The CEO I could not help
One reason I coach is that there was one leader I loved but could not help.
A long goodbye
I walked into the hospital room. My dad was laying there in the bed: a faint version of his prior self.
For much of my life, my dad loomed huge in my eyes.
He had grown up a sports star in our small Michigan town. In adulthood, he married a beautiful woman, fathered two children, and built a successful business. To most outsiders, he had had it all. But his life had fallen apart.
Now, he lay paralyzed in a dimly-lit hospital room.
A year prior, likely during one of the late-night alcohol binges to which he was prone, he had fallen down the stairs in his condo.
He had spent the last year in this hospital bed paralyzed from the neck down.
There were glimmers of hope that he might heal. That he might walk again and find his way back to independence. But they proved unfounded. As I walked into the hospital room this day, I knew it was one of my father’s last.
My 4-year-old son, Marco, was with me. I have a beautiful photograph of Marco standing on the hospital chair, leaning over my father’s bed, telling him stories about his 4-year-old life.
The photograph is beautiful…and heart-breaking.
My father died a few days after I took that photo.
What motivates the work now
Today, five years later, as I consider what motivates the coaching, writing, and speaking I do, I see it is greatly motivated by the years I bore witness to my dad’s pain.
When I coach, I try to be the coach I wish he would have had. When I write, I write something I wish he would have read.
I wish he had known there was another way open to him.
My father grew up in a time when men were taught they needed to deal with life’s problems in isolation. Leaders, more than most, needed to suffer alone. Vulnerability, self-doubt, and uncertainty; these experiences had no place in the public or social persona of a leader.
That is how my father lived. And it ate him alive.
He self-medicated with alcohol and other drugs. That self-medication would take his health, his mobility, and soon thereafter his life.
My father died five years ago at the age of 65. His death brought with it a finality that shook me.
We’d never been close, but he had always been there. As long as he was alive, there was hope things in our relationship might change. When he died, it was less the man I mourned and more the hope for how my relationship with that man might one day finally blossom.
It never did.
There were many layers to my father’s demise, but a big one was isolation. He suffered alone. Through adulthood, through love, through family, and through entrepreneurship.
I began my own founder journey in a place closely akin to my father’s approach. Thanks to the grace, patience, and helpful instruction of many people around me, I found a path out of that isolation and into a way of living and leading that incorporated who I am with what I do. And I believe that evolution saved my own life, my family, and my relationship with my own son.
A new way available to us all
When I was starting out as a first-time founder, I read every book I could get my hands on about business, startups, fundraising, hiring, product design, and marketing. There are a lot of great resources out there for would-be entrepreneurs, creators, and leaders. But I didn’t find anything inviting me to bring my humanity to my craft: to leave my mask at the door and lead from a place that was truly me.
No one told me I could invite those around me into the humanity of my journey. Into my doubts, my fears, and the darkest corners of entrepreneurship and leadership. And those corners are some scary fucking places.
Nobody should sit in them alone.
Why I write
On the one hand, I don’t know who the fuck I am to write, speak, or coach. I am no Steve Jobs. No Mark Zuckerberg. No Elon Musk. I am just a man. An entrepreneur who has had more success perhaps than most but also much less than some. I am a husband and father who fails daily. The more I learn about adulthood, leadership, and love, the more I can see how much I still have to understand.
That self-knowledge and fear almost kept me from writing or coaching at all. While I haven’t built a global empire, I have suffered. I have stared into the eyes of failure, self-doubt, despair. I have lived through the burning down of my family life while my business stands at the edge of insolvency. And I’m ok with telling you about it. I cannot give you a map of how to build the next Facebook. But I can normalize for you the real, utterly human experience behind building something from nothing. And I can pull back the curtain behind the real struggle that perhaps more public figures are reticent to share.
I can paint my failures sharply, in full color, so that perhaps on your own journey you may dodge a few.
I do not think the world needs another business blog. But I do believe we need more examples of people sharing openly with one another the real human pain behind the journey. And I will commit here to do my best to deliver on that.
My own experience of the new way
The result of changing to leading from my humanity has been powerful for me. A few years into my last business, we were on the edge of bankruptcy.
As a part of my transition to a more open approach to leadership, and the related changes we made as a team to increase transparency, care, and efficacy, over the ensuing years, our revenue per employee grew from $55,000 to over $1M. We were a dying company that had laid off 80% of its workforce. But we hung on and became something great. Our employees and leadership cite their experience at Twenty20 those years as life-changing.
The changes we navigated together impacted the way each of us created, led, parented, and even embraced our families and friends.
A new way is needed
I believe there is a real, timely opportunity for us to re-think the way we lead and the way our organizations function. And I believe the resulting impact goes far beyond the walls of our companies and into the lives of our partners, children, friends, and communities.
When you take the place we spend most of our waking hours and turn it from a soul-sucking experience into a place that fosters humanity, you change people’s lives. You also, I believe, create higher-impact organizations: more impact, more profit, more opportunity.
If you find yourself at a point of realization that it is time to experiment with your own change, I would love to hear about it. Please reach out.
In the meantime, wishing you peace in your own journey.