I worked at 2 startups. Both failed.

The first had been around for about 4 years when I joined and had products that made money. They were trying to get acquired. They had partnered with 2 companies making products specifically for them. One of them offered to buy the company for $30 million but the founders thought their company was worth $300 million. They said no and then money started to run out and people started leaving. In the end the assets were sold for $2 million.

The second startup was created by former coworkers and I joined after it had existed for 4 months. We worked like crazy for the first year and got our prototype out. We had a lot of interest but it took me a while to realize that the 3 founders already had net worths from $5 million to billionaire level. When I heard about offers in the $30 million range they just weren't interested in selling for so little. I left after 3 years and the company floundered another 2 years until they shut it down as people left.

These are perfect examples of how misaligned expectations can quietly sink a company. In both cases, the teams actually had something: revenue, interest, real offers. But when the founders anchor on a fantasy outcome, they stop making grounded decisions.

You can survive almost anything in a startup except delusion about what the company is worth. Turning down a realistic exit, or holding out for a number that only exists in your head, creates a slow death spiral: morale drops, talent leaves, and eventually the market decides for you.

Really appreciate you sharing these — they highlight a pattern that happens far more often than people think.