Should You Add a Transfer on Death Beneficiary to Your Assets? #298
Release Date: 03/24/2026
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
Retire With Ryan
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
Retire With Ryan
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
Retire With Ryan
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
Retire With Ryan
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_outlineOn 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 wishes.
You will want to hear this episode if you are interested in...
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00:00 Understanding Transfer on Death designations
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03:05 Joint tenants with rights of survivorship
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04:37 Pros and cons of TOD and POD accounts
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09:03 Challenges of TOD in estate planning
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11:24 Process for establishing TOD beneficiaries
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13:00 Does TOD avoid probate?
What Is a Transfer On Death (TOD) Designation?
A Transfer on Death designation allows you to name one or more beneficiaries who will automatically receive ownership of your accounts or property when you pass away. Unlike retirement accounts and life insurance policies—which typically require you to name beneficiaries—many investment and bank accounts, such as mutual funds, brokerage accounts, and money markets, do not automatically offer this option. That’s where TOD comes into play, bridging a critical gap in your estate planning.
Pros and Cons of Using TOD and POD Accounts
One of the main benefits of a Transfer on Death (TOD) is that it allows designated beneficiaries to inherit assets quickly and directly, often by providing just a death certificate and minimal paperwork, which means they can avoid prolonged probate proceedings. This quick turnaround not only spares beneficiaries the stress and uncertainty of waiting for a court-supervised process but also helps them sidestep probate fees and other complications. Beneficiaries can benefit from a full step-up in cost basis on inherited assets, potentially reducing capital gains taxes if they sell soon after inheriting. For individuals who want to ensure their loved ones receive specific assets efficiently—and without granting them any access or control during their lifetime—a TOD can be an appealing tool.
However, while TOD accounts streamline asset transfer, they can introduce challenges if not coordinated carefully with a broader estate plan. For example, if you wish to provide ongoing financial support rather than a lump sum, a TOD may not be suitable because the beneficiary immediately gains control of the assets. This could present issues for beneficiaries who are not financially responsible or who qualify for government aid. Additionally, TOD designations override instructions in a will, which means any inconsistencies in how beneficiaries are named or assets are divided, could cause confusion or disputes. TOD accounts are convenient, but they require thoughtful coordination with other estate planning elements to avoid unintended consequences.
Does TOD Always Avoid Probate?
While TOD almost always avoids the probate process for the specific asset, state laws can vary. Some less populous or smaller estates may not need to open probate regardless, but others require probate for everyone, as it’s a revenue-generating process.
TOD and POD beneficiary designations offer an easy, low-cost way to keep more of your assets in your family’s control, minimize delays, and potentially avoid the hassle of probate. Thoughtful planning addresses not just asset transfer, but also your heirs’ needs and the tax implications. As with any estate tool, consider your specific circumstances and consult with a professional before making changes.
Resources Mentioned
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