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: Budget • Invest • Build Wealth After Divorce
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.