How Leaders Lead with David Novak

Episode #271: Childhood Moments That Shaped the World’s Top Leaders

Date: December 25, 2025
Host: David Novak
Co-host: Kula
Theme: Reflecting on personal childhood stories and formative moments shared by top leaders from business, sports, and entertainment—showing how early experiences shape leadership philosophies and practices.

Episode Overview

This special holiday episode revisits some of the most memorable stories previously shared by renowned leaders on the podcast. Each guest reflects on a childhood moment or lesson that significantly influenced who they became as leaders. The episode is curated as a masterclass in personal development, resilience, authenticity, and the power of formative experiences.

Key Discussion Points and Insights

1. Jamie Dimon: Lessons from Family and Early Curiosity

[01:49-06:29]

• Mother’s Influence on Justice and Respect:

  • Story of his mother, Themis ("justice" in Greek), standing up for herself during a family disagreement.
  • Notable Quote:
    “She walked up to him and took her wine in his face and left the room… he came back and said, I just want you all to know your mom was right.” – Jamie Dimon [02:17]
  • Key Insight: Courage to stand up for what’s right and owning your mistakes as a leader.

• Parental Influence on Intellectual Curiosity:

  • Mother was a Freudian, pushing Jamie to explore "why" people act as they do, instilling deep curiosity about human motivation and psychology. “A lot of Freud was wrong. But it is a real insight into trying to figure out how the mind works.” – Jamie Dimon [03:09]

• Father’s Subtle Guidance into Finance:

  • Jamie was the only sibling interested in finance; father nurtured his curiosity rather than forcing a career path.
  • Lessons in humility from reading annual reports and learning value investing.
  • The concept of building something great, not just making money, shaped his ambitions. “But the interest was more about building something. Building something great…” – Jamie Dimon [05:44]

2. Andy Jassy: The Toughness and Focus of Competitive Tennis

[07:06-10:02]

• Tennis as a Mirror for Leadership:

  • Competitive tennis was intense and lonely, teaching self-accountability and resilience in the face of both victory and defeat. “When you lose, there’s nobody to blame but yourself. When you win, there’s no one to really celebrate with but yourself.” – Andy Jassy [07:16]

  • Importance of focus in crucial moments and the need to move quickly from success or failure. “You have to find a way to be good to yourself even when things go wrong.” – Andy Jassy [08:52]

• A Father’s Lesson on Excellence:

  • Story of running a slow mile at his father’s suggestion and being told, “If you’re going to run like that, why bother running? If you’re going to do something, do it.” – Andy Jassy [09:21]
  • Takeaway: Total effort is foundational to success; half-hearted attempts are not worthwhile.

3. Pat Kelsey: Discipline, Integrity, and Inspirational Coaching

[10:45-14:11]

• Family as Leadership Template:

  • Raised by a Marine father who believed in high accountability, honesty, and loving support. “My dad sees the world in black and white. There’s no gray area. He always chooses the right path regardless of the consequences. Tell the truth at all times.” – Pat Kelsey [12:25]

• Coaches as Key Mentors:

  • High school coach inspired through quiet strength, motivating players to excel without needing to be loud or domineering.
  • College coach’s tragic passing left a legacy of leadership ideals Kelsey still pays forward.

4. Mike Worth: The Power of Preparation and Overcoming Limits

[14:40-19:20]

• Relentless Work Ethic as a Team Advantage:

  • Childhood football coach pushed players with unorthodox, grueling practices, instilling the ethic that preparation can outweigh talent. “We didn’t have any special talent. We worked harder than everybody else.” – Mike Worth [15:27]

• Breaking Through Self-Imposed Limits:

  • Formative moment running up Lookout Mountain with an Ironman coach—discovered he could do what he thought was impossible. “He taught me that the only thing holding me back were the limits I put on myself.” – Mike Worth [16:39]

5. Zach Brown: Passion, Mentorship, and Building a Leadership Style

[20:05-22:58]

• Moment of Inspiration:

  • First exposure to racing at age 10 ignited a lifelong passion. “The sound, the speed. I remember the grandstand I was in. I remember the first racing driver I met, I remember who won…” – Zach Brown [20:18]

• Learning from Business Titans:

  • Used early exposure to entrepreneurs and executives in racing to learn “what to do and what not to do.”
  • Built success by analyzing both effective and flawed examples from mentors and assembling an advisory board to continue learning.

6. Lindsey Snyder: Authenticity in Family Business Leadership

[23:47-25:40]

• Forging an Authentic Identity:
  • Overcame stereotypes and expectations by embracing her true self—ultimately shaping the company’s culture by prioritizing values and connection over appearances. “It’s not the outside, right? It’s the inside… I just want people to know that they’re cared for, that they’re loved.” – Lindsey Snyder [24:42]
  • Letting go of the pressure to conform enabled her to lead in ways true to herself and her family’s values.

7. Damola Adam Alekin: Adaptability and the Universality of Excellence

[26:30-29:18]

• Adapting Across Cultures and Countries:

  • Grew up moving between continents; learned the universality of excellence and the importance of connecting to others regardless of background. “I learned that the best way to do well in any place that I went was just to be good at stuff. Excellence travels.” – Damola Adam Alekin [27:39]

• Parental Expectations and Aim for Mastery:

  • Parents set high expectations; father’s mantra: it doesn’t matter what you do, “if you’re the best at what you do, you can do well in this country.” – Damola Adam Alekin [28:28]

Memorable Quotes & Moments

• “Curiosity and trying to understand people… really fueled both his empathy for others and his intellectual curiosity.” – Kula on Jamie Dimon [06:29]
• “Tennis is brutal. I mean, you win, you celebrate alone. You lose, you really only have yourself to blame.” – Kula on Andy Jassy [10:02]
• “Limitations are often self-imposed, and a great leader sees potential in people that they don’t always see themselves.” – Kula on Mike Worth [19:20]
• “If you’re going to do something, whatever it is, do it and do it to your fullest or don’t do it.” – Andy Jassy [09:21]

Timestamps for Segment Highlights

• [01:49] Jamie Dimon on childhood lessons from his mother
• [04:25] Jamie Dimon on his father’s influence and entering finance
• [07:06] Andy Jassy on competitive tennis and his dad’s lesson
• [10:45] Pat Kelsey on the enduring influence of family and coaches
• [14:40] Mike Worth on extreme preparation and breaking limits
• [20:05] Zach Brown on falling in love with racing and learning from mentors
• [23:47] Lindsey Snyder on authenticity within a family business
• [26:30] Damola Adam Alekin on adapting to new cultures and excellence

Tone & Takeaways

Warm, reflective, and actionable—the episode doubles as a heartfelt reminder during the holidays to reflect on our own stories and the people who have shaped us. The anecdotes are practical, relatable, and delivered with the candor and humility that define great leadership. As David Novak puts it:

“Take a moment to think about the voices, the moments, and the memories that help make you the leader that you are today.” – David Novak [29:18]

This episode provides a tapestry of leadership wisdom—woven from personal histories, unwavering standards, pivotal “aha” moments, and the realization that leadership begins long before the boardroom, often in homes, on playing fields, and through the courage to be oneself.