AW-923964925

About us

Brave Enough To Fail empowers middle and high school students to build confidence, resilience, and direction — giving them the tools to set goals, follow through, and shape their own future.

Who we are

Brave Enough To Fail is a nonprofit that not only provides motivational speaking services in the field of dream achievement, we are dedicated to helping middle and high school students step into who they can become.

We work with schools and youth programs to build confidence, purpose, resilience, and the practical success skills teens need to move toward college, career, or trades with intention.

Our BOSS Academy curriculum, combined with scholarship support, gives students structure, clarity, and the belief that their effort matters — especially in communities where opportunities often feel limited. We exist to make sure young people don’t just hope for a better future — they’re equipped to create it.
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Our purpose

Our purpose is to make sure every student — regardless of background — develops the courage, clarity, and skills to take ownership of their future. We empower teens to set meaningful goals, stay resilient through setbacks, and turn effort into real progress, so they don’t just dream about what’s possible… they learn how to make it happen.

Brave Enough To Fail is trusted across schools, districts, and youth programs nationwide

We partner with educators to build student ownership, strengthen resilience, and help teens connect daily effort to real future outcomes — without adding more burden to teachers.

Students served

BOSS Academy participants

in scholarships awarded to date

Meet our team

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Wayne Winsley
CEO and Co Founder

Wayne Winsley is the co-founder and CEO of Brave Enough To Fail and the creator of the BOSS Academy program. A U.S. Navy veteran, former award-winning radio broadcaster, and longtime history teacher, Wayne has dedicated his life to inspiring young people with the courage, strategy, and grit to pursue their dreams.  

Through his leadership, BOSS Academy now equips students with the mindset and skills to set big goals, step outside their comfort zones, and succeed in school and beyond.
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April Dawn Winsley
COO and Co Founder

April Dawn Winsley is the co-founder and Chief Operations Officer of Brave Enough To Fail, where she helps oversee the systems, structure, and support that keep BOSS Academy running with excellence.  An author, former radio personality, producer, and co-host of The Wayne Winsley Program, April brings a unique blend of creativity, communication, and operational savvy to the team.

Her love of photography inspired her book, Where Are You Going? Questions for Your Journey in Life, the official textbook of Brave Enough To Fail’s BOSS Academy, which invites students to pause, reflect, and chart their own path forward through powerful images and guiding questions. 
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 Judy Dumas
M.Ed

 Judy Dumas, M.Ed, is an educational leader and Assistant Principal at Faith Preparatory School, where she is dedicated to equipping students academically, emotionally, and spiritually.  With a doctorate in Educational Leadership and a background in secondary education, she brings deep expertise in curriculum, instruction, and student development to her role on the BOSS Academy team.  Mrs. Dumas is passionate about creating supportive, growth-focused school environments that help young people discover their potential and pursue their God-given purpose.
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Dr. Danielle Rivard,
EdD

Dr. Danielle Rivard, EdD, is an educational leader with a passion for helping students grow both academically and personally.  She holds a doctorate in Educational Leadership and a BA in Secondary Education, bringing a strong foundation in teaching, curriculum, and school culture to the BOSS Academy team.  Dr. Rivard is dedicated to empowering young people to discover their strengths, set meaningful goals, and pursue their future with confidence and purpose