066: Sarah Howard - Wealthy In Community While Striving for Economic Equity

Sarah Howard: Thank you. Thanks for having me.

Jonathan DeYoe: So first, where do you call know, where are you connecting from now?

Sarah Howard: Yeah, so I am, uh, in my home in Oakland, California, which borders next to Berkeley, which is where I grew up.

Jonathan DeYoe: So you grew up in Berkeley. Great. What did you learn about? I know some of the background because the way I know Sarah really is her entire family babysat for my kids when they were younger. She didn’t. She was grown and gone by the time that happened, but all of her brothers and sisters babysat for my kids. So what did you learn about money and entrepreneurship growing up?

Sarah Howard: So I come from pretty entrepreneurial families on both sides in very different veins. So the first one is on my mom’s side of the family in farming. And I think most people wouldn’t think about farming as entrepreneurial, but of course it very much is. And I think one of the key aspects of the entrepreneurial, the entrepreneurialness of farming is the inconsistency of income and the need to balance through the ups and downs of managing finances. So that’s something that I sort of observed from kind of a mafar as a kid, is that it sort of has this unpredictable nature, and so you have to sort of plan for that. And then on the other side, my dad’s side of the family, uh, my grandfather was an entrepreneur in printing for a long time, and so he built a actually, his father was also in printing, and so he built a business working with his father at first, and then built his own, and then had that press in Tucson, Arizona, called Sundance press for many decades. And one of the key things I learned from him is the power of building something with people. So his employees, many of them were multidecade employees. And so there was a real sense of, how do you take care of the people who build your business with you? So I think those are the two legacy that I come entrepreneurial generations, I guess. And so that sort of infused my childhood understanding of entrepreneurship. And I think while it wasn’t something that was sort of an obvious path or necessarily talked about in a direct way, it was sort of something that I think I naturally gravitated towards was sort of forging my own path.

Jonathan DeYoe: What were some of the lessons, what did you take out of rather than the farming side? Because I think that gets into a lot of other issues that are not in our control, which is important to learn, obviously, but this small business side, what were some of the lessons you learned from, I guess, your grandfather and I guess maybe your father afterwards?

Sarah Howard: Yeah, so a few things from my grandfather in particular, and I get this from my dad as well. I think they’re very similar in this way. It’s very community oriented. So my grandfather was really well connected in the community and built a greater sense of community, and this is specifically in printing within his industry, built a sense of community. And so when he faced a devastating fire, pretty much destroyed his business, the community really rallied around him. And he had certain terms with people post that fire for years, and it was probably decades later that they’re like, we should probably reexamine the terms of our agreements based on, this is an exchange. This is the informal part of business, because it’s about taking care of each other when you need it. So he built a lot of those things because he had really shown up for the community, and they really showed up for him. So similarly, I think my dad really took on a community building legacy. And that is absolutely something that I put into practice in my work and just how I operate in the world. I think it’s probably one of my greatest resources or assets. And I’m sure we will get into the money side of the conversation later. But when I think about the ways in which I am wealthy, I am certainly wealthy in community.

Jonathan DeYoe: Were there any lessons that were taught but not learned, like anything, that they were like, this is really important. And you said, you know what, I’m just going to go my own way on this.

Sarah Howard: It’s a good question. I don’t know if anything’s really coming to mind. I think that I’ve definitely done things differently. It’s not the same at all, but there’s nothing that I can think of that was a specific, this is the direction to go. And I went a different way. I think I just naturally went my own way.

Jonathan DeYoe: That’s a sign of good parenting right there. You’re able to kind of go your own way and feel like you’re honoring the legacy at the same time. That’s beautiful. From where you sit today, what are some of the most important elements that build your money story? I mean, uh, entrepreneurship is one thing, and how do you earn a dollar is one thing, but where does your.

Sarah Howard: Money story come from in terms of management origin? Yeah, like how I understand it. Yeah, I think there’s a couple of different key influences in how I understand the story of money. I think the larger legacy. So I’ve spoken about my grandparents, so I think at that level, that looked like, I think more on the traditional, responsible kind of perspective on money. That’s sort of all the things we would expect from that generation. And this is the go to phrases around money. And my grandfather, the printer, is a big investor, so he would talk about it from that perspective. On the other side, it was, uh, the farming side, again, the boom and bust dynamic. So I think those are two stories that have informed my story of money. And then stepping down into my family and my parents, I’d say some of the stories from childhood would be one, resources are limited, and I think that has been something that’s a challenge for me at this stage. So coming from a large family, I have seven younger siblings. There was a lot. There just wasn’t a lot. And I think that is both a true statement and a not true statement. And of course, money has so many stories that are, uh, grounded in reality and so many that are grounded in perception or what we’ve made up. And so I think that story is both. And then I’d say environmentally, sort of the environment that I grew up in, being Berkeley, I’d say the story of money there is money is a little bit more suspicion of money and, uh, more critique, I’d say, because I think there’s, like, a cultural societal weariness of it that aligns with some of the more political side of the culture of Berkeley, which tends to be more activists. And so I think it would have a lot more anti capitalist perspective. Not that it’s the only one, but I think that sort of finds its way into the common conversation, maybe more than other places. And so I think that also kind of infused the story of money that I was exposed to. Yeah, I’d say those are my key influences.

Jonathan DeYoe: That last one is very interesting. I’m in Berkeley as well, and my kids are growing up here. And as I think your grandfather and father and mother are, I’m very capitalist. I believe in the system. I think it works. And there is that Berkeley sense that there’s something broken or not right about it. And so it stimulates lots of conversations, and we’re going to get to this money and meaning thing in a bit. Before we get there, though, in one of your email interactions, you said that you’re in the middle of lots of different projects, and these projects are sort of helping you explore your potential paths forward. So what are the projects you’re exploring? What are the projects that you’re part of right now?

Sarah Howard: Yeah, so you mentioned a few of them, but the one that is sort of top of mind for me right now is I’m working on a documentary that is telling the story of the island of Dominica in the Caribbean and their ambition to be the most climate resilient nation in the world. And that film’s coming out at the end of this month, and it actually has a financial narrative to it. So the vision of the island is this decade long plan for resilience and adaptation to the changing climate. And they have a very clear and compelling plan for doing that, and it needs to be capitalized. So I started out with this film being like, it’s good to raise awareness about what they’re doing, but I want to have a clear impact plan. I want to have a clear vision for what I want the film to do. And so I decided, why not have the vision be raising all the capital they need? So I decided to take on a small, not ambitious vision of moving $2.5 billion to the island of Dominica. So that is definitely influencing my own relationship to how I understand money and the way that it flows. And I’m like, why not? Why not? And, uh, it’s very much this act of, like, how does this actually all work? And what stories am I telling about how it wouldn’t work or would work? And this isn’t even really about me. This is about another project in an entire country being resourced to create this vision, but it definitely comes back to finance. And so it’s also taken me on this journey of understanding more our, uh, global financial system. And this film will launch a series of short films on small island developing states. And the next one that I want to do is on the island of Barbados, which is being led by Mia Motley, who is on a campaign to change global finance. So I’ll just get deeper into it. So it’s definitely been a really fun journey to learn more, and I’m deeply passionate about it. So that’s one. And then another one is that I’m doing programming and speaker relations for the global philanthropy forum. And that also, because I did a whole series of my podcasts on philanthropy, is very much a conversation about money. So, like I said, it’s sort of fighting its way.

Sarah Howard: Yeah, so we’re in the early stages of. The film isn’t launched yet. So I think that one hurdle is understanding the larger potential and impact of this one island being able to achieve true resilience. I believe this is the kind of plan that every country is going to need, because it’s a true whole of society, whole of government, fully aligned vision, which is a rare thing to find, that is completely generated and designed from within the island. So it is actually well adapted to what’s needed there, versus outside consultants that often can miss the mark in terms of what is actually going to work. And they’ve worked on this plan for the last five years because it seems so small. My strategy for extending that to the larger potential of this project is that I want to turn it into a case study that basically looks at how do you deploy capital, different types of capital, along a strategic plan? So what does it look like for philanthropy to fit in that plan and then hand off to private capital or hand off to large development loans? How do you capitalize across a whole decade long, full resilience build out? And that’s entirely possible. It’s really about ambition. It’s really about people getting aligned around that. And what I think is really compelling is if you have the ability to test out this concept, there’s so much learnings that can come from that. So that’s why I wanted to build a case study. It’s like, who can come around this to actually track what happens? How does this work, and how can that been a model or a blueprint for other countries or even cities or any levels of society that want to take on a similar resilience building plan?

Jonathan DeYoe: Yeah, in my head, there’s two things that are connecting. One of them is your grandfather’s lesson of community and how you’re sort of applying that on a global scale. I’m assuming the philanthropic capital comes from a country like the United States or Norway or developed nations towards underdeveloped nations or undeveloped nations. So when did social activism become such an important element for you, and does that come out of the Berkeley capitalism is bad, or when did that become such an important thing?

Sarah Howard: Yeah, I think that some of the early influences that have guided me on this path are one, certainly a culture in Berkeley, and I think one of the things that really is compelling about it is that people are really passionate. They really believe in something. They believe in their ability to impact change. I think that’s really important and has definitely influenced who I am. It doesn’t matter what it is or to what end. It’s this idea that it is possible and that we individually have both the capacity and often the responsibility to do so. So I think I take on that especially early on. And then the other thing that was an early influence was in college, I really considered more of an academic path, and I couldn’t shake this feeling that the ivory tower wasn’t the place to make change. And I kept trying to answer that question. I pretty much interrogated every professor that I had, and none of them could really tell me a reason that I could be able to do it from the ivory town. I was like, I cannot justify that path. It does not feel right to me. And so I was like, I’ve got to go do it in the field. I have to do know at the. And so, very quickly out of college, I did work in southern Sudan as it was becoming a nation, and then ended up doing a bunch of work in Central America. So I just sort of directly went into a path of being able to find out what is happening on the ground around the world in the ways that those challenges and opportunities and displays of resilience are similar, and then how to sort of galvanize that at a larger, uh, scale.

Jonathan DeYoe: The things you’re talking about are usually, I think, viewed from legal space or from, as nonprofit focused. You really want to make a difference internationally. You have an NGO, you really want to make a difference in development, develop philanthropy, you develop projects with a rotary, whatever the group is that’s trying to support that. You’ve said, and your generation, this may be a generational question, is kind of saying, no, this can be business objectives. We can have a business objective to change the world. Do you think it’s a unique to an age group? Because we used to start a business, hey, there’s a need for a thing, and we’re going to fill the need with a service or a product, and that’s the business that comes out of that. This is enormous need, like shoring up developing nations and New York and the, uh, west coast of California versus climate change. This is huge. So are there advantages tackling that with for profit instead of non profit? And then are there disadvantages?

Sarah Howard: Yeah. So one of the reasons that I find climate to be so compelling is that it is the true systems change issue. I think there have been really large, very important issues that don’t have the same level of cross cutting across everything that touches our lives the way that climate does, nor does it have the level of urgency. And to me, because I’m a natural systems thinker, it was just really sort of obvious that this is the thing. It will change everything, and, uh, it will change everything regardless of what we do, because it’s coming. And there’s also the opportunity of it that I think is, for me, the hopeful part, that I believe there’s a chance for us as a species, as a society, to reexamine the way we have done things up until now and see what could be better. That there is an opportunity for this system to be massively improved if we sort of come around it and actually have a united vision, which I do think is possible. It’s really hard. And that level of cooperation is something that has only been achieved in very few moments in history. But I do believe that this is one of them. We have that chance.

Jonathan DeYoe: Yeah, it’s required. I mean, this is one of those things where the changes have to come. But looking at your specific, the film project, how do you make that profitable for you as a small business person trying to grow a thing? M if it’s successful, you have massive impact. But how do you make that profitable for you so that you can one day retire or afford a family or take vacation? So to put this big vision of impact in your life, how does it help you define and create your own success?

Sarah Howard: Yeah, well, the very candid answer in this particular moment, I’m, um, kind of in a personal career transition and figuring out what’s going to be next. And I’ve got this large portfolio of work from which I could continue to develop or sort of pass on. And there’s definitely a key component around that is about financial sustainability for myself. And this particular film came about after I had sworn off doing film because it wasn’t working. And I was like, I don’t know how to continue doing this. I think it was working for a while, but, uh, it wasn’t also what I felt was having the level of impact that I wanted. So my solution was to not take any film projects that weren’t funded. And then that same week that I made this declaration to myself, this film came in funded, and I was like, okay, all right. It’s still not quite at a sustainable level yet, but it had trended in that direction. It’s like, okay, I should probably see what’s down this path. Not to mention, this is actually what I care about. So it was a convergence of things that are starting to answer that question for me, because it’s generally really hard in film. Film isn’t necessarily the most sustainable. There are good movements towards making it more sustainable for people, but as a business owner in this space, that’s been tricky because I am typically the contractor. So I’m hiring all kinds of people for my projects and I want them to get the sustainable pay that they deserve. But sometimes that does come at the sacrifice of my actual payout in a project. So making that all work is tricky.

Jonathan DeYoe: So I would say that exists in coffee shops, financial planning firms, technology firms. I think that the challenge of starting a thing and making it profitable while having expenses, including employees and other things, it’s one of the reasons I think that we have, and I should couch this, in the last 18 months, we’ve seen a pickup. But up until 18 months ago, the small business startups were dismal. They were in decline and had been in decline for two decades, but suddenly we had the pandemic and people had to figure out stuff on their own. So you have lots of small business starts, you have lots of things happening, but it comes with that risk. And I think it’s really important to recognize that. It’s easy to take the job at Google, it’s easy to take the job at Microsoft or at Chevron or pick your Fortune 500 company. It’s easy to do that. Really hard to build your own thing, regardless of what that thing is. And this I think gets to the heart, right, how we define our own success. Like you talk about impact and about this film, that was quite fun. It came down and you’re like, this is, by the way, it’s something I want to do. So there’s an impact you can have. It gives you joy to do the thing. The compensation may come third. What are the factors that we societally consider as factors of success? And then what are some of the factors that maybe we should in your generation or Gen Z is actually even more so pointing us in the direction? Maybe there’s these other things we should be thinking about.

Sarah Howard: I think a lot about how you define success. I think that’s been a personal journey. I think have been fortunate and have also worked very hard at ah, defining that for myself. And it’s allowed me to have a very rich life and a very rich career. And it has meant not having the same levels of traditional success financially. That hasn’t bothered me and I think it is because I’ve defined it differently for myself. And there’s levels of that are both smart and sort of, you can get into the details of it, but at a certain level you get to a certain point and the value, the impact, the meaning that comes from money really diminishes quickly, such as the downhill spiral really fast. And I never wanted that. So I was really cautious of it and at the same time really compelled by meaning. And that wasn’t something I defined at the beginning of my career. That’s an ongoing process, something that I’m continually working on. And I think that even right now that’s even more top of mind than a couple of years ago because they’re in a transition. And as I’ve thought about it for just myself, I’ve thought about it at a societal level. I think it is one of the things that is most important for us as a society to address because it intersects with some of the biggest challenges of our time, whether it be loneliness and depression, connection with other people, our actual whole extractive system of business, or even just the consumerist nature. These are all things that are tied to our sense of success and meaning and who we are. And the things that the stories we’ve been told that will make us feel better aren’t actually true. And so being able to define that for yourself or have an internal compass and guide for how you understand success is the key to living a happy life. It’s a tricky one because it’s hard. Takes work. You don’t just get just a land bam. You’re like, here’s the definition. Everything’s good. You actually have to work at it regularly.

Sarah Howard: Take on someone else’s definition of success, right? Like, oh, someone else figured it out. I’ll just do that, right.

Jonathan DeYoe: Without having to do any work myself. So it turns out you have to do the work, right? What do you think about the external versus internal? I think you mentioned, uh, the studies where people are successful, they feel successful and the money is a detraction from that feeling of success. And that’s that internal sense of success versus that external marker of success. So are there important external markers or should it all be internal. A degree, a salary level, wealth level, a ceoship of your company, starting your own business. These are external markers.

Sarah Howard: Yeah, I think that they can influence, because there also are markers of just recognition of the work you’ve done. So I think I don’t discredit them because having the ability to point towards this is the thing that I worked really hard to achieve is important because it does sort of circle back to your own internal motivations and definitions and the way you’ve set that path. So, for example, having the film, having a film out in the world is my ability to sort of show. This is what I’ve been working on for years. Films take a long time and there’s so much wrapped up in them, but having this thing that I can then share with others is a way of kind of bringing them into the path, too. It’s like, look, here’s the thing, and you can point to it. And that, uh, I think has ongoing feedback loops of satisfaction and meaning itself. And so there are other versions of that, whether it’s the degree or it’s like my friend who next week is having his invention put it up in the Smithsonian, those are things that really matter. So I don’t want to discredit those kinds of markers, but you can get them and have a complete feeling of emptiness. So it’s not a guarantee that it’s going to feel meaningful. It still links back to that internal, intrinsic sense of meaning in order to even get the value out of that. There’s plenty of people who’ve gotten all the accolades and do not have that sense of satisfaction because that wasn’t being driven internally from the beginning. So then they miss out, which is really too bad, to be honest.

Jonathan DeYoe: I love. It’s, uh, not external markers aren’t bad, but if they’re not built on the frame of internal, if you haven’t done the work of introspection first and built your external markers on top of what you actually want, then you get all these accolades and you’re like, I didn’t really want those things. And it’s just the feeling of emptiness is, I think, yeah, we see a.

Sarah Howard: Lot of that, uh, maybe even worse. It might actually make you feel worse because that’s the thing that’s supposed to make you feel better, and then it doesn’t. And then that feedback loop is actually stronger as well, which was, that’s a really hard cycle to get out of.

Jonathan DeYoe: And looking back, all this work I did to get this thing that I don’t really want what do I really want? I’m so far behind now you can start really judging in sort of this cycle of downward spiralness in your own life. So we swim in a very noisy, social media infested soup, right? Lots of different messages, signals about what matters. Could you just simplify it? I do this to everyone that comes on the show. Simplify it for us. What is one thing that somebody can do that’s going to lead to greater personal and financial success?

Sarah Howard: So I was at a dinner recently that was for people who are doing impactful work in climate, and it was during SF tech week. So it was a bit of like a countercultural thing. Like everyone is going around and sort of in a frenzy trying to figure out how to invest in AI, right? That’s what’s happening out in the world in chaos. And this friend of mine created this space that sort of was in the midst of the chaos. There’s also this conversation about people who want to have an impact on the world and have a vision that is grander than these sort of short term cycles of fads and crazes. And she asked a similar question. And like I said when we had our conversations about this podcast, I’ve been thinking a lot about money. And so my answer was that I think reflecting on our stories about money is really profound and can change not just ourselves, but the world that we live in. And if there was one story within the story of money that I think is a dominant story that I would love to see shifted, it’s the zero sum story to one of abundance and sustainability. And I think that’s entirely possible. That is what I believe is the hope of this moment as we face climate crisis, is that there’s the ability to shift that whole mindset. And that is not about a system of capitalism or not capitalism. It is not any of that. It is just the story of we either live in a zero sum world where you have to get all you can at the expense of someone else, or that there is enough and just enough for everyone. And how can we make sure everyone has enough? Because that’s possible.

Jonathan DeYoe: Lovely. And the flip side of the question is, what’s one thing that people might be doing that if they just stop doing it, it would lead to greater.

Sarah Howard: Personal financial success besides Doom scrolling.

Jonathan DeYoe: Uh, my favorite answer, actually, I’ll give.

Sarah Howard: Doom scrolling, but I want to give another answer. It probably goes back to our previous point around success is just taking on other people’s definitions of it. Because one thing you can do is just start with stopping to take anyone else’s definition, and that might not mean you’ve developed your own yet, because like we said, that is work, and that’s okay. But one thing to do is just stop taking other people’s, or at least notice, is this mine or is this someone else’s? Did I come up with this? And I think so many people are just asleep to that. And understandably. And that isn’t even a criticism. It’s more of an opportunity.

Jonathan DeYoe: I think it’s human nature. Direction is a vacuum. If you don’t have a direction, someone will give you a direction, and it’s best, just like you said, start by stopping, following somebody else’s direction. Figure out your own right. Start by stopping, and then figure out your own right. So, coming full circle back to personal, is there anything people don’t know about you, like you haven’t said on a podcast? You haven’t told people that you really want them to know about you?

Sarah Howard: This is a great question. So, one of the reasons that I agreed to come on this podcast is because I’ve found that when I go on podcasts, I learn a lot about myself. So they are always learning journeys for me. I’ve had really profound insights in the other ones that I’ve been on, and they’re entirely unexpected, but have really stuck with me because I’m just willing to show up and learn and be like, well, I’m open. I’m learning in this moment, too, so let’s see what happens. A lot of people probably know this, and this is connecting back to an earlier podcast episode that I was on. I am dyslexic, and it’s something that I didn’t really have a lot of connection to until I literally was on a podcast. And it came up and I had not thought about it in decades. It wasn’t something I was actively avoiding or incorporating. It was just sort of. That was part of me that was very far back in my history. And what I’ve found since realizing that is that it’s opened up a lot of greater personal understanding and ability to understand the world and other people more. And I think there’s a really cool moment happening and people understanding the types of neurodiversity that exist out there. And so I’ve, uh, been enjoying this journey, I guess, of learning my own and connecting with other people around it in this very organic sort of way that I’ve been very surprised by. It’s been great, and I didn’t expect it at all.

Jonathan DeYoe: Yeah, cool. If you could get a true answer to any one question, and you knew it would be the true answer, what would be the question?

Sarah Howard: This is just like general. Could be from, um, a person from.

Jonathan DeYoe: The universe, about your life, about when the water levels hit that 20ft above where they are now. It could be whatever you want. If you could get the answer to one question, what would that be? What would be the question? Because I can’t give you the answer, but I can help you focus on the question.

Sarah Howard: I can’t quite formulate the question, but what’s surfacing is something around conflict and the ways that we as humans engage in conflict. I feel like there’s so much there that can be avoided, and yet we find ourselves so often back in the same spirals and loops of conflict, even down to historically, we’re in repeating patterns around this. If the question was like, how do we get out of the loop? I guess that’s it.

Jonathan DeYoe: Well, this is one of the challenges, I think is. I think I know what you’re saying here, but, uh, one of the challenges, I don’t think we can do it. I don’t think we can do it collectively. I think each individual has to find a way to be less triggered, less reactive, more responsive, more thoughtful. And so I would say that one I know the answer to. It’s called meditation. It’s called mindfulness. That is certainly something that literally, scientifically reduces that. Reactivity, reduces that. But boom. Absolutely, I agree.

Sarah Howard: And I guess the question is how that happens, really on the large scale, and if that’s possible, because I do believe it does happen individually and that does scale up. But is there a ceiling? And what does it look like if we’re actually seen at a larger scale?

Jonathan DeYoe: We need to, uh, somehow get meditation into all the schools and, um, then all of them, like globally. We can’t just do it here, we can’t just do it in the California. But that’s a whole different podcast, I want to say. How do people connect with you? How do they find you?

Jonathan DeYoe: Sarah, thank you for coming on the Mindful Money podcast.

Sarah Howard: Thanks for having me.