Podcast Summary: Living Your Legacy

Episode: "Executive Strategy Leader: How to Build Teams That Win for Generations"

Host: Rudy Mawer
Guest: Dr. Cedric Howard, CEO of Howard Executive Consulting
Date: December 9, 2025

Main Theme & Purpose

This episode explores the critical shift from being a hands-on entrepreneur managing daily tasks to stepping into the role of a visionary leader who builds teams that succeed over generations. Rudy and Dr. Cedric Howard dive into how to define and communicate the “North Star” of an organization, recruit and develop the right talent, and foster cultures that transcend time. Dr. Howard draws on his decades of leadership in higher education and corporate consulting, offering practical strategies, personal stories, and actionable advice for business owners striving to leave a legacy.

Key Discussion Points & Insights

1. The Transition from Entrepreneur to Visionary Leader

• Why many entrepreneurs get stuck at small team sizes:
  • They excel at execution and getting their hands dirty but struggle when required to delegate, envision, and lead strategically.
    • [00:00] Rudy: “So many people never got past the 10–20 employee side...when it became more the leader visionary, they struggled.”
• The effort and mindset required:
  • Leadership is an intentional, ongoing effort. Entrepreneurs often resist the discomfort of learning new skills or reorganizing their roles.
    • [03:15] Cedric: “You have a desire, you have a vision, but it also requires effort...oftentimes we don't want to go through the effort.”

2. Building Teams with the Right Values and Culture

• Attracting Talent:
  • The process of interviewing and hiring is rigorous; only a fraction of candidates will align with the company’s vision.
    • [04:08] Rudy: “We might interview or invite 200–300 people for a job...then I’ll hire two or three of those and maybe one will turn out okay.”
• Culture as a Differentiator:
  • Start with purpose and vision, infuse work with ethics, emotional intelligence, and competencies.
    • [04:16] Cedric: “You gotta start with the purpose and a vision...you’re also creating a culture.”

3. From Manager to Visionary—Defining the North Star

• Leadership at Scale:
  • There’s a purposeful transition from “mom and pop” operation to business, and ultimately to corporation. It all starts with a clear North Star.
    • [04:46] Cedric: “What is your North Star? If you want to be a small organization...that is okay. But then you’ve got to transition...and then transition your business into a corporation.”
• Continuous Learning:
  • The most successful leaders learn (and unlearn) constantly as the business scales.
    • [05:03] Cedric: “You have to be willing to learn and learn and relearn what you're doing as you develop in each stage...”

4. Learning Leadership Versus Experiencing Leadership

• "School of Hard Knocks":
  • Unlike other disciplines, most entrepreneurs learn leadership by doing, making mistakes, and adapting.
    • [05:43] Cedric: “Most successful leaders have learned how to fail...we’ve learned how to fail so we don’t become failures.”
• The Power of Failure:
  • Failure is framed as necessary for growth—using the baseball analogy: succeeding 3 out of 10 tries puts you in the Hall of Fame.
    • [06:07] Cedric: “If you hit 3 out of 10 times, you’re considered...a Hall of Famer. But often we don’t see the seven times you missed and had to adjust.”

5. The Four Pillars for Building Teams That Win

Cedric distills his philosophy into four actionable areas:

1. Determine Your North Star (Vision)
   • Think in “bold, bodacious goals” and set aspirations on a generational scale.
     • [08:05] Cedric: “In Asia...they have 500-year plans for their companies. Not just five or ten year—they have five hundred.”
2. Develop a Successor Pipeline
   • Succession planning is often neglected; leaders should train others for roles beyond their current scope.
     • [11:35] Cedric: “Many companies fail because they haven’t developed a succession plan...are you training that next level of leadership?”
3. Surround Yourself with Value-Aligned People
   • Your network profoundly impacts your net worth. Seek strengths different from yours.
     • [13:59] Cedric: “Your network determines your net worth...It can’t be your friends—you’ve got to have some strengths very different to you.”
4. Be Proactive, Innovative, and Reflective
   • Innovate rather than imitate (blue ocean strategy). Learn from your errors, and plan ahead for transition and asset protection.
     • [15:37] Cedric: “How are you preparing yourself to learn from your mistakes? That’s being proactive rather than reactive.”

6. Keeping Vision Alive Within Teams

• Constant Reinforcement:
  • Repetition and affirmation are key—teams quickly forget long-term vision unless reminded regularly.
    • [10:44] Rudy: “Most companies only ever share it once a year...every Monday we do our all staff and the first ten minutes, we actually go back through all of our yearly goals and our vision...”
  • Cedric uses “Setting Notes” with small rewards to reinforce core values.
    • [11:25] Cedric: “A person gets a Setting Note. They also get a $5 Starbucks coupon...which reaffirms what we’re hoping to do.”

7. Building a Multi-Generational Legacy

• Thinking Decades Ahead:
  • True legacy is about establishing financial AND educational foundations for descendants you might never meet.
    • [17:18] Cedric: “How do I build wealth that my great grandkids are benefiting from? ...A person dies twice: when you physically die and when they’re forgotten.”
  • Ensuring your name is remembered is a core motivator for Dr. Howard’s work.
    • [17:54] Cedric: “I want to make sure that for decades and generations to come, they’re always calling my name.”

Notable Quotes & Memorable Moments

• On Learning Through Failure
  • [05:43] Cedric: “Most successful leaders have learned how to fail...we’ve learned how to fail so we don’t become failures.”
• On Vision:
  • [08:05] Cedric: “They have 500-year plans for their companies...That’s thinking multiple generations.”
• On Succession:
  • [11:35] Cedric: “Are you training that next level of leadership for the job you desire for them to have? Remember, learn, unlearn, relearn.”
• On Network:
  • [13:59] Cedric: “Your network determines your net worth.”
• On Legacy:
  • [17:49] Cedric: “A person dies twice: when you physically die and when they’re forgotten. And one day, the last time they called your name.”

Timestamps for Important Segments

• 00:00–03:15 – The entrepreneurial struggle: tasks versus vision
• 04:08–05:03 – Recruitment, culture, and leadership at scale
• 05:43–07:03 – Failing forward; the necessity of learning by doing
• 07:15–15:37 – Cedric's 4 pillars: vision, succession, network, and innovation
• 10:44–11:28 – Keeping vision “alive” with constant reinforcement
• 17:18–17:54 – Defining and building a lasting legacy

Conclusion

This episode offers both inspiration and direct, actionable strategies for listeners who wish to move from effective managers to legacy-minded executive leaders. Dr. Cedric Howard’s experience and storytelling make abstract principles real, from the importance of the North Star to the day-to-day reinforcement of values, hiring well, developing successors, and thinking beyond your lifetime. Listeners are left challenged to envision not just what they can achieve, but what they can establish for generations to come.

Find more from Dr. Cedric Howard:

• LinkedIn: Dr. Cedric Bernard Howard
• TikTok: Cedric B. Howard

"Keep building a legacy." — Rudy Mawer [18:28]