Think Business with Tyler

The Real Reason Most Businesses Fail with Chuck Blakeman

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Chuck Blakeman Built 13 Businesses Across 4 Continents—Then Discovered Why 99% of Entrepreneurs Fail

Chuck Blakeman was told he’d never be employable—so he built 13 businesses in 10 industries instead.


But after decades of grinding, he realized the real reason businesses fail isn’t cash flow, competition, or even bad luck…


It’s because the owner gets tired.


Now, he teaches entrepreneurs how to break free from the "American Nightmare"—scaling businesses that give them freedom, not just income.


This episode is a mindset reset for anyone stuck in the daily grind. Chuck reveals:


  • Why "making money" is killing your business (and what to focus on instead)
  • The #1 financial killer of healthy companies (hint: it’s not lack of profit)
  • How to stop selling to strangers and 10X revenue by serving your existing network
  • Why employees are a bad idea—and what to hire instead
  • The Africa disaster that cost him everything (and the one risk rule he broke)
  • How Richard Branson built a empire without reading a P&L
  • "Patient ambition"—why slow, profitable growth beats hyper-scaling

    Key Lessons
    • From "Income Producer" to Business Owner: Why most founders don’t actually own a business—they own a job.
    • Cash Flow vs. Revenue: How a 2M→
    • 2M→9M business collapsed (and how to avoid it).
    • Sell Less, Earn More: Why successful companies stop selling and start serving.
    • The Partnership Trap: "The worst form of business… unless it works."
    • The 3to5 Club: Where entrepreneurs finally say, "I don’t know" out loud.

      Host: Tyler Martin, Fractional CFO & Business Coach


      Struggling to scale profitably? Let’s talk:

      📅 Book a Strategy Call


      Full Show Notes: ThinkTyler.com/chuck-blakeman


      🎙 Subscribe: ThinkBusinessWithTyler.com


      Follow Tyler:

      🔗 LinkedIn | 📸 Instagram | ▶️ YouTube

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