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.

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 Amish Jani, a top-tier venture capitalist and founding partner at FirstMark Capital, one of New York’s most respected early-stage investment firms. Amish has played a key role in shaping the modern tech landscape, backing companies like Shopify, Frame.io, Pendo, and Gravie, among many others.

Recognized by CB Insights and the New York Times as one of the top 100 venture capitalists globally, Amish has also been named to Business Insider’s Seed 100 and 50 Most Important VCs in New York lists.

Beyond investing, Amish co-founded CloudNY, a premier summit for cloud CEOs, and leads the FirstMark Founders Guild, a private community of the city’s most promising entrepreneurs. His career reflects not just a sharp eye for innovation, but a deep commitment to founder development, long-term thinking, and principled leadership.

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.

Inspired By Example is a podcast about leadership — purpose, passion and pivotal moments that change a life of meaning. In this episode, Will and Rich's guest is Casey Sheahan, a renowned outdoor industry executive, someone who has had an uncommon impact on how we play in nature and how business can work to protect it. As CEO of Patagonia, Casey led the company through its most successful period and cites the company's founder, Yvon Chouinard, as his biggest mentor and influence in leadership.

Casey has held leadership roles at other influential outdoor brands including SIMMS, KEEN, Kelty, Merrell, Wolverine, and Nike.

Casey has dedicated his career to leadership and conservation in the outdoor industry, including through his work with the Conscious Global Leadership Institute.

We recommend our listeners check out a TED Talk that Casey delivered in 2011 on the links between responsibility corporate transparency, responsibility and profitability.

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.