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October 31, 2025 37 mins

This episode: From the Battlefield to the Boardroom: Chas Sampson on Confidence, Character, and the Power of Service.

 

Here’s what you’ll learn about:

Life's linear path vs. external circumstances. (0:04)

  • Chas Sampson joins the podcast to discuss life's non-linear path.

Overcoming adversity and building confidence through childhood experiences and taking calculated risks. (1:05)

  • Chas Sampson shares his personal journey of overcoming adversity and taking massive action to become a stronger person.
  • Chas's parents instilled confidence in him from a young age, encouraging him to be brave and try new things.
  • His first business venture at 12 years old was a lawn mowing service, which he expanded with the help of friends and lost control of due to lack of proper planning.

Personal growth, overcoming fear, and finding success through hard work and perseverance. (3:25)

  • Chas shared his experiences working in various businesses in a small North Carolina town.
  • He discussed how he overcame obstacles and built relationships with clients, including a white nationalist who taught him about finance and communication.
  • Chas emphasized the importance of respect and persistence in business, citing his successful lawn mowing business and subsequent work at Winn Dixie Grocery Store and Sonic.

Military service, transitioning to civilian life, and sports agency work. (6:54)

  • Chas explains how Military service taught him relationships matter, not tough acts.
  • War criminals often lack love, attention, and empathy.
  • Deployments showed Chas people want to be heard, respected, and loved.
  • Chas had multiple career options after leaving the military, including working in finance, football, and sports agency.
  • He invested in a pass-through draft for college athletes transitioning to the NFL, earning up to $100,000 in expenses and training.

Managing investment deals and NFL player representation. (11:54)

  • Chas faces challenges managing opportunities in his business, including selling the company or focusing on NFL players.
  • He prioritizes culture and team fit in hiring and growing his organization, using a strict evaluation process.
  • Chas aims to provide balance and solve the mission for clients, while also growing his mentorship programs and organizations.
  • He discusses different aspects of his job, including mortgage backed securities, mergers, and VA claims.
  • Chas highlights the importance of adapting communication s...

Chapters

  • (00:00:00) - Adversity Is Not a Barrier
  • (00:07:45) - Jim Crow on Caring For Others
  • (00:10:10) - Working at 14 on a Work Permit
  • (00:12:12) - Servants in the Military Speak Out
  • (00:13:56) - The Best Lessons Learned While in the Military
  • (00:16:17) - What was the biggest challenge coming out of the Military?
  • (00:18:28) - NFL agent Damian Knight on becoming an NFL agent
  • (00:20:35) - Private Wealth Management: Giving Back to the Community
  • (00:21:41) - Have You Got What it Takes to Lead the Fed?
  • (00:27:21) - What Do You Wear For Work?
  • (00:27:40) - How AI Helped Veterans With Their VA Claims
  • (00:30:13) - The VA Claims Process for Veterans
  • (00:32:53) - Coach K on Advice For His Kids
  • (00:34:24) - Drew Brees on Advice For Young Businessmen
  • (00:36:09) - How to Live the Life You Want to Live
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