The Clark Howard Podcast

Episode: Ask An Advisor With Wes Moss

Date: September 16, 2025

Overview

In this episode of "Ask An Advisor," Krista Dibiaz and Wes Moss tackle listeners' investing and retirement questions, focusing on navigating both strong and challenging market conditions. Wes—drawing on 25 years of financial experience and dedicated happiness-in-retirement research—lays out his 5 Pillars of Investing, dives into hot listener topics (from the 4% rule to custodial savings for teens), and breaks down major upcoming tax law changes, offering actionable insights for retirees and savers in every stage of life.

Key Discussion Points and Insights

1. The Psychology and Mechanics of a Happy Retirement

• Main Point: Wes Moss emphasizes that financial security is necessary, but not solely sufficient, for a happy retirement. Emotional wellbeing and social habits matter, too.
• Quote:
  "One of the keys is to be able to get to retirement and be able to say yes to retirement. And there are absolutely some financial checkpoints we need to get to. And there's still one of the primary fears in America... that's running out of money." — Wes Moss (01:20)

2. The Five Pillars (or Foundations) of Successful Investing

Full Segment: 03:58–10:07

Wes lays out his guiding principles for long-term investing, applicable in any market climate:

a. Participation Over Perfection

• Investing is a continuous journey. Don’t try to time the market or wait for perfect conditions.
• Quote:
  "Investing is a perpetual event... In good times, there’s challenges, and bad times, there’s challenges." — Wes Moss (05:01)

b. Rational Optimism

• Maintain a positive but realistic outlook. Believe in long-term progress, especially in the U.S. “army of American productivity.”
• Quote:
  "What drives my rational optimism is... 165 million people… more productive, we produce more, companies do more, earn more." — Wes Moss (06:20)

c. Stock Ownership & Asset Growth

• Stocks and real estate generally outpace inflation over time, critical for long-term wealth.

d. Safety Assets (“Dry Powder”)

• Hold a portion in high-quality bonds or money markets to buffer volatility and support disciplined stock investing.

e. Diversification

• Avoid concentration risk in stocks, sectors, or other assets.
• Quote:
  "I still see over and over again examples of people that are overly concentrated in one area. Nothing lasts forever in this market." — Wes Moss (08:54)

f. Time, Patience, and Behavior

• Emotional discipline and long-term perspective are as crucial as the math.

Notable Note:

• S&P 500, with dividends reinvested, up over 600% since 2000, despite volatility. (09:58)

3. Listener Q&A Highlights

• Diversification Beyond the S&P 500 (Sam in Utah)

[11:01]

• Sam asks about broadening beyond S&P 500 via the URTH ETF (MSCI World Index), which includes international exposure but has a higher expense ratio.
• Wes’s Advice: Diversification is good, but check fund details. U.S. mega-caps dominate even global indices. Consider adding international funds or equal-weighted U.S. ETFs for better balance, and mind expense ratios.

• The 4% Rule and RMDs (David in Oregon)

[13:47]

• David inquires how required minimum distributions (RMDs) relate to the "4% rule" for retirement withdrawals.
• Wes’s Guidance: Only withdrawals actually spent (not simply moved between accounts or reinvested) count towards the 4% rule. Taxes withheld do count.
• Memorable Moment:
  "Interestingly, just this week... a family that I work with... sent me a USA Today article about William Bengen... evidently his original rule... was 4.15%... Bengen... has upped his withdrawal rate to 4.7%." — Wes Moss (15:09-15:50)

• Tax Basis and Tax Harvesting (Michael in Georgia)

[17:02]

• On cost basis: Vanguard often defaults to cost average. Consider checking with the provider and electing specific-lot identification before selling.
• On tax harvesting: Sell losing holdings to offset gains. Selling winners can also reset cost basis (“tax gain harvesting”).

• Long-Term Capital Gains and New Senior Tax Deductions

[22:55–30:25]

• Major new tax law (“one big beautiful tax bill/act”): Extra $6k deduction per person 65+ for 2025-2028.
• Strategic window to lower taxable income, maximize Roth conversions, and manage capital gains in the 0% tax bracket (for joint filers up to $96,700 taxable income).
• Warning: Scenarios are complex—consult a tax pro.
• Quote:
  "How do we stay in the zero percent [capital gains] category?... all of your income ... goes to the mix of calculating your net taxable income." — Wes Moss (26:44)

• How to Plan with Temporary Tax Deductions (Helen in Georgia)

[30:31]

• Take advantage now. Use window for Roth conversions or harvesting gains while deductions last. Tax law is ever-changing.
• Quote:
  "What we need to do is just take advantage of [these deductions] while we can." — Wes Moss (31:20)

• Investing for Teens and Short-Term Goals (Kate in Alaska)

[33:18]

• For kids with 1–2 year time horizon: Stick to money market funds for safety.
• For longer horizon (5–6+ years): Mix stocks and safety assets (e.g., 50% total market ETF, 50% money market/bonds).
• Quote:
  "John Bogle... famous for saying... any time Horizon Less than 10 years is speculation. But I would say he’s somewhat of an extremist..." — Wes Moss (33:18-33:48)

• Brokerage Choice and Account Security (John in New York)

[35:09]

• Big custodians (Fidelity, Schwab, Vanguard) provide security—Wes is also comfortable with E*Trade (now part of Morgan Stanley). Know exactly who holds your assets for peace of mind.
• Quote:
  "The very first thing to think about is the custodian... Know where your money’s being held." — Wes Moss (36:35)

Notable Quotes and Timestamps

• "It's running out of money. People are just... fearful of what if this doesn't last. So if we can solve that part of the equation, you can feel comfortable..." — Wes Moss (01:20)
• "Participate as investors for as long as we can and not get thrown off." — Wes Moss (04:47)
• "I believe in the army of American productivity." — Wes Moss (06:26)
• "Nothing lasts forever in this market." — Wes Moss (08:57)
• "S&P 500 is... up over 600% [since 2000] with dividends reinvested." — Wes Moss (09:58)
• "Only things that count towards the 4% rule are money that is spent." — Wes Moss (14:05)
• "[William] Bengen... has upped his withdrawal rate to 4.7%." — Wes Moss (15:50)
• "How do we stay in the zero percent [capital gains] category? ... all of your income... goes to the mix..." — Wes Moss (26:44)
• "Take advantage of these... deductions... and utilize them to their fullest..." — Wes Moss (31:20)
• "John Bogle... any time Horizon Less than 10 years is speculation. But I... don't totally agree with him." — Wes Moss (33:21)
• "Know where your money's being held. And that's a great exercise..." — Wes Moss (36:42)

Timestamps for Important Segments

• [03:58] — Five Pillars of Investing Introduced
• [11:01] — Diversification Beyond S&P 500 (Sam/URTH ETF)
• [13:47] — The 4% Rule & RMDs (David in Oregon)
• [17:02] — Cost Basis, Tax Harvesting (Michael in GA)
• [22:55–30:25] — New Tax Law, Managing Cap Gains
• [30:31] — Leveraging Temporary Tax Deductions (Helen in GA)
• [33:18] — Investing for Teens’ Short-Term Needs (Kate in AK)
• [35:09] — Brokerages & Asset Security (John in NY)

Tone and Style

Friendly, practical, and empathetic—true to the Clark Howard/Team Clark mission of equipping listeners to make better, more confident financial decisions. Wes Moss shares technical expertise in approachable bites, always circling back to actionable wisdom and reinforcing that the ultimate goal is financial security and happiness.

Summary for Quick Reference

• Investing success hinges on rational optimism, broad diversification, discipline, and understanding your own behavior—not outguessing the market.
• New 2025–2028 tax law provides extra deductions for seniors; retirees should be proactive about capital gains and Roth conversions while the window is open.
• For short-term goals (under 3 years), safety comes first; for longer horizons, mix in equities.
• Big, reputable custodians (e.g., Fidelity, Schwab, Vanguard) are safest for holding assets; always verify where your investments are actually custodied.
• Manage retirement withdrawals carefully—only what you spend counts as a withdrawal.
• Consult professionals for personalized tax planning, as upcoming changes are both impactful and complex.