New from Kwame Kuadey · August 19, 2026

The Social Security Playbook


7 Big Decisions and 75 Essential Answers to get every dollar you deserve — a decision-first guide from a Johns Hopkins finance professor. No panic. No politics. Just clarity.

Social Security Playbook Cover Image

350,000+

followers across YouTube, Facebook & TikTok

15+ years

helping Americans claim their benefits

Johns Hopkins

Adjunct Professor of Finance

Shark Tank

alum & 4x Inc. 5000 entrepreneur

What’s inside

Social Security isn’t a form you fill out.
It’s 7 decisions you make.

Most guides bury you in regulations. This one is organized around the decisions you’ll actually face — each with a Quick Answer, plain-English explanation, if/then scenarios, and exactly what to do next.

1

When to Claim

62, full retirement age, or 70 — the break-even math and the questions that decide it.

2

Working While on Benefits

The earnings test, what counts as income, and how withheld checks come back.

3

Spousal & Ex-Spousal Benefits

The 50% rule, the 10-year divorce rule, and how couples time their filings.

4

Survivor Strategies

How survivor benefits work and the switch strategy most people never hear about.

5

Disability vs. Early Retirement

Why filing SSDI first can protect your full benefit — and how the two interact.

6

Taxes & Withholding

Provisional income, the 0/50/85% thresholds, and keeping more of your check.

7

Medicare Timing & Social Security

Enrollment windows, late penalties, IRMAA — and coordinating all your start dates.

Included with the book

Every question has a companion video.

All 75 answers are also short, clear videos — organized by decision so you can jump straight to yours. Free for every reader.

Benefits Insider with Kwame Kuadey

About the author

Kwame Kuadey

Kwame Kuadey is an Adjunct Professor of Finance at Johns Hopkins Carey Business School, a Shark Tank alum who landed a deal on the show, and the creator of The Benefits Insider™ — a retirement-focused media brand with more than 350,000 followers. He built his first company to more than $60 million in revenue, earning a spot on the Inc. 500 and four appearances on the Inc. 5000. For over 15 years he has helped Americans navigate Social Security, Medicare, and retirement benefits with clarity and confidence.

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Read the first chapter

Get Decision 1 — When to Claim — free by email, plus this year’s key Social Security numbers.