Podcast Summary: Stacking Benjamins Show

Episode: How to Talk to Kids About Money (Without Making It Weird) (SB1806)
Date: February 20, 2026
Host: Joe Saul-Sehy
Guests: Liv Roeder (senior in high school, host of The Live Lab), Karen Holland (founder of GiftingSense.org), John Lanza (host, Art of Allowance podcast)

Overview

This episode of The Stacking Benjamins Show revolves around family money conversations and how to make talking to kids about money natural, insightful, and empowering rather than awkward. Host Joe Saul-Sehy gathers a unique roundtable: a high school senior and podcast host (Liv Roeder), a youth financial literacy advocate (Karen Holland), and a parent-focused money educator (John Lanza). The panel shares personal stories, practical tools, and concrete tactics to help parents teach healthy money habits without overwhelming or alienating their children.

Tone: Fun, practical, open, and encouraging, staying true to the Stacking Benjamins approach of making money talk both approachable and meaningful for families.

Highlights & Key Insights

1. When Does Money “Feel Real” for Kids?

Timestamps: 13:00–19:51

• Liv Roeder: Money becomes real gradually—through experiences like getting an allowance, making independent choices, seeing family financial decisions, and participating in “grown-up” conversations.

  "What I want has a cost...I can't buy everything I want in a day. Money isn’t just a number; it has value." (13:05–13:31)

• John Lanza: Childhood memories of allowance tied to incentives (stopping thumb-sucking for a Lego set) underscore that intent doesn’t always match results. Long-term consistency is essential for learning.

  "The intention of what parents wanted, which often happens, right, with what really ends up transpiring." (15:22–15:51)

• Karen Holland: Her mom took a proactive approach, giving responsibility early. Learning through limited resources ("Plan beats no plan") and being forced to make tradeoffs built real-world skills.

  "My mother could have given me another five or ten dollars, but she held her ground..." (16:23–17:39)

2. The Power of Modeling and Gradual Responsibility

Timestamps: 19:10–24:55

• Kids pick up more than parents realize, especially from everyday financial behaviors, not just explicit conversations.

  "The quickest way to move the conversation from can I have it? to is it worth it? is to offer to split the cost."
  —Karen Holland (19:10–19:30)

• Allowance serves as a way to shift decision-making control, letting kids learn through low-stakes mistakes, and reflecting afterward (e.g., “circle back technique”).

  "The hard thing...was giving my kids the ability to mess it up and not say anything, letting them go ahead and make the bad decision."
  —Joe Saul-Sehy (19:51–20:55)

3. How Kids Actually Hear Money Conversations

Timestamps: 21:35–25:47

• Liv expresses the complexity and at times intimidation of money subjects (e.g., college forms, taxes).
• Experience and observation (“modeling”) matter more than formal schooling for behavior change.

  "Experience is number one, but learning from what the parents are doing is probably number two."
  —John Lanza (22:39–23:53)

• Honest conversations about resources and choices (e.g., weighing public vs. private college) foster awareness and empathy, not just guilt.

4. Engaging Kids of Different Ages: What Works

Middle Schoolers:

Timestamps: 26:34–29:19

• They’re more attuned than they seem; conversations should happen when they show interest or bring up needs.

  "The perfect time to talk about money is when your kids want some."
  —Karen Holland (28:09–29:19)

Age-Appropriate Involvement:

Timestamps: 31:44–36:22

• Don’t shield kids from all financial stress; involve them appropriately so they feel included and can help with solutions, which reduces anxiety and builds empowerment.

  "Kids want to participate in the solution for the family."
  —John Lanza (31:44–33:10)

Tackling Jargon & Intimidation:

Timestamps: 34:19–36:07

• Jargon in finance is intimidating; contrast with other subjects that teach vocabulary routinely. Familiarity breeds confidence; involve kids in real-world meetings when their interest arises.

5. Focusing on Values and Feelings, Not Just Numbers

Timestamps: 37:14–41:25

• Generosity can be a soft entry into money conversations, but spending is kids’ first real interest—so teach mindful, values-based spending.
• Use regret and satisfaction as teaching moments (e.g., using Gifting Sense’s DIMS score to anticipate and avoid buyer’s remorse).

  "I'm not in the feel bad about spending business. I'm in the think more about spending business."
  —Karen Holland (39:14–39:23)

6. Memorable Quotes & Moments

• Liv Roeder:

  "No matter how much I restrict myself from a Target, if I go and buy something, I'm going to feel happy. But it's all about this trial and error." (44:28–45:44)

• Karen Holland:

  “The speed at which we make decisions now is so much faster than it used to be, and it’s not because the species has evolved—it's our environment.” (53:42–54:50)

• John Lanza:

  "We all interact with money based on how it makes us feel." (39:32–40:54)

7. Tactics by Age: Building Money Skills "Without Making it Weird"

Early Elementary (6 yrs):

Timestamps: 46:25–47:45

• Start with allowance and three jars (spend, save, give).
• Make money non-taboo; let kids make basic decisions and even negotiate.
• Take advantage of kids’ readiness and interest (money = getting what they want).

Middle School:

Timestamps: 48:59–49:54

• Frame decisions around tradeoffs, delayed gratification, and opportunity cost.
• Practice foundational skills before high-stakes decisions.

  “Practicing making tradeoffs, practicing making choices... We want middle school students to have foundational skills and awareness.”
  —Karen Holland (48:59–49:54)

High School:

Timestamps: 50:04–51:33

• Real-world application through part-time jobs, managing their own income, experiencing independent choices and consequences.
• Parental involvement shifts to guidance and reflective questioning, not control.

8. Digital vs. Physical Money, and the Power of Pausing

Timestamps: 52:07–54:50

• Physical cash and jars remain valuable for teaching young kids because of the tangible experience, even as digital tools become more prevalent.
• Pausing and reflecting (“mindful spending”) is a transferable skill, and with minimal infrastructure, kids can surprise parents with their maturity.

9. If You Could Build Only One Skill…

Timestamps: 55:41–57:09

• Liv: Awareness—track earnings and expenses, reflect on spending, recognize patterns.
• Karen: Think before you buy—practicing the pause.
• John: Save a bit of every dollar—building the "pay yourself first" habit.

Notable Quotes (with Timestamps)

• Joe Saul-Sehy:

  "The hard thing about the allowance for me as a parent was giving my kids the ability to mess it up and not say anything, letting them go ahead and make the bad decision." (19:51)

• Karen Holland:

  "The perfect time to talk about money is when your kids want some. That's when they're all ears." (28:09)

  "I'm not in the feel bad about spending business. I'm in the think more about spending business." (39:14)

• John Lanza:

  "We all interact with money based on how it makes us feel." (39:32)

  "Physical moving of things into different jars... you're trying to teach them about making choices." (53:42)

• Liv Roeder:

  "It's reflecting and being aware of how much I spend and how much I'm making. So I'd say awareness." (55:41)

Key Takeaways & Actionable Tips

• Role-modeling and "learning by doing" are more effective than lectures.
• Early and gradual exposure—from “what do I want?” to “how do I negotiate my first salary?”—helps kids become confident money adults.
• Empower your kids by involving them in financial problem-solving as is age-appropriate, especially during tough times.
• Pause for reflection! Slowing down financial decision-making builds habits that fight the impulse-driven, frictionless spending environment children are growing up in.
• Let kids fail in small ways, then reflect. These "mini failures" prime long-term financial wisdom.
• Start with tangible money habits (physical cash, jars) and add digital tools as children mature.
• Involve kids in real money situations only when interest arises. Don’t force lessons—curiosity and buy-in are crucial.

Memorable & Practical Moments

• The “circle back technique”—let the child make the choice, then revisit it after some time to discuss if it brought value.
• Splitting the cost is a great way to move the conversation from “Can I have it?” to “Is it worth it?”
• Kids in workshops are capable of calculating the value of nearly anything—even the cost of buying Greenland.
• The highest-return money habit? Building conscious awareness (of cash flow, tradeoffs, savings, and emotional “return”).

Segment Timestamps (selected)

• Introductions & Panelist Backgrounds: 1:38–7:41
• Stories of When Money Became "Real": 13:00–17:46
• Modeling & Allowance Lessons: 19:10–21:13
• How Kids Hear Money Conversations: 21:35–24:45
• Age-appropriate Conversations & Involvement: 26:34–29:19, 46:25–49:54
• Handling Jargon & College Money Anxiety: 34:19–36:07
• Generosity, Values, and Buying Less: 37:14–39:23
• Teaching with Digital and Physical Money: 52:07–54:50
• Essential Money Skills: 55:41–57:09

Final Thoughts

This episode provides a playbook for families wanting to raise financially literate, confident, and resilient kids. The greatest gifts parents can give: modeling strong money values, letting kids learn through small stakes, and keeping conversations open, honest, and empowering. As Karen puts it, “Plan beats no plan”—so start planning those chats, and let the kids lead whenever they’re ready.

For more tools and tips from this episode:

• Liv Roeder: The Live Lab podcast
• Karen Holland: GiftingSense.org (with DIMS score calculators for smart spending)
• John Lanza: The Art of Allowance podcast

Links to all recommended tools and topics can be found in the show notes at StackingBenjamins.com.