Episode 20 | Greg Slamowitz

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, Will and Rich’s guest is Greg Slamowitz, an accomplished entrepreneur, investor, educator and author whose journey embodies the evolution from command-and-control to inspired, people-first leadership.

Greg began his career as a tax lawyer before co-founding Ambrose Employer Group, which he bootstrapped with $95,000 and grew into one of New York’s fastest-growing companies. Under his co-leadership, Ambrose became recognized as one of the city’s best places to work before its sale to Trinet and General Atlantic for $200 million. Along the way, Greg won 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, the turning point when he realized brute force wasn’t sustainable, and the paradigm shift that came from Jim Collins, Vern Harnish, and Maslow. He reflects on navigating the dot-com crash, codifying and enforcing core values even when difficult, and why true leadership means helping others rise to the top of the pyramid. We also explore his belief that sustaining leadership requires sustaining yourself — through wellbeing, balance, and joy outside of work.

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.