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Progress report: an expanded board and a more transparent nestpilot.org
A mid-summer progress report from a young foundation. Since June — a five-director board with independent oversight, a published founding timeline with links to verify our 501(c)(3) status independently, a faster and more accessible site, and a look at what's next for the education library and community seminars.
Read postNestPilot is now live in ChatGPT
As of June 3, 2026, NestPilot's free retirement-decision tools are live inside ChatGPT — available to all ChatGPT users, including the free tier. Enable the app once, then ask ChatGPT about Medicare enrollment timing, Social Security claiming, Roth conversions, or retirement-age viability and get the same anonymous, math-backed decision support that lives at nestpilot.org. Here's how to enable it and what each tool does.
Read postNestPilot retirement decision tools are coming to ChatGPT
We've submitted NestPilot to the OpenAI ChatGPT Apps SDK. Soon, anyone with ChatGPT will be able to ask about Medicare enrollment timing, Social Security claiming, Roth conversions, or retirement-age viability — and get the same anonymous, no-products-sold decision support that lives at nestpilot.org, rendered right inside the conversation. Watch the 4-minute demo we sent to OpenAI.
Read postThe 5 retirement decisions that cost $30K-$300K each
Most retirement-wealth loss doesn't come from budgeting mistakes. It comes from a small number of irreversible decisions made in narrow windows. Here are the five with the highest lifetime cost, what each one costs to get wrong, and where to find the free anonymous tools that explain each window.
Read postFoundation tools now live at www.nestpilot.org
Wave 2 of the Foundation site rollout is complete. The four wedge-content references, four anonymous calculators, and the Medicare Enrollment Guardian are now hosted at their canonical home on www.nestpilot.org. The authenticated planning app moves to app.nestpilot.org.
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