When It All Goes Wrong: Real Stories of Executive Debt in Action

Theory is helpful. But real-world stories are unforgettable.

In this week’s post, we explore a few standout case studies from the book that show how Executive Debt plays out in the wild. From cultural misfires to strategic implosions, these examples illustrate the warning signs—and what it took to recover (if they did).

1. Kodak: The Price of Strategic Inertia

Kodak invented the digital camera. But leadership chose to protect the film business instead of embracing the future. Strategic Debt compounded over decades—until disruption left them behind.

Lesson: Protecting the past at the expense of the future is one of the costliest forms of Executive Debt.

Fix it: Challenge legacy assumptions. Fund innovation—even when it threatens the core.

2. Uber: Culture at Any Cost

Uber’s aggressive growth came with toxic leadership behaviors and internal dysfunction. Cultural Debt built up quickly and became a reputational risk.

Lesson: Culture is not a “soft” issue. It has hard consequences.

Fix it: Build leadership accountability from day one. Don’t wait for scandal to act.

3. Yahoo: Talent Lost, Direction Scattered

Years of inconsistent leadership and shifting strategies created both Talent and Strategic Debt. Yahoo never regained its footing and became a cautionary tale of missed potential.

Lesson: You can’t execute without clarity—and you can’t keep talent without trust.

Fix it: Stabilize leadership vision. Build teams aligned around clear, measurable priorities.

Why This Matters:

These stories aren’t just about failure. They’re about choices—missed, delayed, or misaligned. At AspireSix, we help you avoid becoming a case study by recognizing debt before it becomes a crisis.

Let’s make sure you’re not writing your own cautionary tale. Book a call with AspireSix.