Poor, Black, & Unreachable At 14

By Wayne Winsley

Founder & Executive Director of Brave Enough To Fail Inc.

At age 14, I was living in an orphanage in Cleveland Ohio, had failed eighth grade the previous year, and basically given up on school. I was a poor black kid who, the experts would say,  had given up on my future and was too set in my ways to be motivated to change. I was destined for one of two places, behind bars or dead.

One day, a friend of mine’s dad was disappointed with his report card and began to lecture him. Without intending to, without even realizing that I was in the room, his dad said the words that changed my life forever.

Always strive for excellence no matter what you do. Excellence will overcome, poverty, prejudice, and adversity every time. Just be excellent at whatever you choose to do.”

That simple message motivated me to make the choice that saved my life.

I chose to go back to school and do the absolute best I could. Because of that choice, I didn’t wind up behind bars or dead. Instead I went on to serve my country honorably in the United States Navy which honed my discipline, self-confidence, and work ethic. Those tools gave me the courage to pursue my dream of being a standup comic which in turn led to a two decade career as a radio broadcaster.  The communication skills I developed over that time prepared me to become what I am today, a teacher, and a multi award-winning motivational speaker 

I know first hand that even without intention, a word can change a child’s life.

That is why I’ve dedicated the rest of my life to delivering a message of inspiration and motivation to as many young people as possible through my organization.

Brave Enough to Fail Inc. is a 501 (C) 3 nonprofit that provides motivational programs and scholarships to high schools.

The mission is to raise student achievement by inspiring kids with the courage to achieve their dreams and to help students see their education as a way to get what they want from life. To narrow the education achievement gap by focusing on the student end of the equation with a message of courage, hard work, self-discipline, and determination.

High schools nationwide are requesting this message for their students.

This  summer we have received unsolicited requests for the Brave Enough To Fail program, for the 2017-2018 school year, from schools in over ten states. (See the list below)

Rather than saying, “No we can’t help you.” We are taking a leap of faith and committing to raising the funds needed to deliver the message to the thousands of students at these schools that,  Their Dreams Are Important And Achievable!

There are other young people out there who just like I was, are one positive message away from overcoming the poverty, prejudice, and adversity that is standing between them and achieving a better life for themselves.

That is why I am asking the questions,

Is there at least one corporation in this great nation that would like their brand to be known for motivating and inspiring youth across America?

If you are that corporation, please contact us at info@BraveEnoughToFail.org

Are there fellow citizens willing to sow seeds of success into the youth of our communities? 

If you are that citizen, please make a donation here. 

Partial list of schools that have reached out and requested Brave Enough To Fail

Crest High School, Shelby NC.

Cathedral High School, New York NY.

Urban Assembly of Media Studies, New York NY.  

 Whitestone High School, Delta Junction Alaska

Sultan Sr High, Sultan Washington

Cicely Tyson High, East Orange New Jersey

St. Timothy’s School, Raleigh NC

Briar Woods High School, Ashburn VA.

Ferndale High, Johnstown PA.

Scottsburg High, Scottsburg IN.

Little Rock Arkansas School District

Martin County School District, Stuart Florida

Integrated Arts Academy, Chaska MN.

Frederick Banting School, Ottawa Ontario


Wayne Winsley





Brave Enough To Fail, a Connecticut based, 501 (C) 3 nonprofit that provides motivational programs and scholarships to high schools, is holding an open casting call for corporate partners to sponsor their plan to inspire student achievement nationwide.

The assembly-style presentations deliver a powerful message designed to inspire students to achieve great things. The scholarships are designated specifically for each school to give the motivated students an achievable goal to work toward.

Wayne Winsley, founder and executive director of the organization says,

“Over the summer, we have received requests for this program from schools in at least nine states, including Florida, Illinois, Indiana, New York, New Jersey, North Carolina Pennsylvania, Virginia, and Washington, all for the upcoming school year.

Rather than saying no, we don’t have the resources to meet this demand, we are instead asking the question,

Is there at least one company in America that would like to have their brand associated with planting seeds of success in the minds of thousands of students across the nation?

We believe the answer is yes, that is why we’ve created this opportunity for that right company or brand to connect and work with us and inspire kids to achieve their dreams.”

Interested parties may contact Wayne Winsley, wayne@BraveEnoughToFail.org