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The Wrong First Decision

  • Writer: Jeff Cunningham
    Jeff Cunningham
  • Apr 8
  • 6 min read

They came in prepared. That’s what made it interesting.

 

Most founders who sit across from me at the beginning of a business relationship have done some thinking. They’ve talked through the vision, divided up the roles, and made peace — or something that feels like peace — with how ownership will be split. The more thoughtful ones have gone a step further. They’ve decided who has final say. Fifty-one percent to one partner, forty-nine to the other. Or some version of it. They present this as the hard conversation they’ve already had, the evidence that they’re serious people who’ve thought this through.

 

I let them finish. Then I ask them something they haven’t thought about.

 

What happens when you disagree about something important — not a small operational call, but something that goes to the heart of what this company is supposed to be — and the person with fifty-one percent is wrong?

 

The room changes.

 

Not because the question is unfair. Because they realize, in real time, that the percentage was never an answer to that question. It was a way of not asking it.

 

The Percentage Is Not the Foundation

It feels like the foundational decision. It produces a number, which makes it feel concrete and resolved. But ownership percentage is actually question three, maybe four. The questions that have to come before it — how will we decide things when we disagree, and how will we leave if we need to — are harder to sit with, which is precisely why founders avoid them.

 

This is not a failure of intelligence. It’s a coping mechanism. Imagining conflict before the company exists requires founders to hold two things simultaneously: genuine excitement about what they’re building, and honest acknowledgment that it might not work, or that the partnership might not survive it. Most people can’t sustain that tension for long. So they reach for something that feels like resolution. They land on a number.

 

The problem is that a percentage without a dispute resolution mechanism is a loaded gun with no safety. The majority partner has the theoretical power to decide anything — but exercising that power over a meaningful disagreement will likely end the partnership, and possibly the company, regardless of what the cap table says. The percentage is not an operating system. It’s a last resort that, if it ever gets used, usually means something has already broken.

 

The First Decision: How You’ll Disagree

The dispute resolution mechanism is the actual foundation. It’s the thing everything else runs on.

 

This doesn’t have to be complicated. It can be a defined escalation path — first the partners discuss, then a neutral third party is consulted, then a specified process governs if resolution still isn’t reached. It can include a professional mediator engaged by agreement, or a structured buyout trigger if the disagreement is irreconcilable.

 

What it should not rely on is the trusted mutual friend both partners have in mind — the one they’re certain would be fair, who hasn’t been asked, isn’t a party to anything, and may simply decline when the moment arrives. That instinct is understandable and almost universal. The mechanism it produces is not a mechanism at all. It’s a hope dressed up as a plan.

 

The specific structure matters less than the fact that it exists and that both partners agreed to it before they needed it. What the mechanism does is change the nature of disagreement inside the company. Instead of every significant conflict carrying existential weight — is this the moment the partnership breaks? — founders can disagree within a container they’ve already built. The argument is serious. The relationship doesn’t have to be at stake every time. Partners who’ve done this work argue differently. There’s less performance, less posturing, less fear underneath the disagreement. They know how this works because they decided in advance.

 

The other thing a dispute resolution mechanism does is make the percentage conversation more honest. When founders know how they’ll handle conflict, the ownership split stops being a proxy for control and starts being what it’s supposed to be — a reflection of contribution, risk, and genuine agreement. The number gets easier to arrive at once it doesn’t have to carry so much weight.

 

The Second Decision: How You’ll Leave

This is the section most founders most want to skip, and the one I insist on most.

 

There is a scene in almost every spy film where the hero walks into a room — a party, a meeting, an unfamiliar building — and does something the other people in the room don’t do. They identify the exits. Not obviously, not anxiously, just as a matter of discipline. They note where the doors are, which ones are likely locked, which one they’ll move toward if something goes wrong. Then they proceed to enjoy the party.

 

Everyone else just walks in and starts enjoying the accommodations.

 

When the threat arrives — and in spy films it always does — the difference is decisive. Everyone else becomes a reactive victim, scrambling in the chaos. The hero moves. Not because they’re braver, but because they already made the decision. The plan existed before it was needed, which means when it’s needed there’s no hesitation, no panic, no negotiation under pressure. And there’s something else: that preparedness is visible. It produces a calm that the people around the hero can feel without knowing its source. In a crisis, the hero doesn’t just have a plan. They steady the room.

 

Founders who’ve built their exit mechanics before they needed them have the same quality. They know what triggers a buyout. They know how the company will be valued at the moment of exit. They know the timeline, the terms, the sequence. They’ve agreed on all of it while they still liked each other, before anyone had a grievance, before money was on the table in a way that changes how people think and speak and remember.

 

This is what lawyers call a buy-sell agreement, and it is not a pessimistic document. It is a confident one. It says: we believe in this enough to protect it. We’re serious enough about the partnership to define how it ends, because the definition of how it ends is what makes staying feel like a genuine choice rather than a trap you can’t see your way out of.

 

Founders who don’t have this — who’ve never named their exit — discover its absence at the worst possible moment. A disagreement becomes a standoff. The standoff produces lawyers. The lawyers produce costs. The costs produce resentment. What could have been a defined, navigated separation becomes litigation, or something close enough to it that the distinction stops mattering. All of it, most of it, was avoidable. Not because they needed to have predicted the conflict, but because they needed to have built the door before they needed to use it.

 

Now Talk About Percentages

With those two decisions made — how you’ll disagree, how you’ll leave — the percentage conversation becomes something different. Easier, usually. More honest, almost always.

 

The ownership split no longer has to carry the full psychological weight of the partnership. It doesn’t need to answer the question of who wins when things go wrong, because that question already has an answer. It doesn’t need to encode control, because control has been addressed in the governance structure. It can be what it should have been from the beginning: a number that reflects what each person is bringing, what each person is risking, and what both people genuinely believe is fair.

 

Founders who’ve done this work arrive at their percentage with less posturing and less anxiety. The number they land on tends to hold. It doesn’t get relitigated every time there’s a disagreement, because disagreements have their own container now. It doesn’t become a grievance, because leaving has a defined path.

 

The document, when it finally gets drafted, reflects an agreement that was actually made — not a negotiation that was deferred.

 

 

In twenty-six years of doing this work, I have rarely seen a well-governed partnership end in litigation. That’s not because well-governed partners never disagree. They disagree constantly, sometimes bitterly. What they don’t do is disagree without a framework, which means the disagreement stays a disagreement rather than becoming a war.

 

The founders who skip the first two decisions because they’re uncomfortable — who come in with their percentages ready and their optimism intact and their conflict mechanisms unbuilt — are not naive. They’re human. The future feels real and the problems feel hypothetical. But the problems have a way of arriving anyway, and when they do, the question is whether the partnership was built to handle them.

 

The percentage is not the foundation. It’s the finish line of a conversation most founders haven’t started yet.

 

Start there.


 
 
 

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