Episode 343

Why Wealthy CEOs Win: 3 Money Habits You Can Steal Today

Published on: 9th September, 2025

Why do some business owners seem to grow wealth effortlessly while others hustle nonstop and still live paycheck to paycheck? It’s not luck. It’s not timing. It’s habits.

In this episode, Lisa Drennon, Wealth Activator and creator of the Money Multiplier System, reveals the three simple financial habits that helped her pay off over $100,000 in debt, retire early, and finally build true financial confidence.


Lisa shares her personal story—crying at her kitchen table with money coming in from multiple sources but nothing left in the bank—and the pivotal shift that transformed her finances forever. You’ll discover:

  • The #1 number every entrepreneur must know before making money moves
  • Why paying yourself first isn’t optional—it’s essential
  • How investing in systems and mentorship multiplies your time, energy, and wealth

If you’re ready to stop stressing about money and start operating like a wealthy CEO, this episode is your blueprint.


Resources Mentioned:

Quote to Remember:

“It doesn’t matter how much money you have—it’s what you do with it.” 🗝️🌬️💖💸

Thank you for tuning into this week’s episode of I Date Money! 🗝🌬💖💸

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Remember, it doesn't matter how much money you make; it's what you do with it

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Intro/Outro music "IDM" by Christa Lily

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About the Podcast

I Date Money
Rebuild financial stability after divorce—rewrite your money story with clarity and confidence.
Welcome to iDateMoney®, the podcast where divorced mompreneurs learn how to rebuild financial stability after divorce without spreadsheets, shame, or second-guessing every decision.

Hosted by Lisa Drennon—Wealth Activator, money strategist, and creator of the Money Multiplier System— this show is where clarity meets confidence.

Each week, Lisa shares raw stories, practical strategies, and spiritual insights to help you:

Release fear and guilt around money so you feel safe spending again.

Create steady income and financial security—even if your business feels unpredictable.

Confidently pay yourself, cover taxes, and provide stability for your kids.

Rewrite your money story so you can step into your role as a secure, empowered mom.

This isn’t your accountant’s podcast. It’s real talk for women ready to stop feeling broke, build true stability, and finally trust themselves with money.

Because it doesn’t matter how much you have—it’s what you do with it. 🗝️🌬️💖💸

About your host

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Lisa Drennon

Lisa Drennon, Wealth Activator & founder of iDateMoney® has been in the finance & insurance industry since 1987. Her unconventional Money Multiplier System transformed her money relationship to become a self-made millionaire, retire 2 ½ years early, pay $100K of debt in 6 months, & relocate to her beachfront dream home.