Better humans make better leaders.

We believe…

Practical Skills
+ Radical Self Inquiry
+ Shared Experiences

= Enhanced Leadership + Greater Resilience

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This formula is behind all that we do.

We’ve designed our offerings to reboot your leadership whether you’re a CEO, founder, c-suite or employee.
Together, our offerings are a complete foundation for what it means to emerge as a leader. We offer coaching, 360 degree performance reviews, bootcamps, co-founder bootcamps, peer groups, internal trainings and organizational change management for your company, and plenty of rich resources for entrepreneurs, such as our podcast.
Ready to go deeper? Let’s get started.

Our Services

Our Results

  • "To the degree Gimlet is both a good place to work and a good business, it is a direct outcome of the work we have done with Jerry. We now recognize that without self-reflection from its leaders, a corporation turns into a grinding machine that churns through people and leaves behind a residue of profits (best case). The project Jerry is embarking on is bringing humanity and decency back into our work as we build the company. And now, with Reboot, he has built an organization and a group of coaches, who can deliver on that project in profound ways."

    Matt Lieber

    Co-founder of Gimlet Media

  • “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 Reboot 360 process is amazing. The clarity and honesty of this is excellent. As a board member, these are the best 360 performance reports I've seen.”

    Fred Wilson

    Union Square Ventures

  • "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

    CEO of Twilio

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.

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Case Studies

  • Engaging in a coaching relationship represents a significant commitment of time and money, and we want you to get the most value and impact from your investment.

    In this document we detail how and why coaching works the way it does, what to expect from the coaching relationship, and share our advice for showing up in a way that helps you get the most out of your sessions.

Reboot Team

Since we began, we’ve set out to do “good work, done well, for the right reasons,” and inspire others to do the same. It’s always an honor to be a guide on our clients’ paths towards enhanced leadership and greater resiliency. That journey requires the practical skills needed to do the job, radical self-inquiry to understand what we’re really up to, and the sharing of the experiences to know we’re not alone.

In all that we do we remain true to what we call “The Conversation;” the dialogue we all must have around our existential relationship with work. All our work takes root in that place where one enters the dialog between self and work, life and purpose.