The Money Mondays – EP153

“The Power of Financial Literacy: What Every Family Needs to Hear” with Troy Millings
Host: Dan Fleyshman
Guest: Troy Millings (Co-Founder, Earn Your Leisure, Invest Fest, EYL University)
Date: December 22, 2025

Episode Overview

In this episode, Dan Fleyshman sits down with Troy Millings, co-founder of Earn Your Leisure, Invest Fest, and EYL University, to discuss the critical role of financial literacy—especially for families and the next generation. The conversation covers why financial discussions are taboo in many households, strategies for teaching kids about money, the impact of fear on wealth-building, the creation and growth of "edutainment" events like Invest Fest, tips for investing and deal-making, the power of charitable giving, and keys to generational wealth.

The episode is designed to inspire listeners to break money taboos, educate themselves and their communities, and take action—whether through learning, investing, or giving back.

Troy Millings: Background & Origin Story ([01:33])

• Teacher in the Bronx, New York: Troy began his career in education, observing a lack of financial literacy being taught to youth, especially in inner cities.
• Early initiatives: Troy created a summer financial education program teaching core money principles—sharing, saving, spending, investing—to kids.
  • ”In the six weeks that I had kids, it felt so much more fulfilling... I gotta turn this into something.” (Troy Millings, [01:56])
• Partnership with Rashad Bilal: Troy’s best friend and financial advisor, co-taught with him for over a decade before Earn Your Leisure (EYL) became a brand.
• Turning point: Recording classroom sessions for social media led to widespread interest.
• Launch of EYL: What started with basement conversations and an iPhone grew into a global brand.

Breaking the Taboo on Money & Teaching Kids Financial Literacy ([04:17])

• Dan acknowledges that many grew up believing talking about money was “rude.”
• Troy relates: In West Indian communities, money talk was constrained to “save it.”
• “I am the generation of curse breaker... I’ve been super intentional about making sure my kids understand what money is and how it works.” (Troy Millings, [04:57])
• Strategies Troy uses at home:
  • Lead by Example: Open, visible money conversations in front of his children.
  • Hands-on Learning: Involve children with handling real money (counting out charity envelopes, seeing mortgage payments).
  • Investing Exposure: Gave his children each 1,000 shares of Nvidia through an exercised options call.
  • Connecting to Their World: Used examples like Roblox and Disney (which his kids were familiar with) to explain ownership and stock market basics.
  • Use Everyday Moments: “He’s watching me invest in the stock market... he owns shares of Nvidia. He loves to tell his friends he owns shares of Nvidia.” (Troy Millings, [06:53])
  • On Taxes: Troy taught his son about the IRS after his son innocently said, “I want to be the IRS because they take everybody’s money.” ([07:34])
  • De-stigmatize money talk: Don't let lack of knowledge keep money a secret.

Overcoming Fear & Complacency Around Money ([09:27])

• “Fear. Straight up fear. And I’ve watched it cripple people in my family. But fear is only conquered by education.” (Troy Millings, [09:45])
• People get comfortable at certain income levels and don’t push for more due to fear of failure and lack of information.
• Rashad’s advice to Troy when he hit $115,000 as a teacher:
  • “Don’t let making $100,000 a year stop you from making $100,000 a month... there’s no ceiling on what you can do as an entrepreneur.” (Troy Millings, [10:40])
  • Encouraged to step beyond traditional ceilings into entrepreneurship.

The Purpose & Power of Live Events: Invest Fest ([12:01])

• Why do large live events instead of just online training?
  • “It’s bigger than us... it’s about what we wanted to create for a community that didn’t have this.” (Troy Millings, [12:01])
  • Edutainment: Blending business with music, sports, food, and culture to create new, immersive experiences.
  • Growth: From 4,000 to 25,000 attendees—enabling more cross-networking, business deals, and inspiration.
  • Quoting Marcus Rozier (Invest Fest speaker):
    • “Sometimes in life you have to become who you’re going to be so somebody else can become what they’re going to be.” ([13:48])

The Value of In-Person Connection & Self-Investment ([14:36])

• “There’s nothing like the real life, in-person encounter... you don’t know who you’re going to meet, what idea can be sparked.” (Troy Millings, [14:52])
• Investing in yourself (tickets, travel, events): One idea or connection can change a household, or even a whole community.
  • Encouraging people to get into the right rooms and act on opportunities.

Navigating Investment Choices Amid Information Overload ([16:05])

• Social media bombards people with “what to buy”—stocks, real estate, businesses, etc.
  • Key is to find what interests you and seek mentorship or community in that space.
  • “If I learn it, I know I can teach it. And every day I’m trying to learn so I can teach.” (Troy Millings, [16:57])
  • Not an either/or: Choose what drives you and what will help build legacy for your family.

What Makes a Bad Investment Pitch? ([18:05])

• Red flag: “I need you” pitches that focus on the founder’s needs instead of offering value.
  • “How can this idea help? It becomes that selfish mindset. The value add... is always the first barrier.” (Troy Millings, [18:15])
• Preference for deals that fit into existing initiatives and show clear, mutual value.

Deciding Where to Invest: Growth, Tech, and Leadership ([19:47])

• Troy prioritizes:
  • Growth potential, particularly in tech sectors.
  • Future-facing ideas (AI, e-vehicles, e-commerce).
  • Strong leadership: Track record, confidence, history in the sector.
  • “You get to know the person who’s actually coming up with the idea... you combine it with all the other information.” (Troy Millings, [20:38])

Making and Structuring Partnerships ([21:18])

• STEP 1: Seek counsel—legal and from those experienced in your industry.
• “The worst thing you can do is be naive and say, ‘I know it.’... Those who go down that route have harsh ramifications.” (Troy Millings, [22:16])
• Troy emphasizes analyzing integrity, energy, and confidence before even considering paperwork.

The “Handshake Deal” Dilemma: A Lemonade Stand Hypothetical ([23:18])

• Dan presents a scenario: If two partners build multiple locations but only one continues after the other leaves post-handshake, does the absent founder retain 50%?
  • Troy argues yes—if there’s no agreement, he continues to own his share.
  • Dan notes that without written agreements, disputes are inevitable.
    • “Sign contracts even with your mom... because you might have different concepts of what we promised.” (Dan Fleyshman, [25:13])

Key to Transformative Financial Education ([26:25])

• Adults’ biggest realizations:
  1. Disbelief at what’s possible.
  2. “I wish I would have known sooner.”
• Solution: Take financial literacy back to schools with mandated, age-appropriate curriculum.
  • Launch of the EYL “Earn As You Learn” curriculum, starting with NYC, aiming to make financial education mandatory.
  • “How much more financially in-depth would we be if we had it early?” (Troy Millings, [27:46])
• Information is given, but execution is on the individual.

Charity, Giving Back & Community Impact ([29:06])

• Giving has been a core principle for Troy and EYL from the start—designed into youth programming.
  • “They’re learning the foundation of sharing and how good it feels to give back.” (Troy Millings, [29:39])
• Businesses and individuals alike should instill a culture of giving—without expectation of return.
  • “The more you give to the world, the more you get back... pour out into the world because that’s what we should do.” (Troy Millings, [30:12])

Generational Legacy: The "Wealth Transfer" Question ([31:12])

• Dan asks: If you build to a multi-billion-dollar level, what % do you leave to your children?
  • “Fifty-fifty doesn’t feel right… I’d say 30% for each kid. We’ll have charity in there as well... we want families to live on beyond them... it’s not just generational wealth—it’s sustainable wealth.” (Troy Millings, [31:30])
  • Stresses the importance of estate planning, trusts, and “guardrails” for future generations.

Where to Find Troy Millings & Earn Your Leisure ([32:42])

• Social: @earnyourleisure everywhere (Instagram, YouTube)
• Personal: @troymillings
• Projects: Market Mondays podcast, Invest Fest, financial literacy curriculum

Notable Quotes & Moments

• On Fear & Wealth:

  “Don’t let making $100,000 a year stop you from making $100,000 a month.”
  — Rashad Bilal (as quoted by Troy, [10:40])

• On Live Events:

  “We had to create something so that thousands, if not millions of people... can become who they’re going to be.”
  — Troy Millings ([13:55])

• On Teaching Kids:

  “Meeting them where they’re at, leading by example, not hiding it from them, not making it taboo.”
  — Troy Millings ([07:25])

• On Giving:

  “The more you give to the world, the more you get back from the world... but you shouldn’t care about what’s coming back.”
  — Troy Millings ([30:12])

• On Execution:

  “Our thing is like, the information is always going to be on us. The execution has to be on you.”
  — Troy Millings ([28:47])

• On Legacy:

  “It’s not just generational wealth—it’s sustainable wealth. How do we keep this going for generations?”
  — Troy Millings ([31:42])

Key Segments & Timestamps

| Timestamp | Segment | |-----------|------------------------------------------------| | 01:33 | Troy’s Origin Story & EYL Beginnings | | 04:17 | Challenging Money Taboos, Teaching Kids | | 09:27 | Overcoming Fear & Building Wealth | | 12:01 | Invest Fest & Community-building Philosophy | | 14:36 | Why Live Events Matter | | 16:05 | Picking What to Invest In | | 18:05 | Red Flags in Investment Pitches | | 19:47 | Troy’s Investment Philosophy | | 21:18 | Structuring Partnerships, Avoiding Handshakes | | 23:18 | Lemonade Stand Partnership Hypothetical | | 26:25 | First Steps in Transformative Education | | 29:06 | Charity & the Power of Giving | | 31:12 | Generational Wealth, Legacy & Succession | | 32:42 | Where to Follow & Get Involved |

Summary Tone & Takeaways

• Tone: Open, inspirational, and practical—combining authentic personal stories with actionable frameworks.
• Major takeaway: Breaking cycles starts with financial education at home and in schools, honest conversations, intentional investment in both personal knowledge and community, and powerful acts of charity. Formalizing agreements, continuous learning, and planning for sustainable legacy are crucial at every stage.

This episode is a rich, relatable blueprint for making financial literacy a family and community priority—one open conversation, event, or act of giving at a time.