Just Ask - Rethinking Development

What if strengthening your annual fund was the key to unlocking your long-term fundraising strategy? In this episode, Greg takes the lead to explore how a focused mini-campaign within your annual fund can secure major...

The annual fund is often treated as the center of a fundraising program. But should it be? In this episode, Greg offers a thought-provoking perspective that may cause you to rethink where your development team’s time...

How soon can you ask for another gift? It’s one of the biggest fears in fundraising: asking again too quickly. But is there actually a “right” timeline? In this episode of Just Ask, we talk donor psychology...

Every fundraiser has a white whale. The donor you just know could come through… someday. Is it discipline to keep going, or denial? Let’s talk about when to walk away.

If your development team feels like a revolving door, it’s not just a hiring problem: it’s a strategy problem. In this episode, we dig into why talented fundraisers walk, what it’s actually costing your organization...

For years, endowments have lived in the “we’ll get there” category. But the reality is shifting. If long-term sustainability matters, building your endowment is no longer optional: it’s essential. In this episode, we...

AI is everywhere right now, but what actually matters for fundraisers? Bryan and Greg discuss how AI is showing up in fundraising, the tasks it can take off your plate, and the judgment call every fundraiser has to...

What if you could build the perfect fundraiser? What qualities would they have? Stronger asks? Better scripts? More confidence? Maybe. But the real superpower might be something far simpler: listening. In this episode...

You’re launching a capital campaign. The vision is clear. The excitement is building. But who’s protecting the owner? In this episode of Just Ask – Rethinking Development, Greg tackles a question many nonprofits...

Have you ever experienced the frustration of a campaign goal increasing after your feasibility study was complete? What went wrong? In this episode, Greg shares the single most important estimate that determines whether...

Some development leaders wait for direction. Others go the extra mile. What makes the difference? In this episode, Bryan and Greg explore a mindset shift that changes how development leaders approach their work — and...

Do fundraisers really care about donors—or just the donation? Bryan challenges a common assumption that fundraisers are driven by need, not stewardship—and explains why that mindset gets philanthropy wrong.

Ever wish you could go back and give your younger fundraising self a few pointers? Greg and Bryan unpack the insights, the pitfalls, and the practical advice they’d offer any new fundraiser stepping into the field.

Behind every transformational gift is a donor wondering whether the vision is real and their investment will matter. In this episode, we unpack the simple questions that build confidence—and keep campaigns from stalling.

Fundraising is full of familiar phrases—but some might be past their prime. In this episode, Bryan and Greg swap stories, share mild rants, and explore the words and clichés that feel tired, stale, or overused in...