Mo’ Founders, Mo’ Problems

Cofounder drama is the secret startup killer

Dall-E/prompt: "watercolor depiction of a modern startup office engulfed in flames. Inside, four co-founders are seated around a table, glaring at each other with evident tension and animosity, while the office blazes around them"

Cofounders—can’t live with them, can’t (usually) build mega-successful companies without them. 

No matter how brilliant a startup’s founders, they are still human and can fall into dysfunctional patterns. While many startups die because they don’t find product-market fit, cofounder drama might be just as big of a cause. Unfortunately, people problems are far more difficult to talk about than product pivots or market conditions—and that makes cofounder conflict the secret killer of startups.

Here are just a few situations that I’ve encountered in my work as CEO/founder of Workflow, a recruiting and talent consultancy for startups: two cofounders at a well-known startup parade their “great friendship” in the press, much like a couple with a meet-cute story. In private, they can’t stand each other—it’s all for show. Or a CEO/founder considers their cofounder deadweight and boxes them into a corner while constantly complaining about their share of equity. 

How you address these conflicts can set the blueprint for how you approach challenges as a company, with your behaviors cascading onto every employee you bring on. When the founders have a healthy, balanced dynamic, the business will as well. So let’s break it down: in the high-stakes drama of startups, cofounder drama is inevitable. How can we solve it? 

The solo (1) founder

The dysfunction loop: Hyper-independence ↔ never figures out how to scale themselves and ask for the appropriate help → eventually crashes and burns out. 

What it looks like
  • Heavy is the head that wears the crown. The solo founder’s brilliance may shine in coding, sales, or fundraising. When it comes to scaling, they quickly get stretched too thin and start to falter. Unless they’re supported by a truly world-class executive team, they’ll inevitably lose oversight over the many parts of the business they’re managing—leading to untenable problems.
  • They likely have an “I have to do everything myself” mindset, sometimes subconsciously. This makes it very difficult for others to offer meaningful feedback, stunting their growth as a leader. Loneliness and stress become a self-created prison. 
  • The company becomes an exact copy of your weaknesses. For example, the technical founder, despite being CEO, puts all of their focus on engineering. As a result, sales and ops stagnate and become the blocker to growth.
  • There is no slack for when stuff happens. Whether it’s a temporary funk, a personal crisis, or sustained burnout, no extra bandwidth means any life event can endanger the business.  
How to make it work: 
  • Focus on the sustainability of your journey. Startups are a marathon, not a sprint. The company needs you to perform at your best, potentially for many years, which means taking good care of your mind and body.  
  • Invest in an extraordinarily strong personal support system. While this is important for all founder teams, it’s the most critical for the solo founder. Some possible ideas: executive coaches, therapists, health and wellness resources (including personal trainers, acupuncture, yoga/meditation), and quality time with family and friends who have nothing to do with the business.
  • Ask for help. Many high-powered people still think asking for help is a sign of weakness. It’s actually a sign of maturity. Ask for help from your team, and tap into existing resources, like peer groups.

Duo (2) founders  

The dysfunction loop: Getting entrenched in a codependent dynamic with rigid roles, which usually results in a power struggle that has too much or too little conflict. 

What it looks like:
  • When the dynamic duo is good, it’s really good—they’re ideally a complementary mix of strengths and weaknesses, built on a foundation of trust that allows the pair to be true partners and grow together. Unfortunately, this is also one of the hardest dynamics to navigate when things aren’t going well. As they say, it’s better to be single than partnered up with the wrong person. 
  • Much like a romantic couple, the duo can get trapped in anxious <> avoidant loops. For example, one founder might be more dominant and the other more passive. Or one founder is focused on fundraising and their public image, while the other is grinding through the day-to-day of the business. Both hold resentments about the roles they play. Again, tension mounts. 
  • Competition for control may show up in unproductive ways. I’ve seen founders divide the business into separate focus areas, and then have proxy fights through those functions (e.g., engineering versus sales). This devolves into more complicated power struggles involving the teams under them.
How to make it work: 
  • Start with all of the above solutions for solo founders.
  • In a duo, a lot tends to go unspoken or get swept under the rug—there’s no third founder to force things to the surface. It’s even more important to carve out time for founders to be honest with each other, air out feelings, and work through conflicts. 
  • The duo’s cycle can get very entrenched, so the key is to interrupt it. Work with a founder coach (I can share referrals). Hire a strong, experienced COO. Both resources, much like a couples therapist, can act as a neutral third party. Ideally, you can invest in this early, before the high-stakes pressure makes the conflict untouchable.

Trio (3) founders

The dysfunction loop: Constant clanning, influenced by the human tendency to organize into “us” versus “them,” leading to insecurity and infighting that distracts from actual building.  

What it looks like: 
  • Much like the “three-body problem” found in physics, the trio is inherently unstable. One is almost always “left out,” while the other two come together. These roles are constantly in flux. 
  • Because one founder is often the “odd one out,” unless there’s an extremely solid foundation (as individuals and as a trio), insecurities are bound to surface. And these feelings, when unacknowledged and unprocessed, lead the “odd one out” to act out.
  • Some signs of unproductive behaviors include more one-on-ones (1:1s) than group conversations, 1:1s that are mostly about venting instead of direct conflict, constant worrying about what “the other person is doing” and playing social games, and trying to “win” the majority to “their” side.
  • Carving up the different focus areas of the business can become even more contentious, and can exacerbate the different levels of skill and commitment that each founder brings to the table. Cap table arguments start to get ugly. 
How to make it work: 
  • Invest in building emotional honesty and security. Institute explicit boundaries around 1:1s. For example, you might agree not to talk about the other founders unless it’s explicitly about work responsibilities or you’re willing to deliver direct feedback from a kind, productive place. 
  • Pay attention to the dynamics, especially because a trio is inherently more complicated than a duo. A duo has just one “pair,” but within a trio, there are three pairs and a triple—each dynamic with its own potential to go off track.
  • In order to counteract unproductive 1:1s from taking over, more time must be carved out for the group. Spend time getting to know each other before you start work. Once the work starts, carve out time for the cofounder team to hang out in non-professional settings. (If you think this sounds like a lot of work, wait until you get to the next section, where the true power of exponential growth kicks in…) 

4-plus founders

The dysfunction loop: Congratulations! Your brand new startup gets to have politics from day one. 💀

What it looks like: 
  • A healthy four-plus person cofounder dynamic is possible—but my experience has taught me that it’s unlikely. The following questions must be addressed early and often: who actually holds the power? How are decisions made? Where is the accountability? Are we avoiding hard conversations that would lead us to realize we don’t actually need six founders? 
  • The dynamic is exponentially more complicated than any of the former, and people end up spending too much time jockeying for positions instead of working on moving the business forward. Clanning and unprocessed feelings can get in the way of productivity.
  • There’s an explicit purpose to the role of a “founder”—it entails taking on the greatest amount of risk and committing to building for the trade-off of future potential rewards. With too many cofounders, power and commitment get diluted (not to mention the cap table). Also, larger groups make it easier for one to be removed by the others—politics, insecurity, and paranoia are even more likely. 
  • With more than four founders, I believe there’s a good chance that ~half will not last for more than a couple of years. Cofounder departures are almost always painful, time consuming, and inordinately expensive. It’s always worth it to address it early (not unlike a prenup), or better yet, stick to 2-3 cofounders in the first place. 
How to make it work:
  • Within a large founder group, there must be a separate layer that holds the stable power structure: a power layer within the power layer. This is most likely to be a strong CEO who is empowered to be the decision-maker, with a clear reporting chain and management capabilities to hold the rest of the group accountable. 

Founders are an extremely ambitious group. But just as you can be proud of your team’s technical prowess or sales chops, it’s possible to be people-smart, maintain strong cofounder relationships, and build an exceptional organization. 

Unfortunately, we—as a startup community—still don’t put enough emphasis on founder relationships. Most advice is still about product-market fit or fundraising, while sticky people problems get swept under the rug. Usually, by the time I’m brought in to a startup to help with cofounder troubles, the situation is pretty dire. It’s frustrating to think about all the lost potential across countless startups that could have gone on to accomplish great things. 

So startup leaders should remember: navigating cofounder conflict is part of the challenge that you signed up for. It’s an integral part of building a successful business. You’re capable of handling it. You just have to start.    

Jennifer Kim (@jenistyping) is the founder and CEO of Workflow, an education and consulting company that trains the next generation of startup leaders on recruiting, people ops, and DEI. She is also a venture partner at Symphonic Capital, and previously was head of people at Lever. She writes a weekly newsletter about the human side of startup building, Safe for Work, where this piece was originally published.

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@mschoeffler 6 months ago

Nice post! Would be very interested in you going deeper on solo founders. Too many gurus advise "find a co-founder" and move on. We're out there and want to maximize our odds.

Jennifer Kim 6 months ago

@mschoeffler Yep! Much like how it's much better to be single than to be married to the wrong person...

Georgia Patrick 6 months ago

What an interesting report from the front lines of founder dreams and conversations. Sometimes the underlying issue is the answer to this question: Before you decided to do this, how did you learn the fundamentals of business functions, roles and structures?

Jennifer Kim 6 months ago

@[email protected] Exactly – it's *always* better to walk through the questions early before going all-in on a company together and uncovering things the hard way!

@ARBullen 6 months ago

Great post! I'd love to read more deep takes on exec dynamics like this, despite how important it is, it isn't something I see people talking about a lot.

Great post!!

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