Mo’ Founders, Mo’ Problems

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.