Business Buyers And Clean Books: What Almost Cost Jason Schappert His Exit

I Date Money

Ready to take your money from messy to magnetic?

In this episode of I Date Money, your Profit Strategist Lisa Drennon sits down with Jason Schappert, former broke entrepreneur turned 8-figure business owner and co-founder of Moolah Co-Pilot. From the tow truck at the end of his driveway to building the largest pilot training platform, Jason shares the raw truth about how bad money habits nearly cost him everything—and how he rebuilt smarter, leaner, and wealthier than ever.

Together, we unpack:

• How to stop leaking money and start multiplying it (even on a small income)
• The difference between an income problem and a spending problem
• What it really means to pay yourself first—and how Moolah automates it
• Why co-mingling personal and business finances can cost you a sale (and how to clean it up)
• What your bank account would say if it could talk—and how to fix what it’s trying to tell you

Whether you're in survival mode or scaling to your next million, this conversation pulls back the curtain and gives you real, actionable insights that you can implement today.

Topics Discussed:

→ From financial chaos to clarity: Jason’s story

→ Wealth psychology + the danger of co-mingling funds

→ Business buyers and clean books: what almost cost Jason his exit

→ Using tech like Moolah to set money on autopilot

→ Aligning your goals with your cash flow—without burnout

Resources + Connect:

🔗 Connect with Jason: [@moolahcopilot on all platforms]

🔗 Lisa’s Wealth Activation Guide: https://idatemoney.com/guide

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.

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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