Reboot Your Leadership.

Being a Leader is different than “the doing” of leadership 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).

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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 become 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. We help our clients develop the skills and knowledge they need to be effective leaders, regardless of their stage in life or career, so that they are better able to navigate the ups and downs and inevitable transitions inherent in one’s personal and professional growth.

We work closely with high-growth, tech-oriented startups, but also support solopreneurs, small business owners, organizations in the non-profit space, and individuals undergoing transitions. We understand the unique challenges and opportunities that each of these groups faces, and we tailor our leadership development programs accordingly.

We believe better humans make better leaders and better leaders create more humane workplaces. We know that the work to become a better human affects one’s life personally and professionally.

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


More than any particular role, industry, or type of organization, what characterizes Reboot clients is their recognition that the experience of work is not separate from their experience of life as a whole; rather, they are interrelated and interdependent.

Challenges and opportunities in the professional realm are what lead clients to pursue executive coaching. Many of them may initially hold a belief that if they could just figure out how to do the job better then they’ll feel better.

We believe the opposite is true. That is, if you can learn to manage your psyche, your anxieties, and the sensation of failing, then you can be a leader. And the leader who commits to this work is more likely to show up to others as authentic and trustworthy.

We believe that helping clients develop the managerial skills necessary to do the job is important but not enough to create the transformation they are seeking. To be a leader, they must also cultivate a fearless willingness to look deeply through self-inquiry.

Here are some additional characteristics commonly exhibited by people who make great Reboot clients…

  • Are open to approaching the work as an inside-out journey of growth and development.
  • They are willing to speak honestly about the things that are not working in their life and work. 
  • They’re open to learning, listening, being wrong, seeing things in new ways, and trying new behaviors. 
  • They take ownership of their own experience and seek to be the driver of their own change. 
  • They are willing to put in the work in order to grow. 
  • They see coaching as an investment

  • 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.

Here are some signals that may indicate a person is not a good fit for Reboot coaching:

  • they are coming to coaching looking to discover or be told the “right way” to lead and are not open to asking themselves the big questions and leaning into finding their own answers. 
  • they are approaching coaching transactionally–looking for what will lead to a quick fix. 
  • they are motivated primarily by external outcomes like money, influence, power, etc. 
  • they are focused more on blaming or “fixing” the behavior of those around them, instead of looking at their own agency. 
  • they are coming to coaching primarily to satisfy the expectations of someone other than themselves (a supervisor, investor, co-founder, etc).


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.

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