Going Big: 5 Lessons on Bold Asks and Fundraising Milestones from our Second Decade

To celebrate two decades of providing fundraising and strategic consulting services to more than 120 nonprofits, we’re reflecting on our clients’ biggest wins and revisiting the powerful lessons we discovered along the way.

As we approached our 20th anniversary, we helped clients mark their own milestones—whether they were celebrating a centennial anniversary or constructing a new facility—with bold vision and confidence. With a clear strategy to guide them, they laid the groundwork for a successful and sustainable future.

2020: Unlock new donors with strategy and vision 

In 2020, Nashua Soup Kitchen and Shelter set out to turn a former church into a shelter with much-needed beds and facilities. With no history of major gifts and no development director on staff, raising $8 million required a heavy dose of ambition and vision. The Heller Group partnered with them to build a campaign from the ground up, including writing a compelling case for support, training volunteers, building out prospect lists, developing a solicitation strategy, and even hiring their first development director. The result? With a clear mission and strategy, Nashua Soup Kitchen was able to uncover generous donors who made a lasting impact.

2021: With the right strategy, donors will rise to the occasion

When Family Services in Poughkeepsie, NY, came to us, they needed to raise $9.2 million to renovate the central hub where they served people throughout New York’s Hudson Valley region. While their CEO excelled at securing government support, the organization’s individual donor engagement was minimal. The Heller Group shifted that mindset. Through thoughtful strategy and bold asks, they secured transformational gifts—including a $2 million+ solicitation and donation from a family foundation that we encouraged and that far exceeded the amount the CEO initially wanted to ask for. 

2022: Think big and ask bigger

Fountain House in New York City approached us with an ambitious $75 million goal that would allow them to replicate their clubhouse model for mental health support and reach people nationwide. While they were clear in how to meet community needs, they weren’t confident in their ability to raise the funds to realize their vision. During the feasibility study, we encouraged Fountain House to have bold, honest conversations with their donors. The results were eye-opening — eight donors expressed willingness to make seven-figure gifts, including one who committed to $12 million.

2023: Tell the right story

Martha’s Vineyard Museum had plenty in its favor as it approached its centennial anniversary, including a new campus with room to tell a more encompassing story of the island’s history. However, lingering debt from the move, an overextended staff, and a previous campaign shortfall left staff and board members hesitant about the success of a comprehensive campaign. The Heller Group stepped in to revitalize their narrative, focusing on the museum’s role in the community and encouraging donors to find their place in the story. The shift resonated and the museum is closing in on its $16 million goal. 

2024: Landmark moments deserve bold action

Fountain Valley School in Colorado Springs was also on the cusp of its centennial anniversary when they called in the Heller Group to lead a feasibility study for what they hoped would be the largest campaign in its history. Through their campaign, they hoped to reimagine their campus and strengthen their endowment, setting the school up for the next 100 years. With our expert guidance and deep research, the school embraced a transformative fundraising strategy—and it’s rapidly paying off. Less than a year into the quiet phase, they’re already seeing record-breaking gifts.

That’s all—for now.

For 20 years, we’ve helped clients rethink their assumptions, try new strategies, and raise more money than they ever thought possible—and we’re just getting started. If our 20 stories of lessons learned have inspired you to bring in a fresh perspective, please reach out. You can schedule a free strategy session to find out more about the Heller Group and how our team of experts can guide you to fundraising success.