Co-Founder Calamities

Who to start, and not start, a new venture with

You’ve worked side-by-side with someone for over a year: iterating over and over again until you have your MVP, bootstrapping your way to your first users and revenue, arguing over how to best present your app in the stores, working all-nighters to get your investor deck just right, networking from coast to coast.

And just when the pressure reaches a new height, the little grievances compound and you’re contemplating ending the whole thing before your startup rocket ship has a chance to take off.

That is only one scenario, and unfortunately, tales of warring co-founders are not rare. In fact, it’s alarming how often conflicts end up happening between people who team up to tackle something that requires significant effort, coordination and understanding to be shared.

When looking at statistics for marriage in the U.S., where between 45–50% of couples will divorce, and comparing a marriage to a co-founder relationship, it kind of (sadly) makes sense.

A Tale of Two Alans

Alan Sartirana and Alan Miller founded music magazine Filter. They parted ways in 2014.

“All marriages aren’t meant to last forever. We were fantastic partners for a long period of time and we got to a point where we had different visions.”
-Alan Miller, Billboard

Filter died, and the staff split up between Anthemic and Culture Collide.


Garry Tan, who co-founded Posterous in 2008, realized that he had a problem hiding in plain sight when explosive growth flatlined a couple of years later.

Here he writes honestly about why his relationship with his co-founder faltered:

When things were going well, we were too busy keeping the site online to have anything to disagree about. I learned the hard way that if you haven’t prepared for conflict in your co-founder relationship, you’ll be at each other’s throats right at the moment when you most need to be working well together.
-Garry Tan, Feb 18, 2017



Enough said.

There was so much feuding and backstabbing that it’s a miracle the social network startup became the phenomenon it did.

It Doesn’t Always Have to End Badly

Oswald Yeo, a founder of Glints, wrote here about how he and his co-founders took the high road when bringing their partnership to a close.

If founders take the time to talk through issues rather than allow every discussion to devolve into a battle, there is usually a good chance that an amicable solution can be discovered.

If all else fails, there is actually co-founder counseling offered by companies like the Colorado-based company Reboot.

The Conflicts

Getting to the root of the matter usually happens too late. However, learning about potential issues before you even pick co-founders might help you in the long run.

Who does the most:

The theme of “equality” is a huge one in co-founder relationships. In a majority of situations, one or more of the founders tend to either physically put in more effort (long hours coding, hitting the pavement chasing leads or customers or investors). In a 2-founder group, having a big disparity will create a lot of resentment. If it’s a 3 or more founder group, there could be another situation. It’s not about 2 people doing a lot more work than another. It’s really that that other person is doing LESS. Maybe their function isn’t really needed or can simply be done by a part-time contractor or outsourced.

Who makes the final call:

Being in a 2-founder company can be much more difficult than at first glance. 50/50 power leads to the inevitable stalemate. And 3-founder situations, though they offer the “tie-breaker”, can end up in disagreements that are extremely protracted as founders vie for the favor of said tie-breaker.

This town isn’t big enough for the two of us:

Your personalities may be too misaligned, or you find yourselves in a disagreement so big that the chasm between you is too deep and wide to ever cross. You may have been working at cross-purposes for months, or even years, doing untold harm to your venture in the process.

Outside lives, inner turmoil:

A divorce. A death in the family. Having to put a kid through college. A bout of depression. These are all major things in someone’s life, and their effects can be amplified when compounded by the stress of running a startup. Or maybe it’s internal to the business, as a feeling of unfairness when it comes to equity split, workload, or compensation. They mean a lot to the individual, but shouldn’t be allowed to bring down a multimillion-dollar venture that dozens, or hundreds, of people, might be relying on.

Trust dies hard:

It can be personal or strictly business-related, but this is where one founder no longer feels like she can rely on another. Someone might lose or destroy important material or code or even sell it to a competitor. They might be guilty of fraud or embezzlement. They might be cheating on their spouse…with your spouse. This could result from the resentment caused by other problems in this list.

Falling apart:

When all the KPIs are constantly improving and investors are being pulled toward your startup as if you possessed some cartoon super-magnet bought from the Acme Corporation, you and your co-founders may be too busy and/or too happy to bother pursuing arguments or figuring out “little” problems. This period where everyone has their rose-colored glasses can be a breeding ground for those tiny squabbles and resentments to multiply and grow. When the light is brightest, the shadows are darkest — making it easier for scary things to hide there.

So who do you choose to enter the Thunderdome with:

Knowing that they will be your ally, someone who you need to depend on and who must depend on you…

But also knowing that, at the same time, they have baggage and life problems of their own, and you might end up having to face them as an adversary?

— If you have been friends for years and years, and you do not want to risk losing that person as a friend for anything, you should reconsider. Unless you’ve already been through some level of hell with them and come through just fine, you have to realize that co-founding with them could lead to the end of your valued relationship.

— If you have heard numerous rumors about serious personality clashes or workplace harassment or other concerning behavior, you should be wary. In short, vet your potential co-founders like you were hiring for the CIA.

— If their skill set does not complement yours and merely copies it, you might want to reconsider. Are you a creative genius that needs a tech guru? Find your tech guru, and make sure they are amazing with the tech you want to use. Conversely, make sure they are not only “okay” with some of the techs but also have real aspirations to do the creative work that is your specialty. There might be instances where this could work, but like Jobs/Wozniak it is usually best to assemble a core team of superstar players that excel in different positions on the field.

— Girlfriends/boyfriends/spouses/intimate partners/significant others etc. This can work and has, but it adds another layer of potential conflict, drastically multiplying the number of variables that could go wrong.

What you need

In the end, your co-founder team has to all share a high level of commitment to the business, and, by extension, to each other.

There has to be respected: mutual, for one another, and also respect for the people you are serving with your business.

You must all want the same thing for the company, understand that vision and agree on a strategy to achieve it.

And all of the founders should know how to unwind and leave the work issues at work, at least occasionally, in order to keep from imploding. There need to be pressure-release valves for everyone on your team.

There’s no perfect formula for finding the best possible co-founders.

However, you can arm yourself with knowledge and take precautions where possible, and boost your odds of success.

Thank you for reading and sharing.

This story is published in The Startup, Medium’s largest entrepreneurship publication followed by +414,678 people.

Subscribe to receive our top stories here.