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10.13.26 Ask An Advisor With Wes Moss

The Clark Howard Podcast

32m
Transcript

Original podcast

Summary

Written by a model from the transcript; not yet reviewed.

This episode features Krista DeBias and Wes Moss answering listener questions about retirement, investments, and financial strategies. The discussion covers a misleading financial headline about stock yields, early retirement feasibility for low-spending households, treasury inflation-protected securities, and pension lump-sum versus annuity decisions. The hosts also explore updated strategies for health savings accounts, tax-loss lot selection, fixed indexed annuities, and carrying term life insurance into retirement.

  • Bond yields from government treasuries around five percent are distinct from risky, ultra-high stock dividend yields. 3:47
  • Low annual expenses combined with a paid-off home can make early retirement viable even at age fifty-six. 9:59
  • Treasury inflation-protected securities perform similarly to regular bonds over time, making them optional rather than mandatory. 10:41
  • Stacking health savings account contributions and investing them for long-term growth provides a triple tax-free vehicle. 21:17
  • Highest cost first out or minimum tax methods help minimize capital gains taxes when selling shares in a taxable account. 26:03

Chapters

  1. 0:00
    Podcast Intro and Sponsorship

    The episode opens with a brief introduction and sponsorship announcements from Indeed and Visible.

  2. 1:18
    Wes Moss Headlines Explained

    Wes Moss discusses a headline involving Jim Cramer and clarifies his stance on high yields and retirement income.

  3. 3:26
    Yield Ladder and Investment Strategy

    Wes explains the concept of the yield ladder, differentiating between stock dividends, bond yields, and the safe range for retirement income.

  4. 6:30
    Early Retirement Feasibility Question

    A listener asks about retiring at 56 with significant savings and low expenses; Wes provides a detailed analysis and encouragement.

  5. 10:22
    TIPS vs. Treasury Bonds for Retirees

    An anonymous question about the proportion of TIPS in a retirement portfolio is answered, highlighting their similar performance to regular bonds.

  6. 12:45
    Pension Rollover vs. Annuity Decision

    A listener weighs rolling over a pension versus taking a monthly annuity; Wes applies his 6% rule and personal preference to advise.

  7. 20:17
    HSAs: Long-Term Strategy Update

    Wes updates his view on Health Savings Accounts, advocating for long-term investment and strategic use of receipts.

  8. 25:43
    Tax-Loss Harvesting and Sale Strategies

    A listener asks about FIFO, HIFO, and other sale methods; Wes explains the benefits of HIFO and minimum-tax options.

Highlights

  • 1:53

    Clarifying Misleading Yield Headlinesinsight

    The guest clarifies a confusing financial media headline contrasting Jim Cramer and himself regarding high yields. He explains that while high stock yields above five percent can signal company distress, earning five percent on government bonds is safe and normal.

  • 7:41

    Early Retirement Feasibility Mathdata

    A listener at age fifty-four with low annual expenses of twenty-five thousand dollars wonders if he can retire at fifty-six. The guest calculates that his net worth and savings easily support this early exit.

  • 10:41

    Evaluating TIPS Performanceinsight

    The guest explains that treasury inflation-protected securities trade lower initial yields for inflation protection, yielding similar total returns to regular bond market indexes over multi-year horizons.

  • 14:22

    Pension Annuity Versus Rolloverstrategy

    A listener weighs taking a monthly pension annuity against a lump-sum rollover. The guest notes that while the payout passes the six percent return test, a rollover still provides more long-term flexibility.

  • 21:17

    Updating HSA Investment Strategyinsight

    The guest shares his updated perspective on health savings accounts, advocating for paying current medical out-of-pocket expenses while investing the HSA balance to compound tax-free for the long term.

  • 26:06

    Using HIFO for Tax Savingsstrategy

    The guest explains how highest cost first out and minimum tax methods allow investors to target specific tax lots to reduce capital gains tax bills when selling assets.

  • 29:06

    Warning Against Fixed Indexed Annuitiesinsight

    The guest strongly warns a listener against purchasing a fixed indexed annuity, explaining that their fee structures, surrender periods, and formulas do not actually invest your money directly in the S&P 500.

  • 31:43

    Term Life Insurance in Retirementinsight

    Addressing whether to keep life insurance after retiring to protect against lost social security income, the guest notes that while new policies are expensive, keeping existing term coverage is fine.

Quotes

  • “If you can afford to pay your current medical bills as you go along, year after year, then there is great power in taking your HSA money and putting it in the HSA account, investing it for the long run.”
    Unnamed speaker · 23:58
  • Indeed 0:00–0:27
  • Visible 0:30–0:59
  • Indeed 17:46–18:16
  • Talking Real Money 18:25–19:16
  • Visible 19:16–19:49
  • Sam's Club 19:49–20:00
  • McDonald's 20:01–20:16

About this episode

Are High-Yield Investments Dangerously Risky? & Why Wes Updated His Thinking on HSAs Jim Cramer says high yields are dangerous – so is retirement income actually at risk? Wes sets the record straight on high-dividend stocks, interest rates, and how to safely build a yield ladder. Plus, Wes shares a personal shift in his own financial strategy: why he recently updated his thinking on High Deductible Health Plans (HDHPs) and how Health Savings Accounts (HSAs) can become a triple-tax-free powerhouse for your retirement. Mentioned on the show: ⁠ The Overlooked 'Rule of 55' Could Unlock an Earlier Retirement⁠ TIPS: The Inflation-Proof Alternative to Standard Bonds How To Find and Choose a Financial Advisor - Clark Howard Best Financial Advisors in 2026 - Clark Howard All this and more on the October 13, 2026, Ask an Advisor episode of the Clark Howard podcast. Submit your questions: WesMoss.com/ask Discover the research-backed path to a happier retirement – order The Retire Sooner Method by Wes Moss today at retiresoonermethod.com We hope you enjoy our weekly Ask An Advisor episodes. Let us know what you think in the comments! Learn more about Wes: BOOKS BY WES MOSS Wes Moss, CFP® Wes Moss - Clark.com Learn more about your ad choices. Visit megaphone.fm/adchoices

Transcript

0:00
32:56

5,936 words · 8 speakers

Topics

  • HIFO
  • TIPS
  • HSAs
  • S and P 500
  • Vanguard
  • FIFO
  • minimum tax
  • average cost
  • Yahoo Finance
  • 247 Wall Street

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