When I lost everything in 2009, my first instinct was to interpret it as a verdict. A judgment on my abilities. Proof that I wasn't cut out for this.
That interpretation was wrong. And it nearly destroyed me.
The Story We Tell Ourselves
Most founders have a complicated relationship with failure. We know, intellectually, that failure is part of entrepreneurship. We've read the stories. We know the statistics.
But when it happens to us? That's different. When our company is struggling, when we make a bad hire, when a deal falls through — we don't think "interesting data point." We think "I failed."
That's the problem. We're treating failure as identity, not information.
What Failure Actually Is
Failure is feedback. Nothing more, nothing less.
When something doesn't work, you've learned something. You've learned that this particular approach, in this particular context, with these particular resources, didn't produce the result you wanted.
That's useful information. That's data you can act on.
But here's the key: You have to actually extract the lesson. Failure only becomes valuable when you examine it honestly:
- What actually went wrong?
- What did I control? What didn't I control?
- What would I do differently next time?
- What assumptions was I making that turned out to be wrong?
The Danger of Avoiding This Work
Some founders respond to failure by pretending it didn't happen. They rationalize. They blame external factors. They move on without examining what went wrong.
This is comfortable in the short term. It's disastrous in the long term.
If you don't extract the lessons, you're likely to repeat the mistakes. And the next failure will feel even more like destiny — because it keeps happening.
The Danger of Over-Internalizing
Other founders go the opposite direction. Every setback becomes evidence of their fundamental inadequacy. They take failure personally, deeply, painfully.
This is equally dangerous. It leads to decision paralysis, risk aversion, and eventually burnout. If every failure proves you're not good enough, eventually you stop trying.
The Middle Path
The healthiest relationship with failure is somewhere in between:
Take responsibility without taking it personally. Yes, you made decisions that led to this outcome. That doesn't mean you're a bad person or a bad founder. It means you're human, and humans make mistakes.
Learn without spiraling. Extract the lesson. Make the adjustment. Then move forward. Don't spend weeks in self-flagellation.
Share the lessons. Talking about failure — what went wrong, what you learned — helps other founders. It normalizes the experience. And articulating the lesson often clarifies it.
My Experience
After losing $15 million and ending up $5 million in debt, I had years to extract lessons. Here's what I learned:
I had built businesses that required my constant presence. That wasn't sustainable.
I had ignored warning signs because I was too busy putting out fires. The fires were symptoms, not the disease.
I had conflated working hard with working smart. They're not the same thing.
I had no support system. No one to call when things got hard. No one to give me perspective.
Those lessons shaped everything I do now. They're why Fail Coach exists.
But I only got those lessons because I was willing to look honestly at what went wrong. If I had blamed the economy, blamed my partners, blamed bad luck — I would have learned nothing. And I probably would have made the same mistakes again.
The Bottom Line
Failure is information. It's data about what doesn't work in your specific context.
Your job isn't to avoid failure — that's impossible. Your job is to fail in ways you can learn from, extract the lessons efficiently, and apply them going forward.
That's not easy. It requires honesty and self-reflection. But it's the only path to building something that lasts.