My new (old) coaching business: Strong Back Open Heart

After about 2.5 years as a Reboot coach, I’ve decided to focus on building my own private practice. The catalyst for the change was largely a technical one (more on that in a moment). I step away from my official relationship with Reboot with nothing but love and gratitude for the entire Reboot team, particularly my dear friend Jerry. I use the word “official” because I will always feel a deep connection to Reboot and my friends there. All the words I said about Reboot in my blog post when I joined forces with them remain true. (And I’ll certainly continue referring clients to them when I’m not a good fit.)

Now, the “technical” part: with the passing of AB5 in California (the so-called “Uber law,” which stipulates that most contractors must become employees), the folks at Reboot decided to shift their relationships with coaches like me who had worked as independent contractors and transition to a smaller roster of coaches as employees. I’m in a phase of my career where being an employee isn’t the right fit for me, so I made the decision to focus on building my own business. The name of my coaching business is Strong Back Open Heart LLC. (It’s not entirely new — I established it in November 2017 as the umbrella for my work as a contractor for Reboot and a few private engagements.)

The name of the company is derived from my approach to coaching and leadership as I articulate on my new web site:

I believe “strong back, open heart” leadership is the key to building great companies. The strong back is represented by fiscal discipline, strong process, and accountability. The soft, open-hearted front are values, purpose, connectedness, and compassion. Organizations and people are at their best when they manifest both in equal balance.

You can read more about me as a coach and my coaching approach, which includes a few brief anonymized case studies of actual coaching engagements. I also built a directory of leadership resources with books and articles that have helped me as a leader over the years and helped my coaching clients (consider this in beta — it’s a work-in-progress). If you’re interested in working together, all the ways to connect are on my contact page.

Aside from continuing the work, I’m excited about running my own business. A big part of my excitement is that I’m doing something completely solo for the first time in my life. I’ve always been a part of other companies throughout my career and I built and led teams at companies of all sizes for 25 years. I spent my time as an executive constantly scaling and delegating and I enjoyed it. Now it’s fun to do that in reverse and I’m enjoying being the CEO, CFO, CTO, CMO, and executive assistant.

If you’re interested in working together, please do reach out.

A huge thanks to Simon Collison who was a joy to work with as my design partner on the web site and to Chris Shiflett at Faculty for making the introduction to Simon.  

Becoming a Reboot CEO coach

I’m really honored and excited to announce that I’ve joined forces with my friends at Reboot and am now a CEO coach and facilitator under their umbrella. Reboot is helping shape the next generation of leaders who are reimagining the way business is done and I deeply identify with the vision. Jerry Colonna is a co-founder of Reboot and has been my coach since the summer of 2011, when I stepped into the CEO role at Etsy. When Jerry started coaching me back then, he was more or less a solo operation. Jerry reached a point where he wanted to scale his vision for coaching but realized he needed to build an organization to do that. I was honored to witness Jerry conceiving of Reboot and scaling it with his equally amazing co-founders. Jerry and Reboot have life-changing impact on the lives of entrepreneurs as evidenced by some of the testimonials and this beautiful portrait of Jerry and his work in Wired. Working with Jerry and Reboot has definitely been a life-changing experience for me and very much shaped my high-level philosophy on leadership as stated in my Reboot bio:

I believe “strong back, open heart” leadership is the key to building great companies. The strong back is represented by fiscal discipline, strong process, and accountability. The soft, open-hearted front are values, purpose, connectedness, and compassion. Organizations and people are at their best when they manifest both in equal balance.

I’m profoundly honored to be coaching under the Reboot umbrella and to have the opportunity to help and support CEOs in their leadership journeys. (Yes, I used the word “honored” a lot above because I truly am!)

With that bit of news out of the way — what is “coaching” anyway? Doug Silsbee’s book The Mindful Coach: Seven Roles for Facilitating Leader Development offers a simple definition that I really like: “any relationship where you are interacting with another person in service to his or her learning, growth, and change.” Being a CEO can be absolutely insane all by itself and Jerry helped me deal with the pressures of the roles during a period of extraordinary growth and change at Etsy, from chaotic startup to public company. But it wasn’t just “business.” During my time as CEO of Etsy, my wife and I adopted a child and I became a father. The coaching experience was highly integrated, meaning that it took my whole life into account. The same heart and soul that you put into being a CEO are the heart and soul you put into the rest of your life and relationships. As much as our culture demands the separation of “personal” and “business,” they are fundamentally integrated. Thinking of them separately means “dis-integration” and ultimately harms organizations and teams.

I see the work ahead as paying forward at least a small part of the generosity, care, and presence that I have received in being coached by Jerry. One Saturday morning last May, I got the call that meant my time at Etsy was over. My last day was Tuesday, just three days later. I hung up, stepped away from the phone, told my wife the news, and then immediately called Jerry. In the blur of the next three days, I was in regular contact with Jerry as all the logistics of my departure left little room for anything else. On my last night as CEO, Jerry came over to the Etsy office and we sat in the dark on the roof and talked. I don’t remember much of what we we talked about but I remember that Jerry was there and present for me during a difficult time. If I do nothing else in my role as coach, I hope to model the presence that Jerry taught me through his presence.

I am focusing on a very small number of high-impact engagements with my coaching practice. If you think I can be helpful to you, feel free to reach out or fill out the contact form over at Reboot and someone will be in touch.