The Best Companies Are Dictatorships

Everyone wants democracy until they see what it builds

The founder walked into our product review, looked at the PRD we'd spent weeks perfecting, and ripped it in half.

He drew what he wanted on the whiteboard. Three boxes. Some arrows. Then he left.

The room sat still. Senior engineers stared at each other while the torn pages uncomfortably settled on the conference table. As the PM, it was my job to turn those boxes into reality.

That's when I learned the truth about the best companies. They're dictatorships. We just pretend otherwise.

But let's be clear: benevolent dictatorships, not tyrannies. The difference matters. Tyrants crush spirits and hoard power. The best founders are unreasonable about product, deeply reasonable about people. They'll debate pixels for hours but also notice when someone's struggling. They demand excellence while building psychological safety.

We already have enough founder worship. What we need is honest recognition of what actually works.

Years earlier, I'd sat in a product meeting at a "collaborative" company. Eight executives pushing their agendas for an hour. Circular debates about priorities that produced nothing but calendar invites for follow-up meetings.

I wanted to scream. Just tell me what matters. Make the damn decision.

That torn PRD suddenly made sense. I'd rather have a founder who knows exactly what they want than eight executives who can't agree on anything. Direction beats democracy every time.

Why Product Leaders Never Last

Watched a CPO join a unicorn to "establish order during wartime." Great resume. Previously scaled product at a public company. Thought he was going to professionalize the chaos.

Six months later, gone.

His mistake? He thought the founder wanted a partner. The founder wanted an executor. Non-founders never get reps at high-stakes decisions. They can't rise to the occasion because they've never had the ball when it mattered.

This happens every 18 months at every founder-led company. The founders who build empires don't delegate vision.

The Uncomfortable Truth

Working for these unreasonable founders creates more impact than being employee #50 at a democracy.

I've worked on landing pages where the founder spent three hours debating H1 vs H2 tags. The font weight of a single word. The exact character count of a headline. He drew 100 variations himself, each slightly different, refusing to A/B test because he "knew" which one would work.

The team thought he was insane. The page converted at 3x industry standard.

That's the thing about unreasonable people. They're often right. They obsess over pixels because their entire vision lives in the details. Democracy dilutes that obsession into compromise.

These founders operate at a different clock speed. While teams debate, they've already built five versions in their head. Normal pace feels like death to them.

What I Hate Admitting

I want to be the king. Set the vision. Have others execute my ideas.

Instead, I'm a knight at best. Usually a pawn. Building someone else's dream while mine stays in my head.

That stings. It also taught me more than any role where I had "strategic input." Executing someone else's vision at the highest level requires just as much creativity. You just don't get the credit.

People tell me I'm drawn to "tough" founders. The ones others find impossible, I find easy. These founders aren't difficult. They know exactly where they're going. Our job is to build the boat to get them there.

Jensen has 60 direct reports. Not because he loves meetings but because he can't let go. Jobs never hired a Chief Product Officer because he was the Chief Product Officer. Enzo Ferrari made engineers wait hours while he adjusted the curve of a fender that already looked perfect to everyone else.

They all fail the normal management test. Can't delegate. Obsess over details no one else notices. Override best practices. Make decisions that horrify MBAs.

They also build the companies that matter.

You can't committee your way to caring about every pixel. Someone has to be unreasonable enough to see what others miss. That someone is usually the founder.

Choose Your Kingdom

Every employee wants the same impossible thing. They want Brian Chesky's product sense but also want their product opinions heard. They want Jensen's technical excellence but also sustainable work-life balance.

The founders won't change. This isn't a bug in their operating system. It is THE operating system.

But not every founder who can't delegate deserves followers. Some are just bad managers hiding behind "vision." The ones worth following combine unreasonable standards with unusual care for their people. They're rare.

Stop pretending you want democracy when what you actually want is to be part of something exceptional. Either find a founder whose obsession matches your ambition, or go build your own kingdom.

Once you've worked for someone who knows exactly where they're going, everything else feels like wandering.

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Thank you to Anil Varanasi, Ethan Ding, Elias Torres & Akshay Kothari for providing inputs to a draft!