Rob Moore on Roth IRA Conversion Ladders to Fund Early Retirement #229

Rob Moore on Roth IRA Conversion Ladders to Fund Early Retirement #229

May 18, 2026 · 49 min

About this episode

Spencer Reese interviews Rob Moore about Roth IRA conversion ladders and their benefits for early military retirement.

What if you could retire from the military at 50, bridge a decade of income, and pay less in taxes than you ever expected? It sounds too good to be true — but it's written right into the tax code . Spencer and Rob walk through exactly how a Roth conversion ladder works, who it's built for, and whether a simple brokerage account might actually beat it. Spencer Reese interviews Rob Moore, Army veteran, CFP candidate, and founder of Everman Wealth and Prosperity. Topics Discussed What a Roth Conversion Ladder is — moving funds from a traditional IRA to a Roth IRA each year before military retirement to create penalty-free supplemental income during the bridge period between military retirement and age 59½ Who it's for — service members retiring before 59½ who need to bridge their income gap, and those in the FIRE community with lower taxable income Contribution vs. Conversion — contributions can be withdrawn penalty/tax-free anytime; conversions require a five-year waiting period per conversion year The Five-Year Rule — each conversion starts its own five-year clock on January 1st of the conversion year; after five years, the converted amount can be withdrawn penalty and tax-free…

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