In this episode, David Chambliss gets into the part of fundraising most people secretly dread: actually asking for the gift, living with the number you chose, and staying present when donor conversations get weird, emotional, or way too personal.

David and Tom unpack how to frame solicitations as invitations to invest in impact, not desperate cash grabs, and why under-asking can be more disrespectful than naming a bold, well-reasoned number. David shares the story of an early-career ask that was accepted so quickly the donor immediately asked whether he should have been asked for more, and what that taught him about preparation, capacity, and timing.

They also explore why the best cultivation you will ever do is excellent stewardship of past gifts. From a last-minute scholarship recipient surprise that left a campaign committee in tears, to donors meeting the actual “end product” of their giving, you see practical ways to make impact concrete in any size shop, without a big events budget.

Finally, David talks candidly about the human side of this work: donors oversharing, awkward living room moments, being pulled into family drama, and learning to respond with empathy without losing your professional boundaries.

You will hear practical takeaways that apply whether you are at a flagship university or a three-person nonprofit:

• How to reframe “asking for money” into inviting investment in a specific impact.
• A smarter way to size your ask so you do not unintentionally lowball a committed donor.
• The role of timing and patience in major gifts, and why some prospects only convert years later.
• Why great stewardship is your most powerful cultivation strategy for the next gift.
• Simple, replicable ways to put donors in front of real lives changed, even in small organizations.
• How to stay grounded when donors overshare, vent, or test your boundaries in awkward conversations.
• What it looks like to be fully human with donors while still representing your organization well.

If you have ever walked out of a solicitation replaying every word or wished you had handled an awkward donor moment differently, this episode will feel uncomfortably familiar and strangely encouraging.

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