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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WHO WE WORK WITH

Since 2014, Reboot’s Coaching and Team Experiences have met the needs of thousands of clients from seed stage to IPO, from bootstrapped to venture-backed to Fortune 100 and those who invest in them, from c-suite to solopreneur and leaders and managers across the globe, as well as artists and non-profits.

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.

“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 Union Square Ventures

HOW WE WORK

Many leaders turn to coaching when they seek to navigate complex challenges or seize new opportunities. Oftentimes, they’re looking to enhance their effectiveness, build stronger teams, or scale their organization. While these practical goals matter deeply, our decade of experience has shown that sustainable leadership growth requires more than just tactical solutions.

True leadership transformation emerges when you combine practical skill development with deeper self-understanding. When you learn to navigate your internal landscape—your doubts, fears, and aspirations—you discover a more authentic and impactful way of leading.

This journey of combining operational excellence with self-inquiry allows you to:

Show up as your most genuine self in crucial moments
Make decisions with greater clarity and confidence
Build more meaningful connections with your team
Lead from a place of purpose rather than just position

Our approach meets you where you are, addressing immediate challenges while creating space for the deeper work that sustainable leadership requires. Through this dual focus, you develop not just the skills to manage others, but the self-awareness and resilience to lead with lasting impact.

“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 Foundry Group

The Knowledge Project - Jerry Colonna

Rebooting Your Sense of Self

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WORKING WITH A REBOOT COACH

We believe that work does not have to destroy us. Work can be the way in which we achieve our fullest self.

Working with a Reboot Coach gets to the root cause of patterns and addresses what it takes to move beyond those patterns in order to grow. Clients call us in to address the underlying dynamics that keep individuals, teams, and organizations from the success they seek.

Our 1-1 coaching contracts are month to month and rates vary based on the length and cadence of sessions. A typical engagement is two 60 or 80-minute sessions per month with access to your coach in between sessions.

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"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 Former CEO of Twilio

WHAT IS COACHING?

Being CEO (or leader) is different than doing CEO, and it’s this subtle but significant understanding where coaching diverges from mentoring and advising. 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.

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 company, there is no blog post or book about the best ways for you to run your company.

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.

EXPERT COACHES, REAL WORLD IMPACT

Reboot coaches bring relevant context to bear on the coaching relationship. We understand human behavior and intra- and interpersonal dynamics, and the unique contexts of being an entrepreneur, founder, executive, or individual contributor, and VC in the world of startups, scaling/growth-stage companies, venture, and mature corporations.

We understand the unique challenges and opportunities that each of these groups faces, and we tailor our leadership development programs accordingly. We talk about the inner experience as much as the outer experience and approach the work as an inside-out journey of growth and development.

The Tim Ferriss Show - Jerry Colonna

The Coach with the Spider Tattoo

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MEASURED SUCCESS FOR OVER A DECADE

Since 2014, we’ve consistently seen that investing in human development yields remarkable business results.

The International Coaching Federation’s 2024 research shows that executive coaching leads to:

%

increase in individual performance

%

increase in team performance

%

increase in organizational performance

Your growth as a leader starts with your growth as a human being. We’ve perfected the art and science of helping leaders bridge this crucial gap.

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WHY REBOOT?

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.

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.

INVESTMENT IN YOURSELF, IMPACT YOUR TEAM

We believe better leaders make better humans, and better humans create more humane organizations and places of systemic belonging. We’re here to support you and your team members in bringing forth the best that you have, using everything that emerges from organizational life (both challenges and successes) as opportunities to grow. Discover Reboot Team Experiences.

“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 Former CEO of SoundCloud