The Strength in Losing: Embracing Failure as a Path to Growth

The Power of Being a Great Loser: Why I Embrace Failure

In the world of business and personal development, failure often carries a heavy stigma. Many people fear it, avoid it, or try to hide it at all costs. But what if failure wasn’t something to be ashamed of? What if, instead, it was one of your greatest assets?

I consider myself the greatest loser you’ll ever meet—not in the sense of financial missteps or career blunders, but in my relationship with losing itself. Over time, I’ve come to view losing as one of my greatest strengths. This mindset has completely transformed how I approach both life and business.

Why I Call Myself the Greatest Loser

There are two simple reasons why I proudly claim this title:

1. I lose all the time – Because of this, I’ve gotten really good at handling setbacks.
2. Every loss is a win – Each failure teaches me something valuable that contributes to long-term success.

This shift in perspective has been instrumental in shaping my career, especially in the high-stakes worlds of sports and entertainment. Whether negotiating contracts or making investment decisions, not everything works out as planned. But those who fear losing often miss the biggest opportunities. They play it safe, stick to familiar territory, and ultimately limit their potential.

Learning to Lose Effectively

Losing effectively isn’t about celebrating failure—it’s about extracting value from it. Every setback is an opportunity to grow, refine strategies, and improve decision-making.

For example, early in my career, I lost a major client because I focused too much on closing the deal and not enough on building a genuine relationship. That painful loss taught me a critical lesson: sustainable success comes from meaningful connections, not just transactions.

The most successful people I know aren’t those who avoid failure—they’re the ones who lose fast, learn quickly, and adjust immediately. This requires humility and the ability to admit when you're wrong without letting ego cloud your judgment.

Reframing Failure as Research

I now view every loss as research—valuable data that helps me fine-tune my approach. This mental shift transforms failure from something to fear into something to leverage.

When you embrace this mindset, you’ll notice three immediate benefits:

• You take more calculated risks because you’re not paralyzed by fear of failure.
• You recover faster from setbacks since you focus on the lessons learned rather than dwelling on the loss.
• You develop greater resilience as losing becomes part of your growth process.

This approach has served me well throughout my career—from my time as CEO at Leigh Steinberg Sports & Entertainment to my current role as Chairman of the Napoleon Hill Institute.

Becoming a Great Loser

So how do you become a great loser? Start by changing your relationship with failure. When something doesn’t work out, resist the urge to hide, deny, or blame others. Instead, ask yourself: “What can I learn from this?”

Document your losses and the insights they provide. Over time, patterns will emerge that help you make better decisions. You’ll also build confidence in your ability to handle setbacks, which makes you more willing to pursue ambitious goals.

Remember: losing isn’t the opposite of winning—it’s part of the winning process. Every significant achievement in history came after numerous failures and adjustments.

Final Thoughts

I challenge you to become a great loser. Embrace the process, extract the lessons, and watch how it transforms your results. In the end, those who learn to lose effectively ultimately win more than those who try to avoid losing altogether.

Failure isn’t a dead end—it’s a detour that leads to growth, innovation, and long-term success. So the next time you fall short, don’t despair. Reflect, adapt, and move forward with even greater clarity and purpose.