Podcast Summary: "Love It or Leave It: Financial Edition"

The Stacking Benjamins Show (SB1803)
February 13, 2026
Host: Joe Saul-Sehy with OG, Paula Pant, Jesse Kramer, and Doug

Overview

To kick off Valentine’s Day weekend with their signature blend of fun and function, the Stacking Benjamins crew tackles big financial concepts in a “Love It or Leave It” roundtable. Each panelist must respond to provocative personal finance statements—either loving them, leaving them, or sharing nuanced takes. The aim: spotlight the emotional-versus-logical divide in money decisions, challenge popular tropes, and have a few laughs along the way. The show also includes playful competition through their ongoing trivia battle and listener interaction via live YouTube chat.

Key Discussion Points & Insights

1. Emotional Decisions in Paying Off Low-Interest Mortgages

Prompt: "Paying off a low-interest mortgage early is an emotional decision pretending to be a financial one. Love it or leave it?"

• Paula Pant: Loves it. Points out how most decisions to pay off low-interest mortgages are rooted in emotion—security and peace of mind—especially where income is unstable (entrepreneurs vs. tenured professors). Notes that emotional, non-mathematical decisions are sometimes justified for individual peace of mind. (07:57)

  “It is an emotional decision. Although there's nuance.” (08:18, Paula)

• Jesse Kramer: Loves it, too; stresses that the spreadsheet might not always align with personal comfort but feeling good is a value in itself. (09:07)
• OG: Leaves it. Argues that all debt—even “good debt”—imposes ongoing pressure and risk. The goal should be to remove those obligations, not just stick to math. (10:06)

  “Debt is awful. Even good debt sucks. It just sucks less.” (10:13, OG)

2. FIRE Movement: Financial Independence vs. Retiring Early

Prompt: "Most people chasing FIRE don’t want to retire early—they just hate their jobs. Love it or leave it?"

• Jesse Kramer, Paula Pant, OG, & Joe: All love it. They note that many pursuing FIRE actually want flexibility for a meaningful career change or sabbatical, not a life of no work. FIRE is more about “financial independence” than actually “retiring early.” (12:14–15:51)

  “They want a well-funded career change...retirement in their definition is not the cessation of income.” (13:06, Paula)

3. Lifestyle Inflation: Moral Failure or Natural Progression?

Prompt: "Lifestyle inflation isn’t a moral failure—it’s the point of making more money. Love it or leave it?"

• OG: Leaves the moral judgment at the door—do what aligns with your values and don’t feel the need to justify it. (17:53)

  “You don't owe anybody an explanation for how you spend your money other than the people that are immediately impacted.” (19:48, OG)

• Paula Pant: Leaves it. It’s not a moral failing NOT to inflate your lifestyle either. Frugality is a choice, and so is spending—both can be correct. (22:05)
• Jesse Kramer: Leaves it. Some inflation is okay, but letting lifestyle rise lockstep with income is a problem financially—even if not morally. (23:45–24:36)

4. Real Estate: Passive Income or Not?

Prompt: "Real estate is only passive income if you ignore the stress, time, and risk. Love it or leave it?"

• Paula Pant: Leaves it. The real issue is with defining “passive income” as “free money.” Real estate earns “passive” status for tax purposes, but not as slang for effortless income. (36:37–38:06)
• Jesse Kramer: Loves it. Real estate, especially hands-on, is much more active than diversified investing. “Passive” is a misnomer except for very hands-off investors. (38:12–39:20)
• OG: Sides with Paula, leans toward leave it. All investing requires attention, but the amount varies. It’s about building the right systems. (39:26–41:43)

5. The (Now) 4.7% or 5.25% Withdrawal Rule: Rule or Blanket?

Prompt: “The 5.25% rule is less of a rule and more of a financial security blanket. Love it or leave it?”

• Jesse Kramer: Loves it. These rules are ultra-conservative starting points. Reality is more flexible and needs situation-specific analysis. (42:18–43:35)

  “It is that financial security blanket that makes you say, ‘Well, at least I know I’m skewing so far conservative…’” (42:42, Jesse)

• OG: Agrees it's a security blanket. The rule gives peace of mind, but real markets and retirements are rarely average. Don't underspend due to rules meant for worst-case scenarios. (43:55–45:31)
• Paula Pant: Also in the “security blanket” camp. Notes that mandatory foundation spend rates are actually higher (5%)—real-life outcomes can be significantly better than rules suggest. (45:38–47:41)

6. Do Budgeting Apps Actually Help?

Prompt: “Budgeting apps don’t fix spending problems; they just document them in prettier colors. Love it or leave it?”

• OG: Leaves it. If you measure it, you notice inefficiencies and are naturally prompted to change. Seeing spend pain points (like DoorDash) inspires real action. (49:20–50:57)
• Paula Pant: Leaves it. Budgeting is like calorie-counting: too tedious long-term, but powerful in short sprints as a diagnostic tool. (51:36–52:33)

  “It's carrying a food scale and eating everything out of a measuring cup. It's not realistic for the long term...but doing it in a sprint will give you information. And you can't help but change your behavior once you have that information.” (51:36, Paula)

• Jesse Kramer: Leaves it. Measuring spending inevitably leads to managing it (“What gets measured changes”). (52:56–54:44)

Notable Quotes & Memorable Moments

• OG (on debt): “Debt is awful. Even good debt sucks. It just sucks less.” (10:13)
• Jesse (on budgeting): “That which gets measured gets managed.” (53:50)
• Paula (on budgeting): “I've often thought of budgeting as the calorie counting of personal finance.” (51:36)
• Paula (on career changes): “You want a well-funded career transition…pay off your mortgage first.” (13:32)
• Joe (on withdrawal rules): “You get to 82 and you live a normal ... life and you got money left and you left some life on the table.” (45:31)
• OG (on lifestyle inflation): “You are the only arbiter of your own value system.” (19:54)

Fun & Trivia: The Panel's Competition

• [25:13] OG triggers a “margin call” against Jesse in a winner-takes-points trivia round.
• [34:52] OG wins the trivia, keeping his commanding lead with the correct answer on how many people plan to stay home for Valentine’s Day (46%).
• Humorous banter about romantic plans, Valentine’s Day, and the relative desirability of Toledo and dermatologists’ houses runs throughout the episode.

Memorable Segments & Timestamps

• Start of “Love It or Leave It” segment: (07:25)
• Paying off low-interest mortgages: (07:25–11:45)
• FIRE Movement motivations: (12:14–16:43)
• Lifestyle inflation discussion: (17:53–24:36)
• Trivia battle and “margin call”: (25:13–35:36)
• Real estate as passive income: (36:37–41:43)
• Withdrawal rate rules: (42:18–48:38)
• Budgeting apps debate: (49:20–54:44)

Tone and Closing

The show maintains its breezy, banter-filled, yet smart tone. Financial topics are explored with humor, humility, and a keen awareness that money decisions are personal, values-driven, and often more emotional than “experts” let on.

Takeaways

• Most big financial decisions blend emotion and reason—and that's okay.
• FIRE is as much about freedom and meaning as money.
• Lifestyle inflation (or not) is only right or wrong if you deviate from your own values.
• So-called “rules” (mortgage, withdrawal, budgeting) are only helpful if they fit you.
• Measuring (but not obsessing over) your money changes behavior for the better.

For more discussion or to share your own “Love It or Leave It” takes, check out the Stacking Benjamins Facebook group.