Purpose & Profit Club® – The Nonprofit Fundraising & Marketing Podcast · Christina Tzavaras Edwards

175: Fear & Fundraising: How to Make Major Gift Asks That Don’t Scare You with Nathan Ruby

·34 min·2 clips

Social rejection activates the same brain regions as physical pain, including the anterior cingulate cortex.

Nathan Ruby sits down for an honest conversation about major donor asks and the nerves that often come with them. The episode begins with the basic tension of fundraising work: mission-driven people are asked to request large sums of money from other people. That alone can make the whole exchange feel heavier than it needs to be. From there, the discussion turns to the cultural habit of not talking plainly about money. People project onto wealth, success, and status because they rarely get the full picture. A fancy car can look like proof of plenty. It usually is not. The conversation uses that example to show how fast people build stories without facts. Nathan and the host then connect that discomfort to childhood money patterns. They talk about what it means when money was discussed openly at the dinner table versus kept tense or hidden. Nathan shares that his father was an entrepreneur, so cash flow, profit, expenses, and investment were normal family conversation. He also notes that his dad was a car dealer, which made money talk especially concrete. That background shaped how he thinks about money and risk. The episode also returns to the emotional side of asking. A donor conversation can feel intimidating not just because of the amount, but because it asks the fundraiser to tolerate uncertainty. The host frames that as a body-and-brain problem, not just a skill gap. The discussion keeps pushing toward clarity. Ask directly. Do not apologize for the mission. Do not make the donor guess. Another recurring idea is that asking is a practice, not a one-time performance. You may have to ask again. And again. The episode treats that repetition as part of the job, not a flaw in it. Nathan's advice is plainspoken and steady rather than polished or theoretical. The conversation is strongest when it names the excuse, strips away the story, and replaces it with a simple action. It lands on the idea that silence costs more than the ask. It also suggests that confidence grows from repetition, not from waiting to feel fearless. The tone stays warm, but it does not soften the challenge. Fundraisers are expected to step into discomfort and keep going. That is the work. The episode closes by reinforcing that the real loss is not an awkward moment. It is failing to make the request at all.

As heard by us

A practical look at making major asks without freezing.

This episode stays close to the nerves and habits that make major gift fundraising hard in practice. The host and Nathan Ruby treat money talk as a real source of friction for nonprofit leaders, including the projections people make about one another and the discomfort that can…

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Need to ask for major gifts without spiraling first?

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