How to prepare for the King Tide Era

The nonprofit sector is entering a King Tide Era — a convergence of political, economic, and environmental pressures that won’t just strain the social sector, but fundamentally reconfigure it. 

Hillary explores uncomfortable questions: What if the nonprofit model isn’t the best vehicle for solving the problems we care about? What happens when philanthropy becomes volatile, identity-conflicted, and driven by instinct more than strategy? And what can we learn from mutual aid networks that are already operating without hierarchy, predictability, or formal structure?

Hillary is joined by Dan Reed of Praxis, a longtime collaborator and mentor, for a conversation that moves from personal apprenticeship to the future of capital itself. You’ll hear them talk about:

• The Impact Returns Reversal for philanthropists
• How we ask what’s possible versus what’s feasible and the Overton Window
• Philanthropy’s identity crisis
• How to identify leaders worth investing in within 5 minutes
• How our obsession with impact might be making us dangerous

About Dan: Dan Reed is a partner at Praxis Capital, an accelerator based in NYC supporting founders, funders, and innovators motivated by their faith to address the major issues of our time. Dan is animated by the power of generous, risk-forward capital to transform culture. At Praxis, he helps cultivate a community of funders committed to activating capital toward redemptive purposes. Previously, Dan served in leadership roles at National Right Work Committee, Denver Public Schools Foundation, and Morris Animal Foundation. In 2015, he founded Seed, a training and coaching company designed to help social entrepreneurs fundraise for scale. He loves the work of building new things and people that put their hands to the task.  Dan holds a BA in History and Philosophy from Geneva College. After many years in the mountain west, Dan lives in the small town of Beaver, PA.

Research for this Episode: 

A new mindset changes donors' relationship with philanthropy. 

What's your endgame?

The Innovator’s Tale of the Phoenix and Dragon.

The T-Rex and the Snowshoe Hare: What’s Next for Philanthropy in the 2020s. 

The Black Panther Party: Challenging Police and Promoting Social Change. 

What can mutual aid do in a disaster? 

Megatrends: Five global shifts reshaping the world we live in. 

Six paradoxes of leadership. 

Big Bet Philanthropy and the Big Shift to Working With Government. 

Philanthropic leaders reflect on major trends – and tensions.

Grappling With Systems Collapse: How Social Sector Leaders Can Respond. 

Coronavirus volunteering: how you can help through a mutual aid group. 

Transcript

My name is Hillary Frances and one of the things I've been thinking about is how badass many of the leaders I work with are. They're smart, fast, on their feet, and a bit rugged. By the time I meet them, they've become like special operators who don't get cold easy, don't mind sitting in uncomfortable chairs and know exactly what's happening behind them. They are the most elite professionals in the field. Uh. And yet they're asking for help preparing for their next assignment. It's my job to understand the nature of the next assignment for you all. The era, the nonprofit sector is moving into today's episode, what is the next era for the social sector going to demand of its leaders? I'm going to describe the era. As I understand it. I'm going to describe the unique pressures we're facing and what might be happening as a result. And finally, I'm going to play clips of my conversation with a mentor of mine, Dan Reed, who is working with impact investors across the country.

So part one, what is the next era for the social sector going to demand of its leaders? I'll explain this with a metaphor from oceanography. King tides are the highest tides of the year. They're caused by the alignment of earth, moon, and sun. They have the potential to flood existing systems. They are peak pressure moments, and yet they're not always destructive. They are capable of carrying nutrients into places that are normally left out of those nutrients. They're also a natural stress test that exposes weaknesses in coastal infrastructure. So to prepare nonprofit leaders for the King Tide era, we begin with identifying its characteristics. How high will the tide reach here? What will be the impact of sail a nation on our water sources? Which roads, sewer systems, or bridges will be impacted? Will any creatures get beached on the shore? Scientists have predictive tools to answer these questions and so should we. It's been really helpful for me to think of the time we're in, in the context of history. We've experienced high tides in the past, and this isn't the only big pressure moment.

I wanna run through three eras that have happened prior to this one briefly. So we understand what the social sector has demanded of leaders over time. So first picture a timeline that starts on the left in the 16 hundreds and spans to the right, to the present day. We have four stops to make on this ERAS tour. The first is the colonial era. That's the 16 hundreds to the 18 hundreds. This is the ground zero of the social sector in our country. For the first time, we had organizations that provided public services without the rule of a monarchy. Think universities and hospitals, Harvard, for example, was founded in 1636. If you were the leader of an organization at this time, you were motivated by figuring out how to provide public services without guidance from a monarchy. So we needed leaders who were free thinkers and had the confidence to test their ideas. Next stop on the timeline will be the late 1800s when we have the industrial revolution. This was a big deal in the history of social service organizations because there was an influx of wealth coupled with a growing wealth gap. Capitalism was showing its colors and the power it had to make wealthy people wealthy, and how it required low wage workers to fuel its machines. So we have an increasing demand for social services. The leaders of these organizations were concerned about rapid service delivery, deploying resources quickly. Not a lot of room for creativity here, but a great deal of patience and resilience. Next up is the mid 1900s where we have tax laws that specify new nonprofit expectations for a 501C3 for the first time. As nonprofits professionalized, they adopted corporate models for efficiency and legitimacy. The 1950s and sixties were a time of being ship shape so very quickly now, we arrive at the last stop on our timeline, which is present day, and I'm gonna say it begins in 2020 with COVID and includes the impact of Trump's presidency on philanthropy and the delivery of social services. 

If I could summarize what I think this era demands of social sector leaders, its creativity. Almost like a return to the 1700 where leaders were inventing how services were delivered for the first time. Here are a few characteristics of this era. We are experiencing new political pressures. Civil rights are not a priority for our federal government, federal deprioritization of civil rights, voting rights, LGBTQ plus protections, and reproductive rights means more of this burden falls to the social sector. Organizations doing social justice work are threatened by anti DEI initiatives and feel the need to de-emphasize that work or increase protections. 

Number two, we're experiencing new economic pressures. The federal government is an unpredictable source of revenue for the social sector. Philanthropy is unpredictable. Volatile markets may make donors cautious, delay giving or restrict funds. But philanthropy could also surge when donors respond to these crises with increased generosity. We're also seeing the cost of doing business, including wages, supplies, facilities, is rising sharply with social enterprises, particularly exposed to this. 

Environmental pressures. Rising sea levels wildfires, extreme weather, are creating new waves of climate migrants, and increasing demand for emergency and housing services. 

So if those are the characteristics, I have three observations about the impact of these pressures on the sector. First observation, nonprofits may no longer be the best model for service delivery. We may be entering a time where the nonprofit structure may not be the best model for solving the problem we're trying to solve. Public systems will offload responsibilities to nonprofits without corresponding resources. Executive orders have already limited government support of public health, housing education, and food security. Government regulations may ramp up to suppress or even end nonprofits influence, and then tech enabled private actors may out compete nonprofits in speed data use, and perceptions of effectiveness. Especially in areas like education, workforce development, or housing. So the nonprofit model itself may not be the structure we need moving forward. 

Observation two. Philanthropy is disorganized. Just like we discussed the eras of the social sector. There have been many eras for philanthropists, the patronage era of the 15th century, where wealth benefactors like Lorenzo de Medici supported artists like Michelangelo and Da Vinci. We had the industrialist era in the late 1900s where the Carnegies and the Rockefeller's funded elite institutions like libraries and universities to drive more industrialism. And even more recently, we've experienced an era of philanthropy beginning in the 19 hundreds, characterized by venture and tech wealth funding solutions to global problems through innovation, it's fueled applying the startup mindset to the social sector. And we've benefited from the predictability of these previous eras. Benefactors knew how to play the game in the era they were in. Now we're not so certain. Some philanthropists are doubling down on causes they care about. Spending down their funds like Bill and Melinda Gates. Some are freezing or limiting their giving and some are making big bets like Mackenzie Scott. Some are even criticizing philanthropy as perpetuating colonialism, and some are celebrating it. However, the most disorganized feature of philanthropy today is the rise of millennial and Gen Z donors. Millennial and Gen Z donors focus on what their peers care about at the moment. They're compelled by urgency and trends. They cancel things they disagree with. Their retention rate is lower this disorganized way of giving could result in pop-up nonprofits offering curb appeal or a survival of the fittest. The fittest being those that are most fit for the donors at the time. Donor loyalty to large established nonprofits could become a thing of the past. 

We also see that mutual aid is on the rise. In some communities, informal and hyper-local efforts are replacing formal nonprofits as trusted mechanisms for. Service delivery. Mutual aid groups are non-hierarchical, run by volunteers, operate off social media, Google spreadsheets, and they're full of people with differing ideological opinions. Historically, we could study the Black Panthers as a system of mutual aid that arose in response to democratic failures in healthcare, education and safety for black communities. More recently, we saw mutual aid arise in Minneapolis during the ICE Occupation, and before that, during COVID, where neighbors provided hyper-local support to deliver food, medicine and rent assistance. Mutual aid groups are seen more frequently when people lose faith in democracy, and so they turn to horizontal participatory forms of governance, which is what mutual aid offers.

I wanted to run this hypothesis by my mentor, Dan Reed. So I'll play clips of my conversation with Dan. Now, I'm really eager to share this conversation because it's a behind the scenes look at my learning process. As a consultant, this is the type of conversation Dan and I would've had for the six years we worked together. I want you to see how many of the things I bring to the table today originated through dialogue with Dan Reed. Dan is a partner at Praxis Capital At Praxis, Dan helps cultivate a community of investors and philanthropists committed to activating capital toward redemptive purposes dan previously served at the National Right to Work Committee, Denver Public Schools Foundation, and Morris Animal Foundation. In 2015, Dan founded Seed, a training and coaching company to help social entrepreneurs design and fundraise for scale. Today he and his family live in the small town of Beaver, Pennsylvania, which you'll hear me tease him about shortly.

Okay, Dan, so I wanna start by thanking you by saying thank you specifically for apprenticing me. I tell people how I got into this work through apprenticeship. I actually used that term. We met back in 2014 when my ex-wife and I were founding a nonprofit. We needed fundraising coaching. After that you were my executive leadership coach until 2017 when you helped me decide to quit that job. I asked you if you needed help with your consulting firm, and you offered me a job as your assistant. I remember I was terrible, really terrible at choosing restaurants in foreign cities for you to have meetings in. I remember we tried to use Asana but didn't really need it because we both also wrote everything in notebooks. You taught me how to follow along with the minutiae that a client is worried about, but also how to help them consider the one decision that could make that would make 10 other things easier for them. People say that I'm uniquely able to work with them in the weeds, but also help them with strategic decisions, and I learned that from you. We worked together for six years before I launched Flying Whale, and I just wanna take this moment here at the end of 2025 to recognize that long history we have

My, well, that is, that is a very, very gracious introduction. I do not remember, internalizing. Hiring you as an assistant, because if anything, it was the other way around quickly. I feel like right, right off the bat, we were just contending for what was good.

Hmm.

Contending for building the thing together. I mean, I think about six years, honestly, Hillary, and I think, just, I have the utmost affection and respect for everything that you poured into seed and really made seed what it is even today. So I think you're under, you're understating.

There was a time when you needed reservations at restaurants in like Florida for some reason, and you gave me that test

That was

and I was like, Googling restaurants in Florida.

Right, right. I'm sure that's true, but I'm, I, my mind goes to all of the time that we spent on taking a, what we believed was a principle that organizations needed to take into their work and take and one, contending for what was true about the principal. And then two driving it into actual content, actual curriculum, actual the ability to actually coach it and walk someone through that, not just from ideation, but to application. And so that's actually, again, your intro is very, very kind. But that's actually the work I, I remember most. And I'm, I'm super, I'm unbelievably proud of is, I guess just the work of. Rolling the sleeves up and contending for that.

Yeah.

And so we did that at Seed together. And and I think I'm, I'm just incredibly proud that both of what Seed's become, but, as much actually how that formed a point of view for you and, true for Flying Whale. So I'm, I'm really pumped for you and flying whale strategies, but also as I look back, really proud of just that, like that commitment to excavating what is most true and elemental in this work and driving that to some, some application that could be brought into organizations and alongside leaders.

I do miss that. You and I formed points of view through our work, and the reason I invited you to help me with this particular conversation about the next era for the social sector is because this is the kind of conversation we would've had back in the day, and we would've figured out our points of view through dialogue. So I am prepared for my thesis to change by talking to you about this. I'm prepared for lots of new honing of, of this idea. But before we talk about the King Tide era, let's learn a little bit about your current work. When we worked together, you were coaching social sector leaders and now you're coaching investors. So tell us a little bit about the investors that you're working with.

Yes. So at, so at Praxis our entire thesis, if you will, or our own kind of theory of change is that when we bring early stage entrepreneurs high imagination and risk forward funders and discerning thinkers. into the same room, are able to build what we call a praxis. Redemptive ventures, ventures that have a trajectory that are focused more on trajectory more than velocity. And that trajectory being how do we how do we make whole, particular areas throughout culture society, et cetera, both here in the US but also globally. my work in that is largely with the funder community of Praxis investors and philanthropists, that are seeking to reorient they work with their own capital. Out in the world externally. and so a lot of the coaching or the work, the program work that we do with investors and philanthropists is, is the work of reordering what we would call the impact returns reversal. So the, the, the dominant narrative in this work, in the work of capital allocation, at best is what impact can I get for the returns I'm seeking? That's a returns first lens. So many of the funders that we work with are, are like, they're, they're, they're interrogating that assumption and they're, they're, they're asking for, a partner. In helping them ask a different question, which is, what returns might I get for the impact I'm seeking? It's an impact first lens to say, what do I want to participate in the world? do I wanna participate in the world to bring a significant change to bear in a way that, in a way that secondarily or tertiary, in tertiary ways may produce a return. So it's fundamentally fundamentally reordering purpose of capital, which is that actually capital has an impact, whether you like it or not. You get to choose whether you you get to choose whether you and affect that impact. And so, I, I cannot speak highly enough of the investors and philanthropists within the Praxis community because these are individuals who are. Thinking critically, rigorously and challenging their own assumptions about how capital should work to to get after, to get after change across a myriad of issues across the globe. and, and so these are, these are investors and philanthropists that are, that are, that are re risking instead of de-risking. They're asking the question, what's possible, not what's feasible. they're asking different questions about, about their, their use of capital. And so that's, that's largely the work I get to do in supporting them in those questions. Yeah.

So I'm imagining this is the time. This is the time, as in lately, over the last eight to nine months, folks have been wanting to talk about crystal ball, thinking about the future of philanthropy, thinking about the future of the social sector, how is the new administration impacting it? How is the economy impacting what's possible? And so this is exactly why I wanted to hear what are some of the conversations going on in your head and also with your investors about this next era. And one of the things I've learned from you is that you don't always have to be right, but you should be clear. So I took a page from your book and clearly defined the era. That we're working in, and I gave it a name, the King Tide era. I thought we could go through my top three observations about the unique things we might see in this era. And I wanna see what you think. Okay, so observation one, nonprofits may no longer be the best model for service delivery. This idea comes from thinking about the new level of scrutiny on the nonprofit structure, the new level of management and oversight of what nonprofits can and can't do. And so we may be entering a time where that structure no longer competes with other models for solving the same problems. And so what should nonprofit leaders be thinking about in terms of their business model? I don't know. I think they should just be thinking about the fact that it does not have to be delivered through this traditional structure that we've been used to for decades.

So yes. So a couple quick thoughts. One is, I do, I do believe that for the entrepreneur or, or the leader that cares about solving or tackling or influencing major issue in the world, I do think that the nonprofit or business or everything in between structure follows suit. It actually follows suit. It doesn't, it doesn't come first. It's not a, it's not a, it's not the, it's actually the wrong first question. It's like the, it's probably the right, like fifth question, fifth, fifth


For entrepreneurs, or I would even go one step further and just say, and it's harder for a leader of a established organization ask this question, but I think it's still a valid one, which is what does the Quest require? So what, what does, what does the what, yeah, what does the Quest require? And that means what structure does the Quest require? What business model does the Quest require? And that should guide all of these strategic and, and, and financial modeling questions as well. I truly believe that I, and so that's kind of thought one now that doesn't, that doesn't necessarily support or, or reject the claim that nonprofits may no longer be the best model for service delivery. But it, at least it does suggest that it may not be, probably the nonprofit for many, many founders and many, many leaders. The nonprofit model, the nonprofit business model kind of been like the first given when it really shouldn't have been. and, and I think that's a very, very interesting question, which is like, if you were to look at all the nonprofits in the United States and you were to think like, well, what are they trying to solve? What's their quest? And that, and then, and then they answered that question without a nonprofit business model, what

Yep.

Right? What would that

Yeah.

my guess is, is that many of them either look like a business or would be properly located in the state. And, and that would, that would probably be true. Now, it may also be if business leaders and business founders ask the same question, it may be that some of them would actually choose a nonprofit, not a business.

Fascinating. You're right. Yeah.

I'm not as, I'm, I don't want to assume that a nonprofit, generosity driven structure is somehow less than. It's, it's kind corresponding business or state structures. Again, I would encourage us all to think what does the Quest require? And then let that, let that an, let that question drive our, our structural answers of is this a business, is this a business model where value of exchange is the primary? Is is this actually, does this live in a state structure, where a tax is the primary, is the? Or should this live in a nonprofit structure where generosity is a Driver? And I, I think they're all up for grabs. But so I do think that probably there are a number of services, if you will, that where the nonprofit is, is, not the best model for delivery. But I don't know if. I would go all in to suggest that the nonprofit is somehow intrinsically not capable of it, of certain delivery

Okay. Okay.

its own. I mean, I understand the trends, but as a business model, as a way to drive resourcing for a quest. It's not intuitive to me that a nonprofit is somehow like less capable than it used to be. I think it's probably been misused relative to the other options.

I have a prediction for you. Within the next two years, you are running for city council

Oh boy.

and then within the next seven years you're starting a B Corp.

How close am I?

You are, I, I would bet I would take the bet on the second. I don't, don't bet on the first

You love Beaver though, like you're pretty much already on city council.

I love it so much, but I don't, that's not the, that's not the container for my influence, I don't

Okay. Okay. Okay. Are you gonna work at the community pool instead?

Yeah, if, if, if it ever gets built, if,

The container for your influence is a pool.

You know, I, I have to, I have got one life to live Hillary, and I don't know.

Okay. Okay, so that was observation one. Observation two. Philanthropy is officially disorganized and may result in disorganized players. Both philanthropists and recipients of philanthropy are equally disorganized. What do you think the impact might be coming up here?

Yes. Well, I, I 100% believe that this, this particular, this observation is true.

Okay.

so I, yes. This observation is absolutely true. I'm up for disruption. And the reason I'm up for disruption is because I actually think that, that this sector, the gift sector, actually be the place where we experience the most unpredictability, the most explosion of, of possibility and imagination. That's, you don't get that from the market. You don't want that from the market. know what the prices are and what their is. You definitely don't want that from the state. And, we're in a living in a time where we're getting that from the state.

Mm-hmm.

don't want that from the state, but from the social sector, from the gift economy, you want that, you want like an explosion of the, the, the unpredictable, the unimaginable, et cetera. So I agree that very much that philanthropy is disorganized, and I think that there's fundamentally the core, there is two things going on. One, there's an identity kind of crisis, which is like, should philanthropy operate? Like an extension of the state or should, should we, like we, we are obsessed with looking to the market for business practices, like, should we be that? And so on one hand you have like this contending identity and then, and then also you have the gift itself, which I know is really abstract. But you have this desire to do something like people, humans want to be compelled to do something beyond the predictable, and the like, I think that that's like causing disruption here as well, where you've you also have a, the next generations some way. I'm, I'm very hopeful because they have this desire to kinda like, reclaim the, the wildness of the gift. they don't want to, they don't wanna follow suit, they don't wanna follow big philanthropy and how they give, so I, I do think that there's like a, I do think philanthropy is disorganized. I'm actually, I'm actually excited about that. 'cause I think it's a, I think it's actually a reorienting moment for philanthropy to reclaim that, which is most elemental about it. which is the question essentially like, Hey, where do I, actually release control so that something can occur?

Does that mean that social entrepreneurs need to be nimble and flexible to be able to scale up and down depending on their disorganized access to wealth?

Yes, Uhhuh? Yeah.

think part of this is like, not the nonprofit leader has to actually be up for the volatility, which is Whew. Is that, that's like a, that's a skill that we have not developed as a

Which it, yeah, it's a skill that doesn't often work in the non, I'm, I'm even wondering how a nonprofit would be able to function without predictability. But that brings us to my third observation about mutual aid. I believe that mutual aid is on the rise. And so I'm wondering what you think about mutual aid being on the rise. Are you seeing this too? What can we learn from mutual aid? What should we be learning?

100%. I see this, absolutely. I think mutual aid increases exponentially. The more proximate one is to the need. So I, and I think that this is like, celebrate every moment. very like local level where because someone is proximate to something, mutual aid actually increases. And the impact of that mutual aid is exponential. It's not just additive. And so I do see this, and I think it'd be very interesting, and I, I think this is like what you're addressing here is the v the very earliest stages of what's possible

Mm-hmm.

How would a social sector operate if we adopted and we're all in on the, gift. wildness of the gift we were designing not for predictable revenue, but we were designing for unpredictable gifts. And in do, in order to do so, we also had to develop the, the skillset of leaning on others IE and giving to others IE developing forms of mutual aid that kind of evened out the volatility. And so you can imagine for an example, like, you know, many, many, many, many nonprofits cannot afford health insurance to provide health insurance for, for their, so there's an opportunity here to think about from a mutual aid lens, how do we actually think about increasing or rising the floor, raising the floor of, of the sector or of an organization? Through creative ways to come to one another's aid. The fact that like nonprofits don't come together like five nonprofits with 10 people each, don't come together to provide a health insurance plan for 50 people, which is about where you need the, the number of employees you need, is beyond me. Right. There's this, this this seems like kind of

Yeah. We're just now starting to share buildings like

Right, right. Yeah, exactly. So, I mean, I mutual aid. I love this observation and there's, there's so much creativity or imagination that could be applied here. Moving forward now.

Hmm. So one of the things that I'm imagining you doing in your new job is helping investors pick their investments, helping them create their strategy for who they pick. And I have this secret wish that we could give investors like a laminated identification card. Like when you go snorkeling and you wanna see the fish and you wanna like point to them under the water, they, there would be a laminated ID card for the kind of entrepreneur that you could spot in a room that is the type of entrepreneur you wanna make a bet on as if they could be spotted. And so I made this list, this quirky list of 10 characteristics of leaders that I think will carry us through the next era that I wanna talk to you about. Because it's my attempt at making like an ID card that someone could take with them to a pitch competition or conference and, and be like, okay, I am looking for these qualities. Do you have the list handy?

I Sure do. I have it in front of me.

Okay. If you could put this list in order of importance, what would be the top characteristic for you?

Okay, so there my top three I think would be, they know their end game and I would pair that with another one on the list, which is they're making big promises. So in policy circles, hear about the Overton window, the framework of shifting the Overton window. And I would encourage everyone to check out. What that means is basically the question of what do we want to be sensible in our culture that today is unthinkable? And how do we move the over to window from today unthinkable to tomorrow's sensible commonplace in, perhaps if appropriate, even policy. And that is huge thinking for a, for an entrepreneur to be able to articulate the future state when the Overton window has been shifted the unthinkable to the sensible. When that, that is a, that, that's a remarkable trait in my mind.

Yep.

And so that's number one. two is a spirit behind the very last attribute on this list, which is, they embody paradox. I, I love paradox. I think that there's two things that come to mind. One is my, I I imagine this person having, and this is very similar where they are they're tuned into the non-obvious. So they're looking for paths to that end game that are non-obvious to the majority of the world, certainly the majority of best practices or other things. that, that likely means that they are fully schooled in that which has been done before. Four which is important. You, one of the other traits that you have here is that their understanding of the problem is robust. I think that's a prerequisite to being able to, to intuit. Identify the non-obvious solution or the non-obvious path gets one from unthinkable to sensible. And so there's a paradox there, usually in the sense that they're willing to, they're willing to kind of walk through the uncertain, the ambiguous, the, like I said, the non-obvious path. The, the thing that's like everyone else is telling you, Hey, that doesn't, that doesn't seem right. And, and there's something about the leader that says, nah, this is the way, or I have a nudge and I'm gonna go that direction,

And so, most, most leaders are thinking, and sometimes this is correct, but most leaders are thinking like, what's the most efficient way from point A to point B? And sometimes that works. Sometimes there's a moonshot. Kind of that works in that way. Some, sometimes entrepreneurs also are obsessed with the velocity versus the trajectory, so they don't even, they don't even know what they're looking to get to. They just wanna go fast. And I think what you, I think what this attribute is looking at is saying like, what are the non-obvious lily pads that you have to jump from, from one lily pad to another? And every time you jump a lily pad, you're, you're discovering something, something is emerging as to which next lily pad you should take. And if you were to, if you were to trace over a 10 year period, the lily pads a founder took, that that embodying paradox, that operate in a way that boards would be mad at them, et cetera, you would probably, at every moment of decision, there would be a sense of. non-obvious that the next lily pad is non-obvious. in hindsight, if you were to map it over a 10 year period from the 50,000 foot view, would say, well, wow, was, that was a beautiful path to the Overton window. That was, those are those that was, that was the, you might not say the right way, 'cause there might've been multiple ways, but that was a highly effective way to get from where we were to where we are now. And so I think that's number two is that, that idea, and then number three

You've already said like five things. You're only you're

just, I'm just driving it I guess one more, which is really just that like they are they're, yeah, I, they're, they're not married to the thing. We already talked about that. They do what the Quest requires and so. That goes for the, they're not that, that, that may be that they're not married to the nonprofit structure, but that also means that they're not married to, you know, the standard annual giving approach to fundraising, you know, indexes on certain values versus others and things like, just gonna, yeah, they're, everything's a whiteboard.

Mm. So let's let's see what you would coach an investor to be looking for if you were with them at a pitch event. If you were with your group of investors, you've been coaching them for a while, you're like, okay, I'm gonna put you in front of some leaders, some entrepreneurs. If you could coach them on what to look for in a leader within the first five minutes of meeting those leaders, what would you tell them to look for?

Yeah, right off the bat I'd be looking for imagination. And what I mean by imagination is are they asking of possibility versus feasibility or possibility versus constraint? And I'm taking bets on imagination. So that's one. and then two is two is and there I have three. Two is, is there a risk forward? Is there a willing to risk to re risk? In this individual, and the reason for that is because we've, I know you and I have both seen organizations that, and leaders who they had an aim and along the way I. Along the way when they made a poor, and we all do, right? We all make these wrong, these wrong decisions. The risk was too great to course correct. And next thing you know, you built an organization that is not doing what you said you wanted to do. And I think the re risk is such trait for the leader to be able to say, Nope, we are not achieving what we wanted to achieve. are willing to risk now have built. And, and I remember, I actually remember you, you used to, I don't know if you still do, but you had this, you had this amazing, phrase, which was like, we have to be willing to murder our darlings.

That's it.

Okay. So. I also wanna hear you talk about a leader that you might be working with that you think embodies the kind of characteristics we need for the King Tide era.

Great question. So one founder that, I I would point to is a guy named Jared Walker. He leads an organization called Dollar For and a Dollar For They're in the business of debt forgiveness. So there's a few attributes of Jared that I would really, really point to is, is that it was actually out of a very personal lament that he founded Dollar For. So he himself and his family have a, a personal story of the crushing medical debt. And and so out of this lament was the the conviction really the conviction that led Jared to, to found Dollar For.

I think that that's actually a really important trait of the leader that I'm interested in working with is the, leader that is operating out of their own very personal proximity and therefore in corresponding restlessness um, out of their own experience or observation, et cetera. Second Jared is back to our lily pad conversation. essentially started to work with. Families with medical debt to essentially in Obamacare in the ACA, there are forgiveness guidelines that every hospital in the United States actually has to follow, but most hospitals do not lead with that. It's not in their best interest too, their financial best interest too. and so dollar four is essentially helping families navigate a regulation that already exists that is in. And and so what happened was was that Jared, this is one of the lily pads, he discovered that this was a possibility and he wanted to help other families discover this as a possibility. So, you know what he did? He started a TikTok and his TikTok video was like, Hey, this is what it is, and if you want help, I'm happy to help. Next thing you know. It, I mean, it explodes, it explodes, the need rises to the very top. And Jared's sitting there with, whoa, well that was one big lily pad leap. I put a TikTok out in the world action begets action. And oh my gosh, look what happened. It forced and he was paying attention. It necessitated an answer to the next lily pad, which was, okay, I have to have a process for supporting families through this, through this debt forgiveness process with their individual hospital. Okay. So that was the first kind of like, there, there was a series of lily pads that like boom, explodes into what is now dollar four's thing a program model. And they're, probably over the a hundred million dollar mark by now in terms of the the medical debt that they have for have gotten forgiven. And now they're aiming at the next thing on the Overton window, which is what legislation can force hospitals to actually lead with this regulation instead of bury it and force the consumer to have to know about it, to take advantage of it, which most people don't know. so how does that actually, how might that move the, the, the Overton window from. Medical debt is a common experience to medical debt is a rare experience. so this is another thing where it's like his imagination is, is sky high. His approach is, is lily pad jumps from, from one lily pad to another. He didn't just just become a, lobbyist. He, he jumped lily pads on the way there. And this is birthed out of a, a personal lament of his own experience.

I am wondering though, the. The criticism of that would come from a leader who has an established organization that is not in startup mode, who can't be so nimble to go from one approach to solving the problem, to another approach, to another approach. Like now we're gonna do TikTok video, now we're gonna be policy advocates. And, you're asking them to pivot so frequently, that just isn't in anyone's rule book.

That's right. Yeah. And I, and I have a lot of compassion for that. And what do you exist to do? So, I mean, there's a little bit of like, Hey, if you're serious about solving the problem, get over it. that's easy. I know that's easy to say on a podcast, but I've actually been there though too, where I also have had to murder my darlings in order to move, move something forward that I believe should exist in the world. So I think that if you're, if you're leading a, a, a rescue mission, it's been around for 150 years and you're like, well, we have X number of people that rely on this meal every single night, and this is our program model and et cetera. Okay, I get that. And what is your quest? And, your quest may be to serve a meal every night, in which case, great.

Your quest is solving homelessness, you would, you would be pivoting and lily pad bouncing. Yeah, because it strikes me that your, your example with Jared, it, all of those pivots that he made were all in service of the singular solution to alleviate. Singular end game. All of those things were a, a version of, of solving that problem. They weren't solving different problems. So you, so you, you, you could come back and say that actually that's not mission creep. We're just volleying the way that we work on it. Hmm. W were you gonna say something too about how this relates to philanthropists?

Yes. One of the things I would pull out is the question of timeline so think that we're obsessed with in the social sector with impact and impact. Impact is fundamentally like if you were to look, if you were to talk to a physicist that the, the equation of impact is force over time. way you increase impact is increase force, decrease time, well in any other, in any other domain of our human existence that is violent and no one wants it, right. We've seen Armageddon, right? I've seen the, literally the movie Deep Impact was about end, the end of the earth, right?

I, I think that there's something embedded in how we talk about the word impact to suggest that decrease of time, increase of force is the way we get things done.

Interesting. Yeah.

I wanna push significantly back on that because that encourages and incentivizes a certain way of building that I think is fairly devastating to deep, deeply rooted solutions being solved. For long time periods. And so I, I want to encourage philanthropists and the, and some of the work we do at Praxis is thinking about is long-term influence over short-term impact and how do we actually give and design our giving in such a way that is designed for influencing the trajectory of an issue some immediate impact on an issue, which almost always has a corresponding rate of decay.

Yeah.

And, and, and we don't want that, we want enduring long-term reversal of things gone wrong. And I think philanthropists have to have to lead the way in that they have to, they have to be in long-term time horizons in order to make that that true. And nonprofit leaders will participate I believe that nonprofit leaders are mostly more aware of the long-term nature of these problems and than, than philanthropists are. And so if they can come together on what the proper timelines are, I think more enduring solutions can be brought to the table.

I love that. Influence over impact. So when they're vetting a deal, are you teaching them to ask questions about something that explains the influence goals versus the impact goals? Would it just simply be, what influence do you hope to make on this problem versus how are you going to definitively solve the problem? Does it give leaders an out I don't know. I kind of like impact better when it comes to solving a problem versus influencing it. It's a lighter touch it seems.

Yeah. There's a, there's a connotation of the word influence that is soft, which is unfortunate actually because there are influences in our. the history of the world that we're still feeling a millennial, you know, I, but I understand your point. The question I would probably ask is I'd think about system change. So if I were a philanthropist, thinking about long term, I would ask like, how does the system look different in a decade or in 20 years because you existed. a lot of, a lot of nonprofits, I don't know if could answer that question wonderfully right now. But that's a wonderful forcing mechanism for a really great conversation. And I think every, I think every nonprofit leader should be able to answer that question.

The King tide era for the social sector is the confluence of political, economic, and environmental pressures that have the power to erase or reconfigure us. King. Tides erase sand dunes. They flood the shoreline, but they also offer a sort of flush for the shallow waters or habitats along the shores. They can wash away, accumulated waste and pollutants, and refresh the oxygen levels in the water. Incoming sea water captures nutrients and organic matter from the ocean and deeper channels and distributes them across the vegetation near shore. So the charge here is to be an organization that is refreshed or reconfigured by these times rather than erased to have our chemistry reorganized. Which is different from making small pivots in our programming or operations to be more resilient. We're talking about asking bigger questions like, is a nonprofit the best model for service delivery for us in the years to come? Or how do we harness the resurgence of mutual aid or simply, what is our next lily pad?

Tailwinds is a production of Flying Whale Strategies, a consulting firm that is equipping teams to solve impossible problems. A special thank you to Dan Reed for sharing his experience with us. Dan, we did a good job. And this is the longest episode I've published yet. If you'd like to learn more about Dan's work at Praxis, please visit praxis.co. If you'd like to learn more about dollar four, please visit dollarfopr.org. If you'd like to learn more about Flying Whale Strategies, please visit our website at flyingwhalestrategies.com. Thanks for listening.