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
iDateMoney® helps mompreneurs manage cash flow, ditch debt, and build true wealth—without shame. Hosted by Wealth Activator Lisa Drennon, creator of the Money Multiplier System. It’s not what you make—it’s what you do with it. 🗝️🌬️💖💸
iDateMoney® Where Women Date Their Finances and Build Wealth—Without Shame.
They’ll tell you to hustle harder. Save more. Budget better. But here’s the truth: It doesn’t matter how much money you have—it’s what you do with it. 🗝️🌬️💖💸

Welcome to iDateMoney®, the podcast that helps mompreneurs take back control of their finances with clarity, strategy, and soul. Hosted by Lisa Drennon—Wealth Activator, money mindset expert, and creator of the Money Multiplier System—this show is where taboo ends and true wealth begins.

Each week, you’ll get a mix of raw conversations, mindset rewrites, spiritual insights, and practical strategies to help you crush debt without budgeting shame, master cash flow in your business and personal finances, save, spend, and give with purpose, and create a wealth plan you actually love living.

This is not your accountant’s podcast. This is real-talk money coaching for women ready to multiply what they already have and step into their financial sovereignty.

You’ll hear real stories. Tangible tools. Energetic alignment.
And the occasional money rant (because let’s be honest, some things need to be said).

Tune in, shift your money story, and start dating your finances—because wealth is your birthright, and it’s time to own it.

About your host

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Lisa Drennon

Lisa Drennon, Wealth Activator & founder of I Date Money™️ 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.