Am I ready for Big Bet Philanthropy?

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.

Transcript

My name is Hillary Frances, and one of the things that I'm thinking about is what makes an organization appealing to big bet philanthropists, those who make multimillion dollar investments in a single organization with the intention of transforming a sector issue or organization. We all have our channels set to Melinda Gates and Mackenzie Scott, only two of many philanthropists whose names we drop when we want people to know we are paying attention to philanthropy. But I think a lot of us pay attention to philanthropy, especially big bet philanthropy, and have this maybe someday mentality about it. And yet as unpredictable and disorganized as big bet philanthropy seems, I think there are two things we can communicate about our work that attracts investors like them. 

You're listening to tailwinds ideas, fueling nonprofit innovators and social entrepreneurs. Tailwinds is a project that brings momentum to the leaders tackling the world's most impossible problems. Today's episode is three parts. Part One, my Latest Learning on What Big Bet Philanthropists are Interested in. Part two, you'll hear pieces of my conversation with Tomo Hamakawa, a social impact entrepreneur who has worked with investors and is now incubating entrepreneurs in Southeast Asia. He's going to help us think about big Bet philanthropy through the lens of two leadership archetypes. And three final thoughts on what to do next. 

So part one, what can we do to position ourselves for big bets? This type of philanthropy operates like venture capitalists and that it follows big ideas. So I wanna share the characteristics of a big idea, but first, we are discussing this topic despite the questions we all have about the future of philanthropy in this country. Here are a few things to remember. We are at the edge of the largest intergenerational transfer of wealth that we have seen in the United States. $16 trillion will be transferred from older Americans to millennial and Gen X heirs in the next decade. Millennial and Gen X philanthropists are more entrepreneurial in mindset, often favoring investments in scalable models over sustaining incremental progress, which means that Big Bet philanthropy is on the rise and will continue to gain momentum. 

Big Bet philanthropy is the practice of making multimillion dollar investments in a single organization with the intention of transforming a sector, an issue, or an organization. This is not to be confused with trust-based philanthropy, which is the practice of giving unrestricted gifts of any size. It's interesting to me that a large majority of the wealth that we're talking about originates from the tech industry. A 2023 article in The Economist found that roughly three quarters of the $33.4 billion given away by America's 50 biggest donors in 2021 came from people who made their money in tech. This is interesting to me because it gives us a big hint as to how these donors make their giving decisions. If we think about how they made their money, how they made their money, it was likely by investing in companies that build solutions. In fact, they were likely the founders or early employees at those companies. Remember, Mackenzie Scott's wealth is tied to Amazon and Melinda Gates is Microsoft. So if we just look at those two, we can see that they would be looking for the capacity to bring a transformative solution to a problem. 

So here's how we set ourselves up to be attractive to Big vet philanthropy. 
First start thinking about exponential versus linear impact. Linear impact is an equal proportion of inputs to outputs. When we describe our linear impact to a funder, we may talk about adding staff to serve more people. Adding a new site to serve more people, or even deepening the impact on those we serve, we're in effect saying, help us be Bigger and Better. Linear impact. An example, a food pantry distributes groceries to families in need. Every $10,000 raised allows the pantry to purchase and distribute a fixed amount of food, let's say 500 boxes. If the pantry raises $20,000, it can serve 1000 boxes. 

Exponential impact is different. Exponential impact happens when we expand via doers at scale. It requires that we are no longer the singular entity working on our singular mission. We are equipping others to deliver the model that we created. Others could be other organizations or government agencies or for-profit companies. So for thinking about exponential impact, we're wondering is there something we already do that we could teach others to do? Is there a consulting arm or licensing of our products we could offer? And are we working on systems change? Are we ready to begin advocating for policy changes hand in hand with the community that paves the way to scale? Another question, is there a commercial adoption of our model? Are their for-profit partners that are already benefiting from what we do? That might find value in offering it themselves, like workforce development for their own employees. A for-profit company could offer that rather than our own nonprofit solution. So another concrete example, let's go back to the food pantry instead of running a food pantry. They become a food justice nonprofit and invest $10,000, that same 10,000, to create a peer led training program that teaches communities how to start their own neighborhood gardens and food cooperatives. Over the next year, the trained leaders launch 10 gardens on their own, and each garden feeds dozens of families without needing another 10 grand from the organization. 

So if the first way to set ourselves up for Big Bet Philanthropy is to think about the difference between linear impact we create and what exponential impact would require. The second way is to think about our approach to problem solving, and that's where Tomo comes in. 

You are going to hear us talk about the concept of Phoenix and Dragon type leaders. We use a sort of shorthand when we talk about these two archetypes in our conversation. So let me give you a few notes. In Dragon Mode, an organization narrows down their work in concentrates resources. In Phoenix mode, an organization is able to embrace complexity and experimental ideas. In Dragon Mode, there are static hierarchies. In Phoenix Mode, there's an Agile team culture. In Dragon Mode, managers focus on alignment and progress against a plan. In Phoenix Mode, progress is a given, so the focus is on sharing lessons and knowledge with the field. In Dragon Mode, everyone is oriented toward fixing a problem. In Phoenix mode, we are creating new value, and I've decided to play the parts of my conversation where Tomo shares a couple of stories from his past because I want you to hear how he thinks he is a non-anxious presence. That can come from a number of things, but my guess is that he's moved beyond the phase of his life where he's really driven by achievement and impressing people. And yet you'll notice that he's one of my most accomplished friends. I think this non-anxious presence is a quality that we're all trying to cultivate, but his is deeper than just being Zen. I think if the two of us were sitting at a conference room table and an investor walked in and we both had pitches. To give of our equally impressive startups. I think the investor would already have chosen tomo over me because he is slightly less anxious, and maybe that's the quality of a Phoenix leader we're looking for. See what you think.

Today's guest is someone who has profoundly shaped how I think about leadership transformation and what it actually means to build a regenerative world. His name is Tomo Hamakawa, and we met in the most modern way possible. I read an article, he wrote this helpful and curious piece about the Dragon and the Phoenix in the Stanford Social Innovation Review, and I cold emailed him. Not only did he respond, he invited me into conversation and that conversation led to one of the great privileges of my professional life getting to do pro bono work with his Global Impact Heroes Program. Tomo is the co-founder and Chief Exploration Officer of Earth Company, which accelerates visionary change makers across Asia through long-term tailored support. He has led and advised organizations across Asia and Africa, including the World Bank, the Children's Investment Fund, foundation, Kopernik, and more. He's taught global leadership at the University of Tokyo, and he's received the Dalai Lama's Unsung Heroes of Compassion award, Tomo's on the Flying Whale Board of Advisors because he's someone who I'm constantly learning from in particular on the topic of scale, which is why I am so thrilled. You get to hear from him about that today. If we could do this interview in a location that would represent your work, where would we be and what would be going on in the background?

Such a privilege and honor to, to be here with you in this virtual room. Hilary. Um, if we could do this, I would be in. Nature in the woods, in the forest, in the jungle. I, um, I'm based in Bali, which is an amazing place, full of nature, biodiversity and all these things. And actually just two days ago I had the, privilege of going to this village and actually doing a little bit of hiking. In the mountains and yeah, and I, for some reason I had this really bad headache for about a week, and that that experience that totally like got me better and now the headache is gone. And so, yeah, it's just for me, reconnecting with, with nature in, in, in the jungle or in the, in the ocean it's such a important. Reminder for all of us, especially in the work that we do. 

So, in terms of the work of Earth Company it's focused on the Asia Pacific. But that's a really expensive, part area of the world. Um, it, so we cover from the Afghanistan in the west to the Pacific Islands in the East, and we focus on the developing country. So we exclude the so-called advanced. Economies like Japan, Korea, Singapore, Australia, that still leaves about 35 plus countries in the region. So it's, also more home to more than half of the world's population. Right. And so it is. When we talk about Asia it's really the of the, the world's population with the most pressing challenges.

So I wanna get to know you a little more. I actually don't know the answer to this question, and I've been curious about what it took to be award the Dalai Lama's Unsung Heroes of Compassion Unsung Hero's Award. What were you doing at the time?

So I also don't have the answer to that. I'm still trying to figure that out. Um, and it's one of these wonders in life, um, because I'll tell you a story. So the reason why I was nominated back in 20. and this is actually before we started Earth Company, so back in, in my, in my twenties. So I'm, I'm 45 this year. So in my twenties, this is like the two thousands, right? Um, I, my first full-time job was working for a an NGR called the Bridge Fund on the Tibetan Plateau. and so. In from age 24 to 26, I, I worked for a small NGO alongside amazing Tibetan coworkers trying to improve educational standards, protecting the environment, you know, preserving the culture and all these things. And through that work, I had the, um, pleasure of meeting one of the organizers of this award, um, on Unsung Heroes of Compassion. And I, then I probably didn't even know about the existence of this award, but then a few years later, I got this, email from The organizer, Dick, Dick Grace, amazing philanthropist, and he emailed me saying, I'm coming to Japan. 'cause he was supporting a lot of these. Projects in Japan after the big earthquake in tsunami. So he had been, you know, doing this kind of work like, you know, making, contributions to schools or scholarships in, Tibetan areas, Nepalese communities. And so he was just coming to Japan in, in, the context of that. And then we, and I was like, oh, great, Jake, let's, let's meet up. He was staying at a hotel in Tokyo. And so we met up at a Starbucks nearby. And then we were catching up and then he says, oh, you know why we're meeting today? like, not really. Like, I thought we were just catching up he was like, oh, so I am, I'm involved in this award. I was like, like, I, I mean, until, so I was about, I was 33 at the time, right? Like I had worked A couple of jobs very interesting work in Tibet. And then I was, I think at the time I had just finished working for the Children's Investment Fund Foundation working in India and, and, and the uk. So very much in kind of the international development world, right? But I hadn't started anything on my own. Um, so I was like, that's really humbling and great, like, you have selected me. Like I, yeah, I have aspirations to do great things, but I, I have nowhere close to, know, to, to be deserving this. Right. And so, I actually started talking about my partner Aska and that conversation, and she was working in, actually in the disaster struck areas in Japan. And then Z was like, oh, send me more information about her as well. And so. I think it was like the next day he was, he said, okay, well we wanna nominate both of you this award. So we were like, oh, what do we do? Right? And so we actually, um, politely declined at first and then the response, um, that Jake gave kind of convinced us, and there were two, two things. One is that he says. This is not for, for the work that you've done, but all the, the hope that you will do great things in the future.

I like that.

Yeah. And then the, so this is actually related to this conversation, right? It's about, you know, so the kind of, the, the Big Bet Um, and then the other part was that we could fly any anyone any one person as a guest. For this event in San Francesco at the Ritz Carlton. And so we thought, okay, well, I mean if the spotlight is not completely on us, but we can actually bring someone, then it will actually, you know, we can start a chain of positive reactions. Right? And so, um, and we actually brought Bella. Who ended up becoming our first impact hero to San Francesco because we thought that she was much more deserving um, than than us. And then in, in San Francesco, Bella told us about her work and her dreams of starting an environmental education facility in rural Timor. And then the whole thing was that the government had committed to, supporting it, but then actually withdrew at the end because there was no precedent of supporting a woman leader in that way. And it was like totally ridiculous, right? And so we were like furious and we were like, okay, we'll do whatever we can to, to support you. And so we did some crowdfunding we raised about $50,000 just to. to, for her to get started. Right. And that was really the, the, the, the initial seed of Earth Company as an organization. Like we want to do everything we can in our capacity, within our networks to support these amazing heroes. So this whole Dalai Lama thing is, is still a, an enigma to me that I'm trying to figure my life, through my career, but it's also deeply connected to how earth companies started and how Bella Bella's work and are, you know, paths have crossed. Um, so it's, it is, it is a really a, me, if anything, it's, it was really a blessing from, from His Holiness to towards what we do.

Well, it sounded like it was a front loaded investment in you. We're awarding the future of your work, not the past of your work. I love that.

Hmm. Yeah. It's, it's a beautiful way to frame it.

Yeah. So in that sense, you're right, this does relate to the idea of Big Bet philanthropy, I feel like it's part of my job to help leaders answer the question, what are Big Bet philanthropists looking for? What is the recipe to be attractive to the kind of donors who make multimillion dollar investments in an organization that they believe can transform the sector or an issue once and for all? And so I've been looking for a formula and I have found your framework to be one of the most helpful. But I don't know if you would agree with me, that's why you're here. To tell me if you think this framework is actually relevant to the idea of Big Bet philanthropy. So I'm gonna give away my, my hypothesis and then you tell me what you think, which is that, I think that leaders who have a background in Dragon characteristics, and we're gonna have to explain to people what these are in just a second. Leaders who have a background in Dragon but are currently acting as Phoenix leaders are the perfect fit for Big Bet philanthropy, um, meaning that they have experience in solving problems according to the rules that we're all familiar with. But now they've reached a point in their career where they're breaking those rules and they wanna solve problems by breaking the rules.

Yeah. This whole idea of the dragon Phoenix was a really liberating experience for me. I do think this dragon phoenix thing is kind of a spectrum. It's not, it's, think, think it's so much binary, but it's really a spectrum. Like where do you fall on the scale? Right. And I am very phoenix and the, the reason why it was liberating for me is because I was. I was asked to, and I was exec expecting myself to be a dragon, and I found that to be very suffocating stifling and not maximizing my strengths, my values. You're very dragon and you're asked to be or expected to be Phoenix. It's very uncomfortable and it's not something that you can do very well, and you can pretend and I can, I can pretend to be good at Dragon, you know. But it doesn't last very long. But, but let me, let me explain. Um, I backtrack a little bit because, so back in 2022, I, started to think about these issues all these nonprofits, social enterprises are doing amazing things. But then if you look at the problems, if you look at the, you know, the, the bigger context, the problems are not gonna be fixed at the rates that they're being fixed. anything, the problems are getting bigger because of climate change, because of social inequality, because of crazy political leadership. And that's when I actually was introduced to my co-author, Keita. And he comes from, um, a nonprofit management background. when, he actually shared with me this, this table, this simple table. It wasn't called Dragon Phoenix back then, but in Japanese it was called problem solving. That was the dragon side. then the, the Phoenix side was called value creation.

And then it had, back then there were five, um, kind of rows, you can imagine a table. So it was like vision, business, strategy, communication, and members. And they were, um, it was basically contrasting between the problem solving mode, which is what's called Dragon now, the value creation mode, which we now call Phoenix. When I came across that and when he explained it to me, I was like, oh my God, this is gold. few years later he had, he shared this framework with me and I was like, we need to. Let the world see this. We need to, you know, put a little bit more shape ideas because I have been struggling with this and I feel like so many people have been struggling with this. And so we started the process in April, 2022. We started having like monthly meetings about this, and then, um, it, it took us. About a year and a half to get it published in the Stanford Social Innovation Review, in September, 2023. But the longest period that we spent in that year and a half was actually coming up with settling on the animals Dragon in we needed, we need animals. Right. When your, your organization's flying whale, right?

Yeah, it, it helps.

It helps. Right? And we, we, yeah, we were thinking is it a giraffe? Is it a lion, is it a peacock? Like we, we went through like the entire animal kingdom and probably a good chunk of the plant kingdom, right?

This is the best part. Okay.

And then we, we actually, so the dragon Phoenix is actually, um, kind of an ancient Asian, idea from the, from the Chinese tradition. And so, and it's, it's usually used in this yin yang kind of way. And we thought, okay, this, this makes sense. Um, and from the beginning it's, it was always that not about the one is better, the, whether the other is worse. So it's not good about it. It actually, we need both. Within an organization, you know, um, to, to flourish and to, to, to, to grow

Do you have a cartoon character or a movie character or a book character that you could help us visualize who a Phoenix leader would be and who a dragon would be. I thought about this a little bit and I, the, the best I could come up with was Jason Bourne is a phoenix, but help me, help me. What, what

Who? Who, who is the dragon like in that...

I mean, I don't have a good one. I'm thinking of like a very type A person who wears khaki pants.

Right, right.

And uses, um, Microsoft products. I'm using my own imagination without your correction here.

Yeah. No, that's, that's really interesting. The, yeah. Um. So the, the very first metaphor that, that Keita has shared with me in the, the very original conversation was actually referring to kind of these games, video games and animation, which you may not be familiar with, but some people may be. Interestingly problem solving was actually, um. Dragon Quest, which is a very popular video game. Um, and it's interesting that the word dragon is in there. Um, and then the Phoenix was actually this mega hit anime called One Piece, and it's still actually ongoing and it's, yeah. So Dragon Quest is a, it's a role playing game, you know, that was started in the Nintendo era. and it's basically these, they're like four people that like go through these like different, dungeons and different stages and they, it, the, the idea is to actually kill the big bad boss, right? And so you go through these stages and so it's very clear what the, what the mission is. And each player is, you know, has its own strengths to, to kind of fight the right? Different opponents. Whereas one piece is not about a clear mission, it's actually more about they're on a journey. It's, it's really about a journey. It's not beating this specific person or specific, you know, idea. And so there are pirates, um, that are kind of on a journey, um, and. about enjoying that process. Right? And so that to me was a perfect analogy.

That's really helpful. So now I'm nervous that my theory about what Big Bet philanthropists want is wrong, but I would love your thoughts on this. What do you think they're looking for?

I, I do think in terms of Dragon and Phoenix, Big Bet philanthropists on your definition and perspective. I think looking for more Phoenix type Because they want to see catalytic exponential change as opposed to linear change. And we all know that any of these problems that we're dealing with are not gonna be solved at a linear rate. And so they, we we're looking at how do we, you know, create this reach that tipping point where that solution actually is spread. Um. In an exponential way. Um, so think Phoenix, leaders I think appeal more to Big Bet philanthropists in general. But the other thing is that as organizations grow, Phoenix type leaders need to be supported by Dragon members in the organization. Just because Phoenix, the role of the Phoenix is not to. and to create processes and systems. But if as organizations grow, you need systems and processes to be in place so that people know what the expectations are of working there. You know, they are, you know, legal protections, right? They are, um, and in place. And so I, I think it's, it's having that combination within an organization, um, to yeah, to attract these kinds of philanthropists.

I think we're in danger though of starting to think of Phoenix leaders as just being like crazy visionaries without much sophistication.

Mm. Yeah. mean, I do think the, the Phoenix type is, is really, is, is about exploring. Right. I mean that my, my, I've changed my title from managing director to Chief Exploration yeah, that's probably, um, a very symbolic change. Right. And, and I, like the managing director was probably the worst title I could give myself. Um, in the, in the, in the earlier phase of Earth Company. Um, but I think the exploration is, is not just about being visionary and do like going out there but it's also like making connections, right? Like pulling in resources from other organizations or creating partnerships. I think that's a, that's a really important part that we don't actually talk too much about in this article. But I think when we talk about collective impact, right? How do we create systemic change? You need to make those connections, those partnerships, those relationships. And without those relationships, like you're just operating in a silo. And that's a really dangerous, um, or limiting situation to

Yeah, yeah, yeah. Because if we're talking about exponential growth versus linear growth, we need, um. Other entities to implement the model. So it's one to many versus one to one.

Exactly. I mean, it's like we in the regenerative discourse, we often talk about the mycelium network, right? Like if you in the jungle, in the forest, you, we don't actually see it in the human eyes, but the, it's like just the jungle is just a giant mycelium network, right? And. We often forget that we need to, as organizations, we need to create those mycelium networks, connections with other entities, with government organizations, with, you know, academic institutions and so many players in the system.

I am curious if you know anyone in your network who is receiving Big Bet philanthropy or who you think is on track to receive it and what, what their traits are like, what combination of traits do you see in those leaders.

One comes to my mind. He is, he is an impact hero. Um, his name is Arief Rabik, and he is an Indonesian, bamboo, bamboo dreamer, if you will. And he, was a recipient of the, what's called a climate breakthrough, initiative. so climate breakthrough, I think is, is very much in, A Big Bet Philanthropy So they, they select, I think few people per year and they make multi-million, um, kind of investments or grants to, to these organizations. so what Arief trying to do is, um, basically create this idea called the Bamboo Village Projects. And so the idea is that bamboo has an amazing, benefits in so many ways in terms of climate, in terms of land degree, you know, reviving land, and also giving jobs in rural communities. And so. Um, he's established this model in, in Eastern Indonesia, and now what he wants to do is, is scale this up to 10 countries, you know, and have 10,000 bamboo villages throughout the tropical regions of, of the world, and. That has, you know, massive, carbon, impact and as well as economic opportunities. He actually was raised by this, A queen of bamboo. So his mother is, is, Linda Garland, who is known to be, really a huge, figure in spreading the, the magic of bamboo in architecture, in furniture, in everything that we, that we see today. And so he was, he received this, amazing bamboo education as a kid. Um, and so, I mean, he, I, I do think him as a, a real Phoenix leader.

So we're saying that the leaders Big Bet philanthropists gravitate toward might be those that have plans for delivering exponential impact and also have phoenix characteristics with a background in dragons. They have experience in problem solving, but now understand how to solve problems by breaking the rules and they have dragon problem solvers on their staff. It's a delicate balance of portraying your track record of success and being a renegade of having strong institutional roots, but also being at the edge of a breakthrough. So rather than worry about contorting yourself for the next open call, or contorting yourself to get a meeting with someone who knows someone at one of these firms, let's focus on doing two things. 

One, write a paragraph that conveys one way you are working toward exponential impact. And two, describe the horizons you're exploring and the experiments you're conducting, and that while you experiment, you continue to run an organization that's generating regular old impact. We're in your corner. 

Tailwinds is a production of Flying Whale Strategies, a consulting firm that is equipping teams to solve impossible problems. A special thanks to Tomo Hamakawa for the conversation on Phoenix and Dragon Leadership and his co-author Keita for bringing this idea to his attention in the first place. I'm really glad you spent a year and a half debating all the possible animals and plants you could have used for these archetypes. I wish I could have been. A fly on the wall. You can find a link to the article in the show notes, as well as links to other resources used in our research for this episode, if you'd like to learn more about Flying Whale Strategies, please visit our website at flyingwhalestrategies.com. Thanks for listening.