What happens when we stop treating generosity as virtue and start asking who actually gets to define, fund, and benefit from social change? In this thought-provoking episode, we sit down with Robert Osborne, principal of The Osborne Group, to unravel the hidden power dynamics behind philanthropy. From toile curtains and “goody two-shoes subversives” to billion-dollar endowments and donor-advised funds, the conversation flows from quirky to critical, challenging the way we think about giving. Together with co-hosts Mim Plavin-Masterman and Alejandro Crawford, Robert explores why most philanthropic dollars don’t reach the communities most affected — and what it would take to shift the system. What if we redefined impact, centered justice, and stopped hoarding resources? What if philanthropy actually got it right?
Our guest, Robert Osborne, principal of The Osborne Group, brings 25 years of experience working with nonprofits and funders. Together, we explore:
From critique to creativity, we imagine what a more democratic, community-centered, and accountable philanthropic system could look like — and what would need to shift to make it real.
Editorial Producer: Kyriaki (Claire) Lampidou
Producer: Srijan Banik
Alejandro Juárez Crawford (00:00)
So the curtains behind the brilliant Bob Osborne are something I have to understand before we get into weighty topics.
What's the story with your curtains, Osborne?
Robert Osborne (00:15)
Those are toile curtains,
my wife loves toile. And so there's actually quite a bit more toile that you cannot see in the apartment. The wallpaper is toile, the curtains are toile.
There's different twol in my son's bedroom. Yeah, there's twol everywhere.
Alejandro Juárez Crawford (00:31)
Whoa, cool. there napkins?
Do we sneak little bits of twal into a non-twal situation? You might have a gadget and a phone, and suddenly there's a little ribbon of twal from your phone, or it's not something that appears Amelie-style.
Mim Plavin-Masterman (00:35)
Hopefully.
Robert Osborne (00:48)
I don't think it appears Amelie style. think it's more like your wallpaper or your curtains or it's like decorative. I don't think you'd see it on the napkins. Yeah. Yes. We used to have wing back chairs that were upholstered in twelfth. Yeah.
Mim Plavin-Masterman (00:55)
Yeah, upholstery.
Alejandro Juárez Crawford (01:02)
See, my mind has it like a big fractal at this point where like suddenly parts of your face have like 12 pattern sort of, you know, expanding on them, slightly pixelated, but you know, back and forth image, shaky image. Mim, is this something you've heard of? Am I the only one here? This is Mim who has equipment to fold her clothing. Okay, so I should have known.
Mim Plavin-Masterman (01:18)
⁓ yeah, you're the only one. Twal is, I mean it's very French.
I do.
It's okay. Yes, I have a, I'm not, I'm shamed of it. I'm proud of that. But no, twal is, it's very like specific. It's, I mean, you see it all over. I would say often less is more. But the pattern is really pretty. Often it's like very country, but sort of stylized country. And I actually looked it up. It's probably two or 300 years old as a style. And it's like people fishing, people, you know,
chopping down a tree or sitting under a tree reading, it's all like very cute and pretty. like in the last, I don't know, 20, 15, 20 years, people have taken that style and done something sort of subversive and fun with it. So I have a twal in my house, it's called Brooklyn Twal. they took the idea, it's all done in that twal style, but it's the Coney Island Cyclone, it's a Nathan's Hot Dog,
Alejandro Juárez Crawford (02:08)
Mm-mm.
Mim Plavin-Masterman (02:20)
biggie, like it's really kind of fun and so from far away it looks very formal, but then when you get up close you realize it's actually something quite different, which is probably, I love that sort of subversive. My husband calls me a goody two shoes subversive, I'm like that's probably accurate, so like.
Alejandro Juárez Crawford (02:36)
Yeah, ma'am,
I think you've done something very interesting. You've shown us that we are defined by the eccentricities that we're proud of or ashamed of.
Mim Plavin-Masterman (02:44)
Okay, you know, it's
very early to be starting with eccentricity.
Alejandro Juárez Crawford (02:50)
says the woman with the clothing folding equipment. So like, this is an eccentricity as you've just stated that you're proud of, right? And what was your husband's language you just stated is very interesting. You're a goody two shoes what?
Mim Plavin-Masterman (02:57)
I am, I am.
was very
subversive. He's not wrong.
Alejandro Juárez Crawford (03:07)
Asborn,
you a goody two-shoes subversive too? Is this what's going on here? Is your twol?
Robert Osborne (03:12)
I was just thinking
about whether well the 12 totally my my wife I'm gonna have to tell her about the biggie the biggie 12 because it would combine the two her two biggest loves into one into one thing so I definitely
Alejandro Juárez Crawford (03:25)
So I'm
Mim Plavin-Masterman (03:25)
and it's in multiple.
Alejandro Juárez Crawford (03:26)
right about the
fractal. Your whole life is going to have more and more spread of Biggie 12. This is what's happening here.
Mim Plavin-Masterman (03:32)
Sorry, Bob.
Robert Osborne (03:33)
It's okay. I think I am a subversive Am I a goody two shoes subversive? Yeah, I could probably be less goody two shoes about it now that you now that you mention it, you know I'm gonna think about
Alejandro Juárez Crawford (03:45)
It's like a 1993
ironic band, right? The goody subversives. Go on, what were you saying?
Robert Osborne (03:51)
Pretty good subversives.
No, I agree. That's a good band name. I like it.
Alejandro Juárez Crawford (03:59)
I think I'm gonna become a fan, a super fan, maybe a groupie of the goodie subversives. That's where I fit into all of this.
Mim Plavin-Masterman (04:07)
Alright, alright.
Robert Osborne (04:09)
Yeah, let's do it.
Alejandro Juárez Crawford (04:10)
So.
Mim Plavin-Masterman (04:12)
Let's do it. Yes.
Robert Osborne (04:15)
I mean, is it our band? Maybe. Maybe.
Mim Plavin-Masterman (04:17)
Maybe, I mean.
Alejandro Juárez Crawford (04:18)
Yeah,
let's let's form this band right now. Right. Mim, you play the ukulele, the goodie subversive. I take it retracted, retracted center. So like the goodie subversive definitely has a mandolin player, play the mastermind on mandolin. But Bob, are you going to what are you going to do in this in this band? What's your role?
Mim Plavin-Masterman (04:21)
Okay, I feel like nobody wants to hear that No, played the mint. No, no, no, no, I played the mandolin you take that back Crawford. That is not the same instrument
Okay. Okay. We were going to lose all.
Robert Osborne (04:43)
know, you know, vocals, maybe, I don't know. But it's been a long time since I sang so it's gonna be
Alejandro Juárez Crawford (04:51)
And so
are these sort of earthy, are these refrains, are they spoken word? What are we talking about here?
Robert Osborne (05:01)
No, I mean, I feel like if we're subversive, I don't know, are we like a metal band maybe with a mandolin? don't know.
Alejandro Juárez Crawford (05:08)
Yeah, yeah, yeah, because the 12 thing,
sounds like it's bucolic, right? So it's to me originally bucolic. That's where I got the earthy thing. Right. But we're flipping. It's got to be a hardcore brand. Yeah, yeah. But a hardcore band where we all dress like we all have the like Calvin of Calvin and Hobbes on School Pictures Day haircut that I have. Right. Which is.
Robert Osborne (05:18)
Maybe. Maybe we're a hardcore band or something. I don't know.
Alejandro Juárez Crawford (05:34)
which is on purpose for those watching a video, not seeing a video version of this. I part my hair like one of my Chicano ancestors from like the 20s or 30s, right? And I do that very deliberately because, you know, I'm a little crazy, hopefully in a good way, right? Like, you know, I hope I'm good weird, but I find if my personal appearance is neat, then I'm all right. I used to know a guy who talked.
Robert Osborne (05:45)
Hmm.
Alejandro Juárez Crawford (06:01)
in a very goody two shoes way and dressed super goth. And our theory on him was that the goth dress got people to take him seriously because otherwise his voice was too goody two shoes for the rest of
Robert Osborne (06:14)
good strategy. Yeah, I like it.
Alejandro Juárez Crawford (06:16)
Alejandro Crawford. co-host is Mim Plavin-Masterman. And we're on a mission to make experiments of your own, not necessarily curtain experiments, but other experiments of your own feel as normal as watching videos on your phone. Welcome to What If Instead,
Mim Plavin-Masterman (06:36)
We have the pleasure today of being joined by Bob Osborne, who is the principal of the Osborne Group. And they're a boutique consulting firm serving nonprofits. They've been working in this area for about 25 years. They are really big believers in the power of nonprofits and the work that they do. And then also the intersection of philanthropy and nonprofits and how they can work together in theory can change the world for something better. And we'll sort of talk about the pros and cons of
that whole space and what you've been working in for the past 25 years.
Robert Osborne (07:08)
Yeah, sounds good. Thank you for having me.
Mim Plavin-Masterman (07:10)
if a wealthy person in a 40 % tax bracket gives a thousand dollar donation, the government lets them write off 40 % or $400.
But if I make that same donation, I'm not taxed at 40%. So I only get to write off like $250 because of I'm in a different tax bracket. from the implication of like the, feels like the system set up to benefit the really wealthy people who can give a lot of money because of how they can deduct it from their taxes.
Robert Osborne (07:41)
Yeah, well, there's upper limits on I, we could sort of, I don't want to get too much into the math, but yes, I would say overall that is, overall that is, that is true. ⁓ I would say, you know, that modern philanthropy exists essentially as a way of preserving wealth and, and power,
Mim Plavin-Masterman (07:46)
Yeah. Okay. Overall. Okay. Roughly.
Robert Osborne (08:01)
you have big Robert Barons essentially who
know, their wives gave them something to do, gave them agency that they maybe didn't otherwise have. It was a sphere where they could exert influence. And it was a way to preserve wealth, a way to look good in your community. And it was not something that necessarily benefited everyone. It was something that, you know, you were much more likely to make donations to organizations that serve people that
that looked like you, right? Or that were in your world or gave you some kind of personal capital out in the
we see today, even though the not-for-profit system has expanded and you see, you know, I would argue that it does do a lot of good, but
I don't know that we interrogate enough.
what the origins of philanthropy imply for how philanthropy is conducted today. I do think, led by the folks at Community Centric Fundraising, that four years ago or so, really started to ask those
Alejandro Juárez Crawford (08:58)
Mm.
Mm-hmm.
Robert Osborne (09:11)
in a meaningful sort of way that has gotten the whole sector asking those same questions as well. But yeah, it's set up to benefit the rich. You and I can benefit also, but
But it's a way of being able to assert to some level of influence out there in the world in a way that is tax deductible. Yes.
Alejandro Juárez Crawford (09:36)
So far we've talked about you've made the statement if you're clear about your mission, then. You can mitigate some of the pull of where your money came from to some extent. And I want to I want to.
interrogate that a bit, maybe through those questions that you've just
Robert Osborne (09:51)
Mm-hmm.
Alejandro Juárez Crawford (09:57)
use this phrase, you said,
it makes you more likely to serve the needs of, and these are words, people that look like you, right? And a big question that Mim and I have raised in our research is who?
whose problems are we solving? And do we giving the money, even if you're a small donor, you mentioned the three of us or something like that, even understand the situations of the people whose problems most need solving for all of our benefit, or do we need to give more power to them?
Robert Osborne (10:32)
those are big, big questions. So let me start with the second question,
from this?
I'm in this business because I genuinely do believe
not-for-profits can and do make a big difference out there in the world.
do think they're an important part of our system in the sense that our government really doesn't take care of a lot of the things that many other governments in the world take care of. And so we have this space and this need that needs to be filled through not-for-profits and
then you start to look at, right,
Where does the money go? And how do we even think about that
purposely don't use the word
that implies
just helping someone who's less fortunate for you independently of sort of the system that created that, the less fortune, as opposed
making real social impact in some meaningful sort of way that implies that we're trying to change things. We're trying to make something actually different. We're trying to create a different world. And I think that's really the power of philanthropy. And it shouldn't be reliant on generosity, right? It should be reliant on impact and making a difference
Alejandro Juárez Crawford (11:52)
Mm.
Robert Osborne (11:54)
do think that our default, like I was just at a conference last week, the International Fundraising Congress, which is a big fundraising conference that's held every year in the Netherlands.
was with Michelle
we were presenting on community-centric
think people are nervous that this is very different. What's being proposed these days is very different from the way traditional philanthropy is thought about, where it's very donor-centric and it's very much about gratitude towards the donor and doing what you can to keep that donor happy.
Alejandro Juárez Crawford (12:24)
Hmm.
Robert Osborne (12:30)
And I do think good fundraising is very much independent of that. But I would say that the way it actually is practiced is often practiced badly, where we give a lot of power to donors and they have a lot of say in where that money goes. And to your earlier point, it tends to go to specific kinds of causes, like higher education. A lot of money goes to higher education. A lot of money goes to the church. When you're talking about
Mim Plavin-Masterman (12:54)
Yep. Yep.
Robert Osborne (12:59)
institutions that are really genuinely like making an impact on a social, social level, it's much, it's much less
not as much money as you might think really go to
that are really helping out in some meaningful way beyond what's publicly, beyond public funding.
Alejandro Juárez Crawford (13:17)
Since we know you're a 12 subversive here.
interested in what were you presenting that could be threatening there?
Robert Osborne (13:27)
one, think we were presenting, really thinking about how we actually approach philanthropy and our fundraising practices. so they have a community-centric fundraising has a few tenants. One of them is, I think most of them are pretty uncontroversial. Like we within the fundraising world will kind of maybe debate.
some of them about like what makes good fundraising practice or not, but they're not, I would argue that every, the principles really are pretty, you know, make, make sense. But I think there's maybe a couple that are, that are really challenging. And one is centering, you racial and social justice, like that, that that should be the focus of, of charity and, and correcting historical, you know, historical wrongs
Alejandro Juárez Crawford (14:13)
Mm-hmm.
Robert Osborne (14:16)
That's the one I think that people get hung up on
find challenging, I think.
can talk about colonialism. You can talk about, you know, each country, each region has its own version of that in some way.
I don't think everything is race-focused, but think very often there are marginalized populations of whatever kind that could be helped by philanthropy that are not. My other pet complaint really is just the massive amount of money that just sits around and doesn't do anything. So the amount of money that's just in endowments of big foundations. Increasingly, people...
Alejandro Juárez Crawford (14:48)
Hmm.
Robert Osborne (14:57)
give to this tax benefit called the donor advice fund, which, you know, is like maybe the worst thing to happen to
People have been debating how bad it is for basically my entire career. But now it's like, it's the fastest growing category of giving. I think it's up to like 10 or 15 % of all giving goes to deaths, which is, which is
anytime you just have these pools of money that are being invested, I find that I don't think it has to be this way, but I find that they they tend to become an end of themselves.
it just becomes investing for investing
the pandemic happened and, you know, surprisingly few foundations spent beyond their five percent, the five percent they're required to spend year and annually of their of their principal.
not then, when, you know, when was it, when would have been a good
Mackenzie Scott's trying to spend down her whole fortune and it takes a long time. And so it makes you wonder even at the rates she's spending,
are we so afraid of spending more than 5%,
know? ⁓
Alejandro Juárez Crawford (16:00)
is a problem I'd like to have, but...
Mim Plavin-Masterman (16:02)
Yes.
want to follow
six or seven years ago, Michael Bloomberg donated almost $2 billion to Johns Hopkins to support need blind admissions. And everybody was like, you know, throwing a party. And then there have been regular videos last several years of like people donating to medical schools and the medical students were like screaming with joy and all this stuff.
to your point, that we're not changing the public policy, we're relying on these magnanimous gifts from philanthropists to solve these huge problems of college being overwhelmingly expensive for a lot of people, and medical school in particular.
when I'm listening to you talk about equity and justice, there's a way in which philanthropy and justice are not always aligned. And I guess my example would be,
volunteering at a soup kitchen or giving money to a soup kitchen isn't gonna end hunger, right?
So at some level, it's like you're asking the soup kitchen to take on an incentive of self liquidating of like putting themselves out of business because we've solved the underlying problem. So that's sort of my bigger question of how much of philanthropy is dealing with these surface symptoms and how much of it is trying to get to the actual causes to almost make the philanthropy unnecessary, either institutional arrangements or policy or whatever.
Robert Osborne (17:16)
I don't know that anybody has measured that, but anecdotally, I would say that that much of it is symptom is treating symptoms, right? You know, I don't think it should be, I think the strongest not-for-profits try to have, have an impact. think, you know, that sort of be, I try to have an impact that's beyond just serving, you know, surface problems. But I also think it's hard for them to do that. It's hard to operate at the scale to
have that level of systemic input, you really have to kind of evolve. Most not-for-profits are small and struggling and just trying to solve something in their community or mitigate some problem that they see in their community. And then when you see
systemic investments, they often are done by people who...
may not be the most qualified to do the work. mean, think, you know, like the Gates Foundation, think, means well. But I would also say that, you know, a big part of the reason we have test-driven, you know, education system for so long is because of the Gates Foundation, you know, and, you know, all the money they put into
good intentions, but...
There's also a very serious question of how much power do we want to give these big pools of money and how interested are they in really changing things?
Alejandro Juárez Crawford (18:38)
Mm-hmm. Mm-hmm.
Mm-hmm.
if you two allow me, I've heard these five big ideas sort of here. And to some extent we can pick which of them we go into and they're all related. But one is,
from your discussion about Teach to the Test, it's which problems we solve, A, but it's also which paradigm we bring to those problems, right? And when it's a Teach to the Test paradigm, right, that's the way traditionally, that's how Gates thinks, if I'm not being too reductive, and that probably works better for malaria than for math, maybe. Two, I'm not actually weighing in on that, I'm just raising that question. Two is,
where is the preponderance of resources applied?
are questions that bring up the big question number three, which is who are we asking, right? Not just who has the purse strings, which we've already started to hire, but who defines the problem, the paradigm, and even the way we think about solving
Because Mim and I have our...
are writing a book about how, as long as we ask the same people, instead of those folks you started to touch on who might be in the global South, understanding breast cancer awareness in the culture of Acra, as one of our guests on what if instead is talked about, then we're not gonna be able to solve this problem. That brings us to the fourth, which Bob, you brought up this very interesting piece when you said, if we're just focused on helping the less fortunate,
And we do that independent of the systems that made their misfortune predictable. Then we may actually just always
fritting around the edges,
if we're measurement based, then we're always focused on being able to get a direct result.
we tend to move away from enabling models, models that can enable lots of people to resourcefully solve their own problems.
Bob, how do you think about these interlocking pieces?
Robert Osborne (20:51)
I think the folks at community-centric fundraising have done a pretty good job of sort of putting out an alternative paradigm about how to be thinking about this work. So one is centering the social justice and racial justice and making that a core part of what every organization.
does in some way, to at least be thinking about that and thinking about how does our work actually have some impact on those that are less fortunate in society in some
so your average not-for-profit, is going to, let's say
I'm
food bank in this community, right? And I'm a big, I'm the big player, the big food, the food bank. And then within my community, there's, there's these smaller organizations that work on the ground and are doing, you know, also doing, you know, work around.
housing and other like causes of being of not being able to eat right and you have this this whole ecosystem right that it theoretically exists to solve the same problem except because of the fact that I need to fundraise and philanthropy and the way that philanthropy is sort of approached I Is like the big food bank might just Hoover up all the money that's available You know to all these other organizations and maybe I'm doing an awesome job and I redistributed which would be great
Alejandro Juárez Crawford (21:55)
Mm-hmm.
Robert Osborne (22:20)
But maybe I'm not doing that. Maybe I'm just, you know, I'm going to run programs for my sake. I'm going to duplicate the programs that these other organizations are running. I'm essentially going to put them out of business, right? Because I'm doing the work. And then, so the question becomes, you know, are we centering the mission of our organization or are we centering the community itself? And so the proposal is to really center the community and really ask yourself,
Alejandro Juárez Crawford (22:45)
Mm-hmm.
Robert Osborne (22:50)
Are we beyond mission? That the mission, your mission statement shouldn't be primary, but be thinking about how can I have the most impact in the community? Even if that means deferring gifts, re-granting gifts to other organizations, redirecting money to organizations that might be doing that better, some specific task better than you, but really starting to think about, are we actually helping the people that we say that we're helping?
Or do we just exist as a bureaucracy that exists for its own sake does do some good in the world, but is not is not really thinking about the systemic problems.
first question we have to ask ourselves is like, are we helping people? Are we making a difference? Are we are we changing the systems that create
these problems in the first place, or are we
just kind of giving people money around the edges and not thinking about this, you know, in a holistic sort of
going back to Gates for a second, you know, Microsoft is a huge
open AI, for example.
their dreams are realized, it's going to be a massive environmental problem
So if we don't think about like, like a lot of times we think about it, like we're going to create this whole new problem, right? And then we're going to donate.
a fraction of that money back into the system to like mitigate the problem that we caused in the, in the first
What is, what makes the most sense in terms of investing? How can we as foundations or as major donors or, or as lots of small donors really invest in?
an actual impact of some kind and try to solve systemic problems, which I think we could do if the will was there to do it. The money is there. Again, we're sitting on many, many billions of dollars that we could unleash to solve problems.
Alejandro Juárez Crawford (24:41)
How would we
do it? How would we, I just wanna fixate on you said, I think we could do that experimentally. You don't have to have all the answers. What would we start trying to do?
Robert Osborne (24:50)
think these foundations, so one, we'd get rid of DAFs probably so that money is not just locked up. And because for those people who don't know what a DAF is, I basically I donate to my own donor advice fund. get a tax deduction today and now I have my tax deduction. So there's not a lot of incentive for me to now distribute that money to charities because I've already given it to a charity, me, essentially my donor advice fund.
People will make donations from that, but a lot of the money sits around and gets invested with institutional investors
think that is a big problem. think foundations sit on a lot of money that they don't need to be sitting on. They could ask themselves the question of, how did we get our money? Do we owe anything back to the communities that
99 % of the time, we probably exploited or was extractive in some particular
some of these are very much existential issues. And so why are we just sitting on all this capital that we could deploy in ways that are interesting? We could run genuine
You know, appeasing people or...
Alejandro Juárez Crawford (25:58)
But what would have to
change to run genuine
And I see that Mim, you have a burning question, but let me hold that question. Go on.
Robert Osborne (26:07)
I think it would really just be a change in attitude about the way at least foundations thought about it. And financials represent a pretty big chunk of philanthropy.
I think individuals represent a much larger part of that.
if you're a small little organization that's unproven in some way, you're not getting money. you're run by the people that you, ⁓ you that, that's, that you serve, you're not going to get money because people give to what they know and who they, and who they know. And, and, and I'm speaking very broadly. I'm not saying this never happens, but it could happen at a much, much higher.
Alejandro Juárez Crawford (26:39)
Damn.
Mim Plavin-Masterman (26:42)
Yeah. Yeah.
Robert Osborne (26:46)
much larger scale than it does.
Alejandro Juárez Crawford (26:48)
Hmm.
Mim Plavin-Masterman (26:49)
seems to me that there's an accountability issue and two, it seems to me that there's a transparency issue and that both of these are related to some of the stickiness of the philanthropy problem. when I was preparing for this, I did a little bit of research. I looked up, there are about a hundred thousand private foundations in the U.S. 90 % of them have no website.
It's kind of amazing. So there's all this money, but there's like no way to even find out who's running these foundations. Then I'm sure you already know this, Bob, but for our listeners, you can't be unelected for the most part in foundation. they're relatively unaccountable. it's, especially if it's like your family foundation, there's not really like a competitor who's going to put you out of business. And to your point, there's no incentive to spend your money down to self liquidate and put yourself out of business. So all of that to me says that one of the things that's
that we need to think about if we're really gonna make systemic change is how to increase accountability or how to increase transparency. And I guess the way I would frame the question is, is it a policy question? Is it an incentive question? Like is a carrot or stick? Is it both? And then if so, what's the carrot and what's the
Robert Osborne (27:51)
Hmm.
could get rid of you could get rid of deaths You could have requirements of spending more than you know, your your five percent requisite, know spending I think you could You know the on the transparency question if anything, we're probably moving towards less transparency in these in these matters then then more than more transparency Unfortunately, I mean foundations who have to file a 990 which
you know, does provide some information about it, but it's not easy to find
from that perspective, yeah, I mean, it's your own money, right? Like that's the way we work here in the United States. don't have, there's not.
a lot of accountability with how you, you where money goes and, ⁓ and how it flows and who it flows, you know, who it flows to. I do think that we, you know, in the not for profit sector can be more transparent and encourage people to be more transparent. I think that's something as a sector we aren't as good at as we, as we probably could be on that accountability question. But, you know, I do think you could do any number of tax law reform reforms that just make it.
⁓ you know, that would incentivize people to, or, or force them to spend more, more of their money. That if you're to get this tax deduction, that's fine, but you need to, you need to spend it on the public good at a rate that, that is higher than people are currently, currently spending. And your money would still last for a really, really long time. You know, it would last for a really, really long time.
Alejandro Juárez Crawford (29:21)
Hmm.
Mim Plavin-Masterman (29:28)
Right. Right.
Alejandro Juárez Crawford (29:30)
you
Mim Plavin-Masterman (29:31)
So to me, there's a twofold measurement question related to accountability. If one is
If we're so focused on measuring the thing, maybe we're missing what's really the problem, which is one piece. But the second is we can make this foundation look like it's doing a lot. If we make the numbers look a certain way, if we ask a question a certain way versus a different way, we can show a lot of on paper progress also without getting to the root of the problem. So that still seems to be like an accountability issue of how do you really know that they're helping people?
Robert Osborne (30:06)
I can only think of one not-for-profit that measures really, really, really, really well.
Everyone else is like apples to oranges year to year year. It's one of those things where people want to hear it. There's this sort of movement towards accountability. I would say, you know, it's somewhat driven by the money that's coming out of like Silicon Valley and sort of that way of thinking, like everything needs to be measured.
If you wanted to be rigorous about measuring, you'd almost have to start, you know, you'd have to become like a think tank or a, like you'd like have some division of your, of your organization. That's like just focused on this. And some organizations do have people that are dedicated to it because they genuinely want to know for themselves, whether they're being,
effective or not. But I think most organizations find the level of measurement burdensome, ⁓ in a way that, ⁓ because it's not.
rigorous and so it's just burdensome for its own, you know, for its own
speaking broadly because there are foundations out there that really do take it seriously talking to people within the community, understanding what those, what's going on in the community, not relying on their own expertise, but relying on what
you know, what people within the community are actually saying that they need and want. think if you look at like developmental organizations, like aid organizations, there's a real power shift that most of them are doing at this point to like really leave the decision making and questions of effectiveness to the folks that are on the ground. But that could be adopted by many more parts of the sector that could be adopted with, you know, more rigor.
Alejandro Juárez Crawford (31:29)
Mm-hmm.
Robert Osborne (31:48)
and I think a lot of organizations, you know, over the last four years have sort of asked this question and then, but I haven't really seen meaningful, meaningful, meaningful change, you know, because we were at the, at the end of the day, like, you don't have to be accountable to anyone, right? Like it's my money. I'm going to do what I want with it. And that's the system.
Alejandro Juárez Crawford (32:06)
Yeah.
I just co-created a nonprofit and we have the head of data for a for-profit company on our board very intentionally. And maybe that's something.
You know, there are a lot of data scientists being released into the workforce right now. Maybe that's not crazy, but I actually am going to be selective and focus on really four words. You said five words. You said they're not getting the money and you were talking about if you're a smaller organization and especially if you're from the served community and then you said those words, they're not getting the money. And I want to focus on that because one of the things that Mim and I work a lot on is
resourcefulness, resilience, capacity building, all the things that happen as an effect of creating your own solutions in a community, in an industry, right? All the little relationships and trades and skills that get built up as you do this. And when I heard you say they're not getting the money, I had these alarm bells going off. So hold on, all the capacity to solve these problems is outside the community.
Is there, can you give us any crazy ideas that you have on how we could change that?
Robert Osborne (33:25)
think if you look at the community centric model, which really focuses on the relationship between not-for-profits and themselves, we could take that further. We could really take a look at what I would call an ecosystem model where you match capital.
you match competencies, have these volunteers that are data scientists that understand how to do whatever within the community, that are lawyers, that have professional expertise of whatever kind, that have content expertise of whatever kind. You have different not-for-profits that understand, that have a shared vision for what they want to have in the community and a shared understanding of what role each might
might play and, and, know, through community mapping, you know, exercise and people are thinking about this. People are, are, are experimenting with this. I don't know that. ⁓ I think it's too soon to see where things are going. You know, I think we're sort of still in the, developing like, what is this? What does this look like? But I think that would be a great model, like really thinking about, you know, just bringing in, you know, however you want to define a community.
you know, who are all the players in the community, what capital is available, what expertise is available, and let's solve some problems together rather than competing, competing against each other for, you know, what is perceived as scarce
Alejandro Juárez Crawford (34:51)
Hmm.
Robert Osborne (34:53)
even within the existing system, I think if we cooperated more and really had that mentality, because right now we're not like, come out of fundraising. My I'm judged by how much money I raise for my organization, not for your organization, not for the community, not for solving problems, just pure money. How much money can I, and I'm good if I can raise the money and I'm bad if I, if I don't raise the money and we could define that.
differently. And we look at that at some of the federated organizations that we work with that have like a national office and affiliates and start to experiment a little bit. like, well, what if you did get like, if you just help the whole federated organization, shouldn't you get credit for that? So you start to see those kinds of examples. You start to see organizations now that are re-regranting, that are turning down grants sometimes in favor, but recommending a smaller organization. So I think
I think at least within a certain number of progressive organizations that I think people are thinking about this.
we need to kind of switch the mentality of my sector and how we think about these problems.
Alejandro Juárez Crawford (36:05)
I want to
Close on that note, because I think those questions you asked really give those of us interested in changing these outcomes food for thought. I want to thank you, Bob. You can add any closing bon mots, you and your 12 curtains if you want. But let me just say thank you so much for helping us think about the crazy stuff we could do that might just be incredibly sane.
Robert Osborne (36:38)
Well, thank you. Thank you for having me. It was a lot of fun. And yeah, thanks for giving me a forum to just vent all the little things, the things that I'm thinking about in my world. But yeah, it was a lot of fun.