Encouraging Teen Entrepreneurship and Earning

In this solo episode, I dive deep into one of the most vital life skills we can teach our kids—financial literacy. From Halloween costumes to quarterly financial reviews, I walk you through my real-life journey of raising four boys with a focus on money management, financial responsibility, and the value of earning over entitlement. This isn’t about theory—it’s about what I’ve tried, what’s worked, and the lessons I’ve learned the hard way.

Whether your kids are 5 or 19, this episode delivers actionable ideas and candid reflections to help you guide your children toward a financially empowered future. If you’ve ever wondered how to talk to your kids about saving, spending, budgeting, or even compound interest—this is the episode for you.

[0:00] - Introduction

[1:27] - Feeling unequipped as a dad when it comes to teaching kids about money

[2:22] - Shocking statistics about the state of money management in America

[4:04] - A peek into how I started teaching money to my younger kids

[6:10] - The Halloween costume system: chores for rewards

[8:48] - Teaching the value of delayed gratification through real choices

[10:07] - Why even young kids can handle more responsibility than we think

[12:01] - Using a simple allowance system to teach saving, giving, and spending

[12:47] - Bringing my teens to financial advisor meetings

[13:51] - The impact of exposing kids to real-world financial conversations

[14:36] - Teaching compound interest and the power of investing early

[15:18] - Setting up budgeting tools like EveryDollar for teens

[15:57] - My son’s dog-walking side hustle—entrepreneurship at 17

[17:02] - Why real-life problem solving is the best financial teacher

[18:33] - Encouraging kids to budget their own money and learn from mistakes

[19:46] - New free resource: “25 Questions for the Car” to spark connection

[21:03] - Final thoughts and heartfelt thanks to the community

1. Start Early with Financial Lessons

Even young kids can begin understanding the basics of money through age-appropriate systems like chores for rewards, visual goal tracking, and simple budgeting methods. It’s never too early to introduce financial literacy.

2. Teach Earning Over Entitlement

Using real-life goals—like Halloween costumes or name-brand shoes—can help kids grasp the concept of earning. When kids work for what they want, they value it more and learn essential decision-making skills.

3. Make It Real for Teens

Bringing your older kids into financial conversations, like advisor meetings or discussions about interest and investing, empowers them to make smart money decisions now and in the future.

4. Use Tools That Promote Independence

Programs like EveryDollar are great for helping teens budget and track their spending. This teaches them accountability and gives them a sense of control over their finances.

5. Connection Is the Catalyst for Teaching

Use intentional questions and shared activities to create moments of connection. When you’re interested in your kids’ lives, it opens the door to deeper, more impactful conversations—including those about money.

• Free Resource: 25 Questions for the Car — https://thedadedge.com/1389

• Budgeting Tool: EveryDollar — https://www.everydollar.com/

• thedadedge.com/kidquestions

If this episode helped you shift your mindset about parenting and money, take a moment to rate, review, and share it with another dad who could benefit. Your support helps us reach more fathers who are ready to lead with intention.

Live Legendary.