Back to Blog

Growing Through Life Together

“Everyone carries with them at least one piece to someone else’s puzzle.” – Lawrence Kushner

From the very beginning of Reboot, peer groups have been something we’ve worked very hard to bring into the world because of how peer groups have shaped our own lives. I’m thrilled our episode today is with people sharing how their peer groups have helped them in their roles, their organizations, and their lives.  But first I wanted to share a story as to why peer groups are so important to me.

In the spring of 2005, I was desperately trying to find my entrepreneurial “sea legs.” A new college grad and a new entrepreneur, I had just gotten a taste of what it means to start a business, sell a product, build a small team, and feel completely and totally overwhelmed. I had wild swings of fear, excitement, terror, self-doubt, and was absolutely positive that everyone else had it figured it out, and I didn’t have a clue what I was doing and where I was going. And I felt incredibly alone.  And then I found my Tuesday evening group.

Through a random series of events, I met Jason, Lee, and Zak.  All of us were young entrepreneurs, fresh out of school, and full of optimism and self-doubt. But we had tons of energy, and lots of ideas to support the growth of each other’s businesses. And we had each other.

Tuesday night at 7 pm was our space and time to connect with each other, people who knew so well the ups and downs, the wins and losses, the weight and despair and the challenges that we all faced each day. There is simply nothing like having a safe space with others who know EXACTLY what you are going through and the weight that you carry. There is nothing like a safe space where you know you will be fully heard and understood and a space where you can listen and connect to others more deeply. Tuesday night was my space and time to be reminded: the weight was real, and I wasn’t alone in shouldering it.  

I found that group at a time when I needed help as an entrepreneur, but it turns out I needed them even more in my life.     

As I’ve mentioned before on the podcast, in October of 2005, my mom’s battle with breast cancer went from a thing we were dealing with in our lives to something ending hers.  We found out the cancer had spread to her brain and the time was short. And those guys were there for me as I dropped everything I was working on and headed home. They were there as I went through the true challenges of being with a loved one as she died.  And they were there in the months after her death where I struggled through the grief, struggled to find a meaning, struggled to find a new way, any way, forward.  

Beyond everyone and especially great leaders and entrepreneurs are great peers and loved ones, people who not only accept their wholeness but call it forth. The leadership and entrepreneurial path simply can’t be traveled alone. For me, I went looking for a group to help me be a better entrepreneur, to give me the answers to my painful challenges, and instead, I found a group of lifelong friends that gave me connection, strength, and resiliency to face whatever life threw at me.  The way to be a better entrepreneur or leader is to be a better human, and one path to becoming a better human is to have good friends who support you and mirror your blind spots.

In our podcast episode, we’re sharing with you all today, you’ll meet four CEOs and hear them talk about their peer group experiences. And how their time in those groups, like for me, have become a space to be supported and continue their own growth as leaders and as humans.


Embracing Leadership as a Reluctant CEO This essay is written by one of our first alums from our CEO Bootcamp, Sooinn Lee, CEO of LocoMotive Labs. Last fall, Sooinn also spoke at TEDxBayArea Women in a…
Connect. Think. Lead. Adapted from the forward I wrote to a friend’s new book… Connect. Think. Do. I’d first gotten the call, an inquiry call for coaching, two weeks previous. In a follow-up…
Up and to the Right I have a chai; he has a cappuccino. We sit outside, at the metal mesh patio tables, as the coffee house is about to close. “I can’t decide the path:…



The Reboot Podcast with Jerry Colonna, Team Reboot, and Startup Leaders

Check out the episodes

Social Media

Follow us on:


Follow our Medium publication for reflections on leadership and resiliency.

Subscribe to Medium