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.
Two Reboot coaches flew out to the founders’ retreat for the Better Tomorrow Ventures portfolio companies. In two half day sessions to take the group of founders in a deep dive of processing and reflection via a series of exercises and group conversation.
“I’m filled with admiration and gratitude for you both — and I know the founders who were at Camp feel the same. You brought in a very special and memorable element to this year’s Camp. It was beautiful to witness. Thank you for making the long journey out to Camp, for extending your support to the mealtimes and 1:1 coaching slots, and for helping these founders explore deep and important areas!”
Sloane Gerritzen
Chief of Staff, Better Tomorrow Ventures
Veterans United engaged Reboot to support the development of heart-centered, business-minded, and conscious leaders. Over four years, Reboot delivered a range of services, including individual leadership coaching for emerging leaders, virtual leadership trainings for larger groups, and the creation of peer coaching circles. These circles, launched with an in-person event on-site and sustained through bi-monthly virtual sessions, enabled high-potential leaders to develop advanced communication and listening skills, unlocking transformative growth across the organization. The initiative was seamlessly integrated into VU’s broader leadership development strategy and has been widely embraced.
“One of the things I love most about our partnership with Reboot is how deeply Carl and Jerry have come to know our company, our leadership culture, and many of us individually. When they are on-site with us, or coaching us virtually one-on-one, they feel like part of our family—it’s a powerful experience in the moment. But even beyond those moments, the connection we’ve built inspires greater possibilities for our leaders and our organization. A great example of this is our peer coaching circles, which have continued meeting on their own for years now, showing just how fully embraced and impactful this work has been for Veterans United.”
Erik Morse
Director of People Development at Veterans United
A large, diverse, global virtual organization (Automattic) embeds coaching into their organization. They work with Reboot regularly on leadership coaching programs and 1-1 coaching with key leaders. The multi-day management training retreats give the team a space to speak honestly and learn from other team leads across the org. They feel less alone. The impact of the coaching program has leveled up the performance of the leadership and management layers.
“Prior to Reboot …, we didn’t have that many tools for our leaders. Now, I feel like our leaders are really well supported.”
Steph Yiu
Chief Customer Officer at WordPress VIP
Reboot engaged with BrightFarms at a pivotal stage in their growth to clarify and strengthen the company’s leadership philosophies. Beginning with interviews of the leadership team to surface current and anticipated challenges, followed by an offsite to uncover shared principles such as commitment, openness, results driven, and empowerment. These insights shaped the design of the BrightFarms Leadership Academy where participants experienced the core leadership frameworks required to lead effectively in their roles.
Reboot has been a key partner along the way, facilitating offsites and receiving feedback to further improve the Academy, setting the stage for continued growth of the people and BrightFarms.
“Working with Chris and Reboot has been game-changing for BrightFarms. Chris brings deep expertise in leadership and real-world application, but what truly sets him apart is his heart. He takes the time to understand our culture, our challenges, and what will actually work for us—not just a one-size-fits-all solution. With his guidance, we built the BrightFarms Leadership Academy, a leadership program that’s practical, impactful, and deeply embedded in our organization. Chris doesn’t just teach—he empowers. His approach ensures that the work is truly ours, making the impact real and lasting. If you’re looking for a partner who leads with both wisdom and genuine care, Chris and Reboot are the ones.”
Steve Platt
CEO, BrightFarms
The Brooklyn Museum brought Reboot in for an 18-month engagement to transform their group of skilled executives into a unified and cohesive executive leadership team. Through individual coaching, monthly executive leadership meetings, and off-sites, Reboot provided customized leadership, organizational development, and on-time support during this transition.
After solidifying these best practices with the executive team, we expanded reach by facilitating leadership development training at the middle and senior management levels.
BkM is a non-profit located in the heart of Brooklyn and is a gathering place for art, social action, and community gathering. The 400 person staff includes everything from facilities, art and curatorial, public programs, development, engagement, finance, to the operators (art handlers, guest experience, groundskeepers, security, marketing, etc).
Reboot was brought in a year before their 200th anniversary celebration. Half of the team was new, and others had been with the organization for years. Prior to our arrival, their executive team was very siloed and requested some outside assistance to bring them together in the hopes of building cohesion, shared language, trust, and working together more effectively.
“Chrystal and Ray are truly exceptional coaches. They met us at a time of massive transition, a time when we were riding wave after wave of crises. And with a new leadership team from varied backgrounds and different visions for the future, Chrystal and Ray helped us come together as colleagues and humans. They created an environment where we could talk through challenges openly, giving us the space to slow down and break things into bite-sized pieces that we could tackle. Most critically, they helped us find common ground, taking our base fears and transforming them into a north star vision for the future. Chrystal and Ray worked with our teams on an individual level as well, helping each of us explore our personal power and how we show up to the table. They guided us in putting names to individual patterns, enabling us to better understand each other. Throughout the process, they provided deep care and attentive listening, investigating comments further until we reached meaningful insights and answers. Their dual approach of supporting both team cohesion and individual growth proved invaluable. Without question, we are a stronger team and organization as a result.”
Anne Pasternak
Brooklyn Museum
“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.”
“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.”
“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.”
“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.”
“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.”
“Reboot’s 360 process gave me the honest feedback I needed to see my strengths and areas of growth in a beautiful light. Combined with one on one coaching, I’ve used this newfound self-awareness to execute a new roadmap. Reboot accelerated my leadership and my company is skyrocketing.”
“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.”
“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.”
“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.”
“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.”
“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.”
“I was absolutely blown away by the love, compassion and camaraderie I experienced from and with my fellow bootcampers and from the Reboot team. “
“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.”
“… 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.”
“Bootcamp helped me answer a stunningly difficult question: what behaviors or beliefs have gotten me to this point in my life but are no longer serving me? I believe my resulting resolutions will make me a better partner and husband.”
“For a founder or investor looking to perform at your peak, you need to know and identify your limiting beliefs. Any unresolved emotions create knots in the flow to your potential. Reboot Bootcamp is the place to examine your limiting beliefs and untie the emotional knots. Reboot provides a peer group that you need to jump to the next orbit.”
“The Reboot Weekend feels like the golden ticket, the Polar Express suddenly arriving with room for you aboard. Welcomed into the world of reflection and other ways to see, you return home with the ability to hear the bell forever.”
“All aboard,” the conductor cried out. I ran up to him. “Well, he said, “are you coming?” – C. Van Allsburg. The Polar Express.
“This was one of the most profoundly impactful events and rare collection of people, I have ever been privileged to experience, work with, walk side by side with, or to know. The learnings, life experience, expertise, sharing, character and integrity, authenticity, kindness, caring, and compassion rocked me, transformed me, inspired me, liberated and freed me.”
“My experience at Bootcamp was transformative on so many levels, 6 months later I am still unwrapping and having new fundamental insights about myself and how I interact not just with my company, but with the world around me. The entire Bootcamp team and content is there for one purpose, to give those of us that embark on this crazy, unrelenting, all-consuming, amazing and at times painful journey, a place to reflect, take stock and take a breath in a safe, supportive and quiet place. I miss all of them and the farm and can’t wait to find another excuse to get back there. My last comment, if you’re searching and you’re reading this, go”.
“As women leaders, we have few if any opportunities to go deep with our peers in a supported, safe, confidential environment. Isolation kills. Not only will you face the shadows that limit you, and embrace your greatest strengths, you will leave knowing deep in your bones you are not alone. Bootcamp is as courageous as the leaders it serves. If you’re ready for true transformation, if you’re ready to face the shadows that limit you and embrace your greatest strengths, Bootcamp is for you.”
“I am blown away by what an impact it has had on me both personally and professionally. Bootcamp gave me a structure to look inward at issues I didn’t even realize I had, and when I came into contact with those issues, it unleashed a flood of hidden pent-up stress and blockage. Bootcamp also gave me a safe place to explore those issues, free of judgement. I find myself feeling freer than I have in a long time and excited to keep my own exploration going. I’m more grounded at work, I’m more present at home, and I’m more at peace with myself. If this is the tip of the iceberg, I can’t wait to dive deeper.”
“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.”
“Going into the Reboot weekend, I was beyond tired and empty. I didn’t know if I needed a break or a change. The weekend was just what I needed. It was a break and a change, but it was not at all in the way I imagined. I went in feeling intimidated and left feeling recharged and, well, rebooted. It was real work that was, at times, hard and emotionally exhausting, but it was also filled with great joy and comfort that was rewarding.”
“Reboot’s team of amazing coaches are world class at helping fast growth company leaders grow into their roles and develop leadership talents.”
“‘Radical self-inquiry’ is something I can’t really get enough of as a CEO. Reboot Bootcamp provides me with a framework that I can use every day, to better understand myself and how I interact with others. It’s had a profound impact on my life.”
“I found just what I needed and it was different to what I was looking for. It has already changed my approach to leadership and everyday life”
“Best investment I’ve ever made in myself as a leader. Radical self-inquiry is a powerful mechanism to uncover blind spots, flat points, and also strengths. I was able to deeply reflect on what I wanted to change in my company’s culture, Reboot gave me the skills to do that in a few short days. The impact has been tremendous at my start up. I highly recommend CEO Bootcamp for seasoned and budding leaders alike!”
“How can you justify the cost of being a more self-aware leader and human? If you want what’s best for yourself and your organization, Reboot is a no-brainer.”
“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.”
“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.”
“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.”
“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.”
“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.”
“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.”
“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.”
“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.”
“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.”
“Bootcamp was a unique, eye-opening experience. It helped me to better understand the human struggles that come with building a start-up”
“I think that there are no better ways to spend your money if you want to enhance your leadership.”
“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.”
“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.”
“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.”
“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.“
“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?“
“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.”
“Put simply, it was the most powerful and moving experience of my life.”
“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.”
“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.”
“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.”
“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.”
“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.”
“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.”
“Truly one of the most transformative few days of my life.”
“It fundamentally changed the trajectory of myself and my business.”
“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.”
“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.”
“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.”
“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.”
“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.“
“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.”
“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.”
“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.”
“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.”
“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.”
“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.”
“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.”
“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.“
“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.”
“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!”
“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.”
“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.”
“The CEO Bootcamp retreat was totally life-changing. Not just work-changing. Life-changing.“
“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.”
“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.”
“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.”
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