8 Mistakes Costing IRA Millionaires MILLIONS

In this solo presentation, CFP® Craig Wear outlines the five most costly Roth conversion mistakes made by high‑net‑worth IRA owners and explains why they each can waste hundreds of thousands of dollars in taxes. He then identifies three major barriers that prevent investors from executing optimal conversion strategies: inadequate professional software and AI prompting, reliance on static DIY spreadsheets, and advisors/CPAs lacking specialized Roth conversion expertise. Wear also highlights three portfolio‑related risks—emotional reactions, hidden fees, and underperforming managers—that can erode the benefits of any conversion plan. Throughout, he stresses the importance of leveraging experienced specialists and provides a free booklet that walks readers through the math and key questions to ask advisors, aiming to help IRA millionaires capture missed tax savings.
Chapters
So, I've listed 5, what I say are the most expensive Roth conversion mistakes that IRA millionaires make. Number 1 is the biggest mistake is only converting to the top of your current tax bracket. That is never a good idea. And you may have somebody you have a great relationship and you've trusted them with millions of dollars for 25 years telling you to do that. I totally respect that. They just are not an expert in this field. They haven't run as many numbers. They haven't had as many clients. They don't have as many reps. We've had over 2,400 clients that we've had to do the math and multiple times. So we know these to be true principles and we know how to apply those. The second biggest mistake is just stopping at some Medicare premium threshold. People are so afraid of paying IRMAA premiums that they leave millions of dollars on the table so that they don't pay an extra $500 a month of Medicare premiums. It's just insane that some of the things we— it's logical, it makes sense, you don't want to do that. But when you back out and you look at the lifetime of tax, it's easy to step over a small amount of Medicare premiums to get a big win on the taxes. The third mistake is just to pause conversions when Social Security kicks in. Some people convert, convert, convert, and all of a sudden when Social Security kicks in, they say, "Oh, well, we got to stay at that same tax bracket," and they back off. The fourth mistake is really just by default making the IRS a very significant heir to your retirement savings. There's just no reason to do that. You can avoid that and you end up the winner. If you'll take control of it. The fifth one is just overlooking the charitable giving opportunity. So, if you are a giver, if you're somebody who regularly makes and supports your local church or causes that you care about or synagogue or whatever religious or charitable organization that you're affiliated with, there are ways to wrap that into the Roth conversion game plan to really save a lot of taxes on the front end also. But each of these 5 we see cost IRA millionaires independently. Each of these are hundreds of thousands of dollars of taxes that could have been avoided. So what keeps people from making the best decision? Interestingly enough, the first one is just professional software. We evaluate every piece of software that we can find and see available. Some are built for Roth conversion analysis, some of the new stuff, but they aren't built to adapt to a variety of changes into a variety of input. And so, the person using the software needs to have a whole lot of experience to make it work. One of the things we get a lot now is somebody says, "Well, I ran." I ran my situation through one of the AI agents and I got a great answer I'm comfortable with. Fantastic. We've had our own CFP®s who deal with this day in and day out go in and issue prompts to 2 or 3 of the biggest AI agents. And the answer was still wrong. Unless you know exactly what inputs and how to prompt it and you had experience with this, you don't stand a chance of getting the optimal answer. And you may get a better answer than what your spreadsheet did, but to get really the best answer, it just takes experience. And that's not something that in today's world a machine is going to be able to do for you. It needs a human being to interpret and to make sure that the experiences that they have had match what a machine is offering to them. And most of those just regular software that's out there just does not do a great job of allowing for a variety of different strategies to compare. And then I guess the second barrier is all the DIY spreadsheets that are out there. And I don't mean it in a personal affront to you at all, But spreadsheets is what we started with. They're just very difficult to have to be interactive. You have to make static assumptions. There's really very little real stress testing that you can do. And more importantly, there's really no peer review. So, you're relying on— you're assuming that everything that you know about the subject is going to produce the best outcome. And maybe you're that unicorn. We've had maybe a half a dozen people across thousands of conversations that actually, they got it right. And we had to say to them, "Congrats. I don't know that we can help at all." But just a small variance from optimal means hundreds of thousands of dollars to you. And I just want to encourage you, sometimes it's better to get to a specialist that's been here and done this before. Most people that are doing this have not retired before, and they certainly haven't done multi-year aggressive Roth conversions before. And so, you're going to learn some stuff. We would like to let you get the benefit of our experience instead of kind of pay for your own experiences. And the other third biggest barrier, unfortunately, is just a lot of existing advisors and CPAs are just not trained to do this, um, to give proactive Roth conversion advice. They're focused on last year or maybe next year, or their lenses are very tight in what they're looking at. Sometimes they're just not even allowed to give you the advice if they're with a bigger firm. Most of the bigger firms won't allow that. We've got a great relationship with a lot of clients that are at some of the biggest firms and the biggest names that are out there, and they bring us those reports that they give them that are supposed to be Roth conversion person reports. And, you know, one example is we've got one of the big firms that's got advertisements running all over the evening TV programs. They gave them a 3, 5, and 7-year game plan that was out of one of the top professional software available in the financial planning industry, and they thought that was good. And that's better than nothing. But the money that they were leaving on the table, I mean, what if the answer was not 3, 5, or 7? What if the answer was 4, but somebody chose 7 because they didn't have the experience to know how to coach you to make sure you did the 4 instead of the 7? What if the answer included different variables than what was included because that person just knows how to plug in numbers to software, but they don't have experience in actually how this plays out in real life. And so they're not malintended, they just don't have the experience of it. It's like going to your primary care physician for open heart surgery. The guy that does the surgery isn't necessarily smarter than the primary care doctor. He just has a focus and he does it every single day. And so he knows his way around a whole lot better than the primary care doctor care doctor that in, in our world maybe does half a dozen conversion plans a year, you know. But look, all of the variables create a problem that most tools and advisors just simply aren't built to solve. Hey, you know what, even a perfect Roth conversion plan cannot fix what's broken in your portfolio. There's 3 things that cause a lot of problems. One are your emotions, how you handle it in a down market. The other one are fees that you can't see, and the other are managers who consistently underperform what is possible. I— this is so important. There's, there's like a million or more dollars that are at stake for you if you're an IRA millionaire. So I've written a free booklet that kind of goes through the math and shows you what kind of questions you can ask your advisors or yourself in determining if you're doing the right things that you need to for your portfolio during Roth conversion. So grab the link below and grab the booklet, see if it helps some. Take care.










