NestPilot retirement decision tools are coming to ChatGPT

Today we submitted NestPilot to the OpenAI ChatGPT Apps SDK. Once OpenAI completes review, anyone using ChatGPT will be able to invoke our retirement-decision tools without leaving the conversation — no signup, no installation, no separate website visit.

This is the same Foundation mission, distributed where people already are.

What the ChatGPT app does

Four tools, all anonymous, all educational, all free:

• Medicare timing — Initial Enrollment Period and Special Enrollment Period guidance for users approaching 65 or still working past 65.
• Social Security claiming-age comparison — side-by-side comparison of claiming at 62, FRA, and 70 from a single FRA-benefit number.
• Roth conversion candidacy — a directional assessment of whether a household is a good Roth conversion candidate based on age, income, and pre-tax balances.
• Retirement-age viability — comparison of candidate retirement ages with a simplified drawdown model.

These match the same wedge content we publish here at www.nestpilot.org — just delivered inside a ChatGPT conversation as interactive widgets instead of a website page. The math is identical. The privacy posture is identical. The Foundation 501(c)(3) commitments — no products sold, no data sold, open methodology — are identical.

Watch the 4-minute demo

This is the same submission video OpenAI's review team sees. It walks through each of the four tools end-to-end, plus a few cases that should not trigger the app (the scope-discipline part of any responsible AI tool).

4 min 35 sec · 1920×1080 · Direct MP4 (8 MB)

What you can do today (while we wait for review)

The four ChatGPT tools wrap the same calculations we publish here as anonymous, no-account-needed web pages. If you want to start using them now, you don't have to wait for the OpenAI rollout:

• Medicare enrollment deadlines — and the 3-minute Medicare Enrollment Guardian wizard
• Social Security claiming ages
• Roth conversion basics
• 2026 IRMAA brackets
• Or jump straight to the four anonymous calculators at /tools

Everything we ship on ChatGPT will continue to be available here too. The ChatGPT distribution is additive — same Foundation, just reaching more people.

Why this matters for the Foundation mission

The biggest barrier to retirement-decision literacy isn't math — it's reach. Millions of Americans approaching 65 make irreversible Medicare, Social Security, and Roth-window mistakes every year, simply because there's no neutral, fiduciary-aligned source meeting them where they already are. ChatGPT meets them where they are.

A 501(c)(3) public charity distributing free, anonymous, math-backed decision support inside the largest AI assistant in the world — at zero marginal cost to the user, with zero financial-products incentive — is the most direct expression of our charter we've found so far.

What's next

OpenAI's review typically takes a few weeks. When the app goes live, we'll post here. If you want to be notified, follow the RSS feed.

If you're a developer or a tester with ChatGPT Apps SDK Developer Mode access and want early-access to test the integration, reach out — we'll add you to the developer-mode allowlist.