I'm obsessed with companies that fail or just can't seem to get their shit together. I know that sounds like a weird thing to say, but for some reason, I really love the stories that come out of disaster organizations.

Companies that fail are usually centered around a few core reasons.

  1. They have disaster leadership, aka the CEO is a mess, for many reasons
  2. Their product never really took off, but somehow they smoke and mirrored their way to early success before failing
  3. We learn their culture was full of all sorts of unethical, inappropriate behavior-related types of things

The thing is, these organizations don't have to fail, but they do because they can't get out of their own way.

There's so much to learn, both if you work at an organization like this currently, and or if you have worked at an organization like this in the past.

The most fascinating part is that most of these companies had every resource they needed to survive. They had funding, talent, market opportunity, and in many cases, a product people actually wanted. What they didn't have was the self-awareness to see the fire spreading from the inside. That's not a business problem. That's a people problem. And people problems are always more expensive than anyone budgets for.

Take leadership. When the person at the top is the problem, everything below them gets infected. Bad leaders rarely arrive wearing a sign. They show up confident, charismatic, and full of big promises. They interview well. They raise money well. They give speeches that make people genuinely believe. But eventually the cracks show, and the people closest to them start making a choice: do I say something, or do I protect my job? In disaster organizations, the answer is almost always the same. People go quiet. And the silence is what kills the company.

The smoke and mirror companies are a different kind of fascinating. These are the ones where the product never really worked, but the story was so good that nobody stopped to ask hard questions. Investors didn't ask. The media didn't ask. Early customers convinced themselves they were seeing something real because everyone else seemed to believe it too. There's a name for that. It's called social proof turned against itself, and it is one of the most dangerous forces in business. When the emperor has no clothes and nobody wants to be the one to say it, the parade just keeps going until it doesn't.

Then there's the culture piece, which is always the part people want to talk about the most because it's usually the most shocking. The behavior that comes out of these organizations in post-mortems is almost never surprising to the people who were inside them. They knew. They watched it happen in real time. The harassment, the favoritism, the cover-ups, the meetings after the meetings. The reason it looks like a bombshell from the outside is because the inside stayed quiet for so long. Culture problems don't appear overnight. They get built, decision by decision, until they're just the way things are done around here.

Here's what I want you to take from all of this if you are currently sitting inside a company that feels like it might be one of these stories. Your instincts are probably right. The thing you keep dismissing as just a rough patch or growing pains or leadership being leadership is worth paying attention to. Smart people talk themselves out of their own gut feelings constantly because it feels easier to stay than to deal with the uncertainty of leaving. But staying inside a sinking organization doesn't make you loyal. It makes you late.

If you've already lived through one of these companies, you have something most professionals don't. You have a real education in what bad actually looks like up close, and that is genuinely valuable. The people who come out of disaster organizations and take the time to understand what went wrong, rather than just trying to forget it, tend to become sharper leaders, better judges of culture, and harder to fool in the future. The experience only becomes a liability if you let it make you cynical instead of clear-eyed.

The real lesson these companies keep teaching, over and over, is that none of it had to go the way it did. At almost every step, someone had a chance to make a different call. Someone could have told the truth earlier. Someone could have pushed back harder. Someone could have walked out the door before the whole thing came down. The failure was never inevitable. It was a series of choices made by real people who either didn't know better or knew exactly what they were doing and did it anyway. That's what makes these stories worth studying. Not for the drama, but for the decisions.