Money Guy Show Podcast Summary

Ep: Has the Stock Market Hit the Top? | Ask Money Guy

Date: January 21, 2026
Hosts: Brian Preston & Bo Hanson

Episode Overview

This episode tackles the perennial question: "Has the stock market hit the top?" Brian and Bo challenge media fearmongering around market highs, explore investor anxieties about downturns, and remind listeners of the importance of focusing on long-term wealth-building fundamentals. They respond to live audience questions relating to Roth conversions, home buying, 401k rollovers, the financial order of operations, 529 plans, and making smart choices about car purchases. The tone is educational, straight-talking, and often laced with humor and personal anecdotes.

Key Discussion Points & Insights

1. Stock Market at All-Time Highs: Should You Be Worried?

Timestamps: 00:06–09:52

• Common Cycle: Every time the market hits all-time highs, sensational negative headlines emerge, causing fear and uncertainty among investors.
• Brian’s Perspective:

  “I’ve kind of gotten numb to [all-time highs], but with that comes trolls crawling out from under the bridges... This is fear gets people to do things.” (00:35)

• Media Fear-Mongering: Bo lists alarmist headlines predicting unseen bear markets and multiple bubbles bursting.
• Market Predictions:

  "Nobody knows what's going to happen in the next year, two years. Nobody else does for that matter, no matter how many... newsletters or whatever they're trying to sell to you." – Brian (03:25)

• Important Insight: Temporary downturns are normal, and no one can consistently time market highs and lows.

2. The Power of Zooming Out: Perspective on Market Volatility

Timestamps: 03:25–08:59

• Historical Perspective: Sharp market drops (like Black Monday, the dot-com crash, and the Great Recession) look minor when viewed on a long-term graph.
• Staying Invested Pays:

  “When we zoom out... it seems like the deck is stacked in our favor. If you don't believe us, look at...” – Bo (04:49)

• Win Rates:
  • S&P 500 is positive ~54% on a daily basis; ~80% positive year-to-year.
  • At 5 years: 93% chance of gains; at 7 years: 100%.
• Consistency is Key:

  “By the time we get to five years, we're at 93%. You see six years, we have the pop up to 98, seven years, 100.” – Brian (06:45)

3. Control the Controllables

Timestamps: 07:56–09:52

• Key Takeaway: You can't control market performance, but you can control your savings rate, investment consistency, risk tolerance, and behaviors.
• Bo's Call to Action:

  “What the market does in any given year is outside your control... We want you to control the controllables.”

• Actionable Advice: Follow the ‘financial order of operations’ (the Foo)—a step-by-step guide for what to do with your next dollar, regardless of market conditions.

4. Audience Q&A – Wealth Building & Financial Decision-Making

Timestamps: 10:28–66:00

a) Market Valuation & Roth Conversions

• Question: Does current market valuation impact when to do a Roth conversion?
• Answer: Focus primarily on tax bracket arbitrage, not market timing. If the market drops significantly, that's a good opportunistic time for conversions, but don't “get too cute” trying to time highs/lows.

  “Tax rate matters first... If this is a material sum of money ... timing does matter. If just a small sum, wait till fourth quarter.” – Brian (12:42)

b) First Time Home Buying in the Foo

• Question: When should buying your first home fit into the financial order of operations?
• Key Tips:
  • 3–5% down is typical for first homes (contrary to the 20% myth).
  • Buying a home isn’t a literal step in the Foo, but usually fits as you finish building your emergency fund (step 4).
  • Ensure you can stay in the home for 5–7 years to offset transaction costs.

  “Nobody's putting down 20% on their first home... If you go to moneyguy.com/resources we have tons of tools...” – Bo (17:52)

c) 401k Rollover: New Job vs. Solo 401k

• Question: Should I roll my 401k into a new employer plan or a solo 401k from a side gig?
• Necessities: Consider investment options, cost, and the Solo 401k $250,000 filing threshold (after which a 5500 is required annually).

  “Solo 401ks are beautiful... no reporting until assets cross $250,000... If you’re not super organized, it could be justifiable to roll into a new employer 401k.” – Bo (22:32)

• Pro Tip: Only one salary deferral limit applies across all 401ks.
• Decision Matrix: Refer to resources at moneyguy.com for a detailed breakdown.

d) Catching Up on Retirement Savings

• Question: 37 years old, $100k invested, $230k income, saving 35%. “Milestones seem to run away.”
  • Advice: Use a three-year average income to “smooth out” for benchmarking.
  • Rapidly rising income means you’ll feel behind, but high savings rates (35%+) can close the gap fast.

  “Bigger your lifestyle gets, more your money must replace at financial independence.” – Bo (32:25) “Your dollars still have a lot of juice in there... you can make up for lost time.” – Bo (34:48)

• Suggested Resource: ‘How Much Should You Save?’ deliverable at moneyguy.com/resources.

e) No Employer Benefits – What Now?

• Question: What if you can't access a 401k, HSA, etc.?
• Answer:
  • Lobby for a 403b if possible at a nonprofit.
  • Max out Roth IRAs; after that, invest in a taxable brokerage account—still plenty of wealth-building opportunity.

  “There's still a lot of opportunity to let your money work harder... even in a taxable brokerage account.” – Brian (37:17)

f) 529 College Savings: Overfunded & Unused

• Question: What if my kid doesn't use the $100k in their 529?
• Options:
  1. $35,000 can be rolled into a Roth IRA for the beneficiary, subject to annual limits and timeframe rules.
  2. 529s can also fund trade school, professional certifications, or even be transferred to future grandchildren.
  3. Withdrawals for non-qualified use are only taxed/penalized on gains, not contributions.

  “A little goes a long way... Don’t go crazy with funding.” – Brian (54:05)

• Note: The Roth IRA 'bailout' route isn’t meant as a planning strategy; more a safety valve.

g) Buying a Car: Cash or Finance? (Step 7, 32% Savings Rate, Age 29)

• Question: Should I pay cash for a car using half my emergency fund or finance?
• Considerations:
  • Weigh impact on your financial stability—how quickly can you rebuild the emergency fund?
  • If financing at a very low interest rate is an option, may make sense to do so and keep more money invested.

  “If you go buy the nicer car... am I going to constantly kick myself over the opportunity cost?” – Bo (62:11)

• Caution: Undershoot what you can afford; resist ego buys. The “luxury vehicle” should come only after you’re well established.

  “The vehicle is probably one of the last places that should be an indicator of your success.” – Brian (59:50)

Notable Quotes & Memorable Moments

• “When in doubt, zoom out.” – Brian (03:25)
• “No one knows what the market’s going to do over the next year or two. Control the controllables.” – Brian (08:59)
• On 529s: “A little goes a long way... grandma covered half a year of your college with just $2,000 at birth.” – Brian (53:09)
• On car buying: “Chicken nuggets under the seat of a luxury car are just as gross as they are under the seat of an Accord.” – Bo (65:11)

Fun, Light-Hearted Segments

• Extended banter about childhood (feral 80s kids), monster trucks, first Kiss albums, and the joys/perils of spending spring break in Panama City.
• Running jokes about “gross” words, boomer vs. millennial references, and community shout-outs (“Legend!”).

Actionable Takeaways

• Ignore market noise: Stay invested, zoom out, and stick to your plan.
• Control only what you can: Your savings rate, behaviors, and investing discipline.
• Use the ‘financial order of operations’ for step-by-step decision making.
• Seek opportunity in volatility (i.e., Roth conversions when markets are down).
• Don’t overthink timing on Roths, rollovers, or home buying—be practical and consistent.
• Car buying: Undershoot your ego, overshoot your future.
• Utilize free resources at moneyguy.com/resources.

Important Timestamps

• 00:06 — Has the market hit the top? Tackling fear headlines
• 03:25 — Historical perspective: Zoom out!
• 06:45 — S&P 500 win rates by time horizon
• 10:54 — Timing Roth conversions in high/low markets
• 16:40 — First-time home buying and the Foo
• 21:58 — Old 401k: Roll to new employer, solo 401k, or stay put?
• 30:53 — Catching up on retirement savings as income accelerates
• 35:05 — Building wealth without 401k or HSA access
• 48:30 — 529 plan overfunding: What now?
• 57:48 — Buying a car: Cash vs. financing, and avoiding early lifestyle creep

For More:

Podcast and resources: moneyguy.com/resources

This episode delivers a reassuring, insightful, and practical guide through market noise, wealth-building strategies, and good old-fashioned common sense. Whether you’re new to investing or a seasoned “financial mutant,” Brian and Bo make sure you’re ready to face whatever 2026 markets throw your way—with perspective, confidence, and maybe a little tongue-out calculator face for good luck.