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 Hillier00:00:36 - Joy in the Mess: Finding Positivity in Chaos00:01:36 - From Parker, CO to Purpose: Chris Hillier’s Origin Story00:03:10 - Bitten by the Bug: When Entrepreneurship Called00:05:40 - Building Companies, Raising Kids: The Family Startup Equation00:12:45 - Chaos Meets Clarity: Balancing Business and Parenthood00:14:53 - Creating Space to Think: Time, Energy, and Awareness00:22:30 - The Time Trap: Why Most Leaders Are Overwhelmed00:23:11 - Track It or Lose It: The Power of Time Logging00:23:59 - Let It Go: Delegation and Automation that Actually Work00:25:08 - Life Integration: Where Personal and Professional Meet00:30:26 - Growth by Reflection: How Feedback Shapes Us00:37:43 - Leading with Heart: Service, Empathy, and True Impact00:39:17 - One Last Drop of Wisdom: Closing Thoughts & Tools00:41:11 - Lightning Round: Books, Music, and What Inspires Chris00:43:19 - What Is Eternal Optimism? Chris’s DefinitionLinks And Resources:Christopher on LinkedInThanks so much for joining us this week. Want to subscribe to Eternal Optimist? Have some feedback you’d like to share? Connect with us on iTunes and leave us a review!

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