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/

💼 Brought to You By Our Partners:

• ✅ uSource: All-in-one hub for the facility maintenance industry – Start Free Trial
• ✅ Team Engine: Hire, communicate, and manage your workforce – Learn More
• ✅ Swept: Janitorial software that scales with you – Check it Out
  
  
  

👥 Join The Profitable Cleaner Community

• Facebook Group: https://www.facebook.com/groups/profitablecleaner/
• Join to be a member to our Profit Advisory Board (Business Growth Community)

📲 Follow Us:

• 📸 Instagram → @profitablecleaner
• 💼 LinkedIn → The Profitable Cleaner
• 📘 Facebook → The Profitable Cleaner

Text Our Community JOIN today

Support the show

This episode is proof that mindset, hustle, and heart can take you farther than any résumé.

In this deeply personal and powerful conversation, James sits down with Jay — a successful entrepreneur, relationship-driven barber, and now cleaning company owner — to unpack how he went from cutting hair in his basement to securing a $300,000 commercial cleaning contract.

Whether you're building your janitorial business from the ground up, looking to break into larger contracts, or trying to balance business with family life, this episode will speak to your core.

Jay opens up about:

• Starting with nothing but clippers and a vision
• The importance of humility and human connection
• Why mastering relationships beats mastering sales tactics
• How Cleaning Prophets changed everything
• The real mindset that separates dreamers from doers
  
  

💡 What You’ll Learn:

• ✅ How to scale from zero to $300K without prior experience
• ✅ Why relationships beat marketing in service businesses
• ✅ How to outgrow legacy clients without losing momentum
• ✅ What it actually takes to build trust and loyalty
• ✅ The real reason consistency trumps hard work

⏱️ Episode Breakdown:

• (00:00) – From the Barber Chair to the Boardroom
• (06:10) – Growing Up Different, Leading With Grit
• (13:45) – Starting With Nothing, Building Something Real
• (21:00) – Why Relationships Will Always Outperform Marketing
• (28:30) – The $300K Cleaning Contract Nobody Saw Coming
• (37:40) – What Most New Cleaning Business Owners Get Wrong
• (44:20) – Leveling Up as a Leader, Father, and Man
  

💼 Brought to You By Our Partners:

• ✅ uSource: All-in-one hub for the facility maintenance industry – Start Free Trial
• ✅ Campos Law: Legal partner for cleaning companies – Book a Call
• ✅ Team Engine: Hire, communicate, and manage your workforce – Learn More
• ✅ Swept: Janitorial software that scales with you – Check it Out
  
  
  

👥 Join The Profitable Cleaner Community

• Facebook Group: https://www.facebook.com/groups/profitablecleaner/
• Join to be a member to our Profit Advisory Board (Business Growth Community): https://advisoryboard.profitablecleaner.com/

📲 Follow Us:

• 📸 Instagram → @profitablecleaner
• 💼 LinkedIn → The Profitable Cleaner
• 📘 Facebook → The Profitable Cleaner

Text Our Community JOIN today

Support the show