233: when nothing works

Failure Is Not a Phase—It’s the Game

We love those underdog stories. Babe Ruth struck out 1,330 times. Colonel Sanders got rejected 1,009 times. Michael Jordan didn’t make the high school team.

But what people miss is that they kept failing. Ruth didn’t suddenly stop striking out. Jordan didn’t suddenly win every game. And neither do we.

I used to think, “If I just push through this one dip, I’ll make it.” But the truth is, there is no “making it.” There’s only continuing, and that continuation is full of failure.

Learn from the Wolves

In my book Killing Comfort, I share the story of the wolf—a powerful, respected predator. Yet wolves fail 86% of their hunts. Think about that. They’re out there every day doing what they were born to do… and most of the time, they fail.

But they don’t stop. They can’t. Survival depends on trying again. And that’s us.

You run an ad campaign—it flops. Cool, run another one. Leadership conversation fell flat? Try again. The process is the work.

Failure Is Feedback, Not Final

Entrepreneurship has been the most intense personal development journey of my life. Because you don’t just try something and succeed—you try, fail, learn, and try again.

If you’re not okay with that process, this isn’t going to work. But if you can find comfort in the discomfort, you’re getting closer to mastery.

Campaigns fail. Pitches bomb. Emails flop. And that’s fine. Failure is data. Use it. Iterate. Improve.

Don’t Buy the "One Strategy" Lie

I’ve never had one campaign or strategy that made everything click. Ever.

And if someone’s selling you that—run. It’s not real. It’s marketing. What’s real is stacking small lessons from repeated failure and improvement until something works.

Most of what I do fails. And when it doesn’t? That’s the 14% success rate keeping the business alive.

Thick Skin Is the Strategy

If you’re feeling overwhelmed, anxious, and crushed by the pressure… you’re not alone.

But you do have a choice. You can become the diamond. You can let the pressure make you stronger, sharper, more adaptable. But that only happens if you embrace failure and grow from it.

At every revenue level I’ve hit—$1K/month to hundreds of thousands—there have been problems. Always. That doesn’t stop. But my response to those problems? That’s what changed.

Time-Stamped Show Notes

• 00:30 – Why cliché failure stories don’t tell the whole truth

• 01:20 – The wolf metaphor: Failing 86% of the time and still thriving

• 02:10 – You don’t “make it”; you just keep going

• 03:00 – Why failure is the daily norm in entrepreneurship

• 04:00 – Tactical mindset shift: One campaign fails? Run another

• 04:55 – How to use failure as feedback

• 05:35 – There is no magic strategy—just repetition and refinement

• 06:30 – Handling pressure: you’re not a diamond, but you have a choice

• 07:15 – Optimizing for discomfort = real success

• 08:00 – Final message: Embrace failure, or it’ll crush you