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

Fix Your IRA Investments BEFORE You Roth Convert

22 Jun 2026 · 1 min

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1:05

In this presentation, Craig Wear, CFP®, explains that many IRA millionaires see a substantial discrepancy between the balance shown on their IRA statements and the amount their families actually retain. The gap, often amounting to hundreds of thousands or even millions of dollars, is caused by sub‑optimal investment decisions within the IRA—selling during market downturns, holding cash for too long, chasing underperforming funds, and paying fees. Even a modest annual shortfall of one or two percent compounds over decades, turning a $1 million IRA into something that could have been close to $2 million. Wear uses a case study of “Tom,” a competent self‑directed investor whose IRA suffered quiet erosion before he considered a Roth conversion. The core message is that investors must address these inefficiencies and clean up their IRA portfolios before converting any dollars to a Roth IRA, ensuring the family keeps the maximum possible wealth.

Chapters

I want you to see something. This is what your IRA statement says your family has. And this is what your family actually keeps. And for most IRA millionaires, the gap can mean hundreds of thousands of dollars, could be millions of dollars that end up with the IRS instead of with their family. It's really about how you're investing inside your IRA before you ever convert a single dollar. Tom had been managing his own portfolio for 30 years and he was actually pretty good at it. I mean, better than most, but like almost every self-directed investor, there was a gap between what the market returned and what Tom actually captured. Same way with professional managers. And even a small gap, just a percentage or two a year, doesn't stay small. It compounds and over decades quietly turned into one of the biggest drags on your portfolio. So Tom's IRA is sitting at $1 million, but it probably should be closer to $2 million. And that gap doesn't really stop growing. The balance Tom is converting from, it was $1 million after decades of quiet erosion, selling during a downturn, sitting in cash, maybe a little too long, chasing a fund that wasn't really what it looked like. And then on top On top of that, you got fees.