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.



  • “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

  • "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

  • “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

We work with individuals, teams and whole organizations on professional and personal leadership development.

The main ROI of coaching is to have people not be confused, scared and generally freaked out. That translates into a huge boost in productivity and general well being. If there is lack of clarity around vision, roles, etc., or people are under large amounts of stress, your company is losing huge amounts of productivity.



If you are a company of…

5-8 people

Then every DAY of work is the equivalent of one WEEK of productivity.

20-30 people

Then every DAY of work is the equivalent of one MONTH of productivity.

250-300 people

Then every DAY of work is the equivalent of one YEAR of productivity.


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 fine-tunes the 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.

Case Studies

  • In 2011, Yesware founder and CEO Matthew Bellows found himself in an exciting but daunting position. The company, started a year earlier in Boston, was designed to help salespeople and sales managers work more efficiently. Yesware was freshly backed with top-tier venture capital and had tremendous potential before them.

    Amidst the excitement, Matthew was seized with fear. What if he and Yesware squandered all this potential? What if the company didn’t take advantage of this opportunity?

    Matthew Bellows

    Matthew Bellows

    CEO of Yesware

  • In early 2013, Bart Lorang was adapting to being a new husband and the leader of FullContact, a three-year-old contact software startup. At work, the company leadership was fragmented and reduced to loud arguments. At home things were unusually tense for Bart.

    Later, while speaking to Brad Feld, mentor and lead investor in FullContact, Bart confided: “I just don’t think I am nailing this whole CEO and husband thing.” That triggered an inflection point for Bart. He decided he had to become a better leader and family man. Brad suggested he contact Reboot.

    Bart Lorang

    Bart Lorang

    CEO of FullContact

Custom Program Design

From custom workshops for your team to complete leadership program design for your portfolio companies or organization, we can help design a pathway for professional development and sustainable success for the leaders you are invested in.



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 cofounders and helping them find their way back to the core beliefs that caused 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’s meant 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’s meant working with entire groups simultaneously and with the coach holding the container for the work, facilitating deeper understandings and communications.


Interested in working with a Reboot Coach? Fill out the inquiry form below.

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