Black Swans: Philanthropy Needs to Bet Bigger

For centuries, Europeans had a saying: “as rare as a black swan.” It meant impossible, because everyone “knew” swans were white.

We're Looking for the Black Swans in Education

Then in 1697, Dutch explorers off the coast of Western Australia spotted something unthinkable: a flock of jet-black swans gliding across the water. In an instant, a “truth” that had lasted for over a thousand years was overturned.

Author Nassim Nicholas Taleb used the Black Swan as a metaphor for rare, unpredictable shocks with massive impact, events like 9/11, the 2008 financial crisis, or the COVID-19 pandemic. They remind us how fragile our assumptions can be, and how suddenly the world can change.

In 2021, Paul Graham, co-founder of Y Combinator, extended the metaphor to investing. He observed that nearly all venture capital returns come from just a handful of unexpected winners. History proves his point: Steve Jobs turned Apple into a company that reinvented computing, music, and phones. Google transformed how we access knowledge. Amazon rewrote retail and cloud computing. Tesla revolutionized the auto industry. Airbnb changed travel. And now AI is reshaping nearly every sector in real time.

I believe the same principle applies beyond startups. At The W.W. Reynolds Companies, a few pivotal real estate projects and relationships have created disproportionate value over the decades.

The same is true in philanthropy: one bold idea, one inspired leader, one breakthrough program can ripple out to change countless lives. My Foundation will take this Black Swan philosophy and apply it to the nonprofit world. We will fund startups that may seem “crazy”

Our Three Pillars

and are led by entrepreneurs who may not have worked in this field before. The grants will begin modestly, but if the work shows real promise and aligns with our three pillars for a meaningful life — Free Market Education, Financial Literacy, and Civic Engagement — we will continue to fund, perhaps with others as well, with the hope of nurturing true game changers.

Khan Academy is a perfect example. In 2004, Sal Khan, a hedge fund analyst, began tutoring his cousin in math by posting short YouTube lessons. Working out of a walk-in closet and living off savings and his wife’s income, he self-funded the effort for years. In 2009, philanthropist Ann Doerr visited him in that closet office, gave $100,000, and later joined the board with multi-million-dollar support. A year later, Google’s Project 10^100 added $2 million. From those unlikely beginnings, Khan Academy has grown into a global learning platform with over 145 million registered users in 190 countries. What began as a “crazy” idea — free world-class education for anyone, anywhere — has become one of the great black swans of philanthropy.

Another striking example is Teach For America. In 1989, Wendy Kopp proposed the “crazy” idea that top college graduates could be recruited to teach in underserved schools for two years. With almost no resources and plenty of skeptics, she launched the program with just 500 teachers. Today, more than 70,000 alumni and corps members have reached millions of students.

A third is Muhammad Yunus and the Grameen Bank. In the 1970s, Yunus pioneered the radical idea that very small loans, often just a few dollars, could lift the poorest people, especially women, out of poverty. Economists dismissed the concept as impossible. But microfinance proved transformative, spreading to dozens of countries, creating millions of small businesses, and eventually earning Yunus the Nobel Peace Prize in 2006. What began as an experiment in one Bangladeshi village became a black swan that reshaped global development with small loans in developing countries.

History is full of similar long shots in all fields. Each began improbably, yet each reshaped lives on a massive scale.

We will place small bets on big dreams and passionate entrepreneurs because one of them will change the non-profit world.

You can’t predict where the next black swan will appear, but you can with an open mind fund people who have a passionate cause that may seem crazy to most and could fail.  We are looking for those outliers like Steve Jobs who did not take no for an answer.  We likely will strike out and ground out more than we reach base, but we are looking for those home run hitters. Black Swans. 

Reach out to us if you think you have the passion to take your ideas to the world.

-Bill Reynolds