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What does it take to build a company that performs at the highest level, and stays human at the core?

In this second part of my conversation with Mike Chaput, CEO of Endsight, we go beyond values-driven culture and explore the disciplines, systems and operational rhythms that make an organization truly self-sustaining.

Mike’s journey -- buying his first business at 24 with borrowed money, failing, rebuilding, and ultimately creating one of the top-performing IT support companies in the country -- gives him a rare, grounded perspective on what “enduring success” actually looks like.

Today, Endsight is a 140-person company generating $35M+ in annual revenue with a 20% EBITDA margin, putting it in the top 1% of its industry. But the most extraordinary part? Mike built it through people-first leadership, relentless clarity on core values and a deep commitment to operational excellence.

In this episode, we explore:

  • Why memorable, clear, branded, and complete core values become the operating system of a healthy business

  • The RSVP values framework: Respect & Connect, Servant’s Heart, Value Value, and Progress Over Comfort

  • How Endsight hires for culture first, even before skills

  • Using lifeline interviews to uncover ethics, motivations, and alignment

  • Why avoiding a bad hire is more valuable than landing a good one

  • How constraints create freedom, and why discipline unlocks creativity

  • The rhythms, systems, and lean practices that operationalize excellence

  • How to build a culture where people naturally take ownership and solve problems

  • What leaders must understand about motive, followership, and sustainable influence

If you’re a founder, a CEO, or a leader who wants to build a company that outlives you, this conversation is full of gold.

📌 If this episode sparks insight or challenges your thinking, leave a question or reflection in the comments. This community grows through the questions we ask together.Like, subscribe, share, and most importantly… keep asking better questions.

Episode Show Notes and Deep Dive:📚 Deep Dive, Show Notes and Reference Reading: https://www.awayre.com/activate-company-culture-playbook/

Connect with Mike Chaput:🌐 Website: https://www.endsight.net🔗 Linkedin: https://www.linkedin.com/in/michaelchaput/🎞 YouTube Channel: https://www.youtube.com/@thechaputperspective

"The Business Philosopher Within You" Podcast:🎬🎙️📖 Website: https://www.awayre.com/business-philosopher-within-you-podcast/🦸‍♀️Be a Guest: https://www.awayre.com/business-philosopher-within-you-podcast-guest/

🤔 Podcast: The Business Philosopher Within You Podcast 🗓️ Published: 2nd & 4th Wednesdays📇 Episode: 34📜 Format: Full Episode📅 Date: November 26, 2025👨‍💼 Guest: Mike Chaput, Founder and CEO, Endsight🎙️ Host: Bhavesh Naik

CHAPTERS:

00:00 - Highlights and Introduction

02:35 - Creating an Executable Value System

09:31 - Core Values as Constraining Behaviors

15:16 - Hiring for Culture and Values Vs Skill

23:06 - Cultural Orientation After Hiring

25:54 - Operationalizing Company Culture

31:41 - Achieving 20% Profit Margins

35:49 - Non-Negotiables for Success

40:43 - Impact of AI on the Future

46:08 - Human Vs AI: Insights, Perspectives and a Prediction

47:24 - Darkest Moment Reflection

53:55 - Finding Peace and Inspiration

56:45 - Lasting Words of Wisdom and Getting In Touch

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Music by Yrii Semchyshyn (Thank You!): https://www.patreon.com/yuriisemchyshyn

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35 episodes