Start Here

Your intro to NestPilot

NestPilot helps you make the retirement decisions that cost $30,000 to $300,000 each when made wrong. Plain-English explanations, free anonymous tools, transparent math. We're a 501(c)(3) educational Foundation — free for everyone, always.

Prefer to read? Skip the video and jump to the 5 decisions →

Watch the 90-second intro

The cost of getting retirement decisions wrong, the free tools NestPilot Foundation provides, and the 501(c)(3) commitment — in ninety seconds.

Want depth? Watch the full 7-minute walkthrough below →

1. The 5 retirement decisions we focus on

Each one happens once or twice in a lifetime. Each has a window that closes. Each, when made wrong, costs tens of thousands to hundreds of thousands.

Read the full deep-dive

Medicare Part B enrollment
Cost of getting it wrong: $8K–$25K lifetime
Miss your enrollment window and pay a 10% premium surcharge for the rest of your life.
Learn more Medicare Enrollment Guardian
IRMAA bracket cliffs
Cost of getting it wrong: $1K–$5.8K / year
A single dollar of additional income can push your Medicare premium into a higher bracket for two years.
Learn more 2026 IRMAA brackets
Social Security claiming age
Cost of getting it wrong: $50K–$300K lifetime
Claiming at 62 vs. 70 is the difference of $50K-$300K in lifetime benefits, depending on your situation.
Learn more Compare claiming ages
Medigap underwriting window
Cost of getting it wrong: $20K–$80K lifetime
A 6-month one-time window after Medicare enrollment where you cannot be denied or charged more for pre-existing conditions.
Learn more Medicare enrollment deadlines
Roth conversion gap-years
Cost of getting it wrong: $50K–$200K lifetime
The years between retirement and required minimum distributions are the cheapest tax-planning window of your life.
Learn more Roth Candidacy assessment

2. Free anonymous tools — no signup

The fastest way to see if NestPilot can help you. No account, no email, no bank login. Every tool is free, anonymous, and educational.

Social Security Claiming Calculator — compare your benefit at every age from 62 to 70 with break-even analysis.
Roth Conversion Candidacy — quick assessment of whether your situation is a strong, moderate, or weak Roth candidate.
Retirement Age Viability — see whether your target retirement age is realistic given savings, healthcare, and income gap.
2026 IRMAA Brackets — exact dollar thresholds and what each bracket crossing costs.
Medicare Enrollment Guardian — 3-minute wizard that tells you exactly what window you're in and what to do.

See all free tools

3. Build your free personal plan

When you're ready for more than single calculators, open the free planner at app.nestpilot.org. It works right away with no account; add a free account when you want to keep your plan. No credit card. Foundation tools and accounts stay free, always — for everyone.

Open the free planner — no account needed

Save your plan
Inputs persist across sessions. Come back next month, your scenarios are still there.
Multi-decision orchestration
See how Roth conversions, IRMAA brackets, Social Security timing, and tax-efficient withdrawal sequencing interact across years.
Math is fully transparent
Every projection shows the assumptions and the math. No black-box recommendations.
Plan with family or advisor
Share your plan with your spouse, adult children, or financial advisor (read-only or collaborative).

4. Watch the full walkthrough

A complete seven-minute walkthrough of the five decisions, a sample plan with Sarah & Mark Carter (61 & 63), forecast and what-if scenarios, ACA-to-Medicare cost transitions, the resilience stress test, and the 501(c)(3) charter close.