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
Retire With Ryan
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_outlineHave you ever fallen victim to a RAT attack? No, not the furry kind, a Remote Access Trojan attack.
I’m discussing how cybercriminals use social engineering to target victims, and the real-world impact these threats can have on your investment accounts and personal information. I reveal the latest tactics scammers use, and, most importantly, offer practical tips to help you recognize warning signs, safeguard your accounts, and minimize your risk, whether you’re an individual managing your retirement nest egg or a business owner overseeing company assets.
You will want to hear this episode if you are interested in...
- [00:00] What is a RAT attack?
- [02:45] Avoid clicking unknown links.
- [06:28] Preventing fraud through active monitoring.
- [09:44] Enhancing network security strategies.
- [10:48] Tips for staying secure online.
The Escalating Threat of RAT Attacks
There are an estimated 2,200 cyberattacks every day, or one every 39 seconds. Global financial damages from cybercrime are projected to rise from $9.5 trillion (2024) to an estimated $10.5 trillion in 2025. It’s no longer a matter of if, but when, the next attack will happen.
How a RAT Attack Unfolds
Most RAT attacks begin with “social engineering”, that is, psychological manipulation designed to get you to act against your best interest. This can look like an email or text from what appears to be a trusted company (think Schwab, Amazon, or EZ Pass), urging you to click a link or download an attachment.
Do not click these links or download unknown files, even if the message creates a sense of urgency or familiarity. Even a simple PDF can be the Trojan horse that installs malware without you noticing.
Once delivered, the RAT malware quietly installs itself, evading your detection. It can come bundled with software downloads, or even through “drive-by” downloads, just visiting a compromised website can infect your device without any clicking at all.
More Than Just a Headache
Recently, cybercriminals hacked a client’s phone and attempted to transfer money from their investment account. Because my team actively monitors accounts and receives real-time alerts from Schwab, we caught the fraudulent activity before funds were lost. But not everyone is so lucky, if hackers compromise your credentials and accounts aren’t closely watched, money could be transferred out, leaving you to face a lengthy investigation to recover your hard-earned savings.
Simple Habits for Preventing Attacks
Most successful attacks don’t involve sophisticated hacking, they leverage human error. Train yourself (and if you’re a business owner, your staff) to recognize phishing emails and suspicious texts. Verify unexpected requests directly with the company, never through the provided links.
Lock Down Access
Implement “least privilege” access, using strong, unique passwords and two-factor authentication for every account. For investment platforms and email, enable notifications for any account activity, so you’re alerted instantly to suspicious changes.
Secure remote connections with a Virtual Private Network (VPN) and avoid unsecured public Wi-Fi. If you must work remotely, use your cell phone’s secure hotspot rather than free Wi-Fi at a coffee shop. And never log on to bank or brokerage accounts on shared or public networks.
Monitor and Layer Security
Constant vigilance is your shield. Regularly monitor account activity and set up a system of alerts. Layer your security by combining access controls, firewalls, and regular updates. Always verify new contacts or software installations, adopt a “zero trust” mindset: trust, but always verify.
Stay One Step Ahead
No single solution can prevent all RAT attacks, but a combination of awareness, good digital habits, and layered security makes a world of difference. Being informed is your best defense. Activate two-factor authentication, review your notifications and account alerts, and approach every digital interaction with a healthy dose of skepticism.
Resources Mentioned
- Retirement Readiness Review
- Subscribe to the Retire with Ryan YouTube Channel
- Download my entire book for FREE
Connect With Morrissey Wealth Management
www.MorrisseyWealthManagement.com/contact