The Stacking Benjamins Show — Episode SB1740

Strategies and Tactics to Maximize Your 401k (and Common Mistakes to Avoid)
September 26, 2025

Host: Joe Saul-Sehy
Co-hosts/Panelists: OG (absent), Paula Pant (Afford Anything), Jesse Kramer (Personal Finance for Long-Term Investors), Lacey Langford (The MilMoney Show)
Tone: Light, conversational, occasionally irreverent and full of nerdy finance humor

Episode Overview

This episode is a fun yet practical deep dive into optimizing workplace retirement accounts, with a spotlight on the 401k and common mistakes people make. Joe, Paula, Jesse, and Lacey share both big-picture strategies and granular tactics for maximizing retirement savings, covering employer matches, investment choices, fee pitfalls, and special features like Roth options and self-directed brokerage windows. As always, the blend is equal parts friendly banter and functional money advice—with plenty of laughs and some trivia (but don’t worry, we skip the ads and intros).

Table of Contents

• Key Discussion Points and Insights
  • Mistake #1: Missing or Ignoring the Employer Match
  • Mistake #2: Investing Without a Strategy
  • Mistake #3: Underestimating Impact of Fees and Expenses
  • Mistake #4: Overlooking Plan Features and Upgrades
• Notable Quotes and Memorable Moments
• Timestamps for Important Segments
• Panelist Plugs & Closing Thoughts

Key Discussion Points and Insights

1. Mistake #1: Missing or Ignoring the Employer Match (11:00)

Main Takeaways:

• Not knowing or not getting the employer match is a foundational blunder—literally turning down free money.
• In military plans (TSP/Blended Retirement System), members are auto-enrolled, but some still opt out, often for short-term wants (e.g., “buying a new truck”)—a big long-term mistake.
• The consensus: Almost no situation justifies skipping the match—even with high-interest debt.

Panel Insights:

• Joe: “It is so frustrating when I hear people go, ‘I don’t want to give any money to my company.’”
• Jesse: “A fundamental understanding of whether the 401k plan even exists in the first place... The fact that it is a benefit that you as the employee just purely get to benefit from.”
• Lacey: “With the new blended retirement system…they automatically sign you up for the TSP…But a lot of people go in and turn that off…That’s a huge mistake.”
• Paula: “Even if you have credit card debt, the match percentage you’re getting is actually higher than the interest rate you’re paying… it still makes sense to get the maximum match.” (14:24)
• Doug (humorous): “I bet you can find a way—adjust a streaming service, adjust a cell phone plan—so you can find that 5%...” (16:25)

2. Mistake #2: Investing Without a Strategy (21:00)

Highlights:

• Many people get auto-enrolled but never select investments—often leaving large sums in cash by accident.
• Action > paralysis: It’s better to start with something—like a target date fund or a broad index fund—than overcomplicate and do nothing.
• Key initial concepts: Risk tolerance, diversification, and understanding your plan’s menu.

Insights/Quotes:

• Lacey: “You have to more make a move than not make a move… Not looking at it isn’t an option because then it’s just an excuse.”
• Jesse: “If I don’t learn what I’m doing here, I’m going to make some five-figure mistake.” (25:26)
• Paula: “Expertise is the ability to both deep dive and simplify. You have to learn a lot to understand how little you actually had to learn...” (27:13)

Target Date Funds Debate:

• Lacey: “A lot of people just pick [Target Date Funds]... But you should still understand it.”
• Jesse: “If you can construct a diversified portfolio inside a 401k… I would rather someone do that than lean on a target date fund.”
• Paula: “For so many beginners, complexity is the enemy of action.”

3. Mistake #3: Underestimating Impact of Fees and Expenses (46:30)

• Small employer plans often have higher underlying fees. Big companies may get institutional rates.
• High fees can offset even the value of a match if you stay long enough.
• Moving old 401ks: When you leave an employer, you can often roll funds to an IRA or new plan to improve investment choice and cut costs.

Quotes:

• Jesse: “The bigger the company, the more negotiating power your company has…Our fees were .08%. But some plans are 1% plus. That adds up.”
• Paula: “At a minimum, get the match… When you leave that job, you can remove your money from this high-fee account and transfer it to a lower-fee custodian.” (48:31)
• Lacey: “People like, ‘Oh, rolling this over seems like such a pain in the ass.’ I go, 'It’s a bigger pain in the ass if you don’t roll it over.'” (50:40)

4. Mistake #4: Overlooking Plan Features and Upgrades (51:10)

Features Covered:

• Brokerage Windows: Allow greater investment choice, sometimes with lower fees, but often require manual transfers and monitoring.
• Roth vs. Traditional: Roth favored for younger or lower-income savers; traditional for those at peak earnings.
• Automation: Some plans auto-escalate contributions, not always present in military/Govt plans. Use automation or calendar reminders if not.
• Other features: In-plan Roth conversions, mega backdoor Roths, and the importance of avoiding after-tax subaccounts unless pursuing a specific strategy.

Quotes:

• Paula: “[Roth]…everything you put in there, all the growth, all the dividends, capital appreciation, everything is tax-free for life...(54:20)”
• Jesse: “The biggest factor...is understanding the difference between the current tax rates you’re paying, like your current bracket, versus what you might pay when you withdraw that money later. (55:19)”
• Joe: “If you’re not going to do the, the mega backdoor Roth IRA...Do not load up on after-tax money in your 401k because you’re going to create a tracking freaking nightmare.” (60:38)

Notable Quotes and Moments

• On Money Nerd Signs:
  “If you rebalance your portfolio when you balance your checkbook on a Saturday night... you might be a money nerd!” (Paula, 04:15)
• On Risk Tolerance and Getting Started:
  “Understanding where you sit in that, how comfortable you are with a punch in the stomach with money, is really important.” (Lacey, 23:36)
• On Start Simple:
  “For somebody who’s paralyzed and not investing at all, then fine—target date fund.” (Joe, 33:12)
• On Automating Good Habits:
  “Just try it...and you know what’s cool is we can go back to HR and turn it back down later. The number of people that ever came back to me to turn it back down? Not one ever.” (Joe, 20:24)
• On Being Overwhelmed by Old Accounts:
  “Sometimes for peace of mind, it’s better to get them all together and get organized, so that way, the next move isn’t so overwhelming.” (Lacey, 50:57)
• On Roth vs. Traditional (Military):
  “In a very special group of people...can get away with contributing tax-free, and then it growing and withdrawing tax-free.” (Lacey, 54:50)

Timestamps

• 11:00 — Not knowing/using the employer match
• 16:25 — Can you really “not afford” to contribute? Panel’s debate
• 20:24 — Just try increasing your contribution—you won’t miss it!
• 21:09 — Investing without a strategy—cash drag horror stories
• 23:30 — Building confidence in investment selection, target date funds
• 27:13 — When to ask “Why does it depend?”—the decision tree
• 33:12 — How to beat “analysis paralysis” with target date or index funds
• 46:30 — Hidden fees, small company plan problems, to roll or not to roll?
• 51:10 — Extra features: brokerage windows, Roth vs Traditional, automation
• 54:20 — Roth vs Traditional—panel viewpoint breakdown
• 60:38 — After-tax “gotchas” in 401ks

Notable and Memorable Lighter Moments

• The recurring “you might be a money nerd if…” jokes, including “If your favorite four-letter word is ROTH...” (04:24)
• Long-running in-show trivia contest for “Olympic pools worth of beer,” revealing Oktoberfest revelers consumed 2.8 poolfuls in 2024. (43:20)
• Banter about financial “empathy vs. cynicism,” streaming service sacrifices, and whether anyone in history ever missed the extra 5% paycheck deduction (18:03, 20:24).
• “Just try it—nobody ever comes back to lower their contribution.”

After Show & Panelist Plugs

• Jesse Kramer: Highlighting upcoming deep dives on his podcast, especially topics like financial planning with a special needs child. (62:00)
• Paula Pant: Recent “Afford Anything” interviews with David Gardner (Motley Fool), Dr. Daniel Crosby, Andy Hill, and Karsten Jeske. (62:43)
• Lacey Langford: Birthday episode about trademark issues in side hustles/businesses, and episodes on social media’s distortion of financial realities and portable careers for military spouses. (64:09)

Takeaways and Actionable Tips

1. Always get the match (even if you’re in debt)—it’s usually the highest guaranteed return available.
2. Invest with a plan. Read materials, understand choices, and “something” is better than nothing—start simple and refine.
3. Monitor fees. Small employer plan? Factor in high costs and move funds once you change jobs.
4. Watch for useful features. Consider Roth if you qualify, take advantage of automation, but be careful with complex options like after-tax contributions and self-directed windows.
5. Roll over old accounts. Don’t let “convenience” cost you real retirement money in the long run.
6. The “set it and forget it” mindset is dangerous. Always review and update as circumstances (and plan options) evolve.
7. Ask “why does it depend?” When a financial pro says so, dig for the specific decision points.
8. “Complexity is the enemy of action.” Take the path that gets you started—and level up your strategy as you learn.

For More: Check the show notes and all linked resources at stackingbenjamins.com.
Remember: This show is for entertainment and education—consult a pro before making financial decisions!