Kindergarten CEO
We started as the perfect trio. Classic founder setup: business guy (me), technical guy, and partnerships/relationships guy. On paper, it looked like we had all the bases covered.
In reality, I became a fucking kindergarten teacher.
They argued about everything. And I mean everything. Should we use Slack or Discord for team chat? Three-hour argument. What color should the logo be? Two days of passive-aggressive Figma comments. Whether to order lunch for a client meeting? Somehow became a philosophical debate about company values.
The breaking point was a Tuesday morning when I walked into our shared workspace to find them in a heated argument about... I shit you not... whether we should have assigned parking spots. We were three people. With two cars between us.
I'm sitting there thinking, "We have eight weeks of runway left, our biggest client is asking for features we can't build, and you two are discussing parking logistics for a problem that doesn't exist."
The worst part? They both kept pulling me into it. "Tell him he's wrong about the API structure." "You need to talk to him about respecting boundaries." I became the mediator for disputes that made no sense.
I realized I was spending more time managing their relationship than actually running the company. Every decision required me to navigate their personal dynamics. Product roadmap meetings turned into therapy sessions. Board updates included a section on "team harmony initiatives."
The technical guy was brilliant but treated every suggestion like a personal attack. The partnerships guy was great with people externally but couldn't handle internal conflict. And me? I was slowly losing my mind trying to keep the peace while watching our company stagnate.
We eventually had to make a choice: fix the dynamic or split up. Two of us stayed, one left. The company survived, but barely. Those three months of constant firefighting cost us momentum we never really recovered.
Nobody warns you that cofounder relationships are harder than marriages. At least with a divorce, you can split assets and move on. With cofounders, you're stuck trying to build something together while they bicker about whether the office plants need more water.
I learned that complementary skills mean nothing if personalities clash. All the talent in the world can't overcome two people who fundamentally can't stand each other's working styles.
The hardest part? Explaining to investors why we were behind on milestones. "Well, we spent most of last month resolving a philosophical disagreement about commit message formatting."
Yeah, that goes over well.
