Anthony, Hindsight Is Money

Hindsight Is Money

Leveraging my hindsight to help you shorten your path to financial independence.

Free retirement planning spreadsheets, videos, and the resources I actually use — before and after retirement.

Watch on YouTube

Money lessons I learned the hard way, so you don't have to. New videos walk through each tool with real examples.

Free Retirement Tools

🔒 Free Tools are for YouTube subscribers of Hindsight Is Money.▶ Subscribe

Google Sheets templates — Coming soon. Links are paused while I finish sharing the public copies. Yellow cells will be your inputs.

Planning & Readiness

Retirement Preparedness Checklist

62-question gap analysis with Pre/Post-retirement filters and a readiness score.

Free tool provided as-is. Formulas and results aren’t guaranteed, and I’m not responsible for how you use the outcomes or your data — use at your own risk.

Make a copyOpen template →

Median Monthly Spend

Find your real median monthly spending from tracked expenses.

Free tool provided as-is. Formulas and results aren’t guaranteed, and I’m not responsible for how you use the outcomes or your data — use at your own risk.

Make a copyOpen template →

Healthcare Retirement Estimation

Estimate healthcare costs from retirement through Medicare.

Free tool provided as-is. Formulas and results aren’t guaranteed, and I’m not responsible for how you use the outcomes or your data — use at your own risk.

Make a copyOpen template →

Perspective

Weeks of Our Lives

See your life in weeks and put the time you have left in perspective.

Free tool provided as-is. Formulas and results aren’t guaranteed, and I’m not responsible for how you use the outcomes or your data — use at your own risk.

Make a copyOpen template →

AI Prompts

Boldin AI Prompts

Ready-to-use AI prompts for getting more out of Boldin planning.

Free tool provided as-is. Formulas and results aren’t guaranteed, and I’m not responsible for how you use the outcomes or your data — use at your own risk.

Make a copyOpen template →

Income, Tax & Withdrawals

Income, Tax & ACA Planner

Plan retirement income against tax brackets and ACA subsidy limits.

Free tool provided as-is. Formulas and results aren’t guaranteed, and I’m not responsible for how you use the outcomes or your data — use at your own risk.

Make a copyOpen template →

Roth Conversion Strategy

Model Roth conversions year by year and their tax impact.

Free tool provided as-is. Formulas and results aren’t guaranteed, and I’m not responsible for how you use the outcomes or your data — use at your own risk.

Make a copyOpen template →

Withdrawal Plan Timeline

Map which accounts you draw from, and when.

Free tool provided as-is. Formulas and results aren’t guaranteed, and I’m not responsible for how you use the outcomes or your data — use at your own risk.

Make a copyOpen template →

Guardrails Strategy

Set spending guardrails that adjust with your portfolio.

Free tool provided as-is. Formulas and results aren’t guaranteed, and I’m not responsible for how you use the outcomes or your data — use at your own risk.

Make a copyOpen template →

Investing Buckets

Bucket Strategy & Allocations

Set up a bucket strategy and target allocations for each bucket.

Free tool provided as-is. Formulas and results aren’t guaranteed, and I’m not responsible for how you use the outcomes or your data — use at your own risk.

Make a copyOpen template →

Spending & Healthcare

Creators & Sites I Learn From

My own "YouTube University": the channels and sites that taught me the most. More picks from my subscriptions are on the way.

Financial and Retirement Planning

Big-picture retirement shows: when you can retire, how much you can spend, and how to make it last.

Outside the Box

Unique or creative approaches to financial and retirement planning.

More coming soon

Retirement Tools Advice

How to use retirement planning software and tools so your numbers work for you.

More coming soon

Managing Debt and Building Wealth

Getting the foundation right: a budget, an emergency fund, getting rid of debt, and building wealth step by step.

More coming soon

General Financial Topics

Everyday money questions, withdrawal strategies, and honest tool reviews.

  • Rob Berger (YouTube)Answers common financial questions, weighs withdrawal strategies, and reviews planning tools.

More coming soon

Crypto Basics

Plain-English explainers so crypto concepts actually make sense.

More coming soon

Retirement Journeys

Real stories of people living retirement — the day-to-day, the emotions, and what actually worked.

  • Joe Kuhn (YouTube)Retired at 54 — fears, lessons, and the real transition from work to retirement.

Modest Portfolio Retirement

Retirement planning when the nest egg is smaller — practical strategies that still work.

ACA

Affordable Care Act planning for early retirement and health coverage before Medicare.

More coming soon

Helpful Resources

Government

Official sources for benefits, taxes and coverage. Start here before anywhere else.

Calculators

Run the numbers yourself and stress-test your plan.

Longevity / Life Expectancy

How long should your money last? Plan for a long life, not an average one.

Healthcare Cost Estimators

Healthcare is one of retirement's biggest wildcards. Estimate it across Medicare, Medicaid and private coverage.

Investing Research

Look up funds and companies before you buy.

Contact

Send me a note. Pick a topic so I can route it, and keep it under 1,000 characters.

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