Twenty Years Was the Due Diligence

Everyone tells you the same thing when you say you are starting a company with your best friend.

Do not.

They say it with real concern, usually from experience, sometimes from a scar. And they are not wrong to worry. The numbers are genuinely brutal. A Harvard Business School professor named Noam Wasserman spent years studying why promising startups collapse, and found that 65 percent of them fail not because of the product or the market, but because of conflict between the founders (https://www.entrepreneur.com/leadership/harvard-business-school-professor-says-65-of-startups-fail/370367). Not the idea. Not the money. Each other. And when the founders started out as friends, the fall tends to take the friendship down with the company.

So when Mike and I decided to build Cause of a Kind together, we were, on paper, walking straight into the most common way this whole thing dies.

We had known each other for almost twenty years by then. We had hiked mountains together, been outdoors together, watched each other grow up and mess up and figure it out. We were friends long before we were anything with a title. By every piece of conventional wisdom, that shared history was the liability. The thing that would make the hard conversations too hard, the honest feedback too dangerous, the disagreements too personal to survive.

Here is what I have come to believe, years in, and it is close to the opposite of the warning.

The friendship was not the risk. It was the reason it worked.

Because here is what nobody tells you about those brutal founder conflicts. They almost never come from too much honesty. They come from too little. From the hard thing left unsaid because saying it felt like it might break something. From two people quietly resenting each other because neither one felt safe enough to just say the true thing out loud. That 65 percent is not really a story about people who fought. It is mostly a story about people who could not afford to.

Mike and I could afford to. That is what the twenty years actually bought us. Two decades of friendship is two decades of learning how to disagree with someone and still be there in the morning. Of having already tested, long before any company existed, whether this was a person who could hear a hard truth from me and not make me pay for it later. That was the real due diligence, and we had done it without ever calling it that, on trails and over years, back when there was nothing at stake but the friendship itself.

So when the business got hard, and it did, we already had the one thing you cannot install after the fact. We could say the brutal, necessary, unflattering thing to each other, because we both already knew the relationship was bigger than any single conversation inside it. The honesty did not threaten the friendship. The friendship was what made the honesty survivable.

And I will tell you where that shows up now, because it is not abstract. It leaks into everything. When you build a company out of a real relationship, the company starts to behave like one. You end up caring about the people you build for a little more than the spreadsheet strictly justifies. You refuse to hand a client off to a stranger, because handing people off to strangers was never how either of us was taught to treat anyone. The way two founders treat each other quietly becomes the way the whole company treats the world. Ours was built on twenty years of not letting each other down, and it turns out that is a hard habit to switch off at the office door.

So here is the wisdom, and it might be the most important one I have offered in any of these.

Who you build with matters more than what you build. Almost everyone gets this backwards. They pour everything into the idea, the plan, the pitch, and treat the relationship as the easy part, the thing that will surely take care of itself. It will not. The idea will change five times. The market will humble you. The only thing that determines whether you are still standing at the end is the trust between the people who started, and trust is not a document you sign. It is a history you accumulate, usually long before you knew you would ever need it.

Invest in your people like they are the infrastructure. They are.

If reading this brought one person to mind, the one you could build anything with, or the one you already did, or the one you lost to a partnership that went wrong before either of you ever learned how to have the hard conversation, then you already understand the whole thing.

The idea was never the hard part.

The person you trust enough to do it with is the rarest asset you will ever find.