Team Up on the Tide— Moving from Service to Collaboration with Diverse Entrepreneurs

By Skoden Ventures, via Medium
September 18, 2023

With Skoden Ventures, my work is primarily two-fold. I’m learning about the age-old organization and system of the finance world and its gatekeeping mechanisms while strategizing a new way forward. I believe collaborating with other luminaries who are defying the odds with their work is vital, ultimately leading to higher chances of success. I was inspired to write this article and highlight some of the extensive conversations I had with fellow friends and funders in this space: Maacah Davis and Cindy Willard. We discovered that we are the rising tide: more people than ever are looking for change, and we can all succeed more with a new approach. — Kelly Holmes, Founding Partner

• • •

Let’s be real: diverse entrepreneurs have not been “underserved.” Service is the wrong word. And I know I’m not the only one who feels this way. I recently visited with my friends Maacah Davis and Cindy Willard to discuss how venture capital can better collaborate with Indigenous, queer, Black, Brown, and women founders.

Because we’ve been here, we’ve been succeeding, and our tide has long since risen beyond the relevance of a model that seeks to maintain those who serve and those who are served. In fact, I would argue that service was never relevant. It complicates simple facts in order to keep the halls of power tidy. What are these simple facts? Our success is already here. We don’t need a pat on the back. We don’t need charity. Diverse entrepreneurs grow more businesses, realize higher returns, and account for $10 trillion of missed potential wealth.

That’s why we need to stop thinking about deploying capital into historically excluded communities as a service and start thinking about it as a collaboration. Investors and entrepreneurs should be on the same team — one that recognizes that the only path for a sustainable economic future is one that taps into the immense value potential of historically overlooked entrepreneurs. When investors see diverse entrepreneurs as equal partners, we all get to learn from each other and help each other add value in ways that also help the people we care about and leave strong legacies for the future.


Investors and entrepreneurs should be on the same team — one that recognizes that the only path for a sustainable economic future is one that taps into the immense value potential of historically overlooked entrepreneurs.


I wanted to know: how can we unify our strategies? How can we all work together to shift the direction of capitalism so that historically excluded entrepreneurs are not categorized as needing “service” but are considered for who they are: extraordinary value creators. (Need a data refresh? Check out “The Overlooked $10 Trillion Opportunity”). We know plenty of extraordinary value creators who are BIPOC entrepreneurs, and we know plenty of extraordinary value creators who are funders. So how can we all be on the same team? How can we start pooling our wins?

I consider both Maacah and Cindy to be visionary leaders of a regenerative, sustainable economic future, and I am so excited to share what I learned about how we can make sure that we — as investors — don’t miss out on the rising tides of opportunity.

• • •

Maacah Davis — as a successful creative entrepreneur, business strategy consultant, and the grantmaker founder of The Garden Grant, an “international arts grant” that funds “experimental projects by diverse, multidisciplinary creatives” — has a unique perspective on the intersection of entrepreneurship and fundraising. After spending her childhood between Nigeria and Ghana, Maacah first rose to prominence as the 19 year old founder and publisher of fashion magazine belladonna in Birmingham, Alabama. Not only was belladonna Birmingham’s first high fashion publication, but it also emerged in 2014 as the first “Black woman-owned print fashion publication in US markets in years.” Since then, Maacah has made impressive waves: she was an Aspen Ideas Festival Fellow and TEDx speaker.


Maacah Davis


I always love catching up with Maacah because she lives what she talks. She learned from her experiences seeking funders for belladonna and didn’t shirk from the systemic issues of venture capital. Instead, she sought to fix them. First, she founded Maacah Media, an “ethical media company that facilitates opportunities for marginalized creatives and asks critical questions about accessibility and representation in practice, not just in theory.” Out of this grew The Garden Grant, where Maacah directly challenges traditional grantmaking in order not only to connect historically excluded creatives with financial support but also to “educate people on how to be more informed and more effective philanthropists” and “inspire veteran philanthropists to critically re-examine, and potentially change, some of their grant-making practices.” She must be doing something right because The Garden Grant has won support from heavy hitters like the Ford Foundation.

So how does Maacah apply her values in practice? First, she practices radical transparency. She interacts with the world the way she wishes it interacted with her: “clarity, honesty, transparency, saying exactly what I mean, doing exactly what I say I will do, and if I can’t do something, I will be upfront about my bandwidth and my limits.” This approach helps her build trust, which she believes is rooted in empathy. She strongly resists the idea that funders and founders have a “when I say jump, you ask how high” relationships. She respects the experience of people she works with because they have scaled their success to get into the conversation in the first place. Too many funders, she feels, see founders as cogs. In their pursuit of financial return, these funders reduce people to “what can they produce for you instead of who they are.” That “who they are” means how they live and impact their community — all the other forms of return beyond hyper-capitalist accumulation.

Too many funders, she feels, see founders as cogs. In their pursuit of financial return, these funders reduce people to “what can they produce for you instead of who they are.” That “who they are” means how they live and impact their community — all the other forms of return beyond hyper-capitalist accumulation.

We discussed some of the biggest realizations we’ve had over the years, like that “representation” in the world of venture capitalism is not enough. We’ve both met people over the years who claim to share our struggles and concerns because we both “represent” some identity category, but we sometimes discover that identity is something people can put on and take off as it helps them. So who is this identity for? Is it for your own gain? Or is it an authentic connection to a community you care about? Maacah tries not to waste her energy playing this game because she believes this “crabs in a barrel” approach suggests a lack of trust and shared power with others.

One of the things I love most about Maacah’s approach is that her values directly connect to her work. For example, I asked about her due diligence process with The Garden Grant. She had two very interesting answers. First, she reaches out to the community the entrepreneur is rooted in to see what kind of impact their business has already been having. “In every community, there might be an official mayor or leader, but there’s also the real mayor,” Maacah says. “Usually someone’s aunty or grandma who’s lived there forever and makes the best lunches. She’s the one everyone is campaigning to get on their side, and she can tell you who’s doing the work and who’s just getting the money.”

Second, she investigates the team the entrepreneur works with. For bigger teams, this means asking questions not only of those who have access to the founder — and the other leaders at the “top of the food chain” — but asking who don’t have this access. It means asking about maternity leave and asking “what does the lowest paid person at your company make?” Those answers, Maacah says, are very revealing about the potential of a company’s successful impact across all five forms of capital. “Taking care of people first is profitable,” Maach said. “It’s cheaper to retain a person than to hire one, so why would you treat someone poorly and waste your resources?” If an entrepreneur talks a good game about equity but can’t even treat the people working with them well — are they going to treat investors well when they are on the same team? On the flipside, if investors don’t understand why it’s important for an entrepreneur to pay their teams living wages — if investors don’t realize that people power all this value creation — they’re not someone the entrepreneur should work with because their values are too misaligned.

If there’s one thing that Maacah hopes funders realize when they’re trying to diversify and integrate historically excluded entrepreneurs, it’s that we don’t all share the same value system. We all need to reflect on where we come from and check ourselves: are we bringing hyper-individualist mindsets to community-minded interactions? I love this because it echoes our core values at Skoden: humility, respect, reciprocity, generosity, kinship.



I found myself nodding vigorously when Maacah said that much of what we call “philanthropy” should actually be an ethical baseline, not something we cheer ourselves for practicing. If we adapted this mindset, we would see less alienating practices, like requiring everyone to be a 501c3 or the common philanthropic model of demanding applicants re-traumatize themselves by weaving their most harrowing narratives of pain and gloom — all so the philanthropists can really feel like they’re “making a difference.” This is not only strange, Maacah says, it’s a waste of everyone’s time. What is the point of giving money if it’s not creating long term value?

So Maacah calls for all funders to be better at communicating capacity and what they want to see from founders. “Create better systems and processes,” Maacah says. We agreed that we shouldn’t ask businesses “What would you do with $10 million dollars?” Instead, we need to ask businesses what’s stunting their growth, what are problems not allowing the business to grow. Because these are the questions of teammates, not benefactors — and that’s the path to creating real long term value.

• • •

This notion of investing to work with founders to create long term value — instead of investing to tickle some short-term psychological need to feel benevolent — was also at the core of my conversation with Cindy Willard.

Cindy has been an innovator in the field of impact investing for over 20 years. Through her work with numerous organizations and foundations, she has helped challenge tired thinking about philanthropy and build new paradigms centered around “advancing positive social change through leading high-impact programs and integrated capital models.” Her current roles include serving as the Director of Capital Activation at Impact Charitable and Director of Integrated Capital at the Kenneth King Foundation. Between her advising, consulting, and directorial work, Cindy has been responsible for steering billions of dollars in impact funding to deserving entrepreneurs. She is in this for the long haul, and she is passionate about realistic returns on investment that prioritize values and create “more equitable communities through listening and solidarity.”


Cindy Willard


For Cindy, her journey started with philanthropy, but she realized that a model relying solely on one tool — grants — was ineffective for the large and interconnected problems she was passionate about solving. So she learned more about impact investing and integrated capital, which she defines as “a range of different ways to move money into places that haven’t had as much so that those communities can realize their full potential.” Her hope is that these practices will grow new models of moving not just financial capital but all forms of capital that create long term value.

In this mission, every day for Cindy is different, and she pointed out something that really resonated with me: relationships are key. Just as Maacah was talking about doing due diligence with entrepreneurs by talking to the people in their companies who have the least access to power, Cindy made me realize that we can only do as much good as our weakest relationships. Not having a mindset of service extends to social capital: we need to be generous with our connections and communities and practice radical inclusivity if we want to activate the potential of diverse entrepreneurs. As Cindy put it — based on a quote she heard at a conference for entrepreneurs in Minnesota: “network is net worth.”

These generous conversations Cindy has leads to the complicated work of building the actual financial products. She explains it as taking what we know about the systems we have today and seeing how we can change that to get a different outcome. This involves reconfiguring everything from the bottom up in building systems: how to set up funds, what kinds of governance structures to use, who gets to decide who gets what money. It’s important to Cindy to start with the problems, not the solutions. In other words, it’s not about deciding to build a certain kind of loan then looking for entrepreneurs to shoehorn into that loan. Instead, impact investors have to figure out what entrepreneurs need and create products to meet those needs. “If we keep doing the same things, we’re going to get the same result,” Cindy says. “And I am not interested in the same result.”

What are those “same things?” Cindy says that it starts by concentrating too much on just financial return. Instead, we need to ask: how do we create wellbeing? For the people: entrepreneurs, investors, communities. “We’ve ended up in a really dysfunctional place because of how we think about what we used to call externalities,” Cindy says. “That means our overall natural environment, our supply chains, all the pieces we need to incorporate back into the conversation.” She also pointed out that we can stop thinking about the impact our money has once we spend it and it’s gone, but it doesn’t stop that money from rippling. In fact, all of the capital we deploy has an impact: human, cultural, social, natural, and financial.


Network is net worth


One interesting turn this conversation about impact had was about the nature of help itself. Cindy agrees with me that grants and philanthropy are a faulty system. “Many grants are based on power imbalances,” Cindy says. “People have resources, and they’ll give them to you, but there are all these strings attached, and they still get to be in charge.” But Cindy argues that grants can be helpful as a pathway to investment, and generosity can inspire further generosity. What’s critical is that this is all done in partnership: an opportunity to pass along instead of a handing out. For Cindy, it’s not about “help” — it’s about a circle of support. I love her idea that support creates support because it resonates with what we believe about the relationships investors should have with founders: equal team partners.

Cindy’s due diligence processes to find team partner recipients of grants and entrepreneur partners is similar to Maacah’s in that it’s all about analyzing and creating relationships. Just as Maacah goes out into an entrepreneur’s community to better understand their current impact, Cindy attempts to create communities that form systems of support. So it’s not just about connecting entrepreneurs with funders — it’s also about connecting them with people doing similar or complementary work. All together, the end goal is shared prosperity. What’s the best way for this core creative idea to spark longterm value for everyone? What strikes me about Cindy’s thinking here is that it aligns with what I’ve seen as a diverse creative entrepreneur. We have been shut out of these hyper-individualistic systems, and as a result we’ve created value in community — the surprise (that’s not a surprise at all!) is that our value is actually a lot more resilient and sustainable.

Speaking of sustainability, one big thing that inspires Cindy to continue the work she’s been doing is (just like us) the next generation of consumers. She’s excited by the questions they ask about products, about companies, about origin stories. I agree with Cindy that Gen Z is strongly voting with their dollars, and they’re showing that the future of value is a future of values. And part of those values is collaboration, pitching in together to have impact instead of separating the idea of making money from making a difference.

Cindy argues that grants can be helpful as a pathway to investment, and generosity can inspire further generosity. What’s critical is that this is all done in partnership: an opportunity to pass along instead of a handing out. For Cindy, it’s not about “help” — it’s about a circle of support.

After all this discussion of making a difference with impact investing, I was curious if Cindy would agree with Maacah that these answers are actually very simple — and if so, why do we complicate them so much? Cindy believes our overly financial complex system comes down to maintaining power. “If you want to keep control,” she says, “you want to be the only person who understands it, so everybody else has to come to you.” She also quoted Rodney Foxworth: “risk is code for bias.” I love this quote because I strongly agree: the idea of “risk” gives people an easy reason to dismiss diverse entrepreneurs. As Cindy pointed out, these biases result in people confusing their personal ideologies and experiences with universal ideologies and experiences. Maybe other cultures besides yours interact with money and share resources differently, Cindy points out. Even if their experiences have proven that their systems work, your lack of understanding translates to aversion, which translates to your perception that experimenting with these alternative systems is a “risk.”

I love this answer because it comes back to this vision I shared at the beginning: venture capital investors should not be serving, they should be adventuring. When we think of ourselves as “serving” others, it’s easy for us to think we know better, we are qualified to help them and qualified to tell them what to do. But the reality is that the strongest investor/entrepreneur relationship is about sharing risk together, recognizing that we can acknowledge the perspectives we don’t understand and intertwine them with ours to explore opportunities together.

• • •

What I found myself thinking after both my conversations with Maacah and Cindy is that we really do make things too complicated. We invent categories and words like philanthropy so we don’t have to say simpler, more uncomfortable words like power. But we are in a moment that demands we move beyond discomfort. In my last article, I said greed is out — resilience and collective empowerment is in. I think that’s true for service too. Service is out because service ultimately maintains the status quo. What’s been built is not working, and savvy investors realize that. They look around and wonder at the world they’ll leave for their grandchildren. They wonder about how they’ll be remembered. Their impact, their era. Shorterm generosity is all well and good, but long term value — that’s the stuff legacies are made of. At Skoden, we have been doing the work. We are ready with a model that thinks hard about the legacy of value because we live our values.



People who cling to a world where these successful entrepreneurs are “underserved” and try to right the historic injustices and exclusions through that lens of service are missing out — plain and simple. They’re missing out on the potential of investing just as much as the entrepreneurs are missing out on the value they could grow with these investment dollars.

Take philanthropy, for example. The philanthropic model is a tool invented by the robber barons of yesteryear designed to help them maintain their power and wealth. These days, philanthropy might make us feel a little less anxious about our impact on the world, but it’s not creating generational prosperity — not for the people it “serves” or for the people doing the serving. Philanthropy will never unseat the old forms of hyper-capitalism that are destroying our planet and are becoming insignificant to Gen Z — and we shouldn’t ask it to. We don’t ask a hammer to split a log.

In fact, I would argue that philanthropy is the empty calorie of the investment world. Does it make us feel happy for a little while, briefly confirm our desire to feel generous? Sure. But we’re hungry an hour later. Because in the philanthropist’s drive to always be the “helper,” they always have to hold a little back, they always have to refuse the possibility of a level playing field. As a result, the help doesn’t last, and — this is critical — they don’t help themselves.

We believe that venture capital is — potentially — a different story. Venture Capital is a model that was designed from the beginning to reward innovation, to celebrate risk, to do what’s right there in the word: take a chance and venture. It’s a Swiss army knife, a flexible system designed to mirror the innovativeness of the entrepreneurs it helps venture forth. Venture capitalist investors are not doling out charity — they are expedition partners, bringing their Swiss army knife along where it’s needed, joining a team with hard-working entrepreneurs to passionately and creatively generate new kinds of value for our world.

Unfortunately, these days, most venture capitalism has traded in this spirit of innovation for tired biases. Many venture capitalists are not familiar with the markets of BIPOC-led businesses, don’t review pitches proportionately, and overestimate the risk of these businesses. They are using one small tool on their Swiss army knife — maybe the can opener? But there’s still hope. The rest of the tool is still there.

We believe that venture capital is — potentially — a different story. Venture Capital is a model that was designed from the beginning to reward innovation, to celebrate risk, to do what’s right there in the word: take a chance and venture.

Here’s why we think venture capitalism has more potential than philanthropy: because it is designed toward collaboration, not service. Venture capital investment compels everyone involved to put some skin in the game and share some risk. And with risk comes reward: the potential to uplift not only founders of companies but also their investors and the communities we are all passionate about building together.

At Skoden, we are passionate about returns on investment and creating value that is not just financial. We are passionate that we need to build a better future for our communities: our neighbors, our grandchildren, everyone we care about who has been left out of the way things have been run into the ground and is ready to regenerate with resilience.

Alice and I talked about this future in our first thought leadership article for Skoden, and in our second thought leadership article, I talked about the impact model we developed with Lee Francis. That model is about recognizing that financial capital is not the only important kind of capital. At Skoden, we seek returns for five forms of capital: human, cultural, social, natural, and financial. These five forms work in harmony, and they result in places where we want to live — and build intergenerational prosperity. Doom is out — sustainable futures are in.

Like Maacah, we are rooted in radical transparency. Like Cindy, we believe in reciprocal generosity. Together, I see all of us as part of a growing movement. We know what went wrong, we know the problems with what’s landed us in this mess. The hyper-consumption, the short-sighted individualism. But more importantly, we have lived the alternative. We have succeeded on our own terms. We know what we need to build because we are already building it, and our movement is about coming together to build strength with people whose values align with ours. Because together, we don’t need service. Together, we are ready for the adventure.



Skoden Ventures invests in Indigenous, Black, Brown, and women founders building growth companies in entertainment, experiential tech, creative products, and services.

Find out more about our mission as well as how to pitch for investment at Have questions? Email us at

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