The Clark Howard Podcast

Episode: Ask An Advisor With Wes Moss (10.14.25)
Date: October 14, 2025
Host: Clark Howard | Guests: Wes Moss, Krista Dibias

Overview

This episode of “Ask An Advisor” dives deep into listener financial questions with guest advisor Wes Moss and co-host Krista Dibias. The team examines the state of the current bull market, provides historical context for potential market moves, answers specific investing dilemmas (from mortgage pay-down strategies to 529 plans for children and timing the market), and tackles the important difference between being “set” vs. being “settled” financially. The tone is conversational, plainspoken, and upbeat, with particular emphasis on practical, consumer-first advice that mirrors Clark Howard’s trademark approach.

Key Discussion Points and Insights

1. The State of the Bull Market: Where Do We Stand?

[02:04 – 09:28]

• Wes reviews the three-year anniversary of the current bull market, observing that stocks have risen significantly, with the S&P 500 up about 92% in total return over the past 36 months.
• Historical context: The average bull market lasts around 58 months (just under five years) with an average return of 172%.
• Positive indicators: “History is very much on our side for markets to continue to be strong.” – Wes Moss, [03:03]
• However, concerns about froth and overvaluation are flagged, especially with current price-to-earnings (PE) ratios elevated at about 28x, reminiscent of the late 1990s dot-com era.
• The job market has shifted to equilibrium, and home price appreciation has largely stalled (“only risen about 1.6%”).
• AI enthusiasm is driving huge investments — e.g., OpenAI’s $500 billion valuation — suggesting the market’s “little bit of exuberance.”
• Wes emphasizes the need for investors to remain patient, consider portfolio rebalancing if exposed to excess stock risk, and remain vigilant about their planned stock-bond allocation.
• Notable Quote:
  “If you originally said, ‘I’m comfortable only having 50% in stocks and now that’s 75%,’ just understand that your portfolio has gotten a lot riskier... Just do a gut check.”
  — Wes Moss, [08:37]

2. Listener Q&A: Focus on Real-Life Money Decisions

a. Pay Down the Mortgage or Buy Bonds?

Jason in Utah
[09:47 – 15:37]

• Jason has $300k in a note (earning 4.5%), $900k in a brokerage account (mostly S&P 500), and a sizable 401(k). Wondering whether to use $200k to pay down a 4.375% mortgage or invest in bond funds with “uninspiring” returns.
• Wes’s take: If you can pay off the mortgage with a third or less of your after-tax money, do it.
  “Happy retirees either have a paid off mortgage or are getting close…even though it’s a low rate, you’ll be more comfortable in retirement without the burden.” — Wes Moss, [12:35]
• Bond returns should track today’s yields (“yield is destiny”), but those are close to the mortgage rate; paying off the mortgage is “somewhat of a guaranteed rate of return.”
• Lean: Use after-tax money to pay down the mortgage for tax flexibility and retirement comfort.

b. How Does a 401(k) Track Traditional vs. Roth Money?

David in Ohio
[15:37 – 17:47]

• David wonders how providers track which dollars are traditional vs. Roth, especially after rebalancing.
• Wes explains: Each deposit and its earnings are “tagged” by tax type in the system, even though it appears as a single pie chart.
• Industry systems are heavily audited and regulated, so they “don’t mess this up.”

c. UGMA vs. 529 Plan for a 10-Month-Old Niece

Derek in New Hampshire
[17:47 – 21:29]

• Derek would rather invest for his niece than buy toys. Debates a flexible UGMA custodial account vs. the more restrictive 529 college plan.
• Wes’s view: 529 plans are now more flexible (thanks to Secure 2.0, allowing rollovers to Roth IRAs), and offer significant advantages if not used for college.
  “You can…convert that into a Roth, which is a jump on retirement.” — Wes Moss, [20:23]
• UGMA/UTMA accounts become the child’s at age 18/21 and have some tax drawbacks (kiddie tax).
• 529s impact FAFSA less and can jumpstart retirement savings.

3. Deep Dive: “Set But Not Settled” — Why Rich People Still Worry

[24:29 – 32:49]

• Wes introduces the concept: Many people are “set” financially but not “settled” emotionally.
  • “Set” means having plenty of money; “settled” means truly feeling at ease.
  • Even high-net-worth individuals share similar anxieties as those with less wealth, especially around retirement and market cycles.
• Holistic planning is essential: Not just financial assets, but also taxes, distributions, estate planning, lifestyle, hobbies, and the psychological side.
• Recurring risks: Concentrated stock holdings, sequence of returns, withdrawal strategies, tax planning, long-term care, and estate questions.
• The antidote to anxiety: Have a constantly evolving plan and revisit it regularly.
  “No plan means no peace.” — Wes Moss, [28:48]
• Notable Quote:
  “Just because they have more assets doesn’t mean all of a sudden everything’s set. In fact, sometimes there’s more problems.” — Wes Moss, [28:17]
• Ultimately: True financial freedom comes from a combination of being “set” and “settled”; planning is the bridge.

4. Rapid-Fire Q&A: Practical Financial Advice

a. How Do Asset Fees Work—Are They Hidden?

Andrew in Iowa
[32:49 – 34:23]

• Andrew asks how mutual fund/ETF fees are collected.
• Wes clarifies: Fund fees are taken from the fund on a daily, pro-rata basis and are baked into price performance; investors don’t need to track them separately.

b. Finding a Plain-Speaking Financial Planner

David in Massachusetts
[34:23 – 42:03]

• David has ~$3.5 million, feels lost during technical explanations, and wants actionable, plain English advice—ideally for a flat or hourly fee.
• Krista and Wes agree: You should never feel confused by your advisor.
• Wes’s tips:
  • Visual learners should have planners use drawings and visual aids.
  • Keep asset allocation simple (consider 50/50 stock/bond as Buffett’s mentor Graham suggested).
  • Consider hybrid approaches: manage some assets yourself, use a low-cost advisor for planning (Vanguard’s service is cited at 0.35%), or pay an hourly planner (rare but available).
  • Important:
    “Investing at its core is just a blend of risky assets (stocks) and safety assets (bonds/cash)…it can be that simple.” — Wes Moss, [39:20]

c. Should I Wait For the Market to Drop Before Investing?

Leslie in North Carolina
[42:04 – 44:14]

• Leslie is waiting for a better entry point into “VO” (Vanguard S&P 500 ETF) but the market keeps rising.
• Wes diagnoses: This is market timing (even if only with new cash), and it rarely pays.
• Solution: Trick yourself with dollar-cost averaging—invest a set amount regularly, smoothing out entry points and psychological stress.
  • “DCA is the only way to trick yourself into being invested.” — Wes Moss, [43:05]

Notable Quotes

• “History is very much on our side for markets to continue to be strong.”
  — Wes Moss, [03:03]
• “Happy retirees either have a paid off mortgage or are getting close…even though it’s a low rate, you’ll be more comfortable in retirement without the burden.”
  — Wes Moss, [12:35]
• “No plan means no peace.”
  — Wes Moss, [28:48]
• “Just because they have more assets doesn’t mean all of a sudden everything’s set. In fact, sometimes there’s more problems.”
  — Wes Moss, [28:17]
• “You should never feel confused when you talk to your financial planner.”
  — Krista Dibias, [35:17]
• “Investing at its core is just a blend of risky assets (stocks) and safety assets (bonds/cash)…it can be that simple.”
  — Wes Moss, [39:20]

Timestamps for Key Segments

• Market Review & Bull Market History: [02:04 – 09:28]
• Jason’s Mortgage Dilemma: [09:47 – 15:37]
• 401(k) Roth/Traditional Tracking: [15:37 – 17:47]
• UGMA vs. 529 Question: [17:47 – 21:29]
• Set But Not Settled (Deep Dive): [24:29 – 32:49]
• Asset Fee Mechanics: [32:49 – 34:23]
• Plain-Spoken Planners: [34:23 – 42:03]
• Market Timing & Dollar Cost Averaging: [42:04 – 44:14]

Memorable Moments

• Krista and Wes’s banter over the need for simplicity and visual aids in financial planning [37:32 – 37:49].
• Wes’s candid admission of the universality of retirement anxiety, regardless of portfolio size [28:17].
• The light-hearted acknowledgement of how “set it and forget it” is a myth in financial planning [28:48, 31:17].
• Clark audience humor: “I’d rather give them money than clothes they’ll outgrow. That’s such a Clark audience thing to say.” — Wes Moss, [19:57]

Summary

This episode blends a timely market outlook with practical, nuanced answers to listener dilemmas. Whether it’s about staying disciplined during a long bull market, handling the “good problems” of surplus savings, or simply tricking yourself into investing when it feels uncomfortable, the core message is clear: financial empowerment requires both planning and psychological awareness. The show’s strength is in plainspoken guidance and a down-to-earth tone, keeping it accessible and actionable for listeners at every stage of their financial journey.