Let's be honest
Fundraising often feels like trying to sound confident while quietly holding a sign that says, “Please help.”
You need support—yet the second you sound too needy, you lose strength. And if you sound too successful? Donors wonder, “So why do they need me?”
This tension trips up even seasoned fundraisers.
I felt it myself—until I came across a golden nugget from veteran coach Lori Jacobwith. I tried it, loved the results, and now I want you to try it too.
She calls it your Money Story—a simple, healthy way to talk about your financial needs so donors understand how to help you and feel good doing it.
Here’s how to create one, in six clear steps:
Step 1. Give your donors clarity.
Start with a snapshot of your big-picture financial status:
your goal, what you’ve raised so far, and what’s still needed.
“This year, we’re working to close our funding gap of $900k. As of now—Dec 7th—we’ve raised $775,000 toward that goal.”
Clarity builds trust.
Step 2. Zoom in.
Now that your donor understands the big picture, focus on one meaningful area of impact within your work — a part of your organization where support makes a real, tangible difference.
Choose something with a clear purpose and a clear cost.
For example:
“Our yeshiva's mentoring program gives rebbeim a place to refer bochurim who need focused guidance, confidence-building, and one-on-one attention.”
This is the moment to move from general need to a specific part of your mission — something the donor can easily grasp.
And once you’ve highlighted that area of impact, you’re ready for the next step:
showing why it matters.
Step 3. Share a People Story.
Programs make sense.
People make impact feel real.
Once you’ve highlighted the area of impact, bring it to life through the story of someone who was touched by it.
Numbers inform; stories inspire.
Here’s a real example:
“Let me make this real for you. I want to tell you about Moshe.
Moshe is an 8th-grade bocher in our yeshiva — bright, sensitive, full of potential. But this year began with real struggles. He fell behind in class, stopped raising his hand, and quietly convinced himself that maybe he ‘just isn’t a learner.’ His parents saw the change. So did his rebbe.
Rabbi Stein noticed what others had missed. Moshe understood more than he realized — he just froze when called on. His silence wasn’t apathy; it was fear. And beneath it all was a bocher who wanted to succeed but didn’t know how to begin.
So Rabbi Stein connected him with our yeshiva’s own mentoring program — a built-in support system that gives boys like Moshe the time, attention, and confidence they need to shine.
Moshe began learning twice a week with a mentor. Slowly, something shifted. He stayed after school to review “just one more time.” A few weeks later, he raised his hand in class — the first time all year.
And the day before the Pesach break, he told his rebbe:
“Rebbe… this is the first time I ever felt like I can really learn.”
That single sentence captures why this mentoring program matters.”
Step 4. Quantify the gap—gently.
Once the story brings the work into focus, your donor is emotionally connected.
Now make the need clear.
Not dramatic. Not heavy-handed. Simply specific.
“This mentoring program costs $8,000 per bocher per year. Right now, we’re still short about $72,000.”
When you quantify the gap in simple, human terms, your donor can immediately see the opportunity — and the role they could play in closing it.
Step 5. Signal that the need continues.
Closing this year’s gap matters — but it’s not the end of the story.
Every year, more rebbeim identify boys who would benefit from mentoring, and the need inside the yeshiva continues to grow.
“We already have several boys Rabbi Stein wants to bring into the mentoring program next semester — bochurim who just need the right support to thrive.”
Now your donor sees both the immediate need and the longer-term vision:
a yeshiva where every boy has the chance to shine.
Step 6. Make the ask — with confidence and warmth.
By this point, your donor understands the
heart, the numbers, and the impact.
Invite them to step forward — with clarity and respect.
“Would you consider a gift of $10,000 to help close this gap and ensure that every bocher who needs a mentor can have one this year?”
A strong ask includes:
- A specific amount.
Clarity is kindness. - A clear purpose tied directly to impact.
Their gift sponsors real mentoring for real boys. - A tone of partnership.
You’re not taking from them — you’re giving them the opportunity to help a child succeed.
Then pause. Let the moment work.
When a donor is already emotionally connected and understands the practical need, a warm, confident ask feels natural — because it’s the next honest step in the conversation.
When you bring all six steps together, something powerful happens:
your donor feels connected, informed, and invited into real partnership.
That’s the heart of a great Money Story.
Consider this Money Story a power-tool in your fundraising toolbox.
Use it well, and you’ll see your fundraising become clearer and easier.
So — who do you plan to share your Money Story with this week?
Have a fabulous fundraising week,
Avraham
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