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Jason Woolf
CEO / Co-founder, SidebySide Township Development
🤘 Rockstar
Member for 6 Years
Joined December 2018
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About me

Jason was born in the U.S. shortly after his South African parents immigrated to the country. He designed his own degree at New York University called Social Entrepreneurship and Cultural Revitalization, a degree with so much freedom that it allowed him to live in Khayelitsha—Cape Town’s largest township—for a year to build out Umbiyozo Foundation, the umbrella youth development organization he founded at age 17. Equipped thereafter with relative fluency in IsiXhosa, intimate knowledge of the townships, and heightened consciousness of a world and country with vast economic and cultural disparities, Jason is partnering with tourism to bridge worlds.

Jason has served numerous tourists ad hoc through Umbiyozo Foundation, but started officially guiding in 2017 once he became registered by the National Department of Tourism to guide throughout the Western Cape and Eastern Cape regions.

He feels that South Africa has the perfect blend of assets and opportunities to use tourism to become a model of global co-existence and poverty alleviation for the entire world. A nascent democracy, novel and authentic customs, and a vital, humble spirit are but a few of SA’s most special drawcards for visitors seeking to find and offer hope of a better, shared future.

Although living at home with his 94-year-old grandfather, he intends before long to move to Langa, Cape Town’s oldest township that leads the way in tourism. In his leisure time, he enjoys playing guitar and singing, playing tennis, hiking, and taking joyrides on his moped.

Jason Woolf Background & Credentials:

• Social entrepreneur, musician, cultural activist
• Dual citizen of US and South Africa
• Registered tourist guide with Professional Drivers Permit in SA’s WC & EC provinces
• Lived in Khayelitsha for a year in 2014/2015
• Speaks isiXhosa semi-fluently, and has great rapport with countless performing artists and entrepreneurs in the townships
• Over course of 7 tireless years built up Umbiyozo Foundation, which today has entirely black leadership
• Graduated cum laude in 2016 from NYU Gallatin w/ self-designed B.A. degree in “Social Entrepreneurship & Cultural Revitalization”
• Member of the Tollman family, some of the world's greatest tourism magnates (The Travel Corp, Trafalgar Travel, Red Carnation Group)
• Backed by Doug Band, President Clinton’s right-hand man and President of Teneo Holdings (see rec. letter attached)
• “Jason is not only the heart of his Watson class, but the Watson alumni at large.” — Quote from Eric Glustrom, President of Watson Institute (a social entrepreneur accelerator in Boulder, CO)
• “Jason will not just be very successful, but extremely successful in his career by his early 30s” — Quote from Anthony Evrard, CEO of Court 16 (a burgeoning NYC kids sports start-up)
• Featured by Global Citizen for Global Citizens of America Series
• Given a TEDx talk entitled, "Imagine a Culture Revitalized"
• SidebySide publicity: Interviewed on Cape Town’s #1 radio segment and featured by Invest Cape Town under their Success Stories series.
• Currently being sponsored office space by Greenpop

Why did you join the community?

Growth and exposure

What is your favorite travel destination?

Cape Town's tonwships!

Where do you dream of traveling to?

Mexico, Brazil, India — all countries with high inequality

What was your first travel job?

Programme Development Manager – Spirit of Africa

What do you want to learn more about?

How to successfully get tourists involved and exchanging skills/knowledge — moving beyond sightseeing.

Three words that describe why we should travel?

Perspective. Courage. Acceptance.

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