Taking Deeper Dives

Hi Reader,

I want us to be relentlessly positive this year while still being realistic. Do you think that's possible? To help, this issue contains the following:

• A model from Missouri to share child care costs.
• AI prompts to help you fully explore an issue or uncover important data about your beneficiaries.
• A couple of notes about clever fundraisers.

Child Care Works (Missouri) is operating an innovative cost-sharing (“tri-share”) model designed to lower child care costs by splitting them across the state, employers, and families—targeting families who don’t qualify for federal subsidies but still struggle with affordability. One report describes a $2.5M state allocation and a target of up to ~450 seats (capacity appears to be evolving as the rollout continues). It’s a structural financing innovation—treating child care like shared infrastructure rather than an individual household burden, with employers participating as a retention/workforce strategy. This project could become a model for other states, since all states are currently struggling to help families in need.

Explain Three Times

The Neuron asks the question, "Every feel like you're speaking alien to your AI? . . . Ask ChatGPT or Claude to explain any complex concept three different ways—for a six grader (or kindergartener, if you want a really simple version), a college student, and a domain expert." Here's a prompt, modified from that newsletter's original:

PROMPT: Explain [complex concept] three times: (a) to a 12-year-old (b) to a college student (c) to a domain expert who wants edge-case caveats. For each, provide at least two similes, metaphors, or stories that drive home the explanation.

(From The Neuron, May 7, 2025.)

Go Deep on a Topic

If you want to truly explore an idea, use AI as your partner:

PROMPT: Generate a list of thought-provoking, open-ended questions about [topic] that stimulate deeper critical thinking and exploration. Focus on questions that challenge assumptions, reveal nuances, and encourage further inquiry into the subject.

(Adapted from Superhuman, July 17, 2025.)

Know Your Beneficiaries Better

PROMPT: Act in the role of a customer research expert. My "customers" are nonprofit beneficiaries of my nonprofit's programs, which you should learn about at [nonprofit's URL].

I want to know 10 frustrations, 10 deepest desires, 10 hidden thoughts, 10 past failures, 10 burning questions, 10 common enemies and 10 fears that my target customers experience that relates to [What you want to talk about, provide as many details as possible]. Do the above while mentioning the awareness level of that group of audience in detail.

(Adopted from Superhuman, July 3, 2025.)

Actor Nick Offerman parted with his most iconic feature—his Ron Swanson mustache—for charity. Offerman shaved off his famous Parks and Rec lip hair, glued it back into its original shape, mounted it, and auctioned it off to benefit Because of Ezra, a pediatric cancer charity. It was a bittersweet sacrifice (“like selling a sacred relic,” he quipped), but the privately auctioned mustache fetched a handsome donation for the cause.

70 Skydives on 70th Birthday—Most people celebrate 70 with cake; Larry Ekstrom celebrated by skydiving 70 times in one day. The Michigan man marked his milestone birthday by doing 70 jumps to raise money for Leader Dogs for the Blind. He’d done 60 jumps on his 60th for charity too—and this time, at 70 years old, he completed all seventy skydives within 10 hours, raising funds and proving age is just a number when helping others.

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Ted

Founder and CEO Risk Alternatives, LLC 202.758.7572 (cell) 608.709.0793 (office) Website​ Author of ​​Managing Your Nonprofit for Resilience​​​ We help nonprofits thrive by providing practical tools and support to address uncertainty and improve risk management.

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