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Benefits Insider
No panic. No politics. Just clarity.

Free online workshop

Medicare, start to finish. And we will never call you.

26 minutes. Six decisions. Taught by a finance professor who doesn’t sell insurance.

  • It’s free. Nothing is sold inside it. No upsell, no product pitch.
  • We will never call you. Not me, not an agent, not a “benefits specialist.”
  • Watch it as many times as you want. You get a permanent link.

26 minutes · Updated with 2026 numbers · Watch on any device

Instant access

Watch the free workshop

Enter your details and the workshop opens on the next screen.

I agree to receive the free Benefits Insider newsletter by email, and to join the Benefits Insider weekly text list — recurring automated marketing texts with updates that can affect your benefits, finances or retirement. Consent is not a condition of any purchase. About 1 text per week. Message and data rates may apply. Reply STOP to cancel, HELP for help. Terms · Privacy.

We will never call you. I don’t sell insurance and I don’t give your number to anyone who does.

Before you hand anything over

“So why do you need my email and phone number?”

Fair question. Here’s the straight answer.

Your email

My free newsletter

Plain-language breakdowns of Social Security, Medicare and retirement rules — what changed, and what it means for your money. Unsubscribe on any email.

Your phone

The weekly text list

One text a week with critical information and updates that can affect your benefits, your finances, or your retirement. Never a call. Reply STOP and it ends immediately.

That’s the whole trade. The workshop is free and I’m not selling anything inside it. In exchange, I’m asking for permission to stay in touch — the newsletter and the weekly text list. That’s it. We will never call you.

I’d rather tell you that up front than surprise you later. You can end either one any time, and you’ll still keep your link to the workshop.

What’s inside

Medicare isn’t a subject. It’s six decisions.

Three of them you only get to make once. Here’s all six, in the order you actually face them, with the 2026 numbers.

1

When you enroll

The 7-month window, and why nobody signs you up if you haven’t claimed Social Security yet.

You make this once

2

Whether you delay Part B

Still working at 65? The employee-count rule, the COBRA trap, and the HSA mistake.

You make this once

3

Supplement or Advantage

Who each one is actually good for — and why one direction is a one-way door.

You make this once

4

Your drug plan

The 2026 out-of-pocket cap, and why the cheapest premium is rarely the cheapest year.

5

Whether you qualify for help

Two programs most people never apply for. One can pay your Part B premium outright.

6

What your income does

The surcharge nobody names, the 2-year lookback, and the form that undoes it.

Who’s teaching this

Not an insurance agent.

I’m Kwame Kuadey. I teach finance at Johns Hopkins Carey Business School and I run Benefits Insider, where about 220,000 people follow along.

I don’t earn a commission on anything you choose. That’s why I can tell you who each option is actually good for.

  • Adjunct Professor of Finance — Johns Hopkins University Carey Business School
  • Author, The Social Security Playbook
  • Founder, Benefits Insider — Social Security, Medicare & benefits education
  • Every figure verified against CMS and SSA, and re-checked every year

Ready to watch?

26 minutes, free, nothing sold — and you keep the link for as long as you want it.

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