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Retire With Ryan

Retire With Ryan

By: Ryan R Morrissey
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If you're 55 and older and thinking about retirement, then this is the only retirement podcast you need. From tax planning to managing your investment portfolio, we cover the issues you should be thinking about as you develop your financial plan for retirement. Your host, Ryan Morrissey, is a Fee-Only CERTIFIED FINANCIAL PLANNER TM who lives and breathes retirement planning. He'll be bringing you stories and real life examples of how to set yourself up for a successful retirement.2020 Retirewithryan.com. All Rights Reserved Economics Personal Finance
Episodes
  • Do Actively Managed Funds Perform Better Than Index Funds In Volatile Markets? #312

    Do Actively Managed Funds Perform Better Than Index Funds In Volatile Markets? #312
    Jun 30 2026
    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... [00:00] Understanding index funds and actively managed funds[05:55] Stock picking and bond strategies[07:21] Comparing index funds to active funds[11:44] 2025 market performance and instability[13:43] Low probability of selecting an outperforming active fund[15:42] Investing in index funds Understanding Index Funds and Active Management The conversation focused on clarifying the definitions and roles of both index funds and actively managed funds in a portfolio. Index funds are mutual funds or exchange-traded funds (ETFs) specifically designed to track an index, such as the S&P 500, which comprises the 500 largest companies in the U.S. However, indexes extend well beyond large-cap U.S. companies to include mid-size, small-cap, international, emerging markets, real estate, and various bond markets. Actively managed funds, in contrast, are overseen by managers aiming to outperform their index benchmarks by selectively choosing investments they believe will generate higher returns. Several points were raised, including that these managers may focus on only a subset of the companies in an index, relying on research, forecasts, and periodic rebalancing in an attempt to add value. The Cost Factor: Why Fees Matter Management expenses are an ongoing drag on returns. Index funds typically charge extremely low fees, often around 0.1% annually, because they passively track an index and involve little decision-making. In contrast, actively managed funds average around 1% or more per year, reflecting the higher costs of professional research, trading, and active oversight. This fee gap means that even if an active manager chooses well, they must first clear a substantial hurdle just to keep pace with an index fund. What the Data Shows About Performance in Volatile Markets In the volatile year of 2025, only 38% of actively managed funds outperformed their passive benchmarks in the U.S. stock market. For large-cap stocks like those in the S&P 500, the number was even lower—just 30%. International stock managers fared slightly better, with a 48% success rate, and emerging market funds did the best, at 64%. However, over longer periods, the active management advantage all but disappears. Over 10 years, only 8.1% of large-cap blend active managers beat their benchmarks, with small-cap and international funds performing marginally better, and bond managers seeing a 41% success rate. But for 20-year periods, even those slim advantages deteriorated further. Should Index Funds Still Be the Core of a Retirement Portfolio? The data strongly supports favoring index funds for most of a retirement portfolio, especially for stock allocations. Index funds keep costs low, are simple to implement, and historically have delivered better risk-adjusted returns for the vast majority of investors across long time horizons. While some areas, such as certain bond categories or emerging markets, may occasionally offer pockets of relative opportunity for active managers, these successes are rare, short-lived, and hard to identify in advance. For most retirees, sticking primarily with index funds and maintaining a diversified, long-term approach remains the prudent and statistically advantageous strategy, regardless of temporary episodes of market turmoil. Resources Mentioned Retirement Readiness ReviewSubscribe to the Retire with Ryan YouTube ChannelDownload my entire book for FREE Morningstar's Active/Passive Barometer Report Connect With Morrissey Wealth Management www.MorrisseyWealthManagement.com/contact Subscribe to Retire With Ryan
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    17 mins
  • Is Your Money Safe With Schwab or Fidelity? #311

    Is Your Money Safe With Schwab or Fidelity? #311
    Jun 23 2026
    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 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 concerns05:58 Protecting your money in banks09:18 Discussing investment safeguards12:08 Brokerage account safety reassurance13:08 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 ReviewSubscribe to the Retire with Ryan YouTube ChannelDownload my entire book for FREE Securities Investor Protection Corporation (SIPC)Federal Deposit Insurance Corporation (FDIC)FidelityCharles Schwab Connect With Morrissey Wealth Management www.MorrisseyWealthManagement.com/contact Subscribe to Retire With Ryan
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    14 mins
  • How To Make Your Brokerage Account Work Like A Roth IRA, #310

    How To Make Your Brokerage Account Work Like A Roth IRA, #310
    Jun 16 2026

    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 will want to hear this episode if you are interested in...
    • 00:00 Overlooked benefits of after-tax brokerage accounts
    • 02:29 Limitations of the Roth IRA
    • 06:20 Tax implications of brokerage accounts
    • 07:57 Tax benefits of growth stocks
    • 13:14 Understanding Tax Brackets and Deductions
    • 16:53 Inheritance rules for IRAs vs. brokerage accounts
    • 17:44 Managing taxable brokerage accounts



    Understanding Taxable Brokerage Accounts

    A taxable brokerage account lets you invest in virtually anything: stocks, mutual funds, bonds, ETFs, and more. These accounts, however, are often dismissed when compared to their tax-advantaged counterparts because:

    • Annual Taxation: Every year, you pay tax on dividends, interest, and any realized gains.

    • Ordinary Income Tax on Short-Term Gains and Interest: Holdings sold within one year and earned interest are taxed at your regular income rate.

    • Potential for Long-Term Capital Gains Tax: Sales after more than one year are taxed at the long-term capital gains rate, which is typically lower.

    When used strategically, they offer flexibility and powerful tax advantages.

    Making Your Brokerage Account Behave Like a Roth

    The key to unlocking Roth-like benefits is understanding how and when taxes apply—and how to minimize them. Invest strategically and focus on growth over dividends. Choose investments that don't pay dividends, such as growth stocks or low-dividend index funds. No dividends mean no annual income to be taxed because gains are only taxed when you sell.

    You can also use Index Funds and ETFs, which usually distribute minimal dividends and capital gains, keeping annual taxes low. Avoid open-end mutual funds in taxable accounts, as they tend to generate capital gains every year, eroding long-term growth with recurring taxes.

    Realizing 0% Capital Gains

    If your total taxable income (after deductions) stays within the 12% tax bracket—a figure that for 2026 is $50,400 for singles and $108,800 for married couples file jointly—you can sell appreciated assets and owe 0% in federal capital gains tax. It's wise to time withdrawals, plan major sales during years with little other income—such as early retirement or a gap year—to fall within the 0% bracket. Keep an eye on your other sources of income: IRA withdrawals, Social Security, and pensions count toward taxable income, potentially bumping gains into the taxable range.

    Estate Planning Advantages

    Taxable accounts also offer:

    • Ability to Borrow: Take loans against your investments without triggering taxable events
    • Step-Up in Cost Basis: Heirs inherit assets at their market value on your death, often eliminating capital gains on past appreciation—a feature that Roths don't fully replicate.

    By understanding how to structure and manage your taxable brokerage account, you can access strategic flexibility—not just in managing withdrawals, but in transferring wealth to future generations. The "secret" is simply knowing and applying the rules, with tax-aware investing and withdrawal strategies smoothing the way for potentially tax-free wealth growth and transfer.



    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



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    20 mins
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