Practical Skills

+ Radical Self Inquiry

+ Shared Experiences

= Enhanced Leadership + Greater Resilience

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.

Our Clients

Case Studies

We have hundreds of happy clients who have bravely ventured on the journey of self-actualization with us. Read about how two companies worked with us in our recent case studies.

View Case Study

  • “Reboot has been one of Etsy’s most important business partners as we’ve grown over the past years from a scrappy startup to a more mature public company. From executive coaching to org design, the coaches at Reboot have worked alongside Etsy’s management team at key moments in our evolution. They are uniquely able to combine a keen sense of business strategy with humane acknowledgement of the spiritual/emotional dimension of work. To put it simply, Reboot gives you the tools to build great leaders and a great company.”

    Chad Dickerson

    Chad Dickerson

    CEO of Etsy

  • “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

  • “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

    Fred Wilson

    Union Square Ventures

“This was one of the most incredible experiences of my life, one that I will hold dear, forever. I leave a better investor, board member, boss, colleague, father, husband, and friend. A better man.”

David Goldberg

David Goldberg

Principal, Corigin Ventures

“… the magic comes not from any particular exercises or tools, it comes from the people involved. The Reboot team possesses an otherworldly talent for coaxing authenticity and truth out of people. They can even coax truths out of people who, like myself, have been lying to themselves for years.”

Jacob Chapman

Jacob Chapman

VC, Gelt Venture Capital

“I was absolutely blown away by the love, compassion and camaraderie I experienced from and with my fellow bootcampers and from the Reboot team. “

Elaine Stead

Elaine Stead

Head of Venture Capital, Blue Sky

“Bootcamp is an opportunity to step back, honestly look in the mirror and understand oneself better. This has made me a better investor, but more importantly a better person​. I made some of the deepest connections with my VC peers over 3 days at bootcamp that I have made in my 6.5 years in venture​.​”​​​

Brendan Dickinson

Brendan Dickinson

Partner, Canaan Partners

“There are no words I can give you that will do justice to the profound changes that Bootcamp will induce in you. Bootcamp is a salutary pause in a life of speed and busyness that allowed me to reconnect with myself and others.”

Fred Destin

Fred Destin

Investor, Accel

“Allow yourself to be submersed in a weekend of vulnerability, accountability, friendship and a keen sense of purpose. Your leadership skills will be stronger and you will live with intent after reflecting on how your special talents in the VC world will make you a better investor/advisor/mentor/board member but more important, a better person.”

Grace Belangia

Grace Belangia

Sand Hill Endeavors

“For the first time in a long time, I am at peace. I know what I need to do, and more importantly I know why I’m doing it. Everything else is just execution.”

Dave Mao

Dave Mao

Managing Partner, Come Up Capital

“Reboot was a unique experience that I can recommend to any founder. Founders experience unique shared challenges across all stages of the company. Being in a group of amazingly self-aware founders who were willing to open up to the group about their struggles and, most importantly, listen to each other’s struggles was incredibly humbling. It takes courage to face your own struggles but there is no better partner than Reboot to help you start that journey. I loved every second of it.”

Laura Behrens Wu

Laura Behrens Wu

CEO of Shippo

“I went to the bootcamp to improve my leadership style, but I improved my life instead. The bootcamp is that great and worth every penny. A life-transforming experience.”

Amir Salihefendic

Amir Salihefendic

CEO at Doist

“Reboot is building something unqiue and vital, the world’s first startup incubator for integrity. The CEO Bootcamp removes the scales from our eyes as businesspeople and gives us the insight, the tools, and the community to become the leaders we long to be. You will emerge from Bootcamp as Luke did from Dagobah, a heartful warrior on the path to becoming a Jedi master.”

Tarikh Korula

Tarikh Korula

former CEO of Mahaya

“Reboot helped me step up to the plate, and understand how to be a genuine and authentic leader.  It gave me the space, strength and focus I needed to find my path and excel to be the best I can be.”

Misa Chien

Misa Chien

CEO of Praiseworthy

“Bootcamp gave me the opportunity to go deep with a group of people who truly understood my challenges – both personally and professionally. The experience not only put me on more solid ground as a leader, but it gave me the gift of an incredibly diverse group of trusted and empathetic friends to rely on and support as we continue our journeys. It was a transformative and life changing experience that I recommend for any startup leader no matter your past experience or the scale and scope of your business.”

Julia Austin

Julia Austin

CTO at DigitalOcean

“I expected a powerful experience from the bootcamp but it still shook my core…  The retreat proved to be a transformative journey with far reaching implications.  I bring back with me deep insights and powerful tools to become a better leader and person.”

Alvin Hung

Alvin Hung

CEO of GoAnimate

“For a People leader in a rapidly growing organization, it is easy to feel isolated in the support of others, with little time to reflect and focus on one’s own journey. Reboot Circles provides a powerful opportunity to share experiences with like-minded peer leaders in the same field, and work through common issues in a safe and authentic environment. Having that space to know that the challenges I am working through are ones that resonate with others as well, and having an environment to get peer feedback on potential new ideas and solutions, has proven invaluable to my personal and professional growth.”

Matt Hoffman

Matt Hoffman

VP, People, Digital Ocean

“Bootcamp helped me redefine my emotional relationship to stress and to the challenges that are just constant and pervasive in building a company. Having that change of relationship was completely reinvigorating. It gave me stamina, resilience and longevity in an industry that is notorious for exhaustion and anxiety. After attending the bootcamp, I became much more grounded and centered in who I am as a CEO, and that’s really important because you can spend a lot of energy and time chasing other models of some CEOs. Now, I know the place from which I make decisions. It’s a much more grounded, comfortable place to be. Bootcamp is absolutely worth your time and money. There’s an added benefit of expanding your community. And, of course, the weekend itself really, really moves you forward in ways that you can’t anticipate.”

Erika Trautman

Erika Trautman

CEO & Founder of Rapt Media

“What happens when you become an entrepreneur is you start to make sacrifices and investments into the business that you’re building and you almost forget about yourself. It’s important to realize that the company is a collection of people on a unified mission and sometimes you need to reinvest back in yourself to actually accelerate the company. So I would say definitely do it, not only for your personal balance but also to actually help the business, as well.”

Ben Uretsky

Ben Uretsky

Co-Founder & CEO of DigitalOcean

“What I would say to someone who is on the fence about attending bootcamp is you have no idea how much of a slam dunk decision this should be. Nothing helps your business’ chance for success as well as your personal chance for success as much as the bootcamp experience does.”

David Mandell

David Mandell

Co-Founder & CEO of PivotDesk

“Bootcamp was a unique, eye-opening experience. It helped me to better understand the human struggles that come with building a start-up”

Gunnar Froh

Gunnar Froh

Founder & CEO of Wunder Carpool

“I think that there are no better ways to spend your money if you want to enhance your leadership.”

Tracy Lawrence

Tracy Lawrence

CEO of Chewse

“This thing, if you’re ready for it, it can really change your life and your career; and as a CEO, you owe it to your stakeholders, to your staff, to your investors, even to your customers to be a better CEO, to take a step, get these four days and I guarantee, you will come out of it a better CEO.”

Mat Ellis

Mat Ellis

CEO of Cloudability

“Reboot is the top example that I can think of for CEOs if they want to make an investment in themselves and in their role as leaders.”

Mara Zepeda

Mara Zepeda

Co-founder & CEO of Switchboard

“My Reboot peer group is an opportunity to frankly talk about day to day challenges of a being a founder with other founders, feeling heard and understood by them. It’s a safe space where I can be myself and know that everyone else isn’t pretending to be someone else either. As it turns out, sharing experiences with others who’ve been in my shoes is just as important as practical skills when it comes to building a business.”

Evgeny Shadchnev

Evgeny Shadchnev

CEO and Co-Founder of Makers Academy

Reboot’s 360 review process was thorough and incisive, and it resulted in a report full of helpful insights for our portfolio CEO and the business. It was particularly useful to me and the other board members, as it provided a framework for us to use in helping the CEO grow as a leader, and measuring his progress against objectives.  I’ve since brought Reboot into other companies I work with.

Matt Harris

Matt Harris

Managing Director, Bain Capital Ventures

“It was life changing. I went into it thinking it would help our business and my co-founder relationship, which no doubt it did. But much more so, it helped me understand myself. Bringing back a mindfulness of who I am (the good and the baggage) makes interactions, decisions, and life more whole. It truly felt like a reboot of me and our business. Its still the same cofounder team and the same business, but without a lot of the junk getting in the way of us operating and living fully.

Todd Emaus

Todd Emaus

Co-founder of Twenty20

“After hearing about previous Reboot experiences from my co-founder Greg I came in expecting a lot. Who would have thought that I would end up blown away by my own self-discovery?

Johann Schleier-Smith

Johann Schleier-Smith

Co-founder of if(We)

The single most important investment we’ve made in improving as leaders and leveling up our company. More importantly, I feel more alive than I have in years.”

Matt Munson

Matt Munson

CEO & Co-founder of Twenty20

“Put simply, it was the most powerful and moving experience of my life.”

Dan Kador

Dan Kador

Co-founder of Keen.io

“It was absolutely fantastic meeting the other founders who came, and incredibly moving to really hear their stories and feel who they are. It was great to give myself the permission and the space to evaluate how I’m doing and how we’re doing as a founding team — space we don’t normally give ourselves.”

Jeff Schenck

Jeff Schenck

CTO & Co-founder of Chewse

“The Reboot team is absolutely the best in the biz.  They create a truly safe and vulnerable space where founders help each other and themselves with their deepest issues.”

Joe Greenstein

Joe Greenstein

Co-founder of Innerspace

“The bootcamp is a sacred place and moment. The perfect spot to fight your demons and to know yourself better, but also to realize that you are not alone and there is always someone next to you. For me the weekend was not about being a CEO. It was about how you live your life, how you feel about that and what are going to do to change it.”

Mauricio Silber

Mauricio Silber

COO of Trovit

“The only regret I have is that I didn’t attend sooner. Bootcamp helped me start the journey towards becoming a more self-actualized citizen of the world. I went seeking answers and left with a framework that empowers me to be an enhanced leader and happier person. Not only was it was a worthwhile investment for my company, it was a priceless investment for myself.”

Rob Cromer

Rob Cromer

CEO of Adcade

I can count on one hand the number of truly transformative experiences I’ve had in my life – CEO Bootcamp is on that short list. Jerry, Khalid, and all the other coaches created a safe space and gently guided me down the path of self-discovery. Equally important was the openness – the willingness to risk vulnerability – of the other participants. Honestly, words are inadequate to express the gratitude I feel for the Reboot team and the incredible weekend I was fortunate enough to attend.”

Char Genevier

Char Genevier

co-founder and former CEO of The Cotery

“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

“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 Cheezeburger

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

Khalid’s coaching and influence has significantly developed our managers and raised the performance, process, and execution of our leadership team. Khalid will continue to be a valued advisor/coach to the Lyft family in our journey to disrupt the Transportation industry.”

Ron Storn

Ron Storn

HR at Lyft

“There are likely several reasons why working with a coach doesn’t feel intuitive at first. Unease, fear, pessimism, or maybe a concern about a possible stigma. My own personal experience is that I wish I had worked with a coach sooner. I never told people (besides my wife) but I worked with Jerry when I was going through some tough times and very happy I did. He helped me more than he knows.”

Bijan Sabet

Bijan Sabet

Spark Capital

Truly one of the most transformative few days of my life.

Derek Flanzraich

Derek Flanzraich

CEO of Greatist

It fundamentally changed the trajectory of myself and my business.

Kyle Wild

Kyle Wild

CEO of Keen IO

I don’t think you can really put a value on an experience like the CEO Bootcamp. To spend an entire weekend with your peers and some incredible business coaches talking about really important issues and solving problems – that only happens once in a lifetime. I was deeply challenged by the Bootcamp and came away from it as a more effective, more authentic person and leader.”

Alex Raymond

Alex Raymond

CEO of Kapta

“I fought a 102 degree fever to go to the CEO Bootcamp. It changed my life. It changed my career. I urge CEOs: do. it.

Virginia Bauman

Virginia Bauman

former CEO of Tonx

“A onceinalifetime experience, the Bootcamp was the perfect combination of experience sharing, practical tips and self inquiry to help you understand what your job really is and how to be a better leader and person. And also many fun and magical moments that made the event truly unforgettable.”

Inaki Ecenarro

Inaki Ecenarro

CEO of Trovit

It changed the way I think about being a leader.  Actually, for the first time it defined what being a leader is.  It was powerful and carried more personal meaning than I expected.”

Andrew Cronk

Andrew Cronk

CEO of TempoIQ

“I hope you know what you’ve started. I’ve looked for this kind of experience for so so long. An open, playful, passionate group of people on the same journey – going for the same things. And all willing to keep sharing the process. It is really something special.”

Kevin Dykes

Kevin Dykes

Retention Grid

“It was transformational. The CEO Bootcamp enabled me to look deep inside myself and question who I really am and what kind of leader I want to be. Coming out of the weekend I truly feel that I am on the path to leading from a place of true authenticity, providing me with a feeling of freedom and certainty I have not felt in many, many years.

Paul Reinarz

Paul Reinarz

CEO of Rezora

CEO Bootcamp is an invaluable time to refresh, recharge and reexamine why we run companies. Supported by peers, coaches and the incomparable Jerry Colonna, I emerged after five days very grateful for this incredible program.”

Matthew Bellows

Matthew Bellows

CEO of Yesware

“It was just what I needed: An opportunity to unplug and reconnect with myself and others on the same journey. Leaders owe it to themselves and their teams to make this kind of investment.

Isaac Oates

Isaac Oates

CEO of JustWorks

“Awesome weekend. Great use of time, money and energy. It was great to connect with other founders/entrepreneurs/CEOs, learn and build a bond that I think will last for a long time. I feel the weekend provided me with a new set of tools for handling the day to day rigor of being the CEO of a company.”

Kevin Kelly

Kevin Kelly

CEO of Application Experts

The few days I spent at bootcamp have transformed who I am as a person. I was nearly put off by the talk on the website of meditation and yoga, but this only added to the incredible experience. After the retreat I feel more resilient and better equipped to face the daily challenges of being a CEO. I cannot recommend it highly enough.

Duncan Morris

Duncan Morris

CEO of Distilled

“My experience with Reboot.io was transformative.  It gave me great clarity for my purpose, not just in my business, but in my life.  CEO Bootcamp is not just good for one’s business, it’s good for one’s soul.”

Bart Lorang

Bart Lorang

CEO of FullContact

“It wasn’t what I expected. I thought it would be an opportunity learn some more leadership tools, to meet some great people, and learn about other exciting companies. It was these things, but it was also so much more. I was impressed by how quickly the group coalesced. There was a lot of trust in the room. That trust enabled a level of honesty and vulnerability that is rarely achieved in executive offsite or leadership development conferences. Everyone knows you’re your own worst enemy. Unfortunately, we don’t often invest the time to dig into those things that hold us back from being our best, most professional self. The weekend was an opportunity to do that in a guided and supported forum. It was intimate, emotional, and powerful. I wish I could do it quarterly.”

Sarah Bird

Sarah Bird

CEO of MOZ

“We were able to create a totally unexpected deep emotional bond among CEOs of such diverse backgrounds, yet with so much in common. It felt like a safe, respected circle of longtime comrades who were able to share the most unspeakable burdens…Finally.

Linnea Passaler

Linnea Passaler

former CEO and founder of Pazienti

Bootcamp is a safe space to do the inner work that helps me get to know myself better. With that, I am able to lead from my heart, find more meaning in my work, and live my life more fully.

Greg Tseng

Greg Tseng

former CEO of if(we)

“I both love the thrill of building my business and am challenged by the strains of doing so. The CEO Bootcamp posed a vision of how I can overcome my personal challenges, drive my company’s success and make the impact I want to make on the world all through a single, aligned motion based on authenticity. And the internalization of that vision is then charged by the energy of 20 CEO’s together opening up to one another around these challenges. My hope is that the experience has put me on a new path around which I plan to build my personal and professional achievements over the coming years.”

Toby Murdock

Toby Murdock

CEO of Kapost

“It was truly an honor to be a part of an amazing and magical CEO Bootcamp, and I would enthusiastically endorse the camp and the coaches to any CEO in the heart of “The Struggle”. Working together with with a thoughtful, compassionate, and diverse set of CEOs to tackle some of the most difficult challenges we face was one of the most amazing experiences of my business life. My only regret is that it ended so soon: it left me wishing I could go back again and again!”

Alex UrevickAckelsberg

Alex UrevickAckelsberg

CEO of Zivtech

Jerry and his team are magicians at what they do – inspiring a group of type-A, hyperdriven CEOs to move from their heads into their hearts and tap into each individual’s innate spiritual intelligence. I went to the Bootcamp expecting to learn how to solve all of my problems and instead learned how to “be” with my problems.”

William Morrison

William Morrison

CEO of Constellation Behavioral Health

“I believe the CEO Boot Camp was one of the best investments that I did for my company, my partners and my family. It pays tremendous dividends the minute you sign up. I feel my energy, commitment and a sense of mission and purpose has been pumped with steroids. Jerry is a Yoda Master, and his superpower is to make the strongest CEO become most vulnerable to make them even stronger for their teams, their community and for themselves. I could not recommend this program enough for all the Startup Founders, Entrepreneurs, Leaders and their investors. Jerry’s partners Ali, Michael and Sam are superstars who bring a balance to the notion of the four elements Body, Mind, Heart and Spirit. An effective leader needs to be super self aware to balance these 4 elements. The CEO Bootcamp makes you self aware and gives you the tools to build those leadership muscles. I would love to participate again to become more vulnerable so I can be stronger.”

Bala Kamallakharan

Bala Kamallakharan

Principal at Auro Investment Partners

“The CEO Bootcamp retreat was totally life-changing. Not just work-changing. Life-changing.

Evan Rudall

Evan Rudall

former CEO of Zearn

“Your podcast came at the right moment. I am listening your advice line by line. And I understand what I did…Thank you Jerry. Your messages are like a lighthouse in the sea of startup life.”

Sooinn Lee

Sooinn Lee

CEO of Locomotive Labs

“As I entered CEO Bootcamp I didn’t know what to expect. I found myself immersed in self discovery connecting with Jerry and the conference leaders on a deep level. While sharing experiences with like minded leaders I found myself becoming the CEO I thought I was in the beginning. CEO Bootcamp was a great investment and it’s value will live far beyond the week in the Colorado Mountains.

Joe Chura

Joe Chura

CEO of Launch Digital Marketing

“The experience of the weekend was one of challenge, camaraderie, and relaxation. It was a brilliant program, and the setting is awesome. I felt connected with the others in a way that I’ve really missed in the past few years – on an even playing field. Power relationships dot my world – most of the people I interact with on a daily basis have a role (staff, investor, customer, supplier, partner). This was a great chance to get away from that, and be open and honest with a group of other people. A chance to put down the armor, and be open about the human side of leadership.

One of the most relaxing and empowering aspects, was hearing one’s own experience voiced by another CEO in the group. The job at times is isolating, and lonely. Especially in regards to decision making. Hearing that this is not my issue, but rather something shared by many others, has been exceptionally valuable coming back – for I see a greater pool of people to connect with and discuss issues – both business and personal. My own ability to listen and communicate is greater than it was, and therefore, not only am I finding more connections, but also a much greater richness in those conversations. Great strides in resilience and presence are allowing me to ask difficult questions – and the benefits of that are huge.

Nicholas Russel

Nicholas Russel

former CEO of We Are Pop Up