What Order Should I Start Withdrawing From My Investment Accounts In Retirement, #318
Retire With Ryan
When you’re moving into retirement, you’re most likely to be starting to ask yourself which investment accounts you should start drawing from first. There’s really no universal answer—retirement withdrawal strategies are deeply personal and situation-dependent. But understanding the implications of each account type and the factors that influence withdrawal order can have a massive impact on your tax burden and the longevity of your assets. You will want to hear this episode if you are interested in... [00:00] Retirement withdrawal strategy options [06:37] Roth IRA and...
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3 Ways To Make The Most of Your Restricted Stock Units, #317
Retire With Ryan
On the show this week, I answer a listener question about restricted stock units, or RSUs—what they are, how they're taxed, and the best strategies for managing them as they vest. I'll take an in-depth look at different types of vesting schedules, tax implications, and the practical choices you have when your RSUs become available. This episode is all about giving you clear guidance to help you make informed decisions about RSUs and making sure your retirement strategy is on the right financial track. You will want to hear this episode if you are interested in... 00:00 Explanation of...
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Accessing Your 401k Early With The Rule of 55, #316
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For many Americans, the idea of retiring before age 59 and a half often seems out of reach, particularly when the bulk of their savings sits in an employer-sponsored 401(k) or 403(b) plan. Traditionally, the tax code penalizes early withdrawals from these accounts. However, the Rule of 55 could open the door to a more flexible, penalty-free early retirement. On this episode, I’ll share more about this IRS provision, who qualifies, how to use it wisely, and potential hazards to avoid. You will want to hear this episode if you are interested in... [00:00] Overview of the Rule of 55 and...
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How To Avoid Taxes On The Sale Of Your Primary Residence, #315
Retire With Ryan
For many retirees, their home isn't just a place of comfort, it’s one of the largest assets on their balance sheet. However, beyond the emotional value and the years of accumulated equity, there's an often-overlooked reality: selling your primary residence can bring an unexpected tax bill. If you’re contemplating a sale or want to ensure you’re planning wisely, understanding the IRS’s primary residence capital gains exclusion is essential. On the show this week, I break down what this exclusion means, who qualifies, how to maximize its benefits, and the critical planning steps to avoid...
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Give Your Child or Grandchild A Head Start On Retirement With a Trump Account, #314
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On July 4, 2026, a groundbreaking opportunity opened for parents and guardians aiming to give their children a head start on their financial journey: Trump Accounts. Created as part of the OBBA Tax Act (“One Big Beautiful Bill” Tax Act) of 2025, these tax-advantaged investment vehicles provide a unique way to grow wealth for minors. In this episode, I break down what Trump Accounts are, who’s eligible for generous bonuses, how to get started, and how they compare to other common savings options like 529 plans. You will want to hear this episode if you are interested in... [00:00]...
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Avoid These 7 Scenarios to Keep Your Medicare Premiums Lower In Retirement, #313
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Medicare brings peace of mind to millions of retirees, but for those with higher incomes, there’s an added layer of complexity called IRMAA—the Income Related Monthly Adjustment Amount. If your modified adjusted gross income (MAGI) crosses certain thresholds, you may end up paying substantially more for your Medicare Part B and Part D coverage. In this article, we break down how IRMAA works, outline common scenarios that may unexpectedly raise your premiums, and offer actionable strategies to help you avoid unnecessary costs during your retirement years. You will want to hear this...
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Do Actively Managed Funds Perform Better Than Index Funds In Volatile Markets? #312
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When it comes to planning for retirement, one of the most commonly faced decisions is how to invest for long-term growth and stability. In turbulent times, market volatility often generates renewed debate on whether index funds, or their actively managed counterparts, offer the better path for accumulating wealth. On this episode of the show, I’m unpacking what index funds are, how they stack up against actively managed funds, and what the latest data reveals about performance during both quiet and volatile markets. You will want to hear this episode if you are interested in... ...
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Is Your Money Safe With Schwab or Fidelity? #311
Retire With Ryan
This week, I’m tackling a question that’s on the minds of many investors: How safe is your money with major brokerage firms like Fidelity and Charles Schwab? In light of recent high-profile bank collapses and widespread concerns about financial security, I discuss how banks and brokerage firms operate differently, what protections exist for your investments, and what would happen if a major brokerage firm were to collapse. Whether you’re considering how best to safeguard your assets or wondering about the real risks of brokerage failures, this episode will provide the clarity and peace...
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How To Make Your Brokerage Account Work Like A Roth IRA, #310
Retire With Ryan
When it comes to planning for retirement, Roth IRAs have gained widespread attention for their tax-advantaged status and the promise of tax-free withdrawals in retirement. Financial experts, YouTubers, and podcasters have been touting the benefits of contributing to or converting assets into Roth accounts for years. But an often-overlooked vehicle could empower you to manage your investments just as efficiently: the humble taxable brokerage account. Surprisingly, with the right strategy, you can even pay 0% capital gains tax, mirroring one of the biggest appeals of a Roth. You...
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5 Reasons To Not Invest Your Retirement Savings In Variable Annuities, #309
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Variable annuities are often promoted as a secure way to generate guaranteed income during retirement, drawing the attention of retirees seeking stability for their nest eggs. But beneath the surface, these products frequently come with complications and costs that can erode your savings and limit your financial flexibility. In this episode, I share the details of the often-overlooked downsides of variable annuities and give you some important insights every investor should consider. You will want to hear this episode if you are interested in... [03:14] What is a Variable Annuity?...
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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