Ep. 27 - Embracing Founder Vulnerability: Lessons in Leadership and Growth

In this solo episode of the "Greatness From Small Beginnings" podcast, Keith L. Callaway delves deep into the emotional and psychological challenges faced by entrepreneurs and founders. Drawing from a poignant poem titled "I Am a Founder," Keith reflects on his personal experiences, sharing valuable lessons learned over his 40-year journey in business.

Key Points:

Introduction to the Episode:

  • Launching on a Monday morning to inspire and set the tone for the week.
  • Focus on the emotional and psychological struggles of founders and business owners.

Reading of "I Am a Founder":

  • A series of statements capturing the emotional journey of a founder.
  • Exploration of themes such as the desire for admiration, avoidance of conflict, and the perpetual state of anxiety.

Keith’s Personal Reflections:

  • The conflict between wanting to be admired and achieving results.
  • The impact of avoiding conflict on personal and professional relationships.
  • Lessons from his own entrepreneurial journey, including contributions to "The Joyful Entrepreneur."

Balancing Business and Personal Life:

  • The concept of "dad guilt" and the pressures of providing for the family.
  • Strategies for managing time and maintaining close relationships.
  • Reflections on the importance of gratitude and a mindset shift post-COVID.

Lessons Learned and Advice:

  • The importance of planning and time-blocking to achieve balance.
  • Encouragement to maintain close relationships and seek mentorship.
  • Insights into dealing with anxiety and the importance of self-compassion.

Closing Thoughts:

  • Re-reading of "I Am a Founder" to encapsulate the episode's themes.
  • Promotion of the Founder Conference in Virginia Beach, VA.
  • Motivational closing with a call to action inspired by Zig Ziglar.

Relevant Resources:

  • "The Joyful Entrepreneur" on Amazon
  • Founder Conference details


  • Zig Ziglar quotes and motivational insights
  • Ed Mylett's perspective on entrepreneurial guilt