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Finally, a Reality Show for Men

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One of the first times I told my story I was in prison. A facility used largely for protective custody called South Bay in downtown Boston to be exact. I'd been told not to wear jeans and to bring two forms of identification. After I was buzzed through one cell after another I finally passed two beefy-looking guards sporting crew cuts and handguns and entered a giant room to face sixty inmates (most of whom I later found out were gay prostitutes and pimps who would never have survived in the general prison population). I had on Armani slacks, a blue shirt, and black Gucci loafers. My talk was to focus on drugs and alcohol abuse. But looking out over the crowd of mostly black faces I wasn't sure I could get words out of my mouth. My heart pounded with fear.

When I was introduced the men with corn-rows and tattoos turned their attention to the lanky, blond ex-rower at the lectern.

"Hey Gucci Boy!"

"Wanna spend the night?"

I looked at my feet and then peered off into the distance. I saw one giant bunk room where all these men slept. Then I looked back at the plastic picnic tables in the center of the room where they spent their waking hours and were sitting whistling at me. I started with a moment when I should have died, the flipping of a car on the Massachusetts Turnpike. My voice has always been booming so even though I couldn't make eye contact I knew they could hear me. I recounted all the ways I had taken wilder and wilder risks in my life. How my risk-taking had paid off in terms of material possessions. But that I had always known the real crash, not just a car but my entire life, was coming for me.

By the time I told them how I lost it all and been forced, once and for all, to stare at myself in the mirror, the crowd was silent. They were listening. I told them I was just a few months into my new life but already things had gotten better. After half an hour I was done. I was drenched in sweat. Several inmates approached me to say how much they appreciated my coming and how sorry they were for what I had gone through. One even gave me a hug.

Laying in bed that night I felt euphoria at having reached across what had seemed an unbridgeable chasm. I still couldn't believe the inmates had felt compassion for me or gotten anything out of my story. But they did. Something had happened as I stammered on about kids and divorce and mistakes made. In a way my search for manhood really started the day I stood up with my Gucci loafers on and, against every instinct in my body, told the truth. I realized that despite all the external differences in circumstance my words had made a difference. It made those guys feel a little better and made me feel a lot less alone with my struggles.

Around the same time, 1998, I started a venture capital firm. During the day I built companies but before and after work I was still listening to men's stories. More than the telling I came to realize that listening to other men speak the truth about themselves soothed my soul. From tough guys in South Boston to high powered investment bankers downtown I never tired of listening. I sought the courage to continue to do the right thing and in each man's story I heard something I could identify with that gave me strength.

After a decade of hiring and firing CEOs, capital market booms and busts, and investors who rightly wanted to know how we were doing, I had burned out. I began to write magazine articles about musicians like Rage Against the Machine guitarist Tom Morello, scientists like stem cell pioneer Konrad Hochedlinger and athletes like Ray Allen, whose stories touched me in some way as heroic. I also wrote about normal guys, no less heroic, who no one had ever heard of but where trying to be good fathers or husbands. I found many right in front of me and others half way across the planet.

At one point my Wesleyan classmate Sebastian Junger (author of Perfect Storm) put me in touch with war photo-journalist Michael Kamber. I had to track Kamber down via satellite phone in a bomb shelter somewhere in Baghdad and later amidst various civil wars in Africa. I wrote what I thought was a very eloquent exposition to Kamber on why manhood is at a cross-roads in America. His responded that he agreed with my premise but despite all he had lived through and photographed, he had no answers. In fact precisely because of what he had seen he didn't feel capable of addressing the topic of manhood, even though it was all he thought about while watching men butcher each other. "Exactly," I thought to myself.

In the end, I started to share some of the essays that I had collected with my thirteen-year-old son Seamus. Those conversations with Seamus that convinced me that not only are men at a crossroads but boys are too. They are dying to know what it means to be a man. But the male stick figures presented by popular culture, often either Navy Seal macho or Two and a Half Men ignorant, confuse our boys. They are left with little to hold onto as they try to grow into men of substance and integrity.

Talking to Seamus I learned that even the most challenging of the essays I had written -- about war, sex, prison, addiction, death -- covers ground that he already has exposure to and is really trying to figure out. Seamus has often expressed an interest in joining the military. But our conversations never got much past Jason Bourne. I told him to read one of Michael Kamber's essays and watch short film about him that a friend of mine had produced. The discussion we had afterward was completely different. For the first time we talked about what serving our country at a time of war really means.

In talking with Seamus I was reminded of what Kamber himself had said about not having answers. There is no singular way to be "good." When referring to a life or a man that word is purely self-determined. But certainly reflecting on the arc of my own life by listening to a wide variety of men's stories I was able to begin to get some sense of my own unique definition of a "good" man. That's really the only advice I had for my 13 year old boy. Keep asking the question and listening to men's stories to find you own path.

Photo: Stephen Sheffield Charles Street Jail #4

Photo: Stephen Sheffield "Charles Street Jail #4"

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