Episode #318

Chasing Failure: Real Life Lessons from One Man’s Shot at the NBA with Ryan Leak

Key Takeaways

Chase failure intentionally: stop assuming rejection, take small risks, and go for opportunities even if you feel underqualified.

Build momentum with daily wins: break big goals into bite-size steps, count every small W (even a no-response or a rejection) as progress.

Beat perfectionism and procrastination by starting with what you have, accepting imperfection, and being intentional with your limited time.

Top Quotes

Stare fear in the face, and go, you will not steer my life.

You just need a W.

It's never going to be perfect, ever.

Episode Summary

What would you do if you knew you couldn’t fail? How would it change your life?

Ryan Leak is an author, speaker, executive coach, and filmmaker. He is widely known as the groom who pulled off The Surprise Wedding where he proposed to his girlfriend and married her on the same day.

The number one question he still gets is, “What if she said no?”

It was a risk he was willing to take.

The video going viral led him to think about what others would do if they weren’t afraid of hearing “no” or of being met with failure.

Ryan realized that many people never pursue their hopes and dreams because they pre-calculate their own failure. They quit before they ever even try.

So, he asked himself: What would he want to do if he knew he could not fail? The answer was easy— he’d be in the NBA— and since the only way to know if that dream could be a reality was to try, that is exactly what he did.

In this episode, Ryan joins us to amplify why our show is called Success Through Failure. Listen in as we talk about procrastination, “perfection pressure,” how chasing failure will take you further than chasing success, and of course, his stories of success BECAUSE of failure. Tune in now!

Guest Bio & Links

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