Co-Founder Reboot

Solidify your co-founder relationship with this free five day course.

“Work does not have to destroy us. Work can be the way we achieve our fullest self.”

Know Thyself & Know You are Not Alone

Welcome to the co-founder Reboot. We are glad you are here. This course is designed to be taken by you and your co-founder(s) together. We suggest each co-founder sign up for the course to complete each day’s readings and the independent exercises.

Over the next five days we’ll be taking you and your co-founder(s) through lessons and exercises designed to bring understanding, alignment, efficiency and satisfaction to your relationship.

Anyone who has ever flown knows to put on your oxygen mask first before helping those around you. No adage is more applicable to any relationship, professional, or personal. To show up for others we must first show up for ourselves. With that in mind, if you or your co-founder are struggling and new to a practice of self-inquiry, we highly suggest that you first start by Rebooting yourself with our original 5-Day Leadership Reboot before embarking on the co-founder course. Don’t worry, we’ll be happy to hold your spot.

Over and over again via every vessel of Reboot we hear from entrepreneurs of the transformative impact of understanding that they are not alone in their feelings, struggles, and fears. The connection and relief that comes from knowing you are not alone- is profound. That’s why we built this connection through shared experiences into our DNA at Reboot, as a core principle of the Reboot formula:

Practical Skills + Radical Self-Inquiry + Shared Experiences = Enhanced Leadership + Greater Resiliency

While, we’ll address every element of this equation through the next five days, it won’t surprise you to learn that we’ll start by sharing some experiences.

You can connect with other co-founder Reboot participants by using the #co-founderreboot hashtag on Twitter or Facebook.

We’d also love to hear from you. Reach us at @reboothq, on our Facebook page, or by shooting us an email.


In 2012, Harvard Business School professor Noam Wasserman studied 10,000 founders for his book “The Founder’s Dilemma. His research found that 65% of startups fail as a result of co-founder conflict. That’s higher than the divorce rate.

Having conflict in your co-founder relationship is normal. Having a conflict is not a sign of failure. In fact, not having conflict can be a sign of a bigger problem. Lack of conflict tells me one of two things, either you don’t think your co-founder can handle open and honest feedback or you think the relationship is already so fragile that you are walking on eggshells. Either way there is a fundamental rift in the relationship that if not addressed will likely lead to the even deeper conflict. It is how you deal with conflict that makes the difference.

We see the same three manifestations of co-founder conflict in our offices or events over and over again. We think it prudent to start by sharing them with you.

The Founder That Doesn’t Scale

The most common manifestation of co-founder conflict is what happens when one co-founder doesn’t scale. This conflict is often recognizable by one founder’s comments to the other that “I work harder than you” or “I don’t know what you do anymore.”

Let’s start at the beginning. When two co-founders come together and decide to found a company the first question is always: Who’s going to be CEO?” Eventually someone has to be CEO. Depending on how the company grows from there you have differences in scaling.

By definition the goal of most venture backed startups is to scale. Scaling well is not easy. When you have rapid growth, it’s really hard to grow your skill set at the same pace.

We often find the CEO will scale faster than the non-CEO; the built-in requirements of the CEO position forces a growth that may not come otherwise: she has to pitch, do board meetings, etc. There are these things she must learn. It’s really trial by fire. Scaling is not optional.

The non-CEO founder , who may or may not go on the pitch meetings for raises, may be there for board meetings but not put the deck together, is responsible for certain things but not the company as a whole in the same way the CEO is. This co-founder usually goes on to lead a specific team or business function. While there are pre-built-in mechanisms that force the CEO to scale, it is not inherent that the non-CEO will scale or manage a group of people effectively.

If the non-CEO co-founder is not scaling and founders have done their job well and hired talented and driven people, the CEO will start to hear from team members who are upset with the leadership. These team members will come to the CEO saying things like, “This person doesn’t know what they’re doing” or “I don’t think I can work here if they keep interfering/micromanaging/second guessing.” If nothing changes these key hires will start resigning–a huge red flag to the CEO and the board. While it is natural for the first generation of leaders to eventually move on, what Fred Wilson calls “Turning the Team” The resignation of later stage and often more experienced hires is frequently on of the first sign of failing.

The CEO who is scaling will try to save employees from leaving or repair the team(s) that are dysfunctional under the leadership of the other co-founder. This just snowballs the conflict

because now it looks like the scaling CEO-founder is undermining the non-scaling founder. It won’t be long before the non-scaling founder comes out swinging, saying “Hey, you are telling my direct reports what to do and now they don’t respect me anymore.” It just crumbles into all kinds of other dysfunction. The scaling CEO has has come from an earnest desire to help but has now created more conflict.

Who Decides What

Leadership is about making decisions. Oddly enough, many founders never take the time to discuss who will decide what. This lack of clarity upfront and strategy to decision-making quickly leads co-founders in one of two undesirable directions.

In the first scenario, all decisions are made by all founders. This results in a slow or gridlocked decision-making process. When decisions are finally made, they are often then changed because there is no one clear decision maker — any founder can reopen any decision.

Employees and investors quickly get frustrated with the slow decision-making process or the constant changing of decisions. If there are more than two founders, the situation is only exacerbated by the orders of complexity between the number of founders who have to be aligned for a decision to be made.

The problem is the idea that we have to decide everything together despite the fact that everyone is going to have a different viewpoint.

Consider the differences between a visionary founder and a technical founder. Visionary founders look to the future and imagine how great it’s going to be out there. Technical founders look at today and say, “This whole system is going to crash tomorrow. We have bad code, bugs, and technical debt. We need to fix this now.” One founder is looking at the ground in front of their feet while the the other is looking out at the horizon. When they have a conversation they are looking at two different landscapes. They can’t figure out why they can’t agree on what they’re looking at because both think they are looking at the same thing. That is the paralysis and conflict that happens when we each inherently have different viewpoints but insist that everyone has to agree on everything.

As challenging as different viewpoints can be, these differences in viewpoints are the reason why co-founders often work out better than solo founders. A diversity of viewpoints is an asset to the company but needs to be accompanied with a framework for who decides what.

In the second scenario, the CEO makes all decisions. This leaves the non-CEO founder feeling disempowered. They will often resort to having hallway conversations undermining the CEO, reversing decisions, or slipping into the background and not scaling. It won’t take long before the CEO says to the co-founder, “Hey, when I look at what the company has accomplished this last year, I don’t see what your contribution has been. I’m wondering if you should keep your title or if we should just have you on the board and hire somebody else in your role.”

Both scenarios are are not desireable.

The Forgotten Founder

The third source of co-founder conflict is the most heartbreaking because it only arises if everything is going really well and you are getting noticed by the press and outside world for your accomplishments. In this scenario the co-founders have already successfully navigated through the first few common co-founder conflicts. Both are scaling, both are doing their jobs, and they are both making effective decisions. They have a healthy relationship and things are going really well.

Here’s the problem: The co-founder named CEO does all the interviews, gets all the articles written about them, speaks at conferences and is named to the latest 30 under 30, 40 under 40, etc. The non-CEO co-founder starts to wonder, “If we are equals, decisions are split equally, we are both scaling, and if I’m contributing just as much as the CEO, why are they getting all the interviews? Why doesn’t anyone outside of the tech community know my name?” The non-CEO co-founder feels forgotten and alienated. In response they will often fight for more internal control (see Who Decides What), which leads to not scaling (see The Founder Who Does Not Scale) because they are playing a popularity contest instead of continuing to focus on their roles which is what has already made them successful leaders.

We believe this conflict can sometimes be the worst because it is purely ego. Put simply it is the sentiment of: “You are getting the spotlight and I’m not.” As a coach it’s truly heart-breaking to watch because this conflict often pops up when there are really healthy operational co-founder relationships, and the company is doing really well, but for whatever reason they are just getting unbalanced coverage in the press.

Consider these examples: There are three co-founders of AirBnB, but most people outside of the tech community can only name Brian Chesky. There are two co-founders at Dropbox and most people outside the tech community can only name Drew Houston. This is just the way the media works; they like one hero. It’s rare that there’s more than one. So the hero gets invited to speak at conferences, and gets invited to the CEO summit, they’re invited by the VC to the CEO dinner with the very influential tech visionary. The non-hero co-founder is working just as hard, and bringing a tremendous amount of value to their company but receives none of the cool benefits of being a founder.

The challenge is only exacerbated by the fact that the CEO is enjoying the notoriety, the special invitations, the award shows. Who wouldn’t? It can be hard for a CEO to give that up.

Do any of these scenarios sound familiar? Don’t despair. They come directly from our work with some of the biggest and most successful startups. Instead, know that if you found yourself in these you are in good company and there is hope. Many co-founders have faced these challenges and found avenues to move through them with tact and grace. You can too.


Journaling is a powerful tool for self inquiry. Writing, especially stream of consciousness free writing, allows parts of you to be voiced in an unedited way. It creates the opportunity to discover what deeper parts of yourself – parts that may be tuned out during normal day to day work activities – may feel or believe. We suggest you embrace artisanal journaling (the old pen and paper) for this course.

Give yourself ample time to write freely about each prompt until satiated. Hold off on sharing your writing with your co-founders for now. Don’t worry, we’ll get there. For today journal on each of the three following prompts:

What drew you to this company?
Why were you drawn to your co-founder(s)?
What do you want to accomplish in your company?

Tomorrow: We’ll learn 3 practical tools for preventing conflict in your relationship and spend some time in practicing radical self-inquiry about our underlying feelings about work.

“A common reason for startup fatalities, particularly in the early days, is some sort of conflict between cofounders. One of the main reasons for cofounder conflict is that many aspects of the relationships were either ill-defined or misunderstood. To minimize the chance of this, it’s critical that you and your cofounders come to agreement on some key issues.”

David Cohen

What Do You Feel About Work? + Three Practical Skills to Prevent Conflict

Welcome back to day two of the co-founder Reboot. Yesterday we began this course by looking at three of the most common manifestations of co-founder conflict. Did you recognize yourself or your team in any of the scenerios? You’re not alone. Conflict is normal and is a healthy part of any relationship. What matters is how we acknowledge and move through conflict that can make or break teams and companies.

Today we’ll take a look at three practical skills to prevent and move through co-founder conflict. Just as yesterday’s conflicts are pulled directly from our work as coaches, so are these solutions. These practices are cornerstones of healthy co-founder relationships we share with our clients, workshop attendees and bootcampers.

Don’t forget that you can connect with other participants at any time through the

#co-founderreboot hashtag on Twitter or Facebook. You can also reach us at @reboothq, on Facebook, or by email.


Understanding the detrimental effects conflict can have on a co-founder relationship and their company, you face a choice. Will you choose to navigate conflict mindfully? Will you choose to invest in building trust, in building a solid relationship with your co-founder(s)?

Yesterday we spent time detailing the three most common manifestations of co-founder conflict. Today we will be diving into three practical skills to prevent and move through those conflicts in your relationship.

Decide Who Will Decide

The healthiest companies decide who is best at deciding what. Each co-founder has their own ball to run with. If a decision is made that is totally egregious, there is veto power. co-founders agree that each co-founder will have 100% of the decisions all of the time in their respective area, but the other co-founder(s) reserve the right to veto if they feel it goes against a core value of the company or steers the company too far from the mission. The veto is to be used very rarely; you should trust your co-founder to make the decision in the domain in which they are an expert.

If co-founders are not able to operate with this level of trust to let the person hold all the decisions for the domain for which they are responsible for dysfunction usually follows.

The healthiest way to approach decision-making is to split the domains. The most popular split is internal-external. One person in charge of people operations, finance, legal and anything that is internal to the company. The other person is external — fundraising, engineering and product, anything customer-facing. There are other functional models that work as well. The important thing is to decide who is responsible for which functional areas and to stick to that decision and respect each other’s domain of responsibility.

Like each of the conflicts we will discuss in this series healthy conflict fundamentally comes down to two things, trust and respect. Trust that your co-founder can make decisions and be honest with you when things are not going well. Respect your co-founder enough give them honest and open feedback as things start to not feel right. Trust and respect has to start at the very beginning with the very first conversations about starting the company including who will be CEO, who decides what, and other key conversations.

Level Up

Einstein said, “We can’t solve problems by using the same kind of thinking we used when we created them.”

We like the word “level” because one of the ways to deal with conflict is to move up one level above the current conflict to an outcome you both care about. At some moment both you and your co-founder cared deeply about the success of the business, what was best for the business and how to get it off the ground.

When you are in a place of conflict, it’s probably a place of personal conflict. All sorts of voices in your head start telling you things: “You are not scaling. You are not leading. People are leaving your organization. You are not delivering.”

To heal you need to bump out of the “You” and into the “We.”

“What do we want for the people that work for us? What do we want for our investors? What do we want for the company?” From there you can work your way into asking, “Is this working?,” “Is this the best thing?.” It is hard for anyone’s ego to to say, “I am building something great and I no longer can be a part of it in a leadership function.”

The inverse of the non-CEO not scaling is the CEO who does not scale. While not as common it is not infrequent either. It is just far less likely that they will be fired or removed from the company. You may be asking, “Why don’t founding CEOs get fired? The truth is that the thing all founders have that no outside hire will ever have in the same way is the vision for the company, and the passion and drive to make that vision a reality. The founder is the one who saw something in the world and said, “I need to create this.” They have been thinking about it deeper and longer than anyone else. You just can’t get that from an outside hire. That’s why when CEOs struggle to scale, they’ll sometimes hire a great executive in a senior role, or a seasoned coach, to guide them for a time. That’s one of the reasons why the Google guys hired Eric Schmidt, and Zuckerberg hired Sheryl Sandberg. This happens all the time, but the vision is always the vision of the founder.

Healthy co-founders ask what’s best for the business, what kind of company are we trying to build, what kind of experience do we want to have. What kind of company would we want to work for?

Sharing Is Caring

Like it or not we all are ego driven. Teams or individuals who choose to put their head in the sand and ignore this fact are setting themselves and their companies up for failure. To avoid dragging your co-founders and teams into an ego trap with you, co-founders need to find a healthy split of the perks of success that works for them, just as they found a healthy split in who runs what in their company.

Press and publicity can be addressed by talking to the company’s PR agency and creating guidelines that split one set of topics for one founder and anything on another set of topics go to the other founder.

Co-founders can take turns speaking at conferences.

The “hero” can be mindful about sharing sharing acclaim with their co-founder in interviews and at events.

An excellent example of a successful shared leadership is Warby Parker. It is clear that Neil Blumenthal and Dave Gilboa are purposefully sharing responsibilities and public recognition of leadership.

Another example of a company who navigates this well is Lyft. There is a clear distinction between who is CEO, Logan Green, and who is president, John Zimmer, but there is a lot of shared publicity and clearly split responsibility. In their recent billion dollar funding announcement, probably one of the most significant press announcements to-date for the company and when most CEOs would take the spotlight for themselves, it was John Zimmer, the president of Lyft, who did much of the press.

JW Player has come a long way. The JW player and platform is now used by over 2.5 million publishers and 20% of the fortune 1,000 companies. Each month about 1 billion people watch video on their platform. Behind those numbers are real people–including three co-founders who, over the last eight years, have experienced their own profound personal growth and leadership transformations.

In this episode of the Reboot podcast the 3 co-founders of JW Player join Reboot partner Jerry Colonna. In a very open conversation, they explore key challenging moments in their company and partnership history -and how they emerged from those moments stronger and more committed than ever. It’s an inspiring story of how they became leaders in the moments of conflict.


What is success?
What is failure?
What kind of Company do you want to build?
Why does this company need to exist in the word?
What kind of company do you want to work for?

Tomorrow: Communication is critical. We’ll have two practical communication tools for you, a video of our most powerful (and requested) video on the practice of being fierce and you’ll be doing a little communication with your co-founders.

Becoming a Leader: The Crucible of Co-Founder Conflict

“To be adult in relationship is not to be conflict-free. It’s to resolve conflicts mindfully.”

David Richo


Long before Men are from Mars, Women are from Venus was a household aphorism humans have understood that communication is the key to a healthy relationship. Archaeologists have even unearthed evidence of early Greeks and Romans studying the art of persuasion and oration. Given this track record you might expect that we would all hold being effective communicators at the core of our life’s pursuits, though this is rarely the case. Our society and industry rarely grants thoughtful and effective communication with the same clout as more popular hard skills such as engineering, development or sales.

Certainly there are exceptions to this rule, but they remain few and far between. Any member of team Reboot will quickly gush about the far reaching benefits of healthy communication, but we’re not quite holding our breath for the appearance of 30 under 30 best communicators in Forbes magazine. But there is one place where you’ll see communication in startups brought up time and again: When a company fails. A glance at any company post-mortem will yield multiple references to challenges and breakdowns in communication between co-founders, in board relationships, with customers, through the entire organization, or perhaps most common: all four.

If you want to have healthy communication throughout an organization, it must be built in to the DNA. The tone and value you set as co-founders will affect how each and every other relationship in your company carries. It’s vital to get this right.

Today we’ll be looking a lot at what healthy communication looks like and specifically why we at Reboot believe that being fierce is key if you want to survive the high and low spots ahead.

You can join us in discussing this course with the #co-founderreboot hashtag on Twitter or Facebook. Questions, compliments or complaints for us? Reach us @reboothq, on Facebook or send us an email.


Be Fierce, Not Ferocious

We always instruct leaders to be fierce, not ferocious. What does that mean?

It means that one of the most compassionate things you can do for a human being is to tell them when you observe that they are not succeeding in a role. We often think that we need to be nice we need to be kind and not hurt anyone’s feelings, but that is actually one of the most violent, least compassionate things you do for somebody because we are allowing them to fail and then learn and grow from that failure. You’re watching them fail. Then the next thing is they will get fired, they will leave, something will happen. The relationship will break. They will be left wondering how you could sit there and watch them fail and not say anything. By being really nice things go really, really wrong and then we wonder what happened. That is what the absence of conflict looks like.

Imagine watching your co-founder (or substitute co-worker, direct report, etc.) struggle in a role and hearing about it via feedback from employees or the board and not sharing that feedback with your co-founder until enough time has gone by that you have to or you will either lose a valuable employee or lose the trust of the board. So you finally give your co-founder the feedback and in their mind they are thinking “you have watched me fail for months and have been talking about it to the board and/or employees for months but not telling me”. At this moment a large portion of the trust that may have existed between co-founders is lost. This is the same trust that is necessary to repair the relationship.

The Context of Caring

Healthy feedback is always given in the context of caring. One of my often repeated prescriptions to co-founders is that their new favorite word is the word is “because”. Because when you are going to give feedback, you are going to give context. That context is going to be something like, “Because you are an amazing CTO, and I think you can be an amazing people leader, I want to give you some feedback.” Then you give the feedback. Without context our brains will always make the worst meaning possible about any feedback. Our survival wiring is setup to see threat before reward.



Honest, open communication is not always easy, however it is vital to a healthy co-founder relationship. This Being Fierce talk is one of our most popular for a reason: it works.

Resources: Active Listening

Active Listening

Most people do not listen with the intent to understand; they listen with the intent to reply. – Stephen R. Covey Sure we all know how to listen, but all listening is not created equal. Learn to shut off automatic listens and listen for accuracy, empathy and mutual creativity.

Honest and Open Questions

Honest and Open Questions

We ask honest and open questions of others when we are acting a support for that individual on their path to inner discovery. This style of communication can be challenging to start and takes practice, but its rewards are deep.


One thing I’d like to know about my co-founder(s) is…. One thing I’d like my co-founder(s) to know about me is… How do you want to work together?


The day has come to sit down with your co-founder and have an honest and open conversation about what you’ve learned thus forth through reading, listening and your journaling. Gather together your notes and journaling, select a private location where you both feel comfortable and set aside some time (at least one hour) to talk without feeling rushed.

For your discussion, give each person a turn to speak about their journaling, reactions to the readings and recordings and exercises we’ve covered so far. The listener(s) should not respond in any way. No questions or commentary. Each person may speak for as long as they need.

When they are finished, move to the next person to share. This share should not be reactionary to the person(s) who spoke previously. Do this until each co-founder has had the opportunity to share.

Once each person has had the opportunity to speak, you may then ask clarifying questions of each other. A clarifying question is a simple question of fact and should be asked in the interest of understanding and verifying that you correctly understood what the person was sharing.

Some examples of clarifying questions are: Do I understand you correctly that…? Did I paraphrase what you said correctly? Is this what you said?

Tomorrow: Jerry, one of our co-founders and partners, can often be heard saying, “This being so, so what?” We’ve identified the three most common sources of co-founder conflict, identified practical skills that strengthen relationships and discussed communication. Tomorrow will be looking at where we go from here. How do you imprint this all into your and your companies DNA? Getting started is easier than you think.

“It is in the space between inner and outer world, which is also the space between people—the transitional space—that intimate relationships and creativity occur.”

D. W. Winnicott

This Being So, So What?

You’ve swallowed a lot over the past three days. We’ve tackled the three most common conflicts, looked at some practical skills to navigate and prevent conflict and scratched the surface on the vast art of communication. Feeling a little overwhelmed? It’s ok.

At times like these Jerry will be heard saying, “This being so, so what?” So? So what?

If our experience can tell us anything, it’s that no matter if you are in conflict or even in a co-founder relationship you signed up for this course because you are ready, open to try doing things differently. And that is awesome. And exciting. And scary as hell.

Remember: You Are Not Alone.

Today’s reading and exercises are all about moving forward and establishing the relationship that’s right for you and your team.

Reach out to other participants by using the #co-founderreboot hashtag on Twitter or Facebook. Reach us at @reboothq, on Facebook, or by email.


Vision, Purpose & Commitment

Will Smith and Jada Pinkett-Smith have been married for more than 20 years. A few years ago they were in an interview where they were asked: “You two are one of the rare successful Hollywood couples; What’s your secret?” Their answer? “Really at the end of the day, it’s just not quitting.”

In founding companies it’s really the same. If you go in saying, “Separating is not an option. This needs to exist in the world,” you have humility. You realize that your work is bigger than any individual egos. That if it’s doing what it’s really meant to be doing in the world, it could have a profound effect.

You have to care about the company existing in the world more than you care about whose name is on the latest headline or your title on LinkedIn. You just have to say, “I don’t care. This has to exist. We are going to build this.”

Let Go of Your Ego

Most conflict stems from ego. The rapid scaling of high growth startups is hard, if not next to impossible to match with your skill set. Where founders get into trouble is when they put their ego and their desire to have a certain title, or be perceived in a certain way by the world, ahead of what the investors are backing and what the employees signed up for. You need to be willing to put the business first and be open to the fact that mean asking for help, or acknowledging that maybe you can best serve the business in a different role.

What is most important is you allow yourself the space to reflect on what you really want, what your motivations are, why you decided that this company had to exist and you had to be the one

to build it. This is why having clear understanding of vision and purpose when you start the business is so important. If you have both, humility shows up and you can get through almost anything. Don’t let ego cloud that vision.

Asking For Help

Maintain a willingness to ask for help and an open mind around what that help looks like. Maybe you need to work with a coach or join a peer group to help you overcome practical challenges, emotional challenges or both. Maybe you need to allow somebody else to step in and lead for a little while while you catch up to the business. .

When Google was scaling rapidly they recognized they had a lot to learn and brought Eric Schmidt. They allowed an experienced CEO to come in for a little while, used that time to scale themselves and then took the reins back. It’s okay to take a pause and let somebody show you how to scale.

A lot of people will say, no, we only believe in founding CEOs –and yes, there is a lot of data that supports that. Absolutely.–there is also a moment where you have to ask yourself, what do I want for my company and how will I best grow? I don’t believe that one size fits all, but there is the right choice for you and your company and it is worth taking the time to figure that out.

Trust and Respect

Healthy conflict fundamentally comes down to two things, trust and respect. Trust that your co-founder can make decisions and be honest with you when things are not going well. Respect your co-founder enough give them honest and open feedback as things start to not feel right.

Trust and respect has to start at the very beginning with the very first conversations about starting the company including who will be CEO, who decides what, and other key conversations that we will cover in future posts.

The key to having and being fully present in these conversations is not being afraid of who you are today and who you are in the process of becoming through the struggle and joy of startup life.

What if your agreements with partners and co-workers were more focused on the characteristics of how you come together, related to one another, and work together, instead of what happens when sh*t hits the fan? What if your co-founder agreement came from a place of hope instead of fear?

Zelle Nelson and Maureen McCarthy are co-founders of The Center For Collaborative Awareness and our guests for today’s conversation. They’ve created a collaborative process

called “The Blueprint of We,” a mindful approach to build and sustain healthier, more resilient business and personal relationships and partnerships – those that start from a place of hope and openness. They join Jerry to share how they came together, how the process works, and how this work can impact your relationships and your organization.

Exercise: The Blueprint of We

We at Reboot use the Blueprint of We in our own leadership and personal relationships. This abbreviated Blueprint of We is a great place to start with your co-founders. If you are interested in the full Blueprint of We or other Blueprint resources visit

Mindful Partnerships

“Real listening: to listen “without presupposing, classifying, improving, controverting, evaluating, approving or disapproving, without dueling what is being said, without rehearsing the rebuttal in advance, without free-associating to portions of what is being said so that succeeding portions are not heard at all.”

Abraham Maslow

Read: The Bet

When the four Reboot partners brought our collective experience and training together to form this company, we identified an equation, what Jerry will often refer to as “the bet”, which guides all we do. That equation is:

Practical Skills + Radical Self-Inquiry + Shared Experiences = Enhanced Leadership + Greater Resiliency.

Reboot is a coaching company, yes. But more than that, Reboot exists as a container for us to do our work as humans. We believe that work can be the way we achieve our fullest selves.

As we have walked through this five day co-founder Reboot we’ve really been moving through this equation. We started with the shared experience in identifying three of the most common manifestations of co-founder conflict: the founder that doesn’t scale, who decides what, and the forgotten founder.

On the second day, we looked at three practical skills you can follow to prevent and move through co-founder conflicts: leveling up, deciding who will decide and sharing the rewards of success.

Next came the art of communication. We learned to be fierce, not ferocious; and how to offer feedback in the context of caring.

Yesterday we embarked on the framework for a healthy relationship: vision, purpose and commitment, cultivating trust, asking for help and letting go of ego. None of this would be possible without the self awareness and vulnerability that comes from a regular practice of self-inquiry.

Reboot’s friend and teacher Parker Palmer speaks often to the incredible power of speaking to our fears and concerns. To bring them out of the shadow. When people share something particularly painful or hard to talk about, Parker will often respond, “Welcome to the Human Race.”

Shared Experiences

Our motto at Reboot is “Know you are not alone. Join the conversation.” The knowledge that we are not alone in our struggles, in our shadows, is prodigious. Through our work at Reboot, we find that time and time again, when someone is willing to open up and share about the things we don’t talk about, one of the most uttered responses is one of resonance: “Me too!” Sharing our true, honest selves is how we as a community help each other. By partaking in this course you know that these conflicts, these challenges of relationship are not unique. It is perfectly normal to be challenged and to at times struggle with relationships. By connecting on these issues, we can help each other.

An Invitation

The question we pose to you is: what you will do with this knowledge? We believe these challenges are an invitation. An invitation to do the work. To dive into our work, our lives, our relationships openly, vulnerably and emerge anew. Then, we become one step closer to the leader, the partner, the human we were born to be.

Exercise: The Clarifying Conversation

Instructions and guidelines for clarifying conversations were included on the final page of the abbreviated The Blueprint of We document we shared yesterday. If you have already had the opportunity to follow those directions to have a clarifying conversation about your Blueprint, excellent. If not, we highly encourage you to do so. In addition, we suggest you have a clarifying conversation about this Reboot experience by following the clarifying conversation guidelines to discuss the following with your co-founder:

What did you learn and experience through taking this Reboot? What did you discover about your co-founder(s)?

What changes would you like to bring to your relationship with your co-founders? What practices can you integrate into your relationship going forward?

Keep the Momentum Going:

“At its best, work seems never-ending only because, like life, it is a pilgrimage, a journey in which we progress not only through the world but through stages of understanding. Good work, done well for the right reasons and with an end in mind, has always been a sign, in most human traditions, of an inner and outer maturity. Its achievement is celebrated as an individual triumph and a gift to our societies. A very hard-won arrival. – David Whyte

Reboot offers a wide range of experiences and resources to support you and your team as you embark on your own version of “good work, done well, and for the right reasons.”


We offer two additional Self-Guided Programs in the style of this co-founder Reboot: Reboot Your 2016 and a 5-Day Leadership Reboot. These have proven to be great things to share with your teams, colleagues and close friends.


The Reboot podcast showcases the heart and soul, the wins and losses, the ups and downs of startup leadership. On the show, Entrepreneurs, CEO’s, and Startup Leaders discuss with Jerry Colonna the emotional and psychological challenges they face daily as leaders.


We have handfuls of great essays on organizational health, emotional health, resiliency, depression and other curious topics on Medium, where we publish a Leadership and Resiliency column.


We curate a weekly Startup Digest on leadership and resiliency. Get the best six to eight L&R articles and a mini-koan in your inbox every Friday.


Coaching is the core of Reboot. We help entrepreneurs and their teams deal with the internal ups and downs of entrepreneurship and support the growth they need to improve their performance and their life. In addition to working closely with CEOs, we also work with executive teams and management layers within organizations. Learn more about coaching and meet Reboot coaches.


Reboot Circles are Reboot coach-led, Reboot curated groups of five to six peers committed to doing the work of radical self-inquiry and growing as leaders from the inside out. Members of Reboot circles say that for the first time they can open their hearts and be real, and many find that remarkable and refreshing. We offer Reboot Circles for CEOs, non CEO co-founders and other members of your leadership team including your CTO, CMO, and Head of People.

Learn more here.


Learning & Development (L&D) trainings are designed for teams of any size, ranging from your leadership team to your whole organization. Our L&D offerings provide a mix of content that helps to develop skill, capacity, and experience that in turn helps to grow the human being in their work. Trainings engage and bring participants into new levels of understanding of themselves as leaders and as people, and of the impact actions and behavior have on others. If you’re curious to learn more about what we do, and how to bring Reboot to your entire team, fill out this form or contact


Bootcamps are an incredible way to jump start your coaching or take it to a new level. Our legendary Bootcamps are both rigorous and relaxing by blending pragmatic wisdom, time in nature, mindfulness, shared meals and lots of honest conversation. Immerse yourself in the complexity and vulnerability of being a CEO with a cohort of up to 14 other smart and courageous entrepreneurs and the support of Team Reboot. We offer several flavors of bootcamps including events for CEOs, co-founders and Reboot Quest. These are life-changing events and a great way to dive deeper into who you are as a leader.


Follow us on twitter. Like Reboot on Facebook. Connect with our team via email.

Check out more self-guided courses