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Better Humans Make Better Leaders.
Better Leaders Create Humane Organizations.

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 believe better leaders make better humans, and better humans create more humane organizations and places of systemic belonging.

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

Nathan Barry

“I highly recommend the team at Reboot. … They’ve been such a help to me that I’ve hired them for my entire leadership team.” Nathan Barry CEO, Kit

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Reboot’s Approach to Coaching

At Reboot, executive coaching is not merely about acquiring leadership skills or executing business strategies—it’s about transforming your experience as a leader and, ultimately, as a human being. And true transformation comes only from integrating practical skills with deep psychological insight. While most coaching companies emphasize practical strategies or emotional intelligence, Reboot’s distinctive approach ensures that leaders not only develop external skills but also address unconscious psychological patterns that may hinder their full potential.

“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

Reboot’s foundational philosophy blends practical skills with radical self-inquiry. While practical skills equip leaders to manage day-to-day business challenges, radical self-inquiry uncovers the deep-seated emotional and psychological dynamics that influence how leaders show up in their roles. This combination, especially in 1:1 coaching, forms a powerful catalyst for growth, making Reboot’s approach stand out from traditional executive coaching models.

Practical Skills + Radical Self-inquiry

Many coaching approaches stop at advising on operational excellence and interpersonal skills. However, Reboot believes that leaders must also engage in self-exploration, learning how their unconscious patterns, formed from past relationships and experiences, affect their present-day behavior and decision-making. It’s this blend of introspection and action that leads to greater resiliency and enhanced leadership.
Our Formula
Practical Skills + Radical Self-Inquiry + Shared Experiences
=
Enhanced Experiences + Greater Resilience
Practical Skills + Radical Self-Inquiry: A Potent Combination for Growth
You can’t lead well without grasping the principles of operational excellence (Practical Skills), but simply knowing those principles alone can’t get you where you need to go. The only way to move through the living complexity of leadership and organizational challenges is to be growing from the inside out (Radical Self-Inquiry).

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Our Services

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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Expert Coaches, Real-World Impact

Reboot’s coaches bring relevant context to bear on the coaching relationship in two ways. 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.

On Being with Krista Tippett - Jerry Colonna:

Can You Really Bring Your Whole Self to Work?

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Transform Your Leadership.
Transform Your Organization.

For more than a decade, Reboot has supported thousands of leaders from startups to Fortune 50 companies in bridging the gap between where they are and where they want to be. Our proven coaching supports you in navigating the complexities of work and life with newfound confidence and clarity.

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We’re so glad you’re here.

We believe 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.