237: The Green Beret Who Learned to Lead with Empathy | Clarence Dingman

Whether in the military or business, the strongest teams are built on continuous learning, open communication, and a shared sense of purpose. In this action-packed episode, Damon sits down with Clarence Dingman, President of Defense Markets at PingWind, to uncover the leadership principles that drive high-performing organizations. Drawing from his Special Forces career and experience leading a dual-culture company through rapid growth and a major merger, Clarence provides a playbook for leaders at every level—whether you’re stepping up to a big new role or uniting teams after an acquisition. His stories highlight the power of active listening, building trust, and leaning into discomfort as a growth opportunity. If you want tactical strategies on culture, onboarding, and empowering your teams—even in tough times—this episode delivers. From military lessons to boardroom breakthroughs, get ready to learn what the best leaders keep doing—even after they reach the top. 

In this episode, you’ll learn: 

• The importance of anchoring company culture around lifelong learning (and how Clarence uses Michelangelo’s “And yet, I am still learning” to drive growth) 
• How to transition from being a doer to a resource-driven leader—and why empowerment beats micromanagement 
• Clarence’s firsthand playbook for merging two companies and uniting different cultures after a major acquisition 
• Why empathy and active listening are crucial for problem-solving and retention at scale 
• What to do when top performers clash with company values—and the hidden costs of tolerating toxic talent 
• Actionable tips on onboarding, employee engagement, and making feedback a two-way street—even as your team grows into the hundreds 

 

Timestamps: 

00:00 – Why environment matters more than the perfect job offer 

01:36 – The business case for “always learning” as a cultural value 

05:12 – Clarence’s military journey: from infantry to Special Forces 

08:36 – Accelerated learning: transferring military lessons to business 

11:00 – How empathy and active listening create win-win outcomes 

12:18 – Taking the leap: stepping into a challenging new leadership role 

14:56 – Advice for stepping outside your comfort zone 

16:49 – Navigating a merger: uniting two established cultures 

17:46 – Clarence’s approach to building trust and communication post-acquisition 

19:41 – Biggest pain points in scaling: change management and uncertainty 

21:09 – Learning to let go: moving from doer to resource agent 

24:03 – How to become a hero-maker (not just a hero) as a leader 

25:05 – Penguin’s employee-centric culture and retention strategies 

27:29 – Building core values with bottom-up input (not just top-down) 

30:54 – What to do when you need culture buy-in—or a culture do-over 

34:13 – How to handle high-performing but toxic team members 

37:51 – Penguin’s people-first onboarding process 

41:58 – Breaking down leadership barriers to get authentic feedback 

43:54 – Clarence’s leadership philosophy and final advice for listeners 

 

About Clarence Dingman 

Clarence Dingman is President of Defense Markets for PingWind, a leading DC-based provider of IT and mission support services to federal and defense agencies. Clarence’s career began as an Army infantry officer before he moved into Special Forces, serving 11 years and bringing direct expertise in leadership, unconventional missions, and culture-building under pressure. After partnering with PingWind’s founder and fellow veteran, Aaron Moak, Clarence now leads...