When Octavia Windom-Wiggins first connected with the Community Loan Fund, she wasn't just looking to start a business — she was looking for direction. Octavia had the passion and the lived experience, but she didn't yet have the structure. Like many aspiring entrepreneurs, Octavia had a lot of ideas and ventures that she wanted to pursue but wasn't quite sure where to start. To get the tools and knowledge to start her venture, Octavia enrolled in the Community Loan Fund's 9-week Business Planning Course. Upon her initial entrance into the course Octavia was pursuing `the idea of opening a lounge in downtown Albany. Although the idea was to contribute to more accessible nightlife experiences in Albany, there was a community building aspect that really shone through. After exploring the feasibility of the idea through the course, Octavia determined that she would pivot her business goals into a more community minded initiative that focused on her current expertise and lived experience. "I already have the hardest part," she reflects — the education and experience.  

An Albany native and graduate of Albany High School's Class of 2010, Octavia has also earned degrees from Hudson Valley Community College and SUNY Empire. She is now a licensed dental hygienist with more than seven years of professional experience working directly with patients across socioeconomic backgrounds. She saw children arriving at dental offices already traumatized by the condition of their teeth. She saw families navigating preventable oral health crises simply because they lacked access, education, or both. She saw adults facing four- and five-figure treatment plans that could have been avoided with earlier intervention. These experiences sparked a simple but powerful question – If oral health is this critical, why is no one addressing the access gap at its root? The solution to this question became Operation Tooth Fairy. An intersection of Octavia's professional credentials and her passion for community involvement. 

The Story Behind the Name

Founded by Octavia Windom-Wiggins, the name Operation Tooth Fairy may sound whimsical, but the mission behind it is anything but lighthearted. This movement is intentional. Recognizable, approachable, and relatable — children identify with it, and adults remember it. Originally conceived as a child-focused initiative, Operation Tooth Fairy has evolved into a community-driven oral health advocacy movement to bridge the gap between oral hygiene access, education and prevention. At its core, Operation Tooth Fairy believes oral health should be a basic standard of care—just like bathing, washing your hair, or practicing everyday hygiene. Yet for too many families, oral care is overlooked until it becomes an emergency.

The idea of Operation Tooth Fairy moved from thought to action in late September 2025, when Octavia attended a local city council meeting. What began as a casual conversation with a fellow attendee turned into a pivotal moment. Octavia shared her vision for improving oral health access in Albany, and that conversation led to direct introductions within the Albany City School District. By October, Operation Tooth Fairy was no longer just an idea — it was in motion. Suddenly conversations evolved into toothbrush drives, community partnerships, and the first major supply drop in February 2026. 

 

More Than Toothbrushes

Operation Tooth Fairy is not simply a supply drive. The organization focuses on two core components: donating oral hygiene supply kits which include toothbrushes, toothpaste, and floss and providing oral health education which allows participants to learn effective brushing techniques, the importance of flossing, how to build consistent oral routines and what prevention looks like in everyday life. Octavia is actively exploring more streamlined donation systems and long-term funding models. But the bigger picture is clear: Establish consistent oral health programming in schools, expand to nonprofits serving vulnerable populations, advocate for early education to prevent long-term dental trauma and reduce the financial burden of preventable dental procedures.

Currently, Operation Tooth Fairy operates under Octavia's for-profit entity Wiggins Enterprises, but her long-term vision includes forming a non-profit organization capable of serving schools, shelters, addiction centers, maternity wards, and other community-based organizations supporting residents with limited access to care across the region. 

How the Community Loan Fund Helped Clarify the Vision

While Octavia possessed clinical expertise and passion, translating that passion into a structured, scalable initiative required clarity. That is where the Community Loan Fund's 9-week Business Planning Course became transformative. The Community Loan Fund's mission focuses on training entrepreneurs, expanding economic opportunities, and strengthening local impact. Through its structured curriculum, the program equips business owners with tools to turn ideas into viable, sustainable ventures. For Octavia, that meant turning a well-intentioned community initiative into a strategic entrepreneurial endeavor. Although Operation Tooth Fairy launched months after Octavia's formal graduation from the course, the foundational knowledge and resources helped guide her. Perhaps most importantly, it strengthened her entrepreneurial confidence to make decisions and enter intro strategic partnerships. Instead of asking, "How do I do this?" she began asking, "How do I scale this?"

Community advocacy does not always look like protests or podium speeches. Sometimes it looks like:

  • A toothbrush in a child's backpack
  • A flossing demonstration in a classroom
  • A family understanding the long-term cost of neglect
  • A hygienist deciding to step beyond the office and into entrepreneurship

Through Operation Tooth Fairy, Octavia Windom-Wiggins is not just improving smiles — she is strengthening a system. Her goal is simple but profound: make oral hygiene as normalized and foundational as washing your hair or showering after the gym. "If we can create a stable foundation of basic oral care," she explains, "we prevent so much suffering down the line." 

Through the Community Loan Fund's training, Octavia has positioned Operation Tooth Fairy not merely as a charitable effort, but as a structured, impact-driven initiative with measurable outcomes. This is what community economic development looks like in practice: equipping a local professional with business training so she can reinvest her expertise back into the neighborhoods that raised her.