The Flagship Course
Retire with a plan — not a prayer.
The Retirement Masterclass is the complete playbook in one place: Social Security, Medicare, taxes, annuities, housing, healthcare, retiring overseas, and making it work on a tight budget — so you don't have to spend months researching it all yourself.
Fourteen video lessons in plain English, each about 15 minutes, plus a guided 90-day program that turns what you learn into a finished plan with your own numbers in it.
Secure checkout by Stripe. Instant access in the members area.
Lessons
14 video modules
Watch time
About 3.5 hours
Extras
90-day program · calculators · worksheets
Access
Instant — members area, yours to keep
What's inside — all 14 modules
Watch them in order, or jump straight to the decision you're facing. Every module ends with the action steps to take.
Module 1
The Retirement Reality Check
The truth about retirement in America today — what people actually have saved, what happens with no plan, and why putting your plan on paper changes everything.
Module 2
Social Security: Get Every Dollar
How your benefit is calculated, what the claiming decision really costs or earns you, and the spousal, survivor, tax, and work rules most people never hear about.
Module 3
Medicare & Healthcare Costs
Every part of Medicare in plain English, the two main coverage paths, the deadlines that matter, and what healthcare will actually cost you in retirement.
Module 4
The Nest Egg: Build & Protect
The accounts, the catch-up rules after 50, an age-appropriate investment mix, and the handful of big mistakes that destroy more nest eggs than any market crash.
Module 5
The Paycheck: Making It Last
How to turn savings into a steady paycheck that lasts as long as you do — the 4% rule and its limits, smarter withdrawal approaches, and the early-retirement risk that matters most.
Module 6
Annuities & Guaranteed Income
What annuities are, the main types, and real strategies people use — plus the fees, traps, and sales pitches to watch out for, so you know when one is a smart tool and when it's an expensive mistake.
Module 7
Pay Less Tax in Retirement
Your tax bill in retirement is a choice, not a fixed number. The levers: withdrawal order, the Roth conversion sweet spot, RMD rules, and how states treat retirees differently.
Module 8
Housing: Your Biggest Lever
Housing is your largest asset and largest expense at once. The math of downsizing, renting vs. buying, America's cheapest retirement markets, and manufactured homes in plain English.
Module 9
Retiring Abroad
Where Americans go, what it really costs, what healthcare looks like overseas, visas, the tax basics every expat must know — and how to test-drive a country before you commit.
Module 10
Retiring on Less
A practical playbook for retiring with little saved — housing, smart frugal systems, part-time income, and the benefit programs that exist for exactly this situation and too often go unclaimed.
Module 11
Long-Term Care & Elder Care
The four levels of care and what each costs, why Medicare doesn't pay for this, long-term care insurance basics, and how to have the family conversation before a crisis forces it.
Module 12
Estate & Legacy
Wills, trusts, beneficiaries, power of attorney, and healthcare directives in plain English — the paperwork that speaks for you when you can't, with a complete documents checklist.
Module 13
The Happy Retirement
What your days actually feel like once the paycheck stops — purpose, health habits, the loneliness risk nobody warns you about, and designing a week you love.
Module 14
Your 90-Day Action Plan
The capstone: everything turned into a personal plan — a week-by-week schedule for your first 90 days, a master checklist, and your whole plan summarized on a single page.
More than videos — the working tools are included
The Guided 90-Day Program
Six two-week blocks that walk you through the whole plan — what to learn, what to do, and in what order — so the course becomes a finished plan, not just information.
4 Retirement Calculators
Social Security claiming (62 vs. full retirement age vs. 70), safe withdrawals, long-term care costs, and required minimum distributions — run your own numbers.
Printable Forms & Worksheets
The Retirement One-Pager, the 90-Day Action Plan Checklist, the Master Action Checklist, the Estate Documents Inventory, and the Annual Review Template — print-ready PDFs.
Plain English, Start to Finish
No jargon, no sales pitches, no talking down. Every module is about 15 minutes and ends with the exact action steps to take.
Who this is for
You're within about 10 years of retiring and want every decision — claiming, coverage, taxes, housing — made on purpose, in the right order.
You're already retired and want to check the plan you have: Are you overpaying tax? Claiming the right way? Covered if care is ever needed?
You don't have much saved and need the honest playbook — Module 10 is written for you, and the housing and abroad modules may change your math entirely.
Your retirement, planned in 90 days
One payment of $97. All 14 modules, the guided 90-day program, the calculators, and every printable worksheet — in the members area, yours to keep and revisit every year.
Secure checkout by Stripe. Your access opens the moment your payment clears.
Educational content only — not financial, legal, tax, or investment advice. The Prosper Academy teaches how retirement decisions work; your situation is your own, and nothing here guarantees outcomes.
Retirement Masterclass
14 modules · 90-day program · calculators & worksheets