The Stacking Benjamins Show

Episode: Financial Literacy for Kids + Are Annuities Actually Safe? (#SB1757)

Date: November 5, 2025
Hosts: Joe Saul-Sehy, OG, Doug
Featured Guest: Karen Holland (Gifting Sense)

Overview

This episode centers on two key topics: teaching financial literacy to kids, especially through the work of Karen Holland and her nonprofit Gifting Sense, and a deep dive into the current surge in annuity sales—questioning whether annuities are truly as safe as they appear.

The hosts bring their signature mix of fun banter, trivia, and practical personal finance advice "from Joe's Mom's basement." The central interview is a lively, insightful conversation with Karen Holland, who shares actionable strategies for helping children (and adults) build money sense that lasts a lifetime.

Key Discussion Points & Insights

1. The Urgency of Early Financial Literacy Education

• Scope of the Issue

  • “We develop our money habits, beliefs, our feelings about money very young… That gap, I call it a timing mismatch, creates a lifetime of completely avoidable stress.”
    – Karen Holland [08:10]
  • Financial literacy is a worldwide problem with lifelong consequences stemming from early habits.

• The Gap & The Opportunity

  • Kids develop strong attitudes and habits about money before they have the tools to make big decisions.
  • There’s more financial information available than ever, but accessing it isn’t the challenge—developing the confidence and appetite to use it is.

• Why Start in Middle School?

  • Middle school is a "developmental sweet spot":
    • Kids are beginning to prune unused neural connections, develop impulse control, and seek rewards.
    • “Pausing, gathering information, and reflecting before making a decision… is massively transferable.”
      – Karen Holland [13:50]
  • “If a fairy godmother landed on my shoulder... I would have a mindful spending, thinking before buying workshop in every middle school around the globe.”
    – Karen Holland [15:19]

2. Teaching Kids to Think Before Buying: The DIM Score

• Purpose of the DIM Score (Does It Make Sense?)

  • A self-guided tool (no login, no paywall) that prompts users—kids and adults alike—to pause and consider all the true costs and benefits surrounding a potential purchase.

• How It Works

  • “You just answer the questions on the screen… Are you interested in buying an item or experience? Then: what category? Then you walk through the true costs…”
    – Karen Holland [24:23]
  • Reveals “phantom costs” often overlooked (e.g., maintenance for pets, travel for events).
  • Encourages building a ‘business case’ for purchases—a valuable skill well beyond childhood.
    • “Parents, do not worry… They can generate a shareable summary of all the math and thinking they've completed… Oftentimes they do decide that they don't want to proceed.”
      – Karen Holland [28:13]

• Memorable Classroom Moments

  • “When does a young person get to work on a problem that matters to them in real time in school? Not very often.”
    – Karen Holland [23:06]
  • Kids routinely abandon impractical wishes (like Super Bowl tickets or a puppy) once the real numbers are clear.
  • “We had an 8th grade boy calculate the doesn't make sense score for the purchase of Greenland.”
    – Karen Holland [31:27]

• Benefit for Families

  • Results in “fewer, better quality requests to spend,” lowers family conflict, and prompts conversations about needs vs. wants.
  • Context transforms conversations, “turns impulse into insight, and collected insights become confidence.”
    – Karen Holland [33:29]

3. Building Lasting Money Confidence

• More Than Just Money: Life Skills

  • The process teaches kids (and adults) transferable skills: pausing, gathering information, reflecting, and building logical cases for decisions.

• Coping with FOMO and Media Influence

  • Social media amplifies “fear of missing out,” but teaching mindful spending empowers kids to critically evaluate wants.
  • “If you think somebody has no issues, you know what that means? It means you're not friends.”
    – Karen Holland’s father (quoted) [21:15]

• Practical Tools: Worth the Wait Goal Tracker

  • Visual, incremental savings goals on the fridge spark family cooperation and reduce arguments.
  • “She called it a mic drop… This piece of paper changed the family dynamic.”
    – Karen Holland [34:32]

• Environmental Side Effect

  • Mindful spending helps reduce waste—“the easiest way to be a planet protector.”

4. Spotlight on Gifting Sense

• Mission and Reach

  • Permissionless, scalable, and globally accessible financial education tools.
  • Workshops currently delivered in NYC and Toronto; educator webinars and online resources widely available.
  • “What donating to Gifting Sense does is it lets us keep this dream alive of permissionless, truly permissionless and scalable early financial education.” – Karen Holland [36:36]

• A Proven Model

  • Multi-year winner of the Maia Awards for personal finance excellence.
  • “We're teaching kids about money in a way that's immediately helpful… We reduce family arguments. We are preventing waste.” – Karen Holland [39:19]

Notable Quotes & Moments

• “Financial illiteracy is a solvable problem. And who doesn’t want to work on one of those in this day and age?”
  – Karen Holland [09:56]

• “Friction is your friend. Sometimes, with money, friction is your friend.”
  – Joe Saul-Sehy [18:49]

• “This is your PowerPoint.” (Karen’s advice for how kids can present their logic for big purchases to parents)
  – Karen Holland [28:11]

[Important Timestamps]

• [08:10] – The global scope of youth financial illiteracy
• [13:50] – Why middle school is the ‘sweet spot’ for this education
• [17:25] – How digital tools & frictionless spending make mindful spending harder
• [24:23] – How the DIM Score Calculator works
• [28:13] – How the DIM Score builds better family conversations
• [33:29] – The power of context in family financial conversations
• [34:32] – Success story: The Worth the Wait visual tracker (“mic drop moment”)
• [36:36] – How donations power Gifting Sense’s mission
• [39:19] – Karen’s fulfillment: “I love my work…”

Segment 2: Annuities—Skyrocketing Sales, But Should You Buy?

• [48:29] – Introduction of headline: annuity sales break record highs

• [50:07] – Breakdown: why annuities are being pushed and OG’s skepticism

• [51:37] – The real mechanics: “You’re trading away some of the upside in exchange for never having any downside.”

• [53:35] – When annuities might make sense: “An annuity is best used for income planning, not asset protection.”

• Warning to Listeners:

  • Annuities are often oversold, with fees and limits on your upside.
  • “Insurance companies are great at math and also are great at knowing that you may not be great at math.”
    – Doug [67:29]

Segment 3: Life Insurance Horror Story (Kyle Busch Case)

• [55:54] – Headline: NASCAR’s Kyle Busch loses $8.5 million in an insurance scheme
• [57:20] – OG deep-dive: How complex policies and big premiums can backfire, even for savvy high-earners
• [62:56] – Takeaway: If even the wealthy and well-advised can’t always understand these products, proceed with caution

Practical Takeaways

• Ask yourself (and teach your kids to ask): “Does it make sense?” before making purchases.
• Context and conversation matter more than just saying “no.” Transform every money decision into a learning moment.
• Make friction work for you: automatically save, add obstacles to spending, and track your goals visually.
• Be wary of complex financial products (annuities, indexed universal life). If you can’t clearly explain it to someone else, consider if it’s right for you.
• Support mission-driven, proven financial literacy nonprofits—like Gifting Sense—to spread these life-changing skills.

Learn More & Take Action

• Gifting Sense: giftingsense.com
• Donate to ‘Gifting Hope’ Campaign: stackingbenjamins.com/giftinghope
• Podcast newsletters & guides: stackingbenjamins.com/201
• Full episode & show notes: stackingbenjamins.com

Final Thoughts

This episode is a rallying cry to make financial literacy not just accessible, but engaging and personally meaningful for the next generation—and a timely warning about the seductive sales pitches of “safe” financial products. With warmth, real stories, and actionable advice, the Stacking Benjamins team and Karen Holland make the case that a few new habits and conversations can change lives.

“Two thirds of us buy things on the regular that we do not use or appreciate. And if we can do nothing other than stop that, we’re on the way to creating that investable surplus.”
– Karen Holland [40:57]

Episode summarized by podcast summarizer AI, preserving the original fun and practical spirit of Stacking Benjamins. All core content and lessons referenced; ads and non-content banter omitted.