#195 What I Learned Losing $80,000 from a Bad Business Deal

The Profitable Cleaner

Most entrepreneurs measure themselves by how much they earn, what they own, or how much they invest. But what happens when your biggest investment goes bad—and you lose almost everything?

In this episode, James sits down with Ben Kennedy—a successful personal injury attorney, father, cancer survivor, and business owner—to talk about the mindset it takes to build a fulfilling life that goes beyond dollars.

Ben shares powerful lessons on:

• Losing nearly $100K to fraud (and why he doesn’t let it define him)
• Navigating cancer as a teenager and finding purpose through adversity
• Building trust and transparency in a traditionally “stiff” industry
• Why chasing more money can sabotage your joy (and how he let go)
• The real difference between success and fulfillment

If you’ve ever struggled with tying your identity to your income, this conversation will hit home.

Whether you’re leading a multimillion-dollar cleaning company or just trying to build something that matters, this episode is packed with stories and mindset shifts you won’t forget.

💡 What You’ll Learn:

• ✅ How Ben overcame cancer at 15 and used adversity to fuel purpose
• ✅ The mindset shift that helped him detach self-worth from net worth
• ✅ How to protect yourself from fraud (and recover from bad investments)
• ✅ Why humility and communication are the real superpowers in business
• ✅ The art of negotiation and building trust in any industry

⏱️ Episode Breakdown:
(00:00) – Why Net Worth Doesn’t Define You
(02:00) – Ben’s Early Career & Losing His Job in the Financial Crisis
(06:30) – Becoming a Lawyer After Cancer
(12:00) – Life Lessons From the Courtroom
(18:00) – Negotiation & Handling Difficult Clients
(26:00) – The $80K Investment That Went Bad
(35:00) – Processing Failure Without Losing Yourself
(42:00) – Detaching Success From Your Bank Account
(50:00) – Final Takeaways & Life Advice

💼 Want to Connect With Ben?

• 🔗 Website → https://kennedyinjurylawyers.com/
• 🔗 Connect on LinkedIn → https://www.linkedin.com/in/btkennedy/

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