I recently facilitated a session with 30 vc-backed founders. Conversations were flowing freely but in truth the energy felt a little flat…that was until someone mentioned their co-founder.

Welcome to this edition of The Wise Founder.

No prizes for guessing that we’re talking about co-founder relationships.

Coaching co-founders is amongst the most rewarding work that I get to do, primarily because when the relationship is going well it can be like rocket fuel for a company, but when it goes wrong…boy it can go wrong.

So if you’re a co-founder with great co-founder relationships then be thankful, but don’t take it for granted; and if you’re in the midst of some major co-founder beef then I feel for you. Either way, I hope you find something of value in what follows and if you’d like to know more then just hit reply to this email.

Co-founders, marriage and divorce

My wife is Catholic, I’m agnostic, so when it came to getting married we decided to do so in the Catholic Church. There were plenty of hoops I had to jump through - show up for mass at our local church, get written permission from the priest, help sort the local church database (yes that really happened), and attend pre-marital counselling. Most of these hoops felt like a chore (particularly the church database), but the counselling turned out to be a great experience - despite us having been together for 9 years and being the sort of couple that discuss everything, we still discovered new things about one another, and had really valuable conversations that have helped our relationship since.

So why am I talking about marriage?

Well besides a life partner or child, a co-founder relationship may well be the most intense and consequential relationship you’ll ever have. It is a marriage of sorts. When it goes well, it can be a key driver of success - in fact if you look at the top twenty most valuable YC companies as an example, all of them have at least two founders - but sadly, like marriage, more than half end in divorce.

So what can we learn from successful marriages, of both the life partner and co-founder variety, that might help more co-founders live their happily ever after?

1. Be aware of the common downfalls of other relationships

2. Don’t jump straight into marriage - build a solid foundation first

3. Be prepared to show up day-after-day for the long haul to navigate challenges and make things thrive

These are all things I love to work on with founding teams and I’m going to share some insights from that work below.

1. Be aware of the common downfalls - how do co-founder relationships go wrong?

• There’s a sense of unequal burden - this can manifest in overt ways like working hours, or the more covert such as a sense of mental burden i.e. if one founder feels like they’re the one always stressing about the future of the company in a way their co-founder(s) does not.

• There’s a sense of unequal reward - this will often play out if equity is not split equally amongst the founders. Beyond equity it can be seen in other areas too e.g. if one of the founders ends up getting a lot of the public limelight.

• There are too many co-founders - I was once involved with a company that started with six co-founders. That is too many. 2-4 seems to be about right. What played out with six was Game of Thrones style warring, backstabbing and forming of allegiances. Inevitably, 3 of the 6 ended up leaving.

• There’s a misalignment of values and vision - a surprising number of co-founders aren’t explicit about this upfront, and even those who are can treat it as fixed and fail to check back in on it regularly. When times get tough or difficult decisions need to be made, this is when any misalignment can really emerge.

• Life happens - big life events, such as one founder having a child, can lead to shifts in values, priorities and norms.

• Wrong person in the role - co-founders will typically dish out roles and responsibilities early on in the company’s journey, based on relative skills and areas of expertise, but as the company grows, so do the needs of each role. There will typically come a time for founders to shift into a new role or perhaps to step back altogether. Some will humbly identify this themselves and initiate the steps to make it happen, but others will end up being pushed by a co-founder.

• There are differing expectations of the relationship - co-founders may have very different needs from the relationship, based on personality type, other forms of support in life, other priorities etc. When one founder has greater emotional and supportive needs or expectations than another, resentment can build.

2. Don’t jump straight into marriage - build a solid foundation first

I’d recommend that all co-founders spend considerable time exploring important topics upfront (and then continue to revisit them). This is your pre-marital counselling phase.

Even if you’ve known each other for a long time, don’t take anything as given (some of the worst founder breakups I’ve witnessed have involved very close friends).

Here are just some of the specifics I recommend exploring:

Values and vision

All too often Co-Founders start a company based on complimentary skills without spending the time to establish if they’re truly trying to head in the same direction. Here are some questions you might explore:

• What are each of our core values?

• What are the values we want the company to represent?

• Who do you admire? Why?

• What does success look like for the company? What impact will it have had? What’s the company’s purpose?

• What does financial success look like for the company? Are we trying to build a billion dollar company with a public exit or a 100 million dollar company that gets acquired?

• What does success look like for each of us individually?

• Where does this company sit on each of our list of priorities in life? What else is on the list?

Self and mutual awareness

Conflict arises when two or more people hold their truth as the truth, about which they are inevitably wrong. A solid relationship needs to be built on a strong foundation of awareness about how you and your co-founder(s) operate. Here are some questions you might explore:

• What are five life experiences that have shaped each of us?

• What are the parts of ourselves we try to hide from the world?

• What is it we value most in one another?

• How would we each define our leadership style?

• How would we each define our communication style?

• How do we each handle conflict? Name some examples.

The Enneagram can also be a useful tool here. Understanding your own type and that of your co-founder(s) can serve as a framework to build awareness, understand core fears and motivations, and unlike other ‘typing’ frameworks which tend to simply attempt to label people, it has a developmental focus that can help provide direction.

Challenges

There’s a lot of optimism in startups but don’t let that obscure the need to talk about inevitable challenges. Having discussions about how you think about the hard times is potentially the single most valuable conversation you can have in the early days. Here are some questions you might explore:

• What are the challenges we anticipate for ourselves?

• What are the challenges we anticipate for our co-founder(s)?

• How do we want to handle conflict when it inevitably arises?

• How will we know when one of us has been outgrown by our role? How should we handle that?

• How does each of us respond to stress?

• What happens if we fail?

• What’s the absolute, worst-case scenario for each of us?

Support

What do each of you need from the relationship (beyond the practical skills your co-founder might bring)? Here are some questions you might explore:

• What is it that we need from one another in terms of support?

• What are the other support structures we each have in place?

• What are each of our ‘tell signs’ that show we’re stressed or in need of support?

• How can we help each other stay motivated?

• How can we help each other balance work with other needs?

• What are the routines we want to build for ourselves around this?

Practicalities

It’s easy to take a lot of the practicalities as given, but there are many important details that will shape your day-to-day that you may think very differently about. Here are some questions you might explore:

• Are we splitting equity equally?

• What about the vesting period? 4 years is typical but would we really want one of us to leave in 2 years with 25% of the company (assuming there’s two co-founders)? What’s the commitment we really want to make?

• How will we split roles and responsibilities?

• Who has which job title?

• Do we plan to work remotely or in-office? How about when the team grows?

• What working hours and patterns do we each prefer?

• How will we make decisions?

• How often shall we meet?

• How shall we provide each other feedback?

3. Be prepared to show up day-after-day for the long haul to navigate challenges and make things thrive

The pre-marital counselling stage does not buy you a pass for the relationship itself. Like a marriage, you’re making a commitment to show up for one another day-in-day-out, for better or worse.

Here are some recommendations to keep the relationship on track:

• Designate regular time to discuss the relationship without getting sidetracked into tactical business stuff - this might be done with the help of a Coach, but if you already have the right foundations around communication and vulnerability then it could be as simple as a monthly session together.

• Keep checking in on high level alignment - you could take all of the questions above and simply add your answers into a google doc. Check back in every 6 months to see what’s changed.

• Do some fun stuff together - some co-founders are very close friends and others aren’t. Either way, find something non-work related to do together.

• Keep working on, and taking ownership of your own stuff - we all project our own stuff onto relationships, it’s just a question of if we’re aware of what we’re doing or not. Part of the job of a co-founder (or a spouse) is to continuously hold their hand up and say, ‘I know I made that about you, but really it’s about me and I’m going to try to do better.’

• Keep communicating - it’s easy to disappear into your own silo and let things fester. There really is no such thing as too much communication in this context. Say the thing.

• Learn how to manage conflict and disagreement - you will disagree. That’s a fact. If you’re telling yourself ‘me and my co-founder are different. We’re always on the same page,’ then chances are you’re already disagreeing but someone isn’t speaking up. And the truth is that a) you should be disagreeing on some stuff, and b) not all disagreement can be ‘resolved’. I see the management of disagreement and conflict as being partly a byproduct of the things listed above (i.e. the more you do the healthier it will be), and partly something you should focus on specifically by building skills and rituals that focus in on it.

So here’s to hoping for that happily ever after, or at the very least a swift and amicable co-founder divorce.

There’s much more to be said here and given the importance of the topic it’s definitely something I’ll revisit in future editions. For now though, I hope that gets you thinking. See the experiment below as an example of how to put some of this into action.

From the archive