Craig Wear, CFP®Craig Wear, CFP® | Expert in Roth Conversions & Tax-Efficient Retirement Strategies for IRA Millionaires

How To Beat The IRS At Roth Conversions

8 Jul 2026 · 1 min

Watch on YouTube

0:50

In this YouTube segment, CFP® Craig Wear frames Roth conversion planning as a strategic chess match against the IRS. He argues that a successful conversion isn’t a one‑off transaction but the result of a year‑long sequence of moves—positioning assets, timing conversions, and selecting investments—so that the final conversion delivers maximum tax advantage. Wear cites internal research indicating that when all pieces (full planning year, coordination, timing, and investment choice) are aligned, the strategy can generate roughly $30,000 of added value for every $1,000,000 converted to a Roth IRA.

Chapters

Hey, look, your retirement tax strategy isn't about doing one Roth conversion or not. It's more like playing a game of chess against the IRS. Because we're not just talking about a single transaction. A Roth conversion isn't something you do in an afternoon in December, click a few buttons and call it good. Just like in chess, the conversion itself may be one move, but the value comes from where all the pieces were before that move was made. And if you wait too long, the IRS will have moved their piece across the board, trap you. And if you move pieces into place in preparation, you're in a whole lot better position for checkmate. Look, our research shows that conversions executed with as full a planning year as you have, proper coordination, the right timing, strategic investment selection can add as much as $30,000 of value for every million dollars of Roth that you convert.