About Wayne Winsley
Wayne Winsley is a dynamic, award winning motivational speaker, educator, U.S. Navy Veteran and the visionary founder of Brave Enough To Fail, Inc.—a nonprofit that is cultivating a new generation of leaders, creators, achievers by providing motivational programs, educational tools and scholarships to help students succeed in school and beyond. Drawing on a diverse career spanning broadcasting, public speaking, and education, Wayne delivers compelling messages of resilience, personal growth, and the power of perseverance to audiences nationwide.
Before launching Brave Enough To Fail, Wayne spent over two decades in broadcasting, captivating audiences as a news anchor, talk show host, and voice-over artist. His powerful storytelling and commanding presence earned him accolades and a loyal following. Today, he channels that same energy into classrooms, auditoriums, and boardrooms, inspiring students and stakeholders alike with his message: “Success is not about luck—it’s about courage, commitment, and action.”
Under his leadership, Brave Enough To Fail has reached thousands of students in classrooms and communities across the Northeast, delivering transformative programs that equip young leaders with the tools, inspiration, and resources to realize their highest potential.
His personal journey includes being raised by his great-grandmother in inner city Cleveland, spending time in the social welfare system (including an orphanage and Boys Town), failing the eighth grade, and nearly dropping out of school before an overheard message inspired him to graduate high school and join the Navy.
Known for his passionate delivery, humor, and compelling personal story, Winsley is a sought- after speaker for schools, conferences, businesses, podcasts and other media platforms that want to inspire audiences with a message of resilience, responsibility, and real-world success.
His expertise in building resilient mindsets and fostering community engagement makes him a valuable contributor to conversations about youth development, leadership, and lasting social impact.
Wayne Winsley’s message is simple but powerful: Every young person matters. Every dream matters. And every dream deserves a chance.
Professional Background Highlights
Wayne Winsley's diverse career provides a rich source of conversation for any platform:
Non-Profit Leadership: Co-Founder and CEO of Brave Enough To Fail, a mission-driven organization focused on student empowerment.
Motivational Speaking: An award-winning public speaker, including recognition as Monster World-wide’s Speaker of the Year and a two-time Toastmasters Area Speech Champion.
Radio Veteran: Host of his own issues-oriented talk show, The Wayne Winsley Program (known to listeners as "The Conservative Capitalist"), and a news anchor in the Fairfield County and Norwalk/Stamford markets.
Educator: Veteran teacher with over ten years of classroom experience teaching History and Current Events to middle and high school students.
Wayne Winsley's story is one of transformation, showing audiences that no matter the starting point, hard work and courage can lead to remarkable achievement.
Organizations & Events Ideal for Wayne Winsley as a Keynote Speaker
