How not to mess up your co-founded business.

Max St John
The Happy Startup School
8 min readJun 14, 2016

It starts with an impossible dream and a sense of excitement, but it’s normal for things to get tricky or tired. Here’s how to get back on track.

These guys have it nailed — but it doesn’t always feel like this (credit Kristina Alexanderson)

Co-founded businesses are unique — or at least the relationships at the heart of them are.

And like all things in life, that uniqueness can sometimes feel amazing, sometimes tough, and most of the time not recognised at all.

Over the past 10 years I’ve worked in co-founded businesses, and in the past 18 months, I’ve worked with a whole bunch of co-founders, helping them get their relationships and organisations clear and on-track.

While every person, every pairing, and every business is different, I’ve noticed some common threads and stumbling blocks — I thought I’d share them, and how to best work with them.

By no means is this an exhaustive list, and of course every single situation has its nuances and differences. And I certainly don’t pretend to have all the answers. I’d love to hear what your experience has shown you – let me know by response

1. Difference as strength vs difference as difficulty

Cofounders end up together because they’re different. They need each other’s difference.

One might be the ideas person — lively, inspirational, a good starter — but less good at detail and following through. The other might be more meticulous, enjoy routine, listening to what other people have to say before jumping in.

Alone, they lack what the other can bring. And as well as enjoying the company of their co-founder, they’ve gravitated towards them because they need them to fill the gaps.

The trouble is, at some point in the relationship this difference surfaces as tension — what one lacks and the other possesses can lead to frustration, or fear.

“Why are you always like this!” or “I’m really not sure we’re on the same page any more.”

This usually happens at times of stress — when the business has grown, and it feels like there’s more at stake. Or if things seem to have gone off-track, and you don’t know where they’re headed.

How to deal with it:

Get back to the why. Take time to remind yourselves why you started this thing. What you were trying to achieve together. This is what gets lost along the way, and revisiting it can help you both feel like you’re back on the same team.

Make more time to talk, away from the team. Remind yourselves that you’re together because of your difference and that’s exactly what’s most valuable about any difficulty you’re experiencing.

And in the moment of conflict, bring your attention to the issue at hand — and away from the other person and/or their behaviour. Put the decision or problem at the centre and welcome any disagreement.

2. Doing it yourselves vs asking for help

Many co-founders started early, and started together. They might have met at University over an idea they worked on together, or after their first job, suddenly realising that they’d rather be working for themselves.

So the ball starts rolling, things pick up and before you know it, it’s ten years down the line. You’re managing a team, you have an office, you have clients and with all this, a whole heap of pressure.

From being able to focus solely on the ‘what’ or the ‘why’ of the business, suddenly all your attention turns to how.

What’s your role? What’s mine? Is there a better way to structure this thing?

It usually starts with noticing patterns — unhappy staff, issues with communication, a big project going awry, or feeling like you’re hitting a glass ceiling in revenue or impact.

The temptation is to try and think your way out of it alone.

When there’s two of you, it’s common to believe that between you, you must be able to come up with the solution. But without having done this before (as if anyone has), and being completely ‘in it’ for so long, this is a dangerous trap to fall into.

Especially in creative businesses, the temptation is to try and design your way out of it — but more often than not, you’re going to be reinventing the wheel, and for all the wrong reasons.

How to deal with it:

The smartest people I work with ask for help. You’re probably surrounded by people in your immediate network who’ve been in this situation, or who’ve worked with others that have.

Don’t be afraid to bring someone in (I would say this, of course — it’s my business), because you really can’t see it from the outside when you’re in. And so much of your very personal needs and identity is mixed up with everything about the business. Even the best critical thinkers can’t see past their own stuff.

Be open, be vulnerable, be humble. Get out there, start asking and looking. But don’t swallow everything you see or hear wholesale either — look at it with curiousity and a critical eye.

3. Agreeing on everything vs making clear decisions

Because you start out as friends, equals and business partners fully invested in the idea, you work closely together.

To start off with it’s just the two of you, and you’re able to sit down and make all the decisions together, big and small.

You make the time to talk it out and come to an agreement that you’re both happy with. There’s no one else to consider, or expectations to manage, and it feels easy and light to run this thing as partners.

But as time goes by, there are more decisions to make, and less time to sit down and talk about it.

At some point, you find major decisions not being made because you can’t come to a consensus between you, or find the time to get to the bottom of why because the team are always around and there’s always so much to do.

How to deal with it:

Get very clear who is responsible for what. And no, you can’t both be equally responsible for anything. Someone always needs to take point, and have the final say on a given decision.

Learn to give and take responsibility for the major initiatives and projects in the business. Know what is ‘yours to do’ and what’s not — ask: “Who started this?” Find out who had the vision and the need, who made the first move.

And get comfortable with disagreeing (see 1.), but know that a decision has to be made.

Regularly make time to talk properly, get advice and input where needed, but learn to ‘disagree and commit’. If you’ve been listened to fully, and your co-founder still wants to go the other way, give them your full support.

And if you’re the one making the decision, and your partner’s dissent leaves you feeling a deeper sense of doubt or concern, maybe it’s time to stop and reflect before you charge on.

HEALTH WARNING: as pointed out by a friend and ex-co-founder, sometimes you also have to fight tooth-and-nail for what you believe in, even if it’s supposedly not your decision to make. This comes right back to valuing disagreement and embracing difference. Learn to know when to let go, and when to be prepared to be like a dog with a bone.

4. Stuck in a rut vs shooting for the moon

It’s so easy for co-founded businesses to hit a comfortable-but-uncomfortable rut — things are going ok, but it’s not exactly clear where they’re going. You know what your doing, but you’ve kind of lost sight of why.

And rather than feeling that sense of energy, motivation and creativity, it feels like more of a routine plod towards something undefined.

At the beginning it was clear — you had an idea and you were going to turn that into a business. Nothing more complicated than that.

Every new client, every sale, every new hire — each was an adrenaline hit that told you things were heading in the right direction.

But as that idea becomes reality, what was once a crazy dream that set you apart from the rest can become something more mundane. And lacking that initial clarity and challenge-in-the-face-of-adversity, you’re feeling a lack of focus.

And while you might find some comfort in the routine, or in the security that comes with having an established outfit, the lack of challenge and focus can feel like a threat — with nothing to evoke that same sense of excitement and energy, you might worry how things are going to pan out.

How to deal with it:

Again, get back to your why. Take time out to remind yourselves what was driving you to do this in the first place.

Most businesses (certainly those founded 10+ years ago) didn’t spend time thinking about purpose when they were starting up, but yours is there if you look hard enough.

Re-tell yourselves the story of how you came to be together, and when you decided to take that risk and go for it. What was the impact you wanted to have in the world? What’s it all in service of?

Spend time thinking and talking about your individual needs too —unless this thing is working for both of you, and you’re taking responsibility for that, it’s standing on shakey foundations.

And from purpose and needs, work out your vision of the future — what does life look like in 5, 10, 20 years time? What makes you both feel alive? Use this to refocus your energy, projects, roles, people towards something you really want, and redisover that startup feeling.

A final checklist (or tl;dr)

In summary — co-founder relationships can be an awesome force for acheiving inspiring goals, or turn into kind-of friendly, slightly resentful ploddy businesses that go through the motions.

If things have gone a little south, here’s your checklist:

  1. Spend more time together: nothing can replace face-to-face, honest conversation. It’s more important than anything else you’ll do.
  2. Value your differences: it’s why your together and what makes you an awesome partnership. Embrace it.
  3. Ask for help: don’t expect yourselves to have all the answers, just because there’s two of you. Look outside.
  4. Map out responsibility: know who’s responsible for what (based on who initiated), keep each other informed but don’t consult each other on everything.
  5. Disagree and commit: if you know who’s responsible for what, give them power to make the decision, and support them, even if you disagree (except when you really can’t).
  6. Reconnect to purpose: find the thing at the core of what you do. Make it very clear, and keep coming back to it.
  7. Map out your needs: know why you’re both in this thing and what you want out of it (and no, it’s not money).
  8. Create an inspiring vision: paint a motivating picture of the future and align everything you do towards achieving it.

So, this is my take on it. What’s yours? Are you a cofounder? Have you found things have gone off track? Or successfully got your business fired up again. Let me (and everyone else) know in responses.

My name’s Max. I help people create a meaningful life through work, and build inspiring businesses where everyone matters and belongs. If that sounds appealing, you should probably get in touch.

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Max St John
The Happy Startup School

I teach people how to navigate conflict and have conversations that matter. www.maxstjohn.com