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