From Entrepreneur to CEO and Beyond

These past few months I’ve been tapping a new generation of leaders to step up to the helm, so I’ve thought a lot about leadership and what I’ve learned about it on my journey.

When I started my company back in 2004, I was like many entrepreneurs that I see today: I was the designer, the programmer and the ideas guy. I called the shots and measured the results. I made incredible mistakes, but I was accountable. I paid the bills on time and invested everything back into the business. I kept innovating and never gave up.

Then I learned what real leadership was about.

Real leadership is transformational.

Leading from the Shadows

I started empowering people and finding ways I could be of service. I stood back and let people discover their own strengths. I stepped back into the shadows and let them dig down deep to find the answers. What I learned surprised me.

People often won’t learn from their own mistakes if they aren’t able to own the process. When you let people go through their own learning curve, they begin to grow. And when you begin to grow people, you grow the company.

Growth without leadership is impossible.

My superpower became a kind of invisibility. This is very different from abandonment. I was there, agonizing over the struggles my team faced — spiritually engaged but physically absent. Because I was silently but actively involved, I knew the critical moment at which to send an encouraging word or resource or to point to a valuable tool.

I often learned more by just observing than I ever could have learned by attending meetings and having endless conversations. Employees would meet me and not have any idea who I was. From a distance, I empowered and affirmed my best people. Everyone was more productive, engaged and accountable.

I finally understood Lao Tzu, the ancient Chinese philosopher and poet, when he said, “When a good leader is finished, the people think they did it themselves.”

But bringing out the best in people and leading them to trust themselves doesn’t mean turning your back on them. Leading from the shadows doesn’t mean walking away; it means letting people do their part. It means trusting them.

In reality, collaboration only seems effortless. Like a leaderless orchestra, group leadership only works when every musician knows the piece intimately, trusts their fellow musicians and has learned how to test the creative limits of their instruments. Someone else has to write the music and inspire the musicians to perform at their very best.

Now I’m at the end of my CEO journey. Today I resigned as CEO. I built several multimillion-dollar companies that funded and sustained their own growth. After a good decade of serving countless employees over multiple companies, my work is done.

We did it.

Beginning Again

It’s the beginning of a new era and a new generation of leaders who will build on what we’ve done.

To begin, I’ve tapped Ryan Chartrand to lead the charge in disrupting developer resourcing. Ryan is insanely talented and knowledgeable. He’s hardworking. He knows exactly what value he brings to the company and what he expects to get out of it. He’s the kind of guy who you can let pick his own salary, and it doesn’t increase a dime until he feels he’s earned it. Thank you Ryan.

I’m excited to have Ryan take the lead, but I won’t be managing him. One of the insights I’ve distilled is how to mentor new leaders by having the team keep them accountable.

Each year the team will vote on the new CEO. This way I can focus on encouraging and empowering Ryan and the others as I transition into my new role.

Over the next few months, I’ll be inviting new leaders to join Ryan in his CEO journey. I’m going to be unpacking more of my understanding of leadership and the insights I’ve gained.

I don’t know everything the future holds, but I’m excited to be working at developing better models of business and leadership that can challenge and disrupt what isn’t working in the world. Where before I had focused on developing teams, now I’m turning my concentration to building and supporting new models for companies in the market.

I recently became a father, so this challenge is more personal than ever. When I was five years old, my Sunday School teacher asked us to write down what we wanted to be when we grew up. I wrote “a Dad.” Three years ago, that incredible journey began when my son came into the world. In a few weeks from now, his sister will join him.

Parenthood is an amazing adventure and an amazing responsibility. I have been thinking more than ever about what kind of world we have made. I’m keen to focus on the problems of the future generations. I lay awake at night wondering what kind of challenges they will face. Like every father from the beginning of time, I want my child to grow up in a better world. I don’t yet know what I will bring to it, but I am drawn to this space and feel passionate about being a part of building that better world.

Each of us has a part to play in a larger orchestra that stretches out beyond our own lifetimes. Our personal journeys can play original themes and movements in the symphony that will shake the world.

I can’t wait to begin again.