What if the values that made you who you are — resilience, service, empathy — could become the operating system for an entire organization? Today's guest grew up in Hialeah, Florida, the son of Cuban immigrants who arrived in America with almost nothing and built everything through grit, integrity, and an unwavering belief that hard work is the price of admission. He lost his father at 12 years old, found his footing in the U.S. Army — where he'd eventually jump out of planes at night as part of an Airborne unit — and then quietly built one of the most storied careers in the travel industry. David Herrera served as President of Norwegian Cruise Line, where over more than a decade he helped transform the company's commercial operations, led its expansion into China, and championed a genuine, veteran-driven military appreciation program that earned him letters, mugs, and thank-you notes from guests whose gratitude had nothing to do with the bottom line. But what strikes you most about David isn't the titles or the milestones — it's that he leads the same way his mother lived, the same way his Army sergeant Mahoney taught him: from the front, with his word as his bond, leaving no doubt whose side he's on. In this conversation, we talk about growing up in a Cuban immigrant household that embodied the American dream, what the military teaches you about trust and team that no MBA program can replicate, how he thinks about culture not as a poster on the wall but as the answer to the question — who's winning here, and why? — and what it really means to be a servant leader when the stakes are high. In this episode we discuss: Hire your manager, not just your job. The person above you shapes everything about your early career experience. Choose them wisely. If you're not early, you're late. Punctuality is ultimately about respect — for other people's time and for the commitments you make. Share the victory, own the setback. When things go right, celebrate the team. When things go sideways, step forward and take responsibility. Culture is what gets rewarded. Not what's written on the wall — but who's winning in your organization and what it is about them that you actually respect and want to replicate. Treat everything as a learning opportunity. Doesn't matter if you're painting parking lots in Miami heat or running a division — be in the moment, observe what works, and study what doesn't so you can avoid it. Lead from the front. Never ask someone to do something you haven't done or aren't willing to do alongside them. That credibility is the foundation of real trust. Know your foxhole friends. Who in your life both genuinely cares about you and is capable of showing up when it counts? That combination is rarer than most people realize. Sometimes the right business decision comes at a personal cost. Separating emotion from judgment is one of the hardest and most important skills a leader can develop — and it never fully stops stinging.
