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.

Help Shuvu grow

This episode is sponsored by:

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► Amudim - What Comes Next, Live in New York

Join Nachi Gordon moderating a powerful panel on healing from abuse, crime, and trauma. Free event, limited seating.

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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

Rabbi Benjamin Goldschmidt grew up in Moscow as the son of the city's chief rabbi, trained in Bnei Brak and Ponovezh, and spent a decade as assistant rabbi at Manhattan's Park East Synagogue — until he was abruptly and very publicly fired. In this raw conversation with Nachi Gordon, he opens up for the first time about that moment: the New York Post headline, the car crash he got into reading about himself, and the isolation of losing not just a job but an entire community.

Out of that low point came Altneu, the congregation he and his wife built from nothing — starting with 40 people in their living room, then two and a half years of renting a different Manhattan venue every single week, never knowing until Thursday's email where Shabbos would be. Rabbi Goldschmidt walks through how that instability became the shul's strength, the breaking point that nearly ended the project, his father's advice that turned it around, and how it all led to buying a $35 million building on the Upper East Side. He also gets into what it's like leading a congregation through today's political climate in New York, and the loss of a beloved member that shook the whole community.

This episode is sponsored by:

► PZ Deals

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_________________

► Colel Chabad Pushka App

The easiest way to give Tzedaka

https://pushkapp.cc/meaningful

_________________

► Shopify Guru

Store looks great but not selling the way it should? Shopify Guru's Daniel gets under the hood and makes it actually work, no developer needed every time you want to make a change. Call 732-534-1404 or go to shopifyguru.io.

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► Ness Vacation Homes

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► El Al

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► Rothenberg Law Firm

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► Town Appliance

Visit the website or message them on WhatsApp.

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Timestamps:

0:00 Intro: A Shul With No Address

2:57 Growing Up in Moscow as the Chief Rabbi's Son

8:47 Sent to Bnei Brak and Ponovezh at Twelve

11:40 Choosing the Rabbinate and the Lakewood "Freezer" Years

18:28 Becoming a Rabbi at Park East at Twenty-Four

23:52 A Decade as Assistant Rabbi at Park East

26:52 Getting Fired: The Sudden, Public Fallout

33:47 Losing a Job, Losing a Community

36:19 His Father's Parallel Story and the Birth of Altneu

44:20 Building a Shul on Wheels Across Manhattan

54:48 The Breaking Point and His Father's Advice

59:05 Buying a $35 Million Building on the Upper East Side

1:01:28 Building Altneu's Identity and Culture

1:10:01 From the Pulpit to Politics: Life in Manhattan Today

1:17:50 Confronting Antisemitism and What Makes a Movement Survive

1:22:00 Remembering Wesley

1:24:37 Closing

Josh Livingstone is a husband coach who works almost exclusively with men, and in this episode he explains why so many well-intentioned husbands still leave their wives feeling unheard. He and Nachi unpack what he calls the real root of most marital friction: it's not a lack of communication, it's a failure to translate. Josh walks through the "headache test," the reason a wife asks her husband to do something 50 times, and why a woman getting controlling in a marriage is often a symptom of not feeling safe rather than a desire for power. He also explains why "I'm sorry you feel that way" is one of the worst things a husband can say, and lays out the right way to apologize: full ownership first, discussion second.

Josh shares stories straight from his coaching practice, including a wealthy client who was convinced a two-week trip to the French Riviera would fix his marriage, only to learn his wife just wanted a ten-minute walk around the block with him at night. He breaks down his four-step CORE method for turning insight into real change at home, and gets into why so many husbands were never actually taught how to show up for their wives in the first place. It's a candid, practical conversation about masculinity, leadership, and what it actually takes to make a marriage work.

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This episode is sponsored by:

► PZ Deals

Download the app and never pay full price again!

https://app.pz.deals/install/mpp

_________________

► Colel Chabad Pushka App

The easiest way to give Tzedaka

https://pushkapp.cc/meaningful

_________________

► Shopify Guru

Store looks great but not selling the way it should? Shopify Guru's Daniel gets under the hood and makes it actually work, no developer needed every time you want to make a change. Call 732-534-1404 or go to shopifyguru.io.

https://go.jcn.io/sgmp

_________________

► Ness Vacation Homes

EDEN GARDENS' LARGEST LUXURY HOME COLLECTION. Handpicked, high-end homes available exclusively through Ness.

https://nessvacationhomes.com/

_________________

► Rothenberg Law Firm

Personal Injury Law Firm For 50+ years! Reach out today for a free case evaluation.

https://shorturl.at/JFKHH

_________________

► Town Appliance

Visit the website or message them on WhatsApp.

https://www.townappliance.com

https://bit.ly/Townappl