The Clark Howard Podcast: Ask An Advisor With Wes Moss

Date: April 7, 2026
Host: Krista DiBiase with Advisor Wes Moss
Episode Theme: Overcoming Financial Fears: Speculative Investing, Retirement Decisions, and Your Questions Answered

Episode Overview

This Ask an Advisor episode features Wes Moss answering listener questions on investing, annuities, lump sum pensions, and diversification. The discussion centers around the growing anxiety Americans feel about being behind on savings, often resulting in risky decisions. Wes underscores the power of long-term, patient investing and addresses nuanced retirement planning questions, aiming to help listeners avoid major pitfalls on the path to financial freedom.

Key Discussion Points & Insights

1. Feeling Behind: The Speculation Trap (00:21–08:00)

• Main Issue:
  Many Americans—particularly younger generations—feel they're behind on retirement savings and are turning to speculative investments to play catch-up.
• Wes’s Analogy:
  Feeling behind is like "being in the fourth quarter and just throwing up threes... Hail Mary passes." (00:47)
• Stats from Northwestern Mutual:
  • 73% of all adults feel behind financially.
  • 80% of Gen Z, 75% of Millennials, 66% of Gen X, and 51% of Boomers report this feeling.
  • Younger people are more likely to turn to speculative assets: cryptocurrencies, meme stocks, sports betting.
• Accessibility Issue:
  These investments are more accessible than a decade ago, making impulsive betting easier.
• Planning Makes a Difference:
  71% of people who work with a financial advisor feel secure versus much lower rates among those who don't.
• Wes’s Prescription:
  “We're not behind. If you're in your 30s, you’ve got three decades of investing ahead. Build wealth through long-term patient accumulation, not lottery ticket investments.” (06:21)

2. Listener Q&A: Practical Guidance

A. Alternative Options for a Maturing Annuity (08:01)

• Mary (TX):
  Has a $200K fixed three-year annuity maturing, not renewing, doesn’t want to invest in stocks/IRA.
• Wes’s Advice:
  Suggests staying in safe, liquid options—like US Treasury money markets or short-term bond ETFs—with yields of about 3.5%-4%. Stresses minimal risk, especially when risk avoidance is a priority. (08:22)

B. How Do Dividends Really Work? (10:00)

• Bob (GA):
  Asks about the real impact of dividends versus interest, questioning if dividends just reduce share price.
• Wes’s Breakdown:
  Explains that historically, a third or more of US stock market returns come from dividends reinvested.
  • “If you look at the US stock market, the return is 10%…without dividends, it's 6%. A third of total returns are from dividends.” (11:49)
  • “Dividends give companies discipline and provide steady income to shareholders.” (13:01)
  • “It’s not just your own money coming back to you–it’s a critical part of real, long-term growth.” (13:25)

C. Should We Pay Down a Mortgage or Invest? (14:16)

• Christina (CO):
  Couple in late 30s, $300K after selling a house, considering applying it to a new mortgage (now $600K) or investing.
• Wes’s Take:
  No right/wrong answer; personally would prefer investing for the long-term, leveraging the power of compounding (“Rule of 72: Money doubles every 10 years at 7.2% returns”).
  • “You’re not at the end of the game; you’ve got four quarters ahead. Doubling that $300K could mean $1.2 million in your 50s.” (15:24)

3. Lump Sum Pension vs Annuity Payments – The "Pot of Gold Trap" (23:51–28:24)

• Alarming Statistic:
  “One out of five people who take a lump sum from a pension run out of money—on average, in four and a half years.” (23:51)
• Wes’s Cautions:
  • Lump sums create temptation. Unexpected large sums can increase spending on big purchases, sometimes violating safe withdrawal rates.
  • Flexibility vs. Discipline: Lump sums offer flexibility and legacy potential, but only if managed with discipline to convert them to "your own paycheck engine," simulating an annuity with proper guardrails.
• Context Note:
  The study comes from MetLife, an annuity provider, so Wes urges listeners to “know where the data comes from.” Still, the risk is real.

4. Listener Q&A, cont.

A. Proper Stock-to-Bond Mix for Elderly Parents (28:24)

• David (CA):
  Manages finances for elderly mother/mother-in-law; advisors recommend a 60/40 equity/cash split, but he cites "age from 100" rule for stocks.
• Wes’s Take:
  That old rule is "overly crude.” For many families, the investment time horizon spans generations, so higher stock allocations can be appropriate—sometimes even 50–70%.
  • “If your withdrawal rates and time horizons support it, more equity can make sense. Just don’t blindly follow outdated rules.” (29:15)

B. Multi-Year Guaranteed Annuity (MYGA) vs. CDs (32:53)

• Michelle (WA):
  Wonders about MYGA annuities, pitched as “the CD of annuities.”
• Wes’s Caution:
  • “There’s no new magical annuity. At the end of the day, it’s just a fixed annuity–but with far less safety than federally-insured CDs."
  • MYGA guarantees are only as good as the insurance company making them—not FDIC. Less liquidity and more hassle if you need to access funds early.
  • “You’re trading a little higher yield for less safety and more complexity.” (33:51)

C. Managing RSUs and Diversification Before Early Retirement (36:58)

• Billy (GA):
  At 45, wants to retire at 55; company RSUs now make up 30% of his investments. Asks about selling/diversifying without tax “bomb.”
• Wes’s Strategy:
  Pay ordinary income tax at vesting. Recommends steadily diversifying—reduce RSUs from 30% to 15–10% of portfolio over a few years, managing realized gains to stay in lower capital gains brackets and avoid 3.8% NIIT when possible.
  • “There are no companies immune to drawdowns. Gradual diversification keeps risk in check and manages taxes.” (37:45)

Notable Quotes & Memorable Moments

• Wes Moss on Risky Investing:

  “Why go for a 1 in 10,000 chance when you really have almost a 100% chance to get to financial freedom?” (07:00)

• On Dividend Returns:

  “A third of the total return of the US stock market over the last 50, 100, 150 years is because of the dividends getting reinvested.” (12:17)

• On Lump Sums:

  “One in five folks just run out ... in about four and a half years. It’s the pot of gold syndrome.” (23:51)

• On Rules of Thumb:

  “That ‘100 minus age’ adage is directionally correct but mathematically, overly crude.” (29:15)

• On Annuity Guarantees:

  “There’s no stronger guarantee on planet Earth than FDIC, but annuity guarantees are only as good as the company behind them.” (34:30)

• On Diversification:

  “There are no companies that are totally impermeable to their stock price going down.” (39:15)

Timestamps for Key Segments

• Feeling Behind and Speculative Investing: 00:21–08:00
• Annuity Alternatives (Mary in TX): 08:01–10:00
• Dividend Mechanics (Bob in GA): 10:00–14:16
• Mortgage Paydown v. Investing (Christina in CO): 14:16–17:22
• Pot of Gold Trap: Lump Sum vs. Annuity: 23:51–28:24
• Elderly Family Allocation (David in CA): 28:24–32:53
• MYGA v. CD (Michelle in WA): 32:53–36:58
• RSU Diversification (Billy in GA): 36:58–40:34

Episode Tone

Upbeat, direct, sometimes humorous; practical and forthright advice underscored by data and war stories. Emphasis on the long view, measured optimism, and protecting against human nature’s financial missteps.

Takeaways

• Feeling behind is normal, but don’t respond by gambling your future; long-term, patient investing is the sure path.
• Lump sum pensions require discipline or you could outlive your money.
• Dividend reinvestment is a foundational, often underappreciated force in building wealth.
• Don’t be mesmerized by high-yield annuities—always know who guarantees your money (FDIC vs. insurer).
• Diversify from concentrated holdings (like RSUs) gradually, managing taxes along the way.
• Old rules-of-thumb are a starting point—not a substitute for holistic personal planning.

For personalized questions or more, submit at clark.com/ask and specify “Wes” for investment topics.