Host Mark Cundiff shares five leadership insights from his conversation with Jay Jacobson, a longtime funeral home director, entrepreneur, and leadership consultant, centered on Jay’s book "Lead by Legendary Example."

The takeaways include: leadership is demonstrated through daily behavior rather than titles; integrity is revealed in quiet moments and in crises through truth-telling and owning mistakes; effective boards and teams surface disagreement to reach better decisions; true presence requires turning down distractions and giving full attention; and collaboration multiplies wisdom while control isolates it, illustrated by contrasting medical experiences at the Mayo Clinic versus a local hospital.

Mark encourages listeners to download the episode leader notes, check out Jay’s book, subscribe to the podcast, and leave a five-star rating.

Free Learning To Lead Resources

• Free Book: The Trust Gap
• The Learning To Lead Newsletter
• LeaderNotes

🔎 About LeaderNotes

LeaderNotes is a quick-hit companion to each episode of The Learning to Lead Show. In just 5–10 minutes, Mark Cundiff recaps the top leadership insights, frameworks, and action steps from each interview, designed for busy, growth-minded leaders who want to review and apply the episode’s biggest takeaways on the go. It’s like the highlight reel + playbook—all in one.

Contact Mark at: mark@markjcundiff.com

Episode Summary – Jay Jacobson | Lead by Legendary Example

Mark Cundiff welcomes Jay Jacobson—funeral director, entrepreneur, bakery owner, and leadership consultant—to the Learning to Lead Show. Drawing from his book Lead by Legendary Example, Jay shares six pillars of leadership shaped by real-life experiences across business, crisis response, and community leadership.

Jay reflects on his journey from childhood entrepreneur to funeral service leader and national board member, emphasizing that leadership is not declared—it is lived. He highlights defining moments, including the United 232 crash response in Northwest Iowa, where competing funeral directors united to serve families and coordinate disaster efforts—demonstrating integrity, collaboration, and leadership under pressure.

The conversation explores:

• Living with integrity through daily actions, especially in crisis
• The power of constructive disagreement in effective leadership and governance
• Vision that goes beyond short-term results to truly serve people
• Presence—giving undivided attention at work and at home
• Servant leadership shaped by personal hardship, family challenges, and empathy
• Collaboration in medicine, disaster response, and community leadership
• The difference between adaptability and compromise—holding values steady in changing times

Jay also discusses mentoring young people, building character early, and creating environments where future leaders can grow. He shares how continuous learning—through books, experience, and evolving tools like AI—remains essential for leaders who want to stay effective and relevant.

His book combines powerful stories with a practical 10-week leadership development framework, built to help leaders live their values, serve others, and lead with lasting impact.

Key message: Never stop learning. Leadership is lived one decision, one action, and one example at a time.

Free Learning To Lead Resources

• Free Book: The Trust Gap
• The Learning To Lead Newsletter
• LeaderNotes

🔎 About LeaderNotes

LeaderNotes is a quick-hit companion to each episode of The Learning to Lead Show. In just 5–10 minutes, Mark Cundiff recaps the top leadership insights, frameworks, and action steps from each interview, designed for busy, growth-minded leaders who want to review and apply the episode’s biggest takeaways on the go. It’s like the highlight reel + playbook—all in one.

Contact Mark at: mark@markjcundiff.com

Host Mark Cundiff shares five takeaways for growth-minded leaders from a prior Learning to Lead Show episode with Dr. Matt Wilmington (Episode 28), a longtime mentor known for asking probing questions.

The episode theme is “Leading Inside Out,” emphasizing that leading from external pressures and performance leads to burnout, especially mid-career, while the real mission flows from the inside out.

Cundiff highlights lessons from leading volunteers at Thomas Road Baptist Church: in volunteer environments, you must motivate rather than manipulate and focus on the currency of mission, meaning, belonging, and clarity (and in corporate settings, respect, growth, purpose, flexibility, recognition, and trust).

He reinforces that leaders never outgrow the fundamentals—mission, values, strategy, and role clarity—and that “vision leaks,” so repeating the vision is necessary.

Wilmington also stresses recruiting as critical: slow down hiring or pay later, using The 6 Cs

1. Christ Life
2. Character
3. Creed
4. Calling
5. Competence
6. Chemistry

He uses a red/yellow/green interview debrief tool; desperation hires become expensive organizational debt.

Finally, Cundiff shares Wilmington’s onboarding insight: new hires should be trained not only on tasks but also on the leader’s communication style, rhythms, expectations, and what success looks like, to avoid unnecessary mistakes.

Cundiff encourages listeners to download the episode and leader notes, subscribe, share, and leave a five-star rating.

00:00 Welcome + Why Dr. Matt Wilmington’s Questions Matter
01:16 Takeaway #1: Lead Inside-Out (Avoid Mid-Career Burnout)
02:27 Takeaway #2: What Volunteers Teach—Motivate, Don’t Manipulate
03:24 Takeaway #3: The Basics Never Graduate (Mission, Values, Strategy, Clarity)
04:32 Takeaway #4: Recruiting Is the Game—Slow Down Now or Pay Later
06:42 Takeaway #5: Onboarding That Works—Train Them to the Leader
08:25 Wrap-Up: Episode 28 Resources + Subscribe/Share

Free Learning To Lead Resources

• Free Book: The Trust Gap
• The Learning To Lead Newsletter
• LeaderNotes

🔎 About LeaderNotes

LeaderNotes is a quick-hit companion to each episode of The Learning to Lead Show. In just 5–10 minutes, Mark Cundiff recaps the top leadership insights, frameworks, and action steps from each interview, designed for busy, growth-minded leaders who want to review and apply the episode’s biggest takeaways on the go. It’s like the highlight reel + playbook—all in one.

Contact Mark at: mark@markjcundiff.com

In this episode of 'Learning to Lead Show', host Mark Cundiff interviews Dr. Matt Willmington, the Executive Pastor of Ministries at Thomas Road Baptist Church and Head of the Pastoral Training program at Liberty University.

Dr. Willmington shares his leadership journey, emphasizing the importance of living 'inside out' to avoid burnout. He discusses his leadership philosophy, particularly in the context of a large church with numerous volunteers, and explains how biblical principles guide his approach.

Dr. Willmington also delves into recruitment, training, and coaching strategies, offering practical advice and book recommendations for leaders. He concludes with reflections on balancing productivity and fruitfulness, the importance of self-awareness, and the evolving challenges leaders face today.

This episode is packed with actionable insights and tips for both seasoned and aspiring leaders.

00:00 Understanding the Inside-Out Mission

00:27 Introduction to Dr. Matt Wilmington

02:04 Matt's Leadership Journey

03:24 Current Roles and Responsibilities

05:23 Leading Volunteers vs. Paid Staff

09:42 Blending Corporate and Church Leadership

12:06 Recruitment and Team Building

25:17 Onboarding and Training New Leaders

28:55 The Importance of Staff Mentorship

29:45 Onboarding and Training New Employees

31:33 Coaching Future Church Leaders

31:59 Biblical Foundations for Leadership

34:48 Practical Lessons from the New Testament

37:16 Self-Awareness and Early Leadership Lessons

43:29 Balancing Productivity and Fruitfulness

49:33 Continual Learning and Personal Growth

51:22 Current Leadership Challenges

55:27 Conclusion and Final Thoughts

Dr. Matt Willmington's Contact Information:

• LinkedIn
• Email: matt.willmington@trbc.org
• Thomas Road Baptist Church
• Liberty University

📚 Books Mentioned

• The Advantage — Patrick Lencioni
• The Purpose Driven Life — Rick Warren
• The Purpose Driven Church — Rick Warren
• Leading from the Second Chair — Mike Bonem
• The First 90 Days — (referenced as an onboarding framework)
• Atomic Habits — habit stacking / building rhythms

Free Learning To Lead Resources

• Free Book: The Trust Gap
• The Learning To Lead Newsletter
• LeaderNotes

🔎 About LeaderNotes

LeaderNotes is a quick-hit companion to each episode of The Learning to Lead Show. In just 5–10 minutes, Mark Cundiff recaps the top leadership insights, frameworks, and action steps from each interview, designed for busy, growth-minded leaders who want to review and apply the episode’s biggest takeaways on the go. It’s like the highlight reel + playbook—all in one.

Contact Mark at: mark@markjcundiff.com

Leadership Insights from my conversation with Bobby Allen

In this episode of the Learning to Lead Show, Mark Cundiff highlights key insights from his conversation with Sergeant Major Bobby Allen, focusing on building trust and inspiring leadership.

The discussion emphasizes five key takeaways for growth-minded leaders: knowing your people as a strategic leadership priority, taking responsibility, valuing influence over position, staying calm under pressure, and fixing root causes rather than symptoms.

These lessons, drawn from Bobby Allen's extensive experience in both the Marines and industrial manufacturing, provide practical applications for effective leadership. Listeners are encouraged to revisit the full conversation in episode 26 for deeper insights and to download the related Leader Notes for additional resources.

00:00 Introduction to the Learning to Lead Show

00:32 Key Takeaway 1: Knowing Your People

03:23 Key Takeaway 2: Seek Responsibility

04:52 Key Takeaway 3: Influence Beats Position

05:37 Key Takeaway 4: Remain Calm Under Pressure

06:57 Key Takeaway 5: Fix Root Causes, Not Symptoms

07:47 Conclusion and Call to Action

Free Learning To Lead Resources

• Free Book: The Trust Gap
• The Learning To Lead Newsletter
• LeaderNotes

🔎 About LeaderNotes

LeaderNotes is a quick-hit companion to each episode of The Learning to Lead Show. In just 5–10 minutes, Mark Cundiff recaps the top leadership insights, frameworks, and action steps from each interview, designed for busy, growth-minded leaders who want to review and apply the episode’s biggest takeaways on the go. It’s like the highlight reel + playbook—all in one.

Contact Mark at: mark@markjcundiff.com

Building Trust and Inspiring Leadership with Retired Marine, Sergeant Major Bobby Allen

In this episode of the Learning to Lead Show, host Mark Cundiff interviews Bobby Allen, a retired Marine Corps Sergeant Major and seasoned maintenance and reliability leader.

Bobby shares his leadership journey, starting from his early days in the Marine Corps to his extensive career in the corporate world. He discusses key leadership principles such as seeking responsibility, knowing your people, and leading through influence rather than authority.

Bobby also provides practical advice for young leaders, emphasizing the importance of trust, humility, and emotional intelligence. The episode is packed with valuable insights and actionable steps to help leaders improve their skills and drive organizational success.

Don't miss the expert tips on how to handle culture change and the impact of AI on maintenance and reliability.

00:00 Introduction to Leadership Challenges

01:46 Welcome to the Learning to Lead Show

03:24 Bobby Allen's Leadership Journey

04:46 Key Leadership Lessons from the Marines

06:15 Transitioning to the Corporate World

08:06 The Importance of Seeking Responsibility

11:00 Leading with Influence and Informal Leadership

19:50 Challenges in Maintenance and Reliability

20:48 The Role of Culture Change in Leadership

31:32 Building Trust and Credibility

36:54 Recommended Leadership Resources

41:29 Conclusion and Final Thoughts

Connect with Bobby Allen:

LinkedIn

Free Learning To Lead Resources

• Free Book: The Trust Gap
• The Learning To Lead Newsletter
• LeaderNotes

🔎 About LeaderNotes

LeaderNotes is a quick-hit companion to each episode of The Learning to Lead Show. In just 5–10 minutes, Mark Cundiff recaps the top leadership insights, frameworks, and action steps from each interview, designed for busy, growth-minded leaders who want to review and apply the episode’s biggest takeaways on the go. It’s like the highlight reel + playbook—all in one.

Contact Mark at: mark@markjcundiff.com

Leadership Insights from my conversations with Rick Rando

In this episode of The Learning to Lead Show, host Mark Cundiff reflects on his conversation with Rick Rando, an eighth-degree black belt, discussing his key leadership lessons.

The episode is anchored by the idea 'What You Condone, You Endorse' and dives into five crucial takeaways: the importance of maintaining high standards, the essence of servant leadership with a backbone, establishing effective systems, and transitioning focus from individual to team success.

Mark underscores the need for leaders to provide candid feedback, create consistent systems, and foster a culture of trust and fairness, all while shifting from 'me' to 'we'. The episode is rich in practical advice and wisdom for aspiring leaders.

00:00 Introduction to the Learning to Lead Show

00:34 Key Takeaway 1: What You Condone, You Endorse

01:45 Key Takeaway 2: The Standard is the Standard

03:47 Key Takeaway 3: Servant Leadership Requires a Backbone

05:26 Key Takeaway 4: Systems Liberate, Not Limit

07:02 Key Takeaway 5: From Me to We

09:10 Conclusion and Final Thoughts

Free Learning To Lead Resources

• Free Book: The Trust Gap
• The Learning To Lead Newsletter
• LeaderNotes

🔎 About LeaderNotes

LeaderNotes is a quick-hit companion to each episode of The Learning to Lead Show. In just 5–10 minutes, Mark Cundiff recaps the top leadership insights, frameworks, and action steps from each interview, designed for busy, growth-minded leaders who want to review and apply the episode’s biggest takeaways on the go. It’s like the highlight reel + playbook—all in one.

Contact Mark at: mark@markjcundiff.com

What You Condone, You Endorse with 8th Degree Black Belt Grandmaster Rick Rando

In this episode of the Learning to Lead Show, host Mark Cundiff interviews Grandmaster Rick Rando, 8th Degree Black Belt, owner and president of Kick Masters Karate and host of the Victory Couch Podcast.

Rick shares insights from his extensive career in martial arts and business leadership. He discusses the importance of maintaining high standards, recognizing and addressing toxic influences, and the significance of servant leadership.

Rick also recounts his journey from starting martial arts to owning a thriving business, highlighting key lessons learned along the way, especially during challenges such as the COVID-19 pandemic.

The episode emphasizes the value of humility, continuous improvement, and building trust within teams. Rick's personal experiences and practical advice offer valuable takeaways for leaders in any industry.

00:00 Overcoming Toxic Relationships in Leadership

00:53 Introduction to the Learning to Lead Show

02:13 Rick Rando's Martial Arts Journey Begins

04:46 Early Leadership Lessons and Family Influence

06:04 Building a Successful Martial Arts Business

12:06 Servant Leadership and Team Culture

19:36 Balancing Humility and Confidence

23:11 Challenges and Growth in Business

27:12 Adapting to COVID-19: Safety Measures and Challenges

28:10 The Importance of Systems in Business

29:15 Continuous Improvement and Efficiency

31:45 Self-Leadership and Personal Growth

35:41 Building and Trusting Your Team

44:00 Lessons from Disney: Leadership and Service

47:02 Personal Development and Influences

49:46 The Role of Family in Leadership

52:00 Conclusion and Final Thoughts

Connect with Grandmaster Rick Rando:

• Email: rando@randospeaks.com
• LinkedIn
• randospeaks.com
• The Victory Couch Podcast (with Julie Rando)

Rick's Recommended Reading List:

• The Go-Giver — Bob Burg
• The Customer Rules — Lee Cockerell
• Rich Dad, Poor Dad - Robert Kiyosaki
• The Tipping Point - Malcom Gladwell
• Uncommon - Tony Dungy

Rick's Recommended Podcast:

• EntreLeadership - Dave Ramsey

Free Learning To Lead Resources

• Free Book: The Trust Gap
• The Learning To Lead Newsletter
• LeaderNotes

🔎 About LeaderNotes

LeaderNotes is a quick-hit companion to each episode of The Learning to Lead Show. In just 5–10 minutes, Mark Cundiff recaps the top leadership insights, frameworks, and action steps from each interview, designed for busy, growth-minded leaders who want to review and apply the episode’s biggest takeaways on the go. It’s like the highlight reel + playbook—all in one.

Contact Mark at: mark@markjcundiff.com