Are you a small business owner? If so, you're likely already making a difference for your community. Over 90% of small business owners support charities and community activities. But are you maximizing the tax benefits while creating meaningful change?

Donating your business interests to charity can be a powerful strategy that achieves both your financial and philanthropic goals. Here's what you need to know:

Choose The Community Foundations Over Private Foundations: When you donate closely-held stock to The Community Foundation, you can typically deduct the full fair market value (up to 30% of your adjusted gross income) and avoid capital gains tax. With a private foundation, you're limited to deducting only your cost basis (up to 20% of AGI)—a much less favorable outcome.

Timing Is Everything: Plan your charitable gift before reaching out to potential buyers and definitely before finalizing any deal. This separation is crucial because it allows you to avoid significant unrealized capital gains that have accumulated over the years. When done correctly, your charitable fund receives 100 cents on the dollar for its portion of the stock, and your deduction remains valid.

Get Proper Valuation: Always obtain a professional valuation for charitable deduction purposes when contributing business interests. This has become even more important following the recent Supreme Court decision in Connelly v. United States, which could result in higher taxable estates for business owners—creating additional incentive to include charitable giving in your planning.

Ready to explore how your business success can create lasting community impact? Contact our General Counsel & Senior Philanthropic Advisor, Tiffanie Purvis at tpurvis@thecommunityfoundation.org to discuss how charitable giving can work for your specific situation.

Disclaimer: This information is for educational purposes only and should not be taken as legal or financial advice. Please speak with your own advisor to assess your specific situation.

When Ward Howick first walked into Rachael's Women's Center in 1997, he immediately felt the warmth and safety that defined the organization. Located in a four-story townhouse on 11th Street between M and N, the center had been serving women experiencing homelessness in Washington, DC since 1979, providing a crucial daytime refuge in downtown DC where women could find community, resources, and hope.

"It almost felt like home," recalls Howick, who joined the board that year and would eventually serve as Chairman. "No matter where you came from or what you were going through, everyone felt safe and comfortable there."

For over three decades, Rachael's Women's Center was more than just a day shelter—it was a lifeline. The statistics tell a remarkable story of impact: over 1 million meals served, 162,750 showers provided, and more than 75,000 women served since opening its doors. The center offered everything from case management and counseling to job training programs, computer classes, and connections to permanent housing.

A Family Atmosphere in the Heart of DC

What made Rachael's unique wasn't just the breadth of services, but the family-like atmosphere that permeated every interaction in the heart of downtown DC. As a day shelter, Rachael's filled a critical gap in the city's homeless services landscape—providing a safe, welcoming place where women could spend their days when other facilities were closed or unavailable. From its downtown location – the center was easily accessible to women throughout the city, offering a vital refuge in an area where such services were desperately needed.

Women could receive mail at the center—a critical service for those without permanent addresses. The kitchen staff, led by individuals with lived experience, provided not just meals but caring connections. Annual talent shows gave women opportunities to share their poetry, artwork, and music, celebrating their talents and humanity.

The center's approach was holistic, addressing not just immediate needs but working toward long-term stability. Staff helped women access benefits, connect with legal services, and transition into permanent housing.

Howick himself became deeply involved in job placement efforts, frequently connecting women from the center to temporary employment opportunities through his company, the Midtown Group. Many of these placements were with DC government agencies, leveraging Howick's professional connections to create pathways to stable employment. This direct pipeline to work became one of the center's most valuable resources, providing women with both income and professional experience.

The organization also partnered with more than 75 nonprofit organizations throughout the metropolitan area, creating a network of support that extended far beyond their physical location. They developed programs that taught practical skills—from barista training to interview preparation—while also addressing the underlying challenges that contributed to homelessness.

Facing Difficult Realities

By the early 2010s, however, Rachael's Women's Center faced a challenging convergence of circumstances that many nonprofits encounter: aging infrastructure, rising operational costs, and the constant pressure of sustaining both programs and facilities. The organization owned multiple properties that were deteriorating, and the financial burden of maintaining these buildings while continuing to serve hundreds of women annually was becoming overwhelming.

The board members, who had poured decades of their lives into the organization, found themselves caught between their deep commitment to the mission and the harsh realities of operational sustainability. As Howick recalls, they were "beaten down with constantly worrying about it—thinking about how much money we had after we paid everybody."

What made the situation particularly complex was that the organization was successful in its core mission. Women continued to need and benefit from their services, the staff remained dedicated, and the community impact was undeniable. Yet the infrastructure challenges were threatening the organization's ability to continue operating effectively.

"Eventually, we realized that we needed to try something different," Howick reflects, with emotion in his voice. “It was painful; but I think we knew it would ultimately be the better option in the long-run.”

The decision-making process stretched over at least a year, with board members carefully weighing their options and grappling with questions that went far beyond finances: How do you honor the legacy of an organization that has been a lifeline for thousands of women? How do you balance the needs of current staff and clients with long-term sustainability? And perhaps most importantly, how do you ensure that the mission continues even if the organizational structure must change?

A New Model for Continuing Impact

In 2015, after 36 years of operation, Rachael's Women's Center closed its doors. But rather than simply disbanding, the board made a transformative decision: they would use the proceeds from the sale of their properties to establish Rachael's Fund through the Greater Washington Community Foundation.

The transition represented a fundamental shift in how the organization would continue its mission. Instead of directly serving women experiencing homelessness, they would now support other organizations doing similar work across DC. The board remained committed to the cause that had driven them for decades.

"We knew which organizations needed the help because we had worked in the space," explains Howick. This deep familiarity became the foundation for a distinctly personal approach to grantmaking.

It also allows the fund to make strategic investments in organizations that might otherwise struggle to access funding, particularly those operating with annual budgets below $1 million—a deliberate choice based on the board's own experience understanding the challenges of operating at that scale.

The numbers tell the story of steady, sustained impact: 47 grants totaling $308,500 distributed to eight different nonprofit organizations. The fund typically awards $45,000 to $50,000 annually, with grants sized to make meaningful differences for smaller organizations while ensuring the fund's longevity.

While the fund initially focused on organizations serving women experiencing homelessness—staying true to Rachael's Women's Center's original mission—it has thoughtfully expanded its scope. Current grant recipients include organizations working with children, families, and members of the deaf and hard of hearing community, reflecting a broader understanding of the pathways into and out of homelessness.

As Howick explains, "We always took care of women experiencing homelessness, so we want that to be included, but we've branched out... anything that's going to prevent homelessness in the future, we're going to try and invest in that."

The services these organizations provide mirror many of those once offered directly by Rachael's Women's Center: substance abuse counseling, emergency shelter for homeless families, job training programs, life skills counseling, and case management. In this way, the fund has become a multiplier of impact, enabling multiple organizations to carry forward the comprehensive approach that defined Rachael's original work.

One of the fund's most meaningful aspects is how it has maintained the relational approach that characterized the Women's Center. In the early years, Howick would personally deliver grant checks to recipient organizations—a practice that reflected the fund's commitment to relationship-building rather than just check-writing.

A Legacy of Care

Today, Rachael's Fund continues to evolve. For Howick, who has now been involved with the organization in various forms for over 25 years, the continuity of mission matters more than the structure.

The transformation from Rachael's Women's Center to Rachael's Fund represents more than just an organizational restructuring—it's a testament to the power of adaptive leadership and unwavering commitment to mission. In an era when many nonprofits face difficult decisions about sustainability and impact, Rachael's story offers hope that organizations can find creative ways to continue serving their communities, even when traditional models no longer work.

The warmth and safety that defined Rachael's Women's Center for over three decades now lives on through the organizations they support, ensuring that the legacy of care continues to reach some of DC's most vulnerable residents.

In a city where homelessness remains a persistent challenge, Rachael's Fund stands as proof that sometimes the most impactful way to continue a mission is to empower others to carry it forward.

The Community Foundation is proud to support organizations like Rachael’s Fund in continuing to make a difference in our community. For more information about Rachael’s Fund, contact Mary Lou Tietz at maryloutietz@yahoo.com.