Complexity Kills

This is a true story about two companies that made very different choices about how to handle complexity. I know it’s true because I worked at both.

Each was trying to grow, serve customers better, and scale. But they responded to complexity in opposite ways. One met it with clarity and constraint. The other met it with technical intricacy.

Both believed they were making smart choices. Only one built something that lasted.

This is a story about how real companies build real systems, and what happens when they choose to either reduce complexity, or let it grow.

Company A: Focused, Functional, and Quietly Massive

Company A didn’t look impressive at first glance. Its website was plain. No personalization engines. No animations. No clever UX flourishes. Just a stripped-down interface that let customers find what they needed and order fast.

What powered that experience was even more surprising: much of Company A’s internal systems ran on software written decades ago, including core tools built in MS-DOS. There was no push to modernize for its own sake. If something worked, it stayed.

This simplicity ran deep. The company kept a vast physical inventory, organized so precisely that staff could find parts in minutes, often seconds. Most orders shipped the same day, usually within 20 minutes. Customer service wasn’t outsourced or scripted. It was handled by people who knew the products and could source items beyond the catalog if needed.

Company A has almost no reputation or awareness outside of its core customers, yet they keep coming back. In 2024, the company reportedly brought in over $1.4 billion in revenue. No viral campaigns. No big launches. No AI. Just quiet, consistent competence.

Company B: Sophisticated, Data-Rich, and Fragile

Company B went the other way. It built its business around optimization. Its platform matched customers to insurance plans with mathematical precision. The infrastructure was exceptionally sophisticated, designed by top-tier engineers and data scientists.

Personalization was everything. Customers were split into dozens of micro-segments (e.g. Suburban New Jersey Housewives), each receiving slightly different experiences. The goal was nuance, subtlety, accuracy.

But inside, complexity turned into confusion. The CTO often joked that no one understood the system end to end. Engineers took six months to ramp up. Simple changes meant untangling a mess of interdependencies. Promising ideas died not from failure, but from the impossibility of alignment across siloed systems. Initiatives to “simplify everything” came and went. Nothing stuck.

Company B was a buzzy success story after getting acquired for just under $3 billion. Five years later, it was shut down by its parent company. The official reason was “strategic realignment” in response to changing industry regulation. Internally, everyone knew the truth: they couldn’t pivot. The complexity of the system they built wouldn’t allow it.

Why Do We Mistake Complexity for Intelligence?

We’re drawn to complexity. We assume someone smart must be behind it. We treat intricate systems like signs of genius. A dense presentation appears more credible than a simple insight. A product with 400 features seems more advanced than one with four. We rarely ask whether those features make anything better.

Some of this is insecurity. Simplicity feels naive, like something we should have outgrown. If something looks easy, we assume it must be wrong or incomplete.

Some of it is ego. Complexity flatters the builder. It creates insider knowledge, tribal language, gatekeeping. Simplicity threatens that. If it’s too clear, then anyone could have done it.

And some of it is cultural. In tech, invention is seen as progress, even if it adds friction. Subtraction is harder to celebrate. It often feels like taking away someone else’s win. But it’s the real work. Making something simpler, without making it worse, takes deep understanding. It means knowing exactly what to cut. It means resisting the urge to impress, and choosing instead to serve.

Anyone can make something complicated. Simplicity, especially at scale, takes discipline. It takes expertise. And it takes humility.

These companies made different choices. One chose clarity over cleverness. The other chose cleverness at the cost of clarity. The outcomes weren’t accidents. They were consequences.