Matt Fogarty on Humanizing Homelessness, Community, and Hope


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Key Takeaways

  • Human connection is often the first step toward empathy and understanding.
  • Homelessness is a complex systemic issue, not an individual failure.
  • Many nonprofit founders are building the support systems they once needed themselves.
  • Authentic community creates space for healing, belonging, and action.
  • Small acts of service can create ripple effects far beyond what we see.

There are some people who enter nonprofit work because they discover a cause. Others arrive because they discover a community.

For Matt Fogarty, founder of Cherry Willow Apparel and Cherry Willow Technology, both happened at the same time.

What began as a commitment to service eventually became a mission to challenge the stories people tell themselves about homelessness, belonging, and who deserves compassion. Along the way, Matt has partnered with more than 70 nonprofits, amplified community voices through apparel and storytelling, and spent countless hours listening to people whose experiences are too often reduced to stereotypes.

Again and again, he has come back to the same conclusion:

“You really don’t know about people until you connect with them in person.”

In a world that often encourages distance, assumptions, and quick judgments, Matt’s work is rooted in something much simpler: human connection.

Transcript

Nicole Jamrozinski: [00:00:00] Hi, Matt. Thank you so much for being here today. I’m really looking forward to this conversation and hearing about all the amazing and cool work that you’re doing. So to kick us off, I was hoping you could introduce yourself and tell us about the kind of work that you’re focused on right now. 

Matt Fogarty: Yeah, absolutely.

Matt Fogarty: Thank you so much for having me on, Nicole. Um, my name is Matt Fogarty. I am the founder of Cherry Willow Apparel, um, and also Cherry Willow Technology. Uh, Cherry Willow, we are focused on advocating and providing education around homelessness, uh, with the goal of, you know, increasing the visibility of the people that homelessness impacts and encouraging empathy, uh, not otherization of these people so that we can really address the systemic change that’s needed, uh, to end things like homelessness.

Matt Fogarty: Um, and through that work we’ve also partnered with over 70 different non-profits to help them use apparel as a fundraising tool, uh, but then also really importantly, as a [00:01:00] marketing and branding tool so that they can increase the visibility of the amazing work that they’re doing in the communities that they work in 

Nicole Jamrozinski: I love that.

Nicole Jamrozinski: I think, um, there’s so much your clothes can say about you, but also the, uh, it’s a fun way to also support the charity or the organization that you might, uh, also love and find different ways to bring their message to light. I love that work. So I’m curious, what kinda drew you into this work in the first place?

Nicole Jamrozinski: Was there a specific moment or a person or experience that helped shape that path? 

Matt Fogarty: Yeah, absolutely. So Cherry Willow actually comes from the two streets that I grew up on in Ohio, and that was where I first learned about the value of service work. Um, my mom has had cancer since I was a youngster. Uh, I think I was 10 or 11 when she got her first diagnosis.

Matt Fogarty: And despite that, you know, we were always out serving others in the community. Uh, so we were greeters at church on Sunday. You know, we would [00:02:00] volunteer and serve meals to migrant workers in our community. My mom would make meals for St. Vincent de Paul. And so that was where I, like, first had the heart for service work.

Matt Fogarty: And then, you know, as I progressed throughout my life and my career, you know, I studied and had an opportunity to serve people experiencing homelessness at Loyola University Chicago, and really addressed a lot of misconceptions that I had about the people impacted by homelessness, um, through meeting them.

Matt Fogarty: And you really don’t know about people until you connect with them in person. And so that’s what I always encourage people to do is, you know, the next time you see someone that’s currently homeless, just stop and introduce yourself. You know, it… That little bit of human connection can go a long way, and I’ve actually heard stories from people that it helped be a part of what saved their life and, you know, they didn’t end up moving forward with suicide because someone stopped and was kind to them that day.

Matt Fogarty: Um, and so that, you know, really spirit of unconditional love for all [00:03:00] people is, uh, something I try to embody. But it wasn’t until I got laid off from a startup job that I actually took the plunge to start, you know, Cherry Willow. Um, and you know, that experience was a little bit about the illusion of security that jobs represent.

Matt Fogarty: It’s like you can feel secure, uh, and you can do great work, and then, you know, there’s a, a shift or a, a misalignment of the organization and everything that you’ve done, you know, can be washed away just because it’s not aligned with where they’re moving forward or the profitability or the investors, whatever the case might be.

Matt Fogarty: Um, so that was what encouraged me and emboldened me to really set off on my own and then start building something of my own. 

Nicole Jamrozinski: Sometimes when a door closes, another one opens and it’s where you’re exactly supposed to be. So I’m happy that you landed over here. I also really love what you said around, um, taking the time to, like, actually listen or hear, be kind to somebody and hear, um, about their life or their [00:04:00] perspective.

Nicole Jamrozinski: I think that’s such a undervalued component in how we operate. Like, we were always told to be afraid of strangers or don’t talk to strangers, and sometimes just showing kindness to a stranger can change their, their perspective, your perspective. Um, it’s another door opening that I think we need more often than not right now in society.

Nicole Jamrozinski: So, uh, I love the work that you’re doing, and I’m really happy that you found your way to Cherry Willow. That’s awesome. 

Matt Fogarty: Appreciate it. Thank you. 

Nicole Jamrozinski: So I’m curious, as you’re building and hearing from the people that you’re working with, are, is there something that feels especially challenging in the sector right now or, like, sticky moments that you’re trying to overcome?

Matt Fogarty: Yeah, I think in, in homelessness space, um, there is a huge push towards criminalization right now, and there are really well-funded organizations like The Heritage Foundation that are [00:05:00] backing that agenda. And so that’s something that’s really frustrating because, you know, w- if you look at the data, if they actually want people to improve and be empowered, you know, the best way to do that is by providing housing first, and then surrounding with support systems.

Matt Fogarty: Um, you know, asking someone that’s homeless, either living unsheltered or in a shelter, to have a foundation to build from for their own mental health or physical health or, you know, uh, workforce development type of opportunities, is extremely challenging. And, you know, these organizations are pushing more forced treatment plans, which if you’ve ever known somebody that’s struggling with mental health or addiction, if that person’s not ready to make a change, forcing them into treatment is not going to benefit anybody.

Matt Fogarty: Um, and so that’s something that is really challenging right now because the public is tired of seeing people on the street, uh, whether from human empathetic reasons or just from selfish, you know, n- reasons of not wanting to see that in their [00:06:00] city. And so organizations like The Heritage Foundation are using that, and they’re painting and controlling the narrative around homelessness, and they’re being successful in blaming these individuals rather than highlighting the systemic nature of, you know, housing being a human right and something that’s been commodified, and, you know, wages not keeping up with cost of living.

Matt Fogarty: Um, that’s a huge factor in the rise of homelessness, and there’s so many different forms of homelessness. Like, most people have experienced homelessness. If you’ve ever, you know, been between a lease and you crashed on with a friend or a family member for a month or two, you know, that is a form of homelessness that doesn’t show up in the point in time counts.

Matt Fogarty: Um, you know, I had to live in an extended stay motel for a month and a half in, when I was going through my divorce, and extended stay motels are a very common form of homelessness. And those folks, you know, they’re not afforded the same, like, tenant, uh, landlord rights because it’s a [00:07:00] hotel. And, you know, organizations like BlackRock have taken advantage of that because the, in 2021, during COVID times, they bought Extended Stay America for billions of dollars because it had over an 80% occupancy rate when most other hotels in the hospitality industry, you know, were occupancy rates below 10.

Matt Fogarty: But because this has been, like, people’s permanent form of housing essentially, that’s, that’s just a whole dynamic that, like, it’s very profitable for people to be impoverished, and, you know, we really need to change those systems, uh, if we want to affect change at, you know, at the national scale. 

Nicole Jamrozinski: Yeah.

Nicole Jamrozinski: That’s such a, it’s like a convoluted problem because it is systemic. There’s so many different intersections and avenues that feed into why or, um, solutions on how to solve some of these challenges. And what you’ve identified Yeah, they’re b- they’re big discussions, and it’s, it affects people differently.

Nicole Jamrozinski: I think people see [00:08:00] they’ve experienced themselves or, you know, they don’t like seeing it, so they, they, like, push away from it. Um, I think those are… They’re hard and big discussions that we need to grapple with, though. Because the reality is they’re, the pr- the housing costs, the, um, h- the food costs, like, all of those things are just increasing, and it seems that the, the margin is just getting larger and larger.

Nicole Jamrozinski: So I’m, I’m afraid that more people are going to start experiencing homelessness, and if we can’t get in front of some of these solutions or at least just have honest conversations about what the realities are and why they may be playing into this, this issue, um, we’re not gonna solve it. So I love that you’re having these honest conversations.

Nicole Jamrozinski: You’re, you’re bringing them to the forefront. I think they’re crucial if we’re actually gonna make any impact or change. So thank you for, for highlighting that, that issue, for [00:09:00] sure. I am curious. Obviously, like, that’s a, a big challenge to overcome and something that you- you’re focusing on the regular.

Nicole Jamrozinski: What’s bringing you energy or hope lately to help kind of combat that, that issue, or in general across the, the board? 

Matt Fogarty: Yeah. Yeah, so I mean, since I’ve been, you know, focused on the nonprofit space the last few years, something that constantly provides energy for me is getting to connect with amazing people that are doing great work in their communities.

Matt Fogarty: So, you know, like last week, uh, we actually just got done with our second Pedal for Progress initiative, um, where I biked from Jacksonville down to Miami, and we connected with over a dozen different organizations. And getting to hear the stories of the founders, um, who have created spaces and systems that if those existed for them, you know, th- would not have led them to be in those situations.

Matt Fogarty: And so that’s [00:10:00] always really inspiring for me is people that have endured difficulty, they’ve overcome tragedy, and they have poured themselves back into the people that are going through similar experiences. Um, like one story from last week that stuck out was, uh, Angels of Mercy Ministries, where, you know, they, the founder was in prison herself, uh, for a number of years, uh, because of a, a DUI and, uh, something that resulted in, I believe, the loss of life of someone else that was in the accident.

Matt Fogarty: And, you know, she’s been able to create a space now for women coming out of the prison system to have a safe place to build from again, to rebuild themselves, and to give a second chance. And, you know, so often our systems just throw people to the wayside- Mm-hmm … or, you know, like one of our phrases at Cherry Willow is, “Humanize, not otherize.”

Matt Fogarty: And there’s- it’s very easy to otherize people. Like, “Oh, that’s someone that’s homeless, that could never be me,” or, “Oh, that’s someone [00:11:00] that, you know, committed a crime, like that would never be me.” And, you know, really that’s, that’s all of us. And so being able to help support people and create a safe space in an environment that you didn’t have, like that’s something I see time and time again when I connect with these nonprofit founders, is they are creating systems that would’ve helped them.

Matt Fogarty: Mm-hmm. And instead of focusing on like what they didn’t have, they’ve now taken that as an opportunity to create something really meaningful and impactful, and, and that work always fills me up. Um, and it always energizes me and inspires me to go out and do more. And that’s really what the work at Cherry Willow is about, is to inspire anyone out there to take action in some way to support their community.

Matt Fogarty: So even if it’s something like buying a piece of merchandise from a nonprofit, you know, that helps provide them with some funding, but then it also gives them an advocate out in the community, and you can tell the story of that organization and why you care about the [00:12:00] work that they’re doing, and why the work that they’re doing is important.

Matt Fogarty: And, you know, the, the butterfly effect, you have no idea what that small action today manifests itself into as more people, you know, begin to act on that as well. And so those small actions do make a big difference. Um, and I encourage you, if you’re watching this, like you’re thinking about getting involved, you know, just follow along with some nonprofits that you’re supportive of.

Matt Fogarty: Um, reach out to them, you know, and say, “Hey, how can I help?” And, you know, be, be open to whatever they say, and then just try to get yourself involved consistently and I think that you’ll feel really good, and more than likely you’ll find people that you’re really aligned with. Yeah. And I, I think it’s the people in our communities that, that really help provide us energy, and the connections that we make are, are so valuable and, and so uplifting.

Nicole Jamrozinski: 100%. Could not agree more, and I think getting involved with your local charities, local community, whatever that is, is so important to just open, open the door and create [00:13:00] those natural opportunities to connect with folks. I’m curious, what do you think becomes possible when you have people connect honestly?

Nicole Jamrozinski: So why do spaces for connection and community matter in this work? 

Matt Fogarty: Yeah, I think, um, a lot of people, like, we consume content, right? So whether that’s, you know, social media, whether it’s movies, television, whatever the case might be. And w- when we’re consuming that content, like, that’s- it’s mostly not authentic.

Matt Fogarty: You know- Mm-hmm … it’s people that are putting on a production, you know, people that are putting on a show. Um, and even on social media, it’s people projecting a version of themselves that they want to be viewed as. Uh, and so I think when you have the space for authenticity, um, and especially with AI, like it’s, it’s so challenging now to know, like, what is real, what isn’t real when it comes to online content.

Matt Fogarty: So I think that there’s gonna be a, a rise of in-person events [00:14:00] because you can’t fake that type of authenticity. You can’t simulate that interaction, you know, virtually. And being able to connect with people, you know, in a space and being safe to be authentic, like, I think a, a great example of that is AA.

Matt Fogarty: You look at, like, those groups, they come together and they tell, you know, stories that oftentimes could’ve been very traumatic. But we start to realize and see that we’re all very similar, you know? We all have gone through really challenging situations. Mm-hmm. We’ve all experienced trauma in different forms or fashions throughout our lives, and we don’t have to hide that.

Matt Fogarty: You know, we don’t have to- Mm-hmm … put on these masks and be what society tells us we can be. And once you start acting authentically, um, you know, it’s interesting who stays around and who kind of, that vibrational shift in your identity. You know, you may lose some folks, and you have to be okay with that because if, if you are having to be someone [00:15:00] that you’re not in order for those connections to stay around, then most likely they weren’t very healthy and they weren’t serving you in the right way.

Matt Fogarty: Um, and so that’s something that I think, you know, why making that space for community and connection, showing up authen- authentic- phew, authentically, um, is extremely important and it’s a very brave thing to do. Uh, and I think that’s what nonprofits inspire a lot of folks to do- Mm-hmm … because we’ve all struggled at times.

Matt Fogarty: It can be really challenging to ask for help. People can feel really lonely and isolated in their problems. But when you do begin to share them, you start to see that there are others going through a similar circumstance. And, you know, asking for help is a really brave thing to do. And then when you’re out there helping others, it’s really difficult to feel alone.

Matt Fogarty: Um, and so I think that’s what’s so powerful about community. 

Nicole Jamrozinski: I love that, Matt. I think, um, you’ve summed that up so nicely, and it’s just, I think you’re 100% on point about seeing the rise of in-person events, the need [00:16:00] for people to connect with one another. I think the nonprofit sector as a whole has identified the gap areas in, gap areas in the social construct.

Nicole Jamrozinski: So there’s natural ways for you to get involved, because you can see yourself in the work, or you have an opportunity to be your authentic self in those spaces, ’cause you may have experienced something in that, in that, um, in that way as well. So I just appreciate your authenticity and you showing up here today.

Nicole Jamrozinski: Um- Thanks for having me … to anyone who’s listening, I just wanna say thank you again to Matt for joining us, and if you haven’t had a chance, please join the Nonprofit Hive. Uh, you’ll also have a chance to meet amazing members like Matt throughout those conversations and get the opportunity to connect one-to-one.

Nicole Jamrozinski: Thank you so much, Matt. I really appreciate it. 

Matt Fogarty: Yeah, absolutely. Thank you so much for having me on, Nicole. And yeah, for anyone watching, uh, joining the Hive was an incredible decision, and I’ve met so many [00:17:00] wonderful people, and it’s, it’s just amazing to be connected with people that are making an impact in their communities.

Matt Fogarty: And you never know where those connections might lead, and you know, how you may be able to help them or they’ll be able to help you. Uh, just so many wonderful people in the Hive, and I appreciate being a part of it. 

Nicole Jamrozinski: Amazing. Matt, I do have one more question for you. Where can people find you, and how can they follow along?

Matt Fogarty: Yeah, absolutely. So we put out a lot of content on Cherry Willow Apparel, so on LinkedIn, Facebook, Instagram, TikTok. Um, if you wanna follow along with me personally, you can connect with me on LinkedIn, uh, or I also put stuff out on TikTok, uh, Facebook, and Instagram, and also YouTube, uh, for Cherry Willow as well.

Matt Fogarty: Uh, my personal handles are Fog, F-O-G, the number two, and then F-O-G-E, Foge, which is my nickname. And that’s a, the little bit of story about my personal transformation from kind of being in a fog and not knowing what I wanted to do with my life to, to finding myself and, you know, finding my purpose, which I have, you know, through Cherry [00:18:00] Willow these last few years.

Matt Fogarty: And so I try to share stuff about personal transformation, positive reframes, other different philosophy, psychology, mindset type of training and books that I’ve read, um, and just also some improv comedy, you know, ’cause you gotta keep it light. 

Nicole Jamrozinski: Why not? Love it. Amazing. Thank you so much, Matt, and I look forward to following along.

Matt Fogarty: Absolutely. Thank you again, Nicole. 

Nicole Jamrozinski: Take care. 

Matt Fogarty: Bye.

Service Was Always Part of the Story

Long before Cherry Willow existed, service was part of everyday life.

Growing up in Ohio, Matt watched his mother navigate a cancer diagnosis while continuing to show up for others. Whether it was serving meals, volunteering through church, or supporting people in the community, helping others wasn’t treated as something extraordinary. It was simply what you did.

That foundation stayed with him.

Later, while attending Loyola University Chicago, Matt began working alongside people experiencing homelessness. Those experiences challenged many of the assumptions he didn’t even realize he was carrying.

Meeting people face-to-face changed the conversation.

“You really don’t know about people until you connect with them in person,” he says. “The next time you see someone that’s currently homeless, just stop and introduce yourself. That little bit of human connection can go a long way.”

The lesson wasn’t just about homelessness. It was about what becomes possible when we move beyond labels and allow ourselves to see the person standing in front of us.

Cherry Willow itself emerged after another turning point. Following a layoff from a startup role, Matt began questioning what security really meant and what kind of work he wanted to dedicate himself to.

What initially felt like uncertainty became an opportunity to build something that aligned more closely with his values.


Changing the Conversation Around Homelessness

Much of Matt’s work today focuses on helping people better understand the realities of homelessness. That feels increasingly important as public conversations become more polarized.

While homelessness is often discussed as an individual problem, Matt sees it as a reflection of larger systems: housing affordability, stagnant wages, access to support services, and the growing gap between what people earn and what it costs to live.

He is also quick to point out that homelessness looks different than many people imagine.

“If you’ve ever been between a lease and you crashed with a friend or family member for a month or two, that’s a form of homelessness,” he explains.

Those experiences rarely show up in official statistics, but they are part of a broader reality many people are much closer to than they realize.

What concerns Matt most is how easily people experiencing homelessness become separated from the rest of society in public narratives. One phrase has become central to his work:

“Humanize, not otherize.”

“It’s very easy to otherize people,” he says. “‘Oh, that’s someone that’s homeless. That could never be me.’ Or, ‘That’s someone who committed a crime. That would never be me.’ Really, that’s all of us.”

For Matt, meaningful change starts when we stop viewing people as categories and start recognizing our shared humanity.


The People Who Keep Him Hopeful

The challenges surrounding homelessness are significant, but Matt doesn’t spend much time talking about hopelessness. Instead, he talks about people.

One of the things that energizes him most is meeting nonprofit leaders who have transformed difficult experiences into opportunities for others.

Through Cherry Willow’s partnerships and initiatives like Pedal for Progress, he has met founders who have experienced incarceration, addiction, housing instability, loss, and trauma. Rather than allowing those experiences to define them, they have chosen to build something for the people coming behind them.

What stands out is a common pattern. “I see time and time again when I connect with these nonprofit founders, they are creating systems that would’ve helped them,” Matt says.

“Instead of focusing on what they didn’t have, they’ve now taken that as an opportunity to create something really meaningful and impactful.”

It’s a perspective many nonprofit professionals will recognize. Some of the strongest organizations are built by people who understand the problem personally. Not because they have perfect answers, but because they know what it feels like to need support.

Why Authentic Connection Matters More Than Ever

Toward the end of our conversation, Matt reflected on something many nonprofit professionals are feeling right now: a growing hunger for authenticity.

“We consume content all day,” he says. “But it’s mostly not authentic.”

Whether it’s social media, advertising, or increasingly AI-generated content, much of what people encounter online is curated, polished, and carefully constructed. Real connection feels different.

“I think there’s going to be a rise of in-person events because you can’t fake that type of authenticity,” Matt says. “You can’t simulate that interaction virtually.”

For people working in the nonprofit sector, where burnout, isolation, and emotional labour are common realities, those spaces matter. When people share honestly, they begin to realize they are not carrying their challenges alone.

“It can be really challenging to ask for help,” Matt reflects. “People can feel really lonely and isolated in their problems. But when you begin to share them, you start to see that there are others going through a similar circumstance.”

That, he believes, is the real power of community. Not networking. Not transactions. Not appearances. Simply creating spaces where people can show up as themselves and be met with understanding.


Seeing Ourselves in Each Other

What stands out most about Matt’s perspective is not that he offers easy solutions to complex problems. It’s that he continually returns to relationships.

Relationships between neighbours. Relationships between communities. Relationships between people who might otherwise never have met.

The issues surrounding homelessness are complicated. The systems involved are vast. But Matt’s work serves as a reminder that meaningful change often starts with something surprisingly small.

A conversation. A moment of kindness. An introduction. A willingness to see ourselves in someone else’s story.

Because when we do that, it becomes much harder to look away.


If this feels familiar, you are not alone in it. That is part of what makes spaces like The Nonprofit Hive matter. They reflect back what many are already carrying and create space for people to move through it together.

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