The Escape & Empower Franchise Podcast | Buying Your First Franchise

“Wake Up and Smell the Roses”—Why Every Executive Needs a Plan B

Dave Greenberg and Pete Gilfillan

In this episode of Escape and Empower, Pete and Dave lay it all on the table: job security is a thing of the past, and senior-level executives who don’t have a Plan B are gambling with their future. Drawing from real conversations with candidates and decades of experience in corporate America, they break down ten urgent reasons every exec should be building a parallel path—before the storm hits.

Whether it's the rise of AI, corporate ageism, or the slow erosion of loyalty and compensation, today's episode is a wake-up call. Pete and Dave aren’t sugarcoating the harsh realities of modern executive life—but they are offering real alternatives: franchise ownership, consulting, real estate, or simply diversifying your income. If you're a 40+ corporate exec wondering whether it's time to explore a new path, this conversation will hit home.


In this episode, Dave and Pete discuss:

  • Why Job Security Is a Myth
    From flattening org charts to Tuesday layoff rituals, they reveal why even top execs are walking on a trapdoor—and why loyalty doesn’t go both ways.
  • AI Isn't Just a Tool—It’s a Replacement
    Exec-level tasks like strategy, hiring, and analysis are now being automated. If you're not planning around AI, you’re already behind.
  • Ageism and Underemployment
    Being overqualified is the new red flag. Pete and Dave break down the brutal math of trying to re-enter the job market at 55—and why it rarely adds up.
  • The Hidden Cost of Waiting
    Hanging on for that next bonus or promotion? You might be gambling away your best window to build real independence.
  • What Real Control Looks Like
    The most empowering shift is ownership. No politics, no performance reviews—just building wealth on your terms with purpose and freedom.


Key Takeaways:

  • Corporate loyalty is gone—prepare before you’re pushed out
  • A single income stream is risky; diversify now
  • AI is replacing roles, not just enhancing them
  • Ageism is real, and underemployment is common
  • Franchise ownership can be your runway, not a leap

“Time is money. If you’re exchanging your time for someone else’s wealth—you’re already behind.” — Dave Greenberg



CONNECT WITH PETER GILFILLAN

Meet with Pete: https://www.hireyourself.com/gilfillan/
Website:
https://www.hireyourself.com/
LinkedIn: https://www.linkedin.com/in/petegilfillan/

CONNECT WITH DAVID GREENBERG

Meet with Dave: https://calendly.com/empoweredfranchisee/virtual-coffee-with-dave-the-empowered-franchiee-web
Website:
https://empoweredfranchisee.com/
LinkedIn: https://www.linkedin.com/in/dave-greenberg-entrepreneur/