The Stacking Benjamins Show

Episode SB1746: Build a Confident Early Retirement Plan (Without Overthinking It)

Release Date: October 10, 2025

Episode Theme & Purpose

This episode of The Stacking Benjamins Show focuses on demystifying early retirement planning. Hosts Joe Saul-Sehy and OG, along with panelists Paula Pant (Afford Anything podcast) and special guest Sean Mullaney (co-author of Tax Planning To and Through Early Retirement), offer a comprehensive, approachable discussion on crafting an early retirement plan without getting stuck in overanalysis. The panel explores definitions, common misconceptions, financial levers, tax considerations, asset allocation, lifestyle choices, and actionable strategies—mixing practical expertise with the show’s trademark humor and relatability.

Key Discussion Points & Insights

1. Defining "Early Retirement"

[10:30–15:20]

• Avoiding Semantics: The panel sidesteps tired debates about what “retirement” truly means, instead aiming for clarity and common ground.
• Paula Pant’s Take: "Retirement is not the complete and permanent cessation of all income producing activity. ... A 65-year-old retiree often volunteers or works part time—they have options. Early retirement just brings those options forward." ([11:04])
• OG’s View: Early retirement mainly means stopping your primary job before age 62/65, regardless of supplementing with part-time gigs.
• Sean Mullaney’s Perspective: "If you retire prior to Medicare enrollment ... you've got a health insurance issue to manage. ... Anyone before 65 is early by at least some planning metric." ([12:42])
  Sean suggests that everyone needs to consider early retirement possibilities, even if they don’t plan on it, due to career unpredictability and forces like AI.

2. The Three Levers: Saving, Spending, Earning

[15:20–21:59]

• Sean’s Priority: Both saving/investing (building wealth) and spending (managing expenses) are critical; spending exerts substantial influence over retirement viability.
• Paula's Framework: Savings rate is #1 (“increasing the delta between what you earn and what you spend is the backbone of everything”), investing is #2, asset allocation is #3. ([16:50])
• OG’s Reality Check: Many people either save too little or, conversely, save too much and don't enjoy life (two sides of the same psychological coin).
  "You can only cut so much spending ... there’s no theoretical limit to your income." ([20:23])

3. Lifestyle Design and Opportunity Cost

[21:59–24:01]

• Intentionality: Each panelist agrees that early retirement success hinges on being deliberate about what you prioritize spending on.
• Paula’s Signature Insight:
  "You can afford anything, just not everything ... the goal is to be intentional about what you say yes and no to." ([21:59])
• Sean on Tax & Lifestyle: Spending more on "stuff" in retirement not only increases consumption but can raise taxes when withdrawing from retirement accounts. "Stuff ends up in the landfill, while experiences don’t create a burden for loved ones." ([24:01])

4. Tax Planning for Early Retirement

[26:11–28:20]

• Asset Location: It’s vital to be thoughtful about where different types of investments sit (traditional/Roth/taxable accounts) for maximizing tax efficiency.
• On "Ideal Ratios": Sean pushes back on the search for a perfect mix, focusing instead on flexibility and intentional drawdown. "With any decent mix of accounts, you can probably have a very tax-efficient retirement with some planning."

5. The Roth vs. Traditional Retirement Account Debate

[28:20–38:05]

• Sean’s Traditional Lean: "Let's pay tax when we pay less tax. For most Americans, working years are highest tax years, so deferring with traditional accounts saves more." ([28:52])
• Paula’s Roth Bias: She champions Roth, especially for younger savers, for:
  1. Maximizing tax-free growth ("...that money is going to double... the amount you are eventually pulling out grows to 300%, 400%, 500% more than what you have put in"),
  2. Tax rate uncertainty ("...there's at least a probability tax rates might be much higher in the future"),
  3. Simplicity ("What you see is what you get in your portfolio balance.") ([34:13])
• OG’s Flexibility Stance: "Yes to everything. Build all account types; the real benefit is flexibility to optimize withdrawal strategies year by year."

6. Asset Allocation for Multi-Decade Retirement

[51:37–55:13]

• Key Insight (OG): "I don’t think your portfolio changes much whether you retire at 50, 55, or 65. If you’ve got sufficient assets, why would you suddenly go ultra-conservative?"
• Paula’s Support: Early retirees face a bigger risk being too conservative than too aggressive. She endorses a bucket strategy—segment assets by time horizon and purpose.
• Sean on Drawdown: The drawdown phase requires more attention for early retirees; order of withdrawals is crucial but manageable with intention.

7. Tax Strategies & Utilizing Non-Retirement Accounts

[55:13–61:29]

• Sean: If you retire long before 65, having taxable brokerage accounts is hugely helpful for both tax flexibility and managing healthcare (ACA premium subsidies).
• Managing Withdrawals: For early retirees, using “basis recovery” from taxable accounts keeps AGI low, increasing ACA credits and potentially hitting 0% capital gains rates.
• On IRS §72(t): Recent changes make this a more viable option for early withdrawals, especially after exhausting taxable accounts.

8. Future-Proofing Your Early Retirement Plan

[62:49–65:18]

• OG: "Spend 95% of your energy on figuring out your savings goal; 5% on optimization. You won't regret having too much, but you might regret falling short." ([62:49])
• Paula: Prepare for black swan events: major health crises, lawsuits, cognitive decline, etc. ("Protection and playing defense is key.") ([63:56])
• Sean: Max out retirement accounts for wealth-building and creditor protection ("Creditor protection is an underappreciated benefit of IRAs and 401(k)s.") ([64:37])

Notable Quotes & Memorable Moments

• Paula Pant ([21:59]):

  "You can afford anything, just not everything."

• Sean Mullaney ([14:15]):

  "...in today's world, everyone needs the early retirement playset in their playbook. Not everyone needs to plan on early retirement, but you need flexibility."

• OG ([38:05]):

  "If you’re trying to tweak that last 5% of the calculation, you’ve already won the game."

• Joe Saul-Sehy ([65:18]):

  "It truly is, if you look at Benjamin’s life, about stacking more life, not just more dollars."

Humorous Banter:

• The lively "caddy corner vs. kitty corner" debate. ([03:23–04:15])
• Paula’s attempt to calculate distances during her move—"It's almost a mile. It's 0.8 miles." ([05:43])
• Multiple pop culture references—from The Art of War and Princess Bride to Van Halen and SNL’s Church Lady.

Timestamps for Important Segments

• Opening and Introduction: [01:33–10:30]
• Defining Early Retirement: [10:30–15:20]
• The Three Financial Levers: [15:20–21:59]
• Lifestyle Design & Opportunity Cost: [21:59–24:01]
• Tax Location and Drawdown Strategy: [26:11–28:20]
• Roth vs. Traditional Debate: [28:20–38:05]
• Trivia Interlude: [39:47–49:19]
• Key Differences for Long Early Retirement: [50:36–55:13]
• Asset Allocation for Multi-Decade Retirement: [51:37–55:13]
• Tax Planning & Withdrawal Tactics (incl. 72t): [55:13–61:29]
• Strategies for Future-Proofing Your Plan: [62:49–65:18]
• Wrap Up, Panel Updates, and Book Details: [65:18–69:32]
• Doug’s Three Takeaways: [69:32–70:20]
• Show Credits and Outtakes: [70:20–74:49]

Actionable Takeaways

• Define Retirement Flexibly: Don’t get bogged down—focus on creating financial options for yourself, not a hard stop on work.
• Dial in Savings Rate: The savings 'gap' is paramount; savings and spending choices have long-term ripple effects.
• Leverage Tax Flexibility: Build balances across traditional, Roth, and taxable accounts to maximize drawdown options and manage taxes.
• Don’t Over-Optimize: Nail the big 'how much' goals—minor allocation tweaks matter less once you’re saving enough.
• Plan for Healthcare Before 65: ACA strategies and taxable accounts are powerful for bridging the pre-Medicare gap.
• Invest for the Long Haul: Early retirees can’t afford to be too conservative—bucketing and maintaining growth assets is critical.
• Prepare for Life’s Unknowns: Protect against lawsuits, health disasters, and cognitive decline with insurance and account protections.

Resources Mentioned

• Sean Mullaney & Cody Garrett’s book: Tax Planning To and Through Early Retirement (available via major booksellers, and linked in show notes).
• Paula Pant’s Afford Anything Podcast: For deeper dives into lifestyle design, personal finance, and investing.

Final Thoughts

This episode provides both practical frameworks and nuanced debate, equipping listeners to build confident early retirement plans that are flexible, intentional, and robust—without falling into the trap of overthinking. The expert panel offers reassurance that, while the financial landscape may shift, the timeless principles of saving, intentional spending, and strategic investing will always provide a solid foundation.

For more resources, links, and panelist info, see the show notes at stackingbenjamins.com.