The Clark Howard Podcast

Episode: 09.09.25 “Ask An Advisor With Wes Moss”
Date: September 9, 2025
Host: Clark Howard (absent), guest host Krista, featuring CFP Wes Moss

Episode Overview

This episode of “Ask An Advisor” features personal finance expert Wes Moss and Krista from Team Clark diving deep into retirement and investing questions submitted by listeners. The topics span the disconnect between the stock market and real economy, complex rollover rules (especially for company stock in 401(k)s), early retirement strategies, estate planning pitfalls (with a fun “Davy Buffett” story), brokerage comparison, mortgage payoff dilemmas, and Roth IRA distribution strategies. The tone is educational, approachable, and at times humorous, with Wes drawing on real-life cases and hypothetical scenarios.

Key Discussion Points & Insights

1. Why Is the Stock Market So Strong Amid Economic Uncertainty?

[01:22 – 08:01]

• Wes Moss launches into the “two economies” thesis:
  • Stock market performance vs. Main Street economy: 2025 has been a “really strong year for the S&P 500,” not just tech but also financials, industrials, and utilities are performing well.
  • Disconnection: “The stock market and its performance can very often be disjointed from what’s happening in the economy. We could have a good economy and a bad market.” (Wes Moss, 01:54)
  • Earnings drive stock prices: Despite geopolitical tensions (tariffs, China, Ukraine war, Fed-White House disputes), “earnings from this time last year are up 11, 12, 13%.” Companies are “doing more with less,” i.e., increasing profit margins via efficiency and reduced headcount.
• Labor market concerns: Continuing jobless claims have risen by 13% from early 2024 (1.7M to 1.95M), signaling a cooler Main Street economy even as corporate earnings soar.
• Key lesson: The market “has been tuning out the noise,” focusing on business profits rather than macro/global uncertainties.

2. Ask An Advisor: Listener Q&A

a. NUA (Net Unrealized Appreciation) & 401(k) Rollovers

[08:03 – 11:19]

• Connie from NY: Can I move just the company stock from my 401(k) under NUA rules?
  • Wes explains:
    • NUA allows favorable tax treatment if moving company stock out of a retirement account, but you must roll out the entire 401(k) in that calendar year—can’t pick only the stock and leave the rest.
    • “It doesn’t need to be in a managed account. That can be in your own account, that self-directed IRA that you manage.” (Wes, 10:49)
    • Watch for miscommunication—managed (fee-based) accounts aren’t a requirement here.

b. Retiring Early with Kids at Home

[11:19 – 15:24]

• Jake from NC: Wants to retire at 63, lives frugally, has ~$220K in retirement savings, kids will be 12 and 16.
  • Wes’s take: Jake is “a candidate to wait for Social [Security] and maybe work a little longer.” Drawing down retirement savings before kids are grown has risks—waiting increases security, particularly as Social Security at 70 would nearly cover his target spending.

c. Retiring Very Early & Accessing Funds

[15:24 – 18:55]

• Matt from TX (39): Wants to retire at 50-55, ~$1.5M saved, most in retirement accounts, some in brokerage & 457.
  • Wes: “Your scenario is all about early access.” He describes the Rule of 55 (must leave job at 55+), Rule 72(t) (substantially equal payments for early penalty-free IRA draws), and the advantages of the government 457 plan (withdrawal at any age). Matt’s upcoming inheritance will also provide flexibility for pre-59½ access.
  • “I like the 457. Remember, if you do have an inheritance, that'll be available without penalty...” (Wes, 17:36)

d. Estate Planning Gone Awry: High Profile Celebrity Lessons

[22:15 – 29:47]

• Prompted by stories about Davy Jones, Jimmy Buffett, Aretha Franklin.
• Wes’s parable: “Davy Buffett”—a musician with a well-prepared estate plan, but conflicts still explode between co-trustees and heirs.
  • Disputes arise over wording (primary home vs. vacation home), new-found wills (“couch cushion will”), and interpretation of intentions.
  • Key takeaways:
    • “Even if you have the most buttoned up estate plan, it doesn't mean that people can't sue and trustees can't get along.” (Wes, 27:18)
    • Why plans go wrong: Human relationships, vague wording, old draft documents, and a litigious society.
    • Prevention: Upfront communication and “being really specific” in documents. Destroy old drafts. “Most of the time…things do go pretty smoothly, but we’re going to see from time to time these high profile cases where things have totally gone awry.” (Wes, 29:26)

e. Brokerage Recommendations and Target-Date Funds

[30:00 – 34:25]

• Lisa in CA: Is E*TRADE a good platform, and how about their Trafis (investment research tool)? Are target date funds bad if they get too conservative?
  • Wes: No issue with E*TRADE as a platform; Trafis is an advanced research screener, but always remember back-tests are not future guarantees.
  • On target date funds: “They are an easy button to help people be invested and that's better than not being invested…Do they get usually too conservative? In my opinion, by the time you get to retirement…yes.” (Wes, 33:48)

f. Paying off a High-Rate Mortgage with Retirement Funds

[34:25 – 38:18]

• Chris in MO: 25-year Navy vet, has $2M in retirement accounts, low liquidity, considering using Roth contributions to pay off a 6.25% mortgage.
  • Wes: “Having a mortgage is not some morally wrong thing…It’s a financial tool.” Don't “raid” retirement to pay off the house unless it’s a modest, manageable acceleration using Roth contributions. “One of the ingredients to being a happy retiree is having your mortgage pay off within sight. It's not necessarily paid off, it's paid off within sight, meaning within the next nine years.” (Wes, 36:34)

g. Early Withdrawals from Roth Accounts: Rule of 55 and 72(t)

[38:23 – 40:41]

• Tracy in FL: Can Rule of 55 and 72(t) be used for Roth 401(k) and Roth IRA withdrawals?
  • Wes: “Rule of 55 does work for the 401 and the Roth 401. …The Rule of 72T will work for traditional retirement accounts IRAs, but [doesn’t] apply…to a Roth IRA.” (Wes, 39:19)
  • Roth 401(k): Use Rule of 55 at separation after 55. Roth IRA: Must meet age 59½ and 5-year rule for full tax-free access.

Notable Quotes & Memorable Moments

• "The stock market and its performance can very often be disjointed from what’s happening in the economy…what drives stocks is earnings." — Wes Moss [01:54]
• "They're doing things more efficiently, which is code for they're doing it with less people." — Wes Moss [06:35]
• "You can model the kind of companies that you're looking for [with Trafis]...but it does empower you to invest in the kind of companies or the kind of metrics you feel comfortable with." — Wes Moss [32:26]
• “Estate planning, I would say, is as much about the people as it is the paperwork…humans can make this messy really easily.” — Wes Moss [28:53]
• “One of the ingredients to being a happy retiree is having your mortgage pay off within sight. It's not necessarily paid off, it's paid off within sight, meaning within the next nine years.” — Wes Moss [36:34]
• “Rule of 55 does work for the 401 and the Roth 401…The Rule of 72T will work for traditional retirement accounts IRAs, but they don't apply…to a Roth IRA.” — Wes Moss [39:19]

Timestamps for Key Segments

• 01:22 – Stock market vs. Main Street economy
• 08:03 – Company stock in 401(k)s, NUA rules
• 11:19 – “Super saver” retiring at 63 with young kids
• 15:24 – Early retirement and penalty-free access strategies
• 22:15 – Estate planning: celebrity disasters & Davy Buffett
• 30:00 – Evaluating E*TRADE, Trafis, and target date funds
• 34:25 – Should you use Roth contributions to pay off a house?
• 38:23 – Rule of 55 & 72(t) for Roth accounts
• 40:41 – Episode wrap-up

Takeaways

• The market can disconnect from the economy—investors should focus on company fundamentals, not just economic headlines.
• Tax and access rules around retirement accounts (NUA, Rule 55, 72(t)) are complex but can be leveraged for greater flexibility—expert guidance pays off.
• Estate planning must balance good legal documents with clear family communication. Human factors are often the source of problems, not faulty paperwork.
• Mortgage payoff decisions should balance financial math (“tax tsunami,” compounding returns) with peace of mind—there’s no moral imperative, but a plan helps.
• Use the right tools for your investing style and stay informed about the changing rules—“easy buttons” like target date funds are useful but not perfect.

For more listener questions or to submit your own, visit clark.com/ask. Clark Howard returns in the next episode.