Funding Rural | Episode #8 | Season 3: Gretchen Guess “It’s Always Been About Service”

Gretchen Guess is president and CEO of the Rasmuson Foundation in Alaska, where 80% of the population lives in remote areas without road access. Gretchen has lived there all her life and served terms in both the Alaska House of Representatives and Senate. She’s brought her public service experience to Rasmuson Foundation, which is one of the largest funders in Alaska and centers the community in all of their grantmaking.

“If you want to get something done; if you have a theory of change; man, go to rural. They’ll get it done.” – Gretchen Guess

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About Gretchen Guess

Gretchen Guess, a born-and-raised Alaskan who gave back as an Alaska state legislator, school board member and health care executive, returned to the place of her roots in 2023 to take the helm of the Foundation as president and CEO.
Gretchen started her professional life working for the administration of then-Gov. Tony Knowles and for a telecom, Alaska Communications. She served terms in the Alaska House and Senate and also on the Anchorage School Board, including as president. When she won her Senate seat in 2002, she was the youngest woman in Alaska to attain the office. In the state Legislature and on the Anchorage School Board, Gretchen worked to bridge gaps between stakeholders. After retiring from the Legislature, Gretchen spent 15 years in health care management and leadership including six years in planning and development with Providence Alaska. She holds a bachelor’s in economics from Carleton College in Minnesota and a master’s in public policy analysis from the University of Rochester.
Gretchen was honored by the Alaska Journal of Commerce as a Top 40 under 40 and as board member of the year for Standing Together Against Rape, or STAR. She also served as a Johnson Fellow with the U.S.-Japan Foundation, as a Henry Toll Fellow with the Council of State Governments in 2005 and as a trustee with The Nature Conservancy – Alaska chapter.
Gretchen enjoys anything with her almost grown children, basset hounds and friends. You often can find her on the pickleball court or skiing, biking, hiking or volunteering.
Her official start day at Rasmuson Foundation was Feb. 28, 2023.

“Why don’t you just go sit and be in community for a bit? Be at the coffee shop on the block, or fly into community and do things with community instead of to community.” – Gretchen Guess

Discussion Questions

  • Gretchen referred to Rasmuson as a “responsive grantmaker,” one that responds to what the community says it needs. Make a list of the grants your organization made in response to community needs, rather than an initiative started within your organiztion.
  • How can your organization flex for more “Open call” opportunities? These are often great ways to let community needs surface..
  • Gretchen mentioned the community conversations her board hosts where they go into a community and invite partners to join them at the local coffee shop. This act of showing up for a few days and making yourself available is powerful. In what ways can your organization incorporate this practice?

Resources

“We focus almost exclusively on being a responsive grantmaker —we’re funding what is a community priority and what the community says that they need—because we know that’s sustainable. That’s how you have impact.” – Gretchen Guess

Transcript: Episode #8 | Season 3: Gretchen Guess: It’s Always Been About Service

Erin Borla 0:00
It’s funding rural I’m Erin Borla with the Roundhouse foundation as a place based funder who prioritizes rural communities. I’m always excited to meet foundations from other regions who are also prioritizing rural and indigenous

Erin Borla 0:23
communities in their area. Gretchen Guess is President and CEO of the Rasmussen foundation in Alaska. She’s lived there all her life and was elected to both the State House and Senate before joining the foundation. The Rasmussen foundation is one of the largest funders in Alaska, and if you want rural, Alaska is the place to go.

Gretchen Guess 0:44
So Alaska is 12 New Yorks in North Carolina’s two and a half Texas. It’s very big. And we would consider the entire state rural. I think most people would. But half the population lives in Anchorage. So the population is 700,000 a little bit over 700,000 we have a road system, but 80 we have 350 places. 80% of those don’t live on a road system. So most of our places, even though most of our population lives on a road system, most of our places do not so those are communities where you either boat or you fly or you stow machine in and out of so it takes rural to a whole nother level. There are communities where maybe, if they’re lucky, there’s a barge once a year that may bring in goods, but then everything else is flown into the community, often on the oceans or the rivers of Alaska.

Erin Borla 1:48
Wow. It’s, I mean, you think, and you can, you think you can comprehend the vastness, but to talk about it in that way where there is just not access on a traditional road, you’re you’re flying, and you’re snow machining, and that that’s far,

Gretchen Guess 2:06
that’s far, and it makes makes rural a whole different. If you can drive to it in Alaska, we don’t necessarily consider it rural, although some of those communities, everyone would, yeah, it is, and it brings a resilience to the people and a community that’s just wonderful and lovely and steeped in indigenous culture, and we see that throughout Alaska and its various indigenous cultures.

Erin Borla 2:37
You have a long career of public service, and you were elected to a variety of positions. What made you want to go into politics and then jumping from politics to a position like this?

Gretchen Guess 2:50
I answered the question, could I do something, versus should I do something? I was I was asked to run for office, and I was like, Oh, I can do that, because I’ve worked on campaigns most of my life, and then I got elected and learned really what public services is all about. But it was wonderful. I represented the one of the most diverse neighborhoods in the country per capita. So anchorage has 100 languages spoken in its homes. It’s an amazingly diverse place, and my neighborhoods had all of that diversity, and I just loved it. So, you know, you make the leap from this to any other parts of my career, it’s always been about service, and that’s how I think about philanthropy, is that we are here to serve Alaska. It’s not about us, it’s about the folks on the ground doing the work improving their communities, and we just get to walk alongside them in their work.

Erin Borla 3:48
We work a lot with with government officials, whether they’re at the federal or the state or the local level, and clearly that’s something that’s important to you, to be able to highlight those stories of the folks on the ground. Where do you find the most friction, I suppose, or so, where is it challenging? And then where do you really see success? In trying to work with policy makers to say, Hey, this is what we’re hearing in philanthropy, and this is how do you find those relationships, and where do you find success?

Gretchen Guess 4:21
Alaska is great. I think like any rural place, we all know each other. It’s a one degree of separation, and I think that makes it easier to get things done. We all know each other. We all have a love for those places. I think when I’m working with national folks, it’s really understanding what rural is. Just even take the recent public media rescission that that occurred, that is our emergency management system here, like we’re not talking about NPR and PBS, we’re talking about tsunami warnings. Alaska hat is the only state that the FCC waves. So you can do. Personal messages on public media. So when someone’s missing, they’ve gone out hunting and they’re missing that goes out over the airways. Public Media in Alaska saves people. But folks don’t, you know if they don’t really understand what rural means, and they don’t understand what rural Alaska means, a lot of my my my work nationally is translating and trying to find those stories and connections that we don’t have internet everywhere we had our internet cable get cut and a half years ago, and so there was a swath of western and northern Alaska who had no internet for six months because the ice cut the cable under the water. So the understanding of of that not everything you have in an urban place, you have in a rural place, and a lot of that translation in that it it’s just more expensive to keep rural communities going. But rural communities is what provides us in the lower 48 provides us our food right in Alaska, it it provides us our natural resources. It also provides our fish and all of that that there’s, there’s a part of, yes, it’s cheaper to provide things in an urban setting. But we are more in America. We’re more in Alaska than our urban settings. So I think making those, those translations, and then trying to get people out in a couple weeks will be our grant makers tour. So we take national funders, and we’ll take them out, out in Alaska to try to to see and hear people’s stories about what’s going on, what help do they need? On the federal level, one of the things that we’re really running into, besides just the change in direction, is things are so formula. And I would ask you this, Aaron, because you do such great work and role, things are such formulaic that it will take a community five years of their HUD funding to get a half a million dollars to build one home in rural Alaska, right? So just the having every little amount of federal funds have its own formula and its own reporting, and you only can use it for this, I think, misses the boat on what is a community priority, what our community needs. How do we use our funding for those and so at the Rasmussen Foundation, we focus almost exclusively on being responsive. Grant maker that we’re funding, what is a community priority and what the community says that they need, because we know that that’s sustainable. That’s how you have impact.

Erin Borla 7:49
Yeah, I think that’s an important piece. I know as we expanded over the last five years at roundhouse, we had people ask, I can’t believe you’re still or state, I can’t believe you’re still doing open call grant applications and not just doing invited proposals at a certain amount. And the reality is, we don’t know what’s happening on the ground in every single community. We have to get to those communities and allow and sometimes we can’t even get there. So we’re waiting to hear from them and our partners on the ground. Hey, did you know that this library closed? Or did you know that this community radio station is losing their tower, so we needed to keep that open call open to be able to ensure that we heard from everybody as often as possible. How are you accepting grants? You’re not in every community, everywhere, all the time. It can’t be possible.

Gretchen Guess 8:40
We do that. No, but we were last year. We were 50 communities. That’s pretty darn close. Yeah, and I think I’ve been in, I don’t know, maybe 12 so far, just myself. So we do a lot of travel. We have a, hey, if you have an idea, just call us. Approach with very high touch. We actually have open bookings for our program officers, you can go online and book time with a program officer and just talk to them about an idea. So a lot of it is just trying to make it easier for folks to to access us. But we have two rolling programs up to $35,000 we call them our tier ones, and up to 250,000 which is our community support, our tier ones we attempt to turn around monthly. And those are really, those are the small dollar big impact. And when you become a big organization, you often think, well, I’ll just give bigger awards out. But what we find is the $3 million we spend on small technology upgrades vans. It’s, it’s how the people are going to get the meals on wheels to the seniors in the homes the you know, anytime there’s conversation about, well, maybe we shouldn’t do that. That is, it’s a couple 100 grants a year. It takes a lot of time, but those are the ones right where the people, they don’t need a lot, and what they do, and the impact that they have with those small amounts. And then we have larger grants, you know, above 250 but they’re all responsive, and we just, we’re a strong believer that if we can make it easier for people to access us, even if we’re not in community, then they know, they know, hey, maybe we should talk to Rasmussen about a grant. The other thing we try to do is, when we’re out on a site visit, we don’t just drive by and roll in for a site visit and roll out one you can’t right? This might be only one flight a day to that community, where you might get stuck in that community for a few days because of weather, but we try to have like, open coffee hours or open time in community. My board myself go on community conversations four to six times a year, we just go and we’re in community for a few days, visiting grantees, having receptions. So just a lot of different ways of how do you get out in big rural in big rural spaces?

Erin Borla 11:14
Yeah, I think that’s really innovative. You talked about the grant makers tour, which I think we get asked a lot, just in general, when we talk about rural because we talk about especially national funders, like, get closer to it. How do you get closer to rural places hard to hate, up close, right? How do you get next to those folks and get in that community and really understand it? And it’s hard to do that if you’re based in Chicago or New York or Atlanta, you can’t be everywhere. So you offer this tour. What’s the expectation of funders that come on a tour? Is it just a cool I get a chance to go to Alaska lucky Maine? And you know, how do you set those tours up? What are the expectations

Gretchen Guess 11:58
we my predecessor started them in and I’ve been, I’ve been adjusting the last few years on them. I think the value of the tour is not, hey, we expect you to give money next year right away. We all know all of our organizations have processes for grants. My goal is to have people who either are doing grant making Alaska, or should be doing grant making Alaska, or interested in grant making Alaska, come and join us and understand Alaska a little bit better. So when they’re in their entire career thinking about places, they don’t get overwhelmed. I even even with Indian Country, I’ll meet funders who are saying, Well, why do Indian country in the lower 48 but not in Alaska? It just seems too complicated, because we have a different indigenous governance structure in Alaska. So a lot of it is breaking down those barriers, having people really understand what rural is, how to access, being able to to invest, also being able to see the beauty in rural that really it’s the same two people everywhere, right? So if you want to get something done, if you have a theory of change, like, man, go to rural, like, they’ll just get it done and pilot something. If you pilot something in rural and it works, you can, you can make it anywhere. Make it work anywhere. So we try to focus on that and on really just knowledge and access. And then we are staffed to support people who want to fund in Alaska. So that is an expectation of our of our board. Sometimes it’s someone’s coming up and just needs to know, where do I stay in Cordova, Alaska, okay, the reluctant fisherman is, there you go. And sometimes it’s, Hey, we’re looking for people that are working in maternal health. And you know, what do you know about organizations, or we got a grant from this place, but this doesn’t really make sense. Can you help us interpret what’s going on? So we also see ourselves as a resource to non Alaskan funding in Alaska, and I think that’s just important when you have such a big, vast, diverse place that doesn’t have a lot of philanthropy in it.

Erin Borla 14:24
So you did not come from philanthropy. You have this very diverse background, doing a lot of public service. I love that you talk about the importance of service. How have you found the philanthropic landscape and being able to share initiatives that you’re working on? What are things that philanthropy is doing really well? Where do you wish? Man, I think we could do this slightly better, if only

Gretchen Guess 14:48
the amount of intellectual caring, just the deep caring about people and place in whatever philanthropy is focused on. That is wonderful, and it is very mission driven. You can disagree with someone’s maybe mission at their foundation, but they, the people that are doing the work, are very mission, mission driven, which I think is is wonderful, and I have found the community very accepting and being able to have these conversations like I’m having with you today, finding other people that you’re like, oh, hold it. How do you guys do this? And how do you very open and sharing? Well, you don’t necessarily find that in other industries, where organizations that are much bigger than yours or maybe much more prestigious, those folks will still be like, Oh yeah, I’ll share this with you. I’ll you know, let me show you how we’re doing it and how what are you guys thinking about? So I have felt it a very welcoming community, both on the family philanthropy side

Gretchen Guess 15:55
and and on the philanthropic side. I think where it’s it’s

Gretchen Guess 16:01
been a bit of a struggle for me is, I think sometimes in philanthropy, we’re about ourselves and not the people we’re serving. It’s about our own theories of change versus Will that really work in a community. We are very community led. I am very community led, and I think we could be more even in proactive philanthropic work. Of why don’t you just go sit and be in community for a bit, be at the coffee shop on the block, or fly into community in and doing things with community instead of to community. Sometimes it still feels a little bit like we’re doing things to community instead of with them, not not all, but I definitely, I’m noticing, noticing a shift. But we think a lot of ourselves in philanthropy, that was a bit of a shock. And, you know, we’re only important because people on the ground doing the work that I mean, they’re really the ones that are important, and I think our job is to lift them up and support them and find, find those folks that are just making a huge difference. And what can we do to help them move forward? So I’m hoping philanthropy starts kind of going this way, and when I run into folks that do rural I find that they’re a lot similar, because we all know that. You know, in rural spaces, you can have all the money in the world, but if you don’t have a few folks on the ground, and if that’s not really what a community wants, it’s not gonna, it’s not gonna work. So it’s, yeah, it’s been it’s been interesting. It’s been an interesting change. I never knew much about the sector before.

Erin Borla 17:59
I think the way you phrased it as being very intellectual. I think is a really strong way to say that, and where I’ve struggled is taking that intellectual moment and the transitioning that to action on the ground. Because you’re exactly right. We can have all these resources, but if we don’t have a way to apply it or implement is same with government funding, right? If it’s all set up, they can have the best policy that’s ever written, but if it’s not applicable or not, you can’t get it done on the ground, it’s not going to do any good.

Gretchen Guess 18:30
Yeah, and it’s hard to say, as you said, you can’t be everywhere at once, yeah? But I think we, I think we can be open and and trusting of what communities think. You know when you’ve run into one of those leaders, you know when a community is behind something, I mean it, it is, it is obvious. And if maybe we can think about our work a little less intellectual and more more like, Oh, these guys are these guys got it? Like, let, let me swear it. And for us, because we come from a banking background, and Elmer and his his son Ed after him, they would do banking deals on a handshake. It was all about the leader. And so that thread runs through us, where, if there’s a good leader. There’s a there’s a woman, Michelle DeWitt in Bethel, Alaska, Michelle says she’s going to get something done. In my board will say it too. It’s like, oh, Michelle’s doing it. Okay? It doesn’t matter what Michelle is doing. She put up permanent supportive housing in 12 months in western Alaska, where the ground is frozen most of the year without even putting a shovel in the ground, because she just she’s one of those leaders that you know is going to get it done. So I think when we find those people, can we be a little bit more flexible? How many constraints are we putting on people? Kind of reporting. Do we really need all those data? Or are we just like we’re so curious that we want them all, and are we thinking about our impact to our grantees, who are one and two person shops? I think there’s, I think there’s some reflective work to do for the sector

Erin Borla 20:22
Alaska has a huge population of indigenous folks. Roundhouse is really committed to finding ways to support and empower indigenous communities. Here in this region, there is very limited capital going to indigenous causes, particularly from philanthropy. How are you approaching that work? How are you also supporting your Alaskan Native corporations alongside other communities that you’re working with? Yeah, a

Gretchen Guess 20:48
lot of the places in Alaska will help both. So you’ll have the city of Hughes in the tribe of Hughes, and some will only have tribal we have 257, tribes, half the tribes in the US or in Alaska. And so what we try to do is, again, it’s accessibility. We invest in travel projects all the time, and trying to make sure that we’re out in community. So they meet us, and so they think about coming. We look at our data and say, who aren’t we even getting applications from? And then we go and spend time in the Copper River Basin, right? So I think you have to do some real proactive, proactive work. We’re also, again, I think when you’re responsive and you’re open, then different projects come to you. Might be a gathering space, it might be language preservation, it might be an indigenous preschool, be be open to what the the tribal needs are, and then what role can you play? But you know, we we work hard. We are we are imperfect. We work hard to make sure that we’re invited in, that we just don’t show up somewhere, and that we’re respectful of what’s going on in that community, and respectful of the councils and and the structures when we’re when we’re there. It’s about building trust, and I think we all can just be aware of all the cultures we interact with, and what happens with those the the other and it’s growing. We’re working on growing it, but we have we’re 20 years into a sabbatical program where we give nonprofit leaders 90 to 120 days off, and we support the organization before the sabbatical, during the sabbatical and after. And five years ago, we expanded that to tribal administrators, and I think that’s another program where that’s very important tribal administrators do everything community. And so how do we give and how do we support a community so their Tribal Administrator can go on sabbatical. I think that’s an important part of our programming is, is, how do we do that? And then we try to be wherever we table a lot. We try to be wherever there’s going to be gatherings. So the Alaska Federation of Natives here were there the entire time, and we talk with folks, when the tribal administrators and the village corps get together, we try to be there. I think it’s just putting ourselves in a lot of different different places, and then being receptive, on the other hand. But you know, we talked about, you smiled earlier about how much data are we asking people? What do the applications look like? We spend a lot of time thinking, thinking about that. Are we making it too difficult for something that could be a really good investment, but we put our own barriers.

Erin Borla 24:22
I love the idea of tabling. I think, you know, when we first started doing the podcast, we had somebody from another foundation say, well, we don’t believe in marketing our foundation, because that doesn’t it feels like self congratulatory. It’s like, oh, I didn’t I Okay. I understand that. I think there is this challenge around what we consider marketing or traditional communications, and I think the value of being present in community and getting people access to your program so they know that it’s available. That’s one way of marketing a service, but the other is this piece of. Storytelling to leverage additional contributions to a program, whether that’s locally, for additional volunteers or to gage and garner additional resources from other funders or from state and federal resources. I think there’s this other opportunity to really be at the table,

Gretchen Guess 25:22
yeah, and to create a table when there needs to when there needs to be, I’ve been spending a lot of time on public media in the last month. The 27 stations, 18 fall on that critical list in in Alaska, and ironically, and I think it, think it was the New York Times reported on that Unalaska was doing an Alaska Public Media was doing the tsunami warning when the rescission went through. Right? But it’s the other thing of trying to, we do have the ability, because of our resources in philanthropy, our name, our ability to convene and connect, which is part of our mission in Rasmussen, to be able to set the table, bring people in. We had about 25 different funders on a call for our all Alaska media plan, because all the stations have come together, and so I think we do have to play that role. And that’s not initially saying, Oh, come because it’s Rasmussen, it’s we just get to set the table. And if we set the table right, then other people come to it. And that doesn’t mean we have to tell people what to do at the table.

Erin Borla 26:38
Yeah. And the doors that philanthropy can open are oftentimes different than the doors that our partners on the ground can even access. So you may set the table, but the fact that you can invite different folks than the folks on the ground can invite, I think that is so helpful,

Gretchen Guess 26:56
it is and it’s trying to figure out how to do that without it being about us, should never be about philanthropy, in my opinion, should always be about the folks that are doing the work, but, but we get to translate, as you said earlier, we get to set the table. And I think those, those roles are really important to philanthropy. And I, and I know the national funders, when you’re place based like you all are like we are. We have to play that role. I mean, we don’t have to, but we are not doing our job. I think, as philanthropy, a place based philanthropy, if we don’t, I shouldn’t expect Doris Duke, right to and Sam, Sam Gill at Doris Duke to know everything about Alaska. I mean, that’s just unrealistic. They need to do what they do best when we need to partner with them and support them in fulfilling their mission within our state, and I think place based funders that that’s one of our roles.

Erin Borla 27:59
Yeah, I think that’s really, really true where we don’t necessarily expect them to know what to be, what to do here, but man, it’s great to get that phone call. And I think many, many of us in these regional community areas are really happy to serve in that role. Pick up the phone. Ask you interested in fun in Alaska.

Gretchen Guess 28:19
Pick up the call me. Please call us. That’s right. We’d love, we’d love to, love to talk with you.

Erin Borla 28:29
So as you look ahead for the next five or 10 years, what is the top priority for you? What are you excited about? What’s keeping you up at night makes you want to tear your hair out?

Gretchen Guess 28:41
I am excited about what feels like a shift in philanthropy towards talking about rural more. You and I are both part of some different groups that are talking about it, and I think some larger organizations want to, and they want to figure it out. So I’m excited to think about, how do we get more dollars into rural from philanthropy? How do we make it easier? How do we have people just see the inherent benefit of funding rural versus just being intimidated by it or not understanding how to do it. I think we’re really in a moment of time within philanthropy, where the culture and the resilience and what you can do in rural and the importance of rural is standing up. So I’m excited to see where that goes and be part of those conversations, and that includes if the federal government is going to change its approach. We all know that government doesn’t work perfectly, and wasn’t working perfectly for rural so let’s be at the table on what could be better to me, do you know let’s seize the opportunities of the day, and can we get back to more local control? Community driven even with with our federal funds. I think you know what keeps me up at night? Alaska gets more federal funds per capita than anywhere and in the nation, we’re a young state that hasn’t had hundreds of years of infrastructure. Again, we have places without water, without sewer. So what’s that going to look like? We are one of just a handful of philanthropies in Alaska, and we’re the largest by, you know, 20 fold. So how do we navigate? How we help the state? What our role is, is is what keeps me up at night? What’s my role as a leader in in the state? How? How are we going to navigate these times? But the nice thing is, it’s Alaska, and we’re always going to do it. We’re just we’re resilient, we’re going to figure it

Erin Borla 30:58
out. Yeah, yeah. It’s been such a gift to get to know you over the even just the past few months, I think we ran into each other almost on accident. We I was in Alaska for a conference, and you were there, and it’s like, Oh, we’ve crossed emails, no and so, and here we are, and I just have so appreciated all of your work, even today, like, Oh, I’m going to follow up and learn about these two other projects you mentioned, because that’s something that we can offer here, and so we can learn so much from one another just spending time together. And I really appreciate you taking time today to share what you’re working on and and really talk about Alaska, because I do think there, we often talk about rural but, but Alaska is a is a different.

Gretchen Guess 31:42
It’s a different, it’s a different rural but we all have the same barriers and the same people. So you

Erin Borla 32:12
even though Alaska is a different rural we all have the same barriers. I really appreciated the way that Gretchen noted that she referred to Rasmussen as a responsive grant maker, responding to what the community needs when they say they need it, and letting the community drive that information forward. I think sometimes in philanthropy, we really get caught in our own strategic planning and our own strategic initiatives, and forget how to let the community drive what they really want and what they need, keeping those open call opportunities available. I know for roundhouse, that’s been really helpful. It allows us to bring in community reviewers and have the opportunity to really lean on our community partners to have a better understanding of what’s happening on the ground. Those open call opportunities help so we don’t miss anything

Erin Borla 33:02
some of the things that she mentioned that they’re doing in Alaska, I wish that we did here. And I think we’re going to try and pick those up open coffee hours and community when they’re traveling to different places, just a time for community members and organizations to come and check in, having the availability of program officers and other program or grant staff to have an appointment booked online. Those are brilliant

Erin Borla 33:27
philanthropy can sometimes get too academic, too theoretical, too much in our own head and sometimes in our own way. So how do we take that practice, what we learn, what we research, and apply it and allow communities to apply it to really make change. Thanks for listening to funding rural. Check us out online at funding rural.com you.

Transcribed by AI. Please forgive any mistakes.

Published On: October 21st, 2025 / Categories: Season 3 /