Retire With Ryan
On this episode, I’m digging into the ins and outs of in-plan Roth conversions. You'll learn what it means to convert pre-tax 401(k) dollars to a Roth 401(k), who is eligible, and why it might make sense for your retirement strategy. I cover the practical steps for making these conversions, and highlight the benefits and drawbacks. I also share a real-life example of how a client navigated her options to maximize her retirement savings. You will want to hear this episode if you are interested in... [00:00] In-plan Roth conversions [01:51] What is an in-plan Roth conversion? [02:38]...
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For many Americans, the idea of aging in place, or remaining in your own home as you grow older, represents comfort, independence, and familiarity. Most people understand the emotional benefits of remaining in a familiar environment, but often overlook the financial challenges, from home modifications and repairs to healthcare and in-home support, that could threaten their retirement savings. On the show this week, I break down the five key areas where your budget could take a hit and offer strategies to help you plan ahead, evaluate your options, and secure your ideal retirement lifestyle. If...
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For many Americans approaching retirement, financial planning means more than just maximizing savings and deciding when to claim Social Security. If you’re not yet eligible for Medicare and rely on health coverage through the Affordable Care Act (ACA), your Social Security claiming decision at age 62 could have a dramatic effect on your insurance costs. On the show this week, I explore the nuances of how your income, and especially the timing of your Social Security benefits, can impact your eligibility for ACA premium tax credits—and what you can do to avoid costly surprises. You will...
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As April 15 approaches, marking the end of the 2025 tax filing season, many filers are facing an unpleasant surprise: tax penalties are rising, especially for those who miss timely payments or underestimate their quarterly taxes. In this episode, I’m taking you through the reasons behind the recent surge in tax penalties and highlighting how retirees, the self-employed, and investors are increasingly affected. I'll also break down the key rules, safe harbor provisions, and practical steps you can take to avoid underpayment penalties. You will want to hear this episode if you are...
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On this milestone 300th episode of the Retire with Ryan podcast, I dig into whether the Social Security lump sum payment option is right for you. After a client reached out with questions about whether accepting a lump sum is a good deal, I want to break down how the option works, who it’s available to, and the key factors to consider when making this important decision. If you’re approaching retirement, this episode offers practical guidance on weighing the lump sum versus higher monthly benefits, health considerations, and the impact on survivor benefits and taxes. You will...
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The Iran War, which began on February 28, 2026, is impacting global markets and I’m pretty sure it’s having an effect on your portfolio too. Over the past month, the S&P 500 has dropped about 6%, largely due to surging oil prices. With crude oil climbing as high as $100 a barrel and lingering uncertainty around the conflict's resolution, volatility is weighing heavily on retirement investments. We'll explore the implications for investors, discuss historical parallels with previous market shocks, and offer practical tips to navigate the fallout—whether you're looking to...
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On the show this week, I’m talking all about the topic of probate and how adding a Transfer on Death (TOD) or Payable on Death (POD) beneficiary designation to certain assets can help you avoid your estate being tied up in the probate process. You’ll learn which types of accounts allow for TOD or POD beneficiaries, why these designations might be preferable to joint tenancy, and the pros and cons of setting them up. I break down step-ups in cost basis, the impact on estate taxes, and touch on differences across states—plus considerations to make sure your estate plan actually fits your...
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In the last episode, I discussed seven mistakes to avoid when filing your 2025 taxes. So in this episode, I'm going to discuss the tax-filing mistakes people can make when filing an extension. Here are the four most common extension errors that could cost you money, including misconceptions about payment deadlines, underestimating taxes, and the importance of understanding state-specific extension rules. You will want to hear this episode if you are interested in... [00:00] Mistakes that people can make if they're filing an extension [01:41] Importance of filing for an extension by...
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Tax season is here, and if you’re just now gathering your documents to file your return—or preparing them for your CPA—this is the time to slow down and make sure you’re not making costly mistakes. In this episode, I walk through seven tax mistakes I frequently see both tax preparers and self-filers make when filing their returns. Some of these errors seem simple on the surface, but they can lead to penalties, missed deductions, delayed refunds, or paying more taxes than necessary. My goal in this episode is to help you avoid these pitfalls so you can file confidently and keep more of...
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If you watched President Trump’s recent State of the Union address, you probably heard about the new Trump accounts, also known as 530A accounts. In this episode, I break down how these tax-advantaged investment accounts are designed to work, who qualifies, and—just as importantly, what we still don’t know. There’s been a lot of excitement, especially around the $1,000 seed money for eligible children. But before you rush to open one, there are several unanswered questions that deserve your attention. What Are Trump Accounts—and Who Qualifies? Trump accounts were introduced...
info_outlineIf you watched President Trump’s recent State of the Union address, you probably heard about the new Trump accounts, also known as 530A accounts. In this episode, I break down how these tax-advantaged investment accounts are designed to work, who qualifies, and—just as importantly, what we still don’t know. There’s been a lot of excitement, especially around the $1,000 seed money for eligible children. But before you rush to open one, there are several unanswered questions that deserve your attention.
What Are Trump Accounts—and Who Qualifies?
Trump accounts were introduced under the 2025 “Big Beautiful Bill Act” and are designed to help U.S. children build long-term wealth. Parents, grandparents, and others can contribute up to $5,000 per year per child until age 18. To jumpstart participation, children born between January 1, 2025, and December 31, 2028, are eligible for a $1,000 federal seed contribution.
Unlike a Roth IRA, these accounts do not require earned income to contribute. That’s a major difference. Most children can’t fund retirement accounts because they don’t have income. These accounts are meant to give them a head start from birth.
To qualify, a child must be a U.S. citizen, have a valid Social Security number, and be under age 18. Parents can apply either by filing IRS Form 4547 with their 2025 tax return or by visiting trumpaccounts.gov.
You’ll Want to Hear This Episode If You’re Interested In…
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[01:00] How the $5,000 annual contribution limit works
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[01:45] Why these accounts don’t require earned income
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[02:35] How to open an account through your tax return or online
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[03:00] The upcoming authentication process in May 2026
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[03:40] Whether you can invest in individual stocks like Nvidia or Tesla
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[04:30] Why Treasury guidance suggests broad index funds instead
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[05:10] Whether billions in seed money could move the stock market
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[06:00] Which financial institutions may (or may not) offer these accounts
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[07:45] Potential gift tax filing requirements for contributions
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[08:45] How withdrawals at age 18 might be taxed
The Investment Confusion and Market Impact
One of the biggest points of confusion right now is how the funds will actually be invested. The Trump accounts website shows mockups featuring individual stocks like Nvidia, Caterpillar, Home Depot, and Tesla. That certainly grabs attention. But Treasury guidance suggests investments may be limited to broad U.S. equity index funds or mutual funds, not individual stocks.
If that holds true, I actually think that may benefit most investors. Broad-based index funds have historically outperformed many individual stock pickers over time. But it’s important to understand what you’re signing up for before you contribute.
Another question I address is whether these accounts could meaningfully impact the stock market. With over 3 million sign-ups already, the initial $1,000 seed funding could total more than $3 billion. Add in private contributions and potential employer matches, and that number could grow to $7–8 billion invested when markets reopen after July 4.
That sounds significant, but compared to total daily trading volume, it’s less than 2%. It may provide a small positive impact, but it’s unlikely to cause a dramatic market surge.
Taxes, Custodians, and the Big Unknown at Age 18
There are still major tax questions. Because contributions are considered gifts and the child doesn’t have immediate access to the funds, this could create gift tax reporting complications. Even if contributions fall under the $19,000 annual exclusion (for 2026), a gift tax return may still be required due to the lack of “present interest.”
Then there’s the big question: how will withdrawals be taxed at age 18? There’s no upfront deduction for contributions, which means this isn’t structured like a traditional IRA. But it’s also not clearly a Roth. My expectation is that only the gains will be taxed, but we don’t yet know whether that will be ordinary income or capital gains.
Until we get final guidance, I strongly believe record-keeping will be critical. Track contributions carefully. If custodians change or records are lost, your child could face unnecessary tax complications later.
For now, here’s what we do know: if your child, or a grandchild, niece, or nephew, qualifies for the $1,000 seed money, make sure the account gets opened. Even with unanswered questions, that initial funding is meaningful.
Resources Mentioned
- TrumpAccounts.gov
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Retirement Readiness on Demand Discount Code: RETIRE99
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