Reboot Your Leadership.

“Being” CEO is different than “doing” CEO and coaching is about helping you unlock the best way for you to lead. As you know there are plenty of blog posts and books about how to run a startup, but if that is all it took we would just buy the book and call it a day. Where it gets interesting and where coaches can help the most is actually working with you on your personal leadership style so that you can build the company you can run (and will enjoy running).

Know you're not alone. Join the conversation.

Inquire About Coaching


Become the Leader You Were Born to Be.

  • "Reboot's team of amazing coaches are world class at helping fast growth company leaders grow into their roles and develop leadership talents."

    Jeff Lawson

    Jeff Lawson

    CEO of Twilio

  • “Jerry, when he was my co-founder at Flatiron, taught me the people side of the venture capital business. And now as CEO coach to a number of USV portfolio CEOs (and many others), he is teaching the people side of the startup business to some of the best entrepreneurs we work with. He is a people person through and through and management is all about people.”

    Fred Wilson

    Fred Wilson

    Union Square Ventures

  • “I think a great CEO coach can be awesome and not-great CEO coach can be very detrimental. Jerry Colonna is the best CEO coach I’ve ever met or worked with. Reboot is the best organization for supporting entrepreneurs in all aspects of the entrepreneurial journey.”

    Brad Feld

    Brad Feld

    Foundry Group

  • “When other CEOs tell me how lonely it is at the top, I always advise them to find a coach like Khalid or Jerry. Having worked with both over the last few years, they have not only given me perspective and resilience under pressure, but kept my entrepreneurial fire burning to find new opportunities for Cheezburger. Having a trusted CEO coach should be part of the Standard Operating Procedure for every startup.”

    Ben Huh

    Ben Huh

    Founder of Cheezburger

  • “At SoundCloud we refer to Jerry as Yoda. He’s not only helped me develop personally as a CEO but we’ve been fortunate enough to have him coach, develop and inspire large parts of the SoundCloud leadership team. His impact on our entire company is deep and remarkable.”

    Alexander Ljung

    Alexander Ljung

    CEO of SoundCloud


Reboot was founded on the belief that in our work lies the possibility of the full realization of human
potential. Work doesn’t have to destroy us. Work can be the way we achieve our fullest selves, and in
doing so becoming more effective leaders, colleagues, and human beings. We don’t have to do it alone,
nor do we need to.

We work with individuals, teams and whole organizations on professional and personal leadership
development. Our client companies range in size and stage, from startup to IPO. Many of them are
high-growth, tech-oriented startups. We know startups, and we know the opportunities and challenges
that come with growing and leading a high growth organization.

In this OnBeing conversation with Krista Tippett, Jerry Colonna speaks to what we believe is possible for
bringing our whole selves to work:



The word “coach” has many meanings, so it’s important that we clarify our definition. First, here is what coaching is not. Coaching is not “advising” or “mentoring.” Advisors and Mentors are professionals who have gone through a similar experience and they support you with advice. Advisors and Mentors are an essential part of any business’s support network. However, being CEO is different than doing CEO and it’s this subtle but significant understanding where coaching diverges from mentoring and advising.

Coaching is about helping you unlock the best way for you to lead and build your company. While there are plenty of blog posts and books about how to run a startup, there is no blog post or book about the best ways for you to run your startup.

It’s for this reason that coaches can help make a substantial impact by actually working with you on enhancing your personal leadership style and within the subtle but essential nuances of your organization so that you can achieve your goals and build the best company
you can.

Coaching takes the set of mental models you are using to make decisions and unpacks them. It makes the unconscious conscious so that you can decide what outcomes you would like. It then helps you fine-tune your mental models so they produce those results. Coaching is about getting better outcomes with less effort. It makes new actions available by changing you, the observer.


The main ROI of coaching is to have people not be confused, scared and generally freaked out. A clear mind means that tasks and collaboration can happen more easily. That translates into a huge boost in productivity and general well being for each individual and the organization. If there is lack of clarity around vision, roles, responsibilities, or people are under large amounts of stress, your company is losing huge amounts of productivity.

What’s the Measurable Impact of Coaching within an Organization?
If you are a company of…


people then every DAY of work is the equivalent of one WEEK of productivity


people then every DAY of work is the equivalent of one MONTH of productivity


people then every DAY of work is the equivalent of one YEAR of productivity

Our case studies speak to this as well:

Get the most out of your coaching experience

Wondering what to expect from the coaching relationship? Looking to better understand Reboot’s approach to coaching? Our Introduction to Coaching document is designed to help you get the most out of your coaching experience.

Learn More


You fit the mold of a Reboot Client if you…

  • Feel the need to address the problems in your leadership that seem to repeat themselves time and time again.
  • Can’t see clearly why you’re struggling.
  • Want to really understand how you’re being complicit in creating what you say you don’t want.
  • Want to explore how that which has gotten you here, may be keeping you small now, and if it’s time to change.
Our clients are ready to transform their lives and leadership. They…

  • have a willingness to explore their own agency in bringing about change in their lives.
  • realize that living by everyone else’s rules and ideas is not going to scale, and they want to start leading from within (while paying attention to the lessons of those that have gone before them).
  • often come to us when they are exhausted and depleted, and they are beginning to see that in order to scale themselves and their organizations they will have to become a different type of leader.
  • care about more than just financial metrics–they hold a bigger frame when it comes to the concepts of success and what constitutes a well-lived life.
  • are ready to do the work of self-actualization and traverse all the hills and valleys in the process. They are willing to be open and vulnerable and to explore their unsorted baggage.

  • are interested in the root cause of patterns and understand how it’s important to break those patterns in order to grow.
  • are eager and ready to explore their own perspective and are deeply curious and are open to looking at things in different ways.
  • want to talk as much about the inner experience as they do with the outer.
  • are interested in learning about themselves and how they can think about building a stronger, more sustainable organization.
  • are self-aware, willing to go deep, to be emotionally vulnerable, to be curious, to be willing to visit the past with an open curiosity.


All of our coaching engagements are month to month and the investment varies based on the number/length of sessions and from coach to coach. However, a fairly typical engagement is 2 x 60-minute sessions per month or 2 x 90-minute sessions per month which include support on an as-needed basis.


In addition to supporting you with coaching, we also offer a suite of complementary services to enhance your coaching experience. Should you be interested in any of the following, let us know and we’ll be happy to explore how they might be helpful to you and your team.


One of the most satisfying moments is when team members finally get each other and the work between them becomes less of an effort. Coaching often begins with a focus on individuals and their moments of stress, their times of existential challenge, their crucible times when who they are mixes with what they do to be heated by the fires of what they believe. But to really be of service to individuals, especially leaders first facing the rigors of leading, we support entire teams.

Sometimes that means navigating between co-founders and helping them find their way back to the core beliefs that caused them to go into business together in the first place. Sometimes that means extended, consistent work with whole leadership teams, helping them co-create safe, meaningful containers for their work; helping the entire group thrive.

Coaching partners and teams requires an expanded set of skills. Sometimes it requires conflict resolution and mediation. Often it means helping people to relearn basic listening skills.

The style of work varies depending on the team’s needs. For some, it means a steady one-on-one presence with a series of individuals at the same organization, enabling the process to benefit from the multiple perspectives that can be shared. For others, it means working with entire groups simultaneously and with the coach holding the container for the work, facilitating deeper understandings and communications.

Coaching Inquire

  • We respect your privacy and will respond via the email you’ve provided within 2-4 business days.

  • We've been having some technical issues with our form that we're in the process of working on. If you have issues submitting an inquiry, please email your responses to

    Please select all that apply.

Our Services