Talk:Wayne Winsley

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Wayne Winsley Wayne Winsley (born August 13, 1963) is an American nonprofit executive, motivational speaker, author, and former radio broadcaster. He is the founder and chief executive officer of Brave Enough to Fail, Inc., a Connecticut-based youth motivational and mentoring nonprofit he established in 2015. [1] Before founding the organization, Winsley spent roughly two decades in Connecticut radio as a news anchor, talk-show host, and disc jockey, [2][3] and in 2012 he was the Republican nominee for the U.S. House of Representatives in Connecticut's 3rd congressional district, losing to incumbent Democrat Rosa DeLauro. [4]

Early Life Winsley was born in Cleveland, Ohio, on August 13, 1963. [4][5] According to his own published accounts, he was raised for a time by his great-grandmother; when she was no longer able to care for him, he spent time in the child- welfare system, including a placement at Boys Town, and later moved to Stamford, Connecticut, where he lived with his mother and siblings. [5][6] He has said he struggled academically as a child and did not complete the eighth grade on schedule, but went on to finish high school. [5][7]

Military Service Winsley served in the United States Navy from 1982 through 1986, attaining the rank of petty officer and made two Western Pacific deployments aboard the aircraft carrier USS Enterprise as part of Viking Squadron 21. [4][1][6]

Radio Broadcasting Winsley worked for about 20 years in Connecticut radio as a news anchor, talk-show host, and disc jockey. [2][3] He was a morning news anchor for AM radio stations serving the Bridgeport and Norwalk markets before being laid off in the late 2000s, [2] and for about a decade he hosted a talk show on WINE 940 AM in Danbury, where he used the on-air identity "Connecticut's Conservative Capitalist. "[2]

Other work and community roles Outside of broadcasting, Winsley has worked as a private investigator and served for a year, beginning in 2003, as president of the Danbury chapter of the NAACP. [4][2][8] He has also worked as a middle and high school history and current-events teacher.[6][9]

Writing In 2005, Winsley published The Leprechaun Deception, a crime-thriller novel, which he followed with two further novels, Duplicity and Delusion. [3]

Political career In 2010, Winsley served as communications director and spokesman for gubernatorial campaigns in Connecticut, working for Republican candidates Tom Foley and Mark Boughton. [4][2] In late 2011, Winsley — then living in New Milford — relocated to Naugatuck, within Connecticut's 3rd congressional district, and announced that he would seek the Republican nomination to challenge longtime Democratic incumbent Rosa DeLauro. [2] He ran unopposed for the Republican nomination and campaigned on a platform emphasizing tax relief, reduced federal spending, immigration enforcement, and veterans' issues. [4] During the campaign, Winsley said his own past reliance on social-safety-net programs, including during a period out of work while being treated for prostate cancer, shaped a more cautious view than some in his party toward cutting those programs. [10] He also publicly pressed DeLauro's campaign for multiple debates, saying his requests had gone largely unanswered; DeLauro's campaign said she would instead appear at candidate forums. [11][12] In the November 6, 2012, general election, DeLauro was reelected, defeating Winsley by a margin of about 74.7% to 25.3% of the vote. [4]

Brave Enough To Fail In 2015, Winsley founded Brave Enough to Fail, Inc., a nonprofit organization based in New Milford, Connecticut, that provides motivational programming, educational resources, and scholarships for students for middle and high school students, including a course known as BOSS Academy. [1] His wife, April Winsley, is the organization's co-founder and chief operating officer. [9] The organization says its programs have reached tens of thousands of students and distributed scholarship funds to students in Connecticut, and it has partnered with schools and community organizations, including LifeBridge Community Services in Bridgeport and the College of Westchester, to deliver programming and support students' transitions to college. [1][13][1

BOSS Academy The organization's principal program is BOSS Academy, a 12-session youth-development course focused on goal setting, time management, communication, resilience, and related skills. The program has been delivered through schools and youth-serving organizations in Connecticut. P-TECH Norwalk reported that BOSS Academy was incorporated into its curriculum and that students were trained as facilitators and mentors. [15]

References 1. Napolitano, Kayla. Connecticut, June 29, 2025. "Brave Enough To Fail Bridgeport nonprofit teaches kids how to succeed in school and beyond. " News 12 2. "Naugatuck man to run for Congress. " Citizen's News, December 2011. 3. Kobak, Steve. "Author in search of real life character for next novel. " The Hour, July 28, 2008, p. A3. 4. "Wayne Winsley. " Ballotpedia, accessed 2026 (data sourced to the Connecticut Secretary of the State's official 2012 general election results). 5. Wayne Winsley — official website, "About, " accessed 2026. (Self-published source, used only for uncontroversial biographical claims per Wikipedia's WP:ABOUTSELF guideline.) 6. "Interview with Wayne Winsley, Founder and CEO of Brave Enough To Fail. " Business Innovators Radio, January 16, 2021. 7. Same as note 5. 8. "Obsitnik wins GOP nod in 4th House District. " Connecticut Post, May 2012. 9. "Our Team. " Brave Enough to Fail, accessed 2026. (Self-published organizational source, used only for uncontroversial factual claims about its own founders per WP:ABOUTSELF.) 10. "DeLauro's Challenger Seeks 'Reasonable' Cuts. " New Haven Independent, 2011. 11. "Winsley: What About Me?" New Haven Independent, 2012. 12. Salerno, Laurie Rich. October 9, 2012. "Winsley: Only a debate will do; DeLauro's staff says forums are good enough. " Record-Journal, 13. "The College of Westchester and Brave Enough to Fail Join Forces. " The College of Westchester, 2025. 14. Wayne Winsley — official website, homepage, accessed 2026.

[15] P-TECH Norwalk, “BOSS Academy Students Honored at Brave Enough to Fail Gala” (Mar. 19, 2024). https://ptech.norwalkps.org/about/p-tech-network-news/ptech-board/~board/p-tech/post/boss-academy-students-honored-at-brave-enough-to-fail-gala

Mr grace (talk) 12:01, 7 September 2026 (UTC)

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