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21 December 2021
Lose that cofounder and save your startup
Unsplash © Jilbert Ebrahimi

Lose that cofounder and save your startup

When a business relationship sours, it’s not a relationship worth saving. I’m a total team player. But even after 20+ years and 14 startups, I’ve never been a cofounder. Not once.

Don’t get me wrong. I’m not against cofounding. I’ll say again, I’m a team player. I like having at least one other person to work with on an ongoing basis, someone who understands and is as passionate about what we’re trying to accomplish as I am. In fact, as we grow, I want to surround myself with those kinds of people.

But I also know that leadership, true leadership, is lonely as hell.

When decisions need to be made in the name of an organisation —decisions with consequences that might not go over well with everyone affected but need to be strongly defended and firmly held — those decisions can’t be made by a committee, or by a team, or by a panel.

When big, ugly decisions get made by committee, and you’re lacking buy-in from one or more members of the side that lost the decision-making vote, you’re setting yourself up for potential failure, potential future gridlock, and definite disgruntlement.

And God forbid, if ever one of those committee-made decisions becomes unpopular and one or more representatives of that decision-making body makes it known that they weren’t on board with that decision in the first place, you’ve got yourself a mutiny in the making and chaos in the organisation.

So yeah, I’m not saying that any startup with two or more cofounders is doomed to failure when the chips get low, I’m just saying I get a lot of emails.

My cofounder has checked out, what do I do?

In a recent issue of Teaching Startup (#82), I answered a question about the impending removal of a cofounder who hadn’t “contributed anything” in several years.

While I believe I gave some good answers, not only about how to resolve the equity situation but how to prevent it from happening in the first place, I would say I get that email or have that conversation with a founder about once a month.

Sometimes the person who needs to be removed is a cofounder, sometimes it’s an early angel, sometimes it’s a regular employee. But the situation is always the same. Trust in the beginning leads to the drawing up of documents that outline reward without defining contribution. Then the contribution stops, but nothing stops the timeline of the reward.

Except for a really bad and painful breakup.

Business relationships are like personal relationships, except they’re not

I like talking about relationships because they fascinate me. I don’t have perfect relationships. I have enemies. I don’t have a perfect marriage. My kids don’t think I’m the perfect dad. There are folks I know who I wish I was closer to and I know I’m the impediment.

But I don’t have to be a pro-golfer to show you that you’re gripping the golf club incorrectly and it’s killing your swing.

To hammer the point: Also in this week’s issue, we ran a poll about which areas of their lives entrepreneurs get the most useful leadership lessons. Relationships finished dead last. And I realised that while there are a lot of lessons you can take from personal relationships, there are enough major differences that make leaning on those personal relationships to figure out business relationships problematic.

The disappearing cofounder phenomenon is one of those differences.

One way that business relationships are indeed like personal relationships, especially marriages or other romantic relationships, is that sometimes one person will do anything they can to keep the peace, maybe more than they should.

The difference, especially when it comes to cofounding or other shared decision-making responsibilities, is that in marriages and romantic relationships, there has to be a symbiotic relationship in order to survive and thrive. In other words, if all the decision-making in the relationship is done by one person, the relationship suffers.

It’s the exact opposite with business relationships. Every business needs a leader. So if I’m not the CEO, I will defer to my CEO. Every time. And in some situations, I’m glad I’m not the CEO, and I don’t have to deal with CEO shit. Because when I am the CEO, I understand that it’s my responsibility to make, defend, and carry out the tough, ugly, and scary decisions.

If you have cofounders, one of you needs to be a strong CEO. And if that relationship sours beyond repair, the CEO needs to rip the relationship away like a bandage. A lot of new entrepreneurs, and even some of the experienced ones, go into cofounding without that agreement.

And when that happens, I end up getting one of those emails.

This article was originally published on Medium by Joe Procopio

Joe Procopio is a multi-exit, multi-failure entrepreneur. He is the founder of startup advice project and is the Chief Product Officer of mobile vehicle care and maintenance startup Get Spiffy. You can read all his posts at