Most Companies Are Stuck in AI “Pilot Purgatory” | Keynote Speaker Charlene Li

The Future of Affordable Housing | Christopher Alan Homes’ President & CEO, Ian Schmoyer

Ian Schmoyer didn’t originally plan to become a homebuilder. After years spent traveling the world surfing and figuring out his path, a turning point in his personal life pushed him toward entrepreneurship—and eventually toward building one of Florida’s fastest-growing homebuilders. In this episode, Ian reflects on his unconventional journey, the influence of his father, and the mindset shifts that changed his life. The conversation explores growth, maturity, purpose, and learning to lead under pressure. This is more than a business story—it’s a conversation about finding direction and building something meaningful.

Psychedelics Might Be the Future of Mental Health | Althea CEO, Niko Skievaski

From building APIs in healthcare to building a “psychedelic system of record,” Niko Skievaski has always been ahead of the curve. In this episode, he shares how his entrepreneurial journey led him into one of the most misunderstood industries today. He explains the stigma, the science, and the opportunity—and why now is the moment everything is changing. If you’re curious about the future of healthcare, this episode will open your mind.

Managing vs Leading | Executive Advisor Dr. Keith Dorsey

What’s the real difference between managing and leading? Most people think they know. Few actually do. Dr. Keith Dorsey breaks it down simply: management is execution, leadership is direction. But the implications go much deeper than that. In this episode, you’ll hear how leaders unintentionally hold their teams back, how culture shapes performance, and why clarity of role matters more than motivation. If you’re building a team—or trying to step into leadership—this will give you a clearer lens on what the job actually requires.

Most Companies Are Stuck in AI “Pilot Purgatory” | Keynote Speaker Charlene Li

Charlene Li has advised executives at some of the world’s most influential companies—and she sees a major leadership gap emerging around artificial intelligence. In this episode of Boundary Breakers, she explains the difference between knowing about AI and actually leading with it. Charlene shares why leaders must focus less on shiny tools and more on solving real business problems. She also discusses the cultural side of disruption: why organizations freeze when uncertainty rises and how strong values help teams move forward with confidence. This conversation blends strategy, psychology, and leadership wisdom into a powerful guide for navigating change. If you’re trying to figure out how AI fits into your organization’s future, you won’t want to miss it.

AI Governance Before AI Breaks You | CEO Matt Kunkel

AI is moving fast, and companies are scrambling to keep up…without blowing themselves up. Matt Kunkel explains why AI governance is about enabling innovation, not slowing it down, and how his customers are drowning in AI requests with no clear standard to follow. Brandon and Matt get into why this is a massive tailwind for risk and compliance, and why “guardrails” are the only way to scale AI responsibly. But this episode is also a founder story: leaving a million-dollar salary, bootstrapping at zero, Techstars, Jeff Weiner, and building culture that actually shows up in day-to-day decisions. You’ll walk away with a clearer picture of what it takes to build, raise, and survive.