Matt sits down with entrepreneur, investor, and award-winning employee benefits consultant Christopher  Hillier. Broadcasting from Denver, Colorado, Chris opens up about navigating the beautiful chaos of raising five kids, building businesses, and staying anchored in gratitude—even when life feels messy. With a background in employee benefits and risk management, Chris shares lessons from starting and acquiring multiple businesses, why he’s always had the entrepreneurial bug, and how he uses optimism and curiosity as tools for personal and professional growth. For leaders who juggle business, family, and everything in between, this episode is a heartfelt reminder that joy and challenge often go hand in hand.

Chapters:

• 00:00:00 - Welcome to The Eternal Optimist: Meet Chris Hillier
• 00:00:36 - Joy in the Mess: Finding Positivity in Chaos
• 00:01:36 - From Parker, CO to Purpose: Chris Hillier’s Origin Story
• 00:03:10 - Bitten by the Bug: When Entrepreneurship Called
• 00:05:40 - Building Companies, Raising Kids: The Family Startup Equation
• 00:12:45 - Chaos Meets Clarity: Balancing Business and Parenthood
• 00:14:53 - Creating Space to Think: Time, Energy, and Awareness
• 00:22:30 - The Time Trap: Why Most Leaders Are Overwhelmed
• 00:23:11 - Track It or Lose It: The Power of Time Logging
• 00:23:59 - Let It Go: Delegation and Automation that Actually Work
• 00:25:08 - Life Integration: Where Personal and Professional Meet
• 00:30:26 - Growth by Reflection: How Feedback Shapes Us
• 00:37:43 - Leading with Heart: Service, Empathy, and True Impact
• 00:39:17 - One Last Drop of Wisdom: Closing Thoughts & Tools
• 00:41:11 - Lightning Round: Books, Music, and What Inspires Chris
• 00:43:19 - What Is Eternal Optimism? Chris’s Definition

Links And Resources:

• Christopher on LinkedIn

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