When I first started working with how a fight with my co-founder almost cost me my startup, I thought I had it figured out. I was dead wrong.
We were friends who started a company together. This is the story of how missing a simple clause in our founder agreement almost ruined everything and what you need to do to avoid the same mistake.
The Framework That Actually Works
I'm going to share the exact framework I use when evaluating how a fight with my co-founder almost cost me my startup. It's not complicated, but it requires discipline.
Step 1: customer feedback is the only metric that matters This is where most people go wrong. They skip this step entirely and jump straight to execution. Don't do that.
Step 2: the best solutions are often the simplest ones Once you have the foundation right, this becomes much easier. I've watched founders struggle with this for months when the answer was staring them in the face.
Step 3: Iterate relentlessly Nothing works perfectly the first time. The companies in my portfolio that nail how a fight with my co-founder almost cost me my startup are the ones that treat it as an ongoing process, not a one-time project.
What I've Learned From 105 Companies
After investing in 200+ startups and running two companies to successful exits, I've developed a pretty clear picture of what works with how a fight with my co-founder almost cost me my startup.
The biggest misconception is that you need to most founders overthink this and underspend on execution. That's backwards. The companies that win are the ones that the best solutions are often the simplest ones.
I remember sitting with the Anthropic team early on and discussing how they thought about how a fight with my co-founder almost cost me my startup. Their approach was counterintuitive but brilliant.
The Reality Nobody Talks About
Most people approach how a fight with my co-founder almost cost me my startup with assumptions that made sense five years ago. The world has moved on. When I look at my portfolio companies, the ones that succeed are doing something fundamentally different.
The first thing to understand is that the best solutions are often the simplest ones. I've seen this play out across dozens of companies. The pattern is unmistakable.
At RemoteTeam, we learned this the hard way. We spent months going down the wrong path before realizing that the market doesn't care about your roadmap. Once we made the switch, everything changed.
What I Tell Founders
When a founder in my portfolio asks me about how a fight with my co-founder almost cost me my startup, I usually start with three questions:
- What's your timeline? Because the right approach for a company with 6 months of runway is very different from one with 3 years.
- What have you already tried? Most founders have tried something. Understanding what didn't work is often more valuable than knowing what might.
- Who on your team owns this? If the answer is "everyone" or "no one," that's your first problem to solve.
These questions seem simple but they reveal a lot about where a company actually stands.
This connects to broader themes around founder agreements, startup law, co-founder conflict that I've been thinking about a lot lately.
Wrapping Up
I've shared a lot here, and I know it can feel overwhelming. But here's the thing about how a fight with my co-founder almost cost me my startup: you don't need to get everything right on day one. You just need to get started and keep improving.
The founders in my portfolio who excel at how a fight with my co-founder almost cost me my startup share one trait: they're relentlessly practical. They don't chase perfection. They chase progress.
That's the mindset I'd encourage you to adopt. Start where you are. Use what you have. Do what you can. And keep pushing forward.
As always, I'm rooting for you.
Frequently Asked Questions
Do all experts agree with this view?
No, and that's fine. The best ideas in business are often contrarian. I share my perspective based on my experience and data, but I encourage you to seek out opposing viewpoints and form your own conclusions.
What experience informs this perspective?
This perspective comes from over a decade of building companies in Silicon Valley, two successful exits (RemoteTeam to Gusto, MovieLaLa to Gfycat), and investing in 200+ startups including Anthropic, OpenAI, and Scale AI. I write about what I've lived.
What's the most common pushback you get on this?
People often push back by citing exceptions or edge cases. And they're usually right that exceptions exist. But building a strategy around exceptions rather than patterns is a losing game for most founders.