The Stacking Benjamins Show – Holiday Kickoff Special: 2025 Lessons, Risky Bets, and an Alaska Surprise (SB1777)

Date: December 22, 2025
Hosts: Joe Saul-Sehy, OG, Doug
Guests: Joel Larsgaard & Matt Altmix (How To Money Podcast)

Overview

This festive episode welcomes Joel and Matt from the How To Money podcast for a lively recap of 2025’s biggest personal finance lessons, a candid discussion on risk, giving, and AI, and the debut of Stacking Benjamins’ new “vault” tool. The group brings their signature banter as they unpack notable events, financial trends, the dangers of risky bets, the surprising truths about renting, and how AI is shaking up everything from Wall Street to the workplace.

Key Discussion Points & Insights

1. Charity, Giving, and Community Impact

(13:12–19:49)

• Reflecting on the annual Voices for Good challenge, where the Stacking Benjamins and How To Money communities raised funds for financial literacy and other effective charities.
• Joel’s Charity: Supported Undue Medical Debt (formerly RIP Medical Debt) to buy and forgive crippling medical debts at a fraction of their price.
  • “They buy the debt, and then they forgive the debt. You thought you had $12,000 in medical debt. You don’t have it any longer.” – Joel (17:13)
• Matt’s Charity: Focused on GiveWell-vetted causes, supporting global health through proven, cost-effective charities (e.g., mosquito nets, nutritional supplements).
  • “Your dollars are going a lot further… to literally save lives as opposed to, okay, how do I want my personal life and the people around me to be able to benefit from my own charity?” – Matt (16:50)

2. Top 5 Lessons from 2025

(19:21–49:19)

5. Empty Political Promises and Taking Control

(20:28–24:45)

• The year was full of “floated” political ideas (tariff rebates, student loan forgiveness) that didn’t materialize.
• Lesson: Focus on what you can control (spending, saving, personal action) rather than being distracted by policy noise.
  • “They come in with all this stuff and when we... look at the financial plan and go, ‘Hey, are you ahead or behind on that number?’ ...All this third party crap never came back again. We just focused on what we could do.” – Joe (23:23)
• Notable Quote: “There are promises right and left and you just have to be discerning... Is it actually going to come to fruition?” – Joel (22:03)

4. Risky Financial Products Proliferate

(25:19–32:43)

• Rise in private equity in 401(k)s, day trading options, speculative real estate platforms, and gamified investing apps.
• Warning: Novelty and FOMO lure people into higher-fee, higher-risk investments, often resulting in loss.
  • “It’s even more incumbent on us to be wary, to be careful what we invest in.” – Joel (29:19)
• Referenced: Gamified platforms (Robinhood) making both good (IRA matches) and dangerous (leveraged ETFs, options) tools easier to access.
  • “It’s just a money grab... the more we can get regulators out of our way, the more money we can make more quickly.” – Joe (31:15)

3. Renting Isn’t Throwing Away Money

(32:43–36:34)

• Changing dynamics in housing: Down payments have soared; economics of buy vs. rent have shifted, especially in hot markets.
• Myth-busting: Traditional “homeownership builds wealth” platitude isn’t always true—especially in today’s cycle.
  • “Renting is not throwing away money... It’s easier than ever for folks to use platforms like Robinhood... to invest in the market in a way that was inaccessible to our parents.” – Matt (33:44)
• Market cycles dramatically affect the rent/buy calculus; job mobility also demands more flexibility.

2. The Government Shutdown: Why You Need to Prepare

(37:27–44:23)

• 2025 marked the longest government shutdown in U.S. history. Previously “stable” government jobs proved vulnerable.
• Lesson: Always have an emergency fund and a “bare bones” budget ready for unexpected disruption.
  • “It's really important... to have done that due diligence ahead of time, because guess what? Really sucks to get laid off on a Friday, and then Saturday be like, ‘What are we going to cut?’ ” – Joel (37:27)
• Ability to weather disruption is about liquidity and free cash flow, not just math on interest rates.
• Personalizing the federal waste debate: “Rather than fight about stuff I can’t control in Washington, where are my wasteful spending places?”* – Joe (41:41)

1. AI’s Era: Opportunity and Danger

(44:23–51:55)

• 2025’s defining theme: Massive impact and hype around AI—stock market gains concentrated in AI giants, existential job losses, new efficiencies, and consumer confusion.
• AI both empowers and deceives: Great for simple tasks or challenging big systems (like disputing a medical bill); unreliable for nuanced/local finance advice.
  • “There’s like a lot of fake stuff out there and then there’s some helpful parts of it.” – Joel (46:57)
• Notable Quote: “At any time I feel complacent and like everything is safe... this year proved that may be wrong.” – Joe (49:19)
• Gen Z is reevaluating college and career paths in response to AI’s disruption; cost-conscious education matters more than ever.

3. Notable Podcast Moments

• On Shortcuts in Investing:
  “You want to catch all the ladders, but there’s all these potential slides that can send you back tumbling down... Watch out, because that shortcut could come back to bite you.” – Joel (29:19)
• On Homeownership:
  “The discrepancy between what you're going to pay when you buy... versus rent... you’re going to save a lot of money renting in 2025.” – Joel (34:03)
• On Big Losses in Speculative Products:
  “A couple bad days of being in this Tesla leveraged ETF, I could lose all my money.” – Joel (29:31)
• On Preparation:
  “Plan for the worst, and then when the best happens, you’re always grateful.” – Joe (50:48)

Segments & Timestamps

| Segment | Start | Details | |------------------------------------|-----------|----------------------------------------------------------------------------------------------------------------------------------------------------------| | Holiday banter, Stacking Benjamins Vault | 00:20 | Hosts preview the holidays, promote their new subscription/data privacy tool, and announce the episode’s themes. | | Voices for Good Charity Recap | 13:12 | Joel & Matt discuss charity picks, proving personal finance listeners aren’t greedy but generous. | | Top 5 Lessons of 2025 | 19:21 | Letterman-style countdown with practical and philosophical takeaways; begins with political promises and wraps on AI’s impact. | | Government Shutdown & Emergency Funds | 37:27 | A real-world stress test for the oft-repeated “emergency fund” advice; lessons about job security and personal planning. | | On AI’s Disruption | 44:23 | How artificial intelligence is both an investment theme and a real-life risk for jobs and daily money decisions. | | Fun, self-deprecating banter | 52:53 | Spoofs and holiday humor—including plans for Matt's fake OnlyFans, “Santa” calls from Alaska about the budget crisis, and more. | | Holiday Trivia: “Santa Claus rally”| 55:34 | Doug humorously quizzes the crew about the end-of-year stock market bump’s festive name. | | Headline: Risky Bets & Prediction Markets | 66:53 | Investment News predicts risky gamified betting will spread; hosts warn about labeling speculative plays as “entertainment.” | | Community shout-outs, BAD groups | 81:40 | Highlights from local “Benjamin’s After Dark” meetups and the importance of connecting with other smart savers. | | Aftershow: Toilet Paper Economics | 89:46 | Hilarious end-cap about “real” wealth (buying TP without checking price) and holiday overindulgence. |

Memorable Quotes (with Timestamps & Attribution)

• On Politics & Control:
  "There are promises right and left and you just have to be discerning. And while it might sound great, like, is it actually going to come to fruition?"
  —Joel Larsgaard (22:03)

• On New Financial Risks:
  "With many more risky financial products at our fingertips, it's even more incumbent on us to be wary...what we invest in."
  —Joel Larsgaard (29:19)

• On Preparation & Resilience:
  "Really sucks to get laid off on a Friday, and then Saturday be like, ‘What are we gonna cut?’ Having done that exercise puts power in your hands..."
  —Joel Larsgaard (37:27)

• On AI’s Impact:
  “At any time I feel complacent and like everything is safe, this year proved that that may be wrong.”
  —Joe Saul-Sehy (49:19)

• On Speculation vs. Investing:
  “If you're nuking your plan because you think that, oh, well, this is my investment account, I'm investing in futures trading. No, you're not. You're gambling.”
  —OG (78:49)

Takeaways for Listeners

• Focus on what you can control: Don’t be distracted by the political noise or headlines outside your circle of influence.
• The basics remain undefeated: Simplicity in investing, foundational financial planning, and steady saving are more important than ever in an era of financial novelty.
• Preparation is power: Emergency funds and spending flexibility are nonnegotiable, even—especially—when life “feels stable.”
• New risks require new vigilance: Label your speculative investments as entertainment, not strategy, and never let them disrupt your foundational financial plan.
• AI is not just hype: Its opportunities and dangers are real, both for your investments and your career. Stay curious, adaptable, and skeptical.

For the Holidays and Beyond

• Give intentionally: Supporting effective charities and local causes can multiply your impact.
• Cherish community: Whether at holiday parties, trivia time, or local meetups, financial literacy is more fun (and sticky) together.

For more insight or to revisit the year’s best financial advice, tune into The Stacking Benjamins Show and the How To Money podcast!

“Take some advice from Joel and Matt. If you focus on what you can control, the events of 2026 and beyond won’t control you.” —Doug (87:00)