How to build healthy, helpful co-founder relationships (and recover when things go wrong).

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"Our investors don't know"

I had a recent first call with co-founders struggling in their partnership. We were introduced by another client who had gone through her own cofounder challenges, which she had navigated in part through our coaching work.

I agreed to take the introduction in part because I love working with teams of co-founders; I believe deeply in the powerful role a strong cofounder relationship can have in the life of a founder. Too often, these relationships become instead a source of stress, as was the case here. The two founders took turns outlining their situation on our call:

We recently raised a round, and our investors don't know. We faked it well through the fundraising process, and we do our best to hide from the team the friction that exists between us. But it is getting harder to keep secret. And we are both pretty miserable.

Currently, I am working concurrently with four cofounding teams helping them explore their way through similar challenges. Over the last few years, I have also been fortunate to coach numerous other founding teams. This work, as well as my own experiences with my own past co-founders, has inspired a firm belief that:

1. Cofounder relationships can be a source of resiliency and well-being in the entrepreneurial journey
2. They frequently are not

Startups are hard enough. Trying to build a business or organization without the close support of a trusted ally is like heading off to navigate the Alaskan backcountry alone. You can do it. You might even survive. But wouldn't it be nice to have some support and friendly conversation along the way? Wouldn't it be more enjoyable to have someone with whom to tell the story when you return?

Whether you are just starting out on something new with a prospective cofounder or have worked with someone for years, and whether that relationship is feeling solid or rocky, I hope the reflections below might be of assistance to you. Long-term relationships of any kind are full of challenges. They can also be the greatest source of sweetness for any part of life's journey. I hope these reflections open up some ideas for you on what might be possible in your own working relationships.

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Some notes from modern psychology

A few years ago, when my wife and I were navigating a season of change in our relationship, a friend recommended the book Hold Me Tight, a wonderful book written by one of the preeminent scholars in attachment theory, Dr. Sue Johnson.

Sue's book exposed me to one of the most famous studies in attachment theory: Lending a Hand: Social Regulation of the Neural Response to Threat.

In the study, participants were subjected to the threat of electric shock. Participants held no one's hand, a stranger's, or their spouse's hand. The following abstract outlines the results:

Results indicated a pervasive attenuation of activation in the neural systems supporting emotional and behavioral threat responses when the women held their husband's hand. A more limited attenuation of activation in these systems occurred when they held the hand of a stranger. Most strikingly, the effects of spousal hand-holding on neural threat responses varied as a function of marital quality, with higher marital quality predicting less threat-related neural activation in the right anterior insula, superior frontal gyrus, and hypothalamus during spousal, but not stranger, hand-holding.

The stronger the relationship with the partner present, the more resilient the participant was in the face of stress!

At Sanity Labs, we have been exploring the applications of this study to founding teams. The informed gamble is the more connection and trust we can build between co-founders, the more resilient we make them in the face of startup adversity.

I was in a coaching session recently where the CEO exclaimed, "I think I might actually like this job!" His sentiment in this proclamation stood in stark contrast to the sadness and anxiety he seemed to be carrying in many of our conversations. He explained, "I think it feels painful when I feel misaligned with my co-founders or the team."

Most of the CEOs I meet with describe feelings of loneliness or isolation. They explain the work feels largely on their shoulders; they are uniquely tasked with figuring it all out. Moreover, they view "keeping it all inside" as part of the job.

One CEO recently explained how his work anxiety was creating distance between him and his romantic partner:

I feel like I cannot tell her about the anxiety and doubts I am having. We made this decision together to take on this bet. We are now years in. We have built much of our life together around this role and this company. How can I tell her I am having doubts about the business? How could I possibly share that I am not sure I want to keep doing this?

We hold our teams at a distance out of a sense of duty. We keep anxieties secret from our co-founders out of a false belief that that's 'part of the CEO job.' We often create distance even from our friends or romantic partners, believing they cannot possibly understand what we are going through.

The truth is all of these relationships are opportunities for connection, alignment, and support.

But letting people in isn't always all that easy. It sometimes requires reshaping our beliefs about leadership, independence, masculinity, or femininity.

The particular challenges of cofounder relationships in difficult seasons

This move toward connection can be particularly challenging for co-founders during the most perilous seasons of company-building, right when the connection is needed most.

Those of us with children will know this challenge viscerally. Those of you reading without children can learn from our experience here without suffering the 3 AM crying baby!

When my wife and I were pregnant, a good friend gave me some sage advice:

There are going to be a lot of moments in this first year with the baby, usually around 3 AM, when you and Holden (my wife) are going to look at each other and think "I hate this person! I made a huge mistake!" Do NOT act on that impulse. Recognize that it is stress and exhaustion. It is not the relationship that is the problem.

Navigating the first year post-baby-birth, I found my mind frequently returning to my friend's advice. Looking back, there were two parts to his insight. The first was that exhaustion drains our ability to connect meaningfully with others or to retain perspective. The second part is that when we face existential challenges, such as the seismic questions new parents often hold ("Did I do the right thing having this baby?"), it is easier to blame those around us for our situation than ourselves.

We are hard-wired to care for our new child in the new baby example. She is utterly helpless without us. Rarely will we blame her for that first year's difficulty. Few of us have the maturity and groundedness to sit in that difficult and own our own culpability: "Let me remember in the presence of this crying child at 3 AM that I made a reasoned choice to have this baby and that I need to own my part in creating my own challenge!" What is easier is to lash out in frustration at our partner. If only he (or she) would do more, care for us better, and take an extra middle-of-the-night feeding, things would be better. It is easy to judge and push away the person whose support we are most longing for.

The same dynamic often happens with co-founders.

I remember vividly a morning in year one of my first venture-backed startup when my cofounder, Todd, and I spent an hour walking the streets near our office shouting at each other. I do not remember what we were arguing about for the life of me. But looking back, the reason for the argument is clear: we were both stressed out and overwhelmed. We did not know what we were doing. We felt our lives, livelihoods, careers, and families' well-being were on the line. The person walking next to us was the easiest person to take all that anxiety out on. So we did just that.

Todd was my best friend (and still is!) He was the person whose support I needed most. Later, when my marriage fell apart, and I lost a child, I would move into his guest room, and his late-night support would help me survive. But in those early months, I found it hard to let him into what was happening inside me. By holding back, I robbed myself of the potential support that was right there in front of me.

All long-term partnerships bring challenges. Marriages, business partnerships, long-term friendships, shared experiences, and challenges that bond us also bring friction. That's normal. The opportunity is to stay close through that conflict, to commit and re-commit to closeness and openness. For co-founders or business partners, in the workplace and life, that intimacy can be a goldmine of support and resiliency.

Setting a cofounder relationship up for success:

If you are in the exploratory stages with a prospective cofounder, or in year one of the journey, this is a wonderful time to build a strong foundation for a long-term partnership. (If you are years in, fret not, it isn't too late!)

You may not hit everything on the list below, and that's ok.

Things to look for in a prospective cofounder:

• Shared history
• Complementary skills
• Aligned-values

Let's dive briefly into each.

Shared history

Starting a company with someone you have only recently met is a bit like getting pregnant with someone on the first date. You are signing up to raise this thing for at least ten years or so; make sure you pick the right co-parent.

That is very hard to do if you are just getting to know each other.

If you are considering starting, or have already started, a company with a newer acquaintance, make extra time for the exploration outlined below.

Ideally, you find a cofounder or co-founders you have known for years and with whom you have already been through some journey (school, work, navigating life, etc.) This will help you understand how and why you will respond in the challenging circumstances that are an inevitable part of starting something from nothing.

Complementary skills

As you vet prospective partners, taking a hard look at your skillsets may also be helpful.

Founders who share skillsets (business-oriented founders, all technical founders, etc.) may find it easier to get along in the early days, but it can make it difficult to 1) find your lanes as you collaborate to achieve leverage and 2) create the kind of cross-function exploration often necessary to uncover more innovative solutions.

One maxim I find to be an interesting place to start is:

A founding team should possess the mix of skills required to get version one of the product or service to market.

For a traditional technology company, that often means a mix of engineering, design, product, and operations. No one size fits all here, but this lens may be a helpful place to start.

Aligned-values

One of the most often overlooked elements of a founding team set up for success is alignment of values.

What matters to each of you?

What is motivating you to start a company in the first place?

What are you willing to sacrifice? What are you unwilling to sacrifice?

One of my biggest regrets as a founder was not having more values-oriented conversations in the first year of the business. We knew we were excited to work together and build something high-impact that we cared about, but in the early days, that is where the conversation stopped.

Later, when we had to make decisions about how much capital to raise, what kinds of people to hire, and how broadly we were willing to pivot when the early product didn't work (among dozens of other decisions), we found it hard to slow down and come into alignment on what mattered to us.

Every hour you spend exploring values on the front end will save you 10+ hours down the line. It may also save you from making a painful choice on the cofounder front.

Setting your cofounder relationship up for success

Once you have made your selection of co-founders, there are a few practices that will be helpful in setting you up for long-term success in your partnership. If you take time for these elements in year-one of your partnership, you will be ahead of 99% of teams out there.

1. Discuss key questions
2. Make conscious commitments
3. Run a comprehensive pre-mortem

Let's dive into each.

Key questions for discussion

Many cofounder teams I meet with describe waking up months or even years into the partnership to find they started the business with very different expectations in mind. Most describe realizing they never spoke openly about their different expectations, hopes, or values.

Like a dating relationship that begins with fun, flowers, and a feeling of endless possibility, the early stages of a cofounder relationship and the excitement of starting something can cover up all kinds of unspoken differences. But, just like in dating, those differences, when left unexpressed, show up as major trouble areas down the road.

We can preempt those long-term challenges, vet the relationship, and strengthen the right cofounder relationships by tackling some big topics in advance.

Below is a list of questions I have found helpful to bring into cofounder conversations in the early days. I wish my co-founders, and I had spoken more deeply about each of these, but you can learn from our mistakes!

These questions are by no means the end of the conversation, but they have the potential to provide a rich beginning.

Journaling individually about each question is a great place to start. Talking openly with your co-founders about your answers will set you well ahead of the average founding team and give your company a firm footing for future growth.

1. What is your personal life mission, your reason for being?
2. What are your personal values?
3. What is a story from your life where you were most being you?
4. What does success look like for you with this business?
5. What are you willing to sacrifice for the success of this business?
6. What are you unwilling to sacrifice?
7. How can this business best support the life you long for?
8. What do you need outside of work to show up as your best self at work?
9. What support from me do you need to show up as your best self?
10. What would you like me to start doing, stop doing, or change to be the cofounder you need most?

The arc of these questions is designed first to help you explore together, on the front end, how you might align the mission and working style of the company you are building with the life you desire to be living.

The second goal is to begin forming agreements on how you will approach the work. What will you put on the line? What will you not? How will you know if you are headed together in the right direction?

The third goal is to explore what you need to show up as your most supported self and to do your best work. The greatest benefit we can give one another as co-founders is support. Humans are more creative and effective when we are supported. These questions can help get you headed together in the right direction on the support front.

How to make conscious commitments

Once you have taken a chance to explore the questions above together, it may be helpful to spend some time together writing down and talking through the commitments you are making to one another as you begin this business.

Anytime we begin new relationships or partnerships, professional or otherwise, we bring expectations about how the relationship will go. In most relationships, these expectations go unspoken. Similarly, any commitments or expectations we bring into the relationships go unnamed. We then behave a certain way, believing we are living up to our commitments in the relationship, only to find we are letting our partner down in some way we did not see coming. Or we wake up to find ourselves disappointed when our partner lets us down in a way that to us feels obvious but which, looking back, we never clued her or him in on.

As you form a new professional partnership or a new iteration of a long-lasting friendship or partnership, the goal is to make your expectations explicit and form any agreements you wish to make consciously.

You might do this around a whiteboard together or with a stack of sticky notes or a journal, making time to brainstorm an exhaustive list of the expectations you are bringing into the partnership and any commitments you believe would be helpful in making the partnership what you need it to be.

This might include commitments on:

• Protecting your relationship
• Balancing work with the rest of your life
• How you hold values
• How power is shared in the partnership
• How decisions get made
• ...and anything else you can dream up that would be helpful to you in having the partnership you desire

It may be helpful to allow this to be a living document you return to regularly in your partnership, ideally at a regular interval and anytime things feel off track. Holding it as a living document allows you to add to, remove, or edit the list as needed over time. Long-term partnerships evolve as our circumstances and ourselves change.

Making the mistakes in advance: how to run a comprehensive pre-mortem

Before kicking off a cofounding partnership, it may also be helpful to run a pre-mortem on the experience. If you are not familiar with how pre-mortems work, fret not, they are very simple!

You may have come across post-mortems before. Post-mortems are popular particularly in engineering cultures as a way of naming and metabolizing lessons-learned after a project is completed.

I like post-mortems. But I love pre-mortems. Pre-mortems allow you to reap the benefits of lessons learned without ever having to make all the mistakes are experiencing all the resulting pain and frustration.

I like to do pre-mortems when beginning any new partnership: a business partner or cofounder, a prospective new investor or board-member, a new senior team member, or even before kicking of a big new customer relationship.

To conduct a pre-mortem with your prospective cofounder, do the following:

Supplies:

• A quiet space
• 90 minutes of time
• A couple of stacks of sticky-notes
• A black marker for each of you
• A pad of paper or whiteboard for notes

Here's the process:

1. Set aside 90 minutes or so in a quiet space.
2. Sit together with your eyes closed to begin. With your eyes closed, have one of you paint a nasty picture for some time in the future (perhaps 18 months out). You might say something like "Let's imagine things have gone horribly wrong. We are sitting here in this very room 18 months from now, and we can barely stand to look at each other. We are bankrupt. We have lost all motivation. Neither one of us has any idea how we are going to recover. We are burned out, angry, and depressed. And most of all, we are furious at ourselves and each other for all we did wrong.
3. Next, open your eyes. You should take a stack of sticky notes and a black marker. Set a timer for 10 minutes or so. During that 10 minutes, write down as many things as you can imagine that went wrong to allow such a disastrous outcome. Write one thing per sticky note. One sticky note, for example, might say, "We stopped having fun together" or "We were not clear on how we would make decisions."
4. Put the sticky notes on the wall. Group them loosely by theme. You may, for example, have a group under "Communication" or "Decision making." Group them as you see fit; there is no need for perfection here.
5. Now, work your way through each of the themes. Take your time. As you encounter each theme, discuss what you might do to avoid the mistakes represented. For example, if "Stopping having fun" comes up, you might decide to prioritize time together outside the office.
6. Capture everything that comes up. The ideas generated may become the foundation for the working norms in your partnership and for your company culture. They may also be helpful in exploring what you might need to ask of each other or commit more explicitly to each other to make the partnership work.

That's it! You have completed your first pre-mortem.

Pre-mortems are wonderful because, in addition to helping you identify some blind spots in your planned partnership, they also help you to develop a shared language for identifying and troubleshooting what could go wrong. Lastly, they get you talking about difficult issues before much is on the line. If you can hang onto that practice of talking openly about the hardest things, your partnership will be well-served.

Practices for maintaining the relationship(s)

Once you have made conscious commitments to each other, completed your pre-mortem, and talked through any resulting requests or new commitments, it may be helpful to brainstorm some practices for maintaining your cofounder relationship as the company gets off the ground and begins to take flight.

Below are a few practices I have witnessed clients use to great benefit.

1. Treat your relationship like a third-party
2. Find quality time outside the office
3. Practice inviting all parts of yourselves to connect
4. Make and practice clear communication commitments

Let's walk briefly through each of these.

Treat your relationship like a third-party

Each of you as individuals have needs. You need rest, food, physical exercise, connection, intellectual stimulation, and more.

Your relationship also has needs.

Think of your relationship as its own person or entity. What helps her thrive? What shuts her down? What are her different needs?

Identify those needs. Talk about them together. Prioritize space for them.

Find quality time outside the office.

One of the most common mistakes co-founders make as companies scale is failing to prioritize time together outside the office. Some even fail to continue to find time together inside the office!

When my cofounder Todd and I started our last business together, we were best friends. Fast forward a couple of years into the business, and we rarely spent any time together outside the office. Our relationship became soaked through with the stresses of running a venture-backed startup. Even being in the same room together at the office was sometimes painful. We eventually caught ourselves and began the slow process of rebuilding our friendship outside the business.

Don't make the same mistake we did. It is bad for your friendship, whether a new one or many years old, and it's bad for business.

Make time to have fun together and connect outside of work. In the same way, a family with young children benefits when the parents make time for fun date nights; teams benefit when the leaders maintain a fun connection outside the rigor of the day-to-day.

It doesn't matter what you do. Do something you both find fun. Do something that takes your mind off of work. The only rules should be:

• Do it just for the fun of it
• Leave the work talk behind for a few hours

Practice inviting all parts of yourselves to connect

Another helpful practice you might bring into those fun hours outside the office is inviting all parts of yourselves to connect.

We are all multi-parted people. We have driven, adult parts. We have playful, child-like parts. We have emotional parts. We have spiritual parts.

However you hold your own make-up, consider how you might explore and maintain connection with your cofounder(s) from these different parts of yourself.

As an example, if you are a CEO and find your intellect or your 'driven' parts typically run the show, it may be deeply refreshing to invite your sillier parts to connect. It might be time for some karaoke or an evening of toilet-papering your favorite board member's house! Don't get arrested, but do get playful.

Make and practice clear communication commitments.

One last practice I will mention is to make clear communication commitments. I meet many founders who are frustrated by the way their co-founders do or do not communicate with them.

People have different communication preferences.

Some people are happy jumping across channels: text them, email, Slack, DM...they are open to it all.

Other people (myself included!) find this maddening. If you are ok with a 24-hour response, email me. If something is on fire, call me.

It may also be helpful to discuss response commitments and work/life divide. How quickly are you committing to get back to each other? When are you committed to giving each other space from work and how might you support that space?

These ideas are just a starting point. There is no need to limit yourself to only these!

Edit them to make them your own, add to them, or toss 'em out and make a list that feels right for you and your partnership. Like conscious commitments, this can be a work-in-progress that evolves over the life of your partnership.

How to recover when things go awry

Even if you walk carefully through each of the practices above, even if you choose a wonderful cofounder(s) and be thoughtful in how you kick off and manage the partnership, there will be times when things go wrong.

Every single long-term partnership hits hard times.

Hopefully, in your pre-mortem, you came up with some ideas of how to recover when hard times hit. But here are a few more ideas to aid in the hard months.

Seek space

When things feel heated, take a break. Take some time away from the office or apart from each other.

When you are angry with your cofounder, address your anger first before trying to resolve any underlying issue.

Check-in with yourself. Give yourself what you need. Come back to the conversation and exploration from a more resourced place.

Seek help

Relationship challenges of any kind are not easy to navigate alone. Often, it can be helpful to have a dispassionate third party in the room. That could be a coach, a trusted team member, or a friend.

Particularly if the challenges are long-standing, bring in some help.

You are far from the first to experience cofounder challenges and will not be the last! It shows strength and wisdom to ask for help.

Air grievances

If there are specific issues causing frustration, once you have addressed your own anger and needs on your own, take some time to name the issues together.

It may be helpful for each of you to write down the issues you see in advance.

You might down:

1. What you experienced (what you saw, heard, etc.)
2. How it made you feel (happy, sad, frustrated, etc.)
3. Any stories that came with it for you (i.e. "when you said 'X' I found myself telling myself you didn't really need me....)
4. Any needs or requests you have

Writing these things down in advance my make it easier to communicate from a place of clarity and groundedness.

Go back to the beginning

It may be helpful to take some time together and remember why you got into this partnership in the first place.

This could be as simple as sitting over beers and telling stories.

When I run cofounder off-sites aimed at helping folks reconnect and find a more fruitful path forward, one of the things I love to do is have each partner journal about their memories of the early days of the partnership:

• How did you first meet this person? What drew you to her or him?
• How did you decide to work together?
• What did you to view to be her or his superpowers?

I like to have the co-founders sit back to back and share the answers to these questions. Being back to back lets them share without managing the other's response and also take in what is shared without worrying about their own response.

It is a simple exercise, but the the results are without exception profound.

Re-visit or create new conscious commitments

In addition to remembering how you got here, and sharing what is or isn't working for you in the partnership at the moment, it may be helpful to revisit or create new conscious commitments for the partnership.

What did you previously commit to? How do those commitments need to be emphasized or edited in light of what has been shared?

What new commitments might support your partnership in light of what you are experiencing?

Co-design the path forward

Every day is a new opportunity to design the future. Humans and organizations are fluid.

It may be helpful to slow things down for a day and talk about the path ahead:

• What would make the next 18 months of your partnership better than the last 18?
• What is waiting to begin in your partnership?
• What needs to come to an end?
• What would you like to be saying about your partnership 18 months from now?

Might even be time for another pre-mortem!

Investing in the proactive design (and redesign) of your cofounder partnership is one of the most powerful investments you can make on behalf of your business, your team, and your life.

Well-wishes

Leadership can be a lonely endeavor.

Your co-founders can be your greatest source of connection, resilience, and deep partnership. It takes work, and bumps in the road are normal.

Seek connection and support whenever you can find it. You deserve it.

Companies are too hard to build alone.

Life is most richly lived in deep connection with others.

If I can be of assistance as you navigate your own cofounder hopes or challenges, please reach out. I would love to help.

With love from my desk in Los Angeles,

-Matt

I appreciate that you are here. If you were forwarded this email and it resonates, you can subscribe here.

Looking for some support? If now is the time to consider coaching (or a CEO peer circle) reach out here.