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HBO and The Ringer's Bill Simmons hosts the most downloaded sports podcast of all time, with a rotating crew of celebrities, athletes, and media staples, as well as mainstays like Cousin Sal, Joe House, and a slew of other friends and family members who always happen to be suspiciously available.
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What separates a good fundraiser from a truly transformative one? In this episode, Kyle sits down with Rachel Simon, MBA, MS, CFRE , a powerhouse in the world of community impact and philanthropy, to unpack how authentic relationships, deep trust, and shared purpose can turn fundraising into a movement for change.
Rachel shares her journey from early career challenges to leading record-breaking campaigns that didn’t just raise money, they rebuilt confidence, culture, and connection within entire communities. Together, she and Kyle explore what it really means to lead with empathy, create donor partnerships rooted in trust, and sustain generosity even in uncertain times.
If you’ve ever wondered how to inspire people to give, not out of obligation, but out of belief, this episode is your blueprint.
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