#08: The Hardest Part of Winning Is Noticing When You’re Losing

Winning feels great… until it blinds you. Success hides cracks, momentum covers decay, and leaders often don’t notice performance erosion until it’s too late. The hardest part isn’t achieving growth…it’s seeing where it’s already slipping.

In this episode, you’ll learn how to:- Recognize the 3 quiet but deadly warning signs of success.
- Proactively spot the subtle patterns that signal performance erosion.
- Ask the right questions to reveal what’s quietly breaking beneath your wins.
- Lead through growth without letting success become your downfall.

This is a candid look at why success is often the most dangerous phase of leadership—and what separates leaders who sustain momentum from those who slowly unravel without noticing.

Episode Breakdown:
00:00 Intro
03:05 Setting the Table: Success, Growth & Silent Decay
07:42 The Four Categories of Warning Signs of Success
18:52 Entering the Performance Erosion Phase
24:28 Warning Sign #1: Revenue Hubris
43:01 Warning Sign #2: Random Acts of Accountability
58:30 Warning Sign #3: Sowing the Seeds of Decay
1:15:18 Leadership Drift & How to Respond
1:21:45 Practical Steps: Cost-to-Value Reviews, Culture Audits, and System Readiness
1:23:05 Outro & Sneak Peek: Raising Capital