Why top performers struggle with insecurity
It sounds counterintuitive, but the higher someone has climbed, the more likely they are carrying a wound they've never named. Alex Gertsburg, attorney, entrepreneur, and founder of Cover My Six, has spent years thinking about this. His answer draws on Gino Wickman's Shine, Carl Jung's shadow concept, and his own therapy work: "That drive that has made us really successful has a dark side. The dark side is that we are probably trying to overcome something from our childhood." The ambition is real. So is the insecurity underneath it. Both are true at the same time.
The therapy session that changed Alex's life
About ten years ago, in the middle of a divorce and a fast-growing law firm, Alex sat down with therapist Jessica Horvat in Cleveland. She asked him to go back to his earliest emotional low. He landed on a memory from age four, a Jewish summer camp, a crying girl next to him, a teenage counselor yelling at him in English he couldn't understand yet, surrounded by a circle of kids. He didn't know what he'd done. He just knew he was terrified and alone. Jessica walked him through that memory in detail, then asked: "If that little kid was here right now, what does he need to hear?" Alex broke down. He said the kid needed a hug and to know everything was going to be fine. She told him to say it. That moment, he says, was the beginning of his real self-awareness journey.
Emotional intelligence for entrepreneurs: why it's the cheat code
Ben and Alex spend a significant stretch of this conversation on a question that doesn't get asked enough in business circles: why is emotional intelligence almost entirely absent from formal education? Alex's answer is both practical and a little cynical. Historically, math and science were prioritized because they drove economic growth. And today, getting parents to agree on whether schools should teach feelings in fifth grade is a political minefield. But the cost of ignoring it is enormous. "It is such an unlock to life. It's like a cheat code. And it is a trait that you will use for the rest of your life or abuse for the rest of your life." For entrepreneurs especially, the ability to regulate emotion, read a room, and lead with empathy isn't soft, it's the actual engine of sustainable success.
Core values and the integrity gap
Alex's four core values, walk in love, be here now, you be you, and the way knows the way, didn't come from a workshop exercise. They came from reading a decade of his own journals and noticing the same themes surfacing over and over. He's built a thinking tool around them and gives a talk called "A Checklist for Everyday Magic." The key insight: "The disparity between where you are and where your core values are is an energy drain." He calls it the integrity gap. Living out of alignment with what you actually value isn't just uncomfortable, it's exhausting. And most people don't even realize it's happening because they've never named their values in the first place. His advice: look at your calendar from the last year. That's your real values list.
How fear and ambition are connected
Ben shares his own framework, that fear and uncertainty are mishandled resources, and that on the other side of every fear is clarity and confidence. Alex builds on this: his unhealthy response to fear shows up as a quick flash of frustration, but he's learned to catch it. More often now, when a friend calls with bad news, his first internal response is "what a blessing", not because he's bypassing the emotion, but because years of self-work have rewired his default. The same drive that once came from wanting to prove himself has been slowly redirected toward something more grounded: living his values, being present, and trusting that the universe knows more than he does.
What authentic entrepreneurship actually looks like
For Alex, the clearest sign of his own growth is his Substack blog, Dispatch from the Bright Side. He writes about love, presence, authenticity, and trust, the same things he journals about every day, a habit he started in Iraq in 2003. "I actually don't care if anyone puts a like on this or not. I love the act of expressing what is inside of me in my own words." That's a long way from the young attorney who watched LA Law and wanted to be Corbin Bernsen because of the car and the jury arguments. The external markers of success are still there. But they're no longer the point.
