Episode 287

From Hustle to Harmony: Real Estate Lessons with Betsy Pepine

Published on: 4th May, 2025

In today’s empowering episode, Lisa sits down with Betsy Pepine — serial real estate entrepreneur, nonprofit founder, and advocate for empowering women and children. Together, they dive deep into what real wealth truly means beyond dollar signs. Betsy shares her inspiring journey from a laid-off pharmaceutical executive and newly single mom to a full-time real estate powerhouse who created multiple thriving businesses.

Learn how Betsy built wealth on her own terms, how she defines success (hint: it’s not the mansion or the fancy cars), and her refreshing perspective on money, travel, and living a life aligned with your values.

Topics Discussed:

Why real estate became Betsy's path to financial sovereignty


How to tell if you’re ready to go all-in on your dream


The difference between chasing money and building lasting wealth


Setting your own “enough number” for financial happiness


How to wisely invest your time and resources for true joy


Personal insights on first-class flights, decluttering, and the true ROI of peace


Lisa’s personal milestone: 150 days alcohol-free and the clarity it brings!

Connect with Betsy here:

https://www.betsypepine.com https://www.linkedin.com/in/betsypepine/ https://www.instagram.com/betsypepine/

https://www.facebook.com/betsypepine

https://www.tiktok.com/@gainesvillerealtor

https://www.youtube.com/@BetsyPepine

https://substack.com/@betsypepine

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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
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. 🗝️🌬️💖💸
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.