Episodi

  • Taking Risk Off the Table: Bonds, Cash & Your Investment Strategy

    Taking Risk Off the Table: Bonds, Cash & Your Investment Strategy
    Oct 15 2026
    “Well… It Depends!” explores financial questions that rarely have a one-size-fits-all answer. In this episode, hosts Andrew Baron and Derek Doyle discuss how rising bond yields, interest rates, and changing market conditions can influence investment decisions and the role of cash and fixed income in a broader financial strategy. Andrew and Derek begin by explaining the relationship between bond prices and yields, including why existing bond prices generally fall as interest rates rise. They also explore why bond yields may be increasing even as inflation cools, discussing the impact of government borrowing, growing debt issuance, and supply and demand in the […]
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    12 min
  • Am I Saving Enough? Here's How to Know

    Am I Saving Enough? Here's How to Know
    Oct 1 2026
    “Well… It Depends!” explores financial questions that rarely have a one-size-fits-all answer. In this episode, hosts Andrew Baron, CFP®, EA, and Derek Doyle discuss one of the most common questions people have as they prepare for retirement: Am I saving enough? With the end of the year approaching, the conversation looks at the different ways people can build retirement savings and how much they may need to save on their own to supplement Social Security and support the lifestyle they want in retirement. Andrew and Derek begin by reviewing the 2026 contribution limits for employer-sponsored retirement plans, including 401(k)s and similar […]
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    17 min
  • Back to School: What You Should Know About 529 Plans

    Back to School: What You Should Know About 529 Plans
    Sep 17 2026
    “Well… It Depends!” explores financial questions that rarely have a one-size-fits-all answer. In this episode, hosts Andrew Baron, CFP®, EA, and Derek Doyle discuss education savings and the different account options available to parents and grandparents looking to help cover the rising cost of education. With the back-to-school season underway, the conversation focuses on 529 plans, Coverdell ESAs, and custodial accounts such as UGMAs and UTMAs. The conversation takes a closer look at why 529 plans have become such a widely used education savings tool, including their tax advantages, expanded list of qualified education expenses, and flexibility for both college and […]
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    14 min
  • Can You Afford to Self-Insure Long-Term Care?

    Can You Afford to Self-Insure Long-Term Care?
    Sep 3 2026
    “Well… It Depends!” explores financial questions that rarely have a one-size-fits-all answer. In this episode, hosts Andrew Baron, CFP®, EA, and Derek Doyle examine one of the most overlooked risks in retirement: the potential cost of long-term care. While Medicare may cover many routine healthcare expenses, it generally does not cover the extended care provided by nursing homes, assisted living facilities, or in-home care—and those costs can add up quickly. The conversation explores the different ways retirees can prepare for long-term care expenses, including traditional long-term care insurance, hybrid life insurance policies with long-term care benefits, self-insuring, and Medicaid. Andrew and […]
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    13 min
  • AI Stocks, Market Volatility & Why Your Financial Plan Matters

    AI Stocks, Market Volatility & Why Your Financial Plan Matters
    Aug 20 2026
    “Well… It Depends!” explores financial questions that rarely have a one-size-fits-all answer. In this episode, hosts Andrew Baron, CFP®, EA, and Derek Doyle examine the market and economic forces shaping the second half of 2026. With markets near record highs, inflation remaining persistent, and interest rates potentially staying higher for longer, they explore what investors should be considering as they position their portfolios for the months ahead. The conversation covers interest rates, cash and fixed-income strategies, inflation and energy prices, geopolitical uncertainty, and the potential impact of continued AI investment. Andrew and Derek also discuss portfolio rebalancing, concentration risk, taking profits […]
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    14 min
  • 2026 Market Update: Fed, Inflation, AI Stocks & Investing Outlook

    2026 Market Update: Fed, Inflation, AI Stocks & Investing Outlook
    Aug 6 2026
    “Well… It Depends!” explores financial questions that rarely have a one-size-fits-all answer. In this episode, hosts Andrew Baron, CFP®, EA, and Derek Doyle examine the current investment landscape following a strong first half of 2026. With markets reaching new highs, inflation remaining persistent, and the Federal Reserve signaling that interest rates could stay higher for longer, investors are asking what comes next—and how they should position their portfolios for the remainder of the year. Andrew and Derek break down the latest economic developments, including the Federal Reserve’s evolving outlook for interest rates and what a “higher for longer” environment could mean […]
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    15 min
  • Trump Accounts Explained: Should You Choose One Over a 529 Plan?

    Trump Accounts Explained: Should You Choose One Over a 529 Plan?
    Jul 23 2026
    “Well… It Depends!” explores financial questions that rarely have a one-size-fits-all answer. In this episode, hosts Andrew Baron, CFP®, EA, and Derek Doyle discuss one of the newest developments in financial planning: Trump Accounts. Following the passage of recent federal legislation, these new tax-advantaged accounts are now available to help families begin saving for a child’s future, creating new opportunities—and new planning decisions. Andrew and Derek explain how Trump Accounts work, including eligibility requirements, contribution rules, investment limitations, and the government’s $1,000 seed contribution available for qualifying children born between January 1, 2025, and December 31, 2028. They discuss how […]
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    11 min
  • Equity Compensation: Are You Taking Too Much Risk?

    Equity Compensation: Are You Taking Too Much Risk?
    Jul 9 2026
    “Well… It Depends!” explores financial questions that rarely have a one-size-fits-all answer. In this episode, hosts Andrew Baron, CFP®, EA, and Derek Doyle are joined by Jason Nickerson, CFP®, EA, President and CEO of John G. Ullman & Associates, to discuss one of the most complex areas of financial planning: equity compensation. As markets reach new highs, many employees may find themselves holding a significant amount of company stock through equity compensation programs. But owning a concentrated position in the company you work for creates unique planning considerations—especially when your income, benefits, and investments may all be tied to the […]
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    21 min