Funding Bravely

"Some of us are funding to win. Some of us are funding to survive another day."

$120 trillion is transferring to a new generation of capital holders over the next two decades. A disproportionate share of it is going to land with women. Jessyca has a name for what's coming: matrilineal money.

Women hold and move capital differently. As a percentage of their wealth, they move more of it. They are more likely to move it in collaboration with others. They are more likely to see philanthropy as strategy, not side project, when the sector stops treating it that way.

Layer that generational shift onto the $330 billion already sitting in donor-advised funds, and the question this episode holds is not whether we're in an inflection point. It's whether we have the imagination to meet one.

What do those dollars actually owe the communities whose labor and creativity generated that wealth in the first place?

In Episode 4 of the Funding Bravely DAF mini-series, host Marvin Smith sits down with Jessyca Dudley, founder and CEO of Bold Ventures, to turn the DAF conversation toward repair, and to ask what the greatest wealth transfer in human history could actually become if all of those receiving it, and the communities they choose to move it toward, get to shape what comes next.

Jessyca spent a decade in public health in Chicago before she came to philanthropy, working close to communities to understand what they actually needed and designing interventions with them, not for them. That frame, close to community, upstream, preventive, is the one she brings to philanthropy today.

This conversation unpacks:

• Why philanthropy was never neutral, and the difference between the culture of philanthropy (reciprocity, mutual aid) and the business of philanthropy (Gilded Age origins, tax policy, extraction)
• Money stories, and why decisions made with unexamined ones drift from our values
• Why DAFs are a tool, not an ideology, and what we could actually build with $330B already committed to good
• Pooled DAFs, community-seeded decision-making, and the median $90K DAF holder as the real audience for creative deployment
• Why matrilineal money is a strategy, not a demographic observation
• Community foundations as modernized community chests, and the opportunity for donor organizing inside them
• The reframe: stop funding the immediate need, start funding the end of it

She doesn't argue from theory. She argues from practice, from the $60M+ she's helped clients move, and from the participatory models she's built with donors ready to seed decision-making to community. The great wealth transfer will happen either way. Whether it becomes a reparative moment or another cycle of concentration is the question this conversation refuses to let us dodge.

Magda Guillén Swanson helped build the architecture of DAFs from the inside at Vanguard Charitable, one of the country's largest sponsors. Now she's pointing out what the system still hasn't delivered.

And she's building Familia Fund to prove it can.

In this episode of Funding Bravely, host Marvin Smith sits down with Magda Guillen Swanson, general partner at Familia Fund and former head of innovation at Vanguard Charitable, to ground the structural critique of donor-advised funds in lived experience and clear-eyed possibility.

Magda traces her arc from a small rural town on the South Texas border, to the trading floors of Merrill Lynch in London and New York, to the design rooms of one of the largest DAF sponsors in the country. Along the way, she came to believe that financial instruments are infrastructure and that the people in every node of that infrastructure are shaped by what those instruments incentivize and what they don't.

This conversation unpacks:

Why the implicit bargain of DAFs -- public benefit in exchange for tax benefit --isn't complete until the money actually moves
What it actually looks like inside a major DAF sponsor when you try to bring creativity to a static instrument
The COVID moment when Vanguard Charitable's donors couldn't find frontline nonprofits and how Magda's team built a solution to address it
Why the next chapter of DAFs isn't grants, it's recyclable, community-sovereign capital
How Familia Fund is using a DAF-based fund to invest in underrepresented founders
The cost of being a "gate breaker" inside entrenched systems

Magda's line that stayed with me: "Patient capital with an impatient mindset is the most powerful mix of all."

This is a conversation about whether we have the imagination and the courage to make DAFs honor the bargain we already wrote into our tax code.

What if the conversation about donor-advised funds has been missing the point entirely?

Sarah Angello has spent two decades inside philanthropy. Early in her career, she partnered with a microfinance fund for women entrepreneurs in Uganda, learning what indefatigable courage looks like on the ground. From there, she went on to become a chief development officer in San Francisco and a software entrepreneur, before co-founding Daffodil to build what the next generation of giving actually requires.

She wants us to stop thinking about DAFs as transactions and start thinking about them as habits.

In Episode 2 of the Funding Bravely DAF mini-series, Sarah joins host Marvin Smith to open the season by lifting up what donor-advised funds genuinely make possible.

This conversation unpacks:

• Why the average DAF balance is around $90K, not millions, and why that changes everything about how we should design for these donors
• Why DAFs pay out at 20 to 25% on average while foundations pay out at 8% (including operating costs)
• What the next generation of donors actually wants, and why it isn't transactions
• The DoorDash test: why charitable giving should feel as engaged and visible as ordering groceries
• Why financial advisors who talk to clients about generosity have happier, stickier, longer relationships
• What courage looks like for a fundraiser, and why a workshop on NOs (as in, "no.") might be the best training of her career
• Why philanthropic technology has been an afterthought, and what it would take to design it on purpose

This isn't an anti-DAF conversation. It's making a case for what DAFs could become if we designed them for generosity instead of for tax windows.

Resources Mentioned: Daffodil — getdaffodil.com

Over the coming weeks of the DAF mini-series, hear from voices inside DAF sponsorship, on the frontlines of reparative philanthropy, and from a DAF holder who has been spending one down on purpose for sixteen years. Subscribe to Funding Bravely so you don't miss the rest of the arc.

🎙️ ABOUT THE PODCAST

Funding Bravely surfaces the unseen courage of leaders challenging power, moving money faster, and reshaping pathways to impact in partnership with communities. The DAF mini-series, DAFs at a Crossroads: Moving Money at the Speed of Need, asks what it would take to move the $330B+ already committed to good with the urgency this moment requires. Hosted by Marvin Smith.

Subscribe if you're ready to fund more bravely.

Three hundred and thirty billion dollars. Already called charitable. Tax deductions already claimed. Communities still waiting. This is the opening episode of Funding Bravely's first dedicated mini-series and it starts with a provocation most philanthropy conversations won't touch. Donor-advised funds weren't designed to move money to communities. They were designed to park it.

In this solo episode, Funding Bravely host Marvin Smith opens the DAF mini-series — DAFs at a Crossroads: Moving Money at the Speed of Need — by doing what the field rarely does: telling the origin story of donor-advised funds honestly.

It starts in Dallas, earlier in Marvin's career, doing fundraising work alongside a community foundation. On paper, the infrastructure was there - assets under management, donors in relationship, money already committed to charitable purposes. But what he kept running into was distance. A gap between where dollars sat and where organizations actually doing the work were. And an incentive structure quietly shaped by how many funds the foundation held, not how much they moved.

That experience and the structural question it raised is why this series exists.

This episode covers:

• What a donor-advised fund actually is and how to think about it clearly
• The history of DAFs: from community foundations in the 1930s to Fidelity's 1991 turning point
• Why the average DAF account holds around $90K and why this is a mainstream infrastructure problem, not just a billionaire one
• The origin story most people skip: DAFs were designed as tax optimization vehicles first. The philanthropic framing came later.
• There is no legal requirement that DAF assets ever leave the account
• Why the explosive growth of DAFs is a sign that wealth preservation dressed as generosity is working exactly as designed
• The five questions this series will carry and what it would take to answer them

Resource Mentioned: DAF Research Collaborative: Annual DAF Report 2025

🎙️ ABOUT THE PODCAST Funding Bravely surfaces the unseen courage of leaders challenging power, moving money faster, and reshaping pathways to impact in partnership with communities. The DAF mini-series — DAFs at a Crossroads: Moving Money at the Speed of Need — asks what it would take to move the $330B+ already committed to good with the urgency this moment requires. Hosted by Marvin Smith.

Subscribe if you're ready to fund more bravely.

Comment with what surprised you most about the origin story of DAFs. Share with someone who holds a DAF or advises someone who does.

93% of funders think they understand the challenges their grantees face.

Only 53% of nonprofits agree.

That 40% gap isn't just a number—it's an existential threat to the sector. And Dr. Elisha Smith Arrillaga has the data to prove it.

In this episode of Funding Bravely, host Marvin Smith sits down with Dr. Elisha Smith Arrillaga—Vice President of Research at Center for Effective Philanthropy—to talk about what happens when data meets courage.

Elisha's story begins in Mississippi. Her mom filed a lawsuit against the city for employment discrimination—and won. Those anti-discrimination laws are still in place today. Her dad worked at the Equal Employment Opportunities Commission in Birmingham during the civil rights era. Her grandmother was the first Black worker in a factory in a small Mississippi town.

"I stand on the shoulders of my parents and grandparents," Elisha says. "It's a privilege to do this work."

And she's doing it with urgency.

Because the data is screaming:

• 81% of nonprofits have experienced or anticipate increased demand for services
• 68% of nonprofits say the current context has negatively impacted their ability to do their work
• 61% of nonprofits face moderate to significant risk to their ability to continue operating

Meanwhile, funders think they understand. But there's a 40% gap between how funders perceive their understanding and how nonprofits experience it.

"If we're all trying to solve the same societal issues," Elisha says, "it's a problem if we have different understandings of what those are."

This conversation unpacks:

• Why data is a mirror—holding up truths we may not want to see
• How CEP turned around survey data in 10 days (not 6 months) to make it actionable
• The 40% perception gap between funders and nonprofits
• Why funders need to listen AND act, not just listen
• How to make data a conversation starter, not an endpoint
• Why joy is essential to leadership (even in dark times)
• How to think about data as movement infrastructure
• What distinguishes courageous foundation leaders right now

"Data is only powerful if people engage with it in the moment they need it," Elisha says.

This episode is a call to action. Not just to look at the numbers. But to do something about them.

TIMESTAMPS

• 0:00 - Data as a mirror: Holding up truths we don't want to see
• 3:00 - Civil rights legacy: Her mom sued for discrimination and won
• 6:00 - Why she fell in love with data as a tool for equity
• 10:00 - CEP's bold move: Making data public and moving conversations out of closed doors
• 14:00 - Navigating pushback: "Are you being too hard on the sector?"
• 18:00 - As a Black woman in data: Why she feels the need to show more evidence
• 22:00 - Data as a conversation starter, not an authority
• 26:00 - Turning data around in 10 days (not 6 months): Why speed matters
• 30:00 - THE NUMBERS: 81% increased demand, 68% negative impact, 61% existential risk
• 34:00 - The 40% gap: Funders think they understand. Nonprofits disagree.
• 38:00 - What distinguishes courageous foundation leaders right now
• 42:00 - How she leads with joy (even in crisis)
• 46:00 - Data as movement infrastructure
• 50:00 - Her call to funders: Listen AND act

"I don't know if we're going to win, but we got our best people working on it."

Darren Isom grew up as part of "Generation Integration" in New Orleans, the only generation between legal segregation and white flight. Now, he's helping philanthropy understand that it's not the strategist. It's the servant.

This conversation will change how you think about courage, joy, and who gets to build the future.

In this episode of Funding Bravely, host Marvin Smith sits down with Darren Isom, partner at Bridgespan Group and host of Dreaming in Color, to explore what courage looks like when you realize the world you normalized was actually radical.

Darren takes us back to 1980s New Orleans, where his parents met integrating a white high school (his mom is the same age as Ruby Bridges). He grew up singing the Beatles with Ms. Ziegler, a Black teacher with an afro "too late to be wearing one," in a school that was one-third Black, one-third white, one-third other, a world built on the belief that integration, not assimilation, was possible.

That upbringing shaped everything about how he works today.

This conversation unpacks:

• Why joy and optimism are acts of resistance, especially for Black Americans
• The moment funders realize: "You thought you were Gryffindor, but you might be a Death Eater"
• Why private sector rules don't transfer to nonprofit work (and never did)
• How younger generations are asking: How do we repair the harm our wealth created?
• Why this moment mirrors post-Reconstruction—and what the Harlem Renaissance teaches us about planting seeds
• The shift from funders as strategists to funders as servants with proximity to impact
• Why Black genius, when given space to create (not just navigate broken things), creates beautiful things

Darren reminds us: "Our torchbearers are most important when it's dark out."

This isn't about protecting systems. It's about building new ones.

 TIMESTAMPS

• 0:00 - Joy and optimism as acts of resistance
• 4:00 - Growing up as "Generation Integration" in New Orleans
• 8:00 - His parents met integrating a white high school (mom is Ruby Bridges' age)
• 12:00 - The Willow School: Singing Beatles, normalizing Black excellence
• 16:00 - How naming shapes power in philanthropy
• 20:00 - The shift: Funders as servants, not strategists
• 24:00 - "You might be a Death Eater": When funders realize their wealth caused harm
• 28:00 - A billion dollars is 1,000 millions—so why are we fighting over $100K grants?
• 32:00 - "This is what winning looks like" (Irvishie Vait's wisdom)
• 36:00 - Bright spots: High-network donors spending down, not hoarding
• 40:00 - Post-Reconstruction parallels: Planting seeds we won't see grow
• 44:00 - Where Darren finds community and why Black Americans seek beauty
• 48:00 - "Torchbearers shine when it's dark out"

RESOURCES MENTIONED

• Dreaming in Color podcast (5 seasons available)

• Sherrilyn Ifill's piece on post-Reconstruction parallels

• Donors of Color Network

What if everything you've been told about philanthropy is actually designed to preserve inequality?

Dimple Abichandani spent 20 years inside the sector and she's here to tell you how it really works. This conversation will change how you see wealth, power, and who gets to decide what justice looks like.

In this episode of Funding Bravely, host Marvin Smith sits down with Dimple Abichandani, philanthropic leader, lawyer, and author of A New Era of Philanthropy to unpack a question that's been haunting the sector: Can philanthropy actually meet this moment?

Dimple takes us back to her college days at UT Austin, where she learned what courage really costs. Then she pulls back the curtain on 140 years of "gilded philanthropy," a system designed not to solve problems, but to cover them up.

From Andrew Carnegie's legacy to today's $1.9 trillion sitting in endowments, this conversation exposes:

- Why spending only 5% annually preserves the status quo

- How tech billionaires use foundations to whitewash harm

- What "transformative alchemy" looks like when you mix capital with trust, imagination, and community voice

- Practices that actually redistribute power (not just resources)

This isn't about tweaking the system. It's about transforming wealth into justice.