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History

Gwen Webber-McLeod, Founder

You Can’t Fail, Inc. is a nonprofit company with 501(c)(3) charitable organization status. Gwen Webber-McLeod, President/CEO Gwen, Inc. and Founder of You Can’t Fail, Inc., dreamt about creating an organization that would provide strategically designed multicultural leadership development experiences for emerging and established women leaders. These experiences would explore and place emphasis on the unique leadership journey of professional women of color.

Gwen believes that part of her purpose is to pave the way for the next generation of emerging women leaders and is committed to opening doors for professional women of color. Within one year of incorporating a private sector leadership development corporation, Gwen, Inc. hosted the first You Can’t Fail: Because Your History Says You Can’t Conference in the fall of 2009. The conference was a great success attracting 100 women from across New York State in its first year.

Gwen, Inc. continued to host the You Can’t Fail conference annually and to date has impacted the lives of more than a 1000 women via the conference and related workshop events.

After seven years of producing the conference Gwen Webber-McLeod transitioned the conference into its own free standing nonprofit company, You Can’t Fail, Inc. Her dream became a reality on June 25 2015 when You Can’t Fail, Inc. received designation as a nonprofit company. The company will continue producing the annual You Can’t Fail Conference while providing additional leadership development workshops and collaborating with other organizations.


Mission Statement

You Can’t Fail, Inc. is a nonprofit company whose mission is to provide strategically designed multicultural leadership learning environments for professional women of color and those who support them, “Unexpected Leaders,” and other young women and individuals who are striving to build their self-esteem and grow personally as they build a successful leadership path.

The Unexpected Leader™

You Can’t Fail, Inc. founder, Gwen Webber McLeod has been intrigued by the unique leadership journey of professional women of color and other women for many years. Throughout her career she noticed women do not have the same experiences as male leaders while rising to the top of companies and organizations. Her own leadership journey made her realize how often she is experienced as unexpected, and how frequently her talents, skill and leadership could be questioned because of her gender and race. This inspired her to think specifically about all of the factors impacting women leaders, particularly professional women of color. She coined the phrase the “Unexpected Leader™” to define this unique experience.

The Unexpected Leader is one who bursts on the scene shaking things up because they break the mold of traditional leadership. While earning a master’s degree, Gwen Webber-McLeod’s research focused on developing this specific type of leader. She found that “Unexpected Leaders” navigate the dynamics of being:

  • The “First and Only.”
  • Gaining and Sustaining Credibility
  • Paying Success Forward to Other “Unexpecteds”

The You Can’t Fail, Inc. mission was intentionally created to position the organization to provide support and specific leadership development experiences for Unexpected Leaders. The annual You Can’t Fail Conference is designed with the Unexpected Leader in mind.