I talked to 300 of the world's greatest CEOs in one year

I interviewed 300 CEOs in the past year.

Adding it all up, I’ve spent close to a month immersed in conversations with some of the sharpest entrepreneurial minds alive; an outcome that is as unexpected as it is extraordinary for three very particular reasons.

First, let the record show that I am neither a journalist, nor do I aspire to be one. Sure, I thoroughly enjoy writing, and I regularly contribute to a number of publications from Forbes and Fast Company to TechCrunch. However, there’s something about the label of a journalist that doesn’t sit right with me.

Perhaps it's the fact that journalists write for a living, while people like me write to learn, and I wouldn’t have it any other way. And yet, here I am, compiling a booklet that distills what I learned from interviewing 300 of the world’s leading CEOs—doing exactly what a journalist might do, just without the Press badge or the trademark fedora. Go figure.

What is even more unexpected is that the project happened at all. This has been a year of profound change and transformation, overflowing with milestones that would stretch any reader's patience were I to list them all. My wife and I welcomed the joy of our third son, I gathered the resolve to leave Boston Consulting Group and build my own Vertical AI consulting outfit, and I embraced an ambitious teaching schedule at Harvard, Columbia, and NYU that spans more MBA and executive education classes than a typical clinical professor sees in three years.

Knowingly adding a daily regimen of three calls, plus breakfasts and dinners, on top of everything else would be nothing if not an act of insanity. But here’s the thing: I never made an explicit decision to start this project.

Instead, it grew organically from opportunities afforded to me by my earlier writing, which led to conversations with leaders most people would only ever admire from a distance. If Warren Buffett’s team offered a sit-down, the actually crazy thing to do would be not to take it, right?

Yet somehow it all felt entirely natural, to the point where I’ve never felt such a deep alignment between who I am and what I am doing. One man’s mid-life crisis; another man’s rocket fuel for launching into a life worth living, I suppose.

That isn’t to say that the three-calls-per-day schedule hasn’t been grueling, and at times impossible to keep up. What kept me going was a feeling that every calendar invitation and early breakfast meeting was a lottery ticket that was guaranteed to win, even though I never knew what I’d walk away with.

What I do know is that these conversations taught me more than decades of working as a brain-for-hire at the United Nations and Boston Consulting Group, or all my degrees combined.

And here we arrive at the final paradox: one that has little to do with me and everything to do with how flawed my earlier understanding of success has turned out to be, thanks to what I’ve learned from you.

After 300 interviews, I find myself grappling with the unsettling realization that I’ve unlocked my own Pandora’s box, cursed with the knowledge that there’s something profoundly wrong in how we frame success for doe-eyed MBAs and even the most seasoned CEOs.

What I’ve uncovered feels almost heretical—challenging not just what I’ve been taught about business, but also much of what I’ve been teaching others about the foundations of success.

Reviewing my notes, a striking pattern emerges: the stories of truly exceptional success aren’t built upon the conventional virtues of grit, passion, or perseverance alone. Instead, they hinge on three transformative strategies: the courage to quit when persistence becomes a liability, an obsession with questions that defy easy answers, and the audacity to embrace a rangeful life, transcending the narrow boundaries of specialization.

It’s a lot to unpack, and the only fitting place to start is where I began—by dissecting the gospel of success that we’ve all taken for granted.