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.
Audio Can You Scale Revenue Without Sacrificing Values?
Video Can You Scale Revenue Without Sacrificing Values? (Lessons from a CEO)
Click to play
About Mike Chaput
Founder and CEO, Endsight
Mike Chaput, Founder & CEO of Endsight, bought his first company at 24 with borrowed money and no experience, which led to early failure and bankruptcy, but also ignited a lifelong drive to understand what makes businesses succeed.
From those lessons, he built Endsight into one of the top-performing IT support companies in the country. Today, Endsight is a team of 140 people, generating $35 million in annual revenue, and serving over 400 clients with a 20% EBITDA margin, placing it in the top one percentile of its industry.
With degrees from Columbia Business School and UC Berkeley’s Haas School of Business, Mike blends top-tier strategy with real-world execution. As a founder and the CEO of Endsight, as well as a board member and trusted advisor to multiple high-growth companies, Mike brings a grounded, operator’s perspective to leadership, sustainable growth, and building resilient teams with purpose.
This episode is Part 2 of a two-part conversation...
Even though each episode can be listened to as on its own, you may want to check out Part 1 of the conversation, where Mike Chaput and I explored how leaders can build human-centered, values-driven cultures that scale.
In this second part, we turn to the other side of enduring success: the practical strategies and disciplines that make a company resilient over the long run. What does it really take to achieve sustainable growth, strong margins and financial health, without burning out yourself or your team?
"If living the values won't manifest your vision, then either the vision needs to change or the values need to change."
Mike Chaput
Founder and CEO, Endsight
Chapter-by-Chapter Summary
Following are the sections we covered in this conversation with their summaries, along with the time location in the video and audio to follow along. The timestamps in orange correspond to the chapters in the YouTube version of the podcast episode. This video will display to the lower right as you scroll down.
Note: Chapter Headings Contain Time-Stamps
The numbers that precede the headings (like 00:00) are the time-stamps associated with the video version of the podcast that's included above.
The Business Philosopher Within You brings a focused conversation between host Bhavesh Naik and guest Mike Chaput, CEO of Endsight, that cuts through leadership platitudes and gives practical direction on building a values-driven, operationally excellent company. The discussion moves from designing memorable values to hiring practices, operational rhythms, financial health, and the ways AI will reshape the playing field. Each segment offers a compact idea that leaders can test in their own organizations.
"We have a fundamental philosophy that great businesses have really high performing human beings, and those high performing human beings need great tools and technology."
Mike Chaput
Founder and CEO, Endsight
00:00 Highlights and Introduction
The conversation opens with a clear premise: great businesses are built by high-performing people who have the right tools and a culture that channels effort. Mike frames culture as both a strategic asset and a practical operating system rather than a poster on the wall. Expect concise, principle-first thinking that anchors the rest of the discussion.
02:35 Creating an Executable Value System
Mike explains how to make core values usable rather than ornamental. He outlines the need for values to be memorable, branded, and backed by layered clarity—short identifiers at the top with deeper belief statements underneath. This segment teases a simple technique for turning an ethos into a repeatable habit without drowning it in corporate jargon.
"You have to build this kind of culture where people are willing to constrain themselves to a process and then they're willing to do what the Japanese called kaizen."
Mike Chaput
Founder and CEO, Endsight
09:31 Core Values as Constraining Behaviors
Values work because they constrain behavior in productive ways. Mike reframes constraint as the fertile ground for creativity: boundaries create meaning, focus, and the dopamine of progress. The conversation explores why respect, dignity, and servant leadership matter as operational choices, not just moral positions.
"We stopped interviewing for skills in the beginning, and we started interviewing for culture."
Mike Chaput
Founder and CEO, Endsight
15:16 Hiring for Culture and Values Vs Skill
Hiring choices determine whether culture can scale. Mike discusses the trade-off between short-term technical needs and long-term cultural fit and shares how prioritizing alignment early avoids high-cost mistakes later. This section surfaces a distinctive interview approach used to reveal an applicant’s values and story.
23:06 Cultural Orientation After Hiring
Onboarding is where values either take root or fade away. Mike describes a hands-on orientation practice that treats new hires as cultural cohorts, not just seat-fillers—two-hour sessions, public recognition systems, and frequent touchpoints that externalize the company’s code so the team can follow it in practice.
"It's better to have a mediocre process that's followed relentlessly than a great process that's never followed."
Mike Chaput
Founder and CEO, Endsight
25:54 Operationalizing Company Culture
Culture without operational routines is brittle. Here you’ll find the practical levers Mike relies on: one-on-ones, managers who observe work in real time, problem registers, and weekly to quarterly rhythms that turn issues into strategic priorities. The emphasis is on a disciplined, iterative approach where a mediocre process followed consistently beats a perfect one that is ignored.
31:41 Achieving 20% Profit Margins
Financial performance and culture are not opposites. Mike makes the case that healthy margins enable investment in people, tools, and new services—so customers and employees both win. He explains why aiming for strong profitability is essential to building resilience and funding the next product or capability.
35:49 Non-Negotiables for Success
If the company ever needs a single anchor to preserve as it scales, Mike points to culture. The nuance is important: iterate culture when results stall, but hold it tightly once it becomes the platform that consistently produces the outcomes you want. This section clarifies when to change course and when to protect the core.
"I view AI as being more disruptive than broadband Internet."
Mike Chaput
Founder and CEO, Endsight
40:43 Impact of AI on the Future
Mike places AI among the most disruptive technologies he has seen and views it as both a challenge and an opportunity for IT firms. The conversation outlines why early adoption and internal experimentation will position companies to advise and deploy AI for clients, lifting value higher up the stack rather than competing on price alone.
46:08 Human Vs AI: Insights, Perspectives and a Prediction
Rather than predict wholesale job loss, Mike argues that AI will change the problems we solve and expand what’s possible. He predicts better access, lower costs, and new services delivered at scale—while acknowledging there will be friction. The tone is cautiously optimistic and focused on preparing teams to lead the transition.
47:24 Darkest Moment Reflection
Entrepreneurship includes painful setbacks. Mike shares candid stories of betrayal, bankruptcy, and sabotage that tested his resolve. His reflections concentrate on the leadership choice to remain transparent with a team and to keep trust as a core operating decision even when it risks being abused.
53:55 Finding Peace and Inspiration
Keeping perspective requires more than strategy. Mike talks about creative and somatic practices that restore focus—music, deliberate physical attention, and community. These practices are framed as practical ways leaders clear the mind and remain present for the work that matters most.
"Operationalizing excellence is, really a detail oriented thing, and it is really is cultural."
Mike Chaput
Founder and CEO, Endsight
56:45 Lasting Words of Wisdom and Getting In Touch
The conversation closes on gratitude and engagement. Mike recommends reading and structured learning as continual inputs for leaders, and he makes himself available on professional networks for those pursuing the same questions. The final remarks are an invitation to test ideas, iterate thoughtfully, and keep refining what it means to be a values-driven organization.
Key takeaway: When values are memorable, reinforced through routines, and matched with disciplined operations, they become the platform for sustainable growth, resilience, and meaningful innovation.
Further Reading About Growing through Values and Culture
Built to Last by Jim Collins and Jerry I. Porras
Mike references "Built to Last" when discussing the importance of iterating company culture until it aligns with desired results. He draws on insights from the book to emphasize the need for a strong cultural foundation as a platform for sustainable growth.
The Motive by Patrick Lencioni
Mike Chaput highlights "The Motive" as a required reading for leaders at Endsight, emphasizing the importance of servant leadership in fostering a culture where team members are empowered to serve customers and each other effectively.
The Anxious Generation (Corrected to The Coddling of the American Mind) by Jonathan Haidt
(Note: This book title seems to be incorrect or not widely recognized. Jonathan Haidt is known for "The Coddling of the American Mind" and other works.)
Mike mentions Jonathan Haidt's work in the context of discussing the disruptive effects of social media, particularly on young people. He contrasts this with the potential positive impact of social media in spreading valuable ideas and fostering engagement.
Insights on Scaling a Business with Values, Vision and Aligned Execution
- Culture-First Approach: Building a resilient and successful business starts with a strong cultural foundation. By prioritizing culture over skills in the hiring process, companies can ensure that their teams are aligned with core values and are more likely to contribute positively to the organization's goals.
Operationalizing Culture: To truly embed culture within an organization, it must be operationalized through regular meetings, feedback loops, and recognition of core values in action. This ensures that culture is not just a set of ideals but a living part of daily operations.
Embracing AI: Artificial Intelligence is seen as a major disruptive force that can transform business operations. Companies that proactively integrate AI into their processes can offer more value to customers and stay ahead of industry changes.
Resilience and Transparency: Effective leadership requires resilience and transparency, especially during challenging times. By maintaining open communication and trust within the organization, leaders can navigate setbacks and foster a supportive environment.
Sustainable Profit Margins: Achieving and maintaining strong profit margins is crucial for business growth and innovation. A financially solvent business can invest in new technologies and practices, benefiting both employees and customers.
Article Creation Process
This article was created with the help of Artificial Intelligence from a live, recorded video conversation between Bhavesh Naik, Host of "The Business Philosopher Within You podcast" and Mike Chaput, Founder & CEO of Endsight.
While AI's help was sought for many aspects of the article, the structure of the article, driven by the creation of the index, is mainly a human process that requires significant natural intelligence and input.
