Ask Faleskini - The Midlife Crisis Clarity Compass

How to recognize the entrepreneurship trap? Interview Curtis Hearn

• Peter Faleskini • Season 7 • Episode 18

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0:00 | 26:19

In this episode of The Ask Faleskini Podcast, host Peter Faleskini speaks with certified financial planner, author, and wealth management expert Curtis Hearn about the hidden pitfalls of small business ownership, the realities of exiting a company, and how to avoid the "entrepreneurship trap". 

What You'll Learn in This Episode:

  • The Reality of Business Exits: Why statistics show that 9 out of 10 business owners struggle to successfully sell their business and harvest the value they've spent decades building. 
  • Burnout & Personal Experience: Curtis shares his own firsthand journey of building a firm, experiencing severe partner burnout, taking a 10-week sabbatical, and navigating a complex acquisition. 
  • Stepping Into the Buyer's Shoes: Why owners must look at their business from an outside perspective 3 to 5 years before an anticipated exit. 
  • Building Your Advisory Team: Why no owner should go through an exit alone, and the critical roles played by CPAs, attorneys, financial planners, and M&A specialists. 
  • The Post-Exit Identity Crisis: Exploring the psychological impact of selling a business, the parallel to Olympic athletes experiencing dopamine crashes after winning a medal, and why having a post-exit plan is vital. 


Key Takeaway:

"Your identity is almost certainly tied up in your business to some degree. You need to start the exit planning process early, assemble the right team, and plan not just for the financial outcome, but for your life and time after the sale." — Curtis Hearn 


About the Guest: Curtis Hearn is a certified financial planner based in Atlanta, Georgia, with over two decades of experience. He is the founder of Deep River Wealth, host of the Founder Money Podcast, and author of The Entrepreneurship Trap. 

Connect with Us:

  • Host: Peter Faleskini 
  • 🔔 New episodes drop weekly. Subscribe now to master financial planning, avoid burnout, and successfully navigate your business exit!


#Entrepreneurship #BusinessExit #FinancialPlanning #BurnoutRecovery #AskFaleskini 

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Peter's books


The Clarity Compass

Stop Midlife Burnout, Escape the Matrix, and Resolve Faleskini’s Complex


Faleskini’s complex

Diagnosing the Systemic Costs of Midlife Crisis and Advancing Holistic Pathways of Resolution


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