The MedTech Wealth Advisor Podcast

The MedTech Wealth Advisor Podcast


Should You Convert to a Roth Before Retirement?

September 18, 2025

Roth conversions can be a powerful tax strategy, but are they the right move when you’re just about to retire? In this video, Matt walks through a real-life case study to test that very question. Using Jerry and Ruth Crawford’s $7.3 million portfolio, he explores different strategies, from converting everything at once to filling tax brackets little by little.

Here’s some of what we discuss in this episode:

Full Roth conversion vs. phased approach

Why converting all at once can reduce portfolio growth

Lifetime tax savings with bracket targeting

Impact of delaying Social Security to age 70

Flexibility and legacy benefits from tax-free Roth assets

0:00 – Intro

0:47 – Case Study

2:47 – Full Roth conversion

3:44 – Partial conversion

7:26 – Delaying Social Security

8:45 – Flexibility and legacy benefits

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