Sasha Rabsey on Radical Generosity, Transformative Giving

Sasha Rabsey has heard the same story more than once. Most recently, she heard it at a conference, where a young woman presented on her work with trauma organizations. Her funding came from a series of high-level civil and private sector awards–enough to start ten different programs supporting women recovering from trauma in Latin America–but as the awards began to dry up, she found herself floundering for funding.

sasha rabsey
Sasha Rabsey is a philanthropist and advisor. She is the founder of the HOW Fund and the Senior Philanthropic Advisor with Collective Capital Philanthropy. (Photo Credit: Collective Capital Philanthropy)

“I’ll take anything you can give me,” the young woman said, echoing scores of people Rabsey has worked with over the years. “If I don’t start winning more awards, we’re going to have to close more than half of our locations.”

The conundrum here is one Rabsey has worked to circumvent over the course of her career as a philanthropist and advisor.

“You cannot use a business model in philanthropy,” Rabsey says. “The bottom line can’t be about profits and investors. It just doesn’t work that way. Non-profits don’t behave like businesses because they don’t make profits or answer to shareholders. The one thing I always ask is, ‘Where are you getting your funding from?’” she adds. “Every nonprofit that really does well, that’s really in it for the long term, has engaged and built relationships with everyday givers. Those are the folks who form the backbone of your work.”

You’ll hear Sasha use this term a lot. Everyday givers are people who give smaller amounts of money (compared to the ultra-wealthy), but tend to give a higher percentage of their income. They also tend to contribute more often, whether through personal fundraisers, recurring donations, or honorariums. And often, they’re taken for granted or ignored in favor of “bigger fish,” who donate larger amounts of money–but are less likely to give again.

“We know from tons of research that everyday givers are the folks who stay,” Rabsey explains. “They give less than what the big funders give, but they stay with you. They are the backbone of philanthropy–it’s not the billionaires. It’s the people who give through their church, pledge their remittances, contribute to emergency disaster relief. They keep organizations going.”

It’s a common but understandable trap NGO leaders and bright young world-changers fall into all too often. They spend so much time focusing on “big” one-time funders–angel investors, corporations, billionaire do-gooders–that they lose sight of the people who will support their visions for the long haul.

Sasha Rabsey is a philanthropy advisor and the founder of the HOW Fund, an organization that seeks out grassroots leaders to boost their campaigns through trust-based giving programs. Alongside Managing Director Anne Elgerd, Rabsey forms the second half of Collective Capital Philanthropy, an advisory firm that supports individuals, families, and foundations with sound philanthropic strategy.

Rabsey always knew she wanted to do something in service to women and girls, but it wasn’t until she had the financial resources that she found her philanthropic niche.  

“For me, it was always knowing I wanted to do something for women and girls,” she remembers. “When I discovered that women and girls are seen as a means to an end, I realized that what’s necessary for inclusion is to see the idea of engaging and including women as something that’s fair, just, and right. It shouldn’t just be a reaction. Many early campaigns turned women and girls into this shiny object, this marketing tool.”

We’ve all seen it: campaigns that claim a single donation can change the world, organizations that could transform society with the help of one massive lump sum.

In reality, we all know feminist philanthropy is a lot more complicated than that. It’s layered, it’s nuanced–ten micro-grants to grassroots community organizations can have a much larger overall impact than a single large donation.

This approach informs much of Rabsey’s modern strategy. Through micro-financing, collective giving, and grants made through a trust-based lens, Rabsey has been able to amplify the donation dollars of entire networks to great success.

“There is a mythology in philanthropy that says, unless you have hundreds of millions of dollars to give away, you can’t make an impact,” Rabsey explains. “But it’s those everyday givers who make a difference historically.”

The theory is based on the concept of momentum. Many grassroots organizations start out with an idea, but lack the funds to make that idea a reality. It can be next to impossible to get initial funding, but once donation dollars start coming in, organizations attract the attention of other donors.

This is where the HOW Fund comes in.

“It’s very common in philanthropy that funding begets funding,” Rabsey says. “So, if you have a great idea, you might hear, ‘That’s a BRILLIANT idea! Once you get some funding, come back and we’ll consider it.’ The HOW Fund works to act as that seed funding, which will hopefully lead to more funding.”

Grassroots organizations resonated with Rabsey and her family.

“At first, [the HOW Fund] funded programmatic ideas, but then we started looking more closely at the underlying causes of the systems that were oppressing women and girls,” she says. “From there, we started to focus more on  movement-building initiatives. And now, we look into movements and seed funding that can be leveraged for bigger ideas. We try to support those actors who are trying to do the work toward greater systemic change. It’s grown from, ‘These are great programs that are doing individual work,’ to wanting to work directly with grassroots organizations that are trying to get those programs off the ground.”

Beyond seed funding, Rabsey found herself looking for new ways to help.

“I asked myself, ‘What else do I have to offer? What really makes me feel purposeful?’ The answer was building relationships,” she says. “We want to bring our funders to the position where it’s not traditional philanthropy, with the funder at the center of the work. Instead, the center becomes the transformational process that’s happening on the ground. You’re building relationships. You’re creating trust. It becomes very personal, and at the center of it is joy.”

This trust forms the basis of Rabsey’s philanthropic style, a mentality she tries to pass on to her advisory clients.

In her work with Collective Capital Philanthropy, Rabsey often tells her clients to focus on a transformational, rather than transactional, approach to giving. “When you go out and you listen, and you’re fully immersed in equity, using that equity lens to solicit feedback and create this trust-based relationship, you’re going to get the truth. You’re going to hear the challenges, see the impact, and see the transformation on the ground and in yourself. Talk about impact! It’s so much greater.”

Prior to her work with Anne Elgerd and Collective Capital Philanthropy, Rabsey headed a giving circle called Present Purpose Network. This donor and grantee network was built on bringing the concept of transformative giving to a group of women who never saw themselves as philanthropists.

The goal of the program wasn’t to give away millions of dollars. Instead, it promoted the values, behaviors, and actions behind trust-based philanthropy. Through monthly online meetings, Present Purpose Network grantees and donors came together to discuss their challenges, learn more about their work, and come away with rich understanding and a mutual learning experience.

The members were not multi-millionaires. In fact, most members gave less than $2,500 over the lifetime of the Network, with many contributing as little as a few hundred dollars. Some of the members struggled with the concept.

“It just seems like such a small amount of money,” Rabsey says. “I remember one woman said, ‘You can’t do ANYTHING with $2,500, so why would I waste my money?’ We wanted to prove that wrong.”

Present Purpose Network has since closed its doors to new members, but the HOW Fund continues its work by supporting some previous grantees.

“We still do some funding, but that’s a well-oiled machine because we’re staying with the partners we have,” says Rabsey. “With the COVID-19 issue, it’s been about reaching out to partners to ask, ‘What do you need? What are you seeing? How can we help?’”

Currently, Rabsey finds herself spending a lot of time passing information between other philanthropic advisors in her network. With so many clients seeking COVID-19 emergency funding, Rabsey’s new focus is making sure enough eyes are on the issue of equity in the face of coronavirus.

“We are all in this space where we want to make sure that equity is being looked at,” Rabsey says. “It’s important that we give, but it’s just as important to see that this crisis is highlighting equity issues between gender and race. People are really hurting in ways that aren’t just about medical needs or salaries, but because nonprofits are coming apart at the seams. This isn’t the time to be restrictive. It’s the time to be more expansive with funding.”

“Right now,” she adds, “Anne and I are trying to answer the question: What is coming out of this moment that we need to add into our work? We need to educate funders in practices that will be sustainable in the long term. We need to adapt; we need to be more creative. What we can do is sit in this moment and never say, ‘When all this is over, let’s go back to business as usual.’ It’s not ‘business as usual.’ It’s not normal. We need to help our clients move away from that ‘business as usual’ mentality and find a ‘new normal.’ When it comes down to it, we need to embrace even more equity within this work.”

Looking back on a lifetime of building networks, supporting philanthropists, and starting conversations, Rabsey sees no prescriptive rules for building a network.

“It takes a lot of glue,” she says. “And that glue comes from not feeling like you want to create or own the network, but that the network is in and of itself its own entity. As philanthropists and as advisors, we need to be courageous, show humility, have purpose–you need to be able to step back and not feel so much ownership over your network, but rather see who is going to be a part of that network, and be ready to share it.”

It’s been a learning experience the entire way. No philanthropist starts out maximizing their donation dollars to the fullest, and Rabsey is no different.

“In the words of my dear friend Donna Morton, my end goal is to move massive amounts of money from harm to healing,” she says. “I want to be a small part of changing the way we think about traditional philanthropy. Collective Capital Philanthropy is one way we can get out there and tap into people’s natural altruism. We can tell them, ‘Let go, and follow the beauty of letting go.’”

“For the first time in my life, I’m more purposeful about which networks I want to be a part of,” Rabsey adds. “Some networks can fall into the trap of turning into cliques. But I try to look at my work with radical generosity, and try to tell people, ‘This is amazing, what you’re doing here. I want to be a part of this. And I want everyone to know about the work that’s happening here.’”

To learn more about Sasha Rabsey, read about her work with the HOW Fund and Collective Capital Philanthropy.


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Author: Maggie May

Maggie May is a small business owner, author, and story-centric content strategist. A Maryland transplant by way of Florida, DC, Ireland, Philadelphia, and -- most recently -- Salt Lake City, she has a passion for finding stories and telling them the way they're meant to be told.

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