Learning from a Legend Oprah Winfrey

Oprah taught me the power of mentorship and running a charity like a business to achieve the greatest possible impact on lives.

One of my earliest champions and my most inspiring mentor is Oprah Winfrey. She is an incredible teacher who showed me how to build a charity into a global movement and how business can be a force for good in supporting philanthropic ends.

I first appeared on the Oprah show in 1999 at the age of 16. During the broadcast, which showcased the work we were doing at Free The Children, Oprah announced a commitment to partner with us, through her Oprah Angel Network, to build schools around the developing world providing access to education for thousands of children, especially girls. You can see by the look on my face how shocked I was. 

Her pledge evolved to support a holistic development model to provide education to children by building schools and removing barriers to education through helping empower the community.

In the end, we built 66, not because she didn't fulfill her monetary pledge but because we worked together to do more than simply build schools.

From those earlier roots, we would provide development support through a 5-pillar development model grounded in education, clean water and sanitation, food security, healthcare and alternative income programs. To ensure the long-term success of this system, we would typically support a community from five to seven years, working with residents until they were fully self-sustaining.

“I quickly learned that Oprah didn’t throw her money around recklessly and she invested millions more into scaling our operations to ensure proper checks and balances were in place.”

Oprah’s commitment was by no means a blank check. Every month we went before her Chief Operating Officer to report on progress, and every quarter we had to present to her board of directors. I quickly learned that Oprah didn’t throw her money around recklessly and she invested millions more into scaling our operations to ensure proper checks and balances were in place. That is one of the key reasons she and her projects have such a lasting legacy.

Years later she turned to us again to help run one of her signature programs, the O Ambassadors Program. Free The Children provided the back-end support of the multi-million program in partnership with Oprah's Angel Network. Based on the U.N. Millennium Development Goals, the school-based program connected 1 million North American youth in 2000 schools with their peers in developing countries. Over 65% of the participating schools were title-1 schools. 

The O Ambassadors groups raised money to support development projects for marginalized children in Kenya, Sri Lanka, Ecuador, Ghana, India and Sierra Leone.

Groups of O Ambassadors travelled to Kenya to learn about local customs and culture, and the hardships endured by people their own age.

It all seemed relatively normal then, but when I look back on it, it’s hard to believe a 16-year-old Ontario kid could work side by side with one of the most powerful women in the world. 

Mentorship is one of the most powerful tools for good that we have and it’s a lesson I always try to pay forward in life, mentoring the next generation of activists and change-makers.

In the aftermath of the devastating 2004 tsunami in south Asia, which killed tens of thousands and destroyed infrastructure, including schools, we again joined forces with Oprah's Angel Network. Oprah asked us to build and launch a new vocational center in Sri Lanka. Named The Oprah's Angel Network Center For Learning, adults could attend to receive critical job training to help rebuild their shattered communities and children were provided an education and desperately-needed school supplies.

Oprah, her viewers, and others funded this in honor of Nate Berkus, an interior designer who frequently appeared on the Oprah show. Nate and his partner (photographer Fernando Bengoechea) were in Sri Lanka when the tsunami hit. Sadly, Fernando disappeared in the waves and was never found. In a deeply moving experience, I hosted Nate when he returned to Sri Lanka many years later to find closure and honor Fernando’s legacy.

At WE Day California in 2017, Oprah was in attendance and honored by the audience for her work, including in South Africa, where the Oprah Angel Network built the Oprah Winfrey Leadership Academy for Girls. Mpumi Nobiva, a graduate of the Academy, was a guest speaker at the event. During her speech about the importance of creating new generations of women leaders from across the globe, Mpumi thanked Oprah for building the school. 

Together, Oprah and I have worked together to create educational opportunities for children, particularly girls, in parts of the developing world where they would never have been able to attend school. It was an honor to partner with her to motivate countless youth in North America and beyond to be ambassadors for positive change.

Read More