Leading like “The Boss” in the age of AI

Leading like “The Boss” in the age of AI

Kevin Lee speaks with Andy Freed, CEO of Virtual Inc. and author of Lead Like the Boss, about what leaders can learn from Bruce Springsteen’s approach to performance, storytelling, and band leadership.

Andy explains that the book grew out of a single LinkedIn post he wrote after a Springsteen concert, reflecting on how Bruce’s on-stage intentionality could be applied to business. That idea evolved into a broader leadership framework built around a simple but powerful model: Think, Feel, Do. Before any communication—whether a keynote, Zoom meeting, or one-on-one review—Andy recommends deciding what you want your audience to think, how you want them to feel, and what you want them to do. He argues that most leaders skip this planning step and “go on stage hoping for the best,” instead of designing the experience as deliberately as Springsteen designs a setlist.

The discussion also explores how Andy applies this mindset in practice, including his long-running tradition of highly produced, humorous out-of-office vacation videos. What looks like a fun gag is actually a demonstration of how even mundane messages can become memorable brand touchpoints. Andy shares how he gets his team involved by making people feel safe, supported, and clearly directed, never just telling them to “be funny,” but giving them specific lines, context, and reassurance.

Kevin and Andy then widen the lens to cover differentiation in services businesses, reframing from task-based descriptions (“we answer your phones, send invoices…”) to impact-driven narratives about helping organizations “make their mark on the world.” They also talk about leadership through delegation, stretching team members with the right level of challenge, and the importance of appreciation, for both staff and clients.

Finally, they address the return of in-person events and the erosion of networking and personal branding skills in a post-COVID, remote-first, AI-driven world. Andy emphasizes teaching practical, manageable networking strategies and shifting the focus from trying to be interesting to being genuinely interested in others—a human advantage that becomes even more valuable as technology advances.