What Failure Really Looks Like in Startups

Three deals, five months, all dead inside the same week.

The founder telling me this sells enterprise software with sales cycles long enough to require somewhere between ten and ten thousand meetings. He had been working those three deals since spring.

The first died because his champion took a job somewhere else, and her replacement had a preferred vendor from a previous company. The second died because the buyer got acquired and every discretionary purchase froze. The third died in a budget reshuffle three levels above anyone he had ever spoken to, which he found out about in a two-sentence email.

"None of that had anything to do with me," he said. "Or my product. Or my pitch." He sat back. "So I basically wasted five months."

I asked what he planned to do differently.

"Probably pull back on sales for a while and focus on the product so the value proposition is more obvious."

Terrible answer. And I only knew how terrible because I had watched the exact opposite play out two weekends earlier, on a beach, with my three-year-old.

Four castles

My son wanted a sandcastle. Not a pile. A castle, with a moat, because he had seen one in a book.

I did the digging. He did the patting, and the shell placement, which he took very seriously and which took a long time. Forty minutes, give or take, on a Sunday morning before the beach filled up.

Then a wave came up further than the ones before it and took the whole thing.

He cried. Hard. For about fifteen seconds. Then he picked up the bucket and started again, in the same spot, the same distance from the water, with no new strategy of any kind.

That castle lasted maybe ten minutes. He built a third. Then a fourth.

I thought about moving him twenty feet up the beach where the water could not reach. I did not, and I have thought about why since. Partly because he did not ask me to. He was not treating the wave as a problem to be solved. He was treating it as weather.

A three-year-old has no theory about any of this. He is not being resilient on purpose. He simply has not yet learned the thing adults learn, which is to treat a lost outcome as evidence that the effort was a mistake.

Two things people confuse

You never had control of the outcome. You had control over whether you showed up ready. Those are two different things, and confusing them is the only way this becomes a failure.

My son controlled the digging, the patting, and the shells. He did not control the tide. Nobody does. The tide has a hundred inputs he cannot see and would not care about if he could.

Those deals worked the same way. He could not control a champion changing jobs, a buyer getting acquired, or a budget reshuffle three levels up. No amount of skill saves those deals. What he controlled was whether he showed up prepared, understood the problem, followed up, and ran a clean process. He did all of it. He ran a good process and lost to weather.

The part that is actually the failure

If he pulls back on sales now, he is not protecting himself from anything. He is guaranteeing the next three deals never happen either.

Building the castle twenty feet further from the water sounds like wisdom. It is just a smaller castle, further from where anyone is looking.

That is what failure actually looks like. Rarely the loss itself. Almost always the moment right after it, when you decide the effort was not worth it.

He sat with that for a second, laughed, and said, "So the advice is keep getting my heart broken."

Yes. Keep getting your heart broken. Keep showing up prepared anyway.

My son cries for fifteen seconds and picks the bucket back up. Somewhere between three and forty, most of us trade that for a story about why we stopped building. Get it back. It is the only part any of us controls, and if you do it enough times, the math turns in your favor.