foundation, education is the foundation of everything we do. We believe that access to clear, practical knowledge empowers individuals with disabilities and their families to build a more secure financial future. Through targeted education around special needs trusts, public benefits such as Medicaid and SSI, and long-term planning strategies, we help individuals and families make informed decisions that protect vital resources while enhancing quality of life.

Beyond individual education, we are deeply committed to connecting the special needs community. We bring families, caregivers, and professionals together through workshops, educational events, and shared learning opportunities designed to foster collaboration and understanding. By creating spaces where information is accessible and conversations are open, we strengthen a network of support that benefits individuals with disabilities at every stage of life.

This commitment to education and connection expanded in 2025 with the launch of the inaugural KC Special Needs Conference, an initiative envisioned by founder Samantha Shepherd. Recognizing a growing need for high-quality, ongoing education for professionals serving the special needs community, Samantha imagined a conference that would elevate professional knowledge, sharpen expertise, and ultimately improve outcomes for individuals with disabilities. The inaugural event exceeded expectations—meeting both sponsor and attendance goals and drawing attendees from 11 states across the country—demonstrating a clear national demand for this type of accessible, specialized education.

Building on that success, the KC Special Needs Conference will return in 2026 as an expanded two-day event, taking place May 4–5, 2026. While the 2025 conference met its goals, Heartland Special Needs Foundation chose to grow the event intentionally to provide even more in-depth educational programming. The expanded format will allow for additional sessions, deeper learning opportunities, and broader perspectives—benefiting professionals not only locally, but nationally.

The conference is designed to strengthen the professionals who support individuals with special needs, including attorneys, financial advisors, healthcare providers, caregivers, and advocates. By equipping professionals with current insights, best practices, and practical tools, we multiply our impact—ensuring that individuals with disabilities receive informed, compassionate, and forward-thinking support wherever they live.

Proceeds from the KC Special Needs Conference directly benefit Heartland Special Needs Foundation, a registered 501(c)(3) public charity, further advancing our mission. Through education, community connection, grants to local individuals with disabilities, and innovative initiatives like the KC Special Needs Conference, Heartland Special Needs Foundation remains committed to supporting individuals with disabilities in meaningful, lasting ways.

How do you define success?
For us, success isn’t about numbers on a spreadsheet—it’s about people feeling more confident and less overwhelmed. When individuals with disabilities and their families walk away from an event, conversation, or resource understanding their options a little better and feeling more prepared for the future, that’s a win. If we’ve helped someone protect important benefits, ask the right questions, or feel more in control of their planning, we know we’re on the right track.

We also see success in the connections that happen along the way. When families, professionals, and advocates come together, share knowledge, and support one another, the whole community gets stronger. If people feel less alone, better informed, and supported by a network that truly understands their needs, that’s how we know our work is making a real difference.

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