Podcast Summary: The Stacking Benjamins Show

Episode: What Retirees Wish They'd Known 10 Years Ago (SB1758)
Date: November 7, 2025
Hosts: Joe Saul-Sehi, OG (absent), Doug (Joe’s Mom’s neighbor)
Guests: Jesse Kramer (Personal Finance for Long Term Investors), Jill Sirianni (Frugal Friends Podcast), Dr. Jordan “Doc G” Grumman (Earn & Invest Podcast)
Theme: The top five retirement planning “regrets” as seen by professional financial planners—what retirees wish they’d done a decade earlier, with a blend of practical advice, personal anecdotes, and trademark humor.

Episode Overview

This lively roundtable episode dives into the five most common regrets retirees have about their retirement planning, according to financial planners. The hosts and guests break down these pitfalls, share personal stories, and offer actionable insights with Stacking Benjamins’ signature mix of friendly banter, relatable language, and practical wisdom. Along the way, Jill, Jesse, and Doc G share both professional expertise and personal experience, ensuring valuable takeaways for listeners of any age.

Key Discussion Points and Insights

1. Choosing the Wrong Investment Allocation

• [14:56] Doc G admits: Even seasoned planners can get it wrong. He describes how his wife’s surprise early retirement left them too aggressively invested in equities:

  "We were way too equities heavy. Our bond allocation was much lower than I probably would’ve wanted… Ideally, we would’ve had much more safe assets, things like bonds."

• [16:29] Jill’s struggle: She admits feeling more conservative, despite having decades before retirement, and highlights the confusion and fear many non-experts face.
  • Actionable Tip: Know your time horizon and risk tolerance. If unsure, seek a second opinion from a fee-only, fiduciary planner.
• [18:24] Jesse's observation: More often, people are too conservative, often leaving large sums in cash and bonds because “the idea of losing money scares me more than the idea of growing my money compels me.”
  • Memorable Quote [19:47]:
    “The idea of losing money scares me more than the idea of growing my money compels me.” – Jesse Kramer

2. Not Optimizing for Taxes in Retirement

• [23:28] Jill’s perspective: Recognizes that most are “so accustomed to a simple tax structure as W2 employees,” but retirement taxes are a very different world—each account is taxed differently and strategies are essential.
• [24:54] Doc G’s warning:

  “We let the tax tail wag the wealth dog too often… You can defer taxes, but you can’t escape them. Don’t spend decades worrying about tax optimization; get to the best 80%, hire the right people, then have some peace.”

  • HSAs (Health Savings Accounts) are cited as a rare clear tax win.
• [28:01] Jesse on unpredictability:

  "You plan based on today's assumptions. Financial planning is nothing more than making a set of assumptions… slowly realizing how wrong your assumptions are over time and adjusting."

  • Pragmatic Advice: Focus less on extremes (“Didn’t convert everything to Roth!”) and more on tax diversification – have pre-tax, Roth, and taxable resources for flexibility.
• [30:48] Doc G adds:

  "Tax status diversification is probably the best risk modification...That's probably the best risk modification for when you get to retirement."

3. Not Updating Your Estate Plan

• [44:01] Doc G underscores:

  “I can’t tell you how much stress people carry around for years because they haven’t updated their estate plan, and yet they don't do it...Basic estate planning is easy.”

  • Hire a lawyer, even if it’s just for peace of mind.
• [44:53] Jill confesses: Has life insurance but hasn’t updated the estate documents yet, echoing how common it is to delay.
• [46:20] Jesse’s pragmatic explanation:

  “You can probably get away without having a fully-fledged estate plan if you don’t have kids...but the state has an estate plan for you, and it might not be what you want."

  • Pro Tip: Once the main work is done, updates are easy—just revisit every 3-5 years, check beneficiaries, and add new accounts if needed.

4. Not Creating a Retirement Spending Plan (Budget)

• [49:27] Jill’s take:

  “Money is not going to be unlimited in retirement...if we've not become accustomed to living within certain spending parameters, it can be a huge adjustment.”

  • She connects budgeting to life transitions, routines, and ultimately, well-being.
• [51:13] Doc G’s insight:

  “You actually might spend more at the start of retirement...then slower from mid to late retirement. People who are nerdy like us may consider a higher withdrawal rate early and then pull back. It should be variable.”

• [53:07] Jesse on real-world planning:

  “Every good retirement plan starts with a conversation about dynamism… Life is dynamic.”

  • Key Takeaway: Don’t treat your retirement budget as a static number for decades—adjust it based on actual life events and needs.
• [55:39] Jill on Values-Based Spending:

  “It’s not just about looking at your cash flow, but examining the pieces… What do I feel really good about spending money on? Don’t start with deprivation. Be mindful and start with easy yes/no areas.”

5. Waiting Too Long to Spend Their Money (Over-Accumulating)

• [57:43] Doc G draws on his book ‘Taking Stock’:

  “Many people who listen to shows like this will probably die with excess money...It’s really hard to die with zero."

  • He stresses intentional spending on experiences and self-betterment over “things.”
• [59:28] Jill, from the ‘frugal’ side:

  “This is the frugal person’s problem...I’d rather keep [money] hoarded in my freezer than pull it out and use it.”

  • She recommends getting clarity on what is “enough” and intentionally using savings for meaningful pursuits.
• [63:41] Jesse notes:

  “If you find joy in a very frugal lifestyle, more power to you. But if you’re spending too much, are you sure you’re getting joy out of that extra spending?”

• [63:51] Doc G reveals a subtle regret:

  “It's not that people aren't spending enough; it’s that they’re accumulating too much… losing years of freedom working at jobs they don’t like, just to accumulate more.”

Notable Quotes & Memorable Moments

• On rules and flexibility in financial planning:
  “Only a Sith deals in absolutes. Dave Ramsey’s all about… no debt… But some people need that rigidity to get started.” (Jesse, [13:19])
• On over-complicating investing:
  “Having a ton of stuff just makes it worse. I've seen people with like 30 different things, and they come in asking, ‘What the hell am I doing?’” (Joe, [29:58])
• On the emotional benefits of estate planning:
  “Forget all the bad things that could happen. Just from the stress relief—feeling good about it—it’s totally worthwhile.” (Doc G, [44:48])
• Jill’s “values-based” budget:
  “Don’t start with deprivation… begin with the things that are easiest to cut. There’s a skill to knowing how to spend money well.” ([55:39])
• Doc G on oversaving:
  “They're accumulating too much. They lose years of freedom… instead of being home doing things they love, they're working at a job they don't like.” ([63:51])

Key Timestamps

• Start of main content/banter: [01:04]
• Beginning of discussion – retirement regrets: [09:59]
• Discussion of investment allocation regret: [14:56]
• Tax optimization discussion: [23:28]
• Estate planning, updating wills: [44:01]
• Retirement budgeting/spending regrets: [49:27]
• Regret: Not spending/over-accumulation: [57:43]

Tone and Style

• Friendly, approachable, and witty, with plenty of personal anecdotes, self-deprecating humor, and digressions.
• Hosts and guests regularly poke gentle fun at themselves, each other, and the seriousness of “expert” advice.
• Practical, non-judgmental, and highly relatable—clear that everyone, even professionals, makes mistakes.

Final Takeaway

Start early, stay flexible, and focus on what matters most to you—not on rules, but on your real needs, values, and goals.
The biggest regrets? Not getting started sooner, not asking for help when you need it, and not taking the time to define “enough.”
Remember: You can’t shrink your way to greatness. Spend intentionally, plan for flexibility, and don’t let perfectionism (or tax panic) rob you of a happy life.

Further Resources & Guest Plugs

• Jill Sirianni: Frugal Friends Podcast, “Buy What You Love Without Going Broke” (book), YouTube content
• Jesse Kramer: Personal Finance for Long Term Investors podcast and blog
• Doc G: Earn & Invest podcast, books including “Taking Stock”

"The real regret retirees have isn’t missing some magic bullet—it’s missing the chance to align their money with their life and values years earlier." — Stacking Benjamins Roundtable