The Stacking Benjamins Show – Episode SB1742

5 Steps to Your Best Retirement (with Jeremy Keil, CFP)
Date: October 1, 2025
Host: Joe Saul-Sehy, co-host OG
Guest: Jeremy Keil, CFP, host of Retire Today Podcast

Episode Overview

This episode dives into retirement planning using a practical, five-step framework developed by CFP Jeremy Keil. With their trademark lighthearted banter, Joe, OG, and Jeremy explore why most people start their retirement planning backwards—and how shifting your perspective can create a more secure, flexible, and enjoyable future. They also tackle timely headlines like the partnership between T. Rowe Price and Goldman Sachs for new 401(k) offerings, with a critical look at alternative investments in retirement accounts.

Main Theme

How to Build Your Best Retirement Using Five Simple Steps
Jeremy Keil lays out a clear, actionable process for taking control of your retirement future, starting with understanding your true spending needs and layering in investment and tax strategies only after crafting a thoughtful framework. The hosts use real stories, practical advice, and humor to make sense of the retirement puzzle—and caution listeners to beware of financial "opportunities" that benefit big institutions more than individuals.

Key Discussion Points and Insights

1. Retire Today: Why Start Planning Now?

(08:44 – 10:49)

• Jeremy asserts that "Retire Today" means taking control now, regardless of your age—whether you're 35 or closing in on retirement.
• He shares a story about a client who felt forced into a higher-paying, less satisfying job for her retirement's sake, but after planning, realized she could keep her preferred job and delay retirement joyfully.

Quote:
"It's all about taking control of our retirement today."
— Jeremy Keil (08:44)

• Both hosts and Jeremy decry how people spend more time planning vacations than retirement—emphasizing the importance of dreaming and intentionality in the process.

2. The Five Steps to Retirement Planning

Step 1: Spend — Know What You’re Solving For

(11:21 – 12:13, 17:22 – 18:42)

• Jeremy surprises Joe by putting "spend" first, not "invest."
• The key question: How much do you want (or can afford) to spend each year in retirement?
• Calculating this informs everything else.
• Jeremy recommends starting with “your retirement longevity number”, not just life expectancy.

Quote:
"What are you solving for? Are you solving for a million bucks? No, you’re solving for how much money do you need coming into your checking account."
— Jeremy Keil (11:22)

• He recommends tools like longevityillustrator.org to estimate how long retirement could last.

Memorable Moment:

• Most people retire three years earlier than expected. Health, forced layoffs, or Social Security temptations play a role. Plan for retirement to start sooner than you think.
  (14:11)

Step 2: Make — Identify Your Income Streams

(18:52 – 25:21)

• Social Security is a near-universal income source, with some also having pensions.
• Jeremy emphasizes making thoughtful, math-driven decisions (not relying on anecdotes or myths), especially regarding Social Security claiming strategies:

Quote:
"Do math-based Retirement planning, don’t do myth-based retirement planning."
— Jeremy Keil (19:46)

• He warns couples can lose out on up to $180,000 by making poor Social Security decisions (20:00), and again recommends using tools to calculate actual odds of living past certain break-even ages.

• On pensions: Don't just compare "take it now" vs. "take it next year"—review all options and beware of advisor incentives to roll over lump sums.

Quote:
"If you can check a box and make it worth more or worth less, I'm guessing you'd rather take a few minutes, do the math, and check the right box to give you fifty, a hundred grand more."
— Jeremy Keil (24:03)

Step 3: Keep — Minimizing Taxes

(28:13 – 33:16)

• Retirement can give you more tax flexibility than working life—choose where and when to draw your income.
• Tax diversification—having money in Roth, traditional, brokerage accounts—creates more control in retirement.

Quote:
"What most people don't realize is you hit retirement, you have far more control over your tax situation than you did beforehand."
— Jeremy Keil (28:17)

• For younger savers: Jeremy's bias is toward Roth accounts when possible.
• Beware Medicare surcharges and ACA subsidy cliffs—good planning is more than just staying in a particular tax bracket.

Step 4: Invest — The Time Is Not Always Now

(33:27 – 39:41)

• Investing is the fourth—not the first—step. Only after knowing your needs and sources do you design your portfolio.
• Jeremy shares a cautionary tale: “Gary,” a client who panicked in 2009 and cashed out at the market bottom, locking in losses, even though he didn’t need the money immediately.

Quote:
"If you need money short-term, use short-term investments; if you need money long-term, use long-term investments. It's all about your time horizons."
— Jeremy Keil (36:29)

Memorable Moment:

• Joe recalls his own experience with family members making emotional decisions—reinforcing that having a spending plan keeps investing rational.

Step 5: Leave — Planning for What Remains

(39:26 – 43:02)

• Don’t forget legacy planning, but also disaster planning: What if you live much longer? What if a health crisis hits?
• Planning is not just about documents, but also thinking through worst-case scenarios—like long-term care—regardless of whether you buy insurance.

Quote:
"It's not just the idea of the estate planning and how much money you're gonna leave behind. It's also what are the risks that could derail your retirement?"
— Jeremy Keil (39:27)

Memorable Moment:

• Joe observes, “Watching a plan spring into action…was always so—fun’s not the right word—comforting.”

Notable Quotes & Moments with Timestamps

• On the futility of trying to predict the market:
  "This is an ongoing thing where you should figure out ahead of time what is it you might be spending in retirement. But then every year, take a look, 'What did I spend? What am I planning to spend next year?' You got a course-correct along the way." — Jeremy Keil (16:16)

• On unnecessary focus on the 4% rule:
  "If you’re trying to get 99% certainty you’ll have enough, what that really means is 99% of the time you didn’t spend enough, you could have spent more."
  — Jeremy Keil (18:18)

• On the illusion of certainty in retirement:
  “A lot of people think like I'm hitting this exact number and that's it. Well, what if it's five? What if it's 35? Think of those different things that could change your retirement.” — Jeremy Keil (40:26)

• On long-term care:
  "Doesn't mean you have long-term care insurance, just means you have a long-term care plan."
  — Jeremy Keil (41:52)

Headline Segment: Private Investments in Your 401(k)

(53:11 – 63:26)

• News: T. Rowe Price and Goldman Sachs planning to market alternative/private investments to 401(k) plan participants.
• Hosts’ Hot Take:
  • These products exist to benefit the firms, not you.
  • Alternative Investments: Often illiquid, complex, with high fees, inappropriate for the average retirement investor.
  • OG: Points out the risk/reward trade-off: “Would you risk $30,000 for the possibility of an extra $4,500 when it could go to zero?” (61:41)
  • Joe: “Disregard the sales pitch—at least look behind it. These are compelling stories, but inside your 401k…yuck.”

Conclusion:

• Stick with broadly diversified, liquid investments in your 401k; treat private alternatives as play money at best.
• They expect to see cautionary tales in coming years as people chase risky, illiquid “opportunities.”

Other Highlights & Memorable Moments

• Joe’s Reflection on Jonathan Clements (Obituary, 64:29 – 66:57):
  • Praises Clements’ clarity and his focus on savoring life experiences.
  • Recalls discovering the value of planning well in advance—as with travel—for maximum enjoyment.

Important Timestamps

| Segment | Timestamp | |---------------------------------|:-------------:| | Podcast intro and banter | 01:19–07:42 | | Main interview: Retirement steps| 07:42–44:27 | | Notable Quotes and Stories | throughout | | Headline: Private investments | 53:11–63:26 | | OG’s practical spending buckets | 49:23–50:07 | | Community & Jonathan Clements | 64:29–66:57 | | Takeaways and close | 67:48–end |

Actionable Takeaways (from Doug’s Wrap-up)

1. Start with spending, not investing—Once you know what you want to spend, everything else falls into place.
2. Skeptical of private assets in retirement accounts—They enrich big banks, not you.
3. Have a plan for long-term care and legacy, insurance or not—The key is having intentionality.

Resources and Links

• Jeremy Keil’s book: Retire Today: Create Your Retirement Master Plan in 5 Simple Steps
• Jeremy’s website: jeremykeil.com
• Longevity Illustrator: longevityillustrator.org
• Retire Today Podcast: linked in show notes

This episode offers a humorous but incisive take on the realities of retirement planning—emphasizing simplicity, intentionality, and skepticism of Wall Street’s latest pitch.

Notable Quotes Recap (Speaker | Timestamp):

• Jeremy: “Retire today…is all about taking control of our retirement today.” (08:44)
• Joe: “It’s much easier to create a retirement plan when you start with spending, not investments.” (49:23)
• OG: “You have to look at the fees. You have to look at the liquidity event. When will this [private investment] ever be sold?” (58:19)

For detailed show notes and links, visit: stackingbenjamins.com