Sprinting to Success

Most organizations treat a capital campaign like a marathon. Holly Kessler’s team treated theirs like a sprint, and they’re about to cross the finish line on a $1.1 million goal with a staff you could fit in a minivan.

Holly is the Director of Community Engagement at Forsyth Jail and Prison Ministries in Winston-Salem, North Carolina. The ministry has served the county jail and a state work-release prison camp since 1977, through chaplaincy, a pre-release Transition to Work program, and post-release support. Holly is an ordained pastor who spent more than a decade in child welfare fundraising before joining the ministry in early 2024. She didn’t go looking for prison ministry. It found her.

In this episode, Andrew and Holly unpack how a five-person full-time team bought a building, renovated it, and opened a reentry center in under a year. They also kept the annual fund on track the whole time. Holly shares the low-budget marketing that worked, the open house they threw for a building they didn’t own yet, and the one-word lesson that changed how they ask for major gifts: specific.

The Conversation

Act One: “I Can Raise Money for That”

When Holly interviewed for the job, she asked her future executive director a dangerous question (04:39): after nearly 47 years of steady work, what’s next? His answer was a dream to build a reentry center with transitional housing, meeting space, and a stronger post-release program. Holly’s reaction was immediate. “I can raise money for that.” Her logic was hard to argue with. These men are coming home one way or the other. The only question is whether they come home with support.

The board said yes in 2025, and things moved fast (06:37). The silent phase started that summer. The campaign went public at the ministry’s October breakfast, and the building was purchased the same month. They raised more than $600,000 by year-end. Renovations ran from December to April, and the First Lady of North Carolina, Anna Stein, spoke at the May ribbon cutting. A week later, the first two residents moved in. As of recording, they’re $28,000 from the goal.

Act Two: Two Asks, One Breakfast

Holly’s biggest surprise was the speed (07:57). The campaign budget was about one and a half times the ministry’s annual budget, and the team still hit its annual fund goal in both years. The less pleasant surprise: a few donors who were expected to step up didn’t. Andrew can relate (08:57). In one of his own campaigns, a board member proudly pulled out a credit card and gave $50. Sometimes that’s just how it goes.

So how do you ask for capital and annual dollars without one eating the other (09:43)? Their consultant was blunt. Everyone already knew about the project, so not mentioning it at the breakfast would be weird. Some people would shift their annual gift, and the team would have to live with that. The fix was clarity. They used separate pledge cards, presented the campaign first and the annual fund second, and the executive director closed by saying, in effect, “We need your annual gifts too.” Lots of people gave to both.

Act Three: The Good-Enough Playbook

Holly’s first keeper is a little heretical (11:35). They wrote a strong case statement and professionally printed one page. Everything else, including the videos, was made in-house. A slick video gets watched once, she says, so “good enough” really is good enough.

The second keeper came from their realtor (12:40). He convinced the seller to let the ministry host an open house before closing. Big artist renderings showed visitors what the empty rooms would become, and the footage later helped breakfast guests who missed it see the same vision. The third: they applied for every capital grant they could find (13:25). They won more than half, several from brand-new funders. That matters in