Available on Spotify, Apple Podcasts, and wherever you get your podcasts.
We all love to win. Winning feels good, it’s validating, and it makes us think we’ve figured something out.
And we usually learn the most when things don’t go our way.
In this episode of Five with Fry, I talk about the hard—but freeing—lesson that failure delivers your biggest breakthroughs. As someone who’s wildly competitive, losing doesn’t sit well with me. I hate it. But over time, I’ve realized that the moments that sting the most are also the ones that push me to think differently.
The Pitch Competition That Changed Everything
Not long ago, I entered a tech pitch competition. I was confident, prepared, and ready to win. When I didn’t, I was upset. Angry, even.
But something shifted on the drive home. While talking to my mentor Ty, ideas started pouring out—better ideas than I’d ever had before. I started seeing my company in a new way. The solutions that came to me wouldn’t have surfaced if I’d walked away with first place.
That loss cracked something open. It made me rethink my assumptions, sharpen my approach, and imagine what was possible if I stopped trying to get it “right” the first time.
Why Losing Works
When you win, you rarely stop to question what worked or what didn’t. But when you lose, you start analyzing every detail. You dig deeper. You get creative.
That’s where innovation happens.
Failure forces reflection, and reflection sparks growth.
I see so many people throw in the towel after a rejection. They believe that if their first effort didn’t succeed, it’s proof that they should quit. But the truth is, the first version of anything—your pitch, your product, your leadership—isn’t supposed to be perfect. It’s supposed to get you started.
The Power of Iteration
If you want to get to great, you have to keep working the idea. Keep testing it, reshaping it, and polishing it until it shines. Just like a diamond, brilliance only shows up after time, pressure, and a few painful cuts.
That process isn’t easy, but it’s what separates good from exceptional. Each “no” you hear is data. Each setback is a step toward the next version of your best work.
The Real Lesson
The next time you fail—or get told no—pause before you give up. That rejection might be the thing that forces your best thinking forward.
Failure isn’t the end of the story. It’s where the next chapter begins.
🎧 Listen to Five with Fry: Why Failure Delivers Your Greatest Breakthroughs wherever you get your podcasts.
