
Wayne Winsley
Inspiring
The Future Of America

Motivational & Inspirational Keynote Speaker
Motivational keynote speaker, Navy veteran, and founder of Brave Enough To Fail. Inspiring students and adults to act on their dreams with grit, integrity, and a plan.
About Wayne
Raised in Cleveland, Wayne Winsley turned hardship into a platform for change. A U.S. Navy veteran who served two tours aboard the aircraft carrier USS Enterprise as a jet engine mechanic, military police officer, and special weapons handler.
He built a career as a broadcast professional, award-winning keynote speaker, and educator.
For over ten years he was host of his own Talk-Show, The Wayne Winsley Program.
Wayne is a veteran teacher with over ten years of classroom experience.
He is also an Author. His first novel, an FBI thriller entitled, The Leprechaun Deception, was published in 2005.
As a public speaker, Wayne has won several awards including:
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Monster World-wide’s Speaker of the Year
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Toastmasters Area Speech Champion Twice
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Toastmasters Regional Speech Champion
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As the founder of Brave Enough To Fail, Wayne dedicates his work to giving high school students free motivational presentations, scholarships, and resources to raise achievement and cultivate leaders, creators, and achievers.​​​​​
Brave Enough To Fail is a student-focused nonprofit that provides motivational programs, educational resources and financial aid to help students succeed in school and beyond.
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Since 2015 Brave Enough To Fail has impacted over 40,000 students
and awarded over $125,000 in scholarships.



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Wayne Winsley was that kid most likely to fall through the cracks.
As a kid in Cleveland, Ohio, Wayne was raised by his great-grandmother. However, when she became too old to care for him, Wayne found himself in the social welfare system. He spent time in an orphanage and in Boys Town. He stumbled through school, failed the eighth grade and basically dropped out of school. Statistically, he was quite likely to end up in one of two places, prison or the cemetery .
Thanks to an overheard message, and through a combination of hard work, determination, and being brave enough to fail, Wayne graduated high school, served his country honorably in the U. S. Navy. In 2012, he ran for U.S. Congress in Connecticut.
Just a few satisfied clients










