Podcast Summary: The Stacking Benjamins Show
Episode: How to Sidestep the 4 Culprits Wrecking Middle Class Retirement
Date: September 15, 2025
Hosts: Joe Saul-Sehy, OG, and Doug
Overview
In this lively episode, Joe, OG, and Doug dig into a pressing—and clickbaity—headline: “The Number One Habit that Destroys Middle Class Retirement Dreams.” The team debunks the sensationalism, breaks down the genuine threats to a secure retirement for the American middle class, and shares practical advice, real-life stories, and a heaping side of humor. Beyond the main topic, the episode features a critique of trendy ETF picks, a “second opinion” on stock splits and taxes, and an invitation for community engagement, all keeping with the Stacking Benjamins balance of fun and function.
Main Discussion: The Top Four Habits Wrecking Retirement
Breakdown of the “Culprits”
(Segment begins at ~09:09)
Despite the headline promising “one habit,” the article referenced in the show actually identifies four critical bad habits:
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Carrying High-Interest Debt into Retirement
- OG and Joe stress that entering retirement with high-interest debt (credit cards, car loans, etc.) erodes financial stability and quality of life.
- OG:
“It destroys everything all the time... When you think about how much work you have to do to be able to afford all of the monthly payments that you have in your life… that’s not putting food on the table, that’s not having any fun. That’s not saving any money.” (11:00)
- Joe humorously contrasts the cautious optimism about S&P 500 returns with the ironclad guarantees of credit card interest rates:
“Credit card puts in writing 28.5—they are guaranteeing themselves 28.5 on you. And we’re like, ‘oh, back it down, back at that. Not 10 or 11.’” (14:01)
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Lacking a Tax Strategy for Withdrawals
- Many retirees underestimate the impact of not planning for taxes on withdrawals from various accounts (401(k), Roth, brokerage, etc.).
- OG:
“If you have only one bucket, you’re limited in your choices... The time to prepare for that is when you’re 30 or 40.” (15:03)
- Joe underscores the value of diversification across all three “tax triangle” corners: pre-tax, Roth, and taxable brokerage.
- He also reminds listeners about tax bracket management and “gotchas” like IRMAA and Social Security taxation (17:52).
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Treating a Home as the Retirement Plan
- The notion that selling or borrowing against a primary residence will fund retirement is deeply flawed and emotionally complicated.
- OG:
“Selling the family home to fund your retirement is a little bit more mentally painful than people think it is... it sounds like a great idea until you have to execute it.” (19:35)
-
Not Planning for Longevity Risk
- Many underestimate how long they’ll live—and how much money they’ll need.
- Nationwide Retirement Institute data: For a 65-year-old, a 50% chance to reach age 85 (male) or 88 (female), and a 25% chance to reach 91 (male) or 93 (female).
- OG:
“This is why, from a planning standpoint, we use 100 as kind of a baseline... You can’t prove to me that 100 is an unrealistic number.” (22:06)
- The hosts debate the tradeoff between “conservative” planning horizons and missing out on spending/experiences (24:39).
- Delaying Social Security, considering longevity insurance, keeping portfolios growth-oriented, and planning for long-term care are offered as solutions.
Notable Quotes & Moments
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On Clickbait Headlines:
Joe:“The headline says the number one habit, and they proceed to give us five. That’s when you know there was no communication between whoever wrote the title.” (09:46)
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On Credit Card Debt:
Joe:“We happily sign up for more and go, ‘oh, it’s not that big a deal.’” (14:31)
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On Taxes & Withdrawals:
OG:“Everybody thinks it’s fun when Willie’s all nilly with everything, but then when you do it with your withdrawals, it’s not so great.” (14:53)
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On Longevity & Planning:
OG:“If you’re too conservative in your planning, you’re going to underspend throughout your entire retirement life and not do stuff.” (23:14)
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On Industry Norms for Life Expectancy:
OG:“I think 100 is the minimum. Honestly, I think 110 or 120 is probably a good number also.” (25:17)
Key Insights and Practical Tips
-
Tackle Debt Aggressively Before Retiring:
Prioritize eliminating high-interest debt—every dollar spent on interest is a dollar not enjoyed in retirement. -
Diversify Retirement Account Types:
Build flexibility by contributing to pre-tax, Roth, and taxable accounts; this opens up tax strategies during withdrawal years. -
Have a Distribution Tax Plan:
Annually evaluate withdrawal sources to optimize for taxes and minimize pitfalls like IRMAA surcharges or surprise taxation on Social Security. -
Don’t Rely on Home Equity Alone:
Treat the value of your primary residence as a backup, not the main act, in your retirement income planning. -
Plan for a Long Life, but Balance Enjoyment:
Use a higher-than-average age for projections (planning to 100+), but revisit annually to balance against underspending and missed adventures.
Quick Segments & Listener Engagement
TikTok/YouTube Minute: “Four ETFs to Hold Forever”
(Begins at ~34:53)
- Social media video recommends: VTI (total US market), VOO (S&P 500), QQQ (NASDAQ/tech), IBIT (bitcoin ETF).
- The hosts challenge the redundancy between VTI, VOO, and QQQ, suggesting it’s akin to “having a peach pie and some peach cobbler.” OG calls for real diversification, like small caps and international, not simply large US stocks and bitcoin.
- OG’s “digital gold” comparison:
“Gold has returned about 4.4x since 1980. Stocks are up 51x since 1980. Which one is a better hedge for inflation?” (38:17)
Second Opinion: Do Stock Splits Trigger Taxes?
(Begins at ~39:19)
- Listener asks if a split (e.g., 10-for-1) means a tax bill.
- OG:
“No, that doesn’t have any effect. Your cost basis is adjusted equally... At the end of the day when you get a stock split, that doesn’t do anything to anything. That’s just a big non event.” (41:05)
Community Corner
(Back porch segment, ~44:24)
- Shout-out to Stacker Janelle for repping Stacking Benjamins at a CampFI event in her SB t-shirt.
- Listener Falcon Horowitz wins the Internet with his “chicken broth” dad joke (“Is that where chickens save their post-tax retirement money?”), followed by a playful post from Philip on “nest egg” origins.
- Encouragement for listeners to submit their own stories or wear SB swag in the wild.
Memorable Exchanges
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On Home Equity in Retirement:
OG details the psychological struggle of selling a beloved family home, even after years of touting it as a “plan,” providing a relatable, human side to the financial calculation (18:26-20:23). -
On Life Expectancy:
Doug muses on not wanting to live to 100, while OG jokes about aiming for 140 to “see my kids turn 100”—a moment of levity highlighting the unpredictability of planning for longevity (20:31-20:44).
Timestamps
| Segment | Timestamp | |-----------------------------------------------------|-------------| | Banter & Episode Introduction | 01:13-04:01 | | Main Headline Begins | 09:09 | | High-Interest Debt in Retirement | 11:00 | | Tax Strategy for Withdrawals | 14:47 | | Using Home as a Retirement Plan | 18:05 | | Longevity Risk & Life Expectancy Planning | 20:23-26:18 | | Host opinions on Stock Splits & Taxes | 39:19 | | ETF Critique (TikTok/YouTube Minute) | 34:53-39:12 | | Listener Community / CampFI Shoutouts & Fun Banter | 44:24 |
Final Takeaways
- Don’t get distracted by clickbait. The title may scream “number one habit,” but real retirement risk is multi-faceted.
- Be proactive—eliminate high-interest debt, diversify your account types, plan for taxes, and assume a long, active retirement.
- Stay flexible and revisit your plan annually to balance security with enjoying your hard-earned savings.
- Stack Benjamins with a sense of humor.
For full resources and links referenced, visit stackingbenjamins.com.
This summary covers only the primary discussion and knowledge sections. For the trivia, pop culture reviews, and signature end-of-episode humor, listen to the full episode!