Big bet philanthropists don’t fund “best practices.” They fund breakthroughs.

In this episode, Hillary challenges the idea that multimillion-dollar philanthropy is unpredictable or out of reach. She argues that big bet funders behave less like traditional donors and more like venture investors—seeking leaders who are building for exponential impact, not linear growth.

You’ll hear Hillary’s latest thinking on the difference between linear and exponential change, and how to spot the difference in your own work. Then, she’s joined by social impact entrepreneur Tomo Hamakawa, co-founder of Earth Company, to explore the Dragon and Phoenix leadership archetypes—and why Phoenix leaders, supported by strong Dragon systems, are uniquely attractive to big bet funders.

Mentioned: Conrad, C. A. (2024, August 6). Lever for Change: How ‘big bet philanthropy’ is transforming the sector. Candid.

Hamakawa, T., & Yamamoto, K. (2024). The innovator’s tale of the phoenix and dragon. Stanford Social Innovation Review.

The Economist. (2023, February 9). How a tide of tech money is transforming charity.

Smith, T. (2023, May 14). The greatest wealth transfer in history is here, with familiar (rich) winners. The New York Times.

Starr, K. (2024). Big bet philanthropy: Scaling. Stanford Social Innovation Review.

Guest: Tomo Hamakawa is a seasoned development professional having lived and worked in various corners of the world from the Tibetan plateau, Indian drylands, Indonesian tropics, to Japanese metropolises. He has held positions with international and local NGOs across Asia and Africa, including the World Bank, Kopernik, and the Children’s Investment Fund Foundation, and previously served as an Assistant Professor at the University of Tokyo’s Global Leadership Program.

As the Co-founder and Chief Exploration Officer of Earth Company, Tomo helps visionary changemakers across Asia accelerate their impact through long-term tailored support. Earth Company also delivers innovative educational programs, offers strategic consulting, and manages Mana Earthly Paradise—the first B Corp–certified hotel in Southeast Asia.

Tomo’s work bridges organizational development, personal transformation, and regenerative design. His widely read essay “The Innovator’s Tale of the Phoenix and Dragon” was published in the Stanford Social Innovation Review in multiple languages. He holds degrees from Harvard College and the Harvard Kennedy School, is a two-time East-West Center Fellow, and received the Dalai Lama’s Unsung Heroes of Compassion Award in 2014.

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