The Clark Howard Podcast

Episode: Ask An Advisor With Wes Moss

Date: March 3, 2026

Episode Overview

This episode of The Clark Howard Podcast features special guest Wes Moss answering listener questions on personal finance, investment strategies, and retirement planning. Together, Clark and Wes dig into real-world scenarios, covering topics like dollar cost averaging vs. lump sum investments, what to do with an inheritance, consolidating retirement accounts, and why it’s never too late to start saving for retirement. With their trademark practical and reassuring approach, they demystify complex decisions and encourage ongoing participation over chasing perfection.

Key Discussion Points & Insights

1. Travel Plans Gone Awry: Using a Travel Agent

[01:26 - 02:54]

• Wes shares a personal experience where a family trip to Puerto Vallarta was abruptly canceled due to flight issues and chaos in airline travel.
• He credits using a trusted travel agent for making planning and refunds much easier.
• Notable Quote:
  “The very day we had to cancel… we got our money back for the hotel, which I was very relieved about.” — Wes Moss [02:38]

2. Investing: Dollar Cost Averaging vs. Lump Sum ("Cannonball")

[03:04 - 10:33]

• Wes uses a vivid analogy of jumping into cold Lake Michigan—wading in vs. cannonballing—and applies it to investing strategies.

• Dollar Cost Averaging (DCA): Most savers already practice this via regular 401(k) contributions, which helps reduce the emotional ups and downs of investing.

  • DCA is psychologically easier and helps people stay invested over market cycles.

• Lump Sum Investing (Cannonball): Historical data shows lump sum investing usually outperforms, but it’s harder emotionally.

  • Psychological mismatch often occurs when people see new money differently than old investments, but reframing the time horizon helps.
  • “Participation over perfection” is Wes's investment mantra.

• Notable Quotes:

  • “Most Americans are already DCA because if you have a 401k plan, you're contributing. God willing, you are already dollar cost averaging. ...And it's one of the reasons that 401s and retirement accounts...work so, so well.” — Wes Moss [05:10]
  • “The cannonball approach when it comes to investing historically wins because markets tend to go up over time. You are two thirds of the time, so more than half of the time historically you are better off having just cannonballed in.” — Wes Moss [07:03]
  • “Participation over perfection... It's not about being perfect. It's about participating.” — Wes Moss [10:08]

3. Ask An Advisor: Listener Questions

a. Inheritance Decision: Pay Off Mortgage or Invest?

[10:33 - 13:39]

• Listener Cody: Has $85,000 inheritance, low-rate mortgage, no debt except the house.
• Wes highlights the psychological and financial benefits of paying off a mortgage, despite the math sometimes favoring investing.
  • “There is something very powerful about getting rid of the mortgage. ...I have never had one person come back to me and say, ‘Wes, I wish I had not paid off that mortgage.’” — Wes Moss [13:30]
• Clark suggests once the mortgage is gone, the previous housing payment can be redirected to investing via DCA.

b. Early Retirement & Income Calculators

[13:39 - 15:43]

• Listener Greg: Struggles with what to enter as income for healthcare subsidy calculators if retired early with only assets, not income.
• Wes clarifies that eligibility for government health care subsidies is based on income, not assets.
  • “So from everything I know, when it comes to those healthcare supplements from healthcare.gov, doesn't matter what your assets are, it matters what your income is.” — Wes Moss [14:59]

c. Consolidating Multiple Retirement Accounts

[15:43 - 18:04]

• Listener Kyle: Multiple accounts across providers due to job changes.
• Wes emphasizes simplicity and the importance of consolidating accounts when possible for easier management and reduced risk of losing track of funds.
  • “I'm a big believer... just pick one and have an IRA there. ...So yes, I would be a believer that the consolidation into as few retirement accounts as you can do, the better.” — Wes Moss [17:42]

4. It’s Never Too Late: The Math of Catch-up Retirement Saving

[22:07 - 29:09]

• Wes tackles retirement savings psychology, debunking media headlines like “The average American has less than $1,000 saved for retirement.”
• Explains the difference between median and average savings, with more encouraging numbers for active savers.
• Offers detailed math showing how late starters (“Late Start Larry & Lisa”) in their 50s still have a viable path to a healthy retirement by maxing out contributions and staying invested.
  • At age 52, even starting with $50,000, max contributions and prudent investing could yield $1.4 million by retirement.
• Encourages participation and taking action, rather than being paralyzed by late starts or daunting headlines.
  • “It is about participation over perfection… It’s never too late. ...Late start Larry and Lisa can still turn it around.” — Wes Moss [27:27 & 28:42]

5. More Listener Questions

a. Switching to Roth 401(k) at Age 60?

[29:09 - 32:18]

• Listener Lisa: 60 years old, considering switching from pre-tax 401(k) to Roth contributions, living in a high-tax state.
• Wes advises that adding Roth optionality, even late, doesn’t muddy the waters but increases flexibility for future withdrawals.
  • Suggests Roth contributions make sense at her income/tax bracket, and tax-diversifying is valuable for retirement distributions.
  • “When you’re doing distributions, you’re just looking at the menu of your options—brokerage, Roth, traditional—and you want to pick both for the short term today and the long term.” — Wes Moss [30:52]

b. Covered Call ETFs in Retirement Portfolios

[32:18 - 34:54]

• Listener Wayne: Should covered call income ETFs supplement or replace the bond allocation for retirees?
• Wes explains that covered call ETFs produce attractive income but are not a true bond substitute; they are riskier than bonds but less volatile than all-stock portfolios.
  • “I do like these covered call strategies... but they are not a substitute for bonds.” — Wes Moss [33:26]
  • Advocates for multi-asset class portfolios in retirement, using covered call ETFs as one piece.

c. Diversification Beyond Index Funds

[34:54 - 38:41]

• Listener Cory: 40 years old, considering expanding beyond pure stock index funds.
• Wes supports 100% stock allocation at this age and risk tolerance, but highlights benefits (particularly behavioral) of asset allocation and gradual diversification into other classes (international, small caps, commodities, real estate) over time.
  • “Think of asset allocation not just about maxing out your rate of return. It’s creating a portfolio you can be comfortable with that helps the behavioral side of investing.” — Wes Moss [37:35]
  • “Over the long run, having a multi-pillared foundation really helps.” — Wes Moss [38:24]

Memorable Moments & Quotes

• “Participation over perfection.” — Wes Moss [10:08 / recurring theme]
• “Never… have I had a single client come back and say, ‘I wish I hadn’t paid off that mortgage.’” — Wes Moss [13:30]
• “It is about participation over perfection… Late start Larry and Lisa can still turn it around.” — Wes Moss [28:42]
• “When you’re doing distributions, you’re just looking at the menu of your options—brokerage, Roth, traditional—and you want to pick... the most tax-efficient.” — Wes Moss [30:52]

Timestamps for Key Segments

• 01:26 – Travel agent for canceled trips & easy refunds
• 03:04 – Dollar cost averaging vs. lump sum investing: the “cannonball” analogy
• 10:33 – Listener questions begin: inheritance vs. investing vs. mortgage
• 13:39 – Income calculators for early retirees
• 15:43 – Retirement account consolidation
• 22:07 – “Never too late” catch-up savings math
• 29:09 – Roth 401(k) at age 60 & high-tax states
• 32:18 – Covered call ETFs: risks, rewards, and portfolio fit
• 34:54 – Expanding diversification/asset allocation for aggressive investors

Tone & Language

• Clark and Wes keep the conversation upbeat, friendly, and accessible, using practical analogies and real listener questions to make complex financial topics understandable and actionable.
• The show’s discussion repeatedly reassures listeners that no matter their starting point, action and steady participation matter most for building wealth and financial freedom.

Conclusion

This episode encourages listeners to focus on steady participation rather than perfect timing and shows how both new and seasoned savers can improve their paths to financial security. Through relatable anecdotes and step-by-step answers to diverse listener questions, Clark and Wes deliver practical advice that demystifies personal finance and makes financial empowerment achievable for all.