The Stacking Benjamins Show – Episode SB1743

"The Missing Ingredients From Many Financial Plans"

Original Air Date: October 3, 2025
Panelists: Joe Saul-Sehy (host), OG (co-host), Paula Pant, Jesse Kramer, Doug (Joe's mom’s neighbor)
Theme: Unpacking the Three Most Commonly Missing Elements in Financial Plans (based on an article by Evan Beach, CFP, in Kiplinger)

Episode Overview

In this lively and humorous roundtable, Joe, OG, Paula, and Jesse dig into a Kiplinger article identifying three things most financial plans are missing. The crew discusses why financial plans often fall short, the pitfalls of focusing only on charts and investments, and how essential overlooked areas like tax/estate planning and clear action steps can make or break your finances. They share personal anecdotes, audience insights, and actionable advice for listeners, all in their signature “fun in a basement” style.

Key Discussion Points & Insights

1. The Problem with Most Financial Plans: All Charts, No Action ([08:17])

• The Kiplinger article notes many plans are just charts, graphs, and probabilities without actionable steps.
• OG: “Substituting portfolio for planning is a very common, easy thing for an advisor to do... but the real benefit is having the conversations about what’s upcoming in your life.” ([09:27])
• Paula: Warns of an “overfocus on the what (investments, tactics), and not on the why,” causing people to lose the big picture ([11:12]).
• Joe: Highlights that people are often more comfortable talking investments over goals: “People thought it was cotton candy... let's get to the hard stuff.” ([13:02])
• Jesse: Advises boiling complex, long-term plans into “simple nuts-and-bolts logistics for the next six months,” noting planners and clients alike often get caught “thinking decades ahead but forgetting what has to happen tomorrow.” ([13:35])
• Action Point: Demand a “do-this-then-that” roadmap in your financial plan—not just projections.

2. Missing Ingredient #1: Tangible, Step-by-Step Plans ([14:50])

• OG: “Absent something more important, the default is investments and headlines. It’s our job to stay focused on what has the biggest impact.” ([15:10])
• Planners need to bring clients back to actionable steps, not just market chatter.
• OG: “I'd rather spend 28 minutes having you tell me about your trips and 2 minutes discussing tiny tweaks.” ([17:40])
• Key Insight: Financial planning should allocate time to real life goals, with only minimal focus on tinkering with portfolios.

3. Missing Ingredient #2: Tax & Estate Planning ([18:29])

• Evan's article laments the neglect of tax and estate strategies—which can pay bigger dividends than portfolio tweaks.

Making Estate Planning Less Scary ([19:27])

• Jesse (on making estate planning relatable): "It's like, okay, let's be realistic. We all die... but there are too many stories where someone leaves a mess. A simple estate plan solves so many problems." ([19:32])
• Doug (joking): “We’re putting the fun in funeral.” ([20:50])
• Paula: Suggests normalizing estate planning as a standard milestone, like turning 18 or getting a colonoscopy, “making it a rule” so there’s less subjectivity and avoidance. ([21:59])

Importance of Tax Planning ([23:55])

• OG: "Every single solitary thing has a tax impact... nobody likes surprises, good ones or bad ones, especially tax ones in April." ([23:55])
• If your only tax preparation is dropping papers at your CPA in April, your plan is missing a critical piece.
• Tax planning should consider not just this year but domino effects, like Medicare premium surcharges due to income ([25:23]).

4. Missing Ingredient #3: Clear Answers to Big Questions ([40:31])

• Plans often avoid direct responses to key questions like “Can I retire?” resorting to vague probabilities instead.
• Paula: “At the heart of it, the big question is: Will I be okay?” ([40:31])
• Jesse: Pushes back: "Most actual financial plans go straight into the big questions... What they're missing is often the step-by-step to get there." ([41:07])
• OG: Stresses balancing realism and optimism. “We have to provide hope and optimism in as much dosage as the realistic numbers.” ([43:16])
• On delivering tough messages: “If you say to someone, ‘You’re good, man, you can’t even screw this up,’ they might try.” ([43:44])
• On handling clients who fall short: “If 60 isn’t happening, maybe 62 is, if you do these three things. Here’s the path to get as close as possible.” ([44:57])

Notable Quotes & Memorable Moments

• OG ([09:27]): “Substituting portfolio for planning is a very common, easy thing for an advisor to do. The real benefit... is the actual work of planning, not just playing with small caps and interest rates.”
• Paula ([13:02]): “Goal-based planning is much more subjective...people are worried about crossing the line into Kumbaya, rainbows and unicorns.”
• Jesse ([19:32]): “You’re skydiving, your parachute breaks—don’t you wish you had an estate plan?”
• OG ([23:55]): “No surprises. I’m convinced nobody likes surprise—good ones, bad ones, especially tax ones... you should have a pretty good idea of what's happening with your tax situation.”
• Paula ([21:59]): “If you just make it a rule—when you turn this age, you get an estate plan—then it’s not personal, it’s just a rule.”
• Joe ([47:07]): “I like your emphasis on telling people not just ‘you can’t do this’ but also ‘here’s how we maybe get back to your goal.’”
• OG ([48:05]): “Well, you show up in the office: ‘Boy, you have a crapload of credit card debt! How are you even afloat?’... Like, I know, that's why I'm here. I need help, not more beating!”
• Paula ([50:28]): “With money, you need to establish expertise, because there are so many charlatans and salespeople out there. People's defenses are up, as they should be.”

Important Segment Timestamps

• [08:17] – Introduction of the missing elements in most financial plans
• [09:27] – OG explains why plans are all charts and no action
• [13:02] – Paula on avoidance of subjective goal-setting
• [13:35] – Jesse’s advice on breaking complex goals into actionable steps
• [17:40] – OG’s preferred use of client meeting time
• [19:27] – Jesse on making estate planning relatable and urgent
• [21:59] – Paula’s “make it a rule” for estate planning
• [23:55] – OG on the omnipresence and importance of tax planning
• [40:31] – Addressing the desire for clear, direct answers: “Will I be okay?”
• [41:07] – Jesse defends that many financial plans do answer the big questions—but often miss step-by-step instructions
• [44:57] – OG on mixing realism and optimism for clients who are “behind”
• [47:07] – OG on advisor bedside manner for delivering hard truths

Takeaways & Action Items

Panelist Recommendations:

• Jesse ([52:45]): “Double-check your estate planning documents and beneficiary designations. For most Stackers, this is the piece they’re missing.”
• Paula ([53:09]): “Think about the black swan and gray swan events—not just budgeting and investing, but the big risks and uncertainties that could derail your plan.”
• OG ([54:49]): “Understand how all the moving parts—taxes, investments, insurance, estate—impact each other. At a minimum, forecast what your tax bill will be next year.”

Episode’s Fun, Community & Trivia Highlights

• Classic Stacking Benjamins trivia face-off between Paula, OG, and Jesse ([29:07]).
• Audience comments highlighted live, showing real-time engagement and additional resources (e.g., legal plans at work for affordable estate documents, [27:10]).
• Banter between cohosts full of their usual dad jokes and self-deprecating humor (skydiving jokes, lasagna tax, and “putting the fun in funeral”).
• Signature closing: Doug recaps absurd (but tangentially appropriate) action steps in a tongue-in-cheek “to do list.”

Final Thoughts

This episode underscores that financial plans must go beyond asset allocation and portfolio projections. The most reliable and helpful plans are actionable, holistic, and account for overlooked (sometimes uncomfortable) topics. Listeners are reminded to:

• Demand concrete action items,
• Cover “unsexy” but vital topics like tax and estate planning,
• Work with advisors who give both clarity and hope, not just charts and fear.

If your financial plan doesn’t address these areas, it’s time to fill in the gaps!

Find more: StackingBenjamins.com
Links to Jesse Kramer's Personal Finance for Long-Term Investors Podcast & Paula Pant’s Afford Anything Podcast are provided in the show notes.