Episode Summary: What 2025 Taught Us About Money (And What Actually Matters for 2026) – SB1776

Podcast: The Stacking Benjamins Show
Host(s): Joe Saul-Sehy ("Joe"), OG
Roundtable Contributors: Paula Pant (Afford Anything), Jesse Kramer (Personal Finance for Long-term Investors)
Date: December 19, 2025

Overview

In this year-end roundtable, the Stacking Benjamins team gathers in Joe's mom’s basement to review 2025's biggest money lessons and discuss what actually matters for 2026. Through their signature blend of humor and actionable advice, Joe, OG, Paula, and Jesse reflect on global trends (like AI) as well as personal developments, challenging listeners to embrace change, stay diversified, and not lose sight of what truly counts.

Key Discussion Points & Insights

1. AI’s Big Leap and It's Effect on Jobs and Life

• AI and the Workforce
  • Paula highlights the expansion of AI into more jobs than was anticipated, emphasizing the importance of “diversifying your skill set at work and prioritizing the human connection—things that AI cannot replicate” (08:47).
  • OG and Jesse agree: AI brings both fear and excitement, but advancements have always disrupted industries. The lesson? Adapt and focus on human-only strengths.
  • OG quips, “I don’t have any fear of AI except for the downfall of all mankind and just about everything everywhere. So other than that, I think it’s going to be okay.” (10:41)
• AI’s Limits and ‘Hallucinations’
  • The group warns about relying on LLMs for legal, medical, or financial advice as AI can confidently give wrong answers (“hallucinate”).
  • Paula jokes: “AI can sometimes give outputs that seem so confident and seem so well formed that you forget that it might be hallucinating.” (14:38)
  • OG shares an anecdote about AI giving outdated info: “It’s an unreliable narrator who has hallucinations that’s been in a coma for 12 months.” (16:16)
  • Joe notes the “jagged edge” of AI—knowing where it can and cannot help is more important than ever.
  • Key Lesson: AI is a starting point, not an ending point; validate important information elsewhere.

2. Diversification, Volatility, and Staying the Course

• International and non-Tech Investing
  • OG: Despite US tech’s continued dominance, 2025 saw international markets outperforming. “Diversification still matters… Even though Nvidia is kicking everybody’s butt right now, we should still rebalance.” (19:23)
  • Jesse echoes: “The hardest times to make an investment decision also, in hindsight, end up being the best times…Reversion to the mean is an iron law of investing.” (21:16)
• Crypto & Volatility
  • Paula on crypto: “The story with crypto this year was a story of volatility…You can confirmation bias that in either direction… but the true story is simply one of volatility.” (22:42)
• Cash as an Asset Class?
  • Joe and OG discuss whether 2026 will require bigger cash reserves due to AI risks/job insecurity. OG responds, “No, I don’t think [the need for cash] is any different than any other period of time…If you have some personal knowledge [of layoffs], then yeah, squirrel away a little bit.” (23:57)
  • Don’t time or react excessively—maintain the right emergency fund, but don’t pile up cash for vague doom.
• Reacting to Market Events vs. Staying Passive
  • Jesse recounts the “tariff tantrum,” a 20% drop-and-rebound over mere weeks, reminding long-term investors: “It was a perfect little microcosm... such a sharp decline…and then such a sharp rally. What a perfect little microcosm of some of the tribulations that long term investors have to suffer through…” (26:17)
  • Paula: “Dollar-cost averaging and not paying attention to the headlines is the strategy that over time has proven more times than not to work...In almost anything else, effort and reward go in lockstep; investing is one of those extremely rare fields where …that simply isn’t the case.” (28:49)
  • OG’s analogy: Don’t go to the bar if you’re quitting drinking, and don’t check your portfolio daily if you want to avoid emotional investing mistakes.
  • Key Lesson: Remove the temptation and automate your investments. Progress comes from consistency, not active fiddling.

3. Personal Financial Planning: Expect Change—Always

• Dynamic Planning & Unexpected Policy Shifts
  • Jesse: “Financial plans need to be dynamic…your financial plan … is a dynamic thing, and sometimes that change is triggered by government policy.” (49:07)
  • OG: Don’t treat plans as permanent. The smartest approach is, "point the boat in the right direction and start rowing...then reevaluate" as life happens (50:33).
  • Paula on Health Insurance: “Even if you were carefully watching [the news], that still would not give you enough time to save up the cost differential...I think it’s having a margin of error within your budget so that you can account for the unexpected.” (53:29)
• Housing Market & Interest Rates
  • Paula: Change can be slow. “This is actually in some ways the opposite...People were hoping for bigger interest rate declines this year. The Fed didn’t start lowering rates until relatively late…” (54:47)
  • Jesse: “You might sit and wait for mortgage rates to be lowered…but hope is not a plan.” (55:41)
  • On 50-year mortgages: OG is adamant—bad idea! He calls out “FOMO” and the danger of comparing your beginnings to others’ middles, noting that previous generations all felt ‘priced out’ in their twenties (57:00ff).

4. What Actually Matters: Family, Milestones, and Presence

• OG shares a personal lesson after celebrating his son’s high school graduation:
  • “If you have kids and you’re in the middle of the suck...this ends, and it ends with just an explosive ending...Embrace the suck, because this stuff ends, and it ends viciously...Nothing better than hanging out with the people that you care most about...Tomorrow's not promised everybody.” (60:46)
  • Joe’s reflection: “Saying ‘I’ll be happy when these other conditions happen’...is a mistake. Embrace where you are.” (63:49)

Notable Quotes & Memorable Moments

• Paula Pant on AI’s limits:
  “AI can sometimes give outputs that seem so confident and seem so well formed that you forget that it might be hallucinating.” (14:38)

• OG, tongue-in-cheek:
  “I don’t have any fear of AI except for the downfall of all mankind and just about everything everywhere. So other than that, I think it’s going to be okay.” (10:41)

• On Market Timing:
  “More people lose money preparing for bear markets than actually in bear markets, you know, so...I wouldn’t have any extra cash just because stock market’s at an all time high and politics are crazy and the world economy is…” (24:25, OG quoting Peter Lynch)

• On Emotional Investing:
  “You can’t get better at this by doing more of it. You get better by literally going into a coma and having your dollar cost average work.” (31:00, OG)

• Jesse, on rapid rebounds:
  “Nowadays maybe we’re all dopamined up so much that six weeks of negative stock performance really hits us.” (27:54)

• OG on family milestones:
  “Even though it kind of. You feel like it might suck a little bit, embrace the suck, because this stuff ends, and it ends viciously.” (60:46)

Timestamps for Key Segments

| Timestamp | Segment | |:-------------:|:-----------------------------------------------------| | 08:47 | Paula introduces AI as 2025’s defining financial story | | 10:41 | OG on AI—fear vs. excitement | | 14:38 | Paula and group discuss AI “hallucinations” | | 19:23 | OG on 2025: “Diversification still matters” | | 21:16 | Jesse on mean reversion & investing discipline | | 22:42 | Paula: 2025’s lesson is crypto volatility | | 23:57 | OG on cash and market panic | | 26:17 | Jesse on the “tariff tantrum”—market drop & rally | | 28:49 | Paula: Dollar-cost averaging beats market timing | | 31:00 | OG: “Don’t try to react to every headline!” | | 49:07 | Jesse: “Financial plans need to be dynamic” | | 53:29 | Paula: Budget for the unexpected, not the headlines | | 54:47 | Paula: Change can be slow—housing & rates in 2025 | | 55:41 | Jesse: Hope is not a plan in financial decisions | | 57:00 | OG on 50-year mortgages & generational comparison | | 60:46 | OG’s personal milestone: Make time for what matters | | 63:49 | Joe: “I’ll be happy when” is a trap—embrace now |

Final Takeaways

• Embrace and adapt to AI—but don’t overestimate its infallibility.
• Stay diversified; the ‘sure thing’ rarely lasts.
• Volatility and sudden events are part of long-term investing—automate and don’t obsess!
• Financial and life plans are dynamic—leave margin and adjust as needed.
• Don’t let ‘hope’ replace a real plan; build conservatism into big decisions.
• Be present for milestones—life changes fast, and moments with family and friends matter most.

Hosts & Contributors:

• Joe Saul-Sehy (Stacking Benjamins)
• OG
• Paula Pant (Afford Anything)
• Jesse Kramer (Personal Finance for Long-term Investors)

Packed with laughs, honest reflections, and sound financial lessons, this episode is a must-listen for anyone wanting to learn from the past year—and focus on what really counts for the future.