August 29, 2026 Share
This week, Nachi Gordon sits down with philanthropists Yossi Hoch and Simcha Shain to talk about the world of tzedakah, from the pressure donors carry to the changing psychology of giving. They open up about what has shifted since their parents' generation, how technology and platforms like Charidy have reshaped fundraising, and why some of the most established organizations now struggle to compete with flashier, newer causes. Along the way they share candid stories about donors who quietly write six figure checks and others who give up their Shabbos soda money, and why both matter equally.
The conversation turns personal as Yossi and Simcha discuss the hidden shame that comes with losing the ability to give, the toll of unfulfilled pledges, and what it really means to give with a full heart rather than a full wallet. They also dig into Shuvu, the organization educating thousands of children across Israel, including former hostage Bar Kuperstein, and share the story of how each of them first got involved. It's a wide ranging, honest look at what tzedakah costs, what it gives back, and why every dollar, no matter the size, counts.
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Timestamps:
0:00 Intro: The $7 Postdated Check That Changed a Life
2:09 Meet Yosi Hach and Simcha Shain
3:38 A Billion Dollars a Year in Tzedakah
5:03 How Communal Wealth Has Changed
6:04 Technology's Impact on Fundraising
8:27 The Rise of Charidy and Online Giving
12:12 Donor Psychology: Has Giving Gotten Too Easy?
14:19 The Shrinking Value of $100
18:01 Can a Family of Five Live on $300K?
20:00 Tuition, Tax Credits, and Housing Costs
23:51 Advice for a 22 Year Old Starting Out
26:13 Investing in Yourself
29:35 Fundraising War Stories and the Hidden Stress on Donors
36:52 A Personal Story of Loss and Gratitude
39:17 Chesed, Unfulfilled Pledges, and Giving with a Full Heart
49:20 The Origins and Growth of Shuvu
55:19 Shuvu's Alumni, the War, and How Simcha Shain Got Involved
1:04:19 Mike Tress, Parting Advice, and Vetting a Charity
Aug 23, 2026