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

Purpose & Profit Club® – The Nonprofit Fundraising & Marketing Podcast

Purpose & Profit Club® – The Nonprofit Fundraising & Marketing Podcast
175: Fear & Fundraising: How to Make Major Gift Asks That Don’t Scare You with Nathan Ruby
Dec 09, 2025 Season 1 Episode 175
Christina Tzavaras Edwards

Major gift fundraising is where many nonprofit leaders freeze, but not because they lack passion or skill. The fear lives in the body, the brain, and the stories we tell ourselves long before we walk into the room.

In this episode, I’m joined by Nathan Ruby, Executive Director of FOTCOH (Friends of the Children of Haiti), one of the rare EDs who has raised millions of dollars from individual donors, not foundations. Nathan brings 20+ years of experience in major gifts, donor psychology, cross-cultural fundraising, and what it actually takes to have confident, courageous donor conversations. Together, we discuss the neuroscience behind fear and rejection, how imposter syndrome shows up during big asks, why culturally we struggle to talk about money, and why donors actually want us to be honest and direct. If you struggle with fear, freezing, or overthinking around major gift asks, this conversation will change how you fundraise forever.

Topics:

  • Why major gift fear is not a personality flaw,  it’s neuroscience
  • How to reframe donor conversations by focusing on the people you serve
  • Why donors are used to talking about money (and why you don't need to be scared)
  • The science behind rejection and why “no” activates the same regions as physical pain
  • Nathan’s background in sales and how it shaped his fearless fundraising mindset
  • How to use donor questions to inform the right ask amount
  • Why genuine honesty is more magnetic than a perfect pitch
  • Why your donors want you to win and how to invite them into partnership


For a full list of links and resources mentioned in this episode, click here.

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