Nonprofit Lowdown Episode #352: Year End Giving Prep with 10x Crew

Released: August 25, 2025

Overview: Year-End Fundraising, AI, & Authentic Donor Connection

In this dynamic roundtable discussion, host Rhea Wong convenes her "10x Chromosomes Crew"—a powerhouse group of nonprofit thought leaders and practitioners—to share the most effective strategies for nonprofit year-end fundraising. Together, they explore how to blend proven fundraising principles with emerging tools like AI and automation, while emphasizing the enduring value of personal, authentic donor relationships. The episode is full of actionable advice, practical tech suggestions, and candid reflections on the evolving fundraising landscape in 2025.

Guests:

• Cindy Wagman
• Jess Campbell
• Rachel Bar
• Tanya Bhattacharya
• Kel Haney

Key Discussion Points & Insights

1. Preparing for Year-End: Groundwork & Tech (00:33–05:03)

• Year-End Importance: Rhea sets the stage by noting that around 30% of annual nonprofit revenue often arrives in the last week of the year, amplifying stress and urgency for fundraising teams.
• Small Shop Realities: Many nonprofits operate with tiny teams, so efficiency and clarity of focus are paramount during year-end.

Cindy Wagman’s AI Storytelling Hack (02:21):

“So my little AI hack is I interview for stories on Zoom… I take that transcript…and plug that into a custom GPT within Claude... But the way to make it even better is to really train that GPT...use past letters that have performed well as the knowledge base.” —Cindy Wagman (03:44)

• Practical Tip: Leverage story-based fundraising by using AI tools (preferably Claude over ChatGPT for writing) trained on your own successful past appeals to develop first drafts.

Rachel Bar’s Tech Stack Audit (03:44–05:03):

“Get your tech stack in order... Make a list and go through and just make sure that things are connected and things are integrated.” —Rachel Bar (04:07)

• Action Item: List and review all elements of your tech stack (CRM, email, fundraising platform, automation tools like ChatGPT/Claude, etc.) to ensure proper integration before launching end-of-year campaigns.

2. The 2025 Fundraising Climate: Trust, Transparency, & Donor Segmentation (05:03–13:09)

• Changing Landscape: Rhea notes a challenging year with declining donor trust, federal funding cuts, inflation, and economic volatility. Only major gifts are consistently growing as a donor segment.

"If it feels like it's been a little bit harder this year, you're right. It has been a little bit harder." —Rhea Wong (05:03)

Kel Haney on Micro-Connection and Mid-Level Donors (06:31)

“What I'm really seeing is that micro connections over the phone… work well for mid-level donors, predominantly.” —Kel Haney (06:52)

• Practical Insight: Five-minute, personal phone calls can lead to extraordinary mid-level donor upgrades and long-term commitments.

Tanya Bhattacharya on Building Trust via Personal Storytelling (07:57)

“On LinkedIn, when individuals share, it has 561% greater reach than an organization's LinkedIn content ever will… This is a great opportunity to get the people behind your mission sharing their deeper ‘why’.” —Tanya Bhattacharya (08:56)

• Trust Perspective: Nonprofits are trusted more than other social institutions; authentically showcasing the humans behind the mission (staff, board, volunteers) amplifies trust and reach.

3. AI & Automation: Tools, Challenges, and the Human Factor (13:09–16:10)

• AI as Support, Not Replacement: Rhea frames AI as freeing staff for “human” work, not as a full substitute.
• Train Your AI: Ensure your AI tools are trained on your organization’s actual voice and messaging for best results (see show notes templates).

“If you haven't created the inputs and trained your AI, it's going to sound generic… The more you can train AI to sound like you, the more you can delegate to it. Think of it as a really smart intern.” —Rhea Wong (13:10)

• Automation & Trust: Automations—immediate acknowledgements, streamlined donor touchpoints—are now expected and help build donor trust, but must be tempered with authentic human connection (Cindy Wagman, 13:52).

4. Zigging When Others Zag: Analog Outreach in the Digital Age (16:10–17:39)

• Standing Out: Because AI and automation are ubiquitous, analog methods (handwritten notes, personal phone calls, physical mail) can dramatically increase engagement.

“How you get noticed then is going analog… I think what we see working in the algorithms is, for better or for worse, FAST is better than perfect… People are responding to authenticity.” —Rhea Wong (16:10)

• Snail Mail Innovations: Magazine mailings and personal touches are making a comeback as effective ways to cut through digital noise.

5. Back to Basics: The Case for Planning and Touchpoint Mapping (17:39–20:46)

Jess Campbell’s Internal Audit Challenge (17:39)

“Do a bit of an internal audit…when was the last time I communicated impact to my 2024 end-of-year donors?” —Jess Campbell (18:06)

• Start Simple: Before getting lost in tech solutions, map out previous communications and gratitude touchpoints for each donor segment.
• Fix Gaps: Many orgs only reach out for asks, not for stewardship—use your short window before year-end to change this perception.

6. Calendaring, Goal Setting, and the Power of Matching (20:46–24:16)

Kel Haney on Working Backwards (20:46):

“Work backwards from what you want accomplished when you come back into the office in January… Most of the clients…don’t actually have active goals set specifically for individual giving, which breaks my heart.” —Kel Haney (21:25)

• Specificity Wins: Quantify your goals and be transparent with supporters to engage both their empathy and action-oriented instincts.

• Matching Gifts Magic:

“Matches are magic. Matches are magic. Matches are magic.” —Kel Haney (23:35)

• Strategy: Secure major gifts early, use them for matching gift campaigns (e.g., Giving Tuesday), and segment approaches for maximum effect.

7. Major Donors & The 80/20 Rule (24:16–26:50)

• Don’t Neglect the Board: Board members are often your biggest donors and should be stewarded, not just solicited for contacts.
• Launch with Strength: Secure 20–50% of campaign gifts from major donors before public launch for credibility and momentum.

"Every campaign is 80/20; 20% of the gifts will make up for 80% of the overall." —Rhea Wong (24:27)

• Major Donor Timing: Big gifts often come outside of year-end tax deadlines; focus on relationships, not just deadlines.

8. Email: Getting Cadence and Content Right (27:49–32:11)

Jess Campbell’s Email Best Practices

“If you haven’t spent your year communicating via email, it is going to be difficult…to suddenly start sending between 12 and 16 emails in a 30 day period… But the data shows that the more you ask, or the more you communicate, the more money you get.” —Jess Campbell (28:24)

• Cadence: If you’re starting late, ramp up gradually with story-rich, valuable emails at least weekly; people donate via email more than any other channel.
• Volume Guidelines:
  • Giving Tuesday: More than one email needed (some orgs send up to 8!)
  • Last 3 Days of Year: Up to 5 emails, especially on December 31st
  • Personalization: Entertain and connect; bad emails lead to unsubscribes.

“Just because you have an overflowing inbox...doesn't mean that is happening for your subscriber.” —Jess Campbell (29:40)

9. The Role of Phone Calls in Campaigns (32:11–36:09)

Kel Haney on Phone Calls (32:46):

“Phone calls and emails go together like peanut butter and jelly… People say they don't like phone calls because they are not getting good phone calls.” —Kel Haney (32:50)

• Make Calls Great: Quality, human conversations (not monologues or scripts) yield ROI and deepen loyalty.
• Timing: Call even on busy dates—December 31st is habitually big for some.
• Integration: Phone strategy must sync with email and other communications.

Rachel Bar on Having a Plan:

“Make sure you know what you're gonna say before you call a donor...both of us were like, it was the most awkward call in like kind of the most wonderful way too.” —Rachel Bar (35:28)

10. Automating Donor Stewardship (36:50–39:33)

Rachel Bar’s Favorite Automation:

“My most favorite automation is setting up a draft thank you note… when somebody donates a draft email lands in your inbox so all you have to do is go in…they just want to be seen.” —Rachel Bar (37:45)

• First-Time Donor Sequence: Automate reminders and draft communications to promptly thank and nurture new donors.
• Task Assignment: Use your CRM to auto-create follow-ups for staff/board members.

Notable Quotes & Memorable Moments

• On AI and Authenticity: “There's so much mistrust…because people are being more careful around their giving… I want to use the technology…I don't want to sound like a robot.” —Cindy Wagman (09:30)
• On Human Connection: “Conversations mean that there's two people… it's not a monologue.” —Rhea Wong (36:09)
• On Emails: “When your emails are good and entertaining, people tell me all the time they look forward to my emails. And so I send a lot of emails. So just try that.” —Jess Campbell (31:56)

Episode Structure & Timestamps

• Tech stack & story-based AI hacks: 02:21–05:03
• Fundraising challenges in 2025: 05:03–07:57
• Trust & transparency: 07:57–10:43
• AI, automation, and brand voice: 11:58–16:10
• Standing out with analog methods: 16:10–17:39
• Communication audit & donor segmentation: 17:39–20:46
• Goal setting & calendaring: 20:46–24:16
• Major gift strategies: 24:16–27:49
• Email campaign strategies: 27:49–32:11
• Phone calls & conversational fundraising: 32:11–36:09
• Donor stewardship automations: 36:50–39:33
• Rapid-fire wrap-up/recap: 39:33–40:37

Key Takeaways & Action Items

• Audit & Plan: Review your tech stack, current donor communication patterns, and gaps in stewardship before launching automation or AI.
• Embrace AI as a Tool: Use AI to speed up and tailor content creation, but train it in your unique brand voice and tone.
• Communicate Proactively: Ramp up donor touchpoints (mix of email, phone, and analog mail), especially in the months leading into the campaign.
• Prioritize Major Gifts: Secure large donations pre-launch; be strategic about matching campaigns.
• Automate with Care: Leverage automations for speedy acknowledgements but retain heartfelt, individualized touches.
• Be Human: Donors respond to authenticity, adaptability, and personalization—apply these principles in all outreach.

Final Words:

“Take care of your major donors right now because they are going to make up the bulk of the money that you’re bringing in through the end of the year...go forth and be friends with AI. Don’t be scared.” —Rhea Wong (40:37)