[Podcast Episode #14] Ready to Be Ruthless? Act Like a Renaissance Ruler

There’s a seductive trap in modern leadership—a desire to be liked more than to be effective. We hide behind endless meetings, polished slides, and layers of protocol, all while evading the very decisions that will determine the future of our business. We forget that leadership is not a popularity contest; it’s the art of creating stability and growth amidst chaos.

Cosimo de’ Medici understood this. Though never officially titled ruler of Florence, he influenced kings and popes from behind velvet curtains. His secret? He made the bloody decisions.

Let me take you there for a moment.

The city of Florence was a furnace of ambition—merchants clashed, families feuded, and power never sat still. In this firestorm, Cosimo moved with clarity. He knew that influence was built not just through charm and culture, but through courage in decisive moments.

In my book Get Your House in Order, I talk about the Palazzo della Signoria—the House of Influence. One of the rooms in this palazzo is dedicated to a principle I had to learn the hard way: Make the Bloody Decisions.

You know the ones I mean. Firing someone who no longer fits. Cutting a product line that drains your focus. Walking away from a partnership that once made sense but now holds you back. These decisions aren’t cruel—they’re necessary. Not making them poisons the well for everyone.

Too many business owners, myself included, have wrestled with guilt over letting someone go. But leadership means protecting the whole house, not just one room. When you delay a needed decision out of fear of discomfort, you’re sacrificing your entire enterprise for the sake of avoiding a tough conversation. That’s not compassion. That’s cowardice dressed in empathy.

Cosimo didn’t wait for perfect clarity. He acted with limited information but rooted in sound judgment. That’s the mark of a seasoned leader—one who is willing to act while others hesitate. As I often remind my sons: hesitation in moments that demand action can be more destructive than a wrong step.

And this principle extends beyond people—it’s about how we manage time.

We’ve been conditioned to waste our calendars on one-hour meetings that could take fifteen minutes. We answer every ping, every call, every “quick favor” that lands in our inbox. Let me be blunt: your time is sacred. Guard it like Cosimo guarded the Medici bank vault. Be ruthless with your time, not because you’re callous—but because you know its worth.

In leadership, love without boundaries becomes indulgence. And discipline without warmth becomes tyranny. True leadership, like Renaissance art, is a balance of light and shadow.

What decision are you avoiding right now that you already know is right?

What conversation, if had today, would liberate you and those around you?

As a leader, your job is not to please everyone. It’s to protect the house. And sometimes, that means putting your fist on the table and saying: “Enough. This ends now.”

Don’t wait for the perfect time. It rarely comes.

Make the bloody decision.