I Should Never Have Cofounded a Business
I posted something on LinkedIn a couple of weeks ago that I had been sitting on for a while. A confession, really. That I should never have cofounded a business.
The response took me by surprise a litte. Not the likes or the comments. The DMs. Other founders reaching out saying they had done the exact same thing for the exact same reason or knew someone who had. And none of them had said it out loud before either.
So I wanted to go deeper. Because the post scratched the surface. This is the full story.

The decision I made knowing it was wrong
When I decided to leave employment and start a business, I was excited, nervous, slightly shi$ting it! I do not say that lightly. I had a young family. Bills to pay. A career that was going well enough. The idea of walking away from all of that and betting on myself was exhilarating and paralysing all at once.
So I found a way to make it feel safer. I cofounded.
I told myself it was strategic. Complementary skills. Shared risk. A smarter way to build. And on paper, it made sense. Two people. Two networks. Two brains. Half the exposure.
But that is not why I did it.
I did it because I was scared. Plain and simple. I find that tough to wrestle with at times, but it is the truth.
The worst part is not that I made the wrong call. It is that I made it knowing it was the wrong call. I knew, deep down, that I was solving for comfort, not capability. I knew that the reason I wanted someone next to me had nothing to do with what the business needed and everything to do with what my nerves needed.
They say you should trust your gut. I did not trust mine. And it cost me. Not financially, emotionally and mentally.
What fear dressed up as strategy actually looks like
Here is the thing about cofounding for the wrong reason. It does not blow up immediately. It is not dramatic. It is slow. Quiet. Corrosive.
You start compromising on decisions you would not compromise on alone. Not because the other person is wrong, but because the dynamic demands consensus. Two founders means two visions. Even when those visions are close, close is not the same as aligned.
Energy gets spent managing the partnership instead of building the business. Conversations that should take five minutes take fifty. You start negotiating internally before you even get to the client, the candidate, the market.
And the hardest part is that none of this is anyone's fault. It is structural. It is what happens when the foundation of the partnership is not "we need each other" but "I need to not be alone."
I lied to myself for a long time about this. Telling myself it was working. Telling myself the friction was normal. Telling myself that every cofounder relationship has tension.
It does. But not every cofounder relationship was born from fear. Mine was. And I knew it at the time. That lives with me and to be honest, it does sting a little.
The conversation that made it impossible to ignore
A few months ago, I had a conversation with another founder who had done the exact same thing. Same logic. Same quiet awareness that the real reason was fear.
When he said it out loud, it hit me like a ton of bricks. Because I had never said it out loud myself.
We sat there and just looked at each other. Two people who had built businesses, employed people, generated revenue, created something real. And underneath all of it, the same confession neither of us had made before.
With that also came a sense of relief. Because once you say the thing out loud, it stops owning you.
There is a simple reason founders form deep bonds with other founders. Not because of shared success. Because of shared honesty. The stuff you cannot say to your team, your board, or your partner at home. Another founder just gets it. No judgement. No advice. Just recognition.
That conversation changed something in me. It did not fix anything. But it made me stop pretending.
What it cost me
I want to be specific about this because vague regret is useless.
Cofounding for the wrong reason cost me time. Years of building something that was always slightly misaligned with what I actually wanted to build. Years of energy spent on internal navigation that could have gone into the work.
Mentally and emotionally it exhausted me. By the end of it I was burnt out.
It cost me clarity. When you are managing a partnership that should not exist, you lose sight of your own convictions. You start second-guessing instincts that were right because the dynamic rewards consensus over conviction.
It cost me speed. Thirdway exists now because I eventually did go alone. But it took longer than it should have. The cost of that delay was real. Time. Energy. Complexity that did not need to exist.
I carry that. Not as guilt. Just as honest accounting.
Why this matters beyond my story
I work with founders every day. I sit across from people who are scaling past the point where instinct alone can carry the business. They need their next senior hire to be right. The stakes are real and they feel it personally.
I want to be that open with my clients. It is the whole reason Thirdway exists the way it does. If I am asking a founder to trust me with the most important hire in their business, the least I can do is be honest about my own decisions. Including the ones I got wrong.
Starting a business is lonely. The pressure is constant and the doubt is relentless. And when you are standing at the edge of a decision, any decision, the temptation to find a way to make it feel safer is enormous.
Sometimes that is the right call. Sometimes the business genuinely needs two people from day one.
But if the reason is fear, it is the wrong reason. And you will know the difference. You will feel it in your gut before you override it with logic.
I was not strong enough to go alone when I should have been. Thirdway exists now because I eventually was.
This is not a lesson. I am not wrapping it up with a bow.
It is just the cathartic truth. And it has taken me longer than it should have to hold the mirror up and face it.