I Date Money

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


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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:
  • Prosperity Portal Membership – Join now for $37/month
  • Novo Business Checking (with Lisa’s referral link)
  • [The Money Multiplier System Workbook & Wealth Activation Guide – inside the Prosperity Portal]
  • Lisa’s upcoming children’s book: LionPhin’s Money Adventures: Discover the Magic of Saving, Spending & Sharing – Fall 2025

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

📲 Stay Connected

  • Join our exclusive community: Money Magnets: Wealth Women, Sovereign Souls
  • Follow me on Instagram for daily money tips and inspiration!

💬 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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I Date MoneyBy Lisa Drennon