5 Tax Mistakes To Avoid In Your Initial Retirement Years, #323
Retire With Ryan
As you transition into retirement, tax planning might not be at the top of your to-do list—but overlooking it can lead to costly mistakes. This week, I break down the five biggest tax pitfalls new retirees face, from unexpected taxes on Social Security benefits to costly Medicare premium surcharges and missed Roth conversion opportunities. I’m also sharing a few of my favorite strategies to avoid unnecessary state taxes and manage your retirement distributions with confidence. You will want to hear this episode if you are interested in... [01:45] Without planning, your risk...
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5 Year Roth IRA Rule People Get Wrong, #322
Retire With Ryan
Roth IRAs are a powerful retirement tool, much loved for their promise of tax-free growth and withdrawals. But embedded in the rules for Roth IRAs are two little-understood 5-year rules. Misunderstanding these can trip up even savvy savers, potentially exposing your hard-earned gains to taxes and early withdrawal penalties. This week I’m giving you an expert breakdown to clarify how the rule works and bust some common misconceptions. You will want to hear this episode if you are interested in... [01:13] Tax-deferred growth and conditions for tax-free distributions [05:39] Taxes...
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4 Best Options To Pay For Long-Term Care, #321
Retire With Ryan
Long-term care coverage is an essential, yet often misunderstood, aspect of retirement planning in the United States. Although many people will require some form of long-term care as they age, most are unprepared for the high costs and limited coverage options available. On the show this week, I’m debunking common myths like the notion that Medicare will fully cover all long-term care costs and taking a deep dive into the four main ways retirees can pay for these expenses. You will want to hear this episode if you are interested in... 00:00 Understanding the options for...
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Are Bonds Still A Good Investment For Your Retirement Portfolio, #320
Retire With Ryan
On the show this week, I’m helping you understand why bond prices have been dropping, what actions investors should take, and whether bonds still have a place in a retirement portfolio. I discuss the different types of bonds and how interest rates impact bond prices. I also dig into the importance of maintaining a diversified portfolio and the role bonds can play in reducing overall volatility during retirement. You will want to hear this episode if you are interested in... [02:03] Types of Bonds and issuers [03:21] Risks of investing in junk bonds [04:39] Why have bond prices...
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Top 5 Reasons Retirees Run Out Of Money, #319
Retire With Ryan
Retirement is often imagined as the reward after decades of hard work—a time for travel, relaxation, and quality time with loved ones. But for many Americans, the anxiety of running out of money casts a long shadow over these golden years. Studies reveal that concerns about outliving savings are more prevalent than fears of dying prematurely. This week we’re discussing the five key reasons retirees run out of money and sharing practical steps you can take to secure your financial future. You will want to hear this episode if you are interested in... [02:16] Even high-income...
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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]...
info_outlineThis 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 of mind you need for your retirement planning.
You will want to hear this episode if you are interested in...
- 00:00 Bank failures and investor concerns
- 05:58 Protecting your money in banks
- 09:18 Discussing investment safeguards
- 12:08 Brokerage account safety reassurance
- 13:08 Should you consolidate your broker accounts?
Why Investors Worry
It’s natural for investors to worry about the safety of their money, especially after the events of 2023, when several banks—Silicon Valley Bank, Signature Bank, First Republic Bank, and Citizens Bank—collapsed, shaking public confidence in U.S. financial institutions. Even rumors and social media speculation about potential trouble at a major brokerage like Schwab can fuel anxiety among clients and investors.
How Banks Actually Work: Your Money Becomes the Bank’s Money
When you deposit money in a bank, you’re essentially lending money to that institution. The bank can then use those deposits to fund loans, mortgages, and other investments. This works well—until poor investments or insufficient collateral put depositor money at risk, which is exactly what happened with Silicon Valley Bank following its risky bets on long-term treasuries. If a bank collapses, customers may lose deposits above the FDIC insurance limit, which is $250,000 per account owner.
Brokerage Accounts: A Different—and Safer—Model
Brokerage firms like Charles Schwab and Fidelity operate under a different structure that provides a stronger layer of legal protection for client assets. Here’s the key distinction: The assets in your brokerage account—stocks, bonds, mutual funds—are not the brokerage firm’s property. They are held in custody, separate from company assets, and protected by a legal firewall.
If Schwab or Fidelity collapsed, only the company’s assets—like buildings and offices—would be at risk, not the assets in client brokerage accounts. Those client assets are held in separate custodial accounts and cannot be used to pay the firm’s creditors. It’s a little like using a storage facility: you lock up your investments, and nobody (including the brokerage firm) can access those contents for its own purposes.
What Happens During a Brokerage Collapse?
If a major brokerage like Schwab were to fail, the Securities Investor Protection Corporation (SIPC) would step in. SIPC protection covers up to $500,000 per customer, including up to $250,000 in cash. However, most brokerages, including Schwab and Fidelity, carry additional insurance beyond SIPC requirements.
The SIPC acts much like a disaster relief agency: it verifies customer assets, ensures funds have not been misappropriated, and arranges to transfer accounts to another brokerage within days. The customer receives uninterrupted access to all their investments and holdings at the new firm.
Your Money Is Safer Than You Think
The legal and operational structure of brokerage firms offers significant protection. Even in the unlikely event of a collapse, your investments would transfer intact to another brokerage. The only real risk would be investment market performance—not insolvency of the brokerage firm. It’s even unnecessary to split your assets between brokerages purely out of safety concerns—it might simply make your finances harder to manage.
Investor protections for brokerage accounts are robust. With legal safeguards, insurance protection, and established practices for handling firm failures, you can rest assured that your assets at firms like Schwab and Fidelity are secure—even in a worst-case scenario.
Resources Mentioned
- Retirement Readiness Review
- Subscribe to the Retire with Ryan YouTube Channel
- Download my entire book for FREE
- Securities Investor Protection Corporation (SIPC)
- Federal Deposit Insurance Corporation (FDIC)
- Fidelity
- Charles Schwab
Connect With Morrissey Wealth Management
www.MorrisseyWealthManagement.com/contact