Inspired By Example: Greg Slamowitz on Flipping the Pyramid

Presented by Alignd, Inspired By Example is a podcast about the heart of leadership — revealing conversations with leaders across business, public service, education, and the military, asking five essential questions about who shaped them, what tested them, and what values ground them.

In this episode, we sit down with author of Flip the Pyramid: How Any Organization Can Create a Workforce That Is Engaged, Aligned, Empowered and on Fire, Greg Slamowitz. An accomplished entrepreneur, investor, educator, and author, Greg's leadership journey traces the evolution from command-and-control to people-first empowerment.

Greg began his career as a tax lawyer before co-founding Ambrose Employer Group, which he and his partner bootstrapped with $95,000 and scaled into one of New York’s fastest-growing companies. Under their co-leadership, Ambrose became a nationally recognized “best place to work” before its $200 million sale to Trinet and General Atlantic. Along the way, Greg earned Ernst & Young’s Entrepreneur of the Year award, founded a political action committee that helped pass the Small Business Efficiency Act, and authored Flip the Pyramid, a manifesto for empowerment-first leadership.

In our conversation, Greg shares:

• The anti-lessons of toxic early work experiences that shaped his philosophy.

• The turning point when brute force leadership proved unsustainable.

• How thinkers like Jim Collins, Vern Harnish, and Abraham Maslow reshaped his perspective.

• Lessons from navigating the dot-com crash and codifying core values — even when hard.

• Why true leadership means lifting others to the top of the pyramid.

• His belief that sustaining leadership requires sustaining yourself through balance, wellbeing, and joy beyond work.

Greg’s story is both entrepreneurial and deeply human — a reminder that leadership isn’t about control but about enabling others to thrive.

About the hosts:
Rich is co-founder of Alignd, an intuitive SaaS platform that simplifies how teams turn strategy into action. He's also a podcaster (The Age Old Question), a musician (The Sweet Remains), and a husband and father of five boys.

Will is founder of Next Frontier Capital, a VC firm headquartered in Bozeman, Montana. He’s passionate about supporting entrepreneurs to create companies of impact, utility, and value. He's an outdoorsman, a soccer fan, husband, and father of two sons.

This podcast is presented by Alignd and Next Frontier Capital.