May 5, 2026

Culture Starts With the CEO

Show Notes

Culture Starts With the CEO

Episode Description

In this episode of Sales & Cigars, Walter Crosby sits down with Mike Chaput of nSight for part one of a three-part conversation on culture, core values, and leadership.

Mike shares his entrepreneurial journey—from buying an IT services company at 24, surviving the dot-com crash, navigating bankruptcy, and rebuilding from scratch—to growing nSight into a $35 million managed IT services business with more than 140 employees.

The conversation digs into one of the most important responsibilities of a CEO: strategy and culture. Mike explains why culture is not a vague company concept, but the behavioral operating system that shapes every decision inside the business.

This episode is for business owners who have core values on paper—but want to understand whether those values are actually helping the company grow.

Episode Highlights

Mike’s journey from a failed first business to building nSight
The hard lessons learned from bad deals, bad leases, and misplaced trust
Why entrepreneurship often teaches through painful experience
How CEOs shape culture whether they realize it or not
Why strategy and culture are the CEO’s two biggest responsibilities
The “Becker rudder” analogy for leadership and organizational direction
Why a business reflects the actions and beliefs of its leader
How old motivations can help you grow—then eventually hold you back
Why personal growth is required for business growth

Key Themes & Takeaways

Your business reflects your leadership.
The company you have today is a result of the actions, beliefs, and behaviors that created it.
Culture is not accidental.
It is shaped by what leaders tolerate, reward, repeat, and reinforce.
The CEO has the greatest impact on strategy and culture.
Those two responsibilities cannot be fully delegated.
Growth requires personal honesty.
What helped you get to one stage may not help you reach the next.
Core values must connect to behavior.
Values only matter if the team can understand them, remember them, and live them inside the business.
Entrepreneurial pain can become wisdom.
Mike’s early failures became the foundation for better leadership, better decisions, and a stronger company.