In this episode of the Masters of Resilience podcast, Mark Phillips and Ryan Seager sit down with Jon Reiner, who leads one of the top specialty insurance teams in the country. Jon shares his journey of building a high-performance culture rooted in humility, clarity, and relentless intensity. From empowering his team to take risks and learn through failure, to balancing the demands of leadership with family life, Jon offers a masterclass in resilient leadership.

Whether you’re scaling a business or leading a small team, this conversation is filled with practical wisdom and mindset shifts that will challenge and inspire you.

Chapters:

01:25 – Building a High-Performance Team

04:21 – Navigating Challenges and Uncontrollables

08:32 – Retention: Keeping Top Talent

10:24 – Culture of Intensity and Passion

12:35 – Finding and Nurturing Talent

15:04 – Empowering Growth and Responsibility

16:41 – How Leaders Handle Failure

20:01 – Delegating and Trusting Your Team

26:41 – Investing in Growth Through Consulting

29:48 – The Role of Humility and Healthy Paranoia

31:51 – The Challenge of Leadership

34:41 – Balancing Family, Work, and Discipline

38:15 – Learning from Great Leaders

42:56 – Staying Sharp: Habits, Health, and Routines

47:06 – Leadership Lessons in Patience and Emotional Control

What does it take to lead with integrity and still thrive in a high-stakes industry? In this episode, Ryan Seager and Mark Phillips chat with John DeAngelis, President and Co-Founder of DeAngelis Diamond, to explore a leadership model rooted in character, clarity, and generosity.

John shares his journey of building one of the country’s premier construction firms while holding fast to faith and family. He unpacks the challenge of balancing high support and high challenge in leadership, hiring for character over skill, overcoming fear with intentionality, and defining “enough” in a world that always demands more. With personal reflections on fatherhood, self-awareness, and legacy, this conversation is both deeply practical and profoundly inspiring.

02:09 — Navigating Unique Challenges in Construction

04:27 — Developing Leaders with Lives Worth Following

11:18 — Hiring for Character Over Skills

13:40 — Establishing Core Values in Leadership

18:20 — Overcoming Fear in Leadership

28:51 — Defining ‘Enough’ in Success and Generosity

33:50 — The Challenge of Generosity

35:25 — The Role of Fatherhood

41:28 — Navigating Work and Family Life

45:34 — Self-Awareness in Leadership

49:27 — Understanding God’s Sovereignty

52:57 — Defining True Success and Legacy

In this milestone episode of Masters of Resilience, Mark and Ryan take a moment to reflect on the journey so far—what they’ve learned from the conversations, the leaders, and the struggles along the way. They explore what it really takes to stay resilient: from practicing patience and managing energy, to building an unshakable inner game. Whether you’ve been here from the start or just tuning in, this episode captures the heart of what Masters of Resilience is all about.

Chapters

01:07 — Lessons from the Past Year

06:15 — Movement vs. Action: What’s Real Progress?

10:11 — Failure Isn’t the End, It’s the Way

12:50 — Mastering the Inner Game

17:14 — You Can’t Do It Alone: The Power of Support Systems

22:10 — What’s Next for Year Two