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PRESS & MEDIA

FEATURED STORIED, INTERVIEWS, PODCASTS AND MORE

ARTS SOCIETY & ME | SEPTEMBER 14, 2026

Brave Enough To Fail Adds BOSS Academy To Curriculum At Another School

Brave Enough To Fail Adds BOSS Academy To Curriculum At Another School

Covers the 2024 expansion of BOSS Academy to Schaghticoke Middle School and quotes Wayne as CEO and founder.

IHEART | NOVEMBER 23, 2025

Community Access Interview with Founder & CEO of Brave Enough to Fail

Community Access Interview with Founder & CEO of Brave Enough to Fail

Alison Demurz interviews Wayne as founder and CEO, covering his background, the organization's origin, BOSS Academy, and its mission. Includes an auto-generated transcript.

NEWS 12 CONNECTICUT | JUNE 29, 2025

Bridgeport nonprofit teaches kids how to succeed 'in school and beyond'

Bridgeport nonprofit teaches kids how to succeed 'in school and beyond'

Independent television coverage including an interview with Wayne and a student participant. Discusses founding BETF and the skills taught through the program.

P-TECH NORWALK | MARCH 19, 2024

BOSS Academy Students Honored at Brave Enough to Fail Gala

BOSS Academy Students Honored at Brave Enough to Fail Gala

Identifies Wayne as founder and CEO, explains BOSS Academy, documents its incorporation into P-TECH's curriculum, and describes students being trained as facilitators and mentors.

WILTON PATCH | MARCH 11, 2024

Boucher Awarded 'Person Of Courage' Honors At BOSS Academy Gala

Boucher Awarded 'Person Of Courage' Honors At BOSS Academy Gala

Covers the BETF gala, BOSS Academy, Wayne's organization, student participation, and the program's expansion at P-TECH Norwalk. Published March 11, 2024.

KIWANIS CLUB OF GREATER DANBURY | JUNE 13, 2023

Wayne Winsley speaking on Brave Enough To Fail initiative and scholarship

Wayne Winsley speaking on Brave Enough To Fail initiative and scholarship

Documents Wayne speaking about his Brave Enough To Fail initiative and presenting a BETF scholarship.

CT INSIDER | SEPTEMBER 26, 2022

Union Savings Bank Foundation grant supporting BOSS Academy

Union Savings Bank Foundation grant supporting BOSS Academy

Regional community-news report listing Brave Enough To Fail as a recipient of a $15,000 Union Savings Bank Foundation grant supporting BOSS Academy.

NEW HAVEN REGISTER | FEBRUARY 27, 2021

"Strive for excellence": New Milford nonprofit motivates students despite pandemic uncertainty

"Strive for excellence": New Milford nonprofit motivates students despite pandemic uncertainty

The New Haven Register's version covers Wayne's personal story, how Brave Enough To Fail and BOSS Academy came together, student voices from the program, and what drives him to keep the work going despite pandemic disruptions.

CT INSIDER | FEBRUARY 27, 2021

"Strive for excellence": New Milford nonprofit motivates students despite pandemic uncertainty

"Strive for excellence": New Milford nonprofit motivates students despite pandemic uncertainty

CT Insider's version goes deep on Wayne's life story, his educational mission, and the work of BETF.

HOUSTON CHRONICLE | FEBRUARY 27, 2021

"Strive for excellence": New Milford nonprofit motivates students despite pandemic uncertainty

"Strive for excellence": New Milford nonprofit motivates students despite pandemic uncertainty

The New Haven Register's version covers Wayne's personal story, how Brave Enough To Fail and BOSS Academy came together, and the students the program has reached. It also gets into what drives him to keep the work going, even as schools dealt with pandemic disruptions.

CONNECTICUT POST | FEBRUARY 21, 2021

"Strive for excellence": New Milford nonprofit motivates students despite pandemic uncertainty

"Strive for excellence": New Milford nonprofit motivates students despite pandemic uncertainty

Substantial profile of Wayne, his personal story, Brave Enough To Fail, BOSS Academy, students, and his motivation for the work. Arguably the single most important independent article for his Wikipedia/speaker credentials.

BUSINESS INNOVATORS RADIO NETWORK | JAN 16, 2021

Interview with Wayne Winsley, Fouder and CEO of Brave Enough to Fail

Interview with Wayne Winsley, Fouder and CEO of Brave Enough to Fail

Dedicated interview featuring Wayne's personal story - growing up with his great-grandmother, entering the child-welfare system, leaving school, serving in the Navy, his broadcasting career, and ultimately creating Brave Enough To Fail.

WESTON PATCH | OCTOBER 21, 2015

Motivational Speaker Does 5,000 Pushups in One Month to Inspire Redding Kids

Motivational Speaker Does 5,000 Pushups in One Month to Inspire Redding Kids

Fun but useful independent coverage documenting Wayne's motivational work and the Brave Enough To Fail initiative.

NEW HAVEN REGISTER | DECEMBER 7, 2012

Wayne Winsley has a strong message for New Haven students

Wayne Winsley has a strong message for New Haven students

Documents Wayne announcing a 50-high-school motivational speaking tour and his "Brave Enough to Fail" presentation, showing the message predates the current scale of BETF.

NEW HAVEN REGISTER | MAY 23, 2012

DON PESCI: Wayne Winsley's mission to students

DON PESCI: Wayne Winsley's mission to students

Predates much of the later BETF publicity; documents Wayne's motivational speaking work with students, including his Achievement and Motivation presentation and his work at Harding High School and other Connecticut schools.

NEW HAVEN REGISTER | DECEMBER 25, 2011

Election 2012 candidate coverage

Election 2012 candidate coverage

The Register's election coverage identifying Wayne as the Republican candidate for Connecticut's 3rd District.

NEW HAVEN REGISTER | OCTOBER 29, 2011

Winsley states his case in the 3rd District race

Winsley states his case in the 3rd District race

Older political/public-life coverage of Wayne, published October 29, 2011. Not a BETF story, but useful broader biography material.

NEW HAVEN REGISTER | OCTOBER 17, 2011

Republican Winsley facing DeLauro for 3rd District seat

Republican Winsley facing DeLauro for 3rd District seat

Older political coverage from October 17, 2011, covering Wayne's Congressional race against Rosa DeLauro.

NEW HAVEN REGISTER | OCTOBER 3, 2012

Wayne Winsley pushes for debates against Rosa DeLauro in 3rd District race (video)

Wayne Winsley pushes for debates against Rosa DeLauro in 3rd District race (video)

This New Haven Register piece is especially notable for being explicitly marked as video coverage, capturing Wayne pushing for debates against Rosa DeLauro in the 3rd District race, from October 3, 2012.
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