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Your 3-minute 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 paired with a paid Pro tier for those who want more.
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.
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.
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.
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.
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.
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.
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.
- Medicare Enrollment Guardian — 3-minute wizard that tells you exactly what window you're in and what to do.
- 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.
3. Set up a free personal plan
When you're ready for more than single calculators, create a free account at app.nestpilot.org. No credit card. The Foundation tier stays free.
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).
Paid Pro tiers (continuous monitoring, multi-scenario comparison, advisor / family sharing) are on the commercial side at www.nestpilot.net — separate from the Foundation, but the same engine.
4. Watch the intro
Prefer video? Two short overviews — one for individuals navigating retirement, one for community organizers thinking about sponsoring seats or hosting a seminar.
NestPilot Foundation — Features overview
For HOAs, employers & community organizers
More ways to engage
Communities
HOAs, employers, churches, libraries — host a free retirement-literacy seminar or sponsor seats for your members.
Community programsQuestions?
Have a specific question or want to be a guinea pig user? Reach out directly.
Email the founder