5 Steps to Your Best Retirement (with Jeremy Keil, CFP) SB1742

14 snips

Oct 1, 2025

Jeremy Keil, a Certified Financial Planner and author/host of the Retire Today podcast, shares essential retirement planning insights. He emphasizes starting with your spending habits rather than investments to ensure success. Jeremy explains the emotional aspects of retirement and the importance of a robust tax strategy to maximize savings. The conversation also delves into the complexities of private equity in 401(k)s, cautioning listeners on potential risks. Packed with practical advice, this discussion lays the groundwork for a financially secure retirement.

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ADVICE

Begin With Spending Targets

Start retirement planning by calculating your spending, not by picking investments.
Know how much you need each year and how long you'll spend it to make all other decisions clearer.

INSIGHT

Plan For Longevity Uncertainty

Your retirement longevity number matters more than a vague life expectancy guess.
Use tools like longevityillustrator.org and plan for both shorter and longer outcomes.

ADVICE

Model Your Income Streams

Treat income sources (Social Security, pensions) as part of your plan and model their timing mathematically.
Run the math for couple strategies and avoid myth-based decisions about claiming ages.

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Think your retirement plan is bulletproof? Think again. In this eye-opening episode of The Stacking Benjamins Show, Joe Saul-Sehy, OG, and Neighbor Doug are joined by certified financial planner Jeremy Keil, CFP® to walk you through the steps to building a retirement plan that won’t crack under pressure. From mapping out your spending before you ever leave the workforce to crafting a tax strategy that keeps more money in your pocket, this conversation is your blueprint for making your golden years actually golden.

But just when you think you’ve got retirement handled, we throw a curveball: private equity. With giants like Goldman Sachs and T. Rowe Price trying to slip these complex investments into your 401(k), it’s time to ask whether “more opportunity” is really a good thing — or a trap for the unprepared. Joe and OG break down the risks, the realities, and what you need to know before you sign on the dotted line.

As always, we serve it all with a side of basement banter — from Doug’s trivia about the first issue of Playboy to a TikTok football moment you didn’t know you needed — plus real-life stories that prove retirement planning is as much about mindset as it is about math.

What You'll Learn In Today's Show:

The five key steps to building a retirement plan that works for you, not just a generic spreadsheet.
Why starting with your spending habits (not investments) can make or break your retirement success.
How to prepare for the emotional side of retirement — including those pesky “what now?” questions.
The surprising risks of private equity creeping into your 401(k) — and how to decide if it’s worth it.
Smart tax strategies to make your retirement money last longer.
How long-term care, market volatility, and unexpected expenses should factor into your plan.

Questions to Ponder During the Episode (and discuss with other Stackers!)

What’s one spending habit you need to understand now to avoid retirement surprises later?
How would you react if your employer added private equity options to your 401(k)?
Are you planning your retirement based on your lifestyle — or someone else’s idea of “enough”?

FULL SHOW NOTES: https://stackingbenjamins.com/five-steps-to-a-better-retirement-plan-with-jeremy-keil-1743

Deeper dives with curated links, topics, and discussions are in our newsletter, The 201, available at https://www.stackingbenjamins.com/201

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