Joe Massaro

“What’s wrong with you?”

It’s a question I heard all my life—first from the Catholic school nuns who taught me for a decade, and later from CEOs of major companies I worked with. I got used to it. I didn’t take offense. Honestly, I assumed plenty was wrong with me.

I struggled through school, never passing a grade until eleventh, when I finally discovered something I was good at: building. Looking back now, it’s clear I had an undiagnosed learning disability. With no guidance, I had to figure things out on my own.

But here’s what I learned: thinking outside the box wasn’t an option—because I never had a box. Instead, I built a method rooted in persistence. Try. Fail. Try again. Fail again. And eventually—after enough “crazy, stupid, what’s-wrong-with-you” attempts—something would click.

This is the story of how being asked the wrong question helped me find the right answers.

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