Month: January 2026

Truth Is Stranger Than Fiction: Preparing for an AI-Driven Future (Ep. 56)

Truth Is Stranger Than Fiction: Preparing for an AI-Driven Future (Ep. 56)

Rapid technological change is no longer theoretical. In this episode, Greg DuPont reflects on how science fiction is becoming real life, and what that means for professionals, families, and the future of work.

In this episode, Greg DuPont explores how AI, automation, and exponential technologies are reshaping the economy faster than most people realize. Drawing from personal reflection, current events, and future-focused thinkers, Greg explains why knowledge workers are especially exposed to disruption and why resilience matters more than ever.

Greg discusses:

  • Why truth is starting to feel stranger than fiction in today’s economy
  • How AI and automation are quietly replacing knowledge-based roles
    What this shift means for people in their peak earning years
  • Why mindset, adaptability, and financial resilience matter more than specific skills
  • And more!

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The Business Owner Opportunity (Mini Series Ep. 6)

The Business Owner Opportunity (Mini Series Ep. 6)

Most small business owners work tirelessly for decades building something meaningful, yet many walk away with far less than they deserve. 

What separates those who capture real value from those who simply close their doors?

This week, Greg DuPont explores the hidden planning gaps that prevent business owners from realizing the full value of their life’s work. He reveals why most businesses under $10 million struggle to sell, how to structure exit strategies that actually work, and the critical conversations advisors must initiate to protect their clients’ legacies. Greg also shares the “bag of tricks” approach that helps attorneys and advisors ask the right questions at the right time.

Greg discusses:

  • Why most small business owners can’t sell their businesses for a reasonable value despite years of work
  • How to structure exit strategies using key employees and golden handcuffs to maintain continuity
  • The power of asking “What needs to happen in 5-10 years for you to be happy?” to transform planning
  • Why business owners view their companies as family, and how legacy thinking drives all decisions
  • The entity structure trap and how outdated business structures drain thousands in unnecessary taxes
  • And more!

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