157: Old Woman Shakes Fist at Sky | How Classy May Be Hurting Your Donor Relationships

157: Old Woman Shakes Fist at Sky | How Classy May Be Hurting Your Donor Relationships

Author: Jess Birken, MNM, JD February 5, 2026 Duration: 20:31

Nonprofit newsflash - your donation platform might be quietly annoying your biggest donors 😬

In this episode, Meghan and I dig into some nonprofit LinkedIn drama sparked by a post from the one and only Eve Borenstein. Here's the situation:

You gave a big donation, and you received an auto-generated donation receipt from the org's donation platform. The problem?  The gift acknowledgement letter and receipt are WRONG.  

We break down why donor acknowledgement letters matter so much, what the IRS actually requires in those receipts for gifts over $250, and how automated systems can unintentionally damage donor trust. We also talk about the growing trend of for profit software companies promising to "handle everything" for nonprofits while missing critical compliance details. If you rely on online donation platforms, this conversation will likely make you rethink what you are outsourcing and what still needs human attention.

What You'll Learn:

  • What SHOULD be in your donor acknowledgement letters
  • How bad receipts can create donor frustration
  • Where donation platforms and tech solutions for nonprofits can fall short
  • How automation can quietly hurt your donor retention

Bottom line: Donor relationships are built on trust and gratitude. When your systems create friction instead of appreciation, even unintentionally, it can cost you future support and credibility.

Resources from this Episode

Connect with Us

Listen & Engage

Stay Connected


Ever find yourself wishing for a direct line to seasoned nonprofit leaders, a chance to unpack the real challenges that don’t make it into the glossy annual reports? Charity Therapy is that conversation. With host Jess Birken, who brings her background as a lawyer and a Master of Nonprofit Management to the table, each session feels like pulling up a chair with a trusted advisor. The discussions move beyond theory, tackling the granular details of operations that leaders actually face-whether it’s navigating a tricky IRS compliance question, rebuilding a fundraising strategy from the ground up, or managing the complex interpersonal dynamics that define any mission-driven team. This podcast digs into the operational heart of the sector, offering pragmatic insights you can apply directly to your own work. It’s a resource built on the understanding that running a nonprofit is a continuous practice of problem-solving, and Jess guides these explorations with clarity and a deep respect for the work. Tune in for honest dialogue that treats the daily grind of management as the serious and nuanced craft that it is.
Author: Language: English Episodes: 100

Charity Therapy
Podcast Episodes
Welcome to Charity Therapy! [not-audio_url] [/not-audio_url]

Duration: 4:01
What if you could hang out with experienced nonprofit professionals and ask them your burning questions about the day-to-day life of nonprofits? What if you could take their wisdom and bring it back to your organization,…
091: My Life the Musical [not-audio_url] [/not-audio_url]

Duration: 23:21
Hey there! We are back again, and this time we're delving into the nitty-gritty of growing a small team in the nonprofit sector. We've been through the ups and downs of growing our own team at Birken Law Office, and we'r…
090: The Wisdom of a 14-Year-Old [not-audio_url] [/not-audio_url]

Duration: 20:25
It's me again--ready to challenge what you think you know about the nonprofit sector. In this episode, I invite my guest - my 14-year-old - Max, to take a deep dive into the world of nonprofit boards. We're pulling back…
089: Midwestern Shame Spirals [not-audio_url] [/not-audio_url]

Duration: 17:54
In this episode of Charity Therapy, Meghan and I dive into the often-misunderstood world of conflicts of interest in nonprofits. What is a conflict, really? Is it a terrible, horrible, egregious situation to be avoided a…
Hitting the Hail on the Ned [not-audio_url] [/not-audio_url]

Duration: 15:54
When you think about nonprofits, lots of different things come to mind - missions and visions, fundraising, hard-working staff, and strong communities. But do you know what most folks don't think of? Efficiency. Today, M…
Money, Money, Money [not-audio_url] [/not-audio_url]

Duration: 19:35
In this episode of Charity Therapy, Meghan and I tackle another fundraising question - this time about dealing with difficult donors. This episode is a prime example of why it's SO important to stay focused on your organ…
Don't Sue Each Other! [not-audio_url] [/not-audio_url]

Duration: 21:41
Everyone wants to be an insider, right?! Well for nonprofits, that "insider" label can make things a little more complicated. Conflicts of interest have entered the chat! Can board members be hired to be the org's Execut…
One Giant Blooper [not-audio_url] [/not-audio_url]

Duration: 17:49
Join us in the restricted section for the episode – the restricted gifts section, that is! Today, Jess and Meghan break down what a restricted gift is and what exactly it means for your financials to accept one. What hap…
Fighting to the Death for Some PTO [not-audio_url] [/not-audio_url]

Duration: 21:18
Organizational culture is what gets created when we're busy doing EVERYTHING else. So, what do your fundraising practices say about your culture? We pulled this episode from the backlist because it deserves another momen…
Magic Wands & Shiny New Toys [not-audio_url] [/not-audio_url]

Duration: 20:21
Talking about fundraising can be overwhelming and FULL of jargon – but not when Patrick Kirby does it! Today we're joined by Patrick of Do Good Better Consulting to answer your nonprofit fundraising questions. How do we…