On October 16, 2016, Mickey Z. started walking the streets of New York City with food, supplies, and gift cards to hand to homeless women. He noticed something first: homeless men will often walk right up and ask for a dollar, while women, already pushed to the margins, tend to sit quietly with a sign and wait. Those women became his teachers. They told him what they needed, what size to buy, what actually helped. Nearly ten years later, Cheerful Giver NYC has grown into a seven days a week mission serving anyone who asks, and Mickey has stopped calling it a project. He calls it a calling.

This one got personal for Nicole. She admits on air that she used to be braver, that she once struck up a conversation with a homeless woman in Chicago about the book she was reading, and that somewhere along the way she lost the entry point. So instead of interviewing Mickey, she asks him for help. What follows is a practical, grace filled conversation about the first words to say, why gift cards work, what to do when you get it wrong, and how to stop separating the person with the sign from everyone else you meet all day long.

In this episode:

  • Why Mickey started with homeless women, and what nearly ten years of hands on giving has taught him about earning trust
  • How a sign functions as an invitation, and why he will not approach someone who has not extended one
  • Nicole's honest confession about losing her courage, and Mickey's response to the question of where a person even begins
  • The Carnegie Hall regular who told him that one person's eye contact erases the thousand people who walked past
  • Why a fifteen dollar fast food gift card buys far more than a meal: a bathroom, a phone charge, a seat indoors, and the dignity of blending in
  • The mythology around giving cash, and the double standard we apply to how vulnerable people spend money

About Mickey Z.

Mickey Z. is a writer, longtime New Yorker, and the founder of Cheerful Giver NYC, a street level mission providing food, supplies, and gift cards to homeless people and other vulnerable souls across New York City. Born and raised in Queens, he began the work in October 2016 with a focus on homeless women, then expanded during the pandemic lockdowns to serve anyone within walking distance of his Astoria neighborhood who asks for help. He is the author of multiple books, has written for and volunteered with the homeless produced newspaper Street News, and writes regularly about giving, faith, and compassion on his Substack. He was named a Queens Person of the Week by NY1 for his work. He would like you to know he is not an expert.

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