Episode 333

Why You're Always Broke (Even With Multiple Income Streams)—And How to Fix It Fast

Published on: 5th August, 2025

Are you hustling nonstop, juggling multiple income streams, and still feeling broke? You’re not alone—and you’re not bad with money.

In this episode of iDateMoney®, Lisa Drennon, your Wealth Activator and independent insurance broker, breaks down why making more money isn’t the answer—and what actually is.

You’ll discover:

  • The one shift that changes your entire financial story
  • How to pay yourself first using Lisa’s proven Money Multiplier System
  • Why pouring everything back into your business leads to burnout
  • The truth about financial peace (hint: it starts in your bank account)

Lisa shares real stories, actionable steps, and her personal journey to retiring early, building legacy wealth, and making money feel fun again. Plus, a sneak peek at her children’s book, LionPhin’s Money Adventures, coming Fall 2025!


Topics Discussed:


  • Why entrepreneurs stay broke (even with booming businesses)
  • The law of the land: Paying yourself first
  • Setting up business buckets with Novo
  • Using the Money Multiplier System in real life
  • Building a family legacy with financial literacy
  • Turning hustle into harmony through wealth alignment


✨ Quote to Remember:

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


🎁 Mentioned in This Episode:

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

If today’s conversation sparked an aha moment or gave you a new perspective on your relationship with money, we’d love to hear from you! Your journey to financial empowerment starts here.

✨ Here’s your next step:

Take the Money Archetype Quiz to discover your unique money personality and gain clarity on how to manage and grow your wealth. It’s a game-changer!

👉 Meet Your Money Archetype

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💬 Let’s Keep the Conversation Going

What resonated most with you from today’s episode? Share your thoughts by leaving a 🌟🌟🌟🌟🌟 Star Review & share the podcast with all of your entrepreneur friends who are ready to find #truewealth!

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

🗝️🌬️💖💸

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.