Ashley Connell, CEO of Prowess Project joins Leaders and Legacies to unpack a bold truth: leaders don’t need another version of themselves. They need a “not you”—a skilled operator who thrives on structure, details, and execution.
Leaders & Legacies Podcast
Justin Dixon walked away from a comfortable six-figure job and launched a recruiting firm—just weeks before the world shut down. In this episode, he joins Craig Andrews to unpack what it really takes to lead when the timing couldn’t be worse.
Sonny Grappone didn’t follow a straight path to success. Raised by a single mother from Guyana and a hardworking Italian-American stepfather, Sonny grew up in Queens, New York, sharing a bed with his mom and sister. That early scarcity drove his work ethic—bagging groceries at 12, building...
Justin Jasniewski, CEO of Serve You Rx, breaks down one of healthcare’s murkiest corners—pharmacy benefit managers (PBMs). In this episode, he exposes how PBMs sit at the crossroads of drug manufacturers, employers, and pharmacies—often inflating costs instead of controlling them. With plain talk...
Milam Miller, founder of Be Confident and Kind and author of The Charisma Craft, joins Craig Andrews to challenge everything we think we know about charisma. A former executive for a billionaire sports team owner and affectionately nicknamed the “real-life Ted Lasso,” Milam shares how charisma...
Eli Portnoy, CEO and co-founder of BackEngine, joins Craig Andrews to expose the flaws in traditional customer feedback systems—and why leadership demands better data. A seasoned entrepreneur and Harvard Business School Executive Fellow, Eli dives into how B2B companies often make strategic...
Donovan Pyle pulls back the curtain on an industry most business leaders misunderstand: employer-sponsored health care. In this episode, Donovan explains how companies are overpaying by as much as 25%—often without realizing it—and why the current broker model keeps them trapped. Drawing on his own...
William Bissett, founder of Portus Wealth Advisors, joins Craig Andrews to unpack what it really takes to lead a company that survives and thrives beyond its founder. William shares how watching his father struggle in solo practice shaped his commitment to team building. His insight is simple but...
Brian McRae walked away from a comfortable W-2 job to chase something more fulfilling—control, freedom, and impact. What followed was a leadership journey rooted in service. In this episode, Brian shares how he transitioned from the mortgage world to building a coaching and mastermind business that...
Kyle Schwarz brings clarity to what leadership really looks like. A U.S. Naval Academy graduate and surface warfare officer, Kyle shares how a blunt rejection from his blue and gold officer nearly derailed his academy ambitions—but ultimately became a catalyst for transformation. He didn't quit. He...