Mark Sinatra on Embracing Vulnerability as a CEO

What does it take to step into the CEO seat—and stay there?

In Episode 29, host Matt Rosen sits down with Mark Sinatra to unpack the grit behind leadership. Mark reflects on when he first knew he wanted to be a CEO, the types of businesses he gravitated toward, and the hard truth that finding people who share your vision is rare. His advice? When you find those people—keep them.

Matt pushes the conversation deeper, asking Mark to share his most challenging leadership story. Mark opens up about building culture and relationships inside a remote company. While remote work has its advantages, fostering connection and alignment from a distance has been his toughest challenge yet.

At the heart of their discussion is what it means to embrace The Gritty Mindset: keeping an open mind, avoiding defensiveness, asking for help when needed, and creating a culture where leaders and team members alike feel safe to show vulnerability.

It’s a powerful reminder that grit isn’t just about pushing through—it’s about building trust, connection, and resilience in the face of challenges.